KR890009953A - 티타노센, 그의 용도 및 n-치환된 플루오로아닐린 - Google Patents

티타노센, 그의 용도 및 n-치환된 플루오로아닐린 Download PDF

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KR890009953A
KR890009953A KR1019880016123A KR880016123A KR890009953A KR 890009953 A KR890009953 A KR 890009953A KR 1019880016123 A KR1019880016123 A KR 1019880016123A KR 880016123 A KR880016123 A KR 880016123A KR 890009953 A KR890009953 A KR 890009953A
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titanocene
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리에디커 마르틴
스타이너 에긴하드
베이엘러 하리
시태크 프란시스제크
휘슬러 리날드
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데오볼싱게르
시바-가이기 아게
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Abstract

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티타노센, 그의 용도 및 N-치환된 플루오로아닐린
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Claims (30)

  1. 하기 일반식(Ⅰ)의 티타노센.
    상기식에서, R1라디칼 모두는 서로 독립헤서 시클로렌타디엔일,인덴일또는 4,5,6,7-테트라히드로인덴일이며 이들의 각각은 비치환되거나 또는 C1-C18알킬, C1-C18알콕시,C2-C18알켄일, C5-C8시클로알킬, C6-C16아릴, C7-C16아르알킬,시아노 또는 할로겐에 의하여 치환되며, 또는 R1모두가 합쳐져서 상기와 같이 비치환되거나 또는 치환된 하기 일반식(Ⅱ)의 라디칼
    (X는 n이 1,2 또는 3인 -(-CH2-)n2내지 12개 탄소원자를 갖는 비치환되거나 또는 페닐치환된 알킬리덴, 5 내지 7개 고리탄소원자를 갖는 시클로알킬리덴,이고; 또 R4는 C1-C12알킬,C5-C12시클로알킬, C6-C16아릴 또는 C7-C17아르알킬임)을 형성하고; R2는 6-윈 카르보시클릭 또는 티탄-탄소 결합에 대한 2개의 오르토 위치중 적어도 1개에서 플루오로 원자에 의하여 치환된 5- 또는 6-윈 헤테로시클릭 방향족 라디칼이며, 이 방향족 라디칼은 다른 치환계를 함유할 수 있고; R3은 R2에 주어진 정의중의 하나를 가지거나, 또는 R2및 R3가 합쳐져서 하기 일반식(Ⅲ)의 라디칼
    -Q-Y-Q- (Ⅲ)
    (이때, Q는 2개 결합이 Y기에 대해 오르토 위치에 존재하고 티탄-탄소 결합에 대한 둘재 오르토 위치가 플루오르 원자에 의하여 치환되며 또 Q가 다른 치환체를 함유할 수 있는 카르보시클릭 방향족 라디칼이며, 또 Y는 CH2, 2 내지 12개 탄소원자를 갖는 알킬리덴, 5 내지 7개 고리탄소원자를 갖는 시클로알킬리덴, NR⁴,이고; 또 R4는 상기 티타노센에서 정의한 바와 같다)이고, R2및 R3또는 일반식(Ⅲ)의 라디칼은 하기 일반식(Ⅲ), (IVa) 또는 (IVb)의 라디칼에 의하여 치환되며,
