Polymerization method for sulfate ester (amine) type linker polymer

Abstract

The present invention relates to a synthesis method for sulfate ester (amine) type linker polymer, which comprises a monomer containing hydroxyl or amino group and sulfuryl fluoride monomer proceeding a polycondensation reaction under a basic condition by one-pot process. As compared to the traditional polyester synthesis method, the present invention is economical; the reaction conditions are mild and easy to control, the reaction process is simple and easy to operate; the post-treatment process is simple with little environmental pollution, which is beneficial to industrial production. In addition, the bisphenol type polysulfate ester compounds synthesized by the present invention have excellent mechanical performances, dielectric performances, tolerance performances, and abrasion resistance performances.

Claims

1. A synthesis method for sulfate ester (amine) type linker polymer, consisting of: a monomer containing free hydroxyl group or free amino group and a monomer containing sulfuryl fluoride group proceeding a polycondensation reaction under a basic condition by one-pot process, wherein, the monomer containing free hydroxyl group has a structural formula of HOX(OH).sub.n, wherein X is an aromatic group containing a heterocycle, an aromatic group containing no heterocycle, aliphatic hydrocarbon, amino acid, or amino acid derivative, and a is an integer of 1 to 3, the monomer containing free amino group has a structural formula of H.sub.2NZ(NH.sub.2).sub.b, wherein Z is an aromatic group containing a heterocycle, an aromatic group containing no heterocycle, aliphatic hydrocarbon, amino acid, or amino acid derivative, and b is an integer of 1 to 3, the monomer containing sulfuryl fluoride group has a structural formula of ##STR00027## wherein R is S, C(CF.sub.3).sub.2, C(O), C(O)NH, or C(O)O), wherein the basic condition is achieved by adding a base, and the base is an inorganic base, wherein the inorganic base and the monomer containing sulfuryl fluoride group have a molar ratio of 0.5:1-4:1, wherein the polycondensation reaction occurs in a presence or absence of solvent.

2. The synthesis method according to claim 1, wherein the monomer containing free hydroxyl group is a bisphenol monomer having a structural formula of ##STR00028## wherein R is S, O, CH.sub.2, C(CH.sub.3).sub.2, C(CF.sub.3).sub.2, C(O), S(O).sub.2, C(O)NH, or C(O)O.

3. The synthesis method according to claim 1, wherein the inorganic base is at least one selected from the group consisting of potassium phosphate, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium phosphate, and cesium carbonate.

4. The synthesis method according to claim 1, wherein the solvent is at least one selected from the group consisting of sulfolane, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DEF), dimethyl sulfoxide (DMSO), N-methylpyrrolidone (NMP), chlorobenzene, xylene, trimethylbenzene, tetrahydrofuran, n-hexane, and cyclopentane, the solvent comprises at least one water-carrying agent, and the water-carrying agent is chlorobenzene, xylene, trimethylbenzene, or n-hexane.

5. The synthesis method according to claim 1, wherein when the polycondensation reaction occurs in the absence of the solvent, and the polycondensation reaction proceeds in a state that the monomer containing free hydroxyl group or free amino group and the monomer containing sulfuryl fluoride group are molten.

6. The synthesis method according to claim 1, wherein the synthesis method proceeds end-capping reaction or end modification reaction after the polycondensation reaction is complete.

7. The synthesis method according to claim 6, wherein an end-capping reagent in the end-capping reaction is at least one selected from the group consisting of chloromethane, phenol, phenol-based derivatives, and chlorobenzophenone monofunctional compound.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) FIG. 1 is the .sup.1H-NMR spectra of bisphenol A type sulfuryl fluoride monomer.

(2) FIG. 2 is the .sup.13C-NMR spectra of bisphenol A type sulfuryl fluoride monomer.

(3) FIG. 3 is the schematic diagram of the purity analysis result of bisphenol A by HPLC.

(4) FIG. 4 is the schematic diagram of the HPLC analysis result of bisphenol A type sulfuryl fluoride monomer.

(5) FIG. 5 is the schematic diagram of the HPLC analysis result of diphenyl ether type sulfuryl fluoride monomer.

(6) FIG. 6 is the .sup.1H-NMR spectra of PSE-1.

(7) FIG. 7 is the .sup.13C-NMR spectra of PSE-1.

(8) FIG. 8 is the schematic diagram of the TGA analysis result of PSE.

(9) FIG. 9 is the schematic diagram of the TGA and DSC analysis results of PSE.

(10) FIG. 10 is the spectra of the FTIR analysis of PSE-1.

(11) FIG. 11 is the spectra of the FTIR analysis of BPA-B.

(12) FIG. 12 is the schematic diagram of the Gel chromatography analysis

MODE FOR CARRYING OUT THE INVENTION

(13) Syntheses and performances of the polysulfate ester (amine) compounds containing 4,4-dihydroxy-diphenyl involved in the present invention are further described by specific examples as follows.

(14) Example 1. Synthesis of polysulfate ester-1 containing 4,4-dihydroxy-diphenyl with polymerization degree of 5-1000

(15) (1) Synthesis of bisphenol protected by sulfonyl fluoride: 228 g (1 mol) of bisphenol A was dissolved in 100 mL of dichloromethane or chloroform, 24.2 g (2.40 mol) of triethylamine was added, and sulfonyl fluoride gas was carefully and continuously introduced. The reaction was carried out at room temperature for 12 hours, and after the reaction was complete, 388 g of bisphenol A protected by sulfonyl fluoride (1,4-phenylene bis(sulfuroidate)), a dark brown solid, could be obtained through being simply concentrated, filtered, and washed, yield: 99%.

(16) NMR analysis data of the synthesized product: .sup.1H NMR (400 MHz, CDCl.sub.3) 7.36-7.15 (m, 8H), 1.69 (s, 6H). 13C NMR (400 MHz, CDCl.sub.3) 150.44, 148.20, 128.74, 120.61, 42.95, 30.75

(17) The synthesized product has a structural formula as follows:

(18) ##STR00013##

(19) Experiments have shown that, in the above reaction process, when dichloroethane, ethyl acetate, acetonitrile, toluene, or dioxane are used as solvents; the organic amine uses trimethylamine (TMA), tripropylamine, tributylamine (TBA), diethylamine (DEA), diisopropylethylamine, diisopropylamine (DIPA); ammonia, ammonia gas can also be used; pyridine, piperidine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,4-diazabicyclo[2.2.2]octane (DABCO), 4-dimethylaminopyridine (DMAP), dimethylcyclohexylamine (DMCHA), all can deliver bisphenol A protected by sulfonyl fluoride in different yields (58% to 99%).

(20) (1) Synthesis of Bisphenol Type Polysulfate Ester-1 (PSE-1) with Polymerization Degree of 5500

(21) ##STR00014##

(22) 392 g (1 mol) of the above prepared bisphenol A protected by sulfonyl fluoride and 228 g (1 mol) of bisphenol A with an equal molar amount, 760 g of NMP solvent, and 100 g of toluene were completely dissolved by heating, then 1.2 molar amount (1.2 mol) of inorganic base sodium carbonate was added, and the mixture was reacted at 150 C. with mechanical stirring for 1 hour, and poured into water to terminate the reaction. The precipitated polymerization product is separated, extracted by ethanol, and dried to obtain a white solid PSE-1 containing 4,4-dihydroxy-diphenyl: 556 g, yield: 99%. If ends need to be capped, after the molecular weight of polycondensation reaches a certain value, the end-capping reagent chloromethane solution (0.05 mol) is added, and reacted for 15 min, then poured into water to terminate and precipitate the product. After the product is separated, the end-capped PSE-1 product is obtained through being washed and dried. PSE-1 has a number-average molecular weight of 42880, and good resistance to acid and base, which does not decompose after being left in concentrated sulphuric acid and concentrated nitric acid for months.

(23) The performance indicators of the polymerization products are as follows (referring to FIG. 12): Weight-average molecular weight (Mw)=8.625e+4 Number-average molecular weight (Mn)=4.288e+4 Polydispersity index (PDI [Mw/Mn])=3.01 Polymerization degree: 1050 Base resistance (10% aqueous NaOH at room temperature): good

(24) Experiments have shown that, in the above polymerization reaction processes, when potassium phosphate, sodium carbonate, sodium carbonate, cesium carbonate, etc. are used, polysulfate ester-1 (PSE-1) containing bisphenol A with similar polymerization degrees and performances can also be obtained.

