KR940009146A - 지환식 구조를 갖는 불포화 이미드 화합물, 이의 제조방법 및 이를 위한 중간체 - Google Patents

지환식 구조를 갖는 불포화 이미드 화합물, 이의 제조방법 및 이를 위한 중간체 Download PDF

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KR940009146A
KR940009146A KR1019930022528A KR930022528A KR940009146A KR 940009146 A KR940009146 A KR 940009146A KR 1019930022528 A KR1019930022528 A KR 1019930022528A KR 930022528 A KR930022528 A KR 930022528A KR 940009146 A KR940009146 A KR 940009146A
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formula
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KR1019930022528A
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야스히로 히라노
야스히로 엔도
가즈오 다께베
미쓰히로 시바따
스이찌 가나가와
유따까 시오미
마사쓰구 아끼바
시니찌로 기따야마
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고오사이 아끼오
스미또모가가꾸고오교 가부시끼가이샤
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Priority claimed from JP29003692A external-priority patent/JPH06135905A/ja
Priority claimed from JP30361692A external-priority patent/JPH06157457A/ja
Priority claimed from JP31024792A external-priority patent/JPH06157680A/ja
Priority claimed from JP5121136A external-priority patent/JPH06329629A/ja
Priority claimed from JP12588893A external-priority patent/JPH06336475A/ja
Application filed by 고오사이 아끼오, 스미또모가가꾸고오교 가부시끼가이샤 filed Critical 고오사이 아끼오
Publication of KR940009146A publication Critical patent/KR940009146A/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/10—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
    • C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/12—Unsaturated polyimide precursors

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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)
  • Indole Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

본 발명은 하기식(1) :
(상기식에서, Q는 탄소수 4∼20인 지환식 구조-함유 탄화수소기이고; R1,R2,R3,R4, Ri및 Rj각각은 수소원자, 할로겐원자, 탄소수 1∼6의 탄화 수소기 또는 탄소수 1∼6의 할로겐-함유 탄화 수소기이며; a,b,c,d,e 및 f 각각은 a+b≤4, c+d≤이고 e+f≤4의 조건을 만족하는 0∼4의 정수를 나타내고; D는 에틸렌계 불포화 이중결합을 갖는 탄소수 2∼24의 2가 유기기이다)로 표시되는 불포화 이미드 화합물, 일반식(1)의 불포화 이미드 화합물의 제조방법 및 일반식(1)의 불포화 아미드 화합물의 제조를 위한 중간체에 관한 것이다. 일반식(1)의 불포화 이미드 화합물은 유기 용매에 잘 용해되고, 내열성, 저흡수성 및 유연성이 우수한 경화 제품을 제공할 수 있다.

Description

지환식 구조를 갖는 불포화 이미드 화합물, 이의 제조방법 및 이를 위한 중간체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (14)

  1. 하기식(1)로 나타내는 불포화 이미드 화합물:
    상기식에서, Q는 탄소수 4∼20인 지환식 구조-함유 탄화 수소기이고; R1,R2,R3,R4,Ri및 Rj각각은 수소원자, 할로겐원자, 탄소수 1∼6의 탄화 수소기 또는 탄소수 1∼6의 할로겐-함유 탄화 수소기이며; a,b,c,d,e 및 f 각각은 a+b≤4, c+d≤이고 e+f≤4의 조건을 만족하는 0∼4의 정수를 나타내고; D는 에틸렌계 불포화 이중 결합을 갖는 탄소수 2∼24의 2가 유기기이다.
  2. 제1항에 있어서, 일반식(1)중의 Q가 하기식(a),(b) 또는 (c)로 나타내는 기인 불포화 이미드 화합물:
  3. 하기식(2)로 나타내는 디아미노 화합물을 하기식(3)으로 나타내는 불포화 디카르복실산 무수물과 반응시켜, 하기식(4)로 나타내는 암산화합물을 얻은 다음, 산 촉매의 존재하에서 비양자성 극성 용매하에 암산 화합물을 가열시켜 탈수-폐환반응을 야기시키는 과정을 포함하는 일반식(1)로 나타내는 불포화 이미드 화합물의 제조방법:
    (상기식에서, Q,R1,R2,R3,R4,Ri,Rj,D,a,b,c,d,e 및 f는 제1항에서 정의한 바와 같다).
  4. 제3항에 있어서, 일반식(2)의 디아미노 화합물이, 일반식(6)으로 나타내는 비스페놀을 일반식(7)로 나타내는 니트로벤젠 유도체와 반응시켜 얻어진 일반식(5)의 디니트로 화합물을 환원하여 제조되는 방법.
    (상기식에서, Q,R1,R2,R3,R4,Ri,Rj,D,a,b,c,d,e 및 f는 제1항에서 정의한 바와 같고, X는 할로겐원자 또는 니트로기이다).
  5. 제4항에 있어서, 일반식(7)의 니트로벤젠 유도체가 비양자성 극성 용매하에서 일반식(6)의 비스페놀과 반응시켜 일반식(5)의 디니트로 화합물을 함유하는 혼합물을 얻은 다음; 일반식(5)의 디니트로 화합물을 분리하지 않고, 얻어진 혼합물 자체에 환원 과정을 행하여 일반식(2)의 디아미노 화합물을 함유하는 혼합물을 얻고; 일반식(2)의 디아미노 화합물을 분리하지 않고, 얻어진 혼합물 자체를 일반식(3)의 불포화 디카르복실산 무수물과 반응시키는 방법.
  6. 제3항에 있어서, 일반식(2)의 디아미노 화합물을 일반식(3)의 불포화 디카르복실산 무수물과 반응시켜 얻어진 일반식(4)의 암산 화합물의 아미드화 반응을 2단계로 수행하는데, 제1단계에서는, 산촉매의 존재하에 60∼120℃의 온도에서 암산 산화물에 예비적 반응을 행하면서 형성된 물을 공비 탈수에 의하여 계외로 제거하고, 제2단계에서는 120℃이상의 온도에서 제1단계에서 얻어진 반응 혼합물에 반응을 행하면서 형성된 물을 공비 탈수에 의하여 제거하는 방법.
  7. 제6항에 있어서, 이미드화 반응이 물과 함께 공비 증류될수 있는 비양자성 극성용매와 하나 이상의 유기용매로 구성된 혼합 용매하에서 수행되고, 제1단계 반응이 감압하에 수행되는 방법.
  8. 제6항에 있어서, 일반식(3)의 불포화 디카르복실산 무수물이 말레산 무수물이고, 이미드화 반응이 비양자성 극성 용매와 할로겐화 방향족 탄화수소의 혼합용매하에 수행되는 방법.
  9. 필수 성분으로서, (a) 제1항에서 정의한 바와 같은 일반식(1)의 불포화 이미드 화합물 및 (b)경화 촉진제를 함유하는 열경화성 수지 조성물.
  10. 필수성분으로서, (a) 제1항에서 정의한 바와 같은 일반식(1)의 불포화 이미드 화합물, (b) 경화 촉진제, (c) 에폭시 수지 및 (d) 에폭시 수지경화제를 함유하는 열경화성 수지 조성물.
  11. 제9항에서 정의한 바와 같은 열경화성 수지 조성물로 봉합된 전자부품.
  12. 제10항에서 정의한 바와 같은 열경화성 수지 조성물로 봉합된 전자부품.
  13. 하기 일반식(5)로 나타내는 디니트로 화합물:
    (상기식에서, Q,R1,R2,R3,R4,Ri,Rj,a,b,c,d,e 및 f는 제1항에서 정의한 바와 같다).
  14. 하기 일반식(2)로 나타내는 디아미노 화합물:
    (상기식에서, Q,R1,R2,R3,R4,Ri,Rj,a,b,c,d,e 및 f는 제1항에서 정의한 바와 같다).
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930022528A 1992-10-28 1993-10-27 지환식 구조를 갖는 불포화 이미드 화합물, 이의 제조방법 및 이를 위한 중간체 KR940009146A (ko)

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
JP29003692A JPH06135905A (ja) 1992-10-28 1992-10-28 脂環式構造を有する芳香族ニトロ化合物類および芳香族アミノ化合物類ならびにそれらの製造方法
JP92-290036 1992-10-28
JP30361692A JPH06157457A (ja) 1992-11-13 1992-11-13 脂環式構造を有する不飽和イミド系化合物およびその製造方法
JP92-303616 1992-11-13
JP92-310247 1992-11-19
JP31024792A JPH06157680A (ja) 1992-11-19 1992-11-19 熱硬化性樹脂組成物およびその用途
JP5121136A JPH06329629A (ja) 1993-05-24 1993-05-24 脂環構造を含む不飽和イミド系化合物の製造方法
JP93-121136 1993-05-24
JP12588893A JPH06336475A (ja) 1993-05-27 1993-05-27 不飽和イミド化合物の製造方法
JP93-125888 1993-05-27

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KR940009146A true KR940009146A (ko) 1994-05-20

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US (4) US5326881A (ko)
EP (1) EP0595230A1 (ko)
KR (1) KR940009146A (ko)
CA (1) CA2109347A1 (ko)
SG (1) SG45160A1 (ko)
TW (1) TW260682B (ko)

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US5734008A (en) * 1994-10-28 1998-03-31 Sumitomo Chemical Company, Limited Polyimide film
FR2812651B1 (fr) * 2000-08-01 2002-09-27 Atofina Composition pour la preparation a froid au collage de materiaux composites
US7771827B2 (en) * 2001-08-27 2010-08-10 Arkema France Composition for the cold preparation of composite materials for adhesive bonding
KR100638623B1 (ko) * 2001-09-04 2006-10-26 미쓰이 가가쿠 가부시키가이샤 신규한 방향족 디아민 및 그의 폴리이미드
WO2003107084A1 (ja) * 2002-06-14 2003-12-24 大日本インキ化学工業株式会社 液晶パネルシール用光硬化性組成物及び液晶パネル
JP4360885B2 (ja) 2003-11-28 2009-11-11 富士フイルム株式会社 アルキルチオ基を有する芳香族アミン化合物の製造方法
JP4793565B2 (ja) * 2005-03-24 2011-10-12 信越化学工業株式会社 半導体封止用エポキシ樹脂組成物及び半導体装置

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US3232994A (en) * 1962-12-27 1966-02-01 Union Carbide Corp Novel bisphenols and preparation thereof using ion exchange resins
CH597184A5 (ko) * 1976-04-09 1978-03-31 Ciba Geigy Ag
FR2399412A1 (fr) * 1977-08-05 1979-03-02 France Etat Bis-imide a base d'adamantane et procede pour sa fabrication
JPS56103162A (en) * 1980-01-21 1981-08-18 Hitachi Ltd Ether-imide and its preparation
JPS57159764A (en) * 1981-03-28 1982-10-01 Ihara Chem Ind Co Ltd Preparation of bismaleimide compound
AU566103B2 (en) * 1985-02-22 1987-10-08 Mitsui Chemicals, Inc. Bis(3-aminophenoxy) aromatics and method of preparing the same
GB2223491B (en) * 1988-09-22 1992-01-29 Central Glass Co Ltd Fluorine-containing bismaleamic acids and bismaleimides useful for thermosetting resins
US5149761A (en) * 1988-10-12 1992-09-22 Bayer Aktiengesellschaft Aromatic ether imides
JPH0670101B2 (ja) * 1988-11-28 1994-09-07 三井東圧化学株式会社 熱硬化性樹脂組成物
CA2028312C (en) * 1990-04-11 1996-03-12 Norimasa Yamaya Thermosetting resin forming composition and process for preparing same

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US5498687A (en) 1996-03-12
TW260682B (ko) 1995-10-21
US5326881A (en) 1994-07-05
EP0595230A1 (en) 1994-05-04
SG45160A1 (en) 1998-01-16
US5444165A (en) 1995-08-22
CA2109347A1 (en) 1993-11-25
US5750789A (en) 1998-05-12

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