KR960037715A - Water dispersible ultraviolet curable polyurethane acrylate, water dispersible ultraviolet curable polyurethane acrylate production method and emulsion production method - Google Patents

Water dispersible ultraviolet curable polyurethane acrylate, water dispersible ultraviolet curable polyurethane acrylate production method and emulsion production method Download PDF

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Publication number
KR960037715A
KR960037715A KR1019950009930A KR19950009930A KR960037715A KR 960037715 A KR960037715 A KR 960037715A KR 1019950009930 A KR1019950009930 A KR 1019950009930A KR 19950009930 A KR19950009930 A KR 19950009930A KR 960037715 A KR960037715 A KR 960037715A
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South Korea
Prior art keywords
acrylate
diisocyanate
curable polyurethane
polyurethane acrylate
mol
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KR1019950009930A
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Korean (ko)
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KR0165930B1 (en
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서경도
김주영
송명언
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서경도
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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
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • 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
    • C08G18/08—Processes
    • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
    • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
    • C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
    • 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
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic

Abstract

1. 청구범위에 기재된 발명이 속하는 기술분야1. TECHNICAL FIELD OF THE INVENTION

본 발명은 도료등으로 사용되는 자외선 경화형 폴리우레탄 아크릴레이트에 관한 것이다.The present invention relates to an ultraviolet curable polyurethane acrylate used in paints and the like.

2. 발명이 해결하려고 하는 기술적 과제2. The technical problem to be solved by the invention

본 발명은 높은 안정성, 우수한 도막강도등을 가지면서 유화제를 사용하지 않고 물에 잘 분산되는 자외선 경화형 폴리우레탄 아크릴레이트를 제조하는데 그 목적을 두고 있다.The present invention aims to produce a UV-curable polyurethane acrylate that has high stability, excellent coating strength, and is well dispersed in water without using an emulsifier.

3. 발명의 해결방법의 요지3. Summary of Solution to Invention

본 발명은 폴리올 1몰과 디이소시아네이트 2몰을 반응시켜 제조된 우레탄화합물 2몰에 대하여 하이드록시 아크릴레이트 1몰 내지 1.8몰을 반응시켜 한쪽 말단에는 2중결합을 갖고, 다른 한쪽 말단에는 NCO기를 갖는 하기 일반식(2)의 화합물을 제조한 다음 NCORL를 갖고 있는 말단에 하기 일반식(3)을 갖는 다가알콜을 반응시켜 일반식(1)로 표시되는 수분산성 자외선 경화형 폴리우레탄아크릴레이트를 제조함으로서 상기의 목적을 달성할 수 있다.The present invention reacts 1 mol to 1.8 mol of hydroxy acrylate with 2 mol of a urethane compound prepared by reacting 1 mol of polyol and 2 mol of diisocyanate to have a double bond at one end and an NCO group at the other end. By preparing a compound of the following formula (2) and then reacting a polyhydric alcohol having the formula (3) to the terminal having NCORL to produce a water-dispersible ultraviolet curable polyurethane acrylate represented by the formula (1) The above object can be achieved.

4. 발명의 중요한 용도4. Important uses of the invention

본 발명의 수분산성 자외선 경화형 폴리우레탄아크릴레이트는 자성체의 바인더, 잉크의 연속상, 미치 비닐타일, 광섬유, 종이, 목재, 금속, 플라스틱등의 코우팅제등으로 사용될 수 있다.The water-dispersible UV-curable polyurethane acrylate of the present invention can be used as a binder of a magnetic material, a continuous phase of ink, coating agent such as Mitch vinyl tile, optical fiber, paper, wood, metal, plastic and the like.

Description

수분산성 자외선 경화성 폴리우레탄 아크릴레이트, 수분산성 자외선 경화형폴리우레탄 아크릴레이트의 제조방법 및 그 에멀젼의 제조방법Water dispersible ultraviolet curable polyurethane acrylate, water dispersible ultraviolet curable polyurethane acrylate production method and emulsion production method

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (5)

