KR950014180A - Heat-resistant poly (urethane-imide) resin and its manufacturing method - Google Patents

Heat-resistant poly (urethane-imide) resin and its manufacturing method Download PDF

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KR950014180A
KR950014180A KR1019930023803A KR930023803A KR950014180A KR 950014180 A KR950014180 A KR 950014180A KR 1019930023803 A KR1019930023803 A KR 1019930023803A KR 930023803 A KR930023803 A KR 930023803A KR 950014180 A KR950014180 A KR 950014180A
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imide
urethane
general formula
represented
block type
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KR1019930023803A
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Korean (ko)
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KR970006896B1 (en
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이영철
김진봉
한상규
정화진
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김영욱
생산기술연구원
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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
    • 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
    • C08G73/1003—Preparatory processes
    • C08G73/1035—Preparatory processes from tetracarboxylic acids or derivatives and diisocyanates

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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)
  • Polyurethanes Or Polyureas (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

본 발명은 폴리(우레탄-이미드)수지 및 그 제조방법에 관한 것으로, 더욱 상세하게는 내열성이 우수한 이미드계 수지의 화학구조를 변화시켜 가공성을 개선함으로써, 내열성 접착제, 내열성 코팅제, 필름, 섬유 또는 복합재료용 수지 등으로 응용하기 위한 블럭형 및 랜덤공중합구조의 폴리(우레탄-이미드)수지 및 그 제조방법에 관한 것이다.The present invention relates to a poly (urethane-imide) resin and a method of manufacturing the same, and more particularly, by changing the chemical structure of an imide-based resin having excellent heat resistance and improving workability, thereby providing a heat resistant adhesive, a heat resistant coating agent, a film, a fiber or The present invention relates to a poly (urethane-imide) resin having a block type and a random copolymer structure for application to a resin for a composite material, and a manufacturing method thereof.

본 발명에서의 우레탄-이미드 수지의 합성방법은 다음과 같은 3가지 방법을 사용하였으며, ① 우레탄 반응후 이미드반응을 시키는 방법 ② 이미드반응후 연속해서 우레탄 반응을 시키는 방법 ③ 우레탄과 이미드를 동시 반응시키는 방법.Synthesis method of the urethane-imide resin in the present invention was used as the following three methods, ① Method for the imide reaction after the urethane reaction ② Method for the urethane reaction continuously after the imide reaction ③ Urethane and imide To react simultaneously.

본 발명에서 사용될 수 있는 디이소시아네이트는 다음 일반식(I)로 나타낼 수 있다.The diisocyanate which can be used in the present invention can be represented by the following general formula (I).

또는이다)or to be)

또한 본 발명에서의 디올로는 일반식 (Ⅲ)으로 표시되는 일반식 (Ⅱ)인 방향족 디올의 에틸렌옥사이드부가 물을In addition, as a diol in this invention, the ethylene oxide part of aromatic diol of general formula (II) represented by General formula (III) is water

HO-R2-OH (Ⅱ)HO-R 2 -OH (II)

단독 사용하거나, 일반식(Ⅱ)의 방향족 디올과 지방족 디올 또는 실리콘 디올을 혼합하여 사용할 수 있으며, 본 발명에서는 이무수물로 다음과 같은 일반식(Ⅳ)의 방향족 유기산이무수물을 사용할 수 있다.It can be used alone or a mixture of aromatic diols of the general formula (II) and aliphatic diols or silicone diol can be used, in the present invention, as the dianhydride, aromatic organic acid dianhydrides of the following general formula (IV) can be used.

이다)to be)

상기 단량체들을 반응시키면서 다음 일반식(Ⅴ)로 나타내어지는 폴리(우레탄-이미드)를 얻을 수 있다.While the monomers are reacted, poly (urethane-imide) represented by the following general formula (V) can be obtained.

(식중, R1은 (Wherein R 1 is

로 표시되는 기들 주에서 1종 또는 2종이 선택되며, P는 -CH2-CH2-O- 기며, m, n은 1∼20의 정수,One or two species are selected from the group represented by the group, P is -CH 2 -CH 2 -O- group, m, n is an integer of 1 to 20,

R2는 R 2 is

로 표시되는 기들 중에서 1종 또는 2종이 선택되며,One or two of the groups represented by is selected,

R3는 R 3 is

로 표시되는 기들 중에서 1종 또는 2종이 선택된다.One or two of the groups represented by is selected.

또한 Z=1∼50의 정수이며, X=0, Y〉〉1이면 이미드블록 타입의 폴리머가 형성되며, X〉〉0, Y=1이면 우레탄블록 타입의 플리머가 형성된다.In addition, an integer of Z = 1 to 50, and if X = 0, Y >> 1, an imide block type polymer is formed, and if X >> 0, Y = 1, a urethane block type polymer is formed.

Description

내열성 폴리(우레탄-이미드)수지 및 그 제조방법Heat-resistant poly (urethane-imide) resin and its manufacturing method

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (4)

다음 일반식(Ⅴ)로 나타내어지는 폴리(우레탄-이미드)수지.Poly (urethane-imide) resin represented by the following general formula (V). ......(Ⅴ)...... (Ⅴ) (식중, R1은 (Wherein R 1 is 로 표시되는 기들 중에서 1종 또는 2종이 선택되며, P는 -CH2-CH2-O-기며, m, n은 1∼20의 정수,One or two of the groups represented by is selected, P is a -CH 2 -CH 2 -O- group, m, n is an integer of 1 to 20, Rz는 Rz is 또는 or 로 표시되는 기들 중에서 1종 또는 2종이 선택되며, One or two of the groups represented by is selected, R3는 R 3 is 로 표시되는 기들 중에서 1종 또는 2종이 선택된다.One or two of the groups represented by is selected. 또한 Z=1∼50의 정수이며, X=0, Y〉〉1이면 이미드블록 타입의 폴리머가 형성되며, X〉〉0, Y=1이면 우레탄블록 타입의 폴리머가 형성된다.In addition, an integer of Z = 1 to 50, wherein an imide block type polymer is formed when X = 0, Y >> 1, and a urethane block type polymer is formed when X >> 0 and Y = 1. 다음 일반식(Ⅰ)로 나타낼 수 있는 과잉의 디이소시아네이트와Excess diisocyanate represented by the following general formula (I) and O C N - R1- N C O ...............(Ⅰ)OCN-R 1 -NCO ............... (Ⅰ) (식중, R1은 (Wherein R 1 is 또는이다)or to be) 일반식(Ⅱ)의 방향족 디올의 에틸렌옥사이드 부가물 단독으로 반응시키거나 지방족 디올 또는 실리콘 디올의 혼합물을 반응시켜 -NCO 말단형우레탄을 제조한후 다음 일반식(Ⅳ)로 표시되는 방향족 유기산 이무수물과 반응시켜 제조되는Ethylene oxide adducts of the aromatic diols of general formula (II) alone or a mixture of aliphatic diols or silicone diols are reacted to produce -NCO-terminated urethanes, and the aromatic organic acid dianhydrides represented by the following general formula (IV) Prepared by reacting with H O - R2- O H ............... (Ⅱ)HO-R 2 -OH ............... (Ⅱ) (식중, Rz은 (Wherein Rz 또는이다)or to be) 이다)to be) 다음 일반식(Ⅴ)의 반복단위를 갖는 블럭형의 내열성 폴리(우레탄-이미드)의 제조방법.Next, a method for producing a block heat-resistant poly (urethane-imide) having a repeating unit of formula (V). ......(Ⅴ)...... (Ⅴ) (식중, R1은 (Wherein R 1 is 로 표시되는 기들 중에서 1종 또는 2종이 선택되며, P는 -CH2-CH2-O- 기며, m, n은 1∼20의 정수,One or two of the groups represented by is selected, P is a -CH 2 -CH 2 -O- group, m, n is an integer of 1 to 20, R2는 R 2 is 또는 or 로 표시되는 기들 중에서 1종 또는 2종이 선택되며, One or two of the groups represented by is selected, R3는 R 3 is 로 표시되는 기들 중에서 1종 또는 2종이 선택된다. 또한 Z=1∼50의 정수이며, X=0, Y〉〉1이면 이미드블록 타입의 폴리머가 형성되며, X〉〉0, Y=1이면 우레탄블록 타입의 폴리머가 형성된다.)One or two of the groups represented by is selected. In addition, an integer of Z = 1 to 50, and if X = 0, Y >> 1, an imide block type polymer is formed, and if X >> 0, Y = 1, a urethane block type polymer is formed.) 다음 일반식(Ⅰ)로 나타낼 수 있는 과잉의 디이소시아네이트와Excess diisocyanate represented by the following general formula (I) and OCN-R1-NCO (Ⅰ)OCN-R 1 -NCO (Ⅰ) (식중, R1은 (Wherein R 1 is 또는이다)or to be) 일반식(Ⅳ)로 나타낼 수 있는 방향족 유기산 이무수물을 반응시켜By reacting the aromatic organic acid dianhydride represented by the general formula (IV) (식중3는 ( 3 is 이다)to be) -NCO 말단형 폴리이미드를 제조한 후 일반식(Ⅲ)으로 표시되는 일반식(Ⅲ)인 방향족 디올의 에티렌옥사이드부가물을 단독Ethylene oxide adducts of the aromatic diols of general formula (III) represented by general formula (III) after preparing -NCO-terminated polyimide HO-R2-OH (Ⅱ)HO-R 2 -OH (II) (식중, R2은 (Wherein R 2 is 또는이다)or to be) (식중, R2은 (Wherein R 2 is 또는이다)or to be) 또는 일반식(Ⅱ)의 방향족 디올과 지방족 디올 또는 실리콘 디올의 혼합물을 반응시켜 제조되는 일반식(Ⅴ)의 반복단위를 갖는 블럭형의 내열성 폴리(우레탄-이미드)의 제조방법.Or a process for producing a block heat-resistant poly (urethane-imide) having a repeating unit of formula (V) prepared by reacting an aromatic diol of formula (II) with a mixture of aliphatic diols or silicone diols. (식중 R3는 (Wherein R 3 is 이다)to be) 다음 일반식(Ⅰ)로 표시되는 디이소시아네이트, 일반식(Ⅳ)로 표시되는 방향족 유기산 이수물과 일반식 (Ⅲ)으로 표시되는 일반식(Ⅱ)인 방향족 디올의 에틸렌옥사이드부가물 단독 또는 일반식(Ⅱ)의 방향족 디올과 지방족 디올 또는 실리콘 디올의 혼합물을 함께 반응시켜 제조하는 일반식(Ⅴ)의 반복단위를 갖는 랜덤형의 내열성 폴리(우레탄-이미드)의 제조방법.Ethylene oxide adducts alone or in general of diisocyanates represented by the following general formula (I), aromatic organic acid dihydrates represented by the general formula (IV) and aromatic diols represented by the general formula (III) A method for producing a random heat-resistant poly (urethane-imide) having a repeating unit of formula (V) prepared by reacting an aromatic diol of (II) with a mixture of an aliphatic diol or a silicone diol together. OCN-R1-NCO (Ⅰ)OCN-R 1 -NCO (Ⅰ) (식중, R1은 (Wherein R 1 is 또는 or HO-R2-OH (Ⅱ)HO-R 2 -OH (II) (식중, R2은 (Wherein R 2 is 또는이다)or to be) (식중, R2은 (Wherein R 2 is 또는이다)or to be) (식중 R3는 (Wherein R 3 is 이다)to be) ......(Ⅴ)...... (Ⅴ) (식중, R1은 (Wherein R 1 is 로 표시되는 기들 중에서 1종 또는 2종이 선택되며, P는 -CH2-CH2-O- 기며, m, n은 1∼20의 정수,One or two of the groups represented by is selected, P is a -CH 2 -CH 2 -O- group, m, n is an integer of 1 to 20, R2는 R 2 is 또는 or 로 표시되는 기들 중에서 1종 또는 2종이 선택되며, One or two of the groups represented by is selected, R3는 R 3 is 로 표시되는 기들 중에서 1종 또는 2종이 선택된다. 또한 Z=1∼50의 정수이며, X=0, Y〉〉1이면 이미드블록 타입의 폴리머가 형성되며, X〉〉0, Y=1이면 우레탄블록 타입의 폴리머가 형성된다.)One or two of the groups represented by is selected. In addition, an integer of Z = 1 to 50, and if X = 0, Y >> 1, an imide block type polymer is formed, and if X >> 0, Y = 1, a urethane block type polymer is formed.) ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019930023803A 1993-11-10 1993-11-10 Heat resistant polyuretane-imide resin adn their manufacturing method KR970006896B1 (en)

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KR100792056B1 (en) * 2004-01-08 2008-01-04 히다치 가세고교 가부시끼가이샤 Polyurethane imido resin, adhesive composition and adhesive composition for connecting circuits
KR101482675B1 (en) * 2014-09-17 2015-01-15 주식회사 구웅산업 Steel pipe with polyurethane-imide resin coating layer

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