STRUCTURE OF ADJUSTABLE STERIC HINDRANCE WEAK BASIC LIGHT STABILIZER AND PREPARATION METHOD AND APPLICATION THEREOF

Abstract

The field of new compounds and synthesis methods thereof are related, and particularly to a structure of a steric hindrance adjustable weak base light stabilizer and a preparation method and application thereof. According to the innovative light stabilizer, a steric hindrance thereof is adjusted by establishing substituent generating the steric hindrance around nitrogen atoms; moreover, an electronegativity of the nitrogen atom can be influenced by adjusting a distance of a polar group, so that an alkalinity or a nucleophilicity of the nitrogen atom is adjusted. A desired effect is obtained by adjusting a steric hindrance and a nucleophilic property or an alkalinity where the nitrogen atom is located, so that an application range of the innovative light stabilizer is widened, and the innovative light stabilizer is suitable for PC, polyester, PVC and other slightly acidic or certain electrophilic polymer materials to serve as a light stability protecting aid.

Claims

1. A structure of a steric hindrance adjustable weak base light stabilizer, wherein structural formulas are as follows: structural general formula 1: ##STR00156## wherein, in the structural general formula 1, X is NH, NR3 or O; Y is H, methyl or other alkyl; R is 5-22 linear alkyl, branched alkyl, or —(CH.sub.2)nSi(OMe).sub.3, or —(CH.sub.2)nSi(OEt).sub.3, and n is 2, 3, 4, or 5; R1 is C1-C20 linear alkyl, or branched alkyl, or double-bond substituted alkyl, or heteroatom substituted alkyl, or hydroxyl or alkoxy; or i-Pr, i-Bu, isoamyl, isooctyl, cyclohexyl, substituted cyclohexyl, cyclopentyl, benzyl, substituted benzyl, allyl, substituted allyl, double-bond contained alkyl, or aryl substituted alkyl, or —(CH2)n-NR4R5; R4 and R5 are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, cyclohexyl, or benzyl; or ##STR00157## or —(CH2)n-Si(OEt).sub.3, and n is 2, 3, 4, or 5; and when R1 is neither —(CH2)n-NR4R5 nor —(CH2)n-Si(OR).sub.3, R and R1 are the same or different; or structural general formula 2: ##STR00158## wherein, in the structural formula 2, X is NH, NR3, or O; Y is H, methyl, ethyl, or other alkyl side chains; R is 5-22 carbon linear or branched alkyl; R1 and R2 are linear or branched alkyl, or i-Pr, i-Bu, isoamyl, isooctyl, cyclohexyl, substituted cyclohexyl, cyclopentyl, benzyl, substituted benzyl, allyl, substituted allyl, double-bond contained alkyl, aryl substituented alkyl, or ##STR00159## or R1 and R2 are both ##STR00160## R1 and R2 are the same or different; and R is the same as or different from R1 and R2; when R1 and R2 are different, R1 is Et, i-Pr, n-Pr, Bu, i-Bu, or C5-12 alkyl; and R2 is ##STR00161## hydroxyethyl, or hydroxypropyl; or structural general formula 3: ##STR00162## wherein, in the structural formula 3, X is NH, NR3, or O; Y is H, methyl, ethyl, or other alkyl; R is —(CH2)n-, wherein n ranges from 2 to 22, or R is alkyl, or aryl side chain substituted —(CH2)n-, or dibenzylamine; R1 and R2 are alkyl, or i-Pr, i-Bu, isoamyl, isooctyl, cyclohexyl, substituted cyclohexyl, cyclopentyl, benzyl, substituted benzyl, allyl, substituted allyl, double-bond contained alkyl, aryl substituented alkyl, or ##STR00163## R1 and R2 are both ##STR00164## R1 and R2 are the same or different; when R1 and R2 are different, R1 is Et, i-Pr, n-Pr, Bu, i-Bu, or C5-12 alkyl; and R2 is ##STR00165## or hydroxyethyl, or hydroxypropyl; or structural general formula 4: ##STR00166## wherein, in the structural formula 4, X is NH, NR3, or O; Y is H, methyl, ethyl, or other alkyl; n is 2-18 linear paraffin —(CH2)n-, or side chain alkyl or aryl substituted alkane; R1 is methyl, ethyl, propyl, or butyl; or i-Pr, i-Bu, cyclohexyl, substituted cyclohexyl, cyclopentyl, benzyl, substituted benzyl, allyl, substituted allyl, double-bond contained alkyl, or aryl substituented alkyl; or R1 is ##STR00167## R is C5-C20 linear or branched alkyl, or alkyl side chain and aryl substituented alkyl; or —CH2CH2CH2-Si(OMe).sub.3, or —CH2CH2CH2-Si(OEt).sub.3; or structural general formula 5: ##STR00168## wherein, in the structural formula 5, X is NH, NR3, or O; Y is H, methyl, or other alkyl; n is 1, 2, 3, 4, or 5; and n1 is 1, 2, 3, 4, or 5; n is equal to n1, or n is not equal to n1; R is C5-C22 linear or branched alkyl, or alkyl side chain and aryl substituented alkyl; and R is —CH2CH2CH2-Si(OMe).sub.3 or —CH2CH2CH2-Si(OEt).sub.3; or structural general formula 6: ##STR00169## wherein, in the structural formula 6, X is NH, NR3, or O; Y is H, methyl, ethyl, or other alkyl; n is 1, 2, 3, 4, or 5; and n1 is 1, 2, 3, 4, or 5; n is equal to n1, or n is not equal to n1; n2 ranges from 2 to 18; and n3 ranges from 2 to 35, which is a polymerization degree of an oligomer, or structural general formula 7: ##STR00170## wherein, in the structural formula 7, X is NH, NR3, or O; Y is H, methyl, ethyl, or other alkyl; n1 is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22; n ranges from 1 to 15, which is a polymerization degree of an oligomer, n is equal to n1, or n is not equal to n1; R is C2-C18 linear or branched alkane; or isopropyl, isobutyl, isopentyl, isohexyl, isooctyl, or isodecyl; and R is double-bond contained alkyl; or heteroatom contained substituent, or —OH, —OR1, ester group, carboxyl, or nitrile group.

2. A preparation method of the structure of the steric hindrance adjustable weak base light stabilizer according to claim 1, comprising the reaction formulas as follows: structural general formula 1: ##STR00171## structural general formula 2: ##STR00172## structural general formula 3: ##STR00173## structural general formula 4: ##STR00174## structural general formula 5: ##STR00175## structural general formula 6: ##STR00176## structural general formula 7: ##STR00177##

3. The preparation method of the structure of the steric hindrance adjustable weak base light stabilizer according to claim 1, comprising the specific steps as follows: a preparation method of the structural general formula 1: (1) under the protection of nitrogen, adding methyl acrylate or methyl methacrylate into a reaction flask, starting stirring, adding methanol, or ethanol, or acetone, or ethyl acetate, or dichloroethane, or DMF, or not adding any solvent, adding a catalyst 1, wherein the catalyst 1 is acetic acid, or acidic alumina, or silica gel, or ortho-methoxyhydroquinone, or 4,4′-benzophenone, or m-nitrophenol, or silica gel sulfate, cooling to 5° C. to 10° C., and then dropwise adding first amine slowly; heating to a room temperature after dropwise adding, stirring, and heating to continue the reaction; monitoring the reaction process by TLC until the reaction is complete, removing excessive methyl acrylate under vacuum, and using the remaining reaction intermediate without further purification for next reaction; (2) under the protection of nitrogen and stirring, adding 0.1% to 5% of catalyst 2 into the intermediate obtained in the first step at a room temperature, wherein the catalyst 2 is sodium methoxide, sodium formate, diethyl tin oxide or aluminum isooctanol, then adding n-dodecylamine, or n-octadecylamine, or n-dodecanol, or n-octadecanol in batches, after finishing adding, heating to 40° C. to 700 for reaction for 5 hours to 16 hours, continuously heating to 85° C. to 1200 for reaction for 30 hours to 96 hours, and monitoring the reaction process by TLC until the reaction is complete; and adding ethanol, or ethyl acetate or petroleum ether containing 5% to 15% of water for recrystallizing, filtering to yield a white powder solid product, and drying, wherein a yield ranges from 85% to 97%; a preparation method of the structural general formula 2: (1) under the protection of nitrogen, adding methyl acrylate or methyl methacrylate into a reaction flask, starting stirring, then adding 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF, or not adding any solvent, adding 0.02% to 30% of catalyst 1, wherein the catalyst 1 is acetic acid, or acidic alumina, or silica gel, or ortho-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol, cooling to SC to IO, and then dropwise adding second amine slowly; heating to a room temperature after dropwise adding, stirring for 6 hours to 24 hours, and if the reaction needs to be continued, continuously heating to 40° C. to 80° C. to continue the reaction for 5 hours to 18 hours; monitoring the reaction process by TLC until the reaction is complete, removing excessive methyl acrylate under vacuum, and using the remaining reaction intermediate without further purification for next reaction; (2) under the protection of nitrogen and stirring, adding 0.1% to 5% of catalyst 2 into the intermediate obtained in the first step at a room temperature, wherein the catalyst 2 is sodium methoxide, sodium formate, diethyl tin oxide or aluminum isooctanol, then adding n-dodecylamine, or n-hexadecylamine, or n-octadecylamine, or n-dodecanol, or n-octadecanol in batches, after finishing adding, heating to 40° C. to 70° C. for reaction for 8 hours to 16 hours, continuously heating to 85° C. to 140° C. for reaction for 48 hours to 96 hours, and monitoring the reaction process by TLC until the reaction is complete; and removing the catalyst, adding ethanol, or methanol, or ethyl acetate, or petroleum ether containing 0.50, to 20% of water for recrystallizing, filtering to yield a white powder solid product, and drying, wherein a yield ranges from 87% to 96%; a preparation method of the structural general formula 3: (1) under the protection of nitrogen, adding methyl acrylate or methyl methacrylate into a reaction flask, starting stirring, then adding 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF, or not adding any solvent, then adding 0.01% to 30% of catalyst 1, wherein the catalyst 1 is acetic acid, or acidic alumina, or silica gel, or ortho-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol, cooling to 5° C. to 20° C., and then dropwise adding second amine slowly; heating to a room temperature after dropwise adding, stirring for 5 hours to 24 hours, and if the reaction needs to be continued, continuously heating to 40° C. to 80° C. to continue the reaction for 5 hours to 18 hours; monitoring the reaction process by TLC until the reaction is complete, removing excessive methyl acrylate under vacuum, and using the remaining reaction intermediate without further purification for next reaction; (2) under the protection of nitrogen and stirring, adding alkyl diamine, such as ethylenediamine, or butanediamine, or hexamethylenediamine, or decanediamine in batches first into the intermediate obtained in the first step at a room temperature, then adding 0.1% to 5% of catalyst 2, wherein the catalyst 2 is sodium methoxide, sodium formate, diethyl tin oxide or aluminum isooctanol, after finishing adding, heating to 50° C. to 70° C. for reaction for 6 hours to 16 hours, continuously heating to 85° C. to 120V for reaction for 48 hours to 96 hours, and monitoring the reaction process by TLC until the reaction is complete; and removing the catalyst, adding ethanol, or methanol, or ethyl acetate, or petroleum ether containing 0.5% to 20% of water for recrystallizing, filtering to yield a white powder solid product, and drying, wherein a yield ranges from 85% to 95%; a preparation method of the structural general formula 4: (1) under the protection of nitrogen, adding methyl acrylate or methyl methacrylate into a reaction flask, starting stirring, then adding 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF, or not adding any solvent, then adding 100 ppm to 1000 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol, cooling to SC to 20° C., and then dropwise adding second amine slowly; heating to a room temperature after dropwise adding, stirring for 8 hours to 32 hours, and if the reaction needs to be continued, continuously heating to 40° C. to 60° C. to continue the reaction for 5 hours to 24 hours; monitoring the reaction process by TLC until the reaction is complete, removing excessive methyl acrylate under vacuum, and using the remaining reaction intermediate without further purification for next reaction; (2) under the protection of nitrogen and stirring, adding dodecylamine, or hexadecylamine, or octadecylamine, or hexadecanol, or octadecanol, or dodecanol in batches first into the intermediate obtained in the first step at a room temperature, then adding 0.02% to 5% of catalyst 2, wherein the catalyst 2 is sodium methoxide, or sodium formate, or diethyl tin oxide, or aluminum isooctanol, after finishing adding, heating to 50° C. to 70° C. for reaction for 8 hours to 10 hours, continuously heating to 80° C. to 120° C. for reaction for 48 hours to 96 hours, and monitoring the reaction process by TLC until the reaction is complete; and removing the catalyst, adding ethanol, or methanol, or ethyl acetate, or petroleum ether containing 0.5% to 20% of water for recrystallizing, filtering to yield a white powder solid product, and drying, wherein a yield ranges from 83% to 96%; a preparation method of the structural general formula 5: (1) under the protection of nitrogen, adding methyl acrylate or methyl methacrylate into a reaction flask, starting stirring, then adding 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF, or not adding any solvent, then adding 100 ppm to 1000 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol, cooling to 10° C. to 20° C., and then dropwise adding cyclic alkyl diamine slowly; heating to a room temperature after dropwise adding, stirring for 3 hours to 5 hours, heating to 40° C. to 60° C. to continue the reaction for 10 hours to 24 hours; monitoring the reaction process by TLC until the reaction is complete, removing excessive methyl acrylate under vacuum, and using the remaining reaction intermediate without further purification for next reaction; (2) under the protection of nitrogen and stirring, adding octadecylamine, or dodecylamine, or hexadecylamine in batches first into the intermediate obtained in the first step at a room temperature, then adding 0.1% to 0.5% of sodium methoxide or sodium formate, or not adding any catalyst, after finishing adding, heating to 50° C. to 60° C. for reaction for 5 hours to 8 hours, continuously heating to 80° C. to 120° C. for reaction for 48 hours to 72 hours, and monitoring the reaction process by TLC until the reaction is complete; and removing the catalyst, adding ethanol or methanol containing 5% to 10% of water for recrystallizing, filtering to yield a white powder solid product, and drying, wherein a yield ranges from 83% to 92%; a preparation method of the structural general formula 6: (1) under the protection of nitrogen, adding methyl acrylate or methyl methacrylate into a reaction flask, starting stirring, then adding 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF, or not adding any solvent, then adding 100 ppm to 1000 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol, cooling to 10° C. to 20° C., and then dropwise adding alkyl cyclic diamine slowly; heating to a room temperature after dropwise adding, stirring for 5 hours to 8 hours, heating to 45° C. to 70° C. to continue the reaction for 10 hours to 24 hours; monitoring the reaction process by TLC until the reaction is complete, removing excessive methyl acrylate under vacuum, and using the remaining reaction intermediate without further purification for next reaction: (2) under the protection of nitrogen and stirring, adding pentanediamine, or hexamethylene diamine, or decanediamine, or hexanediol, or octanediol, or decanediol in batches first into the intermediate obtained in the first step at a room temperature, then adding 0.01% to 5% of sodium methoxide or sodium formate, or not adding any catalyst, or diethyl tin oxide, or aluminum alkoxide, after finishing adding, heating to 50° C. to 70° C. for reaction for 5 hours to 8 hours, continuously heating to 80° C. to 130° C. for reaction for 48 hours to 96 hours, and monitoring the reaction process by TLC until the reaction is complete; and removing the catalyst, adding ethanol or methanol containing 5% to 10% of water for recrystallizing, filtering to yield a white powder solid product, and drying, wherein a yield ranges from 83% to 91%; and a preparation method of the structural general formula 7: (1) under the protection of nitrogen and stirring, adding alkylamine, or aryl substituted alkylamine, or hydroxylamine, or alkoxyamine, or aryl substituted alkoxyamine into a reaction flask, then adding 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF, or not adding any solvent, then adding 100 ppm to 1000 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol, or 0.1% to 5% of NaOH, or K2CO3, or 10% to 30% of silica gel, or acidic alumina, or not adding any catalyst, cooling to 5° C. to 10° C., and then dropwise adding methyl acrylate or methyl methacrylate slowly; heating to a room temperature after dropwise adding, stirring for 5 hours to 18 hours, heating to 30° C. to 70° C. to continue the reaction for 5 hours to 24 hours; monitoring the reaction process by TLC until the reaction is complete, removing excessive methyl acrylate, solvent and catalyst under vacuum, and using the remaining reaction intermediate without further purification for next reaction; (2) under the protection of nitrogen and stirring, adding pentanediamine, or hexamethylene diamine, or decanediamine, or hexanediol, or octanediol, or decanediol in batches first into the intermediate obtained in the first step at a room temperature, then adding 0.01% to 5% of sodium methoxide or sodium formate, or not adding any catalyst, or diethyl tin oxide, or aluminum alkoxide, after finishing adding, heating to 50° C. to 70° C. for reaction for 10 hours to 18 hours, continuously heating to 80° C. to 140° C. for reaction for 24 hours to 96 hours, and monitoring the reaction process by TLC until the reaction is complete; and removing the catalyst, adding ethanol, or methanol, or ethyl acetate, or petroleum ether containing 5% to 10% of water for recrystallizing, filtering to yield a white powder solid product, and drying, wherein a yield ranges from 80% to 90%.

