KR970059178A - 중합가능 디케토피롤로피를 및 그를 사용하여 제조된 중합체 - Google Patents

중합가능 디케토피롤로피를 및 그를 사용하여 제조된 중합체 Download PDF

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KR970059178A
KR970059178A KR1019970002635A KR19970002635A KR970059178A KR 970059178 A KR970059178 A KR 970059178A KR 1019970002635 A KR1019970002635 A KR 1019970002635A KR 19970002635 A KR19970002635 A KR 19970002635A KR 970059178 A KR970059178 A KR 970059178A
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alkyl
diketopyrrolopyrrole
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사메어 호삼 엘딘
아불 이크발
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이. 알테르, 에이치. 피. 위틀린
시바 스페셜티 케미칼스 홀딩 인크.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F246/00—Copolymers in which the nature of only the monomers in minority is defined
    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
    • C08G18/3844—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing one nitrogen atom in the ring
    • 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
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes

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Abstract

본 발명은 중합가능 반응기를 포함하는 신규의 하기 화학식(1)의 1,4-케토피롤로피롤 및 그의 중합체에 관한 것이다.
상기 식에서 A 및 B는 서로 독립적으로 하기 화학식의 기로 이루어지는 군 중에서 선택되는 기이고,
R3 및 R4는 서로 독립적으로 수소, 할로겐, C1-C18알킬, C1-C18알콕시, C1-C18알킬메르캅토, C1-C18알킬아미노, C1-C18알콕시카르보닐, C1-C18알킬아미노카르보닐, -CN, -NO2, 트리플루오로메틸, C5-C6시클로알킬, -C=N-(C1-C18알킬),이미다졸릴, 피라졸릴, 트리아졸릴, 피페라지닐, 피롤릴, 옥사졸릴, 벤즈옥사졸릴, 벤조티아졸릴, 벤즈이미다졸릴, 모르폴리닐, 피페리디닐 또는 피롤리디닐이고, G는 -CH2-, -CH(CH3)-, -C(CH3)2-, -CH=N-, -N=N-, -O-, -S-, -SO-, 0S2-, -CONH- 또는 -NR9-이고, R5및 R6은 서로 독립적으로 수소, 할로겐, 또는 C1-C6알킬이고, R9는 수소 또는 C1-C6알킬이고, R1은 중합가능 반응기를 포함하는 탄소 원자수 4 이상의 라디칼이고, R2는 C1-C6알킬,또는 R1이다. 본 발명의 신규 디케토피롤로피롤은 중합체와 용이하게 반응할 수 있는 DPP 발색단을 얻거나 또는 동종중합 또는 공중합에 의해 직접 또는 기존의 선형성된 동종중합체 또는 공중합체 상에 대한 그라프팅(grafting)에 의해 중합체를 형성할 수 있고 유리한 색상 효과를 갖는 유색 중합체의 제조에 적합하다.

Description

중합가능 디케토피롤로피롤 및 그를 사용하여 제조된 중합체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 화학식(1)의 1,4-디케토피롤로피롤.
    상기 식에서, A 및 B는 서로 독립적으로 하기 화학식의 기 중에서 선택되는 기이고,
    R3및 R4는 서로 독립적으로 수소, 할로겐, C1-C18알킬, C1-C18알콕시, C1-C18알킬메르캅토, C1-C18알킬아미노, C1-C18알콕시카르보닐, C1-C18알킬아미노카르보닐, -CN, -NO2, 트리플루오로메틸, C5-C6시클로알킬, -C=N-(C1-C18알킬),이미다졸릴, 피라졸릴, 트리아 졸릴, 피페라지닐, 피롤릴, 옥사졸릴, 벤즈옥사졸릴, 벤조티아졸릴, 벤즈이미다졸릴, 모르폴리닐, 피페리디닐 또는 피롤리디닐이고, G는 -CH2-, -CH(CH3)-, -C(CH3)2-, -CH=N-, -N=N-, -O-, -S-, -SO-, -SO2-, -CONH- 또는 -NR9-이고, R5및 R6는 서로 독립적으로 수소, 할로겐, C1-C6알킬, C1-C18알콕시 또는 -CN이고, R7및 R8은 서로 독립적으로 수소 할로겐 또는 C1-C8알킬이고, R9는 수소 도는 C1-C6알킬이고, R1은 중합가능 반응기를 포함하는 탄소 원자수 4 이상의 라디칼이고, R2는 C1-C6알킬,또는 R1이다.
  2. 제1항에 있어서, R1이 하기 화학식(2) 또는 (3)의 라디칼인 화학식(1)의 디케토피콜로피롤.
    -(CH2)m-CH=CH-(CH2)n-CH3(2)
    -(Y)p-X-(Z)r-Q (3)
    상기 식에서, m 및 n은 서로 독립적으로 0 내지 12의 정수이되, 그 합계(m+n)는 적어도 4이고, p 및 r은 서로 독립적으로 0 또는 1이고, X는 방해되지 않은 C4-C18알킬렌이거나 또는 -O- 및(또는) -S-, -NH-, 페닐렌, -COO-, -CONH- 또는에 의해 1회 이상 방회된 C4-C18알킬렌이고, R10은 수소 또는 메틸이고, Y는-Si(Cl)2-, -Si(OC2H5)2-, -CH2-CH(OH)- 또는 -CH(CN)-이고, Z는 -O-, -NH-, -COO-, 페닐렌, -NHCO-Si(Cl)2-, -Si(OC2H5)2-, 또는 -Si(OCOCH3)2-이고, Q는 -OH, -NH2, 글리시딜,-CHO, -NCO, -CH=CH2, -C(CH3)=CH2, -CO-CH=CH2-CO-C(CH3)=CH2, C5-C7시클로알케닐,-CONHR11, -COOR11또는 -COR11(여기서, R11은 수소 또는 C1-C6알킬임)이거나 또는 Q는(여기서, s는 1내지 6의 정수임)이다.
  3. 제1항에 있어서, 화학식(1)에서 A 및 B가 서로 독립적으로 하기 화학식의 기 중에서 선택되는 기인 디케토피롤로피롤.
    상기 식에서, R3및 R4는 서로 독립적이고, 수소, 할로겐, 특히 염소 또는 브롬, C1-C4알킬, C1-C6알콕시, C1-C6알킬아미노 또는 CN이고, G는 -O-, -NR9-, -N=N- 또는 -SO2-이고, R5및 R6은 수소이고, R9는 수소, 메틸 또는 에틸이다.
  4. 제3항에 있어서, 화학식(1)에서 A 및 B가 서로 동일하고 하기 화학식의 기인 디케토피롤로피롤.
    상기 식에서, R3및 R4는 서로 독립적으로 수소, 메틸, t-부틸, 연소, 브롬 또는 CN이다.
  5. 제2항에 있어서, 화학식(1)에서, R1이 하기 화학식(4)의 기인 디케토피롤로피롤. -X-(O)r-Q (4)
    상기 식에서, X는 방해되지 않은 C4-C12알킬렌이거나 또는 -O-에 의해 1,2 또는 3회 및(또는) -S-, -NH- 또는에 의해 1회 방해된 C4-C12알킬렌이고, r 및 R10은 제1항에서 정의된 의미를 갖고, Q는 -OH, -CH=CH2, -C(CH3)=CH2, -CO-CH=CH2또는 -CO-C(CH3)=CH2이다.
  6. 제5항에 있어서, X가 바람직하게는 -(CH2)q- (여기서, q는 6내지 12의 정수일 수 있음), -(CH2CH2O)2-CH2CH2- 또는인 디케토피롤로피롤.
  7. 피롤리논을 니트릴과 반응시켜 제1항 내지 6항에 따른 디케토피롤로피롤을 제조하는 방법으로, (a) 하기 화학식(5)의 피롤리논을 하기 화학식(6)의 니트릴과 반응시키고 (a1) 생성되는 디케토피롤로피롤을 하기 화학식(7)의 화합물과 반응시키거나, 또는 화학식(3)의 기에서 Y가 제2항에서 정의된 바와 같이 -CH2-CH(OH)-인 경우에는 하기 화학식(8)의 화합물과 반응시키거나, 또는 (a2) 하기 화학식(9)의 디케토피롤로피롤을 (a1)에 대응하는 방법으로 화학식(7) 및 (8)의 화합물과 반응시키거나, 또는 (b) R1이 제2항에서 정의한 바와 같은 화학식(3) (여기서, Q는 -OH임)의 라디칼인 화학식(1)의 디케토피롤로피롤을 아크릴로일 클로라이드 또는 메티크롤로일클로라이드와 반응시키는 것을 특징으로 하는 방법.
    상기 식에서, R은 바람직하게는 C1-C4알킬이고, A 및 B는 제1항의 의미를 갖고, R1은 제2항에서 정의된 바와 같은 화학식(2) 또는 (3)의 라디칼이고, R2는 제1항에서 정의된 바와 같은 C1-C6알킬 또는이고, X,Z,Q 및 r은 제2항에서 정의된 의미를 갖고, Hal은 바람직하게는 염소 또는 브름이다.
  8. 화학식(1)의 디케토피롤로피롤을 필요한 경우 적합한 공단량체 또는 중합 가능기를 갖는 중합체의 존재하에 중합하는 것으로 이루어지는 중합 반응 또는 중합 체-유사체 반응에 의한 중합체의 제조 또는 개질 방법.
  9. 제1항 내지 6항에 따른 디케토피롤로피롤 또는 제7항에 따라 제조도니 디케토피롤로피롤의 중합 반응 또는 중합체-유사체 반응에 의한 중합체의 제조 ㄸ는 개질을 위한 용도.
  10. 제1항 내지 6항에 따른 디케토피롤로피롤 또는 제7항에 따라 제조된 디케토리롤로피롤을 사용하여 개질되거나 제조된 중합체.
    ※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019970002635A 1996-01-30 1997-01-29 중합가능한디케토피롤로피롤및그를사용하여제조된중합체 KR100460247B1 (ko)

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CN1165823A (zh) 1997-11-26
US6048918A (en) 2000-04-11
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US5847156A (en) 1998-12-08
EP0787731B1 (de) 2002-08-07
TW407149B (en) 2000-10-01
EP0787731A3 (de) 1997-08-13
DE59707889D1 (de) 2002-09-12
CA2196137A1 (en) 1997-07-31

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