KR920011983A - 디히드록시 화합물과 에폭사이드의 부가물의 제조방법 - Google Patents

디히드록시 화합물과 에폭사이드의 부가물의 제조방법 Download PDF

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KR920011983A
KR920011983A KR1019910021824A KR910021824A KR920011983A KR 920011983 A KR920011983 A KR 920011983A KR 1019910021824 A KR1019910021824 A KR 1019910021824A KR 910021824 A KR910021824 A KR 910021824A KR 920011983 A KR920011983 A KR 920011983A
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triflate
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마틴 롤프 윌리엄
로버트 도즈비 마이클
도빈슨 브라이언
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베르너 발데크
시바-가이기 아게
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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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
    • C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
    • C08G59/066—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with chain extension or advancing agents
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols
    • C08G59/621—Phenols
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/687—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing sulfur

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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)
  • Epoxy Resins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyethers (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Catalysts (AREA)

Abstract

내용 없음

Description

디히드록시 화합물과 에폭사이드의 부가물의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (21)

  1. a)촉매로서(IUPAC 1970 협약에 따른) 원소주기율표의 ⅡA, ⅡB, ⅢA, ⅢB 또는 ⅧA족 금속 트리플레이트염의 존재하에 디히드록시 화합물과 디에폭사이드를 반응시키고, b)트리플레이트 염 촉매를 불활성화시키며; 또 c)임의적으로 방향족 디올 또는 페놀로 단계 b)에서 제조한 물질을 가공하는 것을 포함하는, 디에록사이드 출발 물질에 비해 증가된 분자량을 갖는 히드록시-말달 또는 에폭시-말단 물질의 제조방법.
  2. 제1항에 있어서, ⅡB족 금속 트리플레이트 촉매가 마그네슘 트리플레이트이고; ⅡB족 금속 촉매가 아연 또는 카드뮴 트리플레이트이고, ⅢA족 금속 촉매가 란단 트리플레이트이며, ⅢB족 금속 촉매가 알루미늄 트리폴레이트이고, ⅧA족 금속 촉매가 코발트 트리플레이트인 방법.
  3. 제1항에 있어서, 금속 트리플레이트 촉매의 사용량이 반응 혼합물의 총 중량에 대해 20 내지 200ppm인 방법.
  4. 제1항에 있어서, 금속 트리플레이트 촉매를 유기 용매중의 용액 상태로 사용하는 방법.
  5. 제4항에 있어서, 유기 용매가 방향족 탄화수소 용매: 시클로지방족 극성 용매; 또는 극성 지방족 용매인 방법.
  6. 제1항 내지 제5항중 어느 하나에 있어서, 디히드록시 화합물 반응물이 하기 일반식(Ⅰ)의 화합물인 방법 :
    Q(OH)2(Ⅰ)
    상기 식에서, Q는 2가 지방족, 시클로지방족 또는 방향지방족 잔기이다.
