KR960022636A - Method for producing silane-modified reactive oligomer and UV curable coating film composition containing same - Google Patents

Method for producing silane-modified reactive oligomer and UV curable coating film composition containing same Download PDF

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KR960022636A
KR960022636A KR1019940040015A KR19940040015A KR960022636A KR 960022636 A KR960022636 A KR 960022636A KR 1019940040015 A KR1019940040015 A KR 1019940040015A KR 19940040015 A KR19940040015 A KR 19940040015A KR 960022636 A KR960022636 A KR 960022636A
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silane
oligomer
acrylate
modified
reactive
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KR1019940040015A
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Korean (ko)
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KR0163072B1 (en
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김장욱
이병기
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김충세
고려화학 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C263/00—Preparation of derivatives of isocyanic acid
    • C07C263/16—Preparation of derivatives of isocyanic acid by reactions not involving the formation of isocyanate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • 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
    • 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
    • C09D175/06—Polyurethanes from polyesters

Abstract

본 발명은 종이가공용, 염화비닐장판, 플라스틱성형품 및 알루미늄 등에 코팅되어 내열성, 내후성, 상용성, 슬립성 및 내마모성을 향상시키는 실란변성 반응성 올리고머의 제조방법 및 이를 함유하는 도막 조성물에 관한 것으로, 일반식(I)의 자외선 경화형 올리고머는 이소시아네이트 올리고머, 3급실란, 폴리에스테르 폴리올 및 말단에 이중결합과 하이드록시기를 갖는 반응성 모노머를 반응시켜 제조되며, 이를 함유하는 도막 조성물은 상기 자외선 경화형 올리고머에 반응성 올리고머, 아크릴산 에스테르 모노머, 광개시제 및 소량의 첨가제를 교반하면 제조되는 것이다.The present invention relates to a method for preparing a silane-modified reactive oligomer for coating on paper, vinyl chloride sheet, plastic molded article and aluminum to improve heat resistance, weather resistance, compatibility, slip resistance and abrasion resistance, and a coating film composition containing the same. The ultraviolet curable oligomer of (I) is prepared by reacting an isocyanate oligomer, a tertiary silane, a polyester polyol and a reactive monomer having a double bond and a hydroxyl group at the terminal, and the coating film composition containing the reactive oligomer, It is prepared by stirring the acrylic ester monomer, the photoinitiator and a small amount of the additive.

여기서, R1은 수소 또는 메틸기, R2는 (CH2)1, ℓ은 2~6사이의 정수, R3는 지방족, 환상의 지방족, 방향족 화합물 또는 이들 화합물의 올리고머, R4는 탄소수가 1~10인 포화탄화수소 또는 벤질기, Y는 할로겐화 글리콜이나 할로겐화 폴리에스터 폴리올이고, n은 1~20 사이의 정수이다.Wherein R 1 is hydrogen or methyl group, R 2 is (CH 2 ) 1 , l is an integer between 2 and 6, R 3 is aliphatic, cyclic aliphatic, aromatic compound or oligomer of these compounds, R 4 is carbon number 1 Saturated hydrocarbon or benzyl group having ˜10, Y is halogenated glycol or halogenated polyester polyol, n is an integer between 1 and 20.

Description

실란변성 반응성 올리고머의 제조방법 및 이를 함유하는 자외선 경화형 도막 조성물Method for producing silane-modified reactive oligomer and UV curable coating film composition containing same

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

Claims (9)

