KR930017934A - 폴리우레탄 제조용 악취 경감 촉매로서의 히드록시기-함유 아민-붕소 첨가 생성물 - Google Patents

폴리우레탄 제조용 악취 경감 촉매로서의 히드록시기-함유 아민-붕소 첨가 생성물 Download PDF

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KR930017934A
KR930017934A KR1019920017085A KR920017085A KR930017934A KR 930017934 A KR930017934 A KR 930017934A KR 1019920017085 A KR1019920017085 A KR 1019920017085A KR 920017085 A KR920017085 A KR 920017085A KR 930017934 A KR930017934 A KR 930017934A
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tertiary amine
catalyst composition
boron
catalyst
tertiary
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KR960011004B1 (ko
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코트스 레셔 사보카 앤
루이 마이클
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윌리암 에프. 마쉬
에어 프로덕츠 앤드 케미칼스, 인코오포레이티드
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/16Catalysts
    • C08G18/18Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20Heterocyclic amines; Salts thereof
    • C08G18/2045Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
    • C08G18/2063Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/16Catalysts
    • C08G18/18Catalysts containing secondary or tertiary amines or salts thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/16Catalysts
    • C08G18/18Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1875Catalysts containing secondary or tertiary amines or salts thereof containing ammonium salts or mixtures of secondary of tertiary amines and acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/16Catalysts
    • C08G18/22Catalysts containing metal compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00Foam properties
    • C08G2110/0008Foam properties flexible
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00Foam properties
    • C08G2110/0083Foam properties prepared using water as the sole blowing agent

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  • 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)
  • Catalysts (AREA)

Abstract

본 발명은 우레탄 반응, 구체적으로 폴리우레탄 포옴 제조시의 반응을 촉매화 하는, 3차 아민과 하기 일반식 (I)의 붕소 화합물의 첨가 생성물을 주성분으로 하는 아민-붕소 조성물에 관한 것이다:
RnB(OH)3-n(I)
상기 식에서 n은 0또는 1이고, R은 C1-C8알킬, C5-C8사이클로알킬 또는 C6-C10알킬, C5-C8사이클로알킬 또는 C6-C10아릴이다.
본 발명의 바람직한 촉매 조성물은 트리에틸렌디아민 또는 3-퀴누클리딘올과 붕산을 혼합하여 제조한다.

Description

폴리우레탄 제조용 악취 경감 촉매로서의 히드록시기-함유 아민-붕소 첨가 생성물
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (36)