    이때, R5는 수소, 직쇄 또는 측쇄의 C1-C20알킬, C2-C20알켄일, C3-C8시클로알킬, C4-C20시클로알킬알킬 또는 C4-C20알킬시클로알킬,C5-C20알킬시클로알킬알킬, C6-C20시클로알켄일알킬, C6-C14아릴, C7-C20아르알킬 또는 C7-C20알크아릴,C8-C20알크아르알킬 또는 C3-C12트리알킬실릴이고, 이들 라디칼은 비치환되거나 또는 C1-C18알콕시, C1-C18알킬티오, C1-C18알킬술포닐, C6-C10아릴술포닐, C7-C20알크아릴술포닐, 2-테트라히드로푸릴 또는 시아노에 의해 치환되고; R6는 R5에 주어진 정의중의 하나를 갖거나 또는 C1-C20할로게노알킬이거나, -COOH 또는 -COOR6에 의하여 치환된 -CO- 또는 C1-C12알킬을 중간에 포함하는 C2-C20알킬이고, Y1이 -CO-, -CSo- 또는 -SO2-이면 -NR7R8(이때, R7및 R8이 독립해서 R5에 주어진 정의중의 하나를 갖거나 또는 R7및 R8이 합쳐져서 -O-,-S- 또는 N(R9)-를 중간에 포함하는 C3-C7알킬렌이고, R9는 수소, C1-C12알킬, C3-C12알켄일, C7-C12아르알킬 또는 C2-C20알카노일임)이며; 또는 R5및 R6가 합쳐져서 직쇄 또는 측쇄 C2-C8알킬렌이거나, 또는 할로겐, C1-C4알콕시, 아릴옥시 또는 -NR7R8에 의하여 치환된 C2-C8알킬렌이거나 또는
    의 2가 라디칼이며; Y1는 -CO-, -CS-, -COO-, -SO2-- 또는(R4는 상기 정의한 바와 같다)이고; R10은 R에서 주어진 정의중의 하나를 갖거나, 또는 R10및 R이 합쳐져서 C1-C6알킨디일, C2-C6알켄디일, C6-C14아렌디일, C4-C12시클로알칸디일, C5-C12시클로알켄디일, C6-C14시클로알카디엔디일, C7-C20비시클로알칸디일, C7-C20비시클로알켄디일, 또는 -O-,-S- 또는 -N(R9)-에 의하여 치환된 C2-C4알칸디일이며, 이들 라디칼들은 비치환되거나 또는 1개 이상의 할로겐, C1-C10알콕시, C1-C20알킬, C3-C20알켄일 또는 C6-C14아릴의 치환체에 의하여 치환된다.
  2. 제1항에 있어서, R1이 시클로펜타디엔일또는 메틸시클로펜타디엔일인 티타노센.
  3. 제1항에 있어서, R1이 시클로펜타디엔일인 티나노센.
  4. 제1항에 있어서, R2및 R3이 동일한 티나노센.
  5. 제1항에 있어서, R2라디칼이 오르토-위치 모두에서 플루오르에 의하여 치환인 티타노센.
  6. 제1항에 있어서, R2및 R3이 일반식(Ⅳ),(IVa) 또는 (IVb)의 라디칼이 결합된 2,6-디플루오로펜-1-일이고 또 동일하거나 상이한 치환체를 1또는 2개 함유할 수 있는 티타노센.
  7. 제6항에 있어서, 일반식(Ⅰ)에서 R1이 시클로펜타디엔일이고 또 R2및 R3이 하기 일반식(Ⅴ)의 라디칼인 티타노센.
    상기식에서, A는 일반식(Ⅳ),(IVa) 또는 (IVb)의 기임.
  8. 제7항에 있어서, 일반식(Ⅴ)에서 기 A가 F원자에 대한 오르토위치에서 결합된 타타노센.
  9. 제7항에 있어서, A가 일반식(Ⅳ)의 기인 티타노센.
  10. 제1항에 있어서, R5가 수소, 비치환되거나 또는 C1-C12알콕시-또는 테트라히드로푸란-치환된 C1-C12알킬, C2-C5알켄일, C5-C7시클로알킬, C6-C18시클로알킬알킬 또는 -알킬시클로알킬, C7-C18알킬시클로알킬알킬, C7-C16아르알킬 또는 C8-C16알크아르알킬이고, R6은 R5에 주어진 정의중의 하나를 갖거나 또는 C6-C10아릴, C7-C18알크아릴, C1-C12할로게노알킬 또는 -NR7R8(이때 R7및 R8은 서로 독립해서 수소, C1-C12알킬, 페닐, 벤질 또는 시클로헥실이거나 또는 R7및 R8이 합쳐져서 C4-C5알킬렌 또는 3-옥사렌타메틸렌임)이거나, 또는 R5및 R6이 합쳐져서 C2-C8알킬렌이고, 또 Y1은 -CO-,-CS-, -COO- 또는 -SO2-인 일반식(Ⅳ)의 기에 의하여 R2및 R3이 치환된 티타노센.