이소시아네이트 올리고머와, 일반식(2)의 3급실란과, 일반식(4)의 폴리에스테르 폴리올과, 일반식(3)의 말단에 이중결합과 하이드록시기를 갖는 반응성 모노머를 1:0.1:0.1:3:0~1:0.5:2.0:2.5의 몰비로 반응시키되, 올리고머와 3급실란을 촉매 존재하에 하이드로실레이션 시킨 후, 폴리에스테르 폴리올과 반응성 모노머를 부가 반응시켜 제조되는 일반식(I)의 실란변성 반응성 올리고머의 제조방법.An isocyanate oligomer, a tertiary silane of formula (2), a polyester polyol of formula (4), and a reactive monomer having a double bond and a hydroxyl group at the terminal of formula (3) are 1: 0.1: 0.1: Reaction is carried out in a molar ratio of 3: 0 to 1: 0.5: 2.0: 2.5, wherein the oligomer and the tertiary silane are hydrosylated in the presence of a catalyst, followed by addition reaction of the polyester polyol and the reactive monomer. Method for producing a silane-modified reactive oligomer. 여기서, R1은 수소 또는 메틸기, R2는 (CH2)1, ℓ은 2~6사이의 정수, R3는 지방족, 환상의 지방족, 방향족 좌합물 또는 이들 화합물의 올리고머, R4는 탄소수가 1~10인 포화탄화수소 또는 벤질기, Y는 할로겐화 글리콜이나 할로겐화 폴리에스터 폴리올이고, n은 1~20 사이의 정수이다.Where R 1 is hydrogen or a methyl group, R 2 is (CH 2 ) 1 , l is an integer between 2 and 6, R 3 is an aliphatic, cyclic aliphatic, aromatic conjugate or oligomer of these compounds, R 4 is carbon number Saturated hydrocarbon or benzyl group having 1 to 10, Y is halogenated glycol or halogenated polyester polyol, n is an integer between 1 and 20. 여기서, R2는 탄소수가 1~4인 포화탄화수소 또는 벤질기이다.Here, R 2 is a saturated hydrocarbon or benzyl group having 1 to 4 carbon atoms. 여기서, Y는 H 또는 CH3이고, n은 1~10 사이의 정수이다.Wherein Y is H or CH 3 and n is an integer between 1 and 10. 여기서, R은 탄소수가 1~6인 포화탄화수소이다.Here, R is saturated hydrocarbon having 1 to 6 carbon atoms. 제1항에 있어서, 이소시아네이트 올리고머는 이소포론 디이소시아네이트, 4,4-디사이크로헥실메탄 디이소시아레이트, 트리메틸 헥사메틸렌 디이소시아네이트, 1,6-헥사메틸렌 디이소시아네이트, 2,4,4-트리메틸 1,6-헥사메틸렌 디이소시아네이트, 옥타데실렌 디이소시아네이트, 2,6-톨루엔 디이소시아네이트, 헥사메틸렌 디이소시아네이트 올리고머인 바이올렛 또는 이소시아누레이트, 2,4,4-톨루엔 디이소시아네이트로 구성된 그룹으로부터 선택되는 것을 특징으로 하는 실란변성 반응성 올리고머의 제조방법.The isocyanate oligomer of claim 1, wherein the isocyanate oligomer is isophorone diisocyanate, 4,4-dicyclohexylmethane diisocyanate, trimethyl hexamethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,4,4-trimethyl 1 Selected from the group consisting of violet or isocyanurate, 2,4,4-toluene diisocyanate, which is 6-hexamethylene diisocyanate, octadecylene diisocyanate, 2,6-toluene diisocyanate, hexamethylene diisocyanate oligomer Method for producing a silane-modified reactive oligomer, characterized in that. 제1항에 있어서, 이소시아네이트 올리고머는 이소시아네이트기가 2~20개인 것을 특징으로 하는 실란변성 반응성 올리고머의 제조방법.The method for producing a silane-modified reactive oligomer according to claim 1, wherein the isocyanate oligomer has 2 to 20 isocyanate groups. 제1항에 있어서, 3급실란은 벤질디메틸 실란, 3급-부틸디메린 실란, 3-디에틸메틸 실란, 디페닐메틸실란, 1,1,1,3,3,5,5-헵타메틸 트리실록산, 이소부틸디에톡시 실란, 헥실디메톡시 실란, 페닐디메틸 실란, 트리메틸 실란으로 구성된 그룹으로 선택되는 것을 특징으로 하는 실란 변성 반응성 올리고머의 제조방법.The method of claim 1, wherein the tertiary silane is benzyldimethyl silane, tert-butyldimerine silane, 3-diethylmethyl silane, diphenylmethylsilane, 1,1,1,3,3,5,5-heptamethyl Method for producing a silane-modified reactive oligomer, characterized in that selected from the group consisting of trisiloxane, isobutyl diethoxy silane, hexyl dimethoxy silane, phenyl dimethyl silane, trimethyl silane. 제1항에 있어서, 말단에 이중결합과 하이드록실기를 가지고 있는 반응성 모노머는 하이드록시 에틸 아크릴레이트, 하이드록시 에틸 메타 아크릴레이트, 하이드록시 프로필 아크릴레이트, 하이드록시 프로필 메타 아크릴레이트, 하이드록시 부틸 아크릴레이트, 하이드록시 부틸 메타 아크릴레이트로 구성된 그룹으로부터 선택되는 것을 특징으로 하는 실란변성 반응성 올리고머의 제조방법.The reactive monomer of claim 1, wherein the reactive monomer having a double bond and a hydroxyl group at the terminal is hydroxy ethyl acrylate, hydroxy ethyl methacrylate, hydroxy propyl acrylate, hydroxy propyl methacrylate, hydroxy butyl acryl. And hydroxy butyl methacrylate. 제1항에 있어서, 폴리에스테르 폴리올은 하이드록실기가 2개인 글리콜로 에틸콜 글리콜, 디에틸렌 글리콜, 네오펜틸 글리콜, 1,6-헥산디올로 구성된 그룹으로부터 선택되는 것을 특징으로 하는 실란변성 반응성 올리고머의 제조방법.The silane-modified reactive oligomer according to claim 1, wherein the polyester polyol is selected from the group consisting of ethyl glycol glycol, diethylene glycol, neopentyl glycol, and 1,6-hexanediol as glycol having two hydroxyl groups. Manufacturing method. 