  1. 3차 아민 우레탄 촉매와 하기 일반식 (I)의 붕소 화합물의 첨가 생성물을 주성분으로 하는 촉매 조성물:
    RnB(OH)3-n(I)
    상기 식에서, n은 0또는 1이고, R은 C1-C8알킬, C5-C8사이클로알킬 또는 C6-C10아릴이다.
  2. 제1항에 있어서, 상기 3차 아민이 펜타메틸디에틸렌트리아민, 펜타메틸디프로필렌트리아민, 비스(디메틸아미노에틸)에테르, 디메틸사이클로헥실아민, 4-디메틸아미노 피리딘, 디아자바이사이클로〔5.4.0〕운데크-7엔, 디아자바이사이클로-〔4.3.0〕논-5-엔, N-에틸모르폴린, N메틸모르폴린, N-세틸-N,N-디메틸아민, N-코코모르폴린, N-(N,N-디메틸아미노에틸)모르폴린, 트리스(3-디메틸아미노프로필)아민, 트리에틸렌디아민, N,N,N′-트리메틸-N′-히드록시에틸에틸렌디아민, N,N-디메틸에탄올아민, N,N,N′-트리메틸-N′-히드록시에틸-비스(아미노에틸)에테르 또는 3-퀴누클리딘올인 촉매 조성물.
  3. 제1항에 있어서, 상기 3차 아민이 히드록시기를 함유한 3차아민 우레탄 촉매인 촉매 조성물.
  4. 제1항에 있어서, 상기 3차 아민이 3-퀴누클리딘올인 촉매 조성물.
  5. 제1항에 있어서, 상기 3차 아민이 트리에틸렌디아민인 촉매 조성물.
  6. 제5항에 있어서, 3차 질소: 붕소의 몰 비율이 1:0.5 내지 1:1인 촉매 조성물.
  7. 제1항에 있어서, 상기 붕소 화합물이 붕산, 페닐붕산 또는 이소프로필붕산인 촉매 조성물.
  8. 제1항에 있어서, 상기 붕소 화합물이 붕산인 촉매 조성물.
  9. 제2항에 있어서, 상기 붕소 화합물이 붕산인 촉매 조성물.
  10. 제1항에 있어서, 3차 질소 : 붕소의 몰 비율이 1:0.1 내지 1:10인 촉매 조성물.
  11. 제1항에 있어서, 3차 질소 : 붕소의 몰 비율이 1:0.5 내지 1:2인 촉매 조성물.
  12. 제11항에 있어서, 상기 3차 아민이 트리에틸렌디아민 또는 3-퀴누클리딘올이고 상기 붕소 화합물이 붕산인 촉매 조성물.
  13. 이소시아네이트의 삼합화 및/또는 이소시아네이트와 활성 수소-함유 화합물간의 반응을 촉매화 하는 방법에 있어서, 3차 아민 우레탄 촉매와 하기 일반식(I)의 붕소 화합물의 첨가 생성물을 주성분으로 하는 촉매 조성물을 사용하는 것을 포함하는 것을 특징으로 하는 방법:
    RnB(OH)3-n(I)
    상기 식에서, n은 0또는 1이고, R은 C1-C8알킬, C5-C8사이클로알킬 또는 C6-C10아릴이다.
  14. 제13항에 있어서, 상기 촉매 조성물을 3차 아민 우레탄 촉매 또는 유기 주석 우레탄 촉매, 또는 상기 두가지 촉매 모두와 함께 혼합하여 사용하는 방법.
  15. 제13항에 있어서, 상기 3차 아민이 펜타메틸디에틸렌트리아민, 펜타메틸디프로필렌트리아민, 비스(디메틸아미노에틸)에테르, 디메틸사이클로헥실아민, 트리에틸렌디아민, N,N,N′-트리메틸-N′-히드록시에틸에틸렌디아민, N,N-디메틸에탄올아민, N,N,N′-트리메틸-N′-히드록시에틸비스(아미노에틸)에테르 또는 3-퀴누클리딘올인 방법.
  16. 제13항에 있어서, 상기 3차 아민이 히드록시기를 함유한 3차아민 우레탄 촉매인 방법.
  17. 제13항에 있어서, 상기 3차 아민이 3-퀴누클리딘올인 방법.
  18. 제13항에 있어서, 상기 3차 아민이 트리에틸렌디아민인 방법.
  19. 제18항에 있어서, 3차 질소:붕소의 몰 비율이 1:0.5 내지 1:1인 방법.
  20. 제13항에 있어서, 상기 붕소 화합물이 붕산, 페닐붕산, 이소프로필붕산인 방법.
  21. 제13항에 있어서, 상기 붕소 화합물이 붕산인 방법.
  22. 제15항에 있어서, 상기 붕소 화합물이 붕산인 방법.
  23. 제13항에 있어서, 3차 질소: 붕소의 몰 비율이 1:0.1 내지 1:10인 방법.
  24. 제13항에 있어서, 3차 질소: 붕소의 몰 비율이 1:0.5 내지 1:2인 방법.
  25. 제24항에 있어서, 상기 3차 아민이 트리에틸렌디아민 또는 3-퀴누클리딘올이고 상기 붕소 화합물이 붕산인 방법.
  26. 유기 폴리이소시아네이트와 폴리올을 팽창제, 셀 안정화제 및 촉매 조성물의 존재하에 반응시키는 단계를 포함하는 폴리우레탄 포옴의 제조 방법에 있어서, 3차 아민 우레탄 촉매와 붕산의 첨가 생성물을 주성분으로 하는 촉매 조성물을 사용하는 것을 포함하는 것을 특징으로 하는 방법.
  27. 제26항에 있어서, 상기 촉매 조성물을 3차 아민 우레탄 촉매 또는 유기 주석 우레탄 촉매, 또는 상기 두가지 촉매 모두와 함께 혼합하여 사용하는 방법.
  28. 제26항에 있어서, 상기 3차 아민이 펜타메틸디에틸렌트리아민, 펜타메틸디프로필렌트리아민, 비스(디메틸아미노에틸)에테르, 디메틸사이클로헥실아민, 트리에틸렌디아민, N,N,N′-트리메틸-N′-히드록시에틸에틸렌디아민, N,N-디메틸에탄올아민, N,N,N′-트리메틸-N′-히드록시에틸비스(아미노에틸)에테르 또는 3-퀴누클리딘올인 방법.
  29. 제26항에 있어서, 상기 3차 아민이 히드록시기를 함유한 3차아민 우레탄 촉매인 방법.
  30. 제26항에 있어서, 상기 3차 아민이 3-퀴누클리딘올인 방법.
  31. 제26항에 있어서, 상기 3차 아민이 트리에틸렌디아민인 방법.
  32. 제31항에 있어서, 3차 질소: 붕소의 몰 비율이 1:0.5 내지 1:1인 방법.
  33. 제26항에 있어서, 3차 질소: 붕소의 몰 비율이 1:0.1 내지 1:10인 방법.
  34. 제26항에 있어서, 3차 질소: 붕소의 몰 비율이 1:0.5 내지 1:2인 방법.
  35. 제34항에 있어서, 상기 3차 아민이 트리에틸렌디아민 또는 3-퀴누클리딘올이고 상기 붕소 화합물이 붕산인 방법.
  36. 제35항에 있어서, 상기 촉매 조성물을 3차 아민 우레탄 촉매 또는 유기 주석 우레탄 촉매, 또는 상기 두가지 촉매 모두와 함께 혼합하여 사용하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019920017085A 1991-09-20 1992-09-19 폴리우레탄 제조용 악취 경감 촉매로서의 히드록시기-함유 아민-붕소 첨가 생성물 KR960011004B1 (ko)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US07/763,107 US5086081A (en) 1991-09-20 1991-09-20 Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes
US91-763107 1991-09-20
US07/829,786 US5162379A (en) 1991-09-20 1992-01-31 Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes
US92-829786 1992-01-31
US92-839519 1992-02-20
US07/839,519 1992-02-20
US07/839,519 US5166223A (en) 1991-09-20 1992-02-20 Hydroxyl group-containing amine-boron adducts are reduced odor catalyst compositions for the production of polyurethanes