  7. 제6항에 있어서, Q가 직쇄 또는 측쇄 C2-C12알킬렌 잔기; 브리지 멤버를 통해 함께 결합된 수개의 시클로알킬렌 잔기를 포함할 수 있는, 임의적으로 치환된 C5-C8시클로알킬렌 잔기, 또는임의적으로 고리-치환된 벤질 잔기인 방법.
  8. 제6항 또는 제7항에 있어서, 지방족 디히드록시 화합물이 에틸렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜 또는 고급 폴리옥시에틸렌 글리콜; 프로판-1, 2-디올; 프로판-1, 3-디올 또는 고급 폴리시프로필렌 글리콜, 부탄-1, 4-디올, 또는 고급 폴리옥시테트라메틸렌 글리콜, 네노펜틸 글리콜, 펜탄-1, 5-디올, 헥산-1, 6-디올, 옥탄-1, 8-디올; 또는 폴리(카프로락톤)인 방법.
  9. 제5항 또는 제6항에 있어서, 시클로지방족 디히드록시 화합물이 퀴니를, 레조르시톨, 비스(4-히드록시시클로헥실)메탄, 2, 2-비스(4-히드록시시클로헥실)프로판, 시클로헥산 디메탄올 1, 1-비스(히드록시메틸)시클로헥스-3엔 또는 4, 9-비스(히드록시메틸)트리스클로〔5, 2, 1, 02, 6〕인 방법.
  10. 제6항 또는 제7항에 있어서, 방향지방족 디히드록시 화합물이 1, 4-벤젠디메탄올 또는 4, 4´-비스(히드록시메틸)비페닐인 방법.
  11. 제1항 내지 제10항중 어느 하나에 있어서, 디에폭사이드 반응물이 디글리시딜 에테르 또는 디글리시딜 에스테르인 방법.
  12. 제11항에 있어서, 디에폭사이드가 2, 2-비스(4-히드록시페닐)프로판의 디글리시딜 에테프, 비스(4-히드록시페닐)메탄의 디글리시딜 에테르 또는 고리에서 한 개의 C1-C9알킬기 또는 페닐, 팬에틸 또는 메틸펜에틸기에 의해 임의적으로 치환된 페놀과 포름알데히드로부터 제조되고, 1, 2-에폭사이드 함량이 kg당 1.0당량 이상인 노블락의 디글리시딜 에테르인 방법.
  13. 제1항 내지 제12항중 어느 하나에 있어서, 단계b)에서, 알칼리금속 수산물을 첨가하거나 또는 금속착화제를 첨가함으로써 트리플레이트 염 촉매를 불활성화 시키는 방법.
  14. 제13항에 있어서, 금속 착화제가 8-히드록시퀴놀린인 방법.
  15. 제1항 내지 제14항중 어느 하나에 있어서, 방향족 다올 반응물이 비스(4-히드록시페닐)메탄(비스페놀F), 비스(4-히드록시페닐)술폰, 2, 2-비스(4-히드록시페닐)프로판(비스페놀 A) 또는 2, 2-(3, 5-디브로모-4-히드록시페닐)프로판인 방법.
  16. 제1항 내지 제15항중 어느 하나에 있어서, 방법의 단계 c)에서 방향족 디올 반응물에 대한 단계 b)의 생성물의 몰비가 0.5:1 내지 50:1인 방법.
  17. 제1항 내지 제16항중 어느 하나에 있어서, 염기의 존재하에 임의적으로는 불활성 용매의 존재하에 100℃ 내지 200℃에서 반응물을 가열함으로써 방법의 단계 c)를 실행하는 방버.
  18. 1)제1항 내지 제17항중 어느 하나에 따른 방법에 의해 제조되는 히드록시-말단 또는 에폭시-말단 생성물 및 2)생성물 1)용의 경화제를 포함하는 경화성 조성물.
  19. 제18항에 있어서, 경화제가 카르복시산 또는 무수물, 및 이들의 혼합물; 불포화 지방산으로부터 유도된 이합체 또는 삼합체 산; 프리델 크라프츠 금속 할라이드 또는 이들과 에테르, 산 무수물, 케톤 또는 아민의 착물; 염; 지방족, 방향족, 방향지방족 또는 헤테로고리형 아미노 화합물, 또는 아민과 폴리에폭사이드의 가용성 부가물 및 이들의 염; 활성 아미노기 및/또는 카르복시기기를 함유하는 폴리아미드; 카르복시산 히드라지드 1-시아노-3-알킬구아니딘; 이미다졸; 3차 아민과 히드록시키르복시산의 염; 시안아세트아미드; 숙신아미드; 아미노플라스트; 페놀 포름알데히드 수지; 또는 블록된 플리이소시아네이트인 조성물.
  20. 제18항 또는 제19항에 있어서, 경화제가 아민이고 아민 경화제의 양이 성분 1)100중량부에 대해 1.0 내지 50중량부이거나; 또는 경화제가 프리델 크라프츠 촉매의 착물이고 착물의 양이 성분 1)100중량부에 대해 0.5 내지 10중량부인 조성물.
  21. 제18항 또는 제19항에 있어서, 경화제가 무수물이고, 성분 1)100중량부에 대해 0.1 내지 5중량부의 촉진제가 또한 존재하는 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.
KR1019910021824A 1990-12-18 1991-11-27 디히드록시 화합물과 에폭사이드의 부가물의 제조방법 KR100210258B1 (ko)

