Polymerized high-molecular-weight sterically hindered amine and preparation method thereof

Abstract

The present invention discloses a polymerized high-molecular-weight sterically hindered amine having a general formula I, the sterically hindered amine has the advantages of high molecular weight, difficult migration in polymer products, good thermal stability, etc., and can stabilize and/or be flame retardant to organic substances sensitive to light, heat or oxidation, and furthermore, can be made to have better compatibility with different types of polymer materials by changing substituents.

##STR00001##

Claims

1. A polymerized high-molecular-weight sterically hindered amine, having a general formula I as follows: ##STR00022## wherein m.sub.n is an integer between 1-20; n is an integer between 1-20; A.sub.1, A.sub.2, A.sub.3, A.sub.4, A.sub.5 , A.sub.6 . . . A.sub.n can be the same or different, and the A.sub.1, A.sub.2, A.sub.3, A.sub.4, A.sub.5, A.sub.6 . . . A.sub.n structures are independently selected from a general formula II, III, IV or V; ##STR00023## wherein G.sub.1 and G.sub.2 can be the same or different, and are independently selected from C.sub.1—C.sub.18 alkyl, C.sub.2-C.sub.18 alkenyl, C.sub.2-C.sub.18 alkynyl, phenyl, C.sub.3-C.sub.12 cycloalkyl or C.sub.2-C.sub.12 heterocycloalkyl; or G.sub.1, G.sub.2 and the carbon atom between G.sub.1 and G.sub.2 form C.sub.3-C.sub.12 cycloalkyl, wherein any hydrogen atom on alkyl, alkenyl, alkynyl, phenyl, cycloalkyl or heterocycloalkyl can be substituted with hydroxyl, —NO.sub.2, halogen, amino, cyano, —R.sub.21, —OR.sub.21, —COOR.sub.21 or —COR.sub.21, and a hetero atom in the heterocyclic ring can be oxygen, nitrogen, sulfur, phosphorus or silicon; the R.sub.21 is selected from hydrogen, unsubstituted C.sub.1-C.sub.40 alkyl or C.sub.1-C.sub.40 alkyl with any hydrogen atom substituted with C.sub.1-C.sub.18 alkyl, unsubstituted phenyl or phenyl with any hyrogen atom substituted with 1-3 —OH or C.sub.1-30 alkyl groups, and unsubstituted C.sub.7-9 phenylalkyl or C.sub.7-9 phenylalkyl with any hydrogen atom of phenyl substituted with 1-3 —OH and C.sub.1-30 alkyl groups; E is selected from —CO— or —(CH.sub.2).sub.a—, and a is selected from 0, 1 or 2; R.sub.1 and R.sub.2 can be the same or different, and are independently selected from hydrogen, C.sub.1-C.sub.50 alkyl, C.sub.3—C.sub.12 cycloalkyl, and C.sub.2—C.sub.12 heterocycloalkyl, wherein the H atom in the alkyl, cycloalkyl, or heterocycloalkyl can be substituted with hydroxyl, —NO.sub.2, halogen, amino, cyano, —R.sub.21, —OR.sub.21, —COOR.sub.21 or —COR.sub.21, and the hetero atom in the heterocyclic ring can be oxygen, nitrogen, sulfur, phosphorus or silicon; R.sub.3 is selected from C.sub.1-C.sub.50 alkylene, C.sub.3-C.sub.12 cycloalkylene, and C.sub.2-C.sub.12 heterocycloalkylene, wherein the H atom in the alkylene, cycloalkylene, or heterocycloalkylene can be substituted with hydroxyl, NO.sub.2, halogen, amino, cyano, —R.sub.21, —OR.sub.21, —COOR.sub.21 or —COR.sub.21, and the heteroatom in the heterocyclic ring is selected from oxygen, nitrogen, sulfur, phosphorus or silicon; and, the total number of carbon atoms in R.sub.1, R.sub.2 and R.sub.3 is 50 or less; Q.sub.1 and Q.sub.2 can be the same or different, and are independently selected from —O—, —O—CO—O—, —CO—O—, —CO—NR.sub.22—, —NR.sub.22—, —NR.sub.22—CO—NR.sub.23— or —(CH.sub.2).sub.b—, and b is 0, 1 or 2; wherein the R.sub.22 and R.sub.23 are independently selected from hydrogen, unsubstituted C.sub.1-C.sub.40 alkyl or C.sub.1-C.sub.40 alkyl with any hydrogen atom substituted with C.sub.1-C.sub.18 alkyl, unsubstituted phenyl or phenyl with any hydrogen atom substituted with 1-3 —OH or C.sub.1-30 alkyl groups, and unsubstituted C.sub.7-9 phenylalkyl or C.sub.7-9 phenylalkyl with any hydrogen atom of