(25) TABLE-US-00001 reagent R base Mn 10*.sup.4 Dpi yield % R = OH R = OSO.sub.2F a b a + b Na.sub.2CO.sub.3 K.sub.2CO.sub.3 K.sub.3PO.sub.4 11.4 5.3 4.8 1.50 1.44 1.50 94.5 95.2 92.4 R = OH R = OSO.sub.2F c d a + d K.sub.2CO.sub.3 4.6 2.01 97.2 R = OH R = OSO.sub.2F e f b + f K.sub.2CO.sub.3 6.8 1.98 95.3

(26) Reaction conditions: 1:1 of bisphenol monomer and bisulfuryl fluoride monomer; 1.2 equivalents of base is added; solvent and dehydrating agent are added; the temperature is raised to 90-150 C. to become saline water and continues to be raised between 130-190 C. for polycondensation reaction; if ends need to be capped after the polymerization is complete, then about 1-5% equivalents of end-capping reagent is added, further reacted for 10-20 h, poured into water for precipitation, and the product is obtained by continuing to be washed and dried.

(27) Example 2. Synthesis of polysulfate ester-1 4,4-dihydroxy-diphenyl with polymerization degree of 5500 (PSE-2) containing

(28) (1) Synthesis of Bisphenol A Protected by Sulfonyl Fluoride: The Same as in Example 1.

(29) (2) Synthesis of Bisphenol Type Polysulfate Ester-2 (PSE-2) with Polymerization Degree of 10500

(30) ##STR00018##

(31) Under the atmosphere of nitrogen, 392 g (10 mol) of the above prepared bisphenol A protected by sulfonyl fluoride and 202 g (10 mol) of 4,4-dihydroxy-diphenyl ether with an equal molar amount, 300 g of NMP solvent, and 50 g of xylene were completely dissolved by heating, then 120% molar amount (1.2 mol) of the catalyst potassium carbonate was added, and the mixture was reacted at 130 C. with mechanical stirring for 2 hour, raised to 170 C. and reacted for 12 h, and poured into water to terminate the reaction. The precipitated polymerization product is separated, extracted by ethanol, and dried to obtain a white solid polysulfate ester PSE-2 containing 4,4-dihydroxy-diphenyl: yield: 97%. PSE-2 has a number-average molecular weight Mn of 40.1 kDa, and PDI=1.41.

(32) As can be seen, as compared to the traditional polyester synthesis method, the present invention is economical, and the by-products are fluoride inorganic salts, which can be sold as industrial products; the reaction conditions are mild and easy to control, the reaction process is simple and easy to operate; the post-treatment process is simple with little environmental pollution, which is beneficial to industrial production. In addition, the bisphenol type polysulfate ester compounds synthesized by the present invention have excellent mechanical performances, dielectric performances, tolerance performances, and abrasion resistance performances.

(33) Example 3. Synthesis of polysulfate ester-3 containing 4,4-dihydroxy-diphenyl thioether with polymerization degree of 5500 (PSE-3)

(34) (1) Synthesis of Bisphenol A Protected by Sulfonyl Fluoride: The Same as in Example 1.

(35) (2) Synthesis of Bisphenol Type Polysulfate Ester-3 (PSE-3) with Polymerization Degree of 10500

(36) ##STR00019##

(37) Under the atmosphere of nitrogen, 392 g (10 mol) of the above prepared bisphenol A protected by sulfonyl fluoride and 218 g (10 mol) of 4,4-dihydroxy-diphenyl thioether with an equal molar amount, 300 g of NMP solvent, and 50 g of xylene were completely dissolved by heating, then 120% molar amount (1.2 mol) of the catalyst potassium carbonate was added, and the mixture was reacted at 130 C. with mechanical stirring for 2 hour, raised to 170 C. and reacted for 12 h, and poured into water to terminate the reaction. The precipitated polymerization product is separated, extracted by ethanol, and dried to obtain a white solid polysulfate ester PSE-3 containing 4,4-dihydroxy-diphenyl: yield: 98%. PSE-3 has a number-average molecular weight Mn of 90.2 kDa, and PDI=1.65.

