KR960701142A - Methods for stabilizing organic materials susceptible to thermal degradation and / or oxidative degradation and the resulting stabilizing materials - Google Patents

Methods for stabilizing organic materials susceptible to thermal degradation and / or oxidative degradation and the resulting stabilizing materials Download PDF

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KR960701142A
KR960701142A KR1019950704161A KR19950704161A KR960701142A KR 960701142 A KR960701142 A KR 960701142A KR 1019950704161 A KR1019950704161 A KR 1019950704161A KR 19950704161 A KR19950704161 A KR 19950704161A KR 960701142 A KR960701142 A KR 960701142A
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hydroxyphenyl
dialkyl
alkanoic acid
polyhydroxyl alcohol
alkyl ester
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로우렌스 비. 배리
로버트 지. 로우랜드
마크 씨. 리차드슨
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배리 제이. 사인맨
유니로얄 케미칼 컴페니, 인크.
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    • 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
    • C08K5/134—Phenols containing ester groups
    • C08K5/1345—Carboxylic esters of phenolcarboxylic acids
    • 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

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  • 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)

Abstract

열열화 및/또는 산화열되기 쉬운 유기물질, 예를 들면 폴리에테르 폴리올 및 폴리에테르 폴리올로 제조된 폴리우레탄 포옴이, 안정화에 필요한 양의, 액상, 결정화 저항성의, 주로 페놀계 모노에스테르로 되어 있는 페놀계 에스테르 혼합물(여기서 페놀계 에스테르 혼합물은, 에스테르화 반응촉매를 채용하는 에스테르화 반응 조건하에서, 3,5-디알킬-4-히드록시페닐 알카노산의 알킬에스테르와 폴리히드록실 알콜의 반응에 의하여 제조된다)을 첨가시킴으로써, 열화에 대하여 안정화된다.Polyurethane foams made of organic materials susceptible to thermal degradation and / or oxidation, such as polyether polyols and polyether polyols, are liquid, crystallization resistant, mainly phenolic monoesters in the amounts required for stabilization. Phenolic ester mixtures (where the phenolic ester mixtures are used for the reaction of alkyl esters of 3,5-dialkyl-4-hydroxyphenyl alkanoic acid with polyhydroxyl alcohol under esterification conditions employing an esterification catalyst). Stabilized against degradation.

Description

열열화 및/또는 산화열화되기 쉬운 유기물질의 안정화 방법 및 그 결과 얻어진 안정화 물질Methods for stabilizing organic materials susceptible to thermal degradation and / or oxidative degradation and the resulting stabilizing materials

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (20)