4. An application of the structure of the steric hindrance adjustable weak base light stabilizer according to claim 1 to a so-called polymer material to provide effective light stability protection and antioxidant stability protection.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0116] FIG. 1 shows comparison of results of thermal and light aging of 1PP-T20 splines (note: (1) splines in upper row are results of thermal aging in oven at 150° C. for 192 hours, and splines in lower row are results of UVB ultraviolet light aging at 70° C. for 157 hours; (2) testing and comparison of standard samples: B1 is 3853. B2 is 770, and B3 is 622; and (3) B4 to B13 are innovative antioxidants and steric hindrance adjustable light stabilizers of the patent).

[0117] FIG. 2 shows comparison of results of thermal and light aging of ABS splines (note: (1) splines in upper row are results of thermal aging in oven at 110° C. for 178 hours, and splines in lower row are results of UVB light aging at 70° C. for 113 hours; (2) testing and comparison of standard samples: C1 is 3853, C2 is 770, and C3 is 622; and (3) C4 to C12 are innovative antioxidants and steric hindrance adjustable light stabilizers of Rycom).

[0118] FIG. 3 shows results 1 of UVB ultraviolet light aging at 70° C. for 47 hours of PC sample plates (antioxidant AO+light stabilizer (2: 1): 0.1%; and UV aging test device Q-Lab).

[0119] FIG. 4 shows results 2 of UVB ultraviolet light aging at 70° C. for 17 hours of PC sample plates ((1) sample plates in upper row are results of thermal aging in oven at 150° C. for 17 hours, and sample plates in lower row are results of UVB light aging at 70° C. for 48 hours; (2) test and comparison of standard samples: C3 is 622, and C5 is 2020; (3) C1, C2 and C4 are innovative antioxidants and steric hindrance adjustable light stabilizers of Rycom; and (4) UVB light aging test device is Q-Lab UV light aging tester Suzhou Guangjun ZN-PB).

[0120] FIG. 5 shows results 3 of UVB ultraviolet light aging at 70° C. of PC sample plates (note: (1) PC sample plates in lower row are PC sample plates before aging; (2) PC sample plates in upper row are sample plates subject to UVB ultraviolet light aging at 70° C. for 24 hours; and (3) comparison of standard samples: UV2020(#3) and UV119(#1)).

DETAILED DESCRIPTION

[0121]