phenyl substituted with 1-3 —OH and C.sub.1-30 alkyl groups; the structural formula of T is selected from unsubstituted alkylene or C.sub.1-C.sub.10 alkylene or C.sub.1-C.sub.10 alkylene with any H atom substituted with C.sub.1-C.sub.5 alkyl, ##STR00024## and m.sub.p is an integer between 1-20; R.sub.7 and R.sub.8 can be the same or different, and are selected from hydrogen, C.sub.1-C.sub.40 alkyl, C.sub.3-C.sub.12 cycloalkyl, and C.sub.2-C.sub.12 heterocycloalkyl, wherein the H atom in the alkyl, cycloalkyl, or heterocycloalkyl can be substituted with hydroxyl, NO.sub.2, halogen, amino, cyano, —R.sub.21, —OR.sub.21, —COOR.sub.20 or —COR.sub.21; or, R.sub.7, R.sub.8 and the N atom between R.sub.7 and R.sub.8 form C.sub.3-C.sub.12 cycloalkylene, and C.sub.2-C.sub.12 heterocycloalkylene, wherein the H atom in the cycloalkylene, or heterocycloalkylene can be substituted by hydroxyl, NO.sub.2, halogen, amino, cyano, —R.sub.21, —OR.sub.21, —COOR.sub.20 or —COR.sub.21; the hetero atom in the heterocyclic ring is selected from oxygen, nitrogen, sulfur, phosphorus or silicon; Q.sub.3 is selected from —O—, —O—CO—O—, —CO—)—, —CO—NR.sub.22—, NR.sub.22—CO—NR.sub.23≤ or —(CH.sub.2).sub.b—, and b is 0, 1 or 2; R.sub.4 and R.sub.5 can be the same or different, and are independently selected from hydrogen, C.sub.1-C.sub.50 alkyl, C.sub.3-C.sub.12 cycloalkyl, and C.sub.2-C.sub.12 heterocycloalkyl, wherein the H atom in the alkyl, cycloalkyl or heterocycloalkyl can be substituted with hydroxyl, —NO.sub.2, halogen, amino, cyano, —R.sub.21, —OR.sub.21, —COOR.sub.21 or —COR.sub.21, and the hetero atom in the heterocyclic ring is selected from oxygen, nitrogen, sulfur, phosphorus or silicon; R.sub.6 is selected from C.sub.1-C.sub.50 alkylene, C.sub.3-C.sub.12 cycloalkylene, and C.sub.2-C.sub.12 heterocycloalkylene, wherein the H atom in the alkylene, cycloalkylene, or heterocycloalkylene can be substituted with hydroxyl, NO.sub.2, halogen, amino, cyano, —R.sub.21, —OR.sub.21, —COOR.sub.21 or —COR.sub.21, and the hetero atom in the heterocyclic ring is selected from oxygen, nitrogen, sulfur, phosphorus or silicon; and, the total number of carbon atoms in R.sub.4, R.sub.5 and R.sub.6 is 50 or less; S.sub.1 is selected from —CH.sub.2—, —CO— or —NR.sub.24—; S.sub.2 is selected from N or C; S3 is selected from —O—, —CH.sub.2—, —CO— or —NR.sub.24—; R.sub.24 is selected from hydrogen, C.sub.1-C.sub.50 alkyl, C.sub.3-C.sub.12 cycloalkyl, and C.sub.2-C.sub.12 heterocycloalkyl, wherein the H atom in the alkyl, cycloalkyl or heterocycloalkyl can be substituted with hydroxyl, —NO.sub.2, halogen, amino, cyano, —R.sub.21, —OR.sub.21, —COOR.sub.21 or —COR.sub.21; the hetero atom in the heterocyclic ring is selected from oxygen, nitrogen, sulfur, phosphorus, silicon or halogen; w is selected from an integer between 1-20, and z is selected from an integer between 2-20; U is selected from R.sub.24 or ##STR00025## g is selected from an integer between 0-20, and h is selected from an integer between 1-20, V is selected from ##STR00026## and R.sub.12 and R.sub.13 are end-capping groups of the polymer, the R.sub.12 and R.sub.13 can be the same or different, and are independently selected from hydrogen, unsubstituted C.sub.4-C.sub.3o alkyl or C.sub.4-C.sub.30 alkyl with any H atom substituted with hydroxyl, —NO.sub.2, halogen, amino, cyano, —R.sub.21, —OR.sub.21, —COOR.sub.21, —COR.sub.21 or C.sub.1-C.sub.10 alkyl, unsubstituted phenyl or phenyl with any H atom substituted with hydroxyl, —NO.sub.2, halogen, amino, cyano, —R.sub.21, —OR.sub.21, —COOR.sub.21, —COR.sub.21 or C.sub.1-30 alkyl, unsubstituted C.sub.7-9 phenylalkyl or C.sub.7-9 phenylalkyl with any H atom of phenyl substituted with hydroxyl, —NO.sub.2, halogen, amino, cyano, —R.sub.21, —OR.sub.21, —COOR.sub.21, —COR.sub.21 or C.sub.1-30 alkyl, ##STR00027##

2. The polymerized high-molecular-weight sterically hindered amine according to claim 1, characterized in that G.sub.1 and G.sub.2 are independently selected from C.sub.1-C.sub.4 alkyl; the R.sub.21 is selected from C.sub.1-C.sub.20 alkyl; E is selected from —CO— or —CH.sub.2—; the Q.sub.1 and Q.sub.2 are independently selected from —O—, —CO—O—, —CO—NR.sub.22— or —NR.sub.22—; the R.sub.22 and R.sub.23 are independently selected from hydrogen and C.sub.1-C.sub.20 alkyl.

3. The polymerized high-molecular-weight sterically hindered amine according to claim 2, characterized in that G.sub.1 and G.sub.2 are independently selected from methyl, and the A.sub.1, A.sub.2, A.sub.3, A.sub.4, A.sub.5, A.sub.6 . . . A.sub.n is selected from the following structural formulas: ##STR00028## ##STR00029## wherein when the monomer has 2 polymerization sites, a linear polymer is formed, and when the monomer has 3 polymerization sites, a hyperbranched polymer is formed.

4. The polymerized high-molecular-weight sterically hindered amine according to claim 3, characterized in that the R.sub.1 and R.sub.2 are independently selected from hydrogen, and C.sub.1-C.sub.40 alkyl, wherein the H atom in the alkyl can be substituted with —R.sub.21, —OR.sub.21, —COOR.sub.21 or —COR.sub.21; the R.sub.3 is selected from C.sub.1-C.sub.40 alkylene, wherein the H atom in the alkylene can be substituted with —R.sub.21, —OR.sub.21, —COOR.sub.21 or —COR.sub.21; the total number of carbon atoms in the R.sub.1, R.sub.2 and R.sub.3 is 40 or less; the R.sub.7 and R.sub.8 are independently selected from hydrogen, unsubstituted C.sub.1-C.sub.20 alkyl or C.sub.1-C.sub.20 alkyl substituted with —R.sub.21; or, R.sub.7, R.sub.8 and the N atom between R.sub.7 and R.sub.8 form unsubstituted C.sub.3-C.sub.12 cycloalkylene or C.sub.2-C.sub.12 heterocycloalkylene; the Q.sub.3 is selected from —O—, —CO—O—, —CO—NR.sub.22— or —NR.sub.22—; and the R.sub.4 and R.sub.5 are independently selected from hydrogen, and C.sub.1-C.sub.40 alkyl, wherein the H atom in the alkyl can be substituted with —R.sub.21, —OR.sub.21, —COOR.sub.21 or —COR.sub.21; the R.sub.6 is selected from C.sub.1-C.sub.40 alkylene, wherein the H atom in the alkylene can be substituted with —R.sub.21, —OR.sub.21, —COOR.sub.21 or —COR.sub.21; and the total number of carbon atoms in the R.sub.4,R.sub.5 and R.sub.6 is 40 or less.

5. The polymerized high-molecular-weight sterically hindered amine according to claim 4, characterized in that the R.sub.21 is selected from hydrogen or C.sub.1-C.sub.12 alkyl; Q.sub.1 and Q.sub.2 are independently selected from —CO—O—, —CO—NR.sub.22— or —NR.sub.22—; the R.sub.22 and R.sub.23 are independently selected from hydrogen, and C.sub.1-C.sub.12 alkyl; the R.sub.7 and R.sub.8 are independently selected from unsubstituted C.sub.1-C.sub.20 alkyl; or, R.sub.7, R.sub.8 and the N atom between R.sub.7 and R.sub.8 form unsubstituted C.sub.3-C.sub.10 cycloalkylene or C.sub.2-C.sub.8 oxo-cycloalkylene; and Q.sub.3 is selected from —NR.sub.22—.