열열화 및/또는 산화열화되기 쉬운 유기물질에, 안정화에 필요한 양의, 액상, 결정화 저항성의, 주로 페놀계 모노에스테르로 되어 있는 페놀계 에스테르 혼합물(여기서 페놀계 에스테르 혼합물은, 에스테르화 반응 촉매를 채용하는 에스테르화 반응 조건하에서, 3,5-디알킬-4-히드록시페닐 알카노산의 알킬에스테르와 폴리히드록실 알콜의 반응에 의하여 제조된다)을 첨합시키는 것을 포함하는, 상기 유기물질의 안정화 방법.A phenolic ester mixture composed mainly of phenolic monoesters in a liquid phase, crystallization resistance, in an amount necessary for stabilization, in an organic material that is susceptible to thermal degradation and / or oxidative degradation (wherein the phenolic ester mixture is an esterification catalyst A method of stabilizing the organic material, comprising the step of adding the alkyl ester of 3,5-dialkyl-4-hydroxyphenyl alkanoic acid and a polyhydroxyl alcohol) under the esterification conditions employed. . 제1항에 있어서, 열화되기 쉬운 유기물질이 폴리에테르 폴리올 및 폴리우레탄으로 구성되어 있는 군으로부터 선택되는 안정화 방법.The stabilizing method according to claim 1, wherein the organic material that is susceptible to degradation is selected from the group consisting of polyether polyols and polyurethanes. 제1항에 있어서, 3,5-디알킬-4-히드록시페닐 알카노산의 알킬에스테르가 하기 일반식으로 갖는 안정화 방법.The stabilizing method according to claim 1, wherein the alkyl ester of 3,5-dialkyl-4-hydroxyphenyl alkanoic acid has the following general formula. 여기서, R1, R2및 R3각각은 동일하거나 상이하며 탄소원자 1~6의 알킬그룹을 나타내고, n은 0,1 또는 2이고, 폴리히드록실 알코올은 일반식 R(OH)n을 갖는데, 여기서 R은 탄소원자 2~12의 지방족 그룹이며, n은 2~7이다.Wherein R 1 , R 2 and R 3 are the same or different and represent alkyl groups of 1 to 6 carbon atoms, n is 0,1 or 2, and the polyhydroxyl alcohol has the general formula R (OH) n Where R is an aliphatic group of 2-12 carbon atoms and n is 2-7. 제3항에 있어서, 폴리히드록실 알코올이 제2히드록실 그룹을 지니는 디올 또는 트리올인 안정화 방법.4. The method of claim 3 wherein the polyhydroxyl alcohol is a diol or a triol having a second hydroxyl group. 제3항에 있어서, 에스테르화 촉매가 산성 에스테르화 촉매인 안정화 방법.The method of claim 3, wherein the esterification catalyst is an acidic esterification catalyst. 제3항에 있어서, 3,5-디알킬-4-히드록시페닐 알카노산의 알킬 에스테르에 대한 폴리히드록실 알코올의 몰비가 1.2:1~10:1인 안정화 방법.The stabilizing method according to claim 3, wherein the molar ratio of polyhydroxyl alcohol to alkyl ester of 3,5-dialkyl-4-hydroxyphenyl alkanoic acid is 1.2: 1 to 10: 1. 제3항에 있어서, 3,5-디알킬-4-히드록시페닐 알카노산의 알킬 에스테르에 대한 폴리히드록실 알코올의 몰비가 1.5:1~6:1인 안정화 방법.The stabilizing method according to claim 3, wherein the molar ratio of polyhydroxyl alcohol to alkyl ester of 3,5-dialkyl-4-hydroxyphenyl alkanoic acid is 1.5: 1 to 6: 1. 제3항에 있어서, 폴리히드록실 알코올이 제2히드록실 그룹을 지니는 디올 또는 트리올이고, 에스테르화 촉매가 산성 에스테르화 촉매이며, 3,5-디알킬-4-히드록시페닐 알카노산의 알킬 에스테르에 대한 폴리히드록실 알코올의 몰비가 1.2:1~10:1인 안정화 방법.The polyhydroxy alcohol of claim 3, wherein the polyhydroxyl alcohol is a diol or triol having a second hydroxyl group, the esterification catalyst is an acidic esterification catalyst, alkyl of 3,5-dialkyl-4-hydroxyphenyl alkanoic acid. The molar ratio of polyhydroxyl alcohol to ester is 1.2: 1 to 10: 1. 제8항에 있어서, 지방족 폴리히드록실 알코올이 1,2-프로판디올, 1,3-부탄디올 또는 글리세롤이고, 3,5-디알킬-4-히드록시페닐 알카노산의 알킬에스테르가 메틸 3-(3,5-디-t-부틸-4-히드록시페닐)프로피온에이트, 에닐 3-(3,5-디-t-부틸-4-히드록시페닐)프로피온에이트, 또는 프로필 3-(3,5-디-t-부틸-4-히드록시페닐)프로피온에이트인 안정화 방법.The method of claim 8, wherein the aliphatic polyhydroxyl alcohol is 1,2-propanediol, 1,3-butanediol or glycerol, and the alkyl ester of 3,5-dialkyl-4-hydroxyphenyl alkanoic acid is methyl 3- ( 3,5-di-t-butyl-4-hydroxyphenyl) propionate, enyl 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate, or propyl 3- (3,5 Stabilization method which is -di-t-butyl-4-hydroxyphenyl) propionate. 제8항에 있어서, 열화되기 쉬운 유기물질이 폴리에테르 폴리올 및 폴리우레탄으로 구성되어 있는 군으로부터 선택되는 안정화 방법.The stabilization method according to claim 8, wherein the organic material susceptible to degradation is selected from the group consisting of polyether polyols and polyurethanes. 열열화 및/또는 산화열화되기 쉬운 유기물질 및 안정화에 필요한 양의, 액상, 결정화 저항성의, 주로 페놀계 모노에스테르로 되어 있는 페놀계 에스테르 혼합물(여기서 페놀계 에스테르 혼합물은, 에스테르화 반응 촉매를 채용하는 에스테르화 반응 조건하에서, 3,5-디알킬-4-히드록시페닐 알카노산의 알킬에스테르와 폴리히드록실 알콜의 반응에 의하여 제조된다)을 포함하는 조성물.Phenol ester mixtures composed mainly of phenolic monoesters, liquid phase, crystallization resistant, in amounts of organic materials susceptible to thermal degradation and / or oxidation, and wherein the phenolic ester mixture employs an esterification reaction catalyst. Under the esterification reaction condition, which is prepared by the reaction of an alkylester of 3,5-dialkyl-4-hydroxyphenyl alkanoic acid with a polyhydroxyl alcohol). 