TABLE-US-00001 TABLE 1 Example structure of steric hindrance adjustable innovative weak base light stabilizer Mass spectrometry device: Thermo Finnigan LCQ Advantage ThermoFisher NMR device: Avance III 400 MHz Bruker in Switzerland MS (ESI) .sup.1H-NMR/m.p. Serial Theoretical Detection (° C.) No. Chemical structural formula value value 400 MHz 1 [00033] 338 MS.sup.+: 339.23 MS.sup.-: 337.25 N/A MP: 52° C. to 57° C. 2 [00034] 422 MS.sup.+: 445.21; 867.16 N/A Mp: 91° C. to 96° C. 3 [00035] 422 MS+: 425.3 849.09 Solvent: CDCl.sub.3 7.87 (s, 1H), 3.22 (q, J = 6.5 Hz, 1H), 2.86 (t, J = 5.3 Hz, 1H), 2.60 (t, J = 6.9 Hz, 1H), 2.40-2.29 (m, 1H), 1.47 (d, J = 6.4 Hz, 3H), 1.27 (d, J = 10.2 Hz, 18H), 0.88 (t, J = 6.6 Hz, 3H). Mp: 67° C. to 92° C. 4 [00036] 422 MS+: 423.15 445.46 8.70 (s, 1H), 3.20 (s, 1H), 2.83 (s, 1H), 2.54 (s, 1H), 2.37 (d, J = 4.4 Hz, 1H), 1.91 (s, 1H), 1.54 (dd, J = 99.5, 42.2 Hz, 5H), 0.90 (s, 2H). Mp: 79° C. to 83° C. 5 [00037] 452 MS.sup.+; 453.37 N/A Mp: 65° C. to 69° C. 6 [00038] 538 MS.sup.+: 539.43 N/A Mp: 103° C. to 109° C. 7 [00039] 482 MS+: 483.32, 987.21 MS−: 481.38 N/A Mp: 105° C. to 110° C. 8 [00040] 520 MS+: 521.30 MS−: 519.42 7.48 (d, J = 114.0 Hz, 1H), 7.31 (d, J = 9.0 Hz, 2H), 3.56 (s, 1H), 3.09 (dd, J = 13.4, 6.6 Hz, 1H), 2.72 (s, 1H), 2.43 (d, J = 5.6 Hz, 1H), 1.42 (s, 1H), 1.27 (s, 3H), 0.88 (t, J = 6.8 Hz, 1H). Mp: 154° C. to 161° C. 9 [00041] 618 MS+: 619.35, 641.44 MS−: 617.24 7.63 (t, J = 5.4 Hz, 1H), 7.32 (ddd, J = 11.7, 7.3, 1.4 Hz, 2H), 3.56 (s, 2H), 3.10 (dd, J = 13.7, 6.5 Hz, 1H), 2.76-2.67 (m, 1H), 2.42 (t, J = 5.9 Hz, 1H), 1.53-1.24 (m, 2H). Mp: 119° C. to 122° C. 10 [00042] 424 MS+: 425.24 N/A Mp: 47° C. to 70° C. 11 [00043] 426 MS+: 427.38 MS−: 425.37 N/A Mp: 39° C. to 45° C. 12 [00044] 410 MS+: 411.23 MS−: 409.15 (CD3OD) δ 3.75- 3.67 (m, 6H), 3.19 (td, J = 7.0, 2.9 Hz, 4H), 2.86 (t, J = 6.8 Hz, 1H), 2.64 (dt, J = 24.9, 7.2 Hz, 4H), 2.52 (d, J = 4.3 Hz, 6H), 2.40 (t, J = 7.1 Hz, 4H), 1.33 (d, J = 10.8 Hz, 47H), 0.93 (t, J = 6.9 Hz, 7H). Mp: 75° C. to 79° C. 13 [00045] 398 MS+: 399.08 421.11 MS−: 397.23 (CD3OD) 8.04 (s, 2H), 4.22-4.02 (m, 4H), 3.81-3.60 (m, 8H), 3.24 (d, J = 5.1 Hz, 4H), 2.75-2.32 (m, 4H), 2.01 (d, J = 25.8 Hz, 8H), 1.44-1.08 (m, 8H). Mp: 123° C. to 151° C. 14 [00046] 504 MS+: 505.30 N/A Mp: 58° C. to 61° C. 15 [00047] 586 MS+ 587.44 MS−: 585.47 N/A Mp: 97° C. to 101° C. 16 [00048] 344 MS+: 345.16 MS−: 344.23 (CD3OD) 7.86 (s, 1H), 3.22 (dd, J = 13.0, 6.6 Hz, 1H), 2.91-2.81 (m, 1H), 2.66-2.57 (m, 1H), 2.40-2.30 (m, 1H), 1.47 (d, J = 6.7 Hz, 2H), 1.27 (d, J = 10.4 Hz, 18H), 0.88 (t, J = 6.7 Hz, 3H). Mp: 112° C. to 116° C. 17 [00049] 434 MS+: 457.4 MS−: 433.21 (CD3OD) 3.64 (s, 2H), 3.49 (d, J = 1.5 Hz, 8H), 3.23 (s, 8H), 2.81 (s, 4H), 2.64 (s, 2H), 2.36 (s, 4H), 1.55 (d, J = 32.2 Hz, 8H). Mp: 147° C. to 151° C. 18 [00050] 564 MS.sup.+: 565.42 MS.sup.-: 563.48 N/A Mp: 138° C. to 146° C. 19 [00051] 732 MS+: 733.11 MS−: 731.42 N/A Mp: 137° C. to 142° C. 19 [00052] 551 MS.sup.+: 552.40 MS.sup.-: 550.28; 551.31 (CDCl3) 7.85 (s, 2H), 3.22 (dd, J = 12.7, 7.0 Hz, 4H), 2.90-2.83 (m, 4H), 2.61 (t, J = 7.1 Hz, 4H), 2.39-2.31 (m, 4H), 1.48 (dd, J = 13.6, 6.8 Hz, 2H), 1.36-1.17 (m, 40H), 0.88 (t, J = 6.8 Hz, 9H). Mp: 102° C. to 105° C. 20 [00053] 711 MS+: 712.33 (CDCl3) 7.85 (s, 2H), 4.13 (dd, J = 12.7, 7.0 Hz, 4H), 3.11-2.83 (m, 6H), 2.71 (t, J = 7.1 Hz, 4H), 2.39-2.31 (m, 4H), 1.48 (dd, J = 13.6, 6.8 Hz, 2H), 1.36-1.17 (m, 68H), 0.88 (t, J = 6.8 Hz, 12H). Mp: 86° C. to 89° C. 21 [00054] 436 MS+: 437.13 MS−: 435.41 7.78 (s, 1H), 3.22 (dd, J = 12.7, 7.0 Hz, 1H), 2.94-2.85 (m, 1H), 2.64 (t, J = 7.0 Hz, 1H), 2.41 (d, J = 5.0 Hz, 1H), 1.57-1.42 (m, 2H), 1.38-1.18 (m, 18H), 0.88 (t, J = 6.8 Hz, 3H). Mp: 77° C. to 81° C. 22 [00055] 450 MS+: 451.36, 923.24 N/A Mp: 103° C. to 107° C. 23 [00056] 745 MS+: 746.25 MS−: 744.43 N/A Mp: 102° C. to 106° C. 24 [00057] 622 MS.sup.+: 623.42 MS.sup.-: 621.38 N/A Mp: 108° C. to 110° C. 25 [00058] 594 MS.sup.-: 593.24 N/A Mp: 117° C. to 120° C. 26 [00059] 700 MS.sup.+: 701.63 N/A Mp: 59° C. to 63° C. 27 [00060] 790 MS.sup.+: 791.33 MS.sup.-: 789.48 N/A Mp: 91° C. to 96° C. 28 [00061] 513 MS+: 514.32 N/A Mp: 125° C. to 131° C. 29 [00062] 511 MS+: 512.15 MS−: 510.32 N/A Mp: 131° C. to 142° C. 30 [00063] 679 MS+: 680.13 MS−: 678.36 N/A Mp: 131° C. to 145° C. 31 [00064] 566 MS+: 567.47 N/A Mp: 68° C. to 93° C. 32 [00065] 420 MS+: 421.24 N/A Mp: 67° C. to 71° C. 33 [00066] 418 MS+: 419.21 MS−: 417.11 N/A Mp: 97° C. to 101° C. 34 [00067] 703 MS+ MS−: N/A Mp: 83° C. to 86° C. 35 [00068] 445 MS+: 446.52 N/A Liquid 36 [00069] 582 MS+: 583.30; 605.20 N/A Liquid 37 [00070] 271 MS+: 272.21 7.27 (S, CDCl3), 4.05-4.25 (dd, 2H), 3.62-3.85 (dd, 3H), 2.31-2.48 (m, 6H), 2.23 (d, 3H), 1.69-1.82 (m, 2H), 0.81-0.93 (dd, 12H) Liquid 38 [00071] 428 MS+: 429.17 N/A Liquid 39 [00072] 400 MS+: 801.35 MS−: 422.84 N/A Liquid 40 [00073] 372 MS+: 373.11 N/A Liquid 41 [00074] 372 MS+: 373.06 N/A Liquid 42 [00075] 803 MS+: 827.16 N/A Liquid 43 [00076] 595 MS−: 594.86 Liquid 44 [00077] 603 MS−: 625.08 622.69 N/A Liquid 45 [00078] 625 MS+: 626.32 N/A Liquid 46 [00079] 413 MS+: 425.24 N/A Liquid 47 [00080] 391 MS+ 7.27-7.38 (m, 5H), 7.26 (S, CDCl.sub.3) 6.11 (d, 2H), 5.59 (d, 2H), 4.16-4.23 (m, 2H), 3.81-4.16 (m, 4H), 3.62-3.81 (m, 4H), 2.72-2.89 (m, 4H), 1.86-2.03 (dd, 6H) Liquid 48 [00081] 505 MS+: 506.13; 528.29 7.27 (S, CHCl3), 6.15-6.21 (d, 2H), 5.03-5.16 (d, 2H), 4.48 (m, 1H), 3.28-4.23 (m, 10H), 2.48-3.60 (m, 8H), 1.61-1.78 (m, 9H), 1.16-1.23 (m, 10H) Liquid 49 [00082] 473 MS+: 474.45 N/A Liquid 50 [00083] 359 MS+: 360.47 N/A Liquid 51 [00084] 381 MS+: 382.32 N/A Mp: 75° C. to 79° C. 52 [00085] N/A N/A 8.01 (BS, 1H), 7.27 (s, CDCl3), 4.13 (t, 4H) 3.22 (d, 6H), 2.26-2.8 (m, 10H), 1.42-1.71 (m, 4H), 1.26-1.39 (m, 4H). Mp: 147° C. to 279° C. 53 [00086] N/A N/A 7.26 (s, CDCl3), 3.67-3.81 (m, 8H), 2.69 (t, 4H), 2.36-2.58 (m, 10H), 1.59-1.63 (m, 4H), 41.36-1.46 (m, 4H) Mp: 177° C. to 229° C. 54 [00087] N/A N/A 7.91 (BS, 2H), 7.27 (s, CDCl3), 3.13-3.31 (d, 10H), 2.39-2.23 (m, 8H), 1.42-1.71 (m, 8H), 1.26-1.39 (m, 5H). Mp: 173° C. to 196° C. 55 [00088] N/A N/A 7.26 (s, CDCl3), 4.17 (t, 4H), 2.69 (t, 4H), 2.87-3.13 (m, 6H) 2.26-2.39 (m, 8H), 1.39-1.53 (m, 6H), 0.98-1.26 (m, 5H) Mp: 169° C. to 212° C. 56 [00089] N/A N/A 7.26 (s, CDCl3), 4.34 (SB, 1H), 4.17 (t, 4H), 3.39 (t, 4H), 2.36-2.58 (m, 4H), 1.59-1.63 (m, 4H), 1.09-1.37 (m, 4H) Mp: 33° C. to 46° C. 57 [00090] N/A N/A 8.08 (SB, 2H), 7.26 (s, CDCl3), 4.53 (SB, 2H) 3.42 (d, 4H), 2.26-2.8 (m, 12H), 1.42-1.71 (m, 4H), 1.06-1.29 (m, 4H). Mp: 169° C. to 297° C. 58 [00091] 358 MS+: 359.31 (CDCl3) 8.03 (d, J = 8.3 Hz, 1H), 7.69 (d, J = 8.4 Hz, 1H), 7.51 (t, J = 7.6 Hz, 1H), 7.39 (t, J = 7.6 Hz, 1H), 4.97 (t, J = 6.4 Hz, 2H), 3.10 (dd, J = 12.2, 7.0 Hz, 2H), 2.96 (t, J = 6.4 Hz, 2H), 1.34- 0.95 (m, 19H), 0.88 (t, J = 6.9 Hz, 3H). Mp: 106° C. to 110° C. 59 [00092] 462 MS+: 463.21 485.27 (CDCl3) 8.04-7.96 (m, 1H), 7.86-7.80 (m, 1H), 7.69 (s, 1H), 7.50 (s, 1H), 7.38 (dd, J = 6.6, 3.1 Hz, 2H), 5.08 (t, J = 6.7 Hz, 1H), 4.99 (s, 2H), 3.06 (ddd, J = 31.6, 25.5, 6.4 Hz, 7H), 1.79 (s, 6H), 1.37-0.91 (m, 6H). Mp: 157° C. to 162° C. 60 [00093] 372 MS+: 373.24 767.10 CDCl3) 7.77 (s, 1H), 7.54 (d, J = 8.6 Hz, 1H), 7.34-7.30 (m, 1H), 4.96-4.90 (m, 1H), 3.10 (dd, J = 13.0, 7.0 Hz, 1H), 2.92 (dd, J = 8.2, 4.7 Hz, 1H), 2.51 (s, 1H), 1.37- 1.03 (m, 11H), 0.89 (t, J = 6.9 Hz, 3H). Mp: 84° C. to 114° C. 61 [00094] 490 MS+: 491.31; 980.11; 1003.20 N/A Mp: 145° C. to 181° C. 62 [00095] 482 MS+: 483.23 MS−: 481.11 (MeOD) δ 8.58 (s, 1H), 3.63 (q, J = 7.0 Hz, 1H), 3.34 (dt, J = 3.3, 1.6 Hz, 1H), 3.19 (t, J = 7.0 Hz, 1H), 2.93-2.70 (m, 2H), 2.47 (tdd, J = 16.2, 10.9, 5.7 Hz, 3H), 2.35 (t, J = 7.1 Hz, 1H), 1.70-1.25 (m, 8H), 1.04-0.89 (m, 4H). Mp: 81° C. to 87° C. 63 [00096] 424 MS+: 425.30, 870.99 MS−: 423.26 N/A Mp: 133° C. to 138° C. 64 [00097] 339 MS+: 340.22, 701.09 N/A Mp: 74° C. to 78° C. 65 [00098] 437 MS+: 438.41 MS−: 436.11 N/A Mp: 106° C. to 109° C. 66 [00099] 452 MS+: 453.22 MS−: 451.46 N/A Mp: 149° C. to 153° C. 67 [00100] 368 MS+: 369.21 N/A Mp: 46° C. to 49° C. 68 [00101] 868 MS+: 869.32 MS−: 867.47 N/A Mp: 155° C. to 159° C. 69 [00102] 449 MS+: 450.41 MS−: 448.04 N/A Mp: 92° C. to 97° C. 70 [00103] 435 MS+: 435.41 483.37 MS−: 434.17 N/A Mp: 83° C. to 86° C. 71 [00104] 448 MS+: 449.13 MS−: 447.24 N/A Mp: 137° C. to 141° C. 72 [00105] 584 MS+: 585.19 N/A Liquid 73 [00106] 582 MS+: 583.30 N/A Liquid 74 [00107] 314 MS+: 315.26 MS−: 313.17 N/A Liquid 75 [00108] 426 MS+: 427.32 N/A Liquid 76 [00109] 445 MS+: 445.73 N/A Liquid 77 [00110] 566 MS+: 567.23 MS−: 565.21 N/A Mp: 68° C. to 76° C. 78 [00111] 790 MS+: 791.23 MS−: 789.46 N/A Mp: 151° C. to 162° C. 79 [00112] 775 MS+: 776.13 MS−: 774.36 N/A Mp: 54° C. to 61° C. 80 [00113] 672 MS+: 673.30 MS−: 671.07 N/A Mp: 146° C. to 151° C. 81 [00114] 472 MS+: 473.33 N/A Mp: 122° C. to 126° C. 82 [00115] 484 MS+: 485.41 MS−: 483.23 N/A Mp: 93° C. to 96° C. 83 [00116] 595 MS+: 596.53 N/A Mp: 91° C. to 95° C. 84 [00117] 595 MS+: 596.53 MS−: 592.11 N/A 129° C. to 136° C. 85 [00118] 410 MS+: 411.21 MS−: 409.05 N/A Mp: 43° C. to 58° C. [00119]

[0122] The chemical structural formulas of the organic compounds in Table 1 include the example structures represented by the structural general formulas of seven types of innovative light stabilizers listed above in the patent, the synthesis method is a solvent-free green chemical synthesis method, and reaction activation energy thereof is reduced through the catalyst, so that synthesis of a target product is successfully completed.