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KR930017934A true KR930017934A (ko) 1993-09-20
KR960011004B1 KR960011004B1 (ko) 1996-08-16

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US (2) US5166223A (ko)
EP (1) EP0533071B1 (ko)
JP (1) JP2682607B2 (ko)
KR (1) KR960011004B1 (ko)
AR (1) AR248149A1 (ko)
AU (1) AU640575B2 (ko)
BR (1) BR9203572A (ko)
CA (2) CA2078382A1 (ko)
DE (1) DE69216184T2 (ko)
DK (1) DK0533071T3 (ko)
ES (1) ES2095375T3 (ko)
NO (1) NO923620L (ko)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5166223A (en) * 1991-09-20 1992-11-24 Air Products And Chemicals, Inc. Hydroxyl group-containing amine-boron adducts are reduced odor catalyst compositions for the production of polyurethanes
AUPM621194A0 (en) * 1994-06-10 1994-07-07 Commonwealth Scientific And Industrial Research Organisation Conversion coating and process for its formation
US5539007A (en) * 1994-08-31 1996-07-23 Air Products And Chemicals, Inc. Catalyst compositions for making polyurethane based on imidazoles and boron compounds
EP0741154B1 (en) * 1994-10-21 2004-01-07 Sanyo Chemical Industries, Ltd. Curable composition
US5710191A (en) * 1995-06-05 1998-01-20 Air Products And Chemicals, Inc. Hydroxymethyl quinuclidine catalyst compositions for making polyurethane foams
AUPQ633200A0 (en) 2000-03-20 2000-04-15 Commonwealth Scientific And Industrial Research Organisation Process and solution for providing a conversion coating on a metallic surface I
AUPQ633300A0 (en) 2000-03-20 2000-04-15 Commonwealth Scientific And Industrial Research Organisation Process and solution for providing a conversion coating on a metallic surface ii
EP1291371A1 (en) 2001-03-16 2003-03-12 Hodogaya Chemical Co., Ltd. Process for producing urethane-modified polyisocyanurate foam
US6534555B1 (en) 2001-09-10 2003-03-18 Huntsman Petrochemical Corporation Catalyst systems for polyurethane polyester foams
CN1639240A (zh) * 2002-07-18 2005-07-13 胡茨曼石油化学公司 提高泡沫体中三聚物含量的催化剂组合物
US20050059749A1 (en) * 2003-09-16 2005-03-17 Huntsman Petrochemical Corporation Catalysts useful in polyurethane foam
PL1773902T3 (pl) * 2004-08-04 2018-05-30 Foam Supplies, Inc. Odchylenie reaktywności i rozkład katalizatora w piance poliuretanowej
JP4901225B2 (ja) * 2006-01-25 2012-03-21 花王株式会社 ポリウレタンフォーム製造用ポリオール混合物
JP2013234272A (ja) * 2012-05-09 2013-11-21 Tosoh Corp ポリウレタン樹脂製造用触媒組成物及びそれを用いたポリウレタン樹脂の製造方法
EP2878609B1 (en) * 2012-07-26 2019-06-05 Tosoh Corporation Amine catalyst for curing polyisocyanate compound and polyisocyanate adhesive composition containing amine catalyst for curing polyisocyanate compound
WO2021029836A1 (en) * 2019-08-09 2021-02-18 Safaş Saf Plasti̇k Sanayi̇ Ve Ti̇caret Anoni̇m Şi̇rketi̇ Boron-modified flexible polyurethane foam for hygiene and a method of production therefor

