KR960014174A - Water-soluble acrylic resin for road sign, manufacturing method thereof and room temperature type road sign paint composition using same - Google Patents

Water-soluble acrylic resin for road sign, manufacturing method thereof and room temperature type road sign paint composition using same Download PDF

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KR960014174A
KR960014174A KR1019940027417A KR19940027417A KR960014174A KR 960014174 A KR960014174 A KR 960014174A KR 1019940027417 A KR1019940027417 A KR 1019940027417A KR 19940027417 A KR19940027417 A KR 19940027417A KR 960014174 A KR960014174 A KR 960014174A
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weight
acrylate
monomer
methacrylate
coating composition
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KR1019940027417A
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KR0150625B1 (en
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이치규
박종희
박태욱
정세화
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김유채
국립공업기술원
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Priority to KR98006256A priority patent/KR0150626B1/en
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Abstract

본 발명은 환경오염이 없고 물성이 개선된 수용성 아크릴산 에스테르계 수지 및 그 제조 방법과 이를 이용한 상온형의 수용성 도로표지용 도료 조성물을 제공함을 목적으로 한다.It is an object of the present invention to provide a water-soluble acrylic acid ester resin having no environmental pollution and improved physical properties, a method for producing the same, and a water-soluble road marking coating composition using the same.

본 발명은 아크릴산 에스테르계 모노머 20∼50wt.%, 방향족 비닐계 모노머 25∼40wt.% 및 카르복시산 비닐 에스테르계의 모노머 25∼40wt.%로 혼합한 산가 40∼60의 혼합 모노머 60∼80중량부, 불포화 카르복시산계 모노머 10∼30중량부, 히드록시알킬기를 가진 불포화 모노머 10∼30중량부, 라디칼 중합 개시 촉매 1∼3중량부, 친수성계 용매 5∼50중량부로 된 부가 중합 반응 혼합물을 사용하여 부가 중합시키는 1차 부가 중합과, 상기 1차 부가 중합물과 상기 혼합 모노머와의 부가 중합에서 중량 평균 분자량을 20,000∼30,000으로 조절하는 2차 부가 중합에 의해 제조되는 수용성 아크릴계 수지 및 그 제조 방법과, 수용성 아크릴계 수지 30∼50중량부, pH 안정제 0.1∼5중량부, 분산제 0.5∼5중량부 및 안료 15∼55중량부로 됨을 특징으로 하는 상온형의 도로표지용 수용성 아크릴계 도료 조성물에 관한 것이다.60 to 80 parts by weight of a mixed monomer having an acid value of 40 to 60 mixed with an acrylic ester monomer 20 to 50 wt.%, An aromatic vinyl monomer 25 to 40 wt.% And a carboxylic acid vinyl ester monomer 25 to 40 wt.%, Addition using the addition polymerization reaction mixture which consists of 10-30 weight part of unsaturated carboxylic-acid monomers, 10-30 weight part of unsaturated monomers having a hydroxyalkyl group, 1-3 weight part of radical polymerization start catalysts, and 5-50 weight part of hydrophilic solvents Water-soluble acrylic resin manufactured by secondary addition polymerization which adjusts a weight average molecular weight to 20,000-30,000 in addition polymerization of the primary addition polymerization to superpose | polymerize, and the said addition addition polymer and the said mixed monomer, and its manufacturing method, and water solubility 30-50 parts by weight of acrylic resin, 0.1-5 parts by weight of pH stabilizer, 0.5-5 parts by weight of dispersant and 15-55 parts by weight of pigment It relates to a krill-based coating composition.

본 발명에 의한 상온형의 수용성 도로표지용 도료 조성물은 내마모성, 내수성, 내약품성, 저장 안정성, 상온에서의 속건성(速乾性) 및 작업성이 우수하고 환경오염의 우려가 없다.The water-soluble road marking coating composition according to the present invention has excellent wear resistance, water resistance, chemical resistance, storage stability, fast drying at room temperature and workability, and there is no fear of environmental pollution.

