JPS6159335B2 - - Google Patents
Info
- Publication number
- JPS6159335B2 JPS6159335B2 JP10091580A JP10091580A JPS6159335B2 JP S6159335 B2 JPS6159335 B2 JP S6159335B2 JP 10091580 A JP10091580 A JP 10091580A JP 10091580 A JP10091580 A JP 10091580A JP S6159335 B2 JPS6159335 B2 JP S6159335B2
- Authority
- JP
- Japan
- Prior art keywords
- polyester
- anhydride
- acid
- reaction
- added
- 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 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 14
- 238000006068 polycondensation reaction Methods 0.000 claims description 11
- 150000002736 metal compounds Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- WWQUDCOYJDOYEZ-UHFFFAOYSA-N oxo(sulfocarbonyloxy)methanesulfonic acid Chemical compound OS(=O)(=O)C(=O)OC(=O)S(O)(=O)=O WWQUDCOYJDOYEZ-UHFFFAOYSA-N 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- NCYNKWQXFADUOZ-UHFFFAOYSA-N 1,1-dioxo-2,1$l^{6}-benzoxathiol-3-one Chemical compound C1=CC=C2C(=O)OS(=O)(=O)C2=C1 NCYNKWQXFADUOZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- -1 polyethylene terephthalate Polymers 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- ADFVYWCDAKWKPH-UHFFFAOYSA-N 4-ethoxycarbonylbenzoic acid Chemical compound CCOC(=O)C1=CC=C(C(O)=O)C=C1 ADFVYWCDAKWKPH-UHFFFAOYSA-N 0.000 description 1
- BMBBTGNMHDPAGE-UHFFFAOYSA-N 4-methoxy-2-(5-methoxy-2-sulfobenzoyl)oxycarbonylbenzenesulfonic acid Chemical compound COC=1C=CC(=C(C(=O)OC(C2=C(C=CC(=C2)OC)S(=O)(=O)O)=O)C=1)S(=O)(=O)O BMBBTGNMHDPAGE-UHFFFAOYSA-N 0.000 description 1
- WECVZMYTLWOTQL-UHFFFAOYSA-N 5-methyl-2-(4-methyl-2-sulfobenzoyl)oxycarbonylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(C)=CC=C1C(=O)OC(=O)C1=CC=C(C)C=C1S(O)(=O)=O WECVZMYTLWOTQL-UHFFFAOYSA-N 0.000 description 1
- GBTDIDYMOCNBSX-UHFFFAOYSA-N 6-(3,4-dimethyl-2-sulfobenzoyl)oxycarbonyl-2,3-dimethylbenzenesulfonic acid Chemical compound CC1=C(C(=C(C(=O)OC(C2=C(C(=C(C=C2)C)C)S(=O)(=O)O)=O)C=C1)S(=O)(=O)O)C GBTDIDYMOCNBSX-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- GFTOBARZRJSYBP-UHFFFAOYSA-N C1=C2C(=CC(=C1S(=O)(=O)O)C(=O)OC2=O)S(=O)(=O)O Chemical compound C1=C2C(=CC(=C1S(=O)(=O)O)C(=O)OC2=O)S(=O)(=O)O GFTOBARZRJSYBP-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- MQUHQBCJMWUGFK-UHFFFAOYSA-N OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C2=C1C(=O)OC2=O Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C2=C1C(=O)OC2=O MQUHQBCJMWUGFK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZPKKWIKMTCYHGP-UHFFFAOYSA-N S(=O)(=O)(O)C1=C2C=C(C(=O)OC2=O)C(=C1)S(=O)(=O)O Chemical compound S(=O)(=O)(O)C1=C2C=C(C(=O)OC2=O)C(=C1)S(=O)(=O)O ZPKKWIKMTCYHGP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 150000002291 germanium compounds Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000002697 manganese compounds Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10091580A JPS5725326A (en) | 1980-07-23 | 1980-07-23 | Production of polyester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10091580A JPS5725326A (en) | 1980-07-23 | 1980-07-23 | Production of polyester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5725326A JPS5725326A (en) | 1982-02-10 |
| JPS6159335B2 true JPS6159335B2 (ko) | 1986-12-16 |
Family
ID=14286626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10091580A Granted JPS5725326A (en) | 1980-07-23 | 1980-07-23 | Production of polyester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5725326A (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4976879A (en) * | 1987-10-05 | 1990-12-11 | The Procter & Gamble Company | Sulfoaroyl end-capped ester oligomers suitable as soil-release agents in detergent compositions and fabric-conditioner articles |
| US5182043A (en) * | 1989-10-31 | 1993-01-26 | The Procter & Gamble Company | Sulfobenzoyl end-capped ester oligomers useful as soil release agents in granular detergent compositions |
| US5196133A (en) * | 1989-10-31 | 1993-03-23 | The Procter & Gamble Company | Granular detergent compositions containing peroxyacid bleach and sulfobenzoyl end-capped ester oligomers useful as soil-release agents |
| US5256168A (en) * | 1989-10-31 | 1993-10-26 | The Procter & Gamble Company | Sulfobenzoyl end-capped ester oligomers useful as soil release agents in granular detergent compositions |
| JPH04122505A (ja) * | 1990-09-10 | 1992-04-23 | Saburo Watanabe | 多軸ボール盤等の回転軸間距離及び回転軸の角度表示装置 |
-
1980
- 1980-07-23 JP JP10091580A patent/JPS5725326A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5725326A (en) | 1982-02-10 |
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