6. The polymerized high-molecular-weight sterically hindered amine according to claim 1, characterized in that the polymerized high-molecular-weight sterically hindered amine of the general formula I can be selected from the following polymerized forms: ##STR00030## ##STR00031## wherein {circle around (A)} and {circle around (B)} represent polymerizable sites, and the {circle around (A)} site can polymerize with the {circle around (B)} site, and when AB is polymerized in the polymer, a linear polymer is formed; when AB.sub.2 is polymerized in the polymer, a hyperbranched polymer is formed; m.sub.n is an integer between 1-20; R.sub.1 and R.sub.2 are independently selected from hydrogen or C.sub.1-C.sub.40 alkyl; R.sub.3 is selected from C.sub.1-C.sub.40 alkylene; the total number of carbon atoms in R.sub.1, R.sub.2 and R.sub.3 is 40 or less; R.sub.22 is selected from C.sub.1-C.sub.5 alkyl; R.sub.7 and R.sub.8 are independently selected from C.sub.1-C.sub.10 alkylene or R.sub.7, R.sub.8 and the N atom between R.sub.7 and R.sub.8 form C.sub.3-C.sub.10 cycloalkylene and C.sub.2-C.sub.8 oxo-cycloalkylene; R.sub.4 and R.sub.5 are independently selected from hydrogen or C.sub.1-C.sub.40 alkyl; R.sub.6 is selected from C.sub.1-C.sub.40 alkylene; the total number of carbon atoms in R.sub.4, R.sub.5 and R.sub.6 is 40 or less; and Q, Q.sub.2 and Q.sub.3 are independently selected from —CO—O—, —CO—NR.sub.22— or —NR.sub.22—, and R.sub.22 is selected from C.sub.1-C.sub.5 alkyl.

7. A method for preparing the polymerized high-molecular-weight sterically hindered amine having the general formula I of claim 1, including the steps of dissolving a polymerizable monomer in a solvent or heating a polymerizable monomer to a molten state, adding a catalyst and hydroperoxide in sequence, and carrying out a reaction to generate the polymerized high-molecular-weight sterically hindered amine having the general formula I, wherein the polymerizable monomer has a general formula as follows: ##STR00032## ##STR00033## wherein R and R′ can be the same or different, and are selected from C.sub.1-C.sub.50 alkyl, C.sub.3-3 C.sub.12 cycloalkyl, and C.sub.2-C.sub.12 heterocycloalkyl, wherein the H atom in the alkyl, cycloalkyl, or heterocycloalkyl can be substituted with hydroxyl, NO.sub.2, halogen, amino, cyano, —R.sub.21, —OR.sub.21, —COOR.sub.21 or —COR.sub.21, and the hetero atom in the heterocyclic ring is selected from oxygen, nitrogen, sulfur, phosphorus or silicon; and the total number of carbon atoms in R and R′ is 50 or less; the solvent is dichlorobenzene, chlorobenzene, toluene, halogenated hydrocarbons, methanol, ethanol, ethylene glycol, methyl ether or water; the catalyst is a metal compound, wherein the metal in the metal compound is selected from IVb, Vb, VIb, VIIb and VIII metal elements in the periodic table; and the hydroperoxide is an inorganic hydroperoxide or an organic hydroperoxide, the inorganic hydroperoxide is H.sub.2O.sub.2; the organic hydroperoxide is an alkyl hydroperoxide and an aryl hydroperoxide.

8. (canceled)

9. A composition, comprising one or two or more organic substances sensitive to light, heat or oxidation and at least one polymerized high-molecular-weight sterically hindered amine having the general formula I, wherein the organic substances and polymerized high-molecular-weight sterically hindered amine having the general formula I can be used in various ratios.

10. (canceled)

Description

DETAILED DESCRIPTION OF THE EMBODIMENTS

[0121] The technical solutions in the examples of the present invention will be clearly and completely described below, Obviously, the described examples are only some of the examples of the present invention, but not all of examples. Based on the examples of the present invention, all other examples obtained by a person of ordinary skill in the art without creative efforts shall fall within the protection scope of the present invention.