Description

도로표지용 수용성 아크릴계 수지 및 그 제조방법과 이를 사용한 상온형 도로표지용 도료 조성물Water-soluble acrylic resin for road sign, manufacturing method thereof and room temperature type road sign paint composition using same

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

Claims (29)

아크릴산 에스테르계 모노머 20∼50wt.%, 방향족 비닐계 모노머 25∼40wt.% 및 카르복시산 비닐 에스테르계의 모노머 25∼40wt.%로 혼합한 산가 40∼60의 혼합 모노머 60∼80중량부, 불포화 카르복시산계 모노머 10∼30중량부, 히드록시알킬기를 가진 불포화 모노머 10∼30중량부, 라디칼 중합 개시 촉매 1∼3중량부, 친수성계 용매 5∼50중량부로 된 부가 중합 반응 혼합물을 사용하여 부가 중합시키는 1차 부가 중합과, 상기 1차 부가 중합물과 상기 혼합 모노머와의 부가 중합에서 중량 평균 분자량을 20,000∼30,000으로 조절하는 2차 부가 중합으로 됨을 특징으로 하는 도로 표지용 수용성 아크릴계 수지의 제조 방법.60 to 80 parts by weight of a mixed monomer having an acid value of 40 to 60 mixed with an acrylic acid ester monomer 20 to 50 wt.%, An aromatic vinyl monomer 25 to 40 wt.% And a carboxylic acid vinyl ester monomer 25 to 40 wt.%. 1 to carry out addition polymerization using the addition polymerization reaction mixture which consists of 10-30 weight part of monomers, 10-30 weight part of unsaturated monomers with a hydroxyalkyl group, 1-3 weight part of radical polymerization start catalysts, and 5-50 weight part of hydrophilic solvents. A secondary addition polymerization for controlling a weight average molecular weight to 20,000 to 30,000 in secondary addition polymerization and addition polymerization of the primary addition polymer and the mixed monomer, to produce a water-soluble acrylic resin for road marking. 제1항에 있어서, 아크릴산 에스테르계 모노머가 메틸 아크릴레이트, 에틸 아크릴레이트, 이소프로필 아크릴레이트, 노르말부틸 아크릴레이트, 이소부틸 아크릴레이트, 2－에틸헥실 아크릴레이트, 라우릴 아크릴레이트, 메틸 메타아크릴레이트, 에틸 메타아크릴레이트, 이소프로필 메타아크릴레이트, 노르말부틸 메타아크릴레이트, 이소부틸 메타아크릴레이트, 2－에틸헥실 메타아크릴레이트 및 라우릴 메타아크릴레이트로 된 군으로부터 선택되는 제조 방법.The method of claim 1, wherein the acrylic ester monomer is methyl acrylate, ethyl acrylate, isopropyl acrylate, normal butyl acrylate, isobutyl acrylate, 2-ethylhexyl acrylate, lauryl acrylate, methyl methacrylate. , Ethyl methacrylate, isopropyl methacrylate, normal butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate and lauryl methacrylate. 제1항에 있어서, 방향족 비닐계 모노머가 스티렌, trans－베타－메틸스티렌, 알파－메틸스티렌, 베타－메틸스티렌 및 4－메틸스티렌으로 된 군으로 부터 선택되는 제조 방법.The production process according to claim 1, wherein the aromatic vinyl monomer is selected from the group consisting of styrene, trans-beta-methylstyrene, alpha-methylstyrene, beta-methylstyrene, and 4-methylstyrene. 제1항에 있어서, 카르복시산 비닐 에스테르계 모노머가 비닐 아세테이트, 비닐 프로피오네이트 및 비닐 부티레이트로 된 군으로 부터 선택되는 제조 방법.The process according to claim 1, wherein the carboxylic acid vinyl ester monomer is selected from the group consisting of vinyl acetate, vinyl propionate and vinyl butyrate. 제1항에 있어서, 불포화 카르복시산계 모노머가 아크릴산, 메타크릴산 말레산, 푸마르산 및 이타콘산으로 된 군으로 부터 선택되는 제조 방법.The process according to claim 1, wherein the unsaturated carboxylic acid monomer is selected from the group consisting of acrylic acid, methacrylic acid maleic acid, fumaric acid and itaconic acid. 제1항에 있어서, 히드록시알킬기를 가진 불포화 모노머가 베타－히드록시에틸 아크릴레이트, 베타－히드록시에틸 메타아크릴레이트, 히드록시프로필 아크릴레이트, 히드록시프로필 메타아크릴레이트, 히드록시부틸 아크릴레이트, 히드록시부틸 메타아크릴레이트, 디－(에틸렌글리콜)말레에이트, 디－(에틸렌글리콜)이타코네이트, 부틸렌글리콜 모노아크릴레이트, 부틸렌글리콜 모노메타 아크릴레이트, 2－히드록시에틸 말레에이트, 비스(2－히드록시에틸)말레에이트, 2－히드록시에틸 푸마레이트, 에틸렌글리콜 모노아크릴레이트, 프로필렌글리콜 모노메타아크릴레이트, 프로필렌글리콜 모노아크릴레이트로 된 군으로 부터 선택되는 제조 방법.The unsaturated monomer having a hydroxyalkyl group according to claim 1, wherein the unsaturated monomer having a hydroxyalkyl group is beta-hydroxyethyl acrylate, beta-hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, Hydroxybutyl methacrylate, di- (ethylene glycol) maleate, di- (ethylene glycol) itaconate, butylene glycol monoacrylate, butylene glycol monomethacrylate, 2-hydroxyethyl maleate, bis (2-hydroxyethyl) maleate, 2-hydroxyethyl fumarate, ethylene glycol monoacrylate, propylene glycol monomethacrylate, and propylene glycol monoacrylate. 