KR970069982A - Reactive amine catalysts and their use in polyurethane polymers - Google Patents

Reactive amine catalysts and their use in polyurethane polymers Download PDF

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KR970069982A
KR970069982A KR1019970012972A KR19970012972A KR970069982A KR 970069982 A KR970069982 A KR 970069982A KR 1019970012972 A KR1019970012972 A KR 1019970012972A KR 19970012972 A KR19970012972 A KR 19970012972A KR 970069982 A KR970069982 A KR 970069982A
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amine
alkyl
amide
formula
methyl
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KR1019970012972A
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KR100302090B1 (en
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엠. 거킨 리챠드
케이. 로빈슨 케이
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엠. 거킨 리챠드
케이. 로빈슨 케이
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    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Catalysts (AREA)

Abstract

본 발명은 폴리우레탄 형성 반응의 촉매로서 사용하기 위한 아민/아미드 촉매를 제공한다. 이소시아네이트와의 반응성으로 인하여 휘발성이 작고 양호한 촉매활성을 갖는 아민/아미드 촉매는 하기 화학식(2)의 구조를 갖는다.The present invention provides an amine / amide catalyst for use as a catalyst in a polyurethane forming reaction. The amine / amide catalyst having low volatility due to the reactivity with isocyanate and having good catalytic activity has the structure of the following formula (2).

상기 식에서 Q는 CzH2z+1또는 (CH2)nN(R3)kT이고, T는 양 말단이 질소에 부착되어 시클릭기를 형성하는 2가 시클릭기이거나 또는 1가 알킬, 아미노알킬 또는 알킬아미노알킬기이고, k는 0 또는 1이되, T가 1가기이면 k는 1이고, T가 2가기이면, k는 0이고 R2는 H 또는 CzH2z+1이고, R4는 H이고, R5는 H 또는 CH3이고, n은 2 내지 6이고, z는 1 내지 4이다. n은 바람직하게는 2 또느 3이고, z는 바람직하게는 1이다. 각각의 R3및 T는 각각의 n 및 z의 수치에 따라 동일하거나 상이하다. 상기 화학식의 하나의 특히 바람직한 범위는 Q가 CzH2z+1인 것이다. Wherein Q is C z H 2z + 1 or (CH 2 ) n N (R 3 ) k T, T is a divalent cyclic group having both terminals attached to nitrogen to form a cyclic group, is amino alkyl or amino alkyl group, k is 0 or 1 provided that, when T is monovalent and k is 1, if T is a divalent group, and k is 0 and R 2 is H or C z H 2z + 1, R 4 is H, R 5 is H or CH 3, n is 2 to 6, z is 1 to 4. n is preferably 2 or 3, and z is preferably 1. Each of R < 3 > and T is the same or different depending on the value of each n and z. One especially preferred range of the above formulas is that Q is C z H 2z + 1 .

Description

반응성 아민 촉매 및 폴리우레탄 중합체에서의 그 용도Reactive amine catalysts and their use in polyurethane polymers

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is a trivial issue, I did not include the contents of the text.

Claims (19)

