KR940014480A - Manufacturing method of water-dispersible resin and water-soluble coating composition containing same - Google Patents

Manufacturing method of water-dispersible resin and water-soluble coating composition containing same Download PDF

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KR940014480A
KR940014480A KR1019920027239A KR920027239A KR940014480A KR 940014480 A KR940014480 A KR 940014480A KR 1019920027239 A KR1019920027239 A KR 1019920027239A KR 920027239 A KR920027239 A KR 920027239A KR 940014480 A KR940014480 A KR 940014480A
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water
diisocyanate
resin
active hydrogen
acid
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KR1019920027239A
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Korean (ko)
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KR970001538B1 (en
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곽희성
박종명
김상훈
정철규
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김충세
고려화학 주식회사
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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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)

Abstract

본 발명은 수용성 도료용 수분산 수지의 제조방법 및 이를 바인더로 사용함을 특징으로 하는 수용성 도료 조성물에 관한 것으로, 좀더 구체적으로는 디이소시아네이트 단량체와 활성수소 함유 폴리올 단량체를 이용하여 우레탄 프리포리머를 제조한 후 수분산 단계를 거쳐 제조되는 수용성 도료용 수분산 수지 및 제조된 수분산 수지를 아미노 수지계의 경화제를 사용하여 경화시킴을 특징으로 하는 수분산 수지의 제조방법 및 이를 함유하는 수용성 도료 조성물에 관한 것이다.The present invention relates to a water-soluble coating composition and a method for producing a water-soluble resin for water-soluble paints, characterized in that it is used as a binder, and more specifically, to prepare a urethane prepolymer using a diisocyanate monomer and an active hydrogen-containing polyol monomer The present invention relates to a method for preparing a water-dispersible resin and a water-soluble coating composition containing the same, wherein the water-dispersible resin for water-soluble paint and the prepared water-dispersible resin prepared through the water-dispersion step are cured using an amino resin-based curing agent. .

Description

수분산 수지의 제조 방법 및 이를 함유하는 수용성 도료 조성물Manufacturing method of water-dispersible resin and water-soluble coating composition containing same

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

Claims (13)

