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

Info

Publication number
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
Authority
KR
South Korea
Prior art keywords
tertiary amine
catalyst composition
boron
catalyst
tertiary
Prior art date
Application number
KR1019920017085A
Other languages
English (en)
Other versions
KR960011004B1 (ko
Inventor
코트스 레셔 사보카 앤
루이 마이클
Original Assignee
윌리암 에프. 마쉬
에어 프로덕츠 앤드 케미칼스, 인코오포레이티드
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US07/763,107 external-priority patent/US5086081A/en
Priority claimed from US07/829,786 external-priority patent/US5162379A/en
Application filed by 윌리암 에프. 마쉬, 에어 프로덕츠 앤드 케미칼스, 인코오포레이티드 filed Critical 윌리암 에프. 마쉬
Publication of KR930017934A publication Critical patent/KR930017934A/ko
Application granted granted Critical
Publication of KR960011004B1 publication Critical patent/KR960011004B1/ko

Links

Classifications

    • 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

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)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (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
US92-829786 1992-01-31
US07/829,786 US5162379A (en) 1991-09-20 1992-01-31 Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes
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
US07/839,519 1992-02-20
US92-839519 1992-02-20

Publications (2)

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

Family

ID=27419562

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019920017085A KR960011004B1 (ko) 1991-09-20 1992-09-19 폴리우레탄 제조용 악취 경감 촉매로서의 히드록시기-함유 아민-붕소 첨가 생성물

Country Status (12)

Country Link
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) CA2078383A1 (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
CA2179644C (en) * 1994-10-21 2007-06-12 Shunji Matsunaga 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
WO2002077053A1 (fr) * 2001-03-16 2002-10-03 Hodogaya Chemical Co., Ltd. Procede de production d'une mousse de polyisocyanurate a urethane modifie
US6534555B1 (en) 2001-09-10 2003-03-18 Huntsman Petrochemical Corporation Catalyst systems for polyurethane polyester foams
CA2493404A1 (en) * 2002-07-18 2004-01-29 Huntsman Petrochemical Corporation Catalyst combinations for increasing trimer content in foam
US20050059749A1 (en) * 2003-09-16 2005-03-17 Huntsman Petrochemical Corporation Catalysts useful in polyurethane foam
MX2007001331A (es) * 2004-08-04 2008-03-11 Foam Supplies Inc Variacion de la reactividad y degradacion del catalizador en espuma de poliuretano.
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
CN104395367A (zh) * 2012-07-26 2015-03-04 东曹株式会社 聚异氰酸酯化合物固化用胺催化剂及含有该胺催化剂的聚异氰酸酯粘接剂组合物
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
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
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
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
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

Also Published As

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

Similar Documents

Publication Publication Date Title
KR930017934A (ko) 폴리우레탄 제조용 악취 경감 촉매로서의 히드록시기-함유 아민-붕소 첨가 생성물
US5240970A (en) Quaternary ammonium carboxylate inner salt compositions as controlled activity catalysts for making polyurethane foam
US4433170A (en) Novel bis(aminoethyl)ether derivatives useful as polyurethane catalysts
US4094827A (en) Substituted ureas as polyurethane catalysts
DE69800484T2 (de) N,N,N'-trimethylbis(aminoethyl)ether-substituierte Harnstoffzusammensetzungen für die Herstellung von Polyurethanen
EP0088377B1 (en) Carbamate and carbonate salts of tertiary amines
KR950025049A (ko) 폴리우레탄 제조용 히드록시-작용성 트리아민 촉매 조성물
DE69607711T2 (de) Aminopropylbis(aminoethyl)etherzusammensetzungen zur Herstellung von Polyurethanen
CA2533513A1 (en) Low-odor catalyst for isocyanate-derived foams and elastomers
US4464488A (en) Polyurethanes using monocarboxylic acid salts of bis(aminoethyl)ether derivatives as catalysts
CN105504198A (zh) 改善了水解稳定性的含聚酯多元醇的聚氨酯体系
BRPI0601355A (pt) método para produzir poliuretana espumada, e método para catalisar uma reação emtre um composto isocianato orgánico e um composto contendo hidrogênio ativo
MXPA96004243A (es) Composiciones de aminopropilbis(aminoetil)eterpara la produccion de poliuretanos
KR930016458A (ko) 폴리우레탄 포움의 제조를 위한 3-퀴누클리디놀 촉매 조성물
US5155248A (en) Polyurethane catalysts
Ruiduan et al. Research progress of amine catalysts for polyurethane
EP0816408A1 (en) Hydroxyalkylbis(aminoethyl)ether compositions for the production of polyurethanes
US5238894A (en) Hydroxyl group-containing amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes
US5212306A (en) Amine-borate and amine-boron halide complexes as catalyst compositions for the production of polyurethanes
US5710191A (en) Hydroxymethyl quinuclidine catalyst compositions for making polyurethane foams
US6998508B2 (en) Tertiary alkanolamines containing surface active alkyl groups
EP0668303B1 (en) Hydroxy functional pyrrolizidine catalyst compositions for the production of polyurethanes
DE69601328T2 (de) Hydroxymethylchinuclidin-Katalysatorzusammensetzungen zur Herstellung von Polyurethanschäumen
US5248646A (en) Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes
US5322940A (en) Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
G160 Decision to publish patent application
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20040714

Year of fee payment: 9

LAPS Lapse due to unpaid annual fee