EXAMPLE 1

[0122] 81 g of 2,2,6,6-tetramethyl-4-piperidinedodecylamine and 2 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 120° C., then 60 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 12 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 60 g of the target product.

[0123] Molecular weight: 1650 (Mn)

[0124] Dynamic viscosity (140° C.): 152 mPas

EXAMPLE 2

[0125] 81 g of 2,2,6,6-tetramethyl-4-piperidinedodecylamine and 1 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 35 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 48 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 70 g of the target product.

[0126] Molecular weight: 1850 (Mn) Dynamic viscosity (140° C.): 178 mPas cl EXAMPLE 3

[0127] 81 g of 2,2,6,6-tetramethyl-4-piperidinedodecylamine and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 50 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 75 g of the target product.

[0128] Molecular weight: 2028 (Mn)

[0129] Dynamic viscosity (140° C.): 232 mPas

EXAMPLE 4

[0130] 85 g of N-dodecyl-2,2,6,6-tetramethylpiperazinone and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 50 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 77 g of the target product.

[0131] Molecular weight: 1950 (Mn)

[0132] Dynamic viscosity (140° C.): 241 mPas

EXAMPLE 5

[0133] 106 g of 2,2,6,6-tetramethyl-4-piperidinyl stearate and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 50 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 90 g of the target product.

[0134] Molecular weight: 2080 (Mn)

[0135] Dynamic viscosity (140° C.): 267 mPas

EXAMPLE 6

[0136] (1) 36.9 g of cyanuric chloride was dissolved in 300 mL xylene, and cooled to 10° C., 42.4 g of N-(2,2,6,6-tetramethyl-4-piperidinyl)-n-butylamine (the molar ratio of cyanuric chloride to N-(2,2,6,6-tetramethyl-4-piperidinyl)-n-butylamine was 1:1) is added and the mixture was stirred for 1 h, followed by adding 37 g of dodecylamine (the molar ratio of cyanuric chloride to dodecylamine was 1:1), the mixture was stirred at 60° C. for 3 h, then 50 g of a sodium hydroxide aqueous solution (30%) was added, the mixture was stirred for 3 h, the phases were separated, and finally 17.5 g of morpholine (the molar ratio of cyanuric chloride to morpholine was 1:1) was added, and the mixture was heated up to 110° C., and continuously stirred for 6 h. After the reaction was completed, the phases were separated and the organic phase was washed several times with water, and then the organic phase was separated and concentrated under reduced pressure to obtain 116.1 g of an intermediate 1.

##STR00019##

[0137] (2) 86 g of the intermediate 1 and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 50 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 72 g of the target product.

[0138] Molecular weight: 1800 (Mn)

[0139] Dynamic viscosity (140° C.): 532 mPas

EXAMPLE 7

[0140] (1) 36.9 g of cyanuric chloride was dissolved in 300 mL xylene, and cooled to 10° C., 42.4 g of N-(2,2,6,6-tetramethyl-4-piperidinyl)-n-butylamine (the molar ratio of cyanuric chloride to N-(2,2,6,6-tetramethyl-4-piperidinyl)-n-butylamine was 1:1) was added and the mixture was stirred for 1 h, then 50 g of a sodium hydroxide aqueous solution (30%) was added, the mixture was stirred for 3 h, the phases were separated, then 74 g of dodecylamine (the molar ratio of cyanuric chloride to dodecylamine was 1:2) was added, and the mixture was heated up to 100° C., and continuously stirred for 6 h. After the reaction was completed, the phases were separated and the organic phase was washed several times with water, and then the organic phase was separated and concentrated under reduced pressure to obtain 134 g of an intermediate 2.

##STR00020##

[0141] (2) 98 g of the intermediate 2 and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 50 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 85 g of the target product.

[0142] Molecular weight: 1863 (Mn)

[0143] Dynamic viscosity (140° C.): 650 mPas

EXAMPLE 8

[0144] (1) 36.9 g of cyanuric chloride was dissolved in 300 mL xylene, and cooled to 20° C., 84.8 g of N-(2,2,6,6-tetramethyl-4-piperidinyl)-n-butylamine (the molar ratio of cyanuric chloride to N-(2,2,6,6-tetramethyl-4-piperidinyl)-n-butylamine was 1:2) was added and the mixture was stirred for 1 h, then 50 g of a sodium hydroxide aqueous solution (30%) was added, the mixture was stirred for 3 h, the phases were separated, then 37 g of dodecylamine (the molar ratio of cyanuric chloride to dodecylamine is 1:1) was added, and the mixture was heated up to 100° C., and continuously stirred for 6 h. After the reaction was completed, the phases were separated and the organic phase was washed several times with water, and then the organic phase was separated and concentrated under reduced pressure to obtain 140.2 g of an intermediate 3.