제1항에 있어서, 라디칼 중합 개시 촉매가 1∼3중량부 첨가되는 제조 방법.The production method according to claim 1, wherein 1 to 3 parts by weight of the radical polymerization initiation catalyst is added. 제1항에 있어서, 친수성계 용매가 알코올류, 에테르류 및 케톤류로 된 군으로 부터 선택되는 한가지 또는 두가지 이상의 혼합 용매인 제조 방법.The process according to claim 1, wherein the hydrophilic solvent is one or two or more mixed solvents selected from the group consisting of alcohols, ethers and ketones. 제8항에 있어서, 알코올류가 에틸 알코올, 메틸 알코올 또는 이소프로필 알코올인 제조 방법.The production method according to claim 8, wherein the alcohols are ethyl alcohol, methyl alcohol or isopropyl alcohol. 제8항에 있어서, 에테르류가 에틸렌 글리콜, 모노메틸 에테르, 디에틸렌 글리콜 모노메틸 에테르, 디에틸렌 글리콜 모노에틸 에테르, 프로필렌 글리콜 모노메틸 에테르 및 디옥사으로 된 군으로 부터 선택되는 제조 방법.The process according to claim 8, wherein the ethers are selected from the group consisting of ethylene glycol, monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether and dioxa. 제8항에 있어서, 케톤류가 아세톤인 제조 방법.The production method according to claim 8, wherein the ketones are acetone. 수용성 아크릴계 수지 30∼50중량부, pH 안정제 0.1∼5중량부, 분산제 0.5∼5중량부 및 체질 안료 15∼55중량부로 됨을 특징으로 하는 상온형의 도로표지용 수용성 아크릴계 도료 조성물.A water-soluble acrylic coating composition for a road sign of a normal temperature type, comprising 30 to 50 parts by weight of a water-soluble acrylic resin, 0.1 to 5 parts by weight of a pH stabilizer, 0.5 to 5 parts by weight of a dispersant, and 15 to 55 parts by weight of an extender pigment. 제12항에 있어서, 체질 안료가 중량비로 이산화티탄(루타일형) : 실리카 분말 : 탈크=2∼4 : 5∼8 : 1∼2의 것인 도료 조성물.The coating composition according to claim 12, wherein the extender pigment is titanium dioxide (rutile type): silica powder: talc = 2-4: 5-8: 1-2 in a weight ratio. 제12항에 있어서, 수용성 아크릴계 수지는 아크릴산 에스테르계 모노머 20∼50wt.%, 방향족 비닐계 모노머 25∼40wt.% 및 카르복시산 비닐 에스테르계 모노머 25∼40wt.%로 혼합한 산가 40∼60의 혼합 모노머 60∼80중량부, 불포화 카르복시산계 모노머 10∼30중량부, 히드록시 알킬기를 가진 불포화 모노머 10∼30중량부, 친수성계 용매 5∼50중량부로 된 부가 중합 반응 혼합물을 사용하여 부가 중합시키는 1차 부가 중합과, 상기 1차 부가 중합물과 상기 혼합 모노머와의 부가 중합에서 분자량을 20,000∼30,000으로 조절하는 2차 부가 중합으로 제조됨을 특징으로 하는 도료 조성물.13. The mixed monomer according to claim 12, wherein the water-soluble acrylic resin is a mixed monomer having an acid value of 40 to 60 mixed with 20 to 50 wt.% Of an acrylic ester monomer, 25 to 40 wt.% Of an aromatic vinyl monomer and 25 to 40 wt. Primary polymerization by addition polymerization using an addition polymerization reaction mixture containing 60 to 80 parts by weight, 10 to 30 parts by weight of unsaturated carboxylic acid monomer, 10 to 30 parts by weight of unsaturated monomer having a hydroxy alkyl group, and 5 to 50 parts by weight of hydrophilic solvent. A coating composition prepared by addition polymerization and secondary addition polymerization in which the molecular weight is adjusted to 20,000 to 30,000 in addition polymerization of the primary addition polymer and the mixed monomer. 제14항에 있어서, 아크릴산 에스테르계 모노머가 메틸 아크릴레이트, 에틸 아크릴레이트, 이소프로필 아크릴레이트, 노르말부틸 아크릴레이트, 이소부틸 아크릴레이트, 2－에틸헥실 아크릴레이트, 라우릴 아크릴레이트, 메틸 메타아크릴레이트, 에틸 메타아크릴레이트, 이소프로필 메타아크릴레이트, 노르말부틸 메타아크릴레이트, 이소부틸 메타아크릴레이트, 2－에틸헥실 메타아크릴레이트 및 라우릴 메타이크릴레이트로 된 군으로 부터 선택되는 도료 조성물.15. The method of claim 14, wherein the acrylic ester monomer is methyl acrylate, ethyl acrylate, isopropyl acrylate, normal butyl acrylate, isobutyl acrylate, 2-ethylhexyl acrylate, lauryl acrylate, methyl methacrylate. , Paint composition selected from the group consisting of ethyl methacrylate, isopropyl methacrylate, normal butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate and lauryl methacrylate. 제14항에 있어서, 방향족 비닐계 모노머가 스티렌, trans－베타－메틸스티렌, 알파－메틸스티렌, 베타－메틸스티렌, 4－메틸스티렌으로 된 군으로 부터 선택되는 도료 조성물.The coating composition according to claim 14, wherein the aromatic vinyl monomer is selected from the group consisting of styrene, trans-beta-methylstyrene, alpha-methylstyrene, beta-methylstyrene, and 4-methylstyrene. 제14항에 있어서, 카르복시산 비닐 에스테르계 모노머가 비닐 아세테이트, 비닐 프로피오네이트 및 비닐 부티레이트로 된 군으로 부터 선택되는 도료 조성물.15. The coating composition of claim 14, wherein the carboxylic acid vinyl ester monomer is selected from the group consisting of vinyl acetate, vinyl propionate and vinyl butyrate. 제14항에 있어서, 불포화 카르복시산계 모노머가 아크릴산, 메타크릴산, 말레산, 푸마르산 및 이타콘산으로 된 군으로 부터 선택되는 도료 조성물.The coating composition according to claim 14, wherein the unsaturated carboxylic acid monomer is selected from the group consisting of acrylic acid, methacrylic acid, maleic acid, fumaric acid and itaconic acid. 제14항에 있어서, 히드록시알킬기를 가진 불포화 모노머가 베타－히드록시에틸 아크릴레이트, 베타－히드록시에틸 메타아크릴레이트, 히드록시프로필 아크릴레이트, 히드록시프로필 메타아크릴레이트, 히드록시부틸 아크릴레이트, 히드록시부틸 메타아크릴레이트, 디－(에틸렌글리콜)말레에이트, 디－(에틸렌글리콜)이타코네이트, 부틸렌글리콜 모노아크릴레이트, 부틸렌글리콜 모노메타 아크릴레이트, 2－히드록시에틸 말레에이트, 비스(2－히드록시에틸)말레에이트, 2－히드록시에틸 푸마레이트, 에틸렌글리콜 모노아크릴레이트, 프로필렌글리콜 모노메타아크릴레이트, 프로필렌글리콜 모노아크릴레이트로 된 군으로 부터 선택되는 도료 조성물.The method of claim 14, wherein the unsaturated monomer having a hydroxyalkyl group is selected from the group consisting of beta-hydroxyethyl acrylate, beta-hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, Hydroxybutyl methacrylate, di- (ethylene glycol) maleate, di- (ethylene glycol) itaconate, butylene glycol monoacrylate, butylene glycol monomethacrylate, 2-hydroxyethyl maleate, bis A coating composition selected from the group consisting of (2-hydroxyethyl) maleate, 2-hydroxyethyl fumarate, ethylene glycol monoacrylate, propylene glycol monomethacrylate, and propylene glycol monoacrylate. 제14항에 있어서, 라디칼 중합 개시 촉매가 1∼3중량부 첨가되는 도료 조성물.The coating composition according to claim 14, wherein 1 to 3 parts by weight of the radical polymerization initiation catalyst is added. 제14항에 있어서, 친수성계 용매가 알코올류, 에테르류 및 케톤류로 된 군으로 부터 선택되는 한가지 또는 두가지 이상의 혼합 용매인 도료 조성물.The coating composition according to claim 14, wherein the hydrophilic solvent is one or two or more mixed solvents selected from the group consisting of alcohols, ethers and ketones. 제14항 또는 제21항에 있어서, 알코올류가 에틸 알코올, 메틸 알코올 또는 이소프로필 알코올인 도료 조성물.The coating composition according to claim 14 or 21, wherein the alcohols are ethyl alcohol, methyl alcohol or isopropyl alcohol. 제14항 또는 제21항에 있어서, 에테르류가 에틸렌 글리콜, 모노메틸 에테르, 디에틸렌 글리콜 모노에틸 에테르, 디에틸렌 글리콜 모노에틸 에테르, 프로필렌 글리콜 모노메틸 에테르 및 디옥산으로 된 군으로 부터 선택되는 도료 조성물.22. The paint according to claim 14 or 21, wherein the ethers are selected from the group consisting of ethylene glycol, monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether and dioxane. Composition. 제14항 또는 제21항에 있어서, 케톤류가 아세톤인 도료 조성물.The coating composition according to claim 14 or 21, wherein the ketones are acetone. 제12항에 있어서, pH 안정제가 암모니아수, 모노에탄올아민, 디에탄올아민, 트리에탄올아민, 1－아미노－2－메틸프로판, 2－아미노－2－메틸프로판, 트리메틸아민, 트리에틸아만 및 N,N－디메틸에탄올아민으로 된 군으로 부터 선택되는 도료 조성물.13. The pH stabilizer according to claim 12, wherein the pH stabilizer is ammonia water, monoethanolamine, diethanolamine, triethanolamine, 1-amino-2-methylpropane, 2-amino-2-methylpropane, trimethylamine, triethylaman and N, N A coating composition selected from the group consisting of dimethylethanolamine. 제12항에 있어서, 분산제가 모노인산 에스테르 분사제, 폴리인산 에스테르 분산제, 폴리우레탄 변성 분산제 및 아크릴레이트 변성 분산제로 된 군으로 부터 선택되는 도료 조성물.13. The coating composition of claim 12 wherein the dispersant is selected from the group consisting of monophosphate ester propellants, polyphosphate ester dispersants, polyurethane modified dispersants and acrylate modified dispersants. 제12항 또는 제26항에 있어서, 모노인산 에스테르 분산제가 트리에틸 포스테이트인 도료 조성물.The coating composition according to claim 12 or 26, wherein the monophosphate ester dispersant is triethyl four state. 제12항 또는 제26항에 있어서, 아크릴레이트 변성 분산제가 암모늄 아크릴레이트인 도료 조성물.The coating composition according to claim 12 or 26, wherein the acrylate modified dispersant is ammonium acrylate. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019940027417A 1994-10-26 1994-10-26 Water-soluble acrylic resin and method for production thereof KR0150625B1 (en)

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KR100716934B1 (en) * 2005-09-30 2007-05-14 주식회사 동진쎄미켐 Acrylate resin for photoresist
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KR100404482B1 (en) * 2000-03-14 2003-11-05 다이니치 세이카 고교 가부시키가이샤 Potentially hydrophilic resins and compositions comprising the same
KR100687601B1 (en) * 2000-12-29 2007-02-27 주식회사 케이씨씨 Acrylic resin composition and its usage
KR100429552B1 (en) * 2000-12-30 2004-04-29 주식회사 디피아이 Method of Preparing Acryl Emulsion Resin
KR101136955B1 (en) * 2011-11-23 2012-04-20 대보하우징 주식회사 Composition for coating road pavement with quick drying characteristic
KR101980672B1 (en) 2018-11-30 2019-05-22 한국도로공사 Paint composition for a road marking enhanced lane recognition for autonomous vehicles
KR102304315B1 (en) 2019-03-07 2021-09-23 주식회사 정석케미칼 Water soluble paint composition for a road marking with improved water-repellent
KR102467674B1 (en) 2022-02-23 2022-11-23 주식회사 세현이엔씨 Manufacturing method of heat-adhesive fixed board for road sign composed of puzzle shape and construction method using the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100298684B1 (en) * 1997-07-12 2001-10-26 한정국 Construction method for functional traffic display on surface
KR100716934B1 (en) * 2005-09-30 2007-05-14 주식회사 동진쎄미켐 Acrylate resin for photoresist
KR102710676B1 (en) 2023-12-01 2024-09-26 주식회사 태웅산업 manufacturing method of water soluble paint compositions for surface sign and construction method of surface sign

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KR0150626B1 (en) 1998-10-01

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