(1) 디이소시아네이트 단량체와 활성수소를 함유하는 단량체를 반응시키는 단계 ; (2) 상기 (1)단계에서 제조된 생성물에 형성이 가능하며 활성수소를 함유한 카르복실산과 활성수소 함유 폴리올을 첨가하여 프리폴리머를 형성하는 단계 ; (3) 상기 (2)단계에서 제조된 프리폴리머를 아민으로 중화시킨 후 체인 익스텐더와 반응시키는 단계로 구성됨을 특징으로 하는 수분산 수지의 제조방법.(1) reacting a diisocyanate monomer with a monomer containing active hydrogen; (2) forming a prepolymer by forming a prepolymer by forming a product prepared in step (1) and adding an active hydrogen-containing carboxylic acid and an active hydrogen-containing polyol; (3) neutralizing the prepolymer prepared in step (2) with an amine and then reacting with a chain extender. 제1항에 있어서, 상기 디이소시아네이트 단량체 대 활성수소를 함유하는 단량체가 당량비 15:1~40:1임을 특징으로 하는 수분산 수지의 제조방법.The method of claim 1, wherein the monomer containing diisocyanate monomer to active hydrogen is in an equivalent ratio of 15: 1 to 40: 1. 제1항에 있어서, 상기 디이소시아네이트가 2,2,4- 트리메틸헥사메틸렌 디이소시아네이트(TMDI), 1,4-테트라메틸렌 디이소시아네이트, 1,6-헥사메틸렌 디이소시아네이트(HDI), 이소포론 디이소시아네이트(IPDI), 4,4′-메틸렌-비스(사이크로헥실렌 디이소시아네이트), α,α′-크실렌 디이소시아네이트, 톨루엔 디이소시아네이트, 2,4,6-트리이소시아네이트 톨루엔, 4,4,4-트리이소시아네이트 트리페닐메탄, 1,2,4-벤젠 트리이소시아네이트, 톨루엔 디이소시아네이트, 1,4-페닐렌 디이소시아네이트, 4,4′-데페닐메탄디이소시아네이트 및 메타 또는 파라테트라메틸크실렌 디이소시아네이트로 구성된 군으로부터 선택된 하나 또는 그 이상임을 특징으로 하는 수분산 수지의 제조방법.The method of claim 1, wherein the diisocyanate is 2,2,4-trimethylhexamethylene diisocyanate (TMDI), 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), 4,4'-methylene-bis (cyclohexylene diisocyanate), α, α'-xylene diisocyanate, toluene diisocyanate, 2,4,6-triisocyanate toluene, 4,4,4- Consisting of triisocyanate triphenylmethane, 1,2,4-benzene triisocyanate, toluene diisocyanate, 1,4-phenylene diisocyanate, 4,4′-dephenylmethane diisocyanate and meta or paratetramethylxylene diisocyanate Method for producing a water-dispersible resin, characterized in that one or more selected from the group. 제1항에 있어서, 상기 활성수지를 함유하는 단량체가 데칸올, 도데칸올 또는 언데칸올이며, 상기 디이소시아네이트에 대하여 1~5중량%임을 특징으로 하는 수분산 수지의 제조방법.The method of claim 1, wherein the monomer containing the active resin is decanol, dodecanol or undecanol, and is 1 to 5% by weight based on the diisocyanate. 제1항에 있어서, 상기 활성수소 함유 폴리올이 에틸렌 글라이콜, 프로필렌 글라이콜, 네오펜틸 글라이콜, 부탄 디올, 헥산디올, 폴리카보네이트 디올, 폴리카프로락톤 디올, 1,4-사이크로헥산 디올, 4,4′-디하드록시 사이크로헥실 2,2-프로판, 폴리에틸렌 옥사이드디올, 폴리에틸렌-옥사이드 프로필렌디올, 폴리테트라메틸렌 옥사이드디올로 구성된 군으로부터 선택된 한 또는 그 이상임을 특징으로 하는 수분산 수지의 제조방법.The method of claim 1, wherein the active hydrogen-containing polyol is ethylene glycol, propylene glycol, neopentyl glycol, butane diol, hexanediol, polycarbonate diol, polycaprolactone diol, 1,4-cyclohexane Water dispersion resin, characterized in that one or more selected from the group consisting of diols, 4,4′-dihydroxy cyclohexyl 2,2-propane, polyethylene oxidediol, polyethylene-oxide propylenediol, polytetramethylene oxidediol Manufacturing method. 제1항에 있어서, 상기 염 형성이 가능하며 활성수지를 함유한 카르복실산이 설퍼닉산, 디메틸올 프로피오닉산, 하이드록시에틸 프로피오닉산, 디하이드록시 말레익산, 2,6-디하이드록시벤조익산, 글리콜릭산, 2-하이드록시에탄 설퍼닉산, 1,3-디설퍼닉산 및 2-아미노디페닐아미노 설퍼닉산으로 구성된 군으로부터 선택된 하나이며, 수지 고형분 100을 기준으로 4~15중량%로 사용됨을 특징으로 하는 수분산 수지의 제조방법.According to claim 1, wherein the carboxylic acid capable of salt formation and containing the active resin is sulfonic acid, dimethylol propionic acid, hydroxyethyl propionic acid, dihydroxy maleic acid, 2,6-dihydroxybenzo One selected from the group consisting of Ikic acid, glycolic acid, 2-hydroxyethane sulfonic acid, 1,3-disulfonic acid and 2-aminodiphenylamino sulfonic acid, used at 4 to 15% by weight based on 100 resin solids Method for producing a water-disperse resin, characterized in that. 제1항에 있어서, 상기 염형성이 가능하며, 활성수지를 함유한 산과 상기 활성수소 함유 폴리올이 NCO:OH=1.2:1~5.5:1임을 특징으로 하는 수분산 수지의 제조방법.The method of claim 1, wherein the salt is formed, and the acid containing the active resin and the active hydrogen-containing polyol are NCO: OH = 1.2: 1 to 5.5: 1. 제1항에 있어서, 상기 아민이 디에탄올 아민, 디에틸에탄올 아민, 페닐디에탄올 아민, 메틸 디에탄올 아민, 디메틸 에탄올 아민, 트리에탄올 아민으로 구성된 군으로부터 선택된 하나 또는 그 이상임을 특징으로 하는 수분산 수지의 제조방법.The water-soluble resin according to claim 1, wherein the amine is one or more selected from the group consisting of diethanol amine, diethylethanol amine, phenyl diethanol amine, methyl diethanol amine, dimethyl ethanol amine and triethanol amine. Manufacturing method. 