제11항에 있어서, 열화되기 쉬운 유기물질이 폴리에테르 폴리올 및 폴리우레탄으로 구성되어 있는 군으로부터 선택되는 조성물.The composition of claim 11 wherein the organic material susceptible to degradation is selected from the group consisting of polyether polyols and polyurethanes. 제11항에 있어서, 3,5-디알킬-4-히드록시페닐 알카노산의 알킬에스테르가 하기 일반식으로 갖는 조성물.The composition according to claim 11, wherein the alkyl ester of 3,5-dialkyl-4-hydroxyphenyl alkanoic acid has the following general formula. 여기서, R1, R2및 R3각각은 동일하거나 상이하며 탄소원자 1~6의 알킬그룹을 나타내고, n은 0,1 또는 2이고, 폴리히드록실 알코올은 일반식 R(OH)n을 갖는데, 여기서 R은 탄소원자 2~12의 지방족 그룹이며, n은 2~7이다.Wherein R 1 , R 2 and R 3 are the same or different and represent alkyl groups of 1 to 6 carbon atoms, n is 0,1 or 2, and the polyhydroxyl alcohol has the general formula R (OH) n Where R is an aliphatic group of 2-12 carbon atoms and n is 2-7. 제13항에 있어서, 폴리히드록실 알코올이 제2히드록실 그룹을 지니는 디올 또는 트리올인 조성물.The composition of claim 13, wherein the polyhydroxyl alcohol is a diol or a triol having a second hydroxyl group. 제13항에 있어서, 에스테르화 촉매가 산성 에스테르화 촉매인 조성물.The composition of claim 13, wherein the esterification catalyst is an acidic esterification catalyst. 제13항에 있어서, 3,5-디알킬-4-히드록시페닐 알카노산의 알킬 에스테르에 대한 폴리히드록실 알코올의 몰비가 1.2:1~10:1인 조성물.The composition of claim 13 wherein the molar ratio of polyhydroxyl alcohol to alkyl ester of 3,5-dialkyl-4-hydroxyphenyl alkanoic acid is from 1.2: 1 to 10: 1. 제13항에 있어서, 3,5-디알킬-4-히드록시페닐 알카노산의 알킬 에스테르에 대한 폴리히드록실 알코올의 몰비가 1.5:1~6:1인 조성물.The composition of claim 13 wherein the molar ratio of polyhydroxyl alcohol to alkyl ester of 3,5-dialkyl-4-hydroxyphenyl alkanoic acid is from 1.5: 1 to 6: 1. 제13항에 있어서, 지방족 폴리히드록실 알코올이 제2히드록실 그룹을 지니는 디올 또는 트리올이고, 에스테르화 촉매가 산성 에스테르화 촉매이며, 3,5-디알킬-4-히드록시페닐 알카노산의 알킬 에스테르에 대한 폴리히드록실 알코올의 몰비가 1.2:1~10:1인 조성물.15. The process of claim 13 wherein the aliphatic polyhydroxyl alcohol is a diol or triol having a second hydroxyl group, the esterification catalyst is an acidic esterification catalyst, and a 3,5-dialkyl-4-hydroxyphenyl alkanoic acid Wherein the molar ratio of polyhydroxyl alcohol to alkyl ester is 1.2: 1 to 10: 1. 제18항에 있어서, 지방족 폴리히드록실 알코올이 1,2-프로판디올, 1,3-부탄디올 또는 글리세롤이고, 3,5-디알킬-4-히드록시페닐 알카노산의 알킬 에스테르가 메틸 3-(3,5-디-t-부틸-4-히드록시페닐)프로피온에이트, 에틸3-(3,5-디-t-부틸-4-히드록시페닐)프로피온에이트, 또는 프로필 3-(3,5-디-t-부틸-4-히드록시페닐)프로피온에이트인 조성물.19. The process of claim 18 wherein the aliphatic polyhydroxyl alcohol is 1,2-propanediol, 1,3-butanediol or glycerol and the alkyl ester of 3,5-dialkyl-4-hydroxyphenyl alkanoic acid is methyl 3- ( 3,5-di-t-butyl-4-hydroxyphenyl) propionate, ethyl 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate, or propyl 3- (3,5 -Di-t-butyl-4-hydroxyphenyl) propionate. 제18항에 있어서, 염화되기 쉬운 유기물질이 폴리에테르 폴리올 및 폴리우레탄으로 구성되어 있는 군으로부터 선택되는 조성물.The composition of claim 18 wherein the organic material susceptible to chloride is selected from the group consisting of polyether polyols and polyurethanes. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019950704161A 1993-03-30 1994-03-22 Methods for stabilizing organic materials susceptible to thermal degradation and / or oxidative degradation and the resulting stabilizing materials KR960701142A (en)

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ES2212350T3 (en) * 1997-09-30 2004-07-16 Uniroyal Chemical Company, Inc. POLYETER STABILIZED POLYOL AND POLYURETHANE FOAM OBTAINED FROM THE SAME.
DE10032582A1 (en) * 2000-07-05 2002-01-17 Basf Ag Stabilizers, especially for thermoplastic polyurethanes
DE10120838A1 (en) * 2001-04-27 2002-10-31 Basf Ag Mixture of substances for UV stabilization of plastics and their production
WO2003051816A1 (en) * 2001-12-14 2003-06-26 Uniroyal Chemical Company, Inc. Method of preparing hydroxyalkyl hindered phenolic antioxidants
DE10327009A1 (en) * 2003-06-12 2004-12-30 Basf Ag Mixtures containing isocyanate and stabilizer
US7329772B2 (en) * 2004-04-29 2008-02-12 Crompton Corporation Method for the preparation of a hydroxyalkyl hindered phenolic antioxidant

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