DE1694549C3 - Stabilisierung linearer Polyester oder Copolyester gegen Wärmeabbau - Google Patents
Stabilisierung linearer Polyester oder Copolyester gegen WärmeabbauInfo
- Publication number
- DE1694549C3 DE1694549C3 DE1694549A DEK0064096A DE1694549C3 DE 1694549 C3 DE1694549 C3 DE 1694549C3 DE 1694549 A DE1694549 A DE 1694549A DE K0064096 A DEK0064096 A DE K0064096A DE 1694549 C3 DE1694549 C3 DE 1694549C3
- Authority
- DE
- Germany
- Prior art keywords
- thermal stability
- copolyesters
- polyester
- linear polyesters
- polyesters
- 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 claims description 18
- 229920001634 Copolyester Polymers 0.000 title claims description 6
- 230000015556 catabolic process Effects 0.000 title claims description 6
- 238000006731 degradation reaction Methods 0.000 title claims description 6
- 230000006641 stabilisation Effects 0.000 title description 3
- 238000011105 stabilization Methods 0.000 title description 3
- 238000006068 polycondensation reaction Methods 0.000 claims description 10
- 239000003381 stabilizer Substances 0.000 claims description 9
- 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 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- -1 diaryl ester Chemical class 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 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 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- JDRJCBXXDRYVJC-UHFFFAOYSA-N OP(O)O.N.N.N Chemical compound OP(O)O.N.N.N JDRJCBXXDRYVJC-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 238000010525 oxidative degradation reaction Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 150000003018 phosphorus compounds Chemical class 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- ORICWOYODJGJMY-UHFFFAOYSA-N dibutyl(phenyl)phosphane Chemical compound CCCCP(CCCC)C1=CC=CC=C1 ORICWOYODJGJMY-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
- 239000001639 calcium acetate Substances 0.000 description 2
- 235000011092 calcium acetate Nutrition 0.000 description 2
- 229960005147 calcium acetate Drugs 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- QXKPLZDCTKREIA-UHFFFAOYSA-N diphenoxy(phenyl)phosphane Chemical compound C=1C=CC=CC=1OP(C=1C=CC=CC=1)OC1=CC=CC=C1 QXKPLZDCTKREIA-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 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
- 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
- C08G63/87—Non-metals or inter-compounds thereof
-
- 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
- C08K5/49—Phosphorus-containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1694549A DE1694549C3 (de) | 1967-12-04 | 1967-12-04 | Stabilisierung linearer Polyester oder Copolyester gegen Wärmeabbau |
| NL6816728A NL6816728A (enExample) | 1967-12-04 | 1968-11-22 | |
| BE724802D BE724802A (enExample) | 1967-12-04 | 1968-12-02 | |
| LU57436D LU57436A1 (enExample) | 1967-12-04 | 1968-12-02 | |
| FR1593914D FR1593914A (enExample) | 1967-12-04 | 1968-12-02 | |
| US780559A US3609118A (en) | 1967-12-04 | 1968-12-02 | Polyesters stabilized with a phosphonite |
| GB57354/68A GB1248770A (en) | 1967-12-04 | 1968-12-03 | Improvements in and relating to thermostabilized linear polyesters and copolyesters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1694549A DE1694549C3 (de) | 1967-12-04 | 1967-12-04 | Stabilisierung linearer Polyester oder Copolyester gegen Wärmeabbau |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1694549A1 DE1694549A1 (de) | 1971-07-15 |
| DE1694549B2 DE1694549B2 (de) | 1979-06-13 |
| DE1694549C3 true DE1694549C3 (de) | 1980-02-07 |
Family
ID=7231451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1694549A Expired DE1694549C3 (de) | 1967-12-04 | 1967-12-04 | Stabilisierung linearer Polyester oder Copolyester gegen Wärmeabbau |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3609118A (enExample) |
| BE (1) | BE724802A (enExample) |
| DE (1) | DE1694549C3 (enExample) |
| FR (1) | FR1593914A (enExample) |
| GB (1) | GB1248770A (enExample) |
| LU (1) | LU57436A1 (enExample) |
| NL (1) | NL6816728A (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1372528A (en) * | 1970-10-22 | 1974-10-30 | Sandoz Ltd | Benzene phosphonous acid compounds their production and use as stabilizers for organic materials |
| US3953388A (en) * | 1973-01-02 | 1976-04-27 | General Electric Company | Thermally stable polycarbonate |
| US3978020A (en) * | 1973-01-02 | 1976-08-31 | General Electric Company | Thermally stable polycarbonate |
| US4250281A (en) * | 1979-03-21 | 1981-02-10 | Eastman Kodak Company | Melt process for preparing copolyesters using triarylphosphine catalysts |
| US4233207A (en) * | 1979-07-09 | 1980-11-11 | Ciba-Geigy Corporation | Hydrolytically stable ortho-alkylated phenyl phosphonites and stabilized compositions |
| USRE32046E (en) * | 1980-07-12 | 1985-12-10 | Bayer Aktiengesellschaft | Solutions for stabilizing thermoplastic polycarbonates |
| DE3026503A1 (de) * | 1980-07-12 | 1982-02-18 | Bayer Ag, 5090 Leverkusen | Stabilisatorloesung, ihre verwendung zur stabilisierung von thermoplastischen polycarbonaten sowie stabilisierte thermoplastische polycarbonate |
| DE19643279A1 (de) * | 1996-10-21 | 1998-04-23 | Basf Ag | Flammgeschützte Formmassen |
| US6107375A (en) * | 1998-10-08 | 2000-08-22 | Bayer Corporation | Hydrolysis-stable polycarbonate molding composition |
| NL2002382C2 (en) * | 2008-12-30 | 2010-07-01 | Furanix Technologies Bv | A process for preparing a polymer having a 2,5-furandicarboxylate moiety within the polymer backbone and such (co)polymers. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055861A (en) * | 1958-02-19 | 1962-09-25 | Union Carbide Corp | Stabilized acrylonitrile vinyl or vinylidene copolymer solutions |
| US3053809A (en) * | 1958-04-15 | 1962-09-11 | Celanese Corp | Phosphine-metal compound catalyst |
-
1967
- 1967-12-04 DE DE1694549A patent/DE1694549C3/de not_active Expired
-
1968
- 1968-11-22 NL NL6816728A patent/NL6816728A/xx unknown
- 1968-12-02 FR FR1593914D patent/FR1593914A/fr not_active Expired
- 1968-12-02 US US780559A patent/US3609118A/en not_active Expired - Lifetime
- 1968-12-02 BE BE724802D patent/BE724802A/xx unknown
- 1968-12-02 LU LU57436D patent/LU57436A1/xx unknown
- 1968-12-03 GB GB57354/68A patent/GB1248770A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6816728A (enExample) | 1969-06-06 |
| DE1694549B2 (de) | 1979-06-13 |
| GB1248770A (en) | 1971-10-06 |
| US3609118A (en) | 1971-09-28 |
| BE724802A (enExample) | 1969-06-02 |
| FR1593914A (enExample) | 1970-06-01 |
| LU57436A1 (enExample) | 1970-06-04 |
| DE1694549A1 (de) | 1971-07-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0827518B1 (de) | Verfahren zur herstellung von polyestern unter verwendung von titanhaltigen katalysator-inhibitor-kombinationen | |
| DE2454189A1 (de) | Verfahren zur herstellung schwer entflammbarer linearer polyester | |
| CH640547A5 (de) | Verfahren zur herstellung eines linearen homo- oder copolyesters mit verbesserter hitzestabilitaet. | |
| DE1694549C3 (de) | Stabilisierung linearer Polyester oder Copolyester gegen Wärmeabbau | |
| AT259232B (de) | Verfahren zur Herstellung von faser und filmbildenden Polyestern | |
| DE2045914A1 (de) | Verfahren zur Herstellung von Polyestern des 1,4-ButandiolS· | |
| DE1669841B2 (de) | Verfahren zur herstellung von mercaptogruppen enthaltenden organozinnverbindungen | |
| DE2614980A1 (de) | Verfahren zur herstellung von gesaettigten, hochmolekularen polyestern | |
| DE2802486B2 (de) | Verfahren zur Herstellung von fadenbildenden Polyestern | |
| DE1694550B2 (de) | Stabilisierung linearer Polyester oder Copolyester gegen Wärmeabbau | |
| DE1520079B2 (de) | Verfahren zur herstellung hochpolymerer polymethylenterephthalate | |
| DE1495777B2 (de) | Verfahren zur herstellung von linearen hochmolekularen poly estern | |
| DE1950553A1 (de) | Verfahren zur Herstellung von Polyaethylenterephthalat | |
| DE1545024A1 (de) | Verfahren zur Herstellung von filmbildenden Polyestern | |
| DE2224088A1 (enExample) | ||
| DE1694548B2 (enExample) | ||
| DE2633392C3 (de) | Neue, hydrolysestabile Phosphite von Polyalkoholen, ihre Herstellung und Verwendung | |
| DE2124129C2 (de) | Verfahren zur Herstellung von Polyestern mit verbesserter Anfärbbarkeit | |
| DE1124475B (de) | Verfahren zur Herstellung von Terephthalsaeureglykolestern | |
| AT251291B (de) | Verfahren zur Herstellung von faser- und filmbildenden Polyestern | |
| CH635814A5 (de) | Umesterungsverfahren. | |
| DE2166285C3 (de) | Verfahren zur Herstellung linearer Polyester | |
| DE1520079C (de) | Verfahren zur Herstellung hochpolymerer Polymethylenterephthalate | |
| DE1301557B (de) | Verfahren zur Herstellung von Polyestern, deren Polyestereinheit wenigstens aus 70% Polyaethylenterephthalat gebildet wird | |
| DE1544977A1 (de) | Verfahren zur Herstellung von Polyesterharzen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |