Method for preparing aliphatic polythioether

Abstract

A method for preparing aliphatic polythioether is provided. In the method, aliphatic polythioether is obtained by polymerization reaction using a sulfur-carbon compound and an oxygen-containing monomer as raw materials and using Lewis base as a catalyst, and the polymerization reaction is performed under a self-generated pressure at 80˜180° C. Based on the defects of the traditional preparation process of aliphatic polythioether, a bran-new synthetic routine is provided, in which a new process for preparing polythioether in one-pot reaction is achieved through oxygen-sulfur exchange reaction between the sulfur-carbon compound and the oxygen-containing monomer.

Claims

1. A method for preparing aliphatic polythioether, which is obtained by polymerization reaction using a sulfur-carbon compound and an oxygen-containing monomer as raw materials and using only bis(triphenylphosphoranyl) ammonium chloride as a catalyst; the polymerization reaction is performed under a self-generated pressure at 130˜180° C.; a molar ratio of the sulfur-carbon compound to the oxygen-containing monomer is 1 5:1; a molar ratio of the catalyst to the oxygen-containing monomer is 1:10˜500; the sulfur-carbon compound is selected from at least one of carbon disulfide and carbon oxysulfide; the oxygen-containing monomer is selected from at least one of epoxide, oxetane and 3-substituted oxetane.

2. The method for preparing aliphatic polythioether according to claim 1, wherein the epoxide is ethylene oxide; the 3-substituted oxetane is selected from at least one of 3,3-dimethlyoxetane, 3-methyl-3-benzyloxymethyloxetane,3-chloromethyl-3-methlyxetane,3-methyl-3-oxetane methanol,3-oxetanone, 3-(allyloxy) oxetane and 3-bromooxetane.

3. The method for preparing aliphatic polythioether according to claim 1, wherein the polymerization reaction is bulk polymerization.

4. The method for preparing aliphatic polythioether according to claim 1, wherein the polymerization reaction is solution polymerization, a solvent is dichloromethane.

5. The method for preparing aliphatic polythioether according to claim 1, specifically comprising: polymerizing in a high-pressure reactor under dry and oxygen-free conditions by using the sulfur-carbon compound and the oxygen-containing monomer as polymerization monomers and using the Lewis base as the catalyst, followed by adding alcohol-hydrochloric acid solution and posttreating to obtain the aliphatic polythioether.

Description

DESCRIPTION OF THE DRAWINGS

(1) FIG. 1 is a .sup.1H NMR spectrum of polythioeter prepared in comparative example 1;

(2) FIG. 2 is a .sup.1H NMR spectrum of polythioeter prepared in example 1;

(3) FIG. 3 is a .sup.13C NMR spectrum of polythioeter prepared in example 1;

(4) FIG. 4 is a .sup.1H NMR spectrum of polythioeter prepared in example 10;

(5) FIG. 5 is a .sup.1H NMR spectrum of polythioeter prepared in example 14.

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS

(6) For better specifically describing the disclosure, the technical solution of the disclosure will be described in detail in combination with drawings and specific embodiments.

(7) In the disclosure, the used catalyst has the following structure, the numbers of initiators having different structures are as shown in the following formulas.

(8) ##STR00001##

Comparative Example 1 COS/PO Copolymerization

(9) Before polymerization reaction, water in a 10 mL autoclave was removed at 110V for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 1 bis(triphenylphosphoranyl) ammonium chloride ([PPN]Cl) were added to the autoclave in sequence; a molar ratio of the catalyst f to propylene oxide (PO) was 1/50; then COS, PO (a molar ratio of COS to PO was 2:1) and 1 mL tetrahydrofuran (THF) were added. Then, the autoclave was closed and put into 60° C. oil bath to react for 24 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1,

(10) The .sup.1H NMR spectrum of the polymer prepared in this comparative example is as shown in FIG. 1. It can be seen from FIG. 1 that the polymerized product is polymonothiocarbonate, and polythioether is not produced, FIG. 1 also shows the peak position and integral area of each hydrogen atom on the chain unit of monothiocarbonate.

Example 1 Synthesis of Polythioether from COS/PO

(11) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst f bis(triphenylphosphoranyl) ammonium chloride ([PPN]Cl) were added to the autoclave in sequence; a molar ratio of the catalyst 1 to propylene oxide (PO) was 1/50; then COS, PO (a molar ratio of COS to PO was 2:1) and 1 mL tetrahydrofuran (THF) were added. Then, the autoclave was closed and put into 80° C. oil bath to react for 5 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

(12) The .sup.1H NMR spectrum of the polymer prepared in this example is as shown in FIG. 2, and .sup.13C NMR spectrum of the polymer prepared in this example is as shown in FIG. 3. It can be seen from FIG. 2 and FIG. 3 that polythioether is successfully synthesized; FIG. 2 also shows the peak position and integral area of each hydrogen atom on the chain unit of thioether.

Example 2 Synthesis of Polythioether from CS.SUB.2./PO

(13) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 2 dodecyltrimethyl ammonium bromide (DTMeAB) were added to the autoclave in sequence; a molar ratio of the catalyst 2 to propylene oxide (PO) was 1/500; then CS.sub.2, PO (a molar ratio of CS.sub.2 to PO was 2:1) and 1 mL tetrahydrofuran (THF) were added. Then, the autoclave was closed and put into 80° C. oil bath to react for 2 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

Example 3 Synthesis of Polythioether from CS.SUB.2./PO

(14) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 2 dodecyltrimethyl ammonium bromide (DTMeAB) were added to the autoclave in sequence; a molar ratio of the catalyst 2 to propylene oxide (PO) was 1/500; then CS.sub.2, PO (a molar ratio of CS.sub.2 to PO was 2:1) and 1 mL tetrahydrofuran (THF) were added. Then, the autoclave was closed and put into 130° C. oil bath to react for 2 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

Example 4 Synthesis of Polythioether from CS.SUB.2./PO

(15) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 2 dodecyltrimethyl ammonium bromide (DTMeAB) were added to the autoclave in sequence; a molar ratio of the catalyst 2 to propylene oxide (PO) was 1/500; then CS.sub.2, PO (a molar ratio of CS.sub.2 to PO was 10:1) and 1 mL tetrahydrofuran (THF) were added. Then, the autoclave was closed and put into 130° C. oil bath to react for 2 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

Example 5 Synthesis of Polythioether from CS.SUB.2./PO

(16) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 2 dodecyltrimethyl ammonium bromide (DTMeAB) were added to the autoclave in sequence; a molar ratio of the catalyst 2 to propylene oxide (PO) was 1/10; then CS.sub.2, PO (a molar ratio of CS.sub.2 to PO was 2:1) and 1 mL tetrahydrofuran (THF) were added. Then, the autoclave was closed and put into 130° C. oil bath to react for 2 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

Example 6 Synthesis of Polythioether from COS/PO

(17) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 3 tetraphenyl phosphonium chloride (PPh.sub.4Cl) were added to the autoclave in sequence; a molar ratio of the catalyst 3 to propylene oxide (PO) was 1/250; then COS, PO (a molar ratio of COS to PO was 2:1) and 1 mL tetrahydrofuran (THF) were added. Then, the autoclave was closed and put into 150° C. oil bath to react for 1 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

Example 7 Synthesis of Polythioether from COS/PO

(18) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 4 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were added to the autoclave in sequence; a molar ratio of the catalyst 4 to propylene oxide (PO) was 1/100; then COS, PO (a molar ratio of COS to PO was 1:1) and 1 mL dimethylformamide (DMF) were added. Then, the autoclave was closed and put into 150° C. oil bath to react for 2 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

Example 8 Synthesis of Polythioether from COS/PO

(19) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 5 sodium methoxide (CH.sub.3ONa) were added to the autoclave in sequence; a molar ratio of the catalyst 5 to propylene oxide (PO) was 1/50; then COS and PO (a molar ratio of COS to PO was 2:1) were added. Then, the autoclave was closed and put into 180° C. oil bath to react for 0.5 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

Example 9 Synthesis of Polythioether from CS.SUB.2./PO

(20) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 6 potassium tert-butoxide (t-BuOK) were added to the autoclave in sequence; a molar ratio of the catalyst 6 to propylene oxide (PO) was 1/5000; then CS.sub.2, PO (a molar ratio of CS.sub.2 to PO was 2:1) and 1 mL tetrahydrofuran (THF) were added. Then, the autoclave was closed and put into 130° C. oil bath to react for 12 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

Example 10 Synthesis of Polythioether from CS.SUB.2./CHO

(21) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 6 potassium tert-butoxide (t-BuOK) were added to the autoclave in sequence; a molar ratio of the catalyst 6 to cyclohexene oxide (CHO) was 1/500; then CS.sub.2, CHO (a molar ratio of CS.sub.2 to CHO was 5:1) and 1 mL tetrahydrofuran (THF) were added. Then, the autoclave was closed and put into 150° C. oil bath to react for 8 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

(22) The .sup.1H NMR spectrum of the polythioether prepared in this example is as shown in FIG. 4. It can be seen from FIG. 4 that polythioether is successfully synthesized; FIG. 4 also shows the peak position and integral area of each hydrogen atom on the chain unit of thioether.

Example 11 Synthesis of Polythioether from CS.SUB.2./PGE

(23) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 1 bis(triphenylphosphoranyl) ammonium chloride ([PPN]Cl) were added to the autoclave in sequence; a molar ratio of the catalyst 1 to phenyl glycidyl ether (PGE) was 1/500; then CS.sub.2, PGE (a molar ratio of CS.sub.2 to PGE was 2:1) and 1 mL tetrahydrofuran (THF) were added. Then, the autoclave was closed and put into 150° C. oil bath to react for 8 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

Example 12 Synthesis of Polythioether from COS/StO

(24) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 2 dodecyltrimethyl ammonium bromide (DTMeAB) were added to the autoclave in sequence; a molar ratio of the catalyst 2 to styrene oxide (StO) was 1/500; then COS, StO (a molar ratio of COS to StO was 2:1) and 1 mL dimethylformamide (THF) were added. Then, the autoclave was closed and put into 150° C. oil bath to react for 12 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

Example 13 Synthesis of Polythioether from CS.SUB.2./E0

(25) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 2 dodecyltrimethyl ammonium bromide (DTMeAB) were added to the autoclave in sequence; a molar ratio of the catalyst 2 to ethylene oxide (EO) was 1/500; then CS.sub.2, EO (a molar ratio of CS.sub.2 to EO was 5:1) and 1 mL trichlorobenzene were added. Then, the autoclave was closed and put into 160° C. oil bath to react for 10 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

Example 14 Synthesis of Polythioether from COS/Benzyl Glycidyl Ether

(26) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 1 bis(triphenylphosphoranyl) ammonium chloride ([PPN]Cl) were added to the autoclave in sequence; a molar ratio of the catalyst 1 to benzyl glycidyl ether was 1/500; then COS, benzyl glycidyl ether (a molar ratio of COS to benzylglycidyl ether was 1:1) and 1 mL toluene were added. Then, the autoclave was closed and put into 150° C. oil bath to react for 8 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

(27) The .sup.1H NMR spectrum of the polythioether prepared in this example is shown in FIG. 5. It can be seen from FIG. 5 that polythioether is successfully synthesized; FIG. 5 shows the peak position and integral area of each hydrogen atom on the chain unit of thioether.

Example 15 Synthesis of Polythioether from COS/OX

(28) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 2 dodecyltrimethyl ammonium bromide (DTMeAB) were added to the autoclave in sequence; a molar ratio of catalyst 2 to OX (oxetane) was 1/500; then COS, OX (a molar ratio of COS to OX was 2:1) and 1 mL trichlorobenzene were added. Then, the autoclave was closed and put into 160° C. oil bath to react for 2 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

Example 16 Synthesis of Polythioether from CS.SUB.2./3-Chloromethyl-3-Methyl Oxetane

(29) Before polymerization reaction, water in a 10 mL autoclave was removed at 110° C. for about 2 hours, and the autoclave was cooled to room temperature in a dryer; certain amounts of catalyst 1 bis(triphenylphosphoranyl) ammonium chloride ([PPN]Cl) were added to the autoclave in sequence; a molar ratio of the catalyst 1 to 3-chloromethyl-3-methyl oxetane was 1/500; then CS.sub.2, 3-chloromethyl-3-methyl oxetane (a molar ratio of CS.sub.2 to 3-chloromethyl-3-methyl oxetane was 2:1) and 1 mL dimethylformamide (DMF) were added. Then, the autoclave was closed and put into 160° C. oil bath to react for 1 h under the self-generated pressure. After the reaction was ended, the autoclave was cooled to room temperature. The crude product was dissolved with tetrahydrofuran, and then the polymer was precipitated out in the mixture of ethanol/deionized water/hydrochloric acid. The polymer was repeatedly washed three times and dried in vacuum to constant weight. The molecular weight and molecular weight distribution of the polymer were determined by gel chromatography. The test results are shown in Table 1.

(30) TABLE-US-00001 Cl T C1/  t M.sub.n.sup.7 Number (° C.)   .sup.6 (h) (kg/mol) PDI.sup.8 Comparative COS PO 60 1 1/50 2/1 THF 24 — — example 1 .sup.9 Example COS PO 80 1 1/50 2/1 THF 5.0 1.0 1.6 1 Example CS.sub.2 PO 80 2 1/500 2/1 THF 2.0 5.5 2.0 2 Example CS.sub.2 PO 130 2 1/500 2/1 THF 2.0 78.5 1.1 3 Example CS.sub.2 PO 130 2 1/500 10/1 THF 2.0 8.5 1.5 4 Example CS.sub.2 PO 130 2 1/10 2/1 THF 2.0 5.5 1.1 5 Example COS PO 150 3 1/250 2/1 THF 1.0 100.0 1.3 6 Example COS PO 150 4 1/100 1/1 DMF 2.0 56.8 1.5 7 Example COS PO 180 5 1/50 2/1 — 0.5 88.0 1.1 8 Example CS.sub.2 PO 130 6 1/5000 2/1 THF 12.0 6.0 1.4 9 Example CS.sub.2 CHO 150 6 1/500 5/1 THF 8.0 10.0 1.2 10 Example CS.sub.2 PGE 150 1 1/500 2/1 THF 8.0 13.5 1.3 11 Example COS StO 150 2 1/500 2/1 THF 12.0 13.0 1.2 12 Example CS.sub.2 EO 160 2 1/500 5/1 Trichloro 10.0 53.0 1.5 13 benzene Example COS Benzyl 150 1 1/500 1/1 Toluene 8.0 5.0 1.4 14 glycidyl ether Example COS OX 160 2 1/500 2/1 Trichloro 2.0 55.0 1.5 15 benzene Example CS.sub.2 3-chloromethy 160 1 1/500 2/1 DMF 1.0 45.3 1.4 16 1-3-methyl oxetane .sup.1 types of sulfur-carbon compounds; .sup.2 types of oxygen-containing compounds, which can be completely converted; .sup.3 types of catalysts: 1 is bis(triphenylphosphoranyl) ammonium chloride ([PPN]Cl), 2 is dodecyltrimethyl ammonium bromide (DTMeAB), 3 tetraphenyl phosphonium chloride (PPh.sub.4Cl), 4 is 1,8-diazabicyclo[5.4.0]undec-7-carbene (DBU), 5 sodium methoxide (CH.sub.3ONa), 6 potassium tert-butoxide (t-BuOK); .sup.4 a molar ratio of catalyst to epoxide; .sup.5 a molar ratio of sulfur-carbon compound to oxygen-containing monomer; .sup.6 types of solvents: THF: tetrahydrofuran , DMF: dimethylforrnamide, trichlorobenzene, toluene; .sup.7 Mn: number average molecular weight, determined by gel permeation chromatography; .sup.8 PDI: molecular weight distribution, determined by gel permeation chromatography; .sup.9 temperature below 80° C., polythioether is not generated, and the product is polythiocarbonate.

(31) It can be seen from the above results that:

(32) Examples 1˜16 are results for generating polythioether by catalyzing polymerization of COS or CS.sub.2 and epoxide with different catalysts. It can be seen from the above results that this synthesis method has high activity (i.e., oxygen-containing compounds are all completely converted) and universality.

(33) The above descriptions are only several specific embodiments of the disclosure. It should be noted that, persons of ordinary skill in the art can make many deformations and improvements, all the deformations or improvements which do not go beyond the claims should be deemed as the protective scope of the disclosure.