[0123] Synthesis Method of Novel Light Stabilizer:

[0124] (I) Synthesis Method of Novel Light Stabilizer with Structural General Formula 1

[0125] (1) Synthesis Route of Novel Light Stabilizer with Structural General Formula 1

##STR00120##

[0126] (2) General Synthesis Method of Structural General Formula 1

[0127] I. Under the protection of nitrogen, methyl acrylate or methyl methacrylate (2.05 mmol to 3.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or acetone, or ethyl acetate, or dichloroethane, or DMF was added, or no solvent was added, and 0.05% to 30% of catalyst 1 was added (the catalyst 1 was acetic acid, acidic alumina, silica gel, ortho-methoxyhydroquinone, 4,4′-benzophenone, m-nitrophenol, or silica gel sulfate). The temperature was reduced to 5° C. to 10° C., and then first amine (1.0 mmol to 1.5 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 3 hours to 5 hours, and heated to 40° C. to 80° C. to continue the reaction for 5 hours to 18 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0128] II. Under the protection of nitrogen and stirring, 0.1% to 5% of catalyst 2 was added into the intermediate obtained in the reaction of the first step at the room temperature (the catalyst 2 could be sodium methoxide, sodium formate, diethyl tin oxide or aluminum isooctanol), and then n-dodecylamine, or n-octadecylamine, or n-dodecanol, or n-octadecanol (2.0 mmol) was added in batches. After charging, the temperature was raised to 40° C. to 70° C. for reaction for 5 hours to 16 hours, and continuously raised to 85° C. to 120° C. for reaction for 30 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. Ethanol, or ethyl acetate or petroleum ether containing 5% to 15% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield ranged from 85% to 97%.

[0129] (3) Synthesis Method of Product Example with Structural General Formula 1

[0130] Synthesis Method of Example Structure A:

##STR00121##

[0131] I. Methyl acrylate (2.02 mmol to 3.5 mmol) was added into a three-necked round-bottomed reaction flask, and 1 part to 3 parts of methanol, or ethanol, or dichloromethane, or dichloroethane, or acetone, or acetonitrile was added, or no solvent was added. The temperature was reduced to 7° C. to 15° C., 5% to 30% (w/w) of silica gel was added and then stirred under the protection of nitrogen, and n-butylamine (1.0 mmol to 1.5 mmol) was dropwise added. The temperature was raised to the room temperature after dropwise adding, then the reagent was stirred for 5 hours to 10 hours, continuously heated to 50° C. to 70° C., stirred for 5 hours to 12 hours, and heated to 80° C. to 100° C. for reaction for 10 hours to 96 hours when necessary. After the completion of the reaction was confirmed by TLC, excessive methyl acrylate was removed under vacuum, and the reaction intermediate without further purification was directly used for a second step.

[0132] II. Under the protection of nitrogen, 0.1% to 1.0% of sodium formate or sodium methoxide or triethylamine or N,N-dimethyl pyridine was added into the reaction flask of the reaction intermediate in the first step, and then stirred, and n-octadecylamine (1.9 mmol to 2.5 mmol) was added in batches. The temperature was raised to 50° C., then the reagent was stirred for 3 hours, and continuously heated to 80° C. and stirred for 5 hours, and then continuously heated to 106° C. for reaction for 48 hours. The reaction was monitored by TLC until the reaction was complete. Petroleum ether was added for recrystallizing to yield a white powder solid, wherein a yield was 93%.

[0133] m.p. 79° C. to 80° C.

[0134] Synthesis Method of Example Structure B:

##STR00122##

[0135] I. Methyl acrylate (2.0 mmol to 3.5 mmol) was added into a three-necked round-bottomed reaction flask, and 1 part to 3 parts of methanol, or ethanol, or acetone, or dichloroethane, or acetonitrile was added, or no solvent was added. The temperature was reduced to 10° C. to 30° C. 200 ppm to 1000 ppm hydroquinone benzophenone, or m-nitrophenol, or ortho-methoxyhydroquinone was added, and then stirred under the protection of nitrogen, and cyclohexane (1.0 mmol to 1.5 mmol) was dropwise added. The temperature was raised to the room temperature after dropwise adding, then the reagent was stirred for 5 hours to 10 hours, continuously heated to 40° C. to 70° C., stirred for 5 hours to 12 hours, and heated to 80° C. to 100° C. for reaction for 10 hours to 48 hours when necessary. After the completion of the reaction was confirmed by TLC, excessive methyl acrylate was removed under vacuum, and the reaction intermediate without further purification was directly used for a second step.

[0136] II. Under the protection of nitrogen, 0.1% to 5% of sodium formate or sodium methoxide or a phosphorous ester ligand complex of Lewis acid tin or zinc was added into the reaction flask of the reaction intermediate in the first step, and then stirred, and n-octadecylamine (1.90 mmol to 2.5 mmol) was added in batches. The temperature was raised to 50° C., then the reagent was stirred for 5 hours, and continuously heated to 80° C. and stirred for 5 hours, and then continuously heated to 100° C. to 130° C. for reaction for 48 hours. The reaction was monitored by TLC until the reaction was complete. Petroleum ether was added for recrystallizing to yield a white powder solid, wherein a yield was 95%.

[0137] m.p. 79° C. to 83° C., MS: 1H NMR:

[0138] Synthesis Method of Example Structure C:

##STR00123##

[0139] I. Methyl acrylate (2.05 mmol to 3.5 mmol) was added into a three-necked round-bottomed reaction flask, and ethanol, or acetone, or methanol, or acetonitrile, or dichloromethane was added, or no solvent was added. The reagent was stirred under the protection of nitrogen, the temperature was reduced to 10° C. to 20° C., 200 ppm to 1500 ppm o-methoxyhydroquinone or 4,4-diphenol hydroxybenzophenone was added, and 2-iisopropylaminoethylamine (1.0 mmol to 1.5 mmol) was dropwise added. The temperature was raised to the room temperature after dropwise adding, then the reagent was stirred for 5 hours to 10 hours, continuously heated to 50° C. to 70° C., stirred for 5 hours to 12 hours, and heated to 80° C. to 100° C. when necessary. The completion of the reaction was confirmed by TLC. Excessive methyl acrylate was removed under vacuum, and the reaction intermediate without further purification was directly used for a second step.

[0140] II. The reagent was stirred, and under the protection of nitrogen, n-octadecylamine (1.90 mmol to 2.5 mmol) was added in batches into the reaction flask of the reaction intermediate in the first step. The temperature was raised to 70° C., then the reagent was stirred for 5 hours, and continuously heated to 85° C. and stirred for 5 hours, and then continuously heated to 100° C. to 130° C. for reaction for 48 hours to 96 hours. The reaction was monitored by TLC until the reaction was complete. Petroleum ether was added for recrystallizing to yield a white powder solid, wherein a yield was 91.5%.

[0141] m.p.: 74° C. to 77° C.

[0142] Synthesis Method of Example Structure D:

##STR00124##

[0143] The first step of the synthesis method and the second step of the synthesis method are the same as those above.

[0144] A yield was 90.6%, m.p.:

[0145] Synthesis Method of Example Structure E:

##STR00125##

[0146] I. Under stirring and the protection of nitrogen, methyl acrylate (2.0 mmol to 3.5 mmol) was added into a three-necked round-bottomed reaction flask, and then ethanol, or acetone, or methanol, or dichloroethane was added, or no solvent was added. The temperature was reduced to 6° C. to 15° C., 10% to 30% (400 mesh) of silica gel was added and then stirred under the protection of nitrogen, and KH550 (1.0 mmol to 1.6 mmol) was dropwise added. The temperature was raised to the room temperature after dropwise adding, and then the reagent was stirred for 5 hours to 7 hours, continuously heated to 50° C. to 70° C., and stirred for 10 hours to 36 hours. The completion of the reaction was confirmed by TLC. Excessive methyl acrylate was removed under vacuum, and the reaction intermediate without further purification was directly used for a second step.

[0147] II. The reagent was stirred, and under the protection of nitrogen, n-octadecylamine (1.9 mmol to 2.5 mmol) was added in batches into the reaction flask of the reaction intermediate in the first step. The temperature was raised to 60° C., then the reagent was stirred for 5 hours, and continuously heated to 80° C. and stirred for 5 hours, and then continuously heated to 100° C. to 140° C. for reaction for 48 hours to 96 hours. The reaction was monitored by TLC until the reaction was complete. Silica gel was filtered, and petroleum ether was recrystallized to yield a white powder solid, wherein a yield was 90.1%.

[0148] m.p.: 67° C. to 70° C.

[0149] Synthesis Method of Example Structure F:

##STR00126##

[0150] I. Under stirring and the protection of nitrogen, hydroxylamine sulfate or hydroxylamine hydrochloride (1.0 mmol to 1.3 mmol) was dissolved in water, methyl acrylate or ethyl acrylate (1.3 mmol to 3.5 mmol) dissolved in ethyl acetate, or dichloroethane, or dichloromethane, or ethanol, or methanol, or acetonitrile (1 part to 5 parts) or having no solvent was added, 0.1% to 5% of phase transfer catalyst tetrabutylammonium chloride, or tetrabutylammonium bromide, or 18-crown-6, or 15-crown-5, or glycol ether was added, and sodium hydroxide, or potassium hydroxide, or potassium carbonate (1.0 mmol to 3.0 mmol) was dropwise added, stirred at the room temperature for 1 hour to 5 hours, and heated to 28° C. to 50° C. to continue the reaction for 2 hours to 6 hours. The reaction process was monitored by TLC until the reaction of hydroxylamine was complete. The reagent was extracted with ethyl acetate, or dichloromethane, or dichloroethane, or methyl butyl ether, dried, and filtered to remove the solvent, and the solid without further purification was directly used in next step.

[0151] II. The reagent was stirred, and under the protection of nitrogen, n-octadecylamine (1.9 mmol to 2.5 mmol) was added in batches into the reaction flask of the reaction intermediate in the first step. The temperature was raised to 50° C. to 60° C., then the reagent was stirred for 5 hours, and continuously heated to 70° C. to 90° C. and stirred for 15 hours to 32 hours, and then continuously heated to 95° C. to 140° C. for reaction for 48 hours to 96 hours. The reaction was monitored by TLC until the reaction was complete. Ethanol or methanol containing 3% to 15% of water was recrystallized to yield a white powder solid, wherein a yield was 87.9%.

[0152] m.p.: 97° C. to 99° C.

[0153] (II) Synthesis Method of Novel Light Stabilizer with Structural General Formula 2

[0154] (1) Synthesis Route of Novel Light Stabilizer with Structural General Formula 2

##STR00127##

[0155] (2) General Synthesis Method of Structural General Formula 2

[0156] I. Under the protection of nitrogen, methyl acrylate or methyl methacrylate (1.05 mmol to 3.3 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and 0.02% to 30% of catalyst 1 was added (the catalyst 1 was acetic acid, acidic alumina, silica gel, ortho-methoxyhydroquinone, 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol). The temperature was reduced to 5° C. to 10° C., and then second amine (1.0 mmol to 1.5 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, and then the reagent was stirred for 6 hours to 24 hours, and if the reaction needs to be continued, the reagent was heated to 40° C. to 80° C. to continue the reaction for 5 hours to 18 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0157] II. Under the protection of nitrogen and stirring, 0.1% to 5% of catalyst 2 was added into the intermediate obtained in the reaction of the first step at the room temperature (the catalyst 2 could be sodium methoxide, sodium formate, diethyl tin oxide or aluminum isooctanol), and then n-dodecylamine, or n-hexadecylamine, or n-octadecylamine, or n-dodecanol, or n-octadecanol (0.9 mmol to 1.2 mmol) was added in batches. After charging, the temperature was raised to 40° C. to 70° C. for reaction for 8 hours to 16 hours, and continuously raised to 85° C. to 140° C. for reaction for 48 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol, or methanol, or ethyl acetate, or petroleum ether containing 0.5% to 20% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield ranged from 87% to 96%.

[0158] (3) Synthesis Method of Product Example with Structural General Formula 2

[0159] Synthesis Method of Example Structure A:

##STR00128##

[0160] I. Under the protection of nitrogen, methyl acrylate (1.05 mmol to 3.3 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and 100 ppm to 1000 ppm catalyst o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol was added. The temperature was reduced to 10° C. to 15° C., and then 4-methylpiperidine amine (0.9 mmol to 1.5 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 10 hours to 20 hours, and heated to 40° C. to 50° C. to continue the reaction for 5 hours to 7 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was directly used for next reaction.

[0161] II. Under the protection of nitrogen and stirring, 0.1% to 1% of sodium methoxide or sodium formate was added into the intermediate obtained in the reaction of the first step at the room temperature, and then n-octadecylamine (0.9 mmol to 1.2 mmol) was added in batches. After charging, the temperature was raised to 50° C. to 70° C. for reaction for 12 hours to 18 hours, and continuously raised to 85° C. to 140° C. for reaction for 48 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol or methanol containing 5% of water was added for recrystallizing to yield a white powder solid product, and dried, wherein a yield was 91.2%.

[0162] m.p.

[0163] Synthesis Method of Example Structure B:

##STR00129##

[0164] I. Under the protection of nitrogen, methyl acrylate (1.3 mmol to 3.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and 30% silica gel (400 mesh) was added. The temperature was reduced to 15° C. to 20° C., and then diisobutylamine (0.9 mmol to 1.5 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 15 hours to 20 hours, and heated to 40° C. to 50° C. to continue the reaction for 3 hours to 5 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was directly used for next reaction.

[0165] II. Under the protection of nitrogen and stirring, 0.1% to 1% of sodium methoxide or sodium formate was added into the intermediate obtained in the reaction of the first step at the room temperature, and then n-octadecylamine (0.9 mmol to 1.2 mmol) was added in batches. After charging, the temperature was raised to 60° C. to 70° C. for reaction for 10 hours to 13 hours, and continuously raised to 80° C. to 140° C. for reaction for 48 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, petroleum ether containing 0.5% of water was added for recrystallizing to yield a white powder solid product, and dried, wherein a yield was 89.3%.

[0166] m.p. 79° C. to 81° C.

[0167] Synthesis Method of Example Structure C:

##STR00130##

[0168] I. Under the protection of nitrogen, methyl acrylate (1.3 mmol to 3.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and 300 ppm to 700 ppm 4,4′-diphenol hydroxybenzophenone was added. The temperature was reduced to 10° C. to 15° C., and then dibenzyl amine (0.9 mmol to 1.5 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 18 hours to 20 hours, and heated to 50° C. to 60° C. to continue the reaction for 5 hours to 7 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was directly used for next reaction.

[0169] II. Under the protection of nitrogen and stirring, 0.1% to 1% of sodium methoxide or sodium formate was added into the intermediate obtained in the reaction of the first step at the room temperature or no catalyst was added, and then n-octadecylamine (0.9 mmol to 1.2 mmol) was added in batches. After charging, the temperature was raised to 50° C. to 70° C. for reaction for 15 hours to 18 hours, and continuously raised to 85° C. to 140° C. for reaction for 24 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol containing 5% of water was added for recrystallizing to yield a white powder solid product, and dried, wherein a yield was 92%.

[0170] m.p. 140° C. to 143° C.

[0171] Synthesis Method of Example Structure D:

##STR00131##

[0172] I. Under the protection of nitrogen, methyl acrylate (1.3 mmol to 3.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and 200 ppm to 600 ppm 4,4′-diphenol hydroxybenzophenone or o-methoxyhydroquinone was added. The temperature was reduced to 150 to 18° C., and then methylcyclohexylamine (0.95 mmol to 1.2 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 15 hours to 20 hours, and heated to 500 to 6010 to continue the reaction for 2 hours to 3 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was directly used for next reaction.

[0173] II. Under the protection of nitrogen and stirring, 0.1% to 1% of sodium methoxide or sodium formate was added into the intermediate obtained in the reaction of the first step at the room temperature or no catalyst was added, and then n-octadecylamine (0.95 mmol to 1.0 mmol) was added in batches. After charging, the temperature was raised to 50° C. to 60.0 for reaction for 5 hours to 8 hours, and continuously raised to 85° C. to 1400 for reaction for 24 hours to 72 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol containing 5% to 10% of water was added for recrystallizing to yield a white powder solid product, and dried, wherein a yield was 87%.

[0174] m.p. 67° C. to 70° C.

[0175] Synthesis Method of Example Structure E:

##STR00132##

[0176] I. Under the protection of nitrogen, methyl acrylate (1.5 mmol to 3.0 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and 100 ppm to 600 ppm 4,4′-diphenol hydroxybenzophenone or o-methoxyhydroquinone was added. Morpholine (0.97 mmol to 1.3 mmol) was dropwise added slowly at a room temperature. The reagent was stirred for 18 hours to 36 hours at the room temperature (25° C.), and heated to 40° C. to 600 to continue the reaction for 3 hours to 6 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was directly used for next reaction.

[0177] II. Under the protection of nitrogen and stirring, 0.1% to 1% of sodium methoxide or sodium formate was added into the intermediate obtained in the reaction of the first step at the room temperature or no catalyst was added, and then n-octadecylamine (0.90 mmol to 1.10 mmol) was added in batches. After charging, the temperature was raised to 550 to 700 for reaction for 6 hours to 8 hours, and continuously raised to 80° C. to 1400 for reaction for 24 hours to 72 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol containing 5% of water was added for recrystallizing to yield a white powder solid product, and dried, wherein a yield was 89.3%.

[0178] m.p.

[0179] Synthesis Method of Example Structure F:

##STR00133##

[0180] I. Under the protection of nitrogen, n-butylamine (1.2 mmol to 1.5 mmol) was added into a reaction flask, 1 part to 3 parts of methanol, or ethanol, or dichloroethane, or acetonitrile was added, and then 15% to 30% of silica gel or acidic alumina or 0.03% to 0.7% of 4,4-diphenol hydroxybenzophenone or o-hydroxyhydroquinone was added. Acrylonitrile (1.0 mmol) was dropwise added at a room temperature, stirred for 2 hours to 5 hours at the room temperature after dropwise adding, and then heated to 30° C. to 65° C. to continue the reaction for 6 hours to 15 hours. The reaction process was monitored by TLC until the reaction was complete. Excessive n-butylamine was removed under vacuum, and the remaining oily matter without further purification was directly used in a second step.

[0181] II. Under the protection of nitrogen and stirring, 1 part to 3 parts of methanol, or ethyl acetate, or dichloroethane was added into the oily matter (1.0 mmol) in the above step, and then methyl acrylate (1.5 mmol to 3.0 mmol) was dropwise added into the reaction flask. The reagent was stirred for 10 hours to 36 hours at the room temperature (25° C.), and heated to 40° C. to 60° C. to continue the reaction for 5 hours to 15 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate oily matter without further purification was directly used for next reaction.

[0182] Reaction of Third Step:

[0183] Under the protection of nitrogen and stirring, 0.1% to 1% of sodium methoxide or sodium formate was added into the intermediate oily matter obtained in the reaction of the second step at the room temperature or no catalyst was added, and then n-octadecylamine (0.90 mmol to 1.10 mmol) was added in batches. After charging, the temperature was raised to 55° C. to 75° C. for reaction for 8 hours to 16 hours, and continuously raised to 800 to 140° C. for reaction for 24 hours to 72 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol containing 5% of water was added for recrystallizing to yield a white powder solid product, and dried, wherein a yield was 86.5%.

[0184] m.p.

[0185] (III) Synthesis Method of Novel Light Stabilizer with Structural General Formula 3

[0186] (1) Synthesis Route of Novel Light Stabilizer with Structural General Formula 3

##STR00134##

[0187] (2) General Synthesis Method of Structural General Formula 3

[0188] II. Under the protection of nitrogen, methyl acrylate or methyl methacrylate (2.5 mmol to 4.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or MF was added, or no solvent was added, and 0.01% to 30% of catalyst 1 was added (the catalyst 1 was acetic acid, acidic alumina, silica gel, ortho-methoxyhydroquinone, 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol). The temperature was reduced to 5° C. to 20° C., and then second amine (1.90 mmol to 2.05 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, and then the reagent was stirred for 5 hours to 24 hours, and heated to 40° C. to 80° C. if the reaction needs to continue the reaction for 5 hours to 18 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0189] II. Under the protection of nitrogen and stirring, alkyl diamine, such as ethylenediamine, or butanediamine, or hexamethylenediamine, or decanediamine (1.0 mmol to 1.2 mmol) was added in batches first into the intermediate obtained in the first step at a room temperature, and then 0.1% to 5% of catalyst 2 was added (the catalyst 2 was sodium methoxide, sodium formate, diethyl tin oxide or aluminum isooctanol). After charging, the temperature was raised to 50° C. to 70° C. for reaction for 6 hours to 16 hours, and continuously raised to 85° C. to 120° C. for reaction for 48 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol, or methanol, or ethyl acetate, or petroleum ether containing 0.5% to 20% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield ranged from 85% to 95%.

[0190] (3) Synthesis Method of Product Example with Structural General Formula 3

[0191] Synthesis Method of Example Structure A:

##STR00135##

[0192] I. Under the protection of nitrogen, methyl acrylate (2.2 mmol to 3.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and then 30% silica gel (400 mesh) was added. The temperature was reduced to 15° C. to 20° C., and then 3-methylpiperidine amine (1.95 mmol to 2.01 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 5 hours to 7 hours, and continuously heated to 40° C. to 50° C. to continue the reaction for 5 hours to 10 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0193] II. Under the protection of nitrogen and stirring, hexanediamine (1.0 mmol to 1.05 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then 0.1% of sodium methoxide or sodium formate was added. After charging, the temperature was raised to 50° C. to 60° C. for reaction for 10 hours to 15 hours, and continuously raised to 85° C. to 120° C. for reaction for 48 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, methanol, or ethyl acetate, or petroleum ether containing 0.5% to 5% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield was 83.9%.

[0194] m.p.

[0195] Synthesis Method of Example Structure B:

##STR00136##

[0196] I. Under the protection of nitrogen, methyl acrylate (2.5 mmol to 4.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and 100 ppm to 600 ppm 4,4′-diphenol hydroxybenzophenone, or o-methoxyhydroquinone, or m-nitrophenol was added. The temperature was reduced to 20° C., and then dibenzylamine (1.96 mmol to 2.03 mmol) was dropwise added slowly. The reagent was stirred for 5 hours at the room temperature after dropwise adding, and heated to 40° C. to 60° C. to continue the reaction for 10 hours to 32 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0197] II. Under the protection of nitrogen and stirring, hexanediamine (1.05 mmol to 1.15 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then 0.1% of sodium methoxide or sodium formate was added, or no catalyst was added. After charging, the temperature was raised to 50° C. to 70° C. for reaction for 8 hours to 10 hours, and continuously raised to 80° C. to 125° C. for reaction for 32 hours to 72 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol, or ethyl acetate, or petroleum ether containing 5% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield was 90.3%.

[0198] m.p. 140° C. to 143° C.

[0199] Synthesis method of example structure C:

##STR00137##

[0200] I. Under the protection of nitrogen, methyl acrylate (2.5 mmol to 3.8 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, then 200 ppm to 700 ppm 4,4′-diphenol hydroxybenzophenone, or o-methoxyhydroquinone, or m-nitrophenol, or m-nitrophenol was added, and then dibenzylamine (1.96 mmol to 2.03 mmol) was dropwise added slowly at a room temperature. The reagent was stirred for 18 hours at the room temperature after dropwise adding, and heated to 40° C. to 60° C. if necessary to continue the reaction for 5 hours to 15 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0201] II. Under the protection of nitrogen and stirring, hexanediamine (1.05 mmol to 1.15 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then 0.1% of sodium methoxide or sodium formate was added, or no catalyst was added. After charging, the temperature was raised to 50° C. to 70° C. for reaction for 6 hours to 8 hours, and continuously raised to 80° C. to 125° C. for reaction for 48 hours to 72 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol, or ethyl acetate, or petroleum ether containing 5% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield was 92.6%.

[0202] m.p. 122° C. to 125° C.

[0203] Synthesis Method of Example Structure D:

##STR00138##

[0204] I. Under the protection of nitrogen, methyl acrylate (2.80 mmol to 4.8 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, then 200 ppm to 700 ppm 4,4′-diphenol hydroxybenzophenone, or o-methoxyhydroquinone, or m-nitrophenol was added, and then diisopropylamine (1.95 mmol to 2.01 mmol) was dropwise added slowly at a room temperature. The reagent was stirred for 18 hours at the room temperature after dropwise adding, and heated to 50° C. to 60° C. to continue the reaction for 18 hours to 32 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0205] II. Under the protection of nitrogen and stirring, hexanediamine (1.05 mmol to 1.15 mmol) was added into the intermediate obtained in the reaction of the first step at the room temperature, and then 0.1% of sodium methoxide or sodium formate was added, or no catalyst was added. After charging, the temperature was raised to 60° C. to 70° C. for reaction for 8 hours to 10 hours, and continuously raised to 80° C. to 125° C. for reaction for 48 hours to 72 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethyl acetate or petroleum ether containing 0.5% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield was 86%.

[0206] m.p. 115° C. to 118° C.

[0207] Synthesis Method of Example Structure E:

##STR00139##

[0208] I. Under the protection of nitrogen, methyl acrylate (2.8 mmol to 3.8 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, then 20% of acidic alumina was added, and then bis(2-hydroxyethyl)amine (1.97 mmol to 2.0 mmol) was dropwise added slowly at a room temperature. The reagent was stirred for 5 hours at the room temperature after dropwise adding, and heated to 35° C. to 60° C. to continue the reaction for 15 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0209] II. Under the protection of nitrogen and stirring, hexanediamine (1.0 mmol to 1.1 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then 0.1% of sodium methoxide or sodium formate was added, or no catalyst was added. After charging, the temperature was raised to 50° C. to 70° C. for reaction for 6 hours to 8 hours, and continuously raised to 80° C. to 125° C. for reaction for 48 hours to 72 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol or methanol containing 5% to 10% of water was added for recrystallizing, and filtered to yield a colorless oily liquid product, and dried, wherein a yield was 95.6%.

[0210] m.p.: 147° C. to 151° C.

[0211] Synthesis Method of Example Structure F:

##STR00140##

[0212] I. Under the protection of nitrogen, methyl acrylate (2.6 mmol to 3.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and then 4,4-diphenol hydroxybenzophenone or o-methoxyhydroquinone was added or no catalyst was added. Diisobutyl amine (1.98 mmol to 2.0 mmol) was dropwise added slowly at a room temperature. The reagent was stirred for 5 hours at the room temperature after dropwise adding, and heated to 30° C. to 60° C. to continue the reaction for 15 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0213] II. Under the protection of nitrogen and stirring, hexanediamine (0.95 mmol to 1.1 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then 0.1% of sodium methoxide or sodium formate was added, or no catalyst was added. After charging, the temperature was raised to 50° C. to 70° C. for reaction for 6 hours to 8 hours, and continuously raised to 80° C. to 120° C. for reaction for 48 hours to 72 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol or methanol containing 5% to 15% of water was added for recrystallizing, and filtered to yield a white powder solid product, and dried, wherein a yield was 93.5%.

[0214] m.p. 105° C. to 107° C.

[0215] (IV) Synthesis Method of Novel Light Stabilizer with Structural General Formula 4

[0216] (1) Synthesis Route of Novel Light Stabilizer with Structural General Formula 4

##STR00141##

[0217] (2) General Synthesis Method of Structural General Formula 4

[0218] I. Under the protection of nitrogen, methyl acrylate or methyl methacrylate (2.5 mmol to 4.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and then 100 ppm to 1000 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol was added. The temperature was reduced to 5° C. to 20° C., and then second amine (0.90 mmol to 1.15 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, and then the reagent was stirred for 8 hours to 32 hours, and if the reaction needs to be continued, the reagent was heated to 40° C. to 60° C. to continue the reaction for 5 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0219] II. Under the protection of nitrogen and stirring, dodecylamine, or hexadecylamine, or octadecylamine, or hexadecanol, or octadecanol, or dodecanol (1.95 mmol to 2.20 mmol) was added in batched first into the intermediate obtained in the first step at a room temperature, and then 0.02% to 5% of catalyst 2 was added (the catalyst 2 was sodium methoxide, sodium formate, diethyl tin oxide or aluminum isooctanol). After charging, the temperature was raised to 50° C. to 70° C. for reaction for 8 hours to 10 hours, and continuously raised to 80° C. to 120° C. for reaction for 48 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol, or methanol, or ethyl acetate, or petroleum ether containing 0.5% to 20% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield ranged from 83% to 96%.

[0220] (3) Synthesis Method of Product Example with Structural General Formula 4

[0221] Synthesis Method of Example Structure A:

##STR00142##

[0222] I. Under the protection of nitrogen, methyl acrylate (2.5 mmol to 3.8 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and then 300 ppm to 700 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol was added. The temperature was reduced to 15° C. to 20° C., and then N,N′-dimethyl ethylenediamine (1.0 mmol to 1.1 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 8 hours to 10 hours, and continuously heated to 40° C. to 60° C. to continue the reaction for 10 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0223] II. Under the protection of nitrogen and stirring, octadecylamine (1.95 mmol to 2.0 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then 0.02% to 5% of sodium methoxide or sodium formate was added. After charging, the temperature was raised to 50° C. to 60° C. for reaction for 5 hours to 8 hours, and continuously raised to 80° C. to 120° C. for reaction for 48 hours to 72 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol, or methanol, or ethyl acetate, or petroleum ether containing 0.5% to 20% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield was 93%.

[0224] m.p. 90° C. to 93° C.

[0225] Synthesis Method of Example Structure B:

##STR00143##

[0226] I. Under the protection of nitrogen, glycidyl methacrylate (1.1 mmol to 1.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and then 200 ppm to 600 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol was added. The temperature was reduced to 20° C., and then N,N′-dimethyl ethylenediamine (0.95 mmol to 1.05 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 10 hours to 18 hours, and continuously heated to 40° C. to 60° C. to continue the reaction for 10 hours to 20 hours. The reaction process was monitored by TLC until the reaction was complete, and excessive epoxypropylmethyl acrylate was removed under vacuum to yield an oily product, wherein a yield was 96%.

[0227] Synthesis Method of Example Structure C:

##STR00144##

[0228] I. Under the protection of nitrogen, acrylonitrile (1.95 mmol to 1.98 mmol) was dropwise added into a reaction flask with hexamethylenediamine (1.0 mmol to 1.05 mmol), stirred for 10 hours to 18 hours at a room temperature, and heated to 40° C. to 70° C. to continue the reaction for 8 hours to 15 hours. The reaction process was monitored by TLC until the reaction was complete. Excessive hexamethylenediamine was removed to yield the oily intermediate, and the oily intermediate without further purification was directly used for a second step.

[0229] II. Under the protection of nitrogen and stirring, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or acetonitrile, or dichloromethane was added into the intermediate (0.95 mmol to 1.0 mmol) obtained in the above step, then 300 ppm to 700 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol was added, and methyl acrylate (2.6 mmol to 3.9 mmol) was dropwise added into the reaction flask. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 10 hours to 18 hours, and continuously heated to 40° C. to 70° C. to continue the reaction for 24 hours to 36 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction oily intermediate without further purification was used for next reaction.

[0230] III. Under the protection of nitrogen and stirring, octadecylamine (1.93 mmol to 1.97 mmol) was added in batched first into the oily intermediate (0.95 mmol to 1.0 mmol) obtained in the reaction of the second step at the room temperature, and then 0.02% to 5% of sodium methoxide or sodium formate was added. After charging, the temperature was raised to 50° C. to 60° C. for reaction for 5 hours to 8 hours, and continuously raised to 80° C. to 130° C. for reaction for 48 hours to 72 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol, or methanol, or ethyl acetate, or petroleum ether containing 0.5% to 20% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield was 89.6%.

[0231] m.p. 96° C. to 99° C.

[0232] (V) Synthesis Method of Novel Light Stabilizer with Structural General Formula 5

[0233] (1) Synthesis Route of Novel Light Stabilizer with Structural General Formula 5

##STR00145##

[0234] (2) General Synthesis Method of Structural General Formula 5

[0235] I. Under the protection of nitrogen, methyl acrylate or methyl methacrylate (1.5 mmol to 3.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and then 100 ppm to 1000 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol was added. The temperature was reduced to 10° C. to 20° C., and then cyclic alkyl diamine (0.90 mmol to 1.15 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 3 hours to 5 hours, and heated to 40° C. to 60° C. to continue the reaction for 10 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0236] II. Under the protection of nitrogen and stirring, octadecylamine, or dodecylamine, or hexadecylamine (1.95 mmol to 2.20 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then 0.1% to 0.5% of sodium methoxide or sodium formate was added, or no catalyst was added. After charging, the temperature was raised to 50° C. to 60° C. for reaction for 5 hours to 8 hours, and continuously raised to 80° C. to 120° C. for reaction for 48 hours to 72 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol or methanol containing 5% to 10% of water was added for recrystallizing, and filtered to yield a white powder solid product, and dried, wherein a yield ranged from 83% to 92%.

[0237] (3) Synthesis Method of Product Example with Structural General Formula 5

[0238] Synthesis Method of Example Structure A:

##STR00146##

[0239] I. Under the protection of nitrogen, methyl acrylate (1.3 mmol to 3.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and 200 ppm to 600 ppm 4,4′-diphenol hydroxy dibenzophenone or m-nitrophenol was added. The temperature was reduced to 15° C. to 20° C., and then piperazine (0.90 mmol to 1.05 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 3 hours to 5 hours, and heated to 40° C. to 60° C. to continue the reaction for 15 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0240] II. Under the protection of nitrogen and stirring, octadecylamine (2.0 mmol to 2.05 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then 0.1% to 0.5% of sodium methoxide or sodium formate was added, or no catalyst was added. After charging, the temperature was raised to 50° C. to 60° C. for reaction for 6 hours to 8 hours, and continuously raised to 80° C. to 120° C. for reaction for 48 hours to 72 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol or methanol containing 5% to 10% of water was added for recrystallizing, and filtered to yield a white powder solid product, and dried, wherein a yield was 91%.

[0241] Synthesis Method of Example Structure B:

##STR00147##

[0242] I. Under the protection of nitrogen, 3-(trimethoxysilyl)propyl acrylate (2.03 mmol to 2.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol or ethanol was added, or no solvent was added, and 100 ppm to 700 ppm 4,4′-diphenol hydroxy dibenzophenone, or m-nitrophenol, or o-methoxyhydroquinone was added. The temperature was reduced to 20° C., and then piperazine (0.95 mmol to 1.0 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 5 hours to 7 hours, and heated to 40° C. to 60° C. to continue the reaction for 24 hours to 48 hours. The reaction process was monitored by TLC until the reaction was complete, and excessive 3-(trimethoxysilyl)propyl acrylate was removed under vacuum to yield an oily product, wherein a yield was 93%.

[0243] (VI) Synthesis Method of Novel Light Stabilizer with Structural General Formula 6

[0244] (1) Synthesis Route of Novel Light Stabilizer with Structural General Formula 6

##STR00148##

[0245] (2) General Synthesis Method of Structural General Formula 6

[0246] I. Under the protection of nitrogen, methyl acrylate or methyl methacrylate (1.5 mmol to 3.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and then 100 ppm to 1000 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol was added. The temperature was reduced to 10° C. to 20° C., and then alkyl cyclic diamine (0.90 mmol to 1.15 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 5 hours to 8 hours, and heated to 45° C. to 70° C. to continue the reaction for 10 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0247] II. Under the protection of nitrogen and stirring, pentanediamine, or hexamethylenediamine, or decanediamine, or hexanediol, or octanediol, or decanediol (1.95 mmol to 2.20 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then 0.01% to 5% of sodium methoxide or sodium formate was added, or no catalyst or solvent diethyltin oxide or aluminum alkoxide was added. After charging, the temperature was raised to 50° C. to 70° C. for reaction for 5 hours to 8 hours, and continuously raised to 80° C. to 130° C. for reaction for 48 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol or methanol containing 5% to 10% of water was added for recrystallizing, and filtered to yield a white powder solid product, and dried, wherein a yield ranged from 83% to 91%.

[0248] (3) Synthesis Method of Product Example with Structural General Formula 6

[0249] Synthesis Method of Example Structure A:

##STR00149##

[0250] I. Under the protection of nitrogen, methyl acrylate (1.5 mmol to 3.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and 200 ppm to 700 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol was added. The temperature was reduced to 15° C. to 20° C., and then piperazine (0.97 mmol to 1.05 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 5 hours to 8 hours, and heated to 45° C. to 60° C. to continue the reaction for 15 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0251] II. Under the protection of nitrogen and stirring, propylene diamine, or pentanediamine, or hexamethylenediamine, or decanediamine (0.95 mmol to 1.02 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then 0.01% to 5% of sodium methoxide or sodium formate was added, or no catalyst was added. After charging, the temperature was raised to 50° C. to 60° C. for reaction for 5 hours to 6 hours, and continuously raised to 80° C. to 110 for reaction for 48 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol or methanol containing 5% to 10% of water was added for recrystallizing, and filtered to yield a white powder solid product, and dried, wherein a yield was 91%.

[0252] m.p.

[0253] Synthesis Method of Example Structure B:

##STR00150##

[0254] I. Under the protection of nitrogen, methyl acrylate (1.8 mmol to 3.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and 300 ppm to 700 ppm 4,4-diphenol hydroxy dibenzophenone or m-nitrophenol was added. The temperature was reduced to 18° C. to 20° C., and then piperazine (0.97 mmol to 1.05 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 5 hours to 6 hours, and heated to 45° C. to 60° C. to continue the reaction for 18 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0255] II. Under the protection of nitrogen and stirring, propylene glycol, or pentanediol, or hexanediol, or decanediol (0.95 mmol to 1.02 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then diethyltin oxide and aluminum alkoxide (3:1) were added as a catalyst. After charging, the temperature was raised to 80° C. to 90° C. for reaction for 5 hours to 6 hours, generated methanol micromolecules were removed by a negative pressure, and the temperature was continuously raised to 90° C. to 130° C. for reaction for 48 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol or methanol containing 5% to 10% of water was added for recrystallizing, and filtered to yield a white powder solid product, and dried, wherein a yield was 87.7%.

[0256] m.p.

[0257] (VII) Synthesis Method of Novel Light Stabilizer with Structural General Formula 7

[0258] (1) Synthesis Route of Novel Light Stabilizer with Structural General Formula 7

##STR00151##

[0259] (2) General Synthesis Method of Structural General Formula 7

[0260] I. Under the protection of nitrogen and stirring, alkylamine, or aryl substituted alkylamine, or hydroxylamine, or alkoxyamine, or aryl substituted alkoxyamine (0.90 mmol to 1.15 mmol) was added into a reaction flask, then 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and then 100 ppm to 1000 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone or m-nitrophenol, or 0.1% to 5% of NaOH or K2CO3, or 10% to 30% of silica gel or acidic alumina was added, or no catalyst was added. The temperature was reduced to 5° C. to 10° C., and then methyl acrylate or methyl methacrylate (2.1 mmol to 4.5 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 5 hours to 18 hours, and heated to 30° C. to 70° C. to continue the reaction for 5 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate, and solvent and catalyst were removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0261] II. Under the protection of nitrogen and stirring, pentanediamine, or hexamethylenediamine, or decanediamine, or hexanediol, or octanediol, or decanediol (1.95 mmol to 2.20 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then 0.01% to 5% of sodium methoxide or sodium formate was added, or no catalyst or solvent diethyltin oxide or aluminum alkoxide was added. After charging, the temperature was raised to 50° C. to 70° C. for reaction for 10 hours to 18 hours, and continuously raised to 80° C. to 140° C. for reaction for 24 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol, or methanol, or ethyl acetate, or petroleum ether containing 5% to 10% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield ranged from 80% to 90%.

[0262] (3) Synthesis Method of Product Example with Structural General Formula 7

[0263] Synthesis Method of Example Structure A:

##STR00152##

[0264] I. Under the protection of nitrogen, n-butylamine (1.5 mmol to 3.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and 100 ppm to 700 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol was added, or no catalyst was added. The temperature was reduced to 10° C. to 20° C., and then methyl acrylate (2.1 mmol to 4.0 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 10 hours to 18 hours, and heated to 35° C. to 60° C. to continue the reaction for 15 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0265] II. Under the protection of nitrogen and stirring, hexanediol (0.95 mmol to 1.02 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then dibutyltin oxide or tetrabutoxy aluminum was added. After charging, the temperature was raised to 50° C. to 80° C. for reaction for 8 hours to 12 hours, and continuously raised to 90° C. to 150V for reaction for 24 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol, or methanol, or ethanol, or methyl butyl ether, or petroleum ether containing 5% to 10% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield was 90.6%.

[0266] Synthesis Method of Example Structure B:

##STR00153##

[0267] I. Under the protection of nitrogen, n-butylamine (1.5 mmol to 3.5 mmol) was added into a reaction flask, and then stirred, 1 part to 3 parts of methanol, or ethanol, or ethyl acetate, or dichloroethane, or acetone, or acetonitrile, or DMF was added, or no solvent was added, and 100 ppm to 700 ppm o-methoxyhydroquinone, or 4,4-diphenol hydroxy dibenzophenone, or m-nitrophenol was added, or no catalyst was added. The temperature was reduced to 10° C. to 20° C., and then methyl acrylate (2.1 mmol to 4.0 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, then the reagent was stirred for 10 hours to 18 hours, and heated to 35° C. to 60° C. to continue the reaction for 15 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, excessive methyl acrylate was removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0268] II. Under the protection of nitrogen and stirring, hexanediamine (0.95 mmol to 1.02 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and then sodium formate or sodium methoxide was added. After charging, the temperature was raised to 60° C. to 80° C. for reaction for 18 hours to 24 hours, and continuously raised to 90° C. to 130° C. for reaction for 48 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol, or methanol, or ethanol, or methyl butyl ether, or petroleum ether containing 5% to 10% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield was 89.3%.

[0269] Synthesis Method of Example Structure C:

##STR00154##

[0270] I. Under the protection of nitrogen, hydroxylamine hydrochloride or hydroxylamine sulfate (1.1 mmol to 1.5 mmol) was added into a reaction flask, and stirred, then 1 part to 3 parts of methanol solution or ethanol solution (2:1) was added, then sodium hydroxide or potassium carbonate (1.2 mmol to 2 mmol) was added at 5° C. to 15° C., and then methyl acrylate (2.1 mmol to 4.0 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, and then the reagent was stirred for 15 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, ethyl acetate, or dichloromethane, or methyl butyl ether was added for extracting a target intermediate, and dried, excessive methyl acrylate and solvent were removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0271] II. Under the protection of nitrogen and stirring, hexanediamine (0.95 mmol to 1.02 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and 0.1% to 2% of sodium formate or sodium methoxide was added. After charging, the temperature was raised to 50° C. to 70° C. for reaction for 15 hours to 24 hours, and continuously raised to 70° C. to 130° C. for reaction for 72 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol, or methanol, or ethanol, or methyl butyl ether, or petroleum ether containing 5% to 10% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield was 92.5%.

[0272] Synthesis Method of Example Structure D:

##STR00155##

[0273] Reaction of First Step:

[0274] Under the protection of nitrogen and stirring, hydroxylamine hydrochloride or hydroxylamine sulfate (1.1 mmol to 1.5 mmol) was added into a reaction flask, and stirred, then 1 part to 3 parts of methanol solution or ethanol solution (2:1), or ethyl acetate, or dichloroethane was added, or no solvent was added, then sodium hydroxide or potassium carbonate (1.2 mmol to 2 mmol) or triethylamine was added at 5° C. to 15° C., and then methyl acrylate (2.0 mmol to 4.0 mmol) was dropwise added slowly. The temperature was raised to a room temperature after dropwise adding, and then the reagent was stirred for 15 hours to 24 hours. The reaction process was monitored by TLC until the reaction was complete, ethyl acetate, or dichloromethane, or methyl butyl ether was added for extracting a target intermediate, and dried, excessive methyl acrylate and solvent were removed under vacuum, and the remaining reaction intermediate without further purification was used for next reaction.

[0275] Reaction of Second Step:

[0276] Under the protection of nitrogen and stirring, hexanediol (0.98 mmol to 1.3 mmol) was added in batched first into the intermediate obtained in the reaction of the first step at the room temperature, and 0.1% to 5% of trioctyloxy aluminum and dibutyltin oxide were added. Then, the temperature was raised to 70° C. to 90° C. for reaction for 15 hours to 24 hours, and continuously raised to 100° C. to 150° C. for reaction for 48 hours to 96 hours, and the reaction process was monitored by TLC until the reaction was complete. The catalyst was removed, ethanol, or methanol, or ethanol, or methyl butyl ether, or petroleum ether containing 5% to 10% of water was added for recrystallizing, filtered to yield a white powder solid product, and dried, wherein a yield was 90.1%.

[0277] Thermal aging property tests and UVB and 300 W ultraviolet light aging property tests of the innovative light stabilizer of the patent in different polymer materials, and comparison tests with light stabilizers of common brands in the international market were carried out, and these tests were completed in PP, ABS and PC polymer materials respectively.

[0278] (1) Comparison test of thermal aging and ultraviolet light aging properties of steric hindrance adjustable light stabilizer in PP-T20

[0279] a. Twin-screw machining, extrusion and granulation

[0280] Granulation was completed by extrusion with a twin-screw extruder (Nanjing Keya AK36):

[0281] Parameters of Extruder:

[0282] Temperatures of first to tenth regions (° C.): 160, 190, 210, 220, 220, 220, 210, 210, 210, and 200

[0283] Rotating speed: 300 rpm

TABLE-US-00002 TABLE 2 Formulations of PP-T20 S.N. Ingredient 1 2 3 4 5 6 7 8 12 13 PP Z30S (Zhenhai 10 10 10 10 10 10 10 10 10 10 Refining & Chemical) PP K8003 (Yanshan 20 20 20 20 20 20 20 20 20 20 Petro-Chemical) PP K7726 (Yanshan 38 38 38 38 38 38 38 38 38 38 Petro-Chemical) POE 8411 12 12 12 12 12 12 12 12 12 12 TalC 20 20 20 20 20 20 20 20 20 20

[0284] Main antioxidant: 0.2%; (See FIG. 1 for grades)

[0285] Light stabilizer: 0.1%; (See FIG. 1 for grades)

[0286] b. Preparation of PP-T20 splines

[0287] The PP-T20 splines were completed with Haitian injection molding machine SA1200 device.

[0288] Machining parameters of injection molding machine:

[0289] Temperatures of first to fifth segments (° C.): 200, 210, 210, 205, and 190;

[0290] Injection molding pressure: 58 bar

[0291] c. Thermal aging test in oven at 150° C.

[0292] The thermal aging in oven was completed in a thermal aging oven according to a GB/T 7141-2008 plastic thermal aging test method.

[0293] d. UVB light aging test

[0294] The UVB light aging test was completed in an UVB ultraviolet light aging test box (Q-Lab Suzhou Guangjun) according to a general principle in a first part of a GB/T 16422.1-2006 plastic laboratory light source exposure test method and a fluorescent ultraviolet lamp principle in a third part of a GB/T 16422.3-2014 plastic laboratory light source exposure test method.

[0295] e. Test results of thermal aging in oven at 1500 and UVB ultraviolet light aging (FIG. 1)

[0296] f. Result discussion

[0297] It can be seen from the results of the thermal aging in oven at 1500 of the PP-T20 splines that colors of a B1 (3853) spline, a B2 (770) spline and a B3 (622) spline of products in the international market are obviously darker than those of splines (B4 to B13) added with products of the patent, wherein the spline (B2) added with the light stabilizer 770 has a deepest color, the spline added with the light stabilizer 622 has a lighter color, and the spline (B1) added with the light stabilizer 3853 has a lightest color in products of the three major international companies. In comparison, the colors of the splines (B4 to B13) added with the light stabilizers of the patent are lighter than those of the splines added with the light stabilizers in the international market.

[0298] It can be seen from the results of the VUB ultraviolet light aging test that B7 and B13 splines have a lightest color, B8 and B12 splines have a similar whiteness to those added with 3853 (B1), 770 (B2) and 622 (B3), and B4, B5 and B6 splines have a darker color.

[0299] The steric hindrance adjustable weak base light stabilizer of the patent for invention has better compatibility and matching with the polymer materials. Therefore, the steric hindrance adjustable weak base light stabilizer can not only provide better light stability protection, but also play a better role in thermal aging resistance and yellowing resistance.

[0300] Results of Mechanical Property Test

TABLE-US-00003 TABLE 3 Comparison test of tensile properties of innovative light stabilizers of Rycom in PP-T20 (Comparison samples: 3853, 770, and 622) Batch number: PPT20 RK-PT-T20201014 Aging at 150° C. 0 hour 288 hours constant constant Thermal aging in UVB temperature temperature oven at 150° C. for 288 ultraviolet UVB ultraviolet aging for and humidity and humidity hours aging for 207 207 hours 48 hours 48 hours Change hours Change Serial No. Tensile/MPa Tensile/MPa rate/MPa Retention Tensile/MPa rate/MPa Retention 1 3853 20.8 19.9 −0.9 0.96 19.3 −1.5 0.93 2 770 20.8 20.6 −0.5 0.98 19.6 −1.5 0.93 3 622 21.0 20.7 −0.7 0.97 20.2 −1.2 0.95 4 RK-AB75S 20.8 20.6 −0.4 0.98 19.6 −1.2 0.95 5 RK-AB76S 20.7 20.8 −0.2 0.99 19.4 −1.3 0.94 6 RK-AB77 20.9 20.7 −0.2 0.99 19.8 −1.1 0.96 7 RK-ABUV721 20.3 20.8 0.5 1.02 19.1 −1.2 0.94 8 RK-AB71L 20.8 20.9 0.1 1.00 19.3 −1.5 0.93 9 RK-AB78 20.9 20.6 −0.3 0.98 19.6 −1.3 0.95 10 RK-AB79 20.9 20.7 −0.4 0.98 19.7 −1.5 0.96 Change Change Serial No. Modulus/MPa Modulus/MPa value/MPa Retention Modulus/MPa value/MPa Retention 1 3853 2373 2240 −133 0.94 2720 347 1.15 2 770 2677 2390 −287 0.89 3770 1093 1.41 3 622 2503 2207 −297 0.88 1600 −903 0.64 4 RK-AB75S 2037 2020 −17 0.99 2580 543 1.27 5 RK-AB76S 2455 2440 −15 0.99 2820 365 1.15 6 RK-AB77 2340 2620 280 1.12 2350 10 1.03 7 RK-ABUV721 2490 2397 −93 0.96 1710 −780 0.69 8 RK-AB71L 2380 2260 −120 0.95 2210 −160 0.91 9 RK-AB78 2823 2630 −193 0.93 2230 −593 0.79 10 RK-AB79 2397 2440 43 1.02 2399 20 1.01 Aging at 150° C. 0 hour 288 hours constant constant UVB temperature temperature Aging at 150° C. for ultraviolet UVB ultraviolet aging for and humidity and humidity 288 hours aging for 207 207 hours 48 hours 48 hours Change hours Change Serial number Elongation/% Elongation/% value/% Retention Elongation/% value/% Retention 1 3853 3.1 2.9 −0.2 0.94 2.1 −1.0 0.68 2 770 3.0 2.8 −0.2 0.94 1.5 −1.5 0.51 3 622 2.5 2.9 0.3 1.13 1.6 −0.9 0.63 4 RK-AB75S 2.5 2.4 −0.1 0.97 2.3 −0.2 0.92 5 RK-AB76S 2.6 2.8 0.2 1.06 2.0 −0.6 0.77 6 RK-AB77 2.9 2.5 −0.4 0.86 2.0 −0.9 0.70 7 RK-ABUV721 2.8 2.8 0.0 1.01 1.9 −0.9 0.69 8 RK-AB71L 3.0 2.9 −0.2 0.95 2.1 −0.9 0.69 9 RK-AB78 3.0 2.3 −0.7 0.76 2.2 −0.8 0.73 10 RK-AB79 3.2 2.7 −0.6 0.82 2.3 −0.9 0.71

[0301] Test Condition:

[0302] Laboratory environment: temperature: 23° C., humidity: 45% RH, and state adjustment: 23° C., and 50% RH;

[0303] Executive standard: GB/T1040.2-2006/ISO 527-2: 1993;

[0304] Tensile speed: 50 mm/min

[0305] Note: the light stabilizer having an RK grade with a mantissa followed by an English letter L is a liquid antioxidant.

[0306] According to mechanical tensile data, the results of the mechanical tensile property test of the patent in Table 1 are compared with those of the products of the major international companies in the market, and the light stabilizers of some grades show an outstanding property in maintaining the mechanical property.

[0307] According to the results of comparing tensile strengths before and after thermal and light aging of the light stabilizers of some grades of the patent with those of the optimal light stabilizers 3853, 770 and 622 in PP in the market, the light stabilizers of some grades of the patent show less influence of a change in mechanical property during parallel aging, for example, tensile retention rates of RK-AB75S, RK-AB-76S, RK-AB77, RK-ABUV721, and RK-AB71L are excellent after thermal aging for 288 hours and light aging for 207 hours. According to the data, there is no obvious aging influence, and the tensile retention rates basically have no obvious change. According to the results of thermal aging, the retention rates are better than those of comparison standard samples.

[0308] In terms of moduli before and after aging and tensile elongations, the light stabilizer products of the patent show slightly better results.

[0309] (2) Comparison Test of Thermal Aging and Ultraviolet Light Aging Properties of Steric Hindrance Adjustable Light Stabilizer of the Patent in ABS

[0310] a. Twin-screw machining, extrusion and granulation

[0311] Granulation was completed by extrusion with a twin-screw extruder (Nanjing Keya AK36):

[0312] Parameters of Extruder:

[0313] Temperatures of first to tenth regions: 200, 205, 215, 215, 215, 215, 210, 210, 205, 200

[0314] Rotating speed: 300 m/s

[0315] Main antioxidant: 0.2%; light stabilizer: 0.1%

[0316] Standard comparison samples: C1 spline: 3808, C2 spline: 770, and C3 spline: 622.

[0317] b. Preparation of ABS splines

[0318] The ABS splines were completed with Haitian injection molding machine SA1200 device.

[0319] Machining Parameters of Injection Molding Machine:

[0320] Temperatures of first to fifth segments: 205, 220, 220, 215, and 200;

[0321] Injection molding pressure: 62 bar

[0322] c. Thermal aging test in oven at 110° C.

[0323] The thermal aging of all ABS splines was completed in a thermal aging oven according to a GB/T 7141-2008 plastic thermal aging test method at 110.

[0324] d. UVB light aging test

[0325] The UVB light aging test was completed in an UVB ultraviolet light aging test box (Q-Lab Suzhou Guangjun) according to a general principle in a first part of a GB/T 16422.1-2006 plastic laboratory light source exposure test method and a fluorescent ultraviolet lamp principle in a third part of a GB/T 16422.3-2014 plastic laboratory light source exposure test method.

[0326] e. Test results of thermal aging at 110° C. and UVB light aging of ABS splines (FIG. 2)

[0327] f. Result discussion

[0328] ABS is resin sensitive to yellowing caused by light aging. According to the test results of thermal aging in oven at 110° C. and UVB ultraviolet light aging of the ABS splines, a spline C7 added with the innovative light stabilizer with the grade RK-AB79 of the patent and having a main antioxidant RK-701 has the best yellowing resistance, followed by a spline C4 (added with the innovative light stabilizer RK-AB65S in the patent), and then followed by splines C9, C8 and C5. Compared with splines for the comparison test, these splines show obviously better thermal aging resistance and yellowing resistance. On the whole, the steric hindrance adjustable weak base antioxidant of the patent can still show obvious property advantages of thermal yellowing resistance and light-induced yellowing resistance in ABS sensitive to yellowing.

[0329] (3) Comparison Test of Thermal Aging and UVB Ultraviolet Light Aging Properties of the Steric Hindrance Adjustable Light Stabilizer of the Patent in PC

[0330] Preparation of Sample Plates

[0331] PC resin material: PC2805 Shanghai Covestro

[0332] PC sample plates were prepared with Haitian injection molding machine SA1200 device

[0333] Machining Parameters of PC Sample Plates

[0334] PC sample plates were prepared with Haitian injection molding machine SA1200 device

[0335] Machining parameters: temperatures of first to fifth segments (° C.) 266, 273, 273, 268, and 265

[0336] Pressure: 90 bar

[0337] Speed: 44 rpm

[0338] Aging Test of PC Sample Plates

[0339] (I) Test Results of Thermal Aging in Oven at 150° C.

TABLE-US-00004 TABLE 4 Results of thermal aging at 150° C. for four days (96 hours) of PC sample plates RRK-PT-PCT20201102 Result YI YI E L b Grade 0 hour 96 hours 96 hours 96 hours 96 hours PC-02 −3.52 −4.37 2.56 2.45 −0.71 PC-03 −4.63 −4.72 1.27 1.44 −0.11 PC-05 622 −4.86 −4.85 1.29 1.48 −0.09 PC-06 −4.63 −4.67 1.33 1.55 −0.21 PC-07 2020 −5.00 −5.04 1.70 1.69 −0.17

[0340] (II) UVB Ultraviolet Light Aging Test

[0341] Results 1 of UVB ultraviolet light aging at 70° C. for 47 hours of PC sample plates (FIG. 3)

[0342] Yellowing degrees of the PC sample plates after light aging were sorted as follows:

[0343] C2(PC-03) & C1(PC-02)<C3(622)<C5(PC-06)<C4(2020)

[0344] Results 2 of UVB ultraviolet light aging at 70° C. for 17 hours of PC sample plates (FIG. 4)

TABLE-US-00005 TABLE 5 Data of PC sample plates added with light stabilizers subject to UVB ultraviolet light aging at 70° C. for 17 hours Grade Parameter RK-PC02 RK-PC03 622 RK-PC06 2020 E 12.50 12.50 12.49 12.23 12.24 YI 14.90 14.25 13.54 13.40 13.39 L −1.22 −1.27 −1.26 −1.33 −1.34 b 11.82 11.84 11.87 11.55 11.55

[0345] Results 3 of ultraviolet light aging at 70° C. of PC sample plates (FIG. 5)

TABLE-US-00006 TABLE 6 Results of thermal aging at 150° C. for four days (96 hours) of PC sample plates RRK-PT-PCT20201104 Result YI YI E L b Grade 0 hour 23.5 hours 96 hours 96 hours 96 hours #1, 119 −5.94 15.23 14.54 −0.96 13.78 #2, PC-06 −3.95 18.14 15.32 −1.23 14.55 #3, 2020 −5.84 15.87 14.99 −1.16 14.20 #4, PC-09 −5.49 17.05 15.58 −1.43 14.79 #5, PC-10 −6.43 14.33 14.25 −1.31 13.49 #6, PC-11 −6.26 15.66 15.18 −1.54 14.39 #7, PC-07 −7.64 14.31 14.51 −1.66 14.22 oily liquid #8, PC-08 −7.81 13.24 14.38 −1.68 13.53 Oily liquid

[0346] Data results in Table 6:

[0347] Color difference: PC-10<PC-08<PC-07<UV119<UV2020<PC-11<PC-06<PC-09

[0348] YI: 13.24 (PC-08)<14.31 (PC-07)<14.33 (PC-10)<15.23 (UV119)<15.66 (PC-11)<15.87 (UV2020)<17.05 (PC-09)<18.14 (PC-06)

[0349] Result Discussion

[0350] Polycarbonate (PC) is the most sensitive material to light-induced yellowing. During thermal aging in oven at 150° C. for 4 days (96 hours) of the above PC sample plates (see Tables 4 to 6), the color differences all range from 1 to 2.6, and are no more than 3. However, the test results of UVB light aging for 4 days (96 hours) show that the color differences are obviously larger, and all range from 14 to 16. Compared with the international brands UV119 and UV2020, the light stabilizers with grades PC-10, PC-08 and PC-07 of the patent all show better light-induced yellowing resistance. It can also be seen from visual color comparison of the sample plates before and after aging in FIG. 8 that the PC sample plates of the light stabilizers with the three grades have a lighter color after light aging.

[0351] On the whole, the steric hindrance adjustable structural light stabilizer of the patent has great advantages in structural steric hindrance adjustment, an electronegative environment around the nitrogen atoms may also be adjusted, and the production process is green and easy to operate, thus providing a variety of selective products capable of reducing a cost for polymer weather-resistant products.