하기 일반식(1)로 표시되는 수분산성 자외선 경화형 폴리우레탄 아크릴레이트.Water dispersible ultraviolet-curable polyurethane acrylate represented by following General formula (1). 상기의 일반식(1)에서 R은 하이드록시에틸메타크릴레이트, 하이드록시에틸아크릴레이트, 하이드록시프로필아크릴레이트 중에서 선택된 하이드록시 알킬레이트이고, D는 톨루엔 2,4디이소시아네이트, 디페닐디이소시아네이트, 크실렌디이소시아네이트, 이소포론디이소시아네이트, 헥사메틸렌디이소시아네이트, 테트라메틸크실렌디이소시아네이트, 4,4-디사이클로헥실메탄디이소시아네이트 중에서 선택된 디이소시아네이트이며, P는 폴리프로필렌글리콜, 폴리테트라메틸렌글리콜, 폴리카보네이트, 폴리카프로락톤, 폴리에스터, 에틸렌글리콜, 프로필렌글리콜, 부탄디올, 1,6헥산디올, 글리세롤, 트리메티로프로판, 펜타에리트리톨 중에서 선택된 폴리올이고, n은 10 내지 20의 정수이다.In the general formula (1), R is a hydroxy alkylate selected from hydroxyethyl methacrylate, hydroxyethyl acrylate and hydroxypropyl acrylate, D is toluene 2,4 diisocyanate, diphenyl diisocyanate, Diisocyanate selected from xylene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, tetramethyl xylene diisocyanate, 4,4-dicyclohexyl methane diisocyanate, P is polypropylene glycol, polytetramethylene glycol, polycarbonate, Polycaprolactone, polyester, ethylene glycol, propylene glycol, butanediol, 1,6 hexanediol, glycerol, trimethiropropane, pentaerythritol, and a polyol selected from n. 폴리올 1몰과 디이소시아네이트 2몰을 반응시켜 제조된 우레탄화합물 2몰에 대하여 하이드록시 아크릴레이트 1몰 내지 1.8몰을 반응시켜 한쪽 말단에는 2중결합을 갖고, 다른 한쪽 말단에는 NCO기를 갖는 하기 일반식(2)의 화합물을 제조한 다음 NCO기를 갖고 있는 말단에 하기 일반식(3)을 갖는 다가알콜을 반응시킴을 특징으로 하는 일반식(1)로 표시되는 수분산성 자외선 경화형 폴리우레탄아크릴레이트의 제조방법.1 mol to 1.8 mol of hydroxy acrylate is reacted with 2 mol of a urethane compound prepared by reacting 1 mol of polyol with 2 mol of diisocyanate to have a double bond at one end and an NCO group at the other end. Preparation of the water dispersible UV-curable polyurethane acrylate represented by the general formula (1) characterized by reacting a polyhydric alcohol having the following general formula (3) to the terminal having the NCO group after preparing the compound of (2) Way. 폴리올 1몰과 디이소시아네이트 2몰을 반응시켜 제조된 우레탄화합물 2몰에 대하여 하이드록시 아크릴레이트 1몰 내지 1.8몰을 반응시켜 한쪽 말단에는 2중결합을 갖고, 다른 한쪽 말단에는 NCO기를 갖는 일반식(2)의 화합물을 제조한 다음 NCO기를 갖고 있는 말단에 일반식(3)을 갖는 다가알콜을 반응시켜 일반식(1)의 화합물을 함유하는 것을 특징으로 하는 수분산성 자외선 경화형 폴리우레탄 아크릴레이트 조성물.1 mole to 1.8 moles of hydroxy acrylate is reacted with 2 moles of urethane compound prepared by reacting 1 mole of polyol with 2 moles of diisocyanate to have a double bond at one end and an NCO group at the other end. A water-dispersible UV curable polyurethane acrylate composition comprising the compound of formula (1) by reacting a polyhydric alcohol having the formula (3) at the end having the NCO group after preparing the compound of 2). 폴리올 1몰과 디이소시아네이트 2몰을 반응시켜 제조된 우레탄화합물 2몰에 대하여 하이드록시 아크릴레이트 1몰 내지 1.8몰을 반응시켜 한쪽 말단에는 2중결합을 갖고, 다른 한쪽 말단에는 NCO기를 갖는 일반식(2)의 화합물을 제조한 다음 NCO기를 갖고 있는 말단에 일반식(3)을 갖는 다가알콜을 반응시킨 후 가교제로서 2-에틸헥실아크릴레이트, 1,6헥산디올디아크릴레이트, 트리에틸렌글리콜아크릴레이트를 등량혼합한 아크릴레이트를 제조된 폴리우레탄 아크릴레이트 대 혼합 아크릴레이트의 비율이 5 : 2 이하가 되도록 첨가하고 1-하이드록시 사이클로 헥실 페닐 메탄온을 5중량% 이하로 첨가하고, 열 개시제를 3중량% 이하로 첨가함을 특징으로 하는 수분산성 자외선 경화형 폴리우레탄 아크릴레이트의 제조방법.1 mole to 1.8 moles of hydroxy acrylate is reacted with 2 moles of urethane compound prepared by reacting 1 mole of polyol with 2 moles of diisocyanate to have a double bond at one end and an NCO group at the other end. After preparing the compound of 2), the polyhydric alcohol having the general formula (3) was reacted at the terminal having NCO group, and then 2-ethylhexyl acrylate, 1,6 hexanediol diacrylate and triethylene glycol acrylate as crosslinking agents. Equivalently mixed acrylate was added so that the ratio of the prepared polyurethane acrylate to the mixed acrylate was 5: 2 or less, 1-hydroxy cyclohexyl phenylmethanone was added at 5% by weight or less, and the thermal initiator was 3 Method for producing a water-dispersible UV-curable polyurethane acrylate, characterized in that the addition by weight or less. 폴리올 1몰과 디이소시아네이트 2몰을 반응시켜 제조된 우레탄화합물 2몰에 대하여 하이드록시 아크릴레이트 1몰 내지 1.8몰을 반응시켜 한쪽 말단에는 2중결합을 갖고, 다른 한쪽 말단에는 NCO기를 갖는 일반식(2)의 화합물을 제조한 다음 NCO기를 갖고 있는 말단에 하기 일반식(3)을 갖는 다가알콜을 반응킨 후 가교제로서 2-에틸헥실아크릴레이트, 1,6헥산디올디아클릴레이트, 트리에틸렌글리콜아크릴레이트를 등량혼합한 아클리레이트를 제조된 폴리우레탄 아크릴레이트 대 혼합 아크릴레이트의 비율이 5 : 2 이하가 되도록 첨가하고 1-하이드록시 사이클로 헥실 페닐 메탄온을 5중량% 이하로 첨가하고, 열개시제를 3중량% 이하로 첨가하고, 물에 분산시킴을 특징으로 하는 수분산성 자외선 경화형 폴리우레탄 아크릴레이트 에멀젼의 제조방법.1 mole to 1.8 moles of hydroxy acrylate is reacted with 2 moles of urethane compound prepared by reacting 1 mole of polyol with 2 moles of diisocyanate to have a double bond at one end and an NCO group at the other end. After preparing the compound of 2) and reacting the polyhydric alcohol having the following general formula (3) to the terminal having the NCO group, 2-ethylhexyl acrylate, 1,6 hexanediol diacrylate, triethylene glycol as a crosslinking agent The equivalent acrylate mixed with the acrylate is added so that the ratio of the prepared polyurethane acrylate to the mixed acrylate is 5: 2 or less, and 1-hydroxy cyclohexyl phenylmethanone is added at 5% by weight or less, and heat A method for producing a water dispersible ultraviolet curable polyurethane acrylate emulsion, wherein the initiator is added in an amount of 3% by weight or less and dispersed in water. ※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.※ Note: This is to be disclosed by the original application.
KR1019950009930A 1995-04-26 1995-04-26 Water dispersed polyurethane-acrylate KR0165930B1 (en)

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KR1019950009930A KR0165930B1 (en) 1995-04-26 1995-04-26 Water dispersed polyurethane-acrylate

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100459016B1 (en) * 2001-12-28 2004-12-03 주식회사 금강고려화학 UV-curable type urethane acrylate oligomer and paint composition containing it
KR100563955B1 (en) * 2002-11-16 2006-03-29 부산대학교 산학협력단 Holographic polymer dispersed liquid crystal using polyurethane prepolymer
KR100649432B1 (en) * 2005-02-23 2006-11-27 조광페인트주식회사 Making method of polyurethane dispersion acrylate resins and paints composite
KR101124557B1 (en) * 2009-04-29 2012-03-19 웅진케미칼 주식회사 OLED used flexible display substrate

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20010095368A (en) * 2000-03-23 2001-11-07 서경도 Production of monodisperse micron-sized polymer particles

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100459016B1 (en) * 2001-12-28 2004-12-03 주식회사 금강고려화학 UV-curable type urethane acrylate oligomer and paint composition containing it
KR100563955B1 (en) * 2002-11-16 2006-03-29 부산대학교 산학협력단 Holographic polymer dispersed liquid crystal using polyurethane prepolymer
KR100649432B1 (en) * 2005-02-23 2006-11-27 조광페인트주식회사 Making method of polyurethane dispersion acrylate resins and paints composite
KR101124557B1 (en) * 2009-04-29 2012-03-19 웅진케미칼 주식회사 OLED used flexible display substrate

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