(38) As can be seen, as compared to the traditional polyester synthesis method, the present invention is economical, and the by-products are fluoride inorganic salts, which can be sold as industrial products; the reaction conditions are mild and easy to control, the reaction process is simple and easy to operate; the post-treatment process is simple with little environmental pollution, which is beneficial to industrial production. In addition, the bisphenol type polysulfate ester compounds synthesized by the present invention have excellent mechanical performances, dielectric performances, tolerance performances, and abrasion resistance performances.

(39) Example 4. Synthesis of polysulfate ester-4 containing 4,4-dihydroxy-diphenyl sulphone with polymerization degree of 10500 (PSE-4)

(40) (1) Synthesis of Bisphenol A Protected by Sulfonyl Fluoride: The Same as in Example 1.

(41) (2) Synthesis of Bisphenol Type Polysulfate Ester-4 (PSE-4) with Polymerization Degree of 10500

(42) ##STR00020##

(43) Under the atmosphere of nitrogen, 392 g (10 mol) of the above prepared bisphenol A protected by sulfonyl fluoride and 250 g (10 mol) of 4,4-dihydroxy-diphenyl sulphone with an equal molar amount, 300 g of NMP solvent, and 50 g of xylene were completely dissolved by heating, then 120% molar amount (1.2 mol) of the catalyst potassium carbonate was added, and the mixture was reacted at 130 C. with mechanical stirring for 2 hour, raised to 170 C. and reacted for 12 h, and poured into water to terminate the reaction. The precipitated polymerization product is separated, extracted by ethanol, and dried to obtain a white solid polysulfate ester PSE-4 containing 4,4-dihydroxy-diphenyl: yield: 97%. PSE-4 has a number-average molecular weight Mn of 41.2 kDa, and PDI=1.45.

(44) As can be seen, as compared to the traditional polyester synthesis method, the present invention is economical, and the by-products are fluoride inorganic salts, which can be sold as industrial products; the reaction conditions are mild and easy to control, the reaction process is simple and easy to operate; the post-treatment process is simple with little environmental pollution, which is beneficial to industrial production. In addition, the bisphenol type polysulfate ester compounds synthesized by the present invention have excellent mechanical performances, dielectric performances, tolerance performances, and abrasion resistance performances.

(45) Example 5. Synthesis of polysulfate ester-5 containing 4,4-dihydroxy-diphenyl ketone with polymerization degree of 5500 (PSE-5)

(46) (1) Synthesis of Bisphenol A Protected by Sulfonyl Fluoride: The Same as in Example 1.

(47) (2) Synthesis of Bisphenol Type Polysulfate Ester-5 (PSE-5) with Polymerization Degree of 10500

(48) ##STR00021##

(49) Under the atmosphere of nitrogen, 392 g (10 mol) of the above prepared bisphenol A protected by sulfonyl fluoride and 202 g (10 mol) of 4,4-dihydroxy-diphenyl ketone with an equal molar amount, 300 g of NMP solvent, and 50 g of xylene were completely dissolved by heating, then 120% molar amount (1.2 mol) of the catalyst potassium carbonate was added, and the mixture was reacted at 130 C. with mechanical stirring for 2 hour, raised to 170 C. and reacted for 12 h, and poured into water to terminate the reaction. The precipitated polymerization product is separated, extracted by ethanol, and dried to obtain a white solid polysulfate ester PSE-5 containing 4,4-dihydroxy-diphenyl: yield: 98%. PSE-5 has a number-average molecular weight Mn of 69.2 kDa, and PDI=1.52.

(50) As can be seen, as compared to the traditional polyester synthesis method, the present invention is economical, and the by-products are fluoride inorganic salts, which can be sold as industrial products; the reaction conditions are mild and easy to control, the reaction process is simple and easy to operate; the post-treatment process is simple with little environmental pollution, which is beneficial to industrial production. In addition, the bisphenol type polysulfate ester compounds synthesized by the present invention have excellent mechanical performances, dielectric performances, tolerance performances, and abrasion resistance performances.

(51) Example 6. Synthesis of polysulfate ester-6 containing 4,4-dihydroxy-diphenyl thioether with polymerization degree of 5500 (PSE-6)

(52) (1) Synthesis of Bisphenol 4,4-Dihydroxy-Diphenyl Thioether Protected by Sulfonyl Fluoride: The Same as in Example 1.

(53) (2) Synthesis of Bisphenol Type Polysulfate Ester-6 (PSE-6) with Polymerization Degree of 10500

(54) ##STR00022##

(55) Under the atmosphere of nitrogen, 382 g (10 mol) of the above prepared bisphenol 4,4-dihydroxy-diphenyl thioether protected by sulfonyl fluoride and 250 g (10 mol) of 4,4-dihydroxy-diphenyl thioether with an equal molar amount, 300 g of NMP solvent, and 50 g of xylene were completely dissolved by heating, then 120% molar amount (1.2 mol) of the catalyst potassium carbonate was added, and the mixture was reacted at 130 C. with mechanical stirring for 2 hour, raised to 170 C. and reacted for 12 h, and poured into water to terminate the reaction. The precipitated polymerization product is separated, extracted by ethanol, and dried to obtain a white solid polysulfate ester PSE-6 containing 4,4-dihydroxy-diphenyl thioether: yield: 95%. PSE-6 has a number-average molecular weight Mn of 77.9 kDa, and PDI=1.57.

(56) As can be seen, as compared to the traditional polyester synthesis method, the present invention is economical, and the by-products are fluoride inorganic salts, which can be sold as industrial products; the reaction conditions are mild and easy to control, the reaction process is simple and easy to operate; the post-treatment process is simple with little environmental pollution, which is beneficial to industrial production. In addition, the bisphenol type polysulfate ester compounds synthesized by the present invention have excellent mechanical performances, dielectric performances, tolerance performances, and abrasion resistance performances.

(57) Example 7. Synthesis of polysulfate ester-7 containing 4,4-dihydroxy-diphenyl sulphone with polymerization degree of 5500 (PSE-7)

(58) (1) Synthesis of 4,4-Dihydroxy-Diphenyl Sulphone Protected by Sulfonyl Fluoride: The Same as in Example 1.

(59) (2) Synthesis of Bisphenol Type Polysulfate Ester-7 (PSE-7) with Polymerization Degree of 10500

(60) ##STR00023##

(61) Under the atmosphere of nitrogen, 414 g (10 mol) of the above prepared 4,4-dihydroxy-diphenyl sulphone protected by sulfonyl fluoride and 250 g (10 mol) of 4,4-dihydroxy-diphenyl ether with an equal molar amount, 300 g of NMP solvent, and 50 g of xylene were completely dissolved by heating, then 120% molar amount (1.2 mol) of the catalyst potassium carbonate was added, and the mixture was reacted at 130 C. with mechanical stirring for 2 hour, raised to 170 C. and reacted for 12 h, and poured into water to terminate the reaction. The precipitated polymerization product is separated, extracted by ethanol, and dried to obtain a white solid polysulfate ester PSE-7 containing 4,4-dihydroxy-diphenyl: yield: 95%. PSE-7 has a number-average molecular weight Mn of 40.6 kDa, and PDI=1.44.

(62) As can be seen, as compared to the traditional polyester synthesis method, the present invention is economical, and the by-products are fluoride inorganic salts, which can be sold as industrial products; the reaction conditions are mild and easy to control, the reaction process is simple and easy to operate; the post-treatment process is simple with little environmental pollution, which is beneficial to industrial production. In addition, the bisphenol type polysulfate ester compounds synthesized by the present invention have excellent mechanical performances, dielectric performances, tolerance performances, and abrasion resistance performances.

(63) Example 8. Synthesis of polysulfate ester-8 containing 4,4-dihydroxy-diphenyl ketone with polymerization degree of 5500 (PSE-8)

(64) (1) Synthesis of 4,4-Dihydroxy-Diphenyl Ketone Protected by Sulfonyl Fluoride: The Same as in Example 1.

(65) (2) Synthesis of Bisphenol Type Polysulfate Ester-8 (PSE-8) with Polymerization Degree of 10500

(66) ##STR00024##

(67) Under the atmosphere of nitrogen, 387 g (10 mol) of the above prepared 4,4-dihydroxy-diphenyl ketone protected by sulfonyl fluoride and 214 g (10 mol) of 4,4-dihydroxy-diphenyl ketone with an equal molar amount, 300 g of NMP solvent, and 50 g of xylene were completely dissolved by heating, then 120% molar amount (1.2 mol) of the catalyst potassium carbonate was added, and the mixture was reacted at 130 C. with mechanical stirring for 2 hour, raised to 170 C. and reacted for 12 h, and poured into water to terminate the reaction. The precipitated polymerization product is separated, extracted by ethanol, and dried to obtain a white solid polysulfate ester PSE-8 containing 4,4-dihydroxy-diphenyl: yield: 97%. PSE-8 has a number-average molecular weight Mn of 132.2 kDa, and PDI=2.62.

(68) As can be seen, as compared to the traditional polyester synthesis method, the present invention is economical, and the by-products are fluoride inorganic salts, which can be sold as industrial products; the reaction conditions are mild and easy to control, the reaction process is simple and easy to operate; the post-treatment process is simple with little environmental pollution, which is beneficial to industrial production. In addition, the bisphenol type polysulfate ester compounds synthesized by the present invention have excellent mechanical performances, dielectric performances, tolerance performances, and abrasion resistance performances.

(69) Example 9. Synthesis of polysulfate ester-9 containing 4,4-dihydroxy-biphenyl with polymerization degree of 5-500 (PSE-9)

(70) (1) Synthesis of Bisphenol A Protected by Sulfonyl Fluoride: The Same as in Example 1.

(71) (2) Synthesis of Bisphenol Type Polysulfate Ester-9 (PSE-9) with Polymerization Degree of 10500

(72) ##STR00025##

(73) Under the atmosphere of nitrogen, 392 g (10 mol) of the above prepared bisphenol A protected by sulfonyl fluoride and 186 g (10 mol) of 4,4-dihydroxy-biphenyl with an equal molar amount, 300 g of NMP solvent, and 50 g of xylene were completely dissolved by heating, then 120% molar amount (1.2 mol) of the catalyst potassium carbonate was added, and the mixture was reacted at 130 C. with mechanical stirring for 2 hour, raised to 170 C. and reacted for 12 h, and poured into water to terminate the reaction. The precipitated polymerization product is separated, extracted by ethanol, and dried to obtain a white solid polysulfate ester PSE-9 containing 4,4-dihydroxy-diphenyl: yield: 95%. PSE-9 has a number-average molecular weight Mn of 79.2 kDa, and PDI=1.60.

(74) As can be seen, as compared to the traditional polyester synthesis method, the present invention is economical, and the by-products are fluoride inorganic salts, which can be sold as industrial products; the reaction conditions are mild and easy to control, the reaction process is simple and easy to operate; the post-treatment process is simple with little environmental pollution, which is beneficial to industrial production. In addition, the bisphenol type polysulfate ester compounds synthesized by the present invention have excellent mechanical performances, dielectric performances, tolerance performances, and abrasion resistance performances.

(75) Example 10. Synthesis of polysulfate ester-10 containing 4,4-dihydroxy-biphenyl with polymerization degree of 10-500 (PSE-10)

(76) (1) Synthesis of 4,4-Dihydroxy-Biphenyl Protected by Sulfonyl Fluoride: The Same as in Example 1.

(77) (2) Synthesis of Bisphenol Type Polysulfate Ester-10 (PSE-10) with Polymerization Degree of 10500

(78) ##STR00026##

(79) Under the atmosphere of nitrogen, 350 g (10 mol) of the above prepared bisphenol A protected by sulfonyl fluoride and 186 g (10 mol) of 4,4-dihydroxy-diphenyl ether with an equal molar amount, 300 g of NMP solvent, and 50 g of xylene were completely dissolved by heating, then 120% molar amount (1.2 mol) of the catalyst potassium carbonate was added, and the mixture was reacted at 130 C. with mechanical stirring for 2 hour, raised to 170 C. and reacted for 12 h, and poured into water to terminate the reaction. The precipitated polymerization product is separated, extracted by ethanol, and dried to obtain a white solid polysulfate ester PSE-10 containing 4,4-dihydroxy-diphenyl: yield: 95%. PSE-10 has a number-average molecular weight Mn of 126.2 kDa, and PDI=1.72.

(80) As can be seen, as compared to the traditional polyester synthesis method, the present invention is economical, and the by-products are fluoride inorganic salts, which can be sold as industrial products; the reaction conditions are mild and easy to control, the reaction process is simple and easy to operate; the post-treatment process is simple with little environmental pollution, which is beneficial to industrial production. In addition, the bisphenol type polysulfate ester compounds synthesized by the present invention have excellent mechanical performances, dielectric performances, tolerance performances, and abrasion resistance performances.