제1항의 일반식(1)로 표시되는 실란변성 반응성 올리고머와 반응성 올리고머를 5:95:95:5중량부로 조성한 혼합을 8~80중량부와; 반응성 모노머 10~80중량부와; 광개시제 0.1∼10중량부와; 첨가제 소량을 교반시켜 제조되는 실란변성 반응성 올리고머를 함유하는 도막 조성물.8 to 80 parts by weight of a mixture of 5: 95: 95: 5 parts by weight of the silane-modified reactive oligomer and the reactive oligomer represented by the general formula (1) of claim 1; 10 to 80 parts by weight of the reactive monomer; 0.1 to 10 parts by weight of photoinitiator; A coating film composition containing a silane-modified reactive oligomer prepared by stirring a small amount of an additive. 제7항에 있어서, 반응성 올리고머는 산 변성 에폭시 아클릴레이트, 다관능 우레탄 아크릴레이트, 아크릴 변성 우레탄 아크릴레이트, 에폭시 변성 우레탄 아크릴레이트, 우레탄 변성 에폭시 아크릴레이트, 폴리에스테르 아크릴레이트, 폴리에테르 아크릴레이트, 우레탄 아크릴레이트, 에폭시 아크릴레이트로 구성된 그룹으로부터 선택되는 것을 특징으로 하는 실란변성 반응성 올리고머를 함유하는 도막 조성물.8. The reactive oligomer of claim 7, wherein the reactive oligomer is acid modified epoxy acrylate, polyfunctional urethane acrylate, acrylic modified urethane acrylate, epoxy modified urethane acrylate, urethane modified epoxy acrylate, polyester acrylate, polyether acrylate, A coating film composition containing a silane-modified reactive oligomer, which is selected from the group consisting of urethane acrylate and epoxy acrylate. 제7항에 있어서, 반응성 모노머는 1,3-부탄디올 디아크릴레이크, 1,4-부탄디올 디아크릴레이트, 1,6-헥산디올 디아크릴레이트, 디에틸렌 글리콜 디아크릴레이트, 트리에틸렌 글리콜 디메타 아크릴레이트, 네오펜틸 글리콜 디아크릴레이트, 테트라 에틸렌 글리콜 디아크릴레이트, 펜타에리스리톨 트리아크릴레이트, 트리메틸올 프로판 트리아크릴레이트, 네오펜틸 글리콜 디아크릴레이트, 디펜타 에리스리톨 펜타 아크릴레이트, 알콜시레이티 테트라아크릴레이트, 옥틸데실 아크릴레이트, 이소데실 아크릴레이트, 2-페녹시 에틸 아크릴레이트, 라우릴 아크릴레이트, 라우릴 메타 아크릴레이트, 스테아릴 아크릴레이트, 베헤닐 아크릴레이트, 노닐페놀 에톡시레이트 모노 아크릴레이트, 베타-카르복시 에틸 아크릴레이트로 구성된 그룹으로부터 선택되는 아크릴산 에스테르 모노머인 것을 특징으로 하는 실란변성 방응성 올리고머를 함유하는 도막 조성물.The method of claim 7, wherein the reactive monomer is 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, diethylene glycol diacrylate, triethylene glycol dimethacrylic Latex, neopentyl glycol diacrylate, tetra ethylene glycol diacrylate, pentaerythritol triacrylate, trimethylol propane triacrylate, neopentyl glycol diacrylate, dipentaerythritol penta acrylate, alcoholicity tetraacrylate , Octyldecyl acrylate, isodecyl acrylate, 2-phenoxy ethyl acrylate, lauryl acrylate, lauryl methacrylate, stearyl acrylate, behenyl acrylate, nonylphenol ethoxylate mono acrylate, beta -Selected from the group consisting of carboxy ethyl acrylate Coating compositions containing silane-modified room eungseong oligomer characterized in that the methacrylic acid ester monomer. ※ 참고사항:최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019940040015A 1994-12-30 1994-12-30 Paint composition comprising reactive oligomers modified with silane KR0163072B1 (en)

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KR20010058978A (en) * 1999-12-30 2001-07-06 김충세 A cure type coating composition for UV
KR100445728B1 (en) * 2002-01-10 2004-08-25 주식회사 코오롱 Photosensitive Oligomer having Phenoxy Group and Production Method of the Same
KR100482028B1 (en) * 2001-12-28 2005-04-13 주식회사 케이씨씨 Mixture of urethanacrylate oligomer and UV-curable type paint composition
KR100724797B1 (en) * 2005-10-10 2007-06-04 에스에스씨피 주식회사 Low viscosity multi-functional urethaneacrylate oligomer-containing high solid uv curable coating composition

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20010058978A (en) * 1999-12-30 2001-07-06 김충세 A cure type coating composition for UV
KR100482028B1 (en) * 2001-12-28 2005-04-13 주식회사 케이씨씨 Mixture of urethanacrylate oligomer and UV-curable type paint composition
KR100445728B1 (en) * 2002-01-10 2004-08-25 주식회사 코오롱 Photosensitive Oligomer having Phenoxy Group and Production Method of the Same
KR100724797B1 (en) * 2005-10-10 2007-06-04 에스에스씨피 주식회사 Low viscosity multi-functional urethaneacrylate oligomer-containing high solid uv curable coating composition

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