DE3842945C1 - - Google Patents
Info
- Publication number
- DE3842945C1 DE3842945C1 DE3842945A DE3842945A DE3842945C1 DE 3842945 C1 DE3842945 C1 DE 3842945C1 DE 3842945 A DE3842945 A DE 3842945A DE 3842945 A DE3842945 A DE 3842945A DE 3842945 C1 DE3842945 C1 DE 3842945C1
- Authority
- DE
- Germany
- Prior art keywords
- tert
- butyl
- stabilized
- polyethers
- bhp
- 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 - Lifetime
Links
- 229920000570 polyether Polymers 0.000 claims abstract description 21
- 229920005862 polyol Polymers 0.000 claims abstract description 14
- 150000003077 polyols Chemical class 0.000 claims abstract description 14
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 13
- 239000003381 stabilizer Substances 0.000 claims abstract description 10
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003963 antioxidant agent Substances 0.000 abstract description 6
- 229920002635 polyurethane Polymers 0.000 abstract description 5
- 239000004814 polyurethane Substances 0.000 abstract description 5
- 230000000087 stabilizing effect Effects 0.000 abstract description 3
- 230000003078 antioxidant effect Effects 0.000 abstract description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 7
- 238000002845 discoloration Methods 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 238000004383 yellowing Methods 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 150000002990 phenothiazines Chemical class 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- YEXOWHQZWLCHHD-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1O YEXOWHQZWLCHHD-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 101100346656 Drosophila melanogaster strat gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000006261 foam material Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- -1 phenolic carboxylic acids Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyethers (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3842945A DE3842945C1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-12-21 | 1988-12-21 | |
| CA002004289A CA2004289A1 (en) | 1988-12-21 | 1989-11-30 | Use of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid for stabilizing polyether polyols |
| DE89122653T DE58905541D1 (de) | 1988-12-21 | 1989-12-08 | Verwendung von 3,5-Di-tert, butyl-4-hydroxyphenylpropionsäure zur Stabilisierung von Polyetherpolyolen. |
| ES89122653T ES2058455T3 (es) | 1988-12-21 | 1989-12-08 | Empleo del acido 3,5-di-terc.-butil-4-hidroxifenilpropionico para estabilizar polieterpolioles. |
| AT89122653T ATE94191T1 (de) | 1988-12-21 | 1989-12-08 | Verwendung von 3,5-di-tert, butyl-4hydroxyphenylpropions|urezur stabilisierung von polyetherpolyolen. |
| EP89122653A EP0374621B1 (de) | 1988-12-21 | 1989-12-08 | Verwendung von 3,5-Di-tert, butyl-4-hydroxyphenylpropionsäure zur Stabilisierung von Polyetherpolyolen |
| MX018661A MX170374B (es) | 1988-12-21 | 1989-12-11 | Metodo para estabilizar polioles de dolieter |
| US07/450,894 US5006599A (en) | 1988-12-21 | 1989-12-14 | Use of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid for stabilizing polyether polyols |
| JP1327488A JPH02222448A (ja) | 1988-12-21 | 1989-12-19 | ３，５―ジ―第３ブチル―４―ヒドロキシフエニルプロピオン酸のポリエーテルポリオール安定化への使用 |
| BR898906601A BR8906601A (pt) | 1988-12-21 | 1989-12-20 | Aplicacao de acido 3,5-di-terc.-butil-4-hidroxifenilpropionico,processo para a estabilizacao de um polieter-poliol,composicoes estabilizadas e processos para preparacao de poliuretanas |
| DK649789A DK649789A (da) | 1988-12-21 | 1989-12-20 | Stabilisator for polyetherpolyoler |
| ZA899760A ZA899760B (en) | 1988-12-21 | 1989-12-20 | Use of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid for stabilizing polyether polyols |
| AU47181/89A AU625232B2 (en) | 1988-12-21 | 1989-12-21 | Use of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid for stabilizing polyether polyols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3842945A DE3842945C1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-12-21 | 1988-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3842945C1 true DE3842945C1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-02-15 |
Family
ID=6369668
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3842945A Expired - Lifetime DE3842945C1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-12-21 | 1988-12-21 | |