##STR00021##

[0145] (2) 102.6 g of the intermediate 3 and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 120° C., then 60 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 95 g of the target product.

[0146] Molecular weight: 1950 (Mn)

[0147] Dynamic viscosity (140° C.): 693 mPas

EXAMPLE 9

[0148] 88 g of 2,2,4,4-tetramethyl-4-piperidinyldodecylamide and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 50 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 75 g of the target product.

[0149] Molecular weight: 1873 (Mn)

[0150] Dynamic viscosity (140° C.): 337 mPas

EXAMPLE 10

[0151] 150.5 g of 2,2,4,4-tetramethyl-20-lauryloxy carbonylethyl-7-oxa-3,20-triazabisspiro [5.1.11. 2]heneicosane-21-one and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 50 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 135.7 g of the target product.

[0152] Molecular weight: 1815 (Mn)

[0153] Dynamic viscosity (140° C.): 527 mPas

EXAMPLE 11

[0154] 90 g of 2,2,4,4-tetramethyl-7-oxa-3,20-triazabisspiro [5.1.11.2]heneicosane-21-one and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 50 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 78 g of the target product.

[0155] Molecular weight: 1835 (Mn)

[0156] Dynamic viscosity (140° C.): 417 mPas

EXAMPLE 12

[0157] 101.5 g of 3-dodecyl-1-(2,2,6,6-tetramethyl-4-piperidyl)pyrrolidine-2,5-dione and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 50 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 90 g of the target product.

[0158] Molecular weight: 1932 (Mn)

[0159] Dynamic viscosity (140° C.): 384 mPas

EXAMPLE 13

[0160] 32.4 g of 2,2,6,6-tetramethyl-4-piperidinedodecylamine, 42.3 g of 2,2,6,6-tetramethyl-4-piperidinyl stearate and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 50 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 67 g of the target product.

[0161] Molecular weight: 2054 (Mn)

[0162] Dynamic viscosity (140° C.): 243 mPas

EXAMPLE 14

[0163] 57.5 g of the intermediate 1, 68.4 g of the intermediate 3 and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 50 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 108 g of the target product.

[0164] Molecular weight: 2628 (Mn)

[0165] Dynamic viscosity (140° C.): 983 mPas

EXAMPLE 15

[0166] 32.4 g of 2,2,6,6-tetramethyl-4-piperidinedodecylamine, 42.3 g of 2,2,6,6-tetramethyl-4-piperidinyl stearate, 57.5 g of the intermediate 1 and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 50 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 110 g of the target product.

[0167] Molecular weight: 2207 (Mn)

[0168] Dynamic viscosity (140° C.): 413 mPas

EXAMPLE 16

[0169] 81 g of 2,2,6,6-tetramethyl-4-piperidinedodecylamine and 3 g of molybdenum trioxide were dissolved in 400 mL chlorobenzene, and heated to 140° C., then 50 g of tert-butyl hydroperoxide (a 70% aqueous solution) was slowly added dropwise, and the mixture was stirred continuously for 60 h. After the reaction was completed, excess saturated sodium sulfite solution was added, and the mixture was stirred, subjected to phase separation, and filtered, and the organic phase was concentrated to obtain 75 g of an intermediate 4.

[0170] 60 g of the intermediate 4 and 32.3 g of di-n-butylamine were dissolved in 400 mL chlorobenzene, and heated to 140° C., and stirred continuously for 60 h. After the reaction was completed, the organic phase was concentrated to obtain 85 g of the target product.

[0171] Molecular weight: 2286 (Mn)

[0172] Dynamic viscosity (140° C.): 271 mPas

EXAMPLE 17

Experiment of Stabilizing Polypropylene Materials

[0173] Basic formulation:

[0174] Standard polymer: 79.8 wt % of thermoplastic polypropylene; 20 wt % of hydrotalcite; and 0.20 wt % of an antioxidant (AO-1010);

[0175] 1# was 100 wt % of the standard polymer;

[0176] 2# was 99.7 wt % of the standard polymer, and 0.3 wt % of sterically hindered amine (Example 3);

[0177] 3# was 99.7 wt % of the standard polymer, and 0.3 wt % of sterically hindered amine (Example 5);

