KR960703966A - 규소 화합물 촉진제를 이용한 시클릭 에테르 중합 방법(Cyclic Ether Polymerization Using Silicon Compound Accelerators) - Google Patents

규소 화합물 촉진제를 이용한 시클릭 에테르 중합 방법(Cyclic Ether Polymerization Using Silicon Compound Accelerators)

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KR960703966A
KR960703966A KR1019960700182A KR19960700182A KR960703966A KR 960703966 A KR960703966 A KR 960703966A KR 1019960700182 A KR1019960700182 A KR 1019960700182A KR 19960700182 A KR19960700182 A KR 19960700182A KR 960703966 A KR960703966 A KR 960703966A
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polyether
hydrogen
group
hydrocarbyl
pka
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네빌 에버튼 드리스데일
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미리암 디. 메코너헤이
이.아이. 듀폰 디 네모아 앤드 캄파니
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Publication of KR960703966A publication Critical patent/KR960703966A/ko

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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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/08—Saturated oxiranes
    • C08G65/10—Saturated oxiranes characterised by the catalysts used
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/20—Tetrahydrofuran
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
    • C08G65/2645—Metals or compounds thereof, e.g. salts
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
    • C08G65/2669—Non-metals or compounds thereof
    • C08G65/2681—Silicon or compounds 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
    • C08G65/269—Mixed catalyst systems, i.e. containing more than one reactive component or catalysts formed in-situ

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  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyethers (AREA)
  • Silicon Polymers (AREA)

Abstract

선택된 규소 화합물을 옥시란 및 테트라히드로푸란관 같은 시클릭 에테르 양이온 중합 반응에 첨가시키는 경우, 중합 속도가 상승하고 신규 폴리에테르가 생성되는 종종 있다. 폴리에테르 생성물은, 특히 말단기를 함유하는 규소의 가수 분해 후 단량체 및 마크로단량체로서 유용하다.

Description

규소 화합물 촉진제를 이용한 시클릭 에테르 중합 방법(Cyclic Ether Polymerization Using Silicon Compound Accelerators)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (18)

  1. 양이온계 촉매를 1종 이상의 옥시란, 옥세탄, 테트라히드로푸란, 옥세판, 1,3-디옥솔란 또는 1,3,5-트리옥산과 접촉시켜서 폴리에테르를 제조하는 방법에 있어서, 공액산이 물 중에서 약 16 미만의 pKa를 갖는 것인 기에 결합된 규소를 포함하는 촉진제를 상기 중합 반응계와 접촉시키는 것을 특징으로 하고, 단, 상기 촉진제는 상기 옥시란, 옥세탄, 테트라히드로푸란, 옥세판, 1,3-디옥솔란 또는 1,3,5-트리옥산 없이는 양이온 중합 반응 도중 상기 양이온계 촉매와 거의 반응하지 않고, 또한, 상기 촉진제는 단독으로는 상기 옥시란, 옥세탄, 테트라히드로푸란, 옥세판, 1,3-디옥솔란 또는 1,3,5-트리옥산의 중합을 일으키지 않아 폴리에테르를 생성하지 않는 것인 시클릭 에테르의 양이온 중합 방법.
  2. 제 1항에 있어서, 상기 시클릭 에테르가 하기 일반식의 기로 이루어지는 것인 방법.
    상기 식에서, R1,R2,R3및 R4는 각각 독립적으로 수소이거나 또는 탄소 원자수 1 내지 20의 히드로카르빌이며, n은 0,1,2, 또는 4이다.
  3. 제 2항에 있어서, n은 2이고, R1이 수소이거나 또는 탄소 원자수 1 내지 4의 알킬이며, R2, R3및 R4가 각각 수소인 방법.
  4. 제 1항에 있어서, 상기 pKa가 7 미만인 방법.
  5. 제 1항에 있어서, 상기 규소에 결합된 기가 클로로, 브로모 및 아실옥시로부터 선택되는 것인 방법.
  6. 브뢴스테드 또는 루이스산을 약 -80℃ 내지 약 130℃에서 1종 이상의 옥시란, 옥세탄, 테트라히드로푸란, 옥세판, 1,3-디옥솔란 또는 1,3,5-트리옥산, 및 촉진제와 접촉시키는 것을 포함하고, 상기 촉진제는 공액산 물 중에서 약 16 미만의 pKa를 갖는 것인 제1기가 규소 원자에 결합되어 있는 규소 화합물이며, 단 상기 양이온 중합 반응 도중 상기 양이온계 촉매와 거의 반응하지 않고, 또한, 상기 촉진제는 단독으로는 상기 옥시란, 옥세탄, 테트라히드로푸란, 옥세판, 1,3-디옥솔란 또는 1,3,5-트리옥산의 중합을 일으키지 않아 폴리에테르를 생성하지 않는 것인 폴리에테르의 제조 방법.
  7. 제 6항에 있어서, 상기 시클릭 에테르가 하기 일반식의 기로 이루어지는 것인 방법.
    상기 식에서, R1,R2,R3및 R4는 각각 독립적으로 수소이거나 또는 탄소 원자수 1 내지 20의 히드로카르빌이며, n은 0,1,2, 또는 4이다.
  8. 제 7항에 있어서, n은 2이고, R1이 수소이거나 또는 탄소 원자수 1 내지 4의 알킬이며, R2, R3및 R4가 각각 수소인 방법.
  9. 제 6항에 있어서, 상기 pKa가 7 미만인 방법.
  10. 제 6항에 있어서, 상기 제1기가 클로로, 브로모 및 아실옥시로부터 선택되는 것인 방법.
  11. 제 6항에 있어서, 상기 루이스산이 2가 스트론튬, 바륨, 코발트, 로듐, 이트륨, 팔라듐, 백금, 크롬, 아연, 카드뮴 또는 수은; 3가 스칸듐, 이트륨, 회토류 금속, 비소, 안티몸, 비스무트, 금, 철, 루테늄, 오스뮴, 알루미늄, 갈륨, 인듐 또는 톨륨; 4가 티탄, 지르코늄, 하프늄, 몰리브덴, 규소, 게르마늄, 주석 또는 납; 5가 레늄, 바나듐, 니오븀 또는 탄탈; 및 6가 텅스텐 퍼플루오로알킬술포네이트인 방법.
  12. 제11항에 있어서, 상기 퍼플루오로알킬술포네이트가 이트륨, 회토륨 금속, 미시메탈, 스칸듐, 지르코늄, 탄탈, 아연 및 비스무트를 함유하는 트리플레이트인 방법.
  13. 하기 구조의 폴리에테르.
    Y-{A-[CHR1(CR2R3)n(CHR4)p-O]q-B}m또는 Z-{S-[O-CHR1(CR2R3)n(CHR4)p-O]q-T}f
    상기 식에서, Y는 히드로카르빌 또는 치환된 히드로카르빌기이고; Z는 m개의 자유 결합을 갖는 히드로카르빌, 치환된 히드로카르빌, 실록시 또는 실릴기이며; A는 그의 공액산이 물 주에서 16 미만의 pKa를 갖는 기이고; T는 그의 공액산이 물 중에서 16 미만의 pKa를 갖는 기이며; S는 폴리에테르 부분의 말단 산소 및 Z에 결합된 실릴기이고; B는 포릴에테르 부분의 말단 산소에 결합된 실리기이며; R1,R2,R3및 R4는 각각 독립적으로 수소이거나 또는 탄소 원자수 1 내지 20의 히드로카르빌이고; n은 각각 독립적으로 0,1 또는 2이며; m은 1 내지 5의 정수이고; p는 각각 독립적으로 0 또는 1이며; q는 각각 독립적으로 3 이상의 정수이고; r은 1 이상의 정수이며; 단 p가 0일 또는 n도 0이다.
  14. 제13항에 있어서, n은 2인 폴리에테르.
  15. 제13항에 있어서, R1, R2, R3및 R4가 모두 수소인 폴리에테르.
  16. 제13항에 있어서, n이 0이고, p가 1 또는 0이며, R1이 수소 또는 메틸이고, R4가 수소인 폴리에테르.
  17. 제13항에 있어서, m이 1 또는 2이고, r이 1 또는 2인 폴리에테르.
  18. 제13항에 있어서, r이 5 내지 500이고, q가 5 이상인 폴리에테르.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019960700182A 1993-07-16 1994-07-14 규소 화합물 촉진제를 이용한 시클릭 에테르 중합 방법(Cyclic Ether Polymerization Using Silicon Compound Accelerators) KR960703966A (ko)

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US08/093,242 US5478920A (en) 1993-07-16 1993-07-16 Cyclic ether polymerization using silicon compound accelerators
US08/093,242 1993-07-16
PCT/US1994/007591 WO1995002626A1 (en) 1993-07-16 1994-07-14 Cyclic ether polymerization using silicon compound accelerators

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US (1) US5478920A (ko)
EP (1) EP0708793A1 (ko)
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