| DE89122653T Expired - Fee Related DE58905541D1 (de) | 1988-12-21 | 1989-12-08 | Verwendung von 3,5-Di-tert, butyl-4-hydroxyphenylpropionsäure zur Stabilisierung von Polyetherpolyolen. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE89122653T Expired - Fee Related DE58905541D1 (de) | 1988-12-21 | 1989-12-08 | Verwendung von 3,5-Di-tert, butyl-4-hydroxyphenylpropionsäure zur Stabilisierung von Polyetherpolyolen. |
Country Status (12)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19843730A1 (de) * | 1998-09-24 | 2000-03-30 | Sueddeutsche Kalkstickstoff | Stabilisierte, wasserlösliche Polymerpulver auf Basis von Polyoxyalkylenglykol-Carboxylaten und Verfahren zu deren Herstellung |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5219892A (en) * | 1992-06-16 | 1993-06-15 | R. T. Vanderbilt Company, Inc. | Liquid stabilizer compositions for polyols and polyurethane foam |
| US5695689A (en) * | 1994-10-04 | 1997-12-09 | Bayer Aktiengesellschaft | Polyether polyols stabilized with tocopherol |
| JP5456267B2 (ja) * | 2008-03-13 | 2014-03-26 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | 室温硬化性ポリマー組成物およびその製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2557619A1 (de) * | 1974-12-30 | 1976-07-01 | Eurane Europ Polyurethan | Stabilisierte polyaetherpolyole |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3763093A (en) * | 1970-04-27 | 1973-10-02 | Goodrich Co B F | Alkylhydroxyphenylcarboalkoxy substituted nitrogen heterocycles as stabilizers against oxidative thermal and photochemical degradation of organic materials |
| US3723489A (en) * | 1971-02-25 | 1973-03-27 | Ciba Geigy Corp | Metal derivatives of 3,5-di-t-butyl-4-hydroxyphenyl propionic acid |
| US3729441A (en) * | 1971-11-04 | 1973-04-24 | Jefferson Chem Co Inc | Stabilized high molecular weight poly(ethylene oxide) |
| US4007230A (en) * | 1975-02-24 | 1977-02-08 | The Dow Chemical Company | Antioxidant composition for stabilizing polyols |
| JPS56152863A (en) * | 1980-04-28 | 1981-11-26 | Adeka Argus Chem Co Ltd | Synthetic resin composition |
| US4444676A (en) * | 1983-04-01 | 1984-04-24 | Atlantic Richfield Company | Stabilized polyoxyalkylene polyether polyols and polyurethane foams prepared therefrom |
-
1988
- 1988-12-21 DE DE3842945A patent/DE3842945C1/de not_active Expired - Lifetime
-
1989
- 1989-11-30 CA CA002004289A patent/CA2004289A1/en not_active Abandoned
- 1989-12-08 AT AT89122653T patent/ATE94191T1/de not_active IP Right Cessation
- 1989-12-08 DE DE89122653T patent/DE58905541D1/de not_active Expired - Fee Related
- 1989-12-08 EP EP89122653A patent/EP0374621B1/de not_active Expired - Lifetime
- 1989-12-08 ES ES89122653T patent/ES2058455T3/es not_active Expired - Lifetime
- 1989-12-11 MX MX018661A patent/MX170374B/es unknown
- 1989-12-14 US US07/450,894 patent/US5006599A/en not_active Expired - Fee Related
- 1989-12-19 JP JP1327488A patent/JPH02222448A/ja active Pending
- 1989-12-20 DK DK649789A patent/DK649789A/da not_active Application Discontinuation
- 1989-12-20 BR BR898906601A patent/BR8906601A/pt not_active IP Right Cessation
- 1989-12-20 ZA ZA899760A patent/ZA899760B/xx unknown
- 1989-12-21 AU AU47181/89A patent/AU625232B2/en not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2557619A1 (de) * | 1974-12-30 | 1976-07-01 | Eurane Europ Polyurethan | Stabilisierte polyaetherpolyole |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19843730A1 (de) * | 1998-09-24 | 2000-03-30 | Sueddeutsche Kalkstickstoff | Stabilisierte, wasserlösliche Polymerpulver auf Basis von Polyoxyalkylenglykol-Carboxylaten und Verfahren zu deren Herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| MX170374B (es) | 1993-08-18 |
| AU4718189A (en) | 1990-06-28 |
| AU625232B2 (en) | 1992-07-02 |
| DE58905541D1 (de) | 1993-10-14 |
| EP0374621B1 (de) | 1993-09-08 |
| US5006599A (en) | 1991-04-09 |
| BR8906601A (pt) | 1990-09-04 |
| DK649789D0 (da) | 1989-12-20 |
| EP0374621A3 (de) | 1991-05-29 |
| JPH02222448A (ja) | 1990-09-05 |
| CA2004289A1 (en) | 1990-06-21 |
| ATE94191T1 (de) | 1993-09-15 |
| DK649789A (da) | 1990-06-22 |
| EP0374621A2 (de) | 1990-06-27 |
| ES2058455T3 (es) | 1994-11-01 |
| ZA899760B (en) | 1990-09-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8100 | Publication of patent without earlier publication of application | ||
| D1 | Grant (no unexamined application published) patent law 81 | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |