KR970042674A - Method for producing self-curing silicone-modified polyester resin and heat-resistant paint containing same - Google Patents

Method for producing self-curing silicone-modified polyester resin and heat-resistant paint containing same Download PDF

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KR970042674A
KR970042674A KR1019950068615A KR19950068615A KR970042674A KR 970042674 A KR970042674 A KR 970042674A KR 1019950068615 A KR1019950068615 A KR 1019950068615A KR 19950068615 A KR19950068615 A KR 19950068615A KR 970042674 A KR970042674 A KR 970042674A
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silicone
polyester resin
modified polyester
heat
weight
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KR1019950068615A
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Korean (ko)
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KR100417087B1 (en
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최광수
김상식
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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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/695—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon
    • C08G63/6954—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon derived from polxycarboxylic acids and polyhydroxy compounds
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91—Polymers modified by chemical after-treatment
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic acids
    • 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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • 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
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • 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
    • C09D5/18—Fireproof paints including high temperature resistant paints
    • 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
    • C09D7/61—Additives non-macromolecular inorganic
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2237—Oxides; Hydroxides of metals of titanium
    • C08K2003/2241—Titanium dioxide
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2296—Oxides; Hydroxides of metals of zinc

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Silicon Polymers (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

본 발명은 열경화성 실리콘 변성수지의 제조 방법 및 이를 함유한 내열 도료조성물에 관한 것으로서 상온에서 저장안정성이 우수하여 저장중 점도의 증가가 거의 없고 150℃ ~ 200℃의 열을 가했을 때 수지 자체로서 가교 반응을 하며 이렇게 경화된 수지 조성물은 내열성이 우수하여 250℃ ~ 400℃ 온도에서도 장기간 견딜수 있어 내열성을 요구하는 접착제에 이용이 가능하고 특히 내열 도료로 사용이 적합하다. 본 발명의 방법은 반응성 수산기를 1분자내에 평균적으로 2개이상을 함유하는 폴리올과 반응성 실란을 또는 알콕시기를 평균 분자당 2개이상을 함유하는 실리콘 중간체를 이용하여 실리콘 변성 수지를 제조하고 이렇게 제조한 실리콘 변성수지와 반응성 알콕시기를 2개 이상 함유하는 실란으로 제조된 가열경화형 실리콘 변성 수지 조성물은 실리콘 수지의 단점인 고온 경화성, 경화물의 취약한 기계적 물성을 보완하여 비교적 저온에서도 쉽게 경화되어 경화물의 우수한 기계적 물성을 갖도록 하고 실리콘의 우수한 내열 특성을 발휘하도록 하는 데 그 특징이 있어 내열도료에 적합하다.The present invention relates to a method for preparing a thermosetting silicone modified resin and a heat-resistant coating composition containing the same, which has excellent storage stability at room temperature and hardly increases in viscosity during storage. The cured resin composition is excellent in heat resistance and can withstand a long period of time at a temperature of 250 ° C. to 400 ° C., so that the resin composition can be used for an adhesive requiring heat resistance, and is particularly suitable for use as a heat resistant paint. The method of the present invention prepares a silicone-modified resin using a polyol containing an average of two or more reactive hydroxyl groups in one molecule and a reactive silane or a silicone intermediate containing two or more alkoxy groups per average molecule. The heat-curable silicone-modified resin composition made of a silane containing two or more silicone-modified resins and reactive alkoxy groups compensates for the high temperature curability and the weak mechanical properties of the cured product, and is easily cured even at a relatively low temperature to provide excellent mechanical properties. It is suitable for heat-resistant paints because it is characterized by having the excellent heat resistance characteristics of silicon.

Description

자체 경화형 실리콘변성 폴리에스테르 수지의 제조 방법 및 이를 함유하는 내열성 도료Method for producing self-curing silicone-modified polyester resin and heat-resistant paint containing same

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

Claims (8)

수 평균 분자량 100~1000, 반응성 수산기 값 100mgKOH/g 이상앤 폴리에스테르 폴리올과 실리콘 중간체를 공중합시켜 실리콘 변성 폴리에스테르 수지를 제조하는 1단계 ; 및 상기 실리콘 변성 폴리에스테르 수지의 수산기 당량에 대해 2개 이상의 알콜시기를 갖는 실란을 0.5~2 단량비로 중합시키는 2단계를 포함하여 이루어진 자체 경화형 실리콘 변성 폴리에스테르 수지의 제조 방법.Step 1 of copolymerizing a polyester polyol and a silicone intermediate with a number average molecular weight of 100 to 1000 and a reactive hydroxyl value of 100 mgKOH / g or more to prepare a silicone-modified polyester resin; And polymerizing a silane having two or more alcohol groups in a 0.5 to 2 monomer ratio with respect to a hydroxyl group equivalent of the silicone-modified polyester resin. 제1항의 1단계에 있어서, 폴리에스테르 폴리올은 2개 이상의 수산기를 갖는 글리콜을 1종 이상 혼합한 것과, 2개 이상의 카르복실산 또는 그의 유도체를 공중합한 것임을 특징으로 하는 자체 경화형 실리콘 변성 폴리에스테르 수지의 제조 방법.The self-curing silicone-modified polyester resin according to claim 1, wherein the polyester polyol is a mixture of one or more glycols having two or more hydroxyl groups and a copolymer of two or more carboxylic acids or derivatives thereof. Method of preparation. 제1항의 1단계에 있어서, 실리콘 변성 폴리에스테르 수지는 실리콘 함량이 20~80 WT%가 되도록 공중합체시켜 제조함을 특징으로 하는 자체 경화형 실리콘 변성 폴리에스테르 수지의 제조 방법.The method of claim 1, wherein the silicone-modified polyester resin is prepared by copolymerizing a silicone content of 20 to 80 WT%. 제1항의 1단계에 있어서, 실리콘 변성 폴리에스테르 수지의 공중합물 100중량부에 대해 25~100중량부의 메틸이소부틸 케론, 메틸이소아밀 케론, 사이클로 헥사논으로 구성된 케론류와 노말부틸 아세테이트, 메틸아밀 아세테이트, 셀로솔부 아세테이트, 2-에틸헥실 아세테이트, 에틸렌글리콜 디아세테이트로 구성된 아세테이트류 중에서 선택된 1종 이상을 용매로 더 첨가하여 공중합시키는 것을 특징으로 하는 자체 경화형 실리콘 변성 폴리에스테르 수지의 제조 방법.The method according to claim 1, wherein 25 to 100 parts by weight of methyl isobutyl keron, methyl isoamyl keron, cyclohexanone, and ketones composed of normal butyl acetate and methyl based on 100 parts by weight of the copolymer of silicone-modified polyester resin A method for producing a self-curing silicone-modified polyester resin, characterized in that copolymerization is further performed by adding at least one selected from the group consisting of amyl acetate, cellosol moiety acetate, 2-ethylhexyl acetate, and ethylene glycol diacetate as a solvent. 제1항의 1단계에 있어서, 실리콘 중간체는 수산기 함량 2~10wt% 또는 알콕시 함량 10~25wt%인 것을 특징으로 하는 자체 경화형 실리콘 변성 폴리에스테르 수지의 제조 방법.The method for producing a self-curing silicone-modified polyester resin according to claim 1, wherein the silicon intermediate has a hydroxyl content of 2 to 10 wt% or an alkoxy content of 10 to 25wt%. 제1항의 2단계에 있어서, 2개 이상의 알콕시기를 갖는 실란은 다음 구조식의 화합물로부터 선택된 것을 특징으로 하는 열경화성 실리콘 변성 폴리에스테르 수지의 제조방법.The method for producing a thermosetting silicone-modified polyester resin according to claim 2, wherein the silane having two or more alkoxy groups is selected from compounds of the following structural formulas. 여기서, R′은 메틸, 에틸, 프로필 또는 페닐이고,Wherein R ′ is methyl, ethyl, propyl or phenyl, R″는 메틸 또는 에틸 이다.R ″ is methyl or ethyl. 제1항의 1,2단계 각각에 있어서, 알콕시 티타네이트를 0.01~1 중량%를 더 첨가하여 중합시키는 것을 특징으로 하는 열경화성 실리콘 변성 폴리에스테르 수지의 제조방법.The method for producing a thermosetting silicone-modified polyester resin according to claim 1, wherein the alkoxy titanate is further added to 0.01 to 1% by weight for polymerization. 제1항에서 제조된 자체 경화형 실리콘 변성 에스테르 수지 30~60 중량%; 이산화 티타늄 15~30 중량%; 징크옥사이드 5~10 중량%; 마그네슘 실리케이트 0~5 중량%; 및 징크옥토에이트 0~1 중량%를 함유하는 내열성 도료 조성물.30 to 60% by weight of the self-curing silicone-modified ester resin prepared in claim 1; 15-30 wt% titanium dioxide; 5-10% by weight of zinc oxide; Magnesium silicate 0-5 wt%; And 0 to 1% by weight of zinc octoate.
KR1019950068615A 1995-12-30 1995-12-30 Method for preparing self curable silicon-modified polyester resin and heat resistant coating comprising the same KR100417087B1 (en)

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KR20180033880A (en) * 2016-09-26 2018-04-04 충북대학교 산학협력단 Method of producing modified silicon resin composite using polyester resin based on naphthalenedicarboxylic acid
KR102225801B1 (en) * 2018-11-30 2021-03-11 주식회사 케이씨씨 Clear coat composition for low temperature curing
KR102242958B1 (en) * 2018-12-31 2021-04-21 주식회사 케이씨씨 Clear coat composition

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KR910011970A (en) * 1989-12-28 1991-08-07 김충세 Manufacturing method of silicone-modified polyester resin for coating and solvent coating composition containing same
JP3022082B2 (en) * 1993-08-10 2000-03-15 信越化学工業株式会社 Method for producing polyester-modified silicone resin
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