  11. 제1항에 있어서, R5는 수소, C1-C12알킬, 시클로헥실, 시클로헥실메틸, 2-테트라히드로푸릴메틸, C2-C8알콕시알킬, 알릴 또는 C7-C9아르알킬이고, R6이 C1-C18알킬, C1-C4할로게노알킬, 시클로헥실, C6-C10아릴 또는 -할로게노아릴 또는 C7-C18알크아릴이거나, 또는 R5및 R6이 합쳐져서, C2-C6알킬렌이고 또 Y1는 -CO-, -COO-또는 -SO2-이거나, 또는 -Y1-R(라디칼이 -CO--NHR7, -CS-NHR7, -CO-NR7R8또는 -SO2-NR7R8기(이때, R7은 C1-C12알킬 또는 페닐이고, Rx는 C1-C12알킬이거나, 또는 RO및 R8이 합쳐져서 C4-C5알킬렌 또는 3-옥사펜타메틸렌인 일반식(Ⅳ)의 기에 의하여 R2및 R3이 치환된 티타노센.
  12. 제11항에 있어서, R5는 수소, C1-C8알킬 또는 C7-C9아르알킬이고; R6가 C1-C18알킬, 트리플루오로메틸, 페닐 또는 할로겐- 또는 C1-C12알킬 치환된 페닐이거나, 또는 R5및 R6이 합쳐져서 C2-C6알킬렌이고; 또 Y1이 -CO- 또는 -SO2인 티타노센.
  13. 제1항에 있어서, R(및 R10이 합쳐져서 C2-C8알칸디일, C2-C8알켄디일, C6-C1알켄디일 또는 C7-C12시클로알켄디일이고 또 Y1이 -CO-인 일반식(IVa)의 기에 의하여 R2및 R3이 치환된 타타노센.
  14. 하기 일반식(Ⅳ)의 화합물 1몰을 LiR2또는 LiR3중의 1몰과 반응시킨다음 LiR3또는 LiR2중의 1몰과 반응시키거나, 또는 LiR22몰과 반응시키거나 또는 Li2QYQ 1몰과 반응시킨다음 공지된 방법으로 일반식(Ⅰ)의 화합물을 분리하는 것을 포함하는 제1항에 따른 일반식(Ⅰ)의 티타노센의 제조방법.
    상기식에서, R1,R2,R3및 QYQ는 상기 정의한 바와 같고 또 Z는 할로겐, 특히 염소이다.
  15. (a) 1개 이상의 중합성, 에틸렌성 불포화 이중결합을 함유하는 1개 이상의 비휘발성, 단량체, 올리고머 또는 중합체 화합물 및 (b) 광개시제로서 1개 이상의 일반식(Ⅰ)의 티타노센을 함유하는 조사중합 조성물.
  16. 제15항에 있어서, (b) 이외의 추가로 1개 이상의 광개시제(c)가 존재하는 조성물.
  17. 제16항에 있어서, 광개시제(c)인 벤조페논, 벤조인 알킬에테르, 벤질 케탈, 4-아로일-1,3-디옥솔란, 디알콕시아세토페논,-히드록시- 또는-아미노아세토페논 또는-히드록시클로알킬 페닐 케톤형, 또는 이들의 혼합물을 추가적인 광개시제로 함유하는 조성물.
  18. 도료, 인쇄 잉크, 인쇄판, 내식막 재료 및 기록 재료로서의 제15항에 따른 조성물의 용도.