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Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4310198A1 (de) * 1993-03-29 1994-10-06 Hoechst Ag Polyol-Epoxid Additionsprodukte zur Verwendung als Emulgator für flüssige Epoxidharze
DE69420047T2 (de) * 1993-12-21 1999-11-25 The Dow Chemical Co., Midland Verfahren für die reaktion von epoxidgruppen enthaltenden verbindungen mit aliphatischen alkoholen
WO1996024628A1 (en) * 1995-02-10 1996-08-15 Dow Deutschland Inc. Epoxy resin composition capable of cure at low temperature
DE19547786A1 (de) * 1995-12-20 1997-06-26 Basf Lacke & Farben Aufbau von modifizierten Epoxidharzen für die kathodische Elektrotauchlackierung mit Katalysator-Desaktivierung und Diolmodifizierung
DE19621703A1 (de) * 1996-05-30 1997-12-04 Hoechst Ag Verfahren zur Herstellung von 3-Oxyalkylpropan-1-olen
AU744290B2 (en) * 1997-08-26 2002-02-21 Ranbar Electrical Materials, Inc. Varnish compositions, methods of making and components made therefrom
ES2154165B1 (es) * 1998-08-06 2001-10-16 Univ Rovira I Virgili Composicion para el entrecruzamiento de resinas epoxi.
US6492565B2 (en) 1998-10-07 2002-12-10 Bayer Aktiengesellschaft Process for the preparation of polyether polyols
BR9914676A (pt) * 1998-10-22 2001-07-17 Vantico Ag Composições de resina epóxi curáveis
GB9913627D0 (en) 1999-06-12 1999-08-11 Ciba Geigy Ag Process for the preparation of reaction products of cycloaliphatic epoxides with multifunctional hydroxy compounds
US20020151626A1 (en) * 2001-02-08 2002-10-17 Hisashi Isaka Curing composition
GB0200505D0 (en) * 2002-01-10 2002-02-27 Vantico Ag Highly functional polymers
US7208551B2 (en) * 2003-08-18 2007-04-24 University Of Dayton Polyaryleneetherketone phosphine oxide compositions incorporating cycloaliphatic units for use as polymeric binders in thermal control coatings and method for synthesizing same
GB0809439D0 (en) 2008-05-23 2008-07-30 Qinetiq Ltd Novel curing method
EP2385962B1 (en) * 2009-01-06 2015-09-02 Dow Global Technologies LLC Metal stabilizers for epoxy resins and advancement process
CN102333801B (zh) 2009-03-05 2015-11-25 阿克佐诺贝尔国际涂料股份有限公司 羟基官能油多元醇丙烯酸类接枝共聚物
CN103998480B (zh) 2011-12-21 2016-10-19 阿克佐诺贝尔国际涂料股份有限公司 溶剂基涂料组合物
MX367934B (es) 2011-12-21 2019-09-12 Akzo Nobel Coatings Int Bv Composiciones de recubrimiento a base de agua.
TWI768823B (zh) * 2020-04-09 2022-06-21 南韓商可隆工業股份有限公司 用於輪胎簾線的黏著劑組成物、輪胎簾線及輪胎
CZ2021507A3 (cs) * 2021-11-04 2023-05-17 Synpo, A.S. Epoxy resins

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4115295A (en) * 1976-04-26 1978-09-19 Minnesota Mining And Manufacturing Company Polymerizable compositions containing highly fluorinated aliphatic sulfonyl protonic acid catalyst
US4352918A (en) * 1980-12-04 1982-10-05 The Dow Chemical Company Process for preparing epoxy resins having improved physical properties when cured using quaternary phosphonium catalysts
US4416917A (en) * 1981-01-30 1983-11-22 Union Carbide Corporation Coating substrates with high solids compositions
US4465722A (en) * 1982-07-08 1984-08-14 Ciba-Geigy Corporation Process for the preparation of epoxide resins by the advancement method
FR2536069A1 (fr) * 1982-11-17 1984-05-18 Bp Chimie Sa Procede de preparation de produits d'addition d'epoxydes et de composes hydroxyles
US4707535A (en) * 1983-10-27 1987-11-17 Union Carbide Corporation Low viscosity adducts of a poly(active hydrogen) organic compound and polyepoxide
US5019639A (en) * 1987-04-07 1991-05-28 Ciba-Geigy Corporation Novel epoxy resins
US4820784A (en) * 1988-01-13 1989-04-11 The Dow Chemical Company Modified advanced epoxy resins
DE58909349D1 (de) * 1988-09-29 1995-08-24 Ciba Geigy Ag Epoxidharzgemische.

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ES2099142T3 (es) 1997-05-16
EP0493916B1 (en) 1997-03-12
EP0493916A3 (en) 1992-11-25
EP0493916A2 (en) 1992-07-08
KR100210258B1 (ko) 1999-07-15
DE69125131T2 (de) 1997-10-30
GB9027406D0 (en) 1991-02-06
TW226386B (ko) 1994-07-11
JP3277256B2 (ja) 2002-04-22
US5362835A (en) 1994-11-08
BR9105435A (pt) 1992-09-22
JPH04314719A (ja) 1992-11-05
DE69125131D1 (de) 1997-04-17

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