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3127404A (en) * 1960-04-04 1964-03-31 Iriethylenediamine addition product
GB1083394A (en) * 1964-09-16 1967-09-13 Upjohn Co Polyurethane foams
GB1182014A (en) * 1966-10-29 1970-02-25 San Abbott Ltd Urethane and Urea Catalyst
DE2434185A1 (de) * 1974-07-16 1976-02-05 Bayer Ag Verfahren zur herstellung von amidin-metall-komplexen
FR2301554A1 (fr) * 1975-02-18 1976-09-17 Peugeot & Renault Procede de moulage de matieres synthetiques
US4026840A (en) * 1975-06-09 1977-05-31 Air Products And Chemicals, Inc. Hydroxyalkyl tertiary amine catalysts for isocyanate reactions
JPS59500521A (ja) * 1982-03-26 1984-03-29 アクゾナ・インコ−ポレ−テッド ポリウレタン触媒のほう酸4級アンモニウム
US4425444A (en) * 1983-03-17 1984-01-10 Akzona Incorporated Polyols for urethane-modified isocyanurate foams
US4530938A (en) * 1984-03-21 1985-07-23 Akzona Incorporated Polyols for urethane-modified isocyanurate foams
US4611013A (en) * 1984-06-12 1986-09-09 Bp Chemicals Limited Catalysts for the preparation of carbodiimide foams and elastomers
DE3610434A1 (de) * 1986-03-08 1987-09-10 Bayer Ag Neue umsetzungsprodukte und ihre verwendung als katalysatoren bei der herstellung von kunststoffen auf isocyanatbasis
US5177046A (en) * 1991-09-20 1993-01-05 Air Products And Chemicals, Inc. Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes
US5166223A (en) * 1991-09-20 1992-11-24 Air Products And Chemicals, Inc. Hydroxyl group-containing amine-boron adducts are reduced odor catalyst compositions for the production of polyurethanes
US5086081A (en) * 1991-09-20 1992-02-04 Air Products And Chemicals, Inc. Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes
US5162379A (en) * 1991-09-20 1992-11-10 Air Products And Chemicals, Inc. Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes
US5130403A (en) * 1991-09-20 1992-07-14 Air Products And Chemicals, Inc. Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes

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AU2358292A (en) 1993-04-08
CA2078382A1 (en) 1993-03-21
AU640575B2 (en) 1993-08-26
ES2095375T3 (es) 1997-02-16
NO923620D0 (no) 1992-09-17
JP2682607B2 (ja) 1997-11-26
DE69216184T2 (de) 1997-04-17
EP0533071B1 (en) 1996-12-27
JPH05202159A (ja) 1993-08-10
NO923620L (no) 1993-03-22
BR9203572A (pt) 1993-04-13
AR248149A1 (es) 1995-06-30
DK0533071T3 (ko) 1997-02-17
EP0533071A1 (en) 1993-03-24
DE69216184D1 (de) 1997-02-06
KR960011004B1 (ko) 1996-08-16
US5356942A (en) 1994-10-18
CA2078383A1 (en) 1993-03-21
US5166223A (en) 1992-11-24

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