하기 화학식(2a)의 아민/아미드.Amine / amide of formula (2a) 상기 식에서, T는 1가 C1-C4-알킬, 아미노-C1-C4-알킬, 모노-C1-C4-알킬아미노-C1-C4-알킬 또는 디-C1-C4-알킬아미노-C1-C4-알킬기이거나, 또는 T가 부착되는 화학식(2a)에 나타낸 질소 원자와 함께 고리 내의 6개 이하의 탄소 원자 및 화학식(2a)에 나타낸 질소 원자를 포함하고 C1내지 C4알킬로 치환될 수 있는 시클릭 구조를 형성하는 2가 알킬, 아민 치환 알킬, 알킬아미노알킬 또는 알콕시알킬기이고, k는 0 또는 1이되, T가 1가기이면 k는 1이고, T가 2가 기이면 k는 0이고, R2는 H 또는 CzH2z+1이고, R3은 CzH2z-1이고, R4는 H이고, R5는 H 또는 CH3이고, n은 2 내지 6이고, z는 1 내지 4이다.Wherein, T 1 is a C 1 -C 4 - alkyl, amino -C 1 -C 4 - alkyl, mono -C 1 -C 4 - alkylamino, -C 1 -C 4 - alkyl or di -C 1 -C 4 -alkylamino-C 1 -C 4 -alkyl group, or together with the nitrogen atom shown in formula (2a) to which T is attached, together with up to 6 carbon atoms in the ring and the nitrogen atom shown in formula (2a) An amino-substituted alkyl, an alkylaminoalkyl or an alkoxyalkyl group which forms a cyclic structure which may be substituted with 1 to 4 alkyl, k is 0 or 1, k is 1 when T is 1, and T R 2 is H or C z H 2z + 1 , R 3 is C z H 2z-1 , R 4 is H, R 5 is H or CH 3 and n Is 2 to 6, and z is 1 to 4. 제1항에 있어서, 하기 화학식(2b)의 아민/아미드.2. The amine / amide of claim 1, wherein R < 1 > 제2항에 있어서, R1이 메틸인 아민/아미드.The amine / amide of claim 2 wherein R < 1 > is methyl. 제3항에 있어서, R3이 메틸인 아민/아미드.4. The amine / amide of claim 3 wherein R < 3 > is methyl. 제2항에 있어서, R3이 메틸인 아민/아미드. 3. The amine / amide of claim 2 wherein R < 3 > is methyl. 제3항에 있어서, 하기 화학식(3)의 아민/아미드.4. The amine / amide of claim 3, wherein R < 1 > 제3항에 있어서, n이 2 또는 3이고 z가 인 아민/아미드.4. The amine / amide of claim 3, wherein n is 2 or 3 and z is zero. 폴리올 성분 및 폴리이소시아네이트 성분으로 이루어지는 반응 혼합물을 형성하여 유효량의 반응 촉매의 존재 하에 반응시키는 폴리우레탄의 제조 방법에 있어서, 상기 반응 혼합물이 또한 하기 화학식(2)의 아민/아미드를 포함하는 개선된 방법.A process for preparing a polyurethane which comprises forming a reaction mixture comprising a polyol component and a polyisocyanate component in the presence of an effective amount of a reaction catalyst, characterized in that the reaction mixture further comprises an amine / amide of the formula (2) . 상기 식에서, Q는 CzH2z+1또는 (CH2)nN(R3)kT이고, T는 1가 C1-C4-알킬, 아미노-C1-C4-알킬, 모노-C1-C4-알킬아미노-C1-C4-알킬 또는 디-C1-C4-알킬아미노-C1-C4-알킬기이거나, 또는 T가 부착되는 화학식(2)에 나타낸 질소 원자와 함께 고리 내에 6 이하의 탄소 원자 및 화학식(2)에 나타낸 질소 원자를 포함하고, C1내지 C4알킬로 치환될 수 있는 시클릭 구조를 형성하는 2가 알킬, 아민 치환 알킬, 알킬아미노알킬 또는 알콕시알킬기이고, k는 0 또는 1이되, T가 1가기아면 k는 1이고, T가 2가기이면 k는 0이고, R2는 H 또는 CzH2z+1이고, R4는 H이고, R5는 H 또는 CH3이고, n은 2 내지 6이고, z는 1 내지 4이다. Wherein Q is C z H 2z + 1 or (CH 2 ) n N (R 3 ) k T, T is monovalent C 1 -C 4 -alkyl, amino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylamino-C 1 -C 4 -alkyl or a di-C 1 -C 4 -alkylamino-C 1 -C 4 -alkyl group, or the nitrogen atom shown in formula (2) including the nitrogen atom shown in a carbon atom and the formula (2) of 6 or lower in the ring with, and, C 1 to C 4 2 is an alkyl to form a cyclic structure which may be substituted with alkyl, amine substituted alkyl, alkylaminoalkyl And k is 0 or 1 if T is 1 and k is 1 if T is 2 and k is 0 and R 2 is H or C z H 2z + 1 and R 4 is H , R 5 is H or CH 3 , n is 2 to 6, and z is 1 to 4. 제8항에 있어서, Q가 R1이고 R1이 CzH2z+1인 방법.9. The method of claim 8, wherein Q is R 1 and R 1 is C z H 2z + 1. 제8항에 있어서, n이 2 내지 3이고 z가 1인 방법.9. The method of claim 8, wherein n is 2 to 3 and z is 1. 제10항에 있어서, R1이 메틸인 방법.11. The method of claim 10, wherein R < 1 > is methyl. 제8항에 있어서, R3이 메틸인 방법.9. The method of claim 8 wherein R < 3 > is methyl. 제8항에 있어서, R4가 수소인 방법.9. The method of claim 8 wherein R < 4 > is hydrogen. 제8항에 있어서, 아민/아미드가 하기 화학식(4)의 구조인 방법.9. The method of claim 8, wherein the amine / amide is of structure (4). 제8항에 있어서, 제조되는 폴리우레탄이 엘라스토머인 방법.The process according to claim 8, wherein the polyurethane to be produced is an elastomer. 제8항에 있어서, 제조되는 폴리우레탄이 폴리우레탄 발포체인 방법.The process according to claim 8, wherein the polyurethane to be produced is a polyurethane foam. 제16항에 있어서, 발포체가 성형 가요성 발포체인 방법.17. The method of claim 16, wherein the foam is a molded flexible foam. 제16항에 있어서, 발포체가 강성 발포체인 방법.17. The method of claim 16, wherein the foam is a rigid foam. 제18항에 있어서, 아민/아미드가 폴리올 100부 당 0.02 내지 5부의 양으로 존재하는 것인 방법.19. The process of claim 18, wherein the amine / amide is present in an amount of 0.02 to 5 parts per 100 parts of polyol. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed by the contents of the first application.
KR1019970012972A 1996-04-04 1997-04-04 Reactive amine catalysts and their use in polyurethane polymers KR100302090B1 (en)

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US1484396P 1996-04-04 1996-04-04
US60/014,843 1996-04-04

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CN110951081B (en) * 2019-11-08 2022-03-18 东华大学 Non-volatile multifunctional POSS-based tertiary amine catalyst and preparation and application thereof

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US4049591A (en) * 1976-10-18 1977-09-20 Texaco Development Corporation Foams and elastomers prepared in the presence of high tertiary amine content polyurethane catalysts
US4259259A (en) * 1979-11-15 1981-03-31 Texaco Development Corp. Preparation of β-aminopropionamides
US4287363A (en) * 1980-09-02 1981-09-01 Texaco Inc. Preparation of N-(alkylaminoalkyl)acrylamides
US4910230A (en) * 1987-12-25 1990-03-20 Tosoh Corporation Preparation of fine-cell rigid polyurethane foam using amine catalyst

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MX9702462A (en) 1998-04-30
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AR006541A1 (en) 1999-09-08

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