[0178] 4# was 99.7 wt % of the standard polymer, and 0.3 wt % of sterically hindered amine (Example 6);

[0179] 5# was 99.7 wt % of the standard polymer, and 0.3 wt % of sterically hindered amine (Example 8);

[0180] 6# was 99.7 wt % of the standard polymer, 0.3 wt % of the sterically hindered amine (Example 13);

[0181] 7# was 99.7 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 14);

[0182] 8# was 99.7 wt % of the standard polymer, and 0.3 wt % of sterically hindered amine (Example 15);

[0183] Preparation of test samples:

[0184] The components were mixed in advance in a mixer, and then extruded and pelletized on a twin-screw extruder at 220° C. The pelletized materials were dried at 80° C. for 8 h, and then injection-molded at 240° C. by using an injection molding machine. Finally, the samples were subjected to the xenon lamp aging test according to the SAE J 2527 standard. The test results were shown in Table 1:

TABLE-US-00001 TABLE 1 ΔE* of samples after xenon lamp aging (low value required) ΔE* at different aging times Sample 0 500 h 1000 h 1500 h 2000 h 1# 0 10.5 14.3 — — 2# 0 0.31 0.95 1.41 1.84 3# 0 0.37 0.98 1.37 1.83 4# 0 0.42 1.03 1.32 1.76 5# 0 0.29 0.81 1.12 1.69 6# 0 0.32 0.96 1.40 1.84 7# 0 0.30 0.93 1.21 1.72 8# 0 0.31 0.94 1.35 1.80

EXAMPLE 18

Test of Stabilizing Thermoplastic Polyethylene

[0185] Basic formulation:

[0186] Standard polymer: 79.8 wt % of thermoplastic polyethylene; 20 wt % of calcium carbonate;

[0187] and 0.20 wt % of an antioxidant (AO-1010);

[0188] 1# was 100 wt % of the standard polymer;

[0189] 2# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 3);

[0190] 3# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine

[0191] (Example 5);

[0192] 4# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 6);

[0193] 5# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 8);

[0194] 6# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 13);

[0195] 7# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 14);

[0196] 8# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 15);

[0197] Preparation of test samples:

[0198] The components were mixed in advance in a mixer, and then extruded and pelletized on a twin-screw extruder at 190° C. The pelletized materials were dried at 80° C. for 8 h, and then blow-molded at 200° C. by using a blown film machine. Finally, the samples were subjected to an artificial accelerated aging test of xenon lamps in accordance with GB/T 16422.2-2014. The test results were shown in Table 2:

TABLE-US-00002 TABLE 2 % Retention rate of tensile strength Retention rate of tensile strength Sample 0 300 h 600 h 1200 h 1800 h 1# 100% 90% 75% 45% — 2# 100% 93% 89% 74% 53% 3# 100% 92% 89% 75% 52% 4# 100% 93% 88% 80% 65% 5# 100% 95% 90% 83% 75% 6# 100% 92% 88% 75% 52% 7# 100% 94% 90% 81% 72% 8# 100% 93% 89% 81% 70%

EXAMPLE 19

Test of Stabilizing Thermoplastic Polyvinylchloride

[0199] Basic formulation:

[0200] Standard polymer: 65.5 wt % of thermoplastic polyvinyl chloride; 31.5 wt % of a plasticizer; 1.6 wt % of epoxy soybean oil; and 1.4 wt % of a calcium-zinc stabilizer;

[0201] 1# was 100 wt % of the standard polymer;

[0202] 2# was 99.5 wt % of the standard polymer, 0.25 wt % of UV-531, and 0.25 wt % of sterically hindered amine (Example 3);

[0203] 3# was 99.5 wt % of the standard polymer, 0.25 wt % of UV-531, and 0.25 wt % of sterically hindered amine (Example 5);

[0204] 4# was 99.5 wt % of the standard polymer, 0.25 wt % of UV-531, and 0.25 wt % of sterically hindered amine (Example 6);

[0205] 5# was 99.5 wt % of the standard polymer, 0.25 wt % of UV-531, and 0.25 wt % of sterically hindered amine (Example 8);

[0206] Preparation of test samples:

[0207] The components were mixed in advance in a mixer, and then mixed on a double-roll mill at 165° C. for 7 minutes to obtain the required samples. Finally, the samples were subjected to an xenon lamp aging test according to GB/T 16422.2-2014. The test results were shown in Table 3:

TABLE-US-00003 TABLE 3 % Retention rate of elongation at break % Retention rate of elongation at break Sample 0 200 h 800 h 1200 h 1# 100% 82% 60% 45% 2# 100% 90% 74% 65% 3# 100% 91% 72% 64% 4# 100% 90% 78% 70% 5# 100% 95% 88% 81%

EXAMPLE 20

Test of Stabilizing Thermoplastic Polyamide 6

[0208] Basic formulation:

[0209] Standard polymer: 79.8 wt % of thermoplastic polyamide 6; 20 wt % of calcium carbonate;

[0210] and 0.20 wt % of an antioxidant (AO-1098);

[0211] 1# was 100 wt % of the standard polymer;

[0212] 2# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 3);

[0213] 3# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 9);

[0214] 4# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 10);

[0215] 5# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 11);

[0216] 6# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 12);

[0217] Preparation of test samples:

[0218] The components were mixed in advance in a mixer, and then extruded and pelletized on a twin-screw extruder at 260° C., dried at 80° C. for 12 h, and then injection molded at 265° C. by using an injection molding machine. Finally, the samples were subjected to the xenon lamp aging test according to the standard GB/T 16422.2-2014. The test results were shown in Table 4:

TABLE-US-00004 TABLE 4 ΔE* of samples after xenon lamp aging (low value required) ΔE* at different aging times Sample 0 300 h 600 h 1200 h 1800 h 1# 0 3.12 8.54 16.32 26.73 2# 0 2.85 7.32 14.11 23.58 3# 0 1.13 3.05 7.67 11.64 4# 0 1.05 2.95 7.53 11.48 5# 0 1.25 3.37 8.01 12.32 6# 0 1.32 3.43 8.02 12.35

EXAMPLE 21

Performance Test of Using as Flame Retardant in PP Film

[0219] Basic formulation:

[0220] Standard polymer: 99.65 wt % of thermoplastic polypropylene; 0.05 wt % of calcium stearate; and 0.30 wt % of an antioxidant (AO-1010:AO-168=1:1);

[0221] 1# was 100 wt % of the standard polymer; 2# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 3);

[0222] 3# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 5);

[0223] 4# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 6);

[0224] 5# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 8);

[0225] Preparation of test samples:

[0226] The components were mixed in advance in a mixer, and then extruded and pelletized on a twin-screw extruder at 220° C. The pelletized materials were dried at 80° C. for 8 h, and then subjected to compression molding in a hot press for preparation. Finally, the samples were tested for flame retardancy according to DIN 4102-B2. The test results were shown in Table 5:

TABLE-US-00005 TABLE 5 Sample flame retardant performance Weight Flame Flame Pass/ Sample loss/% length/mm drops fail 1# 100 190 Yes Fail 2# 8.5 104 Yes Pass 3# 8.4 102 Yes Pass 4# 8.7 105 Yes Pass 5# 6.5 87 Yes Pass

Example 22

Performance Test of Using as Flame Retardant in Polyamide 6

[0227] Basic formulation: Standard polymer: 79.8 wt % of thermoplastic polyamide 6; 20 wt % of calcium carbonate; and 0.20 wt % of an antioxidant (AO-1098); 1# was 100 wt % of the standard polymer;

[0228] 2# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 3);

[0229] 3# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 9);

[0230] 4# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 10); 5# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 11);

[0231] 6# was 99.6 wt % of the standard polymer, and 0.4 wt % of sterically hindered amine (Example 12);

[0232] Preparation of test samples:

[0233] The components were mixed in advance in a mixer, and then extruded and pelletized on a twin-screw extruder at 260° C. The pelletized materials were dried at 80° C. for 12 h, and then injection molded at 265° C. by using an injection molding machine. Finally, the samples were tested for flame retardancy according to UL94. The test results were shown in Table 6:

TABLE-US-00006 TABLE 6 Sample flame retardant performance Sample V level Flame drops 1# 2 Yes 2# 2 Yes 3# 1 No 4# 1 No 5# 1 No 6# 1 No

[0234] In the end, it should be noted that the above examples are only used to illustrate the technical solution of the present invention, rather than limiting the present invention; although the present invention has been described in detail with reference to the foregoing examples, those of common skillers in the art will understand: they can still modify the technical solutions described in the foregoing examples or replace some or all of the technical features equivalently;

[0235] and these modifications or replacements do not deviate the essence of the corresponding technical solutions from the scope of the technical solutions of examples in the present invention.