제1항에 있어서, 상기 체인 익서텐더가 디메틸 하이드라진, 1.6-헥사메틸렌 비스하이드라진, 하이드라진 모노하이드라이트, 에틸렌 디아민, 헥사메틸렌 디아민, 이소포론 디아민 및 디아미노페닐메탄으로 구성된 군으로부터 선택된 하나 또는 그 이상이며, 수지 고형분 100을 기준으로 하여 1.0~10중량%로 사용됨을 특징으로 하는 수분산 수지의 제조방법.The method of claim 1, wherein the chain extender is one or more selected from the group consisting of dimethyl hydrazine, 1.6-hexamethylene bishydrazine, hydrazine monohydrite, ethylene diamine, hexamethylene diamine, isophorone diamine and diaminophenylmethane And a method of producing a water-dispersible resin, which is used at 1.0 to 10% by weight based on the resin solid content 100. 제1항에 있어서, 상기 제(2)단계의 염형성이 가능하며 활성수소를 함유한 카르복실산이 수지 고형분 100을 기준으로 하여 4~15중량%의 5-소듐설퍼이소프탈산과 함께 혼합됨을 특징으로 하는 수분산 수지의 제조방법.The method of claim 1, wherein the salt formation of the second step (2) is possible and the carboxylic acid containing active hydrogen is mixed with 4 to 15% by weight of 5-sodiumsulfurisophthalic acid based on the resin solid content 100 The manufacturing method of water dispersion resin made into. 디이소시아네이트 단량체와 활성수소를 함유하는 단량체를 반응시키며, 여기에 염 형성이 가능하며 활성수소를 함유한 카르복실산 단독 또는 5-소듐설퍼이소프탈산 모디파이드 폴리올과의 혼합물을 활성수소 함유 홀리올과 함께 첨가시키고, 아민으로 중화시킨 후 체인 익스텐더와 반응시켜 제조된 수분산 수지.The diisocyanate monomer and the monomer containing the active hydrogen are reacted, and salt formation is possible, and a mixture of the active hydrogen-containing carboxylic acid alone or a mixture of 5-sodiumsulfurisophthalic acid modified polyol with an active hydrogen-containing hollyol A water-dispersible resin prepared by adding together, neutralizing with an amine and then reacting with a chain extender. 디이소시아네이트 단량체와 활성수소를 함유하는 단량체를 반응시키며, 여기에 염 형성이 가능하며 활성수소를 함유한 카르복실산 단독 또는 5-소듐설퍼이소프탈산 모디파이드 폴리올과의 혼합물을 활성수소 함유 폴리올과 함께 첨가시키고, 아민으로 중화시킨 후 체인 익스텐더와 반응시켜 제조된 수분산 수지와 경화제로 구성됨을 특징으로 하는 수용성 도료 조성물.Reacting a diisocyanate monomer with a monomer containing an active hydrogen, which is capable of salt formation, and a mixture of an active hydrogen-containing carboxylic acid alone or a mixture of 5-sodiumsulfurisophthalic acid modified polyol with an active hydrogen-containing polyol A water-soluble coating composition comprising a water-dispersible resin and a hardening agent prepared by addition, neutralization with an amine, and reaction with a chain extender. 제12항에 있어서, 상기 경화제가 헥사메톡시 메틸멜라민, 메톡시 에틸레이티드멜라민, 메톡시 프로필레이티드 멜라민 및 메톡시 부틸레이티드 멜라민으로 구성된 군으로부터 선택된 하나 또는 그 이상이며, 상기 수분산 수지 고형분에 대하여 5~60중량%로 사용됨을 특징으로 하는 수용성 도료 조성물.13. The water dispersible resin according to claim 12, wherein the curing agent is one or more selected from the group consisting of hexamethoxy methyl melamine, methoxy ethylated melamine, methoxy propylated melamine and methoxy butylated melamine. Water-soluble coating composition, characterized in that used in 5 to 60% by weight based on solids. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019920027239A 1992-12-31 1992-12-31 Method for manufacturing water dispersion resin and water-soluble paints composition containing the same KR970001538B1 (en)

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* Cited by examiner, † Cited by third party
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KR100457010B1 (en) * 1995-12-30 2005-04-19 고려화학 주식회사 Compositions of water-dispersed resins for automobile repair and water-soluble paints containing them
KR100672027B1 (en) * 2005-04-19 2007-01-19 (주)디피아이 홀딩스 Method of manufacturing self-emulsified urethane aqueous dispersions and method of manufacturing core-shell emulsion resin composition using the same

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KR101313713B1 (en) * 2011-11-21 2013-10-01 한국신발피혁연구원 compositions of polyurethane resin has anti-hydrolysis property, Manufacturing method of polyurethane resin using the same and polyurethane adhesive with polyurethane resin

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100457010B1 (en) * 1995-12-30 2005-04-19 고려화학 주식회사 Compositions of water-dispersed resins for automobile repair and water-soluble paints containing them
KR100672027B1 (en) * 2005-04-19 2007-01-19 (주)디피아이 홀딩스 Method of manufacturing self-emulsified urethane aqueous dispersions and method of manufacturing core-shell emulsion resin composition using the same

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