  19. 적어도 1개 표면상에 제15항에 따른 조성물로 피복된 피복 기재.
  20. 제19항에 따른 피복 기재를 상형성 방향으로 노출시킨다음 비노출 영역을 용매를 사용하여 제거하는 것을 포함하는 안정한 사진상의 제조방법.
  21. 적어도 1개의 중합성, 에틸렌성 불포화 이중 결합을 함유하는 비휘발성의 단량체, 올리고머 또는 중합체 화합물을 광중합 하기 위한 광개시제로서 단독으로 또는 기타 개시제와 함께 사용될 수 있는 제1항에 따른 일반식(Ⅰ)의 티타노센의 용도.
  22. 벤조페논, 벤조인 알킬 에테르, 벤질 케탈, 4-아로일-1,3-디옥솔란, 디알콕시아세토페논, -히드록시아세토페논, -히드록시 시클로알킬 페닐 케톤 또는 -아미노아세토페논형, 또는 이들의 혼합물과 같은 광개시제 및 제1항에 따른 일반식(Ⅰ)의 티타노센을 함유하는 광개시제 혼합물.
  23. 하기 일반식(Ⅶ)의 화합물.
    상기 식에서, Ar은 6-원 카르보시클릭 또는 오르토 위치에서 적어도 1개의 플루오르원자, 수소원자 또는 할로겐 원자를 함유하고 필요에 따라 기타 치환체를 함유하는 5- 또는 6-원 헤테로시클릭 방향족 라디칼이거나, 또는 Ar은 하기 일반식
    (이때, D는 Y에 대한 오르토 위치에 결합된 수소원자 또는 할로겐 원자이고, Q는 D기에 대한 오르토 위치에서 플루오르 원자에 의하여 치환된 카르보시클릭 방향족 라디칼이고 또 Q는 기타 치환체를 함유할 수 있다)의 라디칼이고, 또 Y,Y1,R5및 R6은 제1항에서 정의된 바와 같다.
  24. 제23항에 있어서, 방향족 Ar이 치환된 페닐 고리인 화합물.
  25. 제23항에 있어서, 일반식(Ⅶa)에 상응하는 화합물.
    상기식에서, R5,R6및 Y1은 제 1항에서 정의한 바와 같다.
  26. 제25항에 있어서, -N(R5)-Y1R6기가 플루오르 원자에 대하여 오르토 위치에서 결합된 일반식(Ⅶa)의 화합물.
  27. 하기 일반식(Ⅷ)의 화합물.
    상기식에서 Ar은 23항에 기재된 바와 같고, 또 Y1,R(및 R10은 제1항에 기재된 바와 같다.
  28. 제27항에 있어서, 일반식(Ⅷa)의 화합물.
    상기식에서, Y1,R6및 R10는 제1항에 기재된 바와 같다.
  29. 제28항에 있어서, -N(Y1R10)-Y1R6기가 플루오르 원자에 대한 오르토 위치에서 결합된 일반식(Ⅷa)의 화합물.
  30. 제28항에 있어서, Y1이 -CO-기이고, 또 R6및 R10이 합쳐져서, C2-C8알칸디일,C2-C8알켄디일, C6-C10아렌디일, 또는 C6-C12시클로알칸디일, C6-C12시클로알켄디일, C7-C12비시클로알칸디일 또는 C7-C12-C6-C12시클로알켄디일 C7-C12비시클로알킨디일 또는 비시클로알켄디일인 일반식(Ⅷa)의 화합물.
    ※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019880016123A 1987-12-01 1988-12-01 티타노센, 그의 용도 및 n-치환된 플루오로아닐린 KR0120390B1 (ko)

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US5026625A (en) 1991-06-25
ATE100457T1 (de) 1994-02-15
EP0318893B1 (de) 1994-01-19
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CA1332951C (en) 1994-11-08
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AU2646388A (en) 1989-06-01

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