GB964711A - Modified polyesters and the method of preparation thereof - Google Patents
Modified polyesters and the method of preparation thereofInfo
- Publication number
- GB964711A GB964711A GB11179/61A GB1117961A GB964711A GB 964711 A GB964711 A GB 964711A GB 11179/61 A GB11179/61 A GB 11179/61A GB 1117961 A GB1117961 A GB 1117961A GB 964711 A GB964711 A GB 964711A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dicarbomethoxyphenyl
- acid
- sulphonate
- carboethoxyphenyl
- benzenesulphonate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920000728 polyester Polymers 0.000 title abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 11
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 4
- ZYFZMOKLDYGMQD-UHFFFAOYSA-N 4-benzyl-1-ethoxycarbonylcyclohexa-2,4-diene-1-sulfonic acid Chemical compound CCOC(=O)C1(CC=C(C=C1)CC2=CC=CC=C2)S(=O)(=O)O ZYFZMOKLDYGMQD-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 125000000524 functional group Chemical group 0.000 abstract 3
- ZKMSHLUTNALYQQ-UHFFFAOYSA-N 4-[[3,5-bis(methoxycarbonyl)phenyl]methyl]benzenesulfonic acid Chemical compound COC(=O)C1=CC(=CC(=C1)CC2=CC=C(C=C2)S(=O)(=O)O)C(=O)OC ZKMSHLUTNALYQQ-UHFFFAOYSA-N 0.000 abstract 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 2
- QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-UHFFFAOYSA-N 0.000 abstract 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 abstract 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- QDJDCJNIDISNLN-UHFFFAOYSA-N dimethyl 5-(benzenesulfonyloxy)benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(OS(=O)(=O)C=2C=CC=CC=2)=C1 QDJDCJNIDISNLN-UHFFFAOYSA-N 0.000 abstract 2
- 239000003607 modifier Substances 0.000 abstract 2
- -1 sulphonic acid ester Chemical class 0.000 abstract 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 abstract 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 1
- AKOGNYJNGMLDOA-UHFFFAOYSA-N (4-acetyloxyphenyl) acetate Chemical compound CC(=O)OC1=CC=C(OC(C)=O)C=C1 AKOGNYJNGMLDOA-UHFFFAOYSA-N 0.000 abstract 1
- WJCRIPKQEHWWRB-UHFFFAOYSA-N 1-(4-methoxycarbonylphenyl)ethanesulfonic acid Chemical compound CC(C1=CC=C(C=C1)C(=O)OC)S(=O)(=O)O WJCRIPKQEHWWRB-UHFFFAOYSA-N 0.000 abstract 1
- UIYJVFQLEXLBJB-UHFFFAOYSA-N 1-acetyloxy-5-phenyl-4-sulfocyclohexa-2,4-diene-1-carboxylic acid Chemical compound CC(=O)OC1(CC(=C(C=C1)S(=O)(=O)O)C2=CC=CC=C2)C(=O)O UIYJVFQLEXLBJB-UHFFFAOYSA-N 0.000 abstract 1
- KQOBRCVZRQKTLB-UHFFFAOYSA-N 2,6-bis(methoxycarbonyl)-4-methylbenzenesulfonic acid Chemical compound CC1=CC(=C(C(=C1)C(=O)OC)S(=O)(=O)O)C(=O)OC KQOBRCVZRQKTLB-UHFFFAOYSA-N 0.000 abstract 1
- UJIHXQJNDVKDDO-UHFFFAOYSA-N 2-[3,5-bis(methoxycarbonyl)phenyl]-4-chlorobenzenesulfonic acid Chemical compound COC(=O)C1=CC(=CC(=C1)C2=C(C=CC(=C2)Cl)S(=O)(=O)O)C(=O)OC UJIHXQJNDVKDDO-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- BJBBXRARLWWAEZ-UHFFFAOYSA-N [3-acetyloxy-5-(benzenesulfonyloxy)phenyl] acetate Chemical compound C1(=CC=CC=C1)S(=O)(=O)OC1=CC(=CC(=C1)OC(C)=O)OC(C)=O BJBBXRARLWWAEZ-UHFFFAOYSA-N 0.000 abstract 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- QUNWXPCJAGERII-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;potassium Chemical compound [K].OC(=O)C1=CC=CC(C(O)=O)=C1 QUNWXPCJAGERII-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- ZCWJUJRUHKKIGF-UHFFFAOYSA-N dimethyl 2-benzylsulfonyloxybenzene-1,4-dicarboxylate Chemical compound C(C1=CC=CC=C1)S(=O)(=O)OC1=C(C=CC(=C1)C(=O)OC)C(=O)OC ZCWJUJRUHKKIGF-UHFFFAOYSA-N 0.000 abstract 1
- DOSDTCPDBPRFHQ-UHFFFAOYSA-N dimethyl 5-hydroxybenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(O)=CC(C(=O)OC)=C1 DOSDTCPDBPRFHQ-UHFFFAOYSA-N 0.000 abstract 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 abstract 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 abstract 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 abstract 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 abstract 1
- 229940043351 ethyl-p-hydroxybenzoate Drugs 0.000 abstract 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- YQYRQRUZQNRJIW-UHFFFAOYSA-N methyl 4-(4-methoxycarbonylphenyl)sulfonylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1S(=O)(=O)C1=CC=C(C(=O)OC)C=C1 YQYRQRUZQNRJIW-UHFFFAOYSA-N 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/24—Polysulfonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
Abstract
Example 1: 5-hydroxy-iso-phthalic acid was prepared from potassium-3,5-dicarboxy benzene sulphonate and potassium hydroxide, esterified with methanol and the resulting dimethyl-5-hydroxyisophthalate was reacted with a p-toluenesulphonyl chloride to yield 3,5-dicarbomethoxy-p-toluenesulphonate. Example 16: Reaction of ethyl-p-hydroxybenzoate with p-toluenesulphonyl chloride yielded p-carboethoxyphenyl-p-toluenesulphonate.ALSO:Polyesters are modified with 0.1 to 20 mol. per cent based on the acid component of the residues of sulphonic acid esters of formula (X-Y)n-Y in which X and Y each represent the same or different organic radicals, at least one of which contains at least one ester-forming functional group and the total number of functional groups is 1 or 2; Z is -OSO2- or -SO2O-, is 1, 2, 3 or 4 and when n = 1 the organic radical attached to O is aromatic, and when n = 2, 3 or 4, X is the same or different organic radical. Ester-forming functional groups mentioned are hydroxyl, acyloxy, carboxyl, carboxyl esterified with alkyl or aryl, or carbohalide. Suitable sulphur-containing modifiers are listed, mostly for the cases when n = 1 or 2. The modifiers may be added at any stage of the conventional polyester-forming reaction, preferably towards the end thereof. Conventional additives may be included, e.g. delustrants such as TiO2, and stabilizers such as phosphorous acid. Conventional catalysts may be employed. In examples 1 to 10, polyesters were prepared from ethylene glycol, terephthalic acid and (1) 3,5-dicarbomethoxyphenyl-p-toluene sulphonate, (2) 3,5-dicarbomethoxyphenyl benzene sulphonate, (3) p-carboethoxyphenyl-p-toluene sulphonate (4), (5) p-carboxyphenyl-p-acetoxybenzenesulphonate. (6) di-p-carboethoxyphenyl-m-benzene-disulphonate, (7) p-phenylene-di-m-carbomethoxy benzenesulphonate. (8) 1,4-cyclohexylene-di-p-carbomethoxybenzenesulphonate, (9) tri-toluene-sulphonic acid ester of pentaerythritol, (10) tetramethane sulphonic acid ester of b ,b -bis(3,4-di-hydroxyphenyl)-glutaric acid, (11) 3,5-dicarbomethoxyphenyl-p-toluenesulphonate. Polyesters were also prepared from (12) dimethyl terephthalate, 1,4-dihydroxymethyl cyclohexane and 2,5-dicarbomethoxyphenyl toluene sulphonate in presence of TiO2. (13) methyl-p-b -hydroxyethoxybenzoate, ethylene glycol and 2-b -hydroxyethoxy-5-carbomethoxyphenyl benzenesulphonate in presence of triphenyl phosphite. (14) dimethyl terephthalate, dimethyl diphenyl-4-41-dicarboxylate, ethylene glycol and 3,5-dicarbomethoxyphenyl-p-chlorobenzenesulphonate. (15) p-phenylene diacetate, adipic acid, and 3,5-diacetoxyphenyl benzenesulphonate. This polymer was reacted with another from dimethyl terephthalate and ethylene glycol. (16) bis-(4-carbomethoxyphenyl sulphone, butylene glycol and p-carboethoxyphenyl-p-toluenesulphonate. (17) diphenyl carbonate, bisphenol A, and 3,5-dicarbomethoxyphenyl benzenesulphonate. (18) bis(4-carbomethoxyphenyl)sulphone, tetramethylene glycol and p-carbomethoxyphenylethane sulphonate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1113360 | 1960-03-31 | ||
| FR857434A FR1311130A (en) | 1960-03-31 | 1961-03-31 | Modified polyesters and process for preparing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB964711A true GB964711A (en) | 1964-07-22 |
Family
ID=26189930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11179/61A Expired GB964711A (en) | 1960-03-31 | 1961-03-27 | Modified polyesters and the method of preparation thereof |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1311130A (en) |
| GB (1) | GB964711A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1816163A1 (en) * | 1968-01-03 | 1969-07-31 | Eastman Kodak Co | Linear polyesters dispersible in water |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2732556A1 (en) | 1977-07-19 | 1979-02-01 | Bayer Ag | METHOD FOR MANUFACTURING FLAME RETARDANT POLYCARBONATES |
-
1961
- 1961-03-27 GB GB11179/61A patent/GB964711A/en not_active Expired
- 1961-03-31 FR FR857434A patent/FR1311130A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1816163A1 (en) * | 1968-01-03 | 1969-07-31 | Eastman Kodak Co | Linear polyesters dispersible in water |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1311130A (en) | 1962-12-07 |
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