KR970706233A - POLYMERIC VEHICLES WHICH INCLUDE A PHENOLIC URETHANE REACTIVE DILUENT, - Google Patents

POLYMERIC VEHICLES WHICH INCLUDE A PHENOLIC URETHANE REACTIVE DILUENT,

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Publication number
KR970706233A
KR970706233A KR1019970702300A KR19970702300A KR970706233A KR 970706233 A KR970706233 A KR 970706233A KR 1019970702300 A KR1019970702300 A KR 1019970702300A KR 19970702300 A KR19970702300 A KR 19970702300A KR 970706233 A KR970706233 A KR 970706233A
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group
aliphatic
carbon atoms
polymer
ester
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KR1019970702300A
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프랭크 엔. 죤스
바이제이 스워럽
라마칸드란 수브라얀
수루 짱
Original Assignee
존 에프. 헌트
엑손 케미컬 페이턴츠 인코포레이팃드
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Priority claimed from US08/621,177 external-priority patent/US5973072A/en
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Publication of KR970706233A publication Critical patent/KR970706233A/en

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    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C07D251/34—Cyanuric or isocyanuric esters
    • 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
    • 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
    • C08G18/3221—Polyhydroxy compounds hydroxylated esters of carboxylic acids other than higher fatty acids
    • 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
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
    • C08G18/3831—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing urethane groups
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
    • C08G18/8067—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds phenolic 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
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C09D201/06—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms

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

Abstract

본 발명은 중합체 비히클, 제형된 코팅 조성물 및 중합체 비히클로부터 제조된 코팅 바인더 및 중합체 비하클이 페놀 우레탄 반응성 희석제를 포함하는 중합체 비히클의 제조방법에 관한 것이다. 페놀 우레탄 반응석 희석제는 적어도 하나의 지방족 하이드록실 그룹을 갖는 페놀 에스테르 알콜로부터 제조될 수 있다.The present invention relates to a polymer vehicle, a coated binder prepared from a formulated coating composition and a polymer vehicle, and a process for preparing a polymer vehicle comprising the polymeric non-charged phenolic urethane reactive diluent. The phenol urethane reactive stone diluent may be prepared from a phenol ester alcohol having at least one aliphatic hydroxyl group.

Description

페놀 우레탄 반응성 희석제를 포함하는 중합체 비히클 (POLYMERIC VEHICLES WHICH INCLUDE A PHENOLIC URETHANE REACTIVE DILUENT)POLYMERIC VEHICLES WHICH INCLUDE A PHENOLIC URETHANE REACTIVE DILUENT,

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is a trivial issue, I did not include the contents of the text.

Claims (35)

분자당 약 1.9 내지 약 20 이소시아네이트 그룹의 평균 이소시아네이트 작용가를 갖는 화합물과 적어도 하나의 지방족 하이드록실 그룹을 갖는 에스테르 알콜의 반응산물인 페놀 우레탄 반응성 희석제를 포함하고, 약 1당량의 이소시아네이트가 페놀 에스테르 알콜의 일부인 지방족 하이드록시 그룹 대략 매당량과 반응하고, 페놀 에스테르 알콜이 페놀 카복실산과 에폭시 작용성 화합물의 반응산물인 중합체 비히클.A phenol urethane reactive diluent which is a reaction product of a compound having an average isocyanate functionality of from about 1.9 to about 20 isocyanate groups per molecule with an ester alcohol having at least one aliphatic hydroxyl group, wherein about 1 equivalent of the isocyanate is present in the phenol ester alcohol Wherein the phenol ester alcohol is a reaction product of a phenolic carboxylic acid and an epoxy functional compound. 제1항에 있어서, 페놀 에스테르 알콜이 적어도 두개의 에스테르 그룹을 갖고 하기의 구조식을 갖는 중합체 비히클.The polymer vehicle according to claim 1, wherein the phenol ester alcohol has at least two ester groups and has the following structural formula. 상기 식에서, R4는 수소, 할로겐, 하이드록실, C1-C8알킬, 및 C1-C8알콕시로 이루어진 그룹 중에서 선택되고, R5는 직접 결합, 탄소와 수소 원자만 갖는 C1-C20유기 라디칼, 구조 안에 페놀, 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물로 이루어진 그룹 중에서 선택된 치환 그룹을 포함하는 C1-C20유기 라디칼로 이루어진 그룹중에서 선택되며, R6는 수소, C1-C20유기 라디칼, 구조 안에 페놀, 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물로 이루어진 그룹 중에서 선택된 치환 그룹을 포함하는 C1-C20유기 라디칼, 직접결합, 및 5 또는 6 탄소원자의 R7부분과 함께 사이클릭환 구조를 형성하는 직접결합으로 이루어진 그룹 중에서 선택되며, R7은 CH2R8[여기에서, R8은 하이드록시, 및 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물로 이루어진 그룹 중에서 선택된 치환 그룹을 포함하는 C1-C20지방족, OR9, OOCR10및 R11로 이루어진 그룹 중에서 선택되고, R9은 탄소수 3 내지 20의 1급 또는 2급 지방족 그룹 또는 지방족 그룹 또는 탄소수 6 내지 20의 방향족 그룹 및 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물을 포함하는 탄소수 3 내지 20의 1급 또는 2급 지방족 그룹으로 이루어진 그룹 중에서 선택되며, R10은 탄소수 4 내지 20의 1급, 2급 또는 3급 지방족 그룹, 탄소수 6 내지 20의 방향족 그룹, 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물을 포함하는 탄소수 4 내지 20의 1급, 2급 또는 3급 지방족 그룹으로 이루어진 그룹 중에서 선택되며, R11은 C1-C20유기 라디칼, 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물을 포함하는 C2-C20유기 라디칼, 및 5 또는 6 탄소원자의 R6부분과 함께 사이클릭환 구조를 형성하는 C2-C20유기 라디칼로 이루어진 그룹 중에서 선택된다)이다.Wherein R 4 is selected from the group consisting of hydrogen, halogen, hydroxyl, C 1 -C 8 alkyl, and C 1 -C 8 alkoxy, and R 5 is selected from the group consisting of a direct bond, a C 1 -C 20 organic radicals, C 1 -C 20 organic radicals comprising substitution groups selected from the group consisting of phenols, aliphatic hydroxyls, esters, ethers, carbonates and combinations thereof in the structure, R 6 is selected from the group consisting of hydrogen, A C 1 -C 20 organic radical, a C 1 -C 20 organic radical comprising a substitution group selected from the group consisting of phenols, aliphatic hydroxyls, esters, ethers, carbonates and combinations thereof in the structure, It is selected from the group consisting of a direct bond to form a cyclic ring structure with the carbon atom R 7 parts, R 7 is CH 2 R 8 [here, R 8 is not in the hydroxyalkyl, and structure Hydroxyl group, is selected from ester, ether, carbonate, and C 1 -C 20 aliphatic, OR 9, the group consisting of OOCR 10 and R 11 containing a substituted group selected from the group consisting of a combination thereof, R 9 is 3 carbon atoms A primary or secondary aliphatic group or aliphatic group of from 20 to 20 carbon atoms or an aromatic group of from 6 to 20 carbon atoms and a linear or branched primary or secondary alkyl group of 3 to 20 carbon atoms containing an aliphatic hydroxyl, ester, ether, carbonate, And R 10 is selected from the group consisting of a primary, secondary or tertiary aliphatic group having 4 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, an aliphatic hydroxyl group, an ester, an ether, a carbonate, of 4 to 20 carbon atoms comprising a combination of primary, is selected from the group consisting of secondary or tertiary aliphatic group, R 11 is C 1 -C 20 - C 2 to form a cyclic ring structure together with the organic radical, aliphatic hydroxyl, ester, ether, carbonate, and C 2 -C 20 organic radical, and 5 or 6 carbon atoms R 6, a portion including the combination thereof in the structure C 20 is is selected from the group consisting of an organic radical). 화학식(1)의 페놀 우레탄 화합물을 포함하는 중합체 비히클.A polymer vehicle comprising a phenol urethane compound of formula (1). 상기 식에서, N은 약 1 내지 약 4이고, R12는 알킬, 알킬 이작용성 라디칼, 알케닐, 알케닐 이작용성 라디칼, 방향족 및 방향족 이작용성 라디칼로 이루어진 그룹 중에서 선택된다.Where N is from about 1 to about 4 and R 12 is selected from the group consisting of alkyl, alkyl-bifunctional radicals, alkenyl, alkenyl bifunctional radicals, aromatic and aromatic bifunctional radicals. 제3항에 있어서, R12가4. The compound according to claim 3, wherein R < 12 > 로 이루어진 그룹 중에서 선택되고 n이 1 이상인 중합체 비히클.≪ / RTI > wherein n is 1 or greater. 제4항에 있어서, 페놀 우레탄 반응성 희석제가 화학식(2)을 갖는 중합체 비히클.5. The polymer vehicle of claim 4, wherein the phenol urethane reactive diluent has formula (2). 제4항에 있어서, 페놀 우레탄 반응성 희석제가 화학식(3)을 갖는 중합체 비히클.5. A polymer vehicle according to claim 4, wherein the phenol urethane reactive diluent has the formula (3). 제4,5 또는 6항에 있어서, 중합체 비히클이 분자당 약 1.9 내지 약 20 이소시아네이트 그룹의 이소시아네이트 작용가를 갖는 화합물을 추가로 포함하는 중합체 비히클.The polymer vehicle of any of claims 4, 5 or 6, wherein the polymeric vehicle further comprises a compound having an isocyanate functionality of from about 1.9 to about 20 isocyanate groups per molecule. 분자당 약 3 내지 약 30 가교결합 그룹의 평균 가교결합 작용가를 갖는 다작용성 아미노 수지, 분자당 약 1,9 내지 약 20 이소시아네이트 그룹의 평균 이소시아네이트 작용가를 갖는 화합물 및 다작용성 아미노 수지와 다작용성 이소시아네이트 화합물의 혼합물로 이루어진 그룹 중에서 선택된 가교결합제; 및 분자당 약 1.9 내지 약 20 이소시아네이트 그룹의 평균 이소시아네이트 작용가를 갖는 화합물과 적어도 하나의 지방족 하이드록실 그룹을 갖는 페놀 에스테르 알콜의 반응산물인 페놀 우레탄 반응성 희석제를 포함하고, 약 1당량의 이소시아네이트가 페놀 에스테르 알콜의 일부인 지방족 하이드록실 그룹 대략 매당량과 반응하고, 페놀 에스테르 알콜이 페놀 카복실산과 에폭시 작용성 화합물의 반응산물인 중합체 비히클.A multifunctional amino resin having an average cross-linking functionality of from about 3 to about 30 cross-linking groups per molecule, a compound having an average isocyanate functionality of from about 1.9 to about 20 isocyanate groups per molecule, and a multifunctional amino resin and a multifunctional isocyanate compound A cross-linking agent selected from the group consisting of And a phenol urethane reactive diluent which is the reaction product of a compound having an average isocyanate functionality of from about 1.9 to about 20 isocyanate groups per molecule with a phenol ester alcohol having at least one aliphatic hydroxyl group, wherein about 1 equivalent of the isocyanate is a phenol ester Wherein the phenol ester alcohol is reacted with approximately every equivalent amount of an aliphatic hydroxyl group that is part of an alcohol and wherein the phenol ester alcohol is the reaction product of a phenolic carboxylic acid and an epoxy functional compound. 제8항에 있어서, 가교결합제와 반응성 희석제가 중합체 비히클을 포함하는 제형된 코팅 조성물중의 VOC를 제형된 코팅 조성물 갤론 당 약 3파운드 이하의 VOC로 감소시키기에 유효한 양으로 각각 및, 경화된 중합체 비히클로부터 제조된 코팅 바인더에 적어도 약 HB의 펜슬 경도 및 적어도 약 20인치 파운드 다이렉트 및 적어도 약 20인치 파운드 인다이렉트의 내충격성을 제공하기에 유효한 양으로 각각 존재하는 중합체 비히클.9. The composition of claim 8, wherein the crosslinking agent and the reactive diluent are each in an amount effective to reduce VOC in the formulated coating composition comprising a polymer vehicle to less than about 3 pounds VOC per gallon of the coated composition, The polymeric vehicle being each present in an amount effective to provide a coating binder made from the vehicle at least about a pencil hardness of about HB and at least about 20 inches pounds direct and at least about 20 inches pounds of direct impact resistance. 제8항 또는 제9항에 있어서, 페놀 에스테르 알콜이 화학식(A)를 갖는 중합체 비히클.The polymer vehicle according to claim 8 or 9, wherein the phenol ester alcohol has the formula (A). 상기 식에서, R4는 수소, 할로겐, 하이드록실, C1-C8알킬, 및 C1-C8알콕시로 이루어진 그룹 중에서 선택되고, R5는 직접 결합, 탄소와 수소 원자만 갖는 C1-C20유기 라디칼, 구조 안에 페놀, 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물로 이루어진 그룹 중에서 선택된 치환 그룹을 포함하는 C1-C20유기 라디칼로 이루어진 그룹 중에서 선택되며, R6는 수소, C1-C20유기 라디칼, 구조 안에 페놀, 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물로 이루어진 그룹 중에서 선택된 치환 그룹을 포함하는 C1-C20유기 라디칼, 직접결합, 및 5 또는 6 탄소원자와 R7부분과 함께 사이클릭환 구조를 형성하는 직접결합으로 이루어진 그룹 중에서 선택되며, R7은 CH2R8[여기에서, R5는 하이드록실, 및 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물로 이루어진 그룹 중에서 선택된 치환 그룹을 포함하는 C1-C20지방족, OR9, OOCR10및 R11로 이루어진 그룹 중에서 선택되고, R9은 탄소수 3 내지 20의 1급 또는 2급 지방족 그룹 또는 탄소수 6 내지 20의 방향족 그룹 및 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물을 포함하는 탄소수 3 내지 20의 1급 또는 2급 지방족 그룹으로 이루어진 그룹 중에서 선택되며, R10은 탄소수 4 내지 20의 1급, 2급 또는 3급 지방족 그룹, 탄소수 6 내지 20의 방향족 그룹, 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물을 포함하는 탄소수 4 내지 20의 1급, 2급 또는 3급 지방족 그룹으로 이루어진 그룹 중에서 선택되며 R11은 C2-C20유기 라디칼, 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물을 포함하는 C2-C20유기 라디칼, 및 5 또는 6 탄소원자와 R6부분과 함께 사이클릭환 구조를 형성하는 C2-C20유기 라디칼로 이루어진 그룹 중에서 선택된다] 이다.Wherein R 4 is selected from the group consisting of hydrogen, halogen, hydroxyl, C 1 -C 8 alkyl, and C 1 -C 8 alkoxy, and R 5 is selected from the group consisting of a direct bond, a C 1 -C 20 organic radicals, C 1 -C 20 organic radicals comprising substitution groups selected from the group consisting of phenols, aliphatic hydroxyls, esters, ethers, carbonates and combinations thereof in the structure, R 6 is selected from the group consisting of hydrogen, A C 1 -C 20 organic radical, a C 1 -C 20 organic radical comprising a substitution group selected from the group consisting of phenols, aliphatic hydroxyls, esters, ethers, carbonates and combinations thereof in the structure, is selected from the group consisting of a direct bond to form a cyclic ring structure with the carbon atom and R 7 parts, R 7 is CH 2 R 8 [here, R 5 is not in hydroxyl, and structure Hydroxyl group, is selected from ester, ether, carbonate, and C 1 -C 20 aliphatic, OR 9, the group consisting of OOCR 10 and R 11 containing a substituted group selected from the group consisting of a combination thereof, R 9 is 3 carbon atoms To 20 primary or secondary aliphatic groups or aromatic groups of 6 to 20 carbon atoms and primary or secondary aliphatic groups of 3 to 20 carbon atoms containing aliphatic hydroxyl, ester, ether, carbonate and combinations thereof in the structure R 10 is selected from the group consisting of a primary, secondary or tertiary aliphatic group having 4 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, an aliphatic hydroxyl, an ester, an ether, a carbonate and combinations thereof in the structure A primary, secondary or tertiary aliphatic group having 4 to 20 carbon atoms and R 11 is selected from the group consisting of C 2 -C 20 organic radicals, In the aliphatic hydroxyl, ester, ether, carbonate, and combinations of C 2 -C 20 organic radical comprising a formulation, and 5 or 6 to form a cyclic ring structure with the carbon atom and R 6 part C 2 -C 20 organic ≪ / RTI > 제8항 또는 9항에 있어서, 페놀 에스테르 알콜이 약 110 내지 약 1000 범위의 분자량을 갖고 말단 글리시딜 그룹을 갖는 모노글리시딜 화합물과 하이드록시벤조산의 반응산물인 중합체 비히클.9. The polymer vehicle according to claim 8 or 9, wherein the phenol ester alcohol is a reaction product of a monoglycidyl compound having a molecular weight ranging from about 110 to about 1000 and having a terminal glycidyl group with hydroxybenzoic acid. 제10항에 있어서, 하이드록시벤조산이 파라하이드록시벤조산이고 모노글리시딜 화합물이 화학식(B)를 갖는 중합체 비히클.The polymer vehicle according to claim 10, wherein the hydroxybenzoic acid is parahydroxybenzoic acid and the monoglycidyl compound has the formula (B). 상기 식에서, R은 지방족 그룹의 혼합물이고, 3개의 R 그룹은 총 8개의 탄소원자를 갖는다.Wherein R is a mixture of aliphatic groups and the three R groups have a total of eight carbon atoms. 분자당 약 1.9 내지 약 20 이소시아네이트 그룹의 이소시아네이트 작용가를 갖는 화합물과 적어도 하나의 지방족 하이드록실 그룹을 갖는 페놀 에스테르 알콜의 반응산물이고 약 1당량의 이소시아네이트가 페놀 에스테르 알콜의 일부인 지방족 하이드록실 그룹 대략 매당량과 반응하고, 페놀 에스테르 알콜이 페놀 카복실산과 에폭시 작용성 화합물의 반응산물인 페놀 우레탄 화합물.A reaction product of a compound having an isocyanate functionality of from about 1.9 to about 20 isocyanate groups per molecule with a phenol ester alcohol having at least one aliphatic hydroxyl group and about 1 equivalent of isocyanate being an aliphatic hydroxyl group that is part of the phenol ester alcohol, And the phenol ester alcohol is the reaction product of a phenolic carboxylic acid and an epoxy functional compound. 제13항에 있어서, 이소시아네이트 화합물이 이소시아네이트, 뷰렛, 이소시아누레이트 및 이들의 혼합물로 이루어진 그룹 중에서 선택되는 페놀 우레탄 화합물.14. The phenol urethane compound of claim 13, wherein the isocyanate compound is selected from the group consisting of isocyanates, buretets, isocyanurates, and mixtures thereof. 제13항 또는 14항에 있어서, 페놀 에스테르 알콜이 화학식(A)을 갖는 페놀 우레탄 화합물.14. The phenol urethane compound according to claim 13 or 14, wherein the phenol ester alcohol has the formula (A). 상기 식에서, R4는 수소, 할로겐, 하이드록실, C1-C8알킬, 및 C1-C8알콕시로 이루어진 그룹 중에서 선택되고, R5는 직접 결합, 탄소와 수소 원자만 갖는 C1-C20유기 라디칼, 구조 안에 페놀, 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물로 이루어진 그룹 중에서 선택된 치환 그룹을 포함하는 C1-C20유기 라디칼로 이루어진 그룹 중에서 선택되며, R6는 수소, C1-C20유기 라디칼, 구조 안에 페놀, 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물로 이루어진 그룹 중에서 선택된 치환체 그룹을 포함하는 C1-C20유기 라디칼, 직접결합, 및 5 또는 6 탄소원자와 R7부분과 함께 사이클릭환 구조를 형성하는 직접결합으로 이루어진 그룹 중에서 선택되며, R7은 CH2R8[여기에서, R8은 하이드록시, 및 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물로 이루어진 그룹 중에서 선택된 치환 그룹을 포함하는 C1-C20지방족, OR9, OOCR10및 R11로 이루어진 그룹 중에서 선택되고, R9은 탄소수 3 내지 20의 1급 또는 2급 지방족 그룹 또는 탄소수 6 내지 20의 방향족 그룹 및 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물을 포함하는 탄소수 3 내지 20의 1급 또는 2급 지방족 그룹으로 이루어진 그룹 중에서 선택되며, R10은 탄소수 4 내지 20의 1급, 2급 또는 3급 지방족 그룹, 탄소수 6 내지 20의 방향족 그룹, 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물을 포함하는 탄소수 4 내지 20의 1급, 2급 또는 3급 지방족 그룹으로 이루어진 그룹 중에서 선택되며 R11은 C2-C20유기 라디칼, 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물을 포함하는 C2-C20유기 라디칼, 및 5 또는 6 탄소원자와 R6부분과 함께 사이클릭환 구조를 형성하는 C2-C20유기 라디칼로 이루어진 그룹 중에서 선택된다] 이다.Wherein R 4 is selected from the group consisting of hydrogen, halogen, hydroxyl, C 1 -C 8 alkyl, and C 1 -C 8 alkoxy, and R 5 is selected from the group consisting of a direct bond, a C 1 -C 20 organic radicals, C 1 -C 20 organic radicals comprising substitution groups selected from the group consisting of phenols, aliphatic hydroxyls, esters, ethers, carbonates and combinations thereof in the structure, R 6 is selected from the group consisting of hydrogen, A C 1 -C 20 organic radical, a C 1 -C 20 organic radical comprising a substituent group selected from the group consisting of phenols, aliphatic hydroxyls, esters, ethers, carbonates and combinations thereof in the structure, is selected from the group consisting of a direct bond to form a cyclic ring structure with the carbon atom and R 7 parts, in R 7 is CH 2 R 8 [here, R 8 is hydroxy, and structure Bangjok hydroxyl, is selected from ester, ether, carbonate, and C 1 -C 20 aliphatic, OR 9, the group consisting of OOCR 10 and R 11 containing a substituted group selected from the group consisting of a combination thereof, R 9 is 3 carbon atoms To 20 primary or secondary aliphatic groups or aromatic groups of 6 to 20 carbon atoms and primary or secondary aliphatic groups of 3 to 20 carbon atoms containing aliphatic hydroxyl, ester, ether, carbonate and combinations thereof in the structure R 10 is selected from the group consisting of a primary, secondary or tertiary aliphatic group having 4 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, an aliphatic hydroxyl, an ester, an ether, a carbonate and combinations thereof in the structure A primary, secondary or tertiary aliphatic group having 4 to 20 carbon atoms and R 11 is selected from the group consisting of C 2 -C 20 organic radicals, Joan aliphatic hydroxyl, ester, ether, carbonate, and C 2 -C 20 which forms a cyclic ring structure thereof containing formulation C 2 -C 20 organic radical, and 5 or 6 carbon atoms and R 6 together with the part Organic radicals. 제15항에 있어서, 하이드록시벤조산이 파라하이드록시벤조산이고 모노글리시딜 화합물이 화학식(B)을 갖는 페놀 우레탄 화합물.16. The phenol urethane compound according to claim 15, wherein the hydroxybenzoic acid is parahydroxybenzoic acid and the monoglycidyl compound has the formula (B). 상기 식에서, R은 지방족 그룹의 혼합물이고, 3개의 R 그룹은 총 8개의 탄소원자를 갖는다.Wherein R is a mixture of aliphatic groups and the three R groups have a total of eight carbon atoms. 화학식(1)의 페놀 우레탄 반응성 희석제; 분자당 약 1.9 내지 약 20 하이드록실의 평균 하이드록실 작용가 및 적어도 200의 분자량을 갖는 적어도 하나의 폴리올; 및 분자당 약 1.9 내지 약 20 이소시아네이트 그룹의 평균 이소시아네이트 작용가를 갖는 화합물, 분자당 약 3 내지 약 30 가교결합 그룹을 갖는 아미노 수지 및 이소시아네이트 화합물과 아미노 수지의 혼합물로 이루어진 그룹 중에서 선택된 적어도 하나의 가교결합제를 포함하는 중합체 비히클.A phenol urethane reactive diluent of formula (1); At least one polyol having an average hydroxyl functionality of from about 1.9 to about 20 hydroxyls per molecule and a molecular weight of at least 200; And at least one crosslinking agent selected from the group consisting of compounds having an average isocyanate functionality of from about 1.9 to about 20 isocyanate groups per molecule, amino resins having from about 3 to about 30 crosslinking groups per molecule, and mixtures of isocyanate compounds and amino resins ≪ / RTI > 상기 식에서, R4는 수소, 할로겐, 하이드록실, C1-C8알킬, 및 C1-C8알콕시로 이루어진 그룹 중에서 선택되고, R5는 직접 결합, 탄소와 수소 원자만 갖는 C1-C20유기 라디칼, 구조 안에 페놀, 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물로 이루어진 그룹 중에서 선택된 치환 그룹을 포함하는 C1-C20유기 라디칼로 이루어진 그룹 중에서 선택되며, R6는 수소, C1-C20유기 라디칼, 구조 안에 페놀, 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물로 이루어진 그룹 중에서 선택된 치환제 그룹을 포함하는 C1-C20유기 라디칼, 직접결합, 및 5 또는 6 탄소원자와 R7부분과 함께 사이클릭환 구조를 형성하는 직접결합으로 이루어진 그룹 중에서 선택되며, R7은 CH2R8[여기에서, R8은 하이드록시, 및 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물로 이루어진 그룹 중에서 선택된 치환 그룹을 포함하는 C1-C20지방족, OR9, OOCR10및 R11로 이루어진 그룹 중에서 선택되고, R9은 탄소수 3 내지 20의 1급 또는 2급 지방족 그룹 또는 탄소수 6 내지 20의 방향족 그룹 및 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물을 포함하는 탄소수 3 내지 20의 1급 또는 2급 지방족 그룹으로 이루어진 그룹 중에서 선택되며, R10은 탄소수 4 내지 20의 1급, 2급 또는 3급 지방족 그룹, 탄소수 6 내지 20의 방향족 그룹, 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물을 포함하는 탄소수 4 내지 20의 1급, 2급 또는 3급 지방족 그룹으로 이루어진 그룹 중에서 선택되며 R11은 C2-C20유기 라디칼, 구조안에 지방족 하이드록실, 에스테르, 에테르, 카보네이트 및 이들의 배합물을 포함하는 C2-C20유기 라디칼, 및 5 또는 6 탄소원자와 R6부분과 함께 사이클릭환 구조를 형성하는 C2-C20유기 라디칼로 이루어진 그룹 중에서 선택된다] 이며, N은 약 1 내지 약 4이며, R12는 알킬, 알킬 이작용성 라디칼, 알케닐, 알케닐 이작용성 라디칼, 방향족 및 방향족 이작용성 라디칼로 이루어진 그룹 중에서 선택된다.Wherein R 4 is selected from the group consisting of hydrogen, halogen, hydroxyl, C 1 -C 8 alkyl, and C 1 -C 8 alkoxy, and R 5 is selected from the group consisting of a direct bond, a C 1 -C 20 organic radicals, C 1 -C 20 organic radicals comprising substitution groups selected from the group consisting of phenols, aliphatic hydroxyls, esters, ethers, carbonates and combinations thereof in the structure, R 6 is selected from the group consisting of hydrogen, A C 1 -C 20 organic radical, a C 1 -C 20 organic radical comprising a substituent group selected from the group consisting of phenols, aliphatic hydroxyls, esters, ethers, carbonates and combinations thereof in the structure, 6 is selected from the group consisting of a direct bond to form a cyclic ring structure with the carbon atom and R 7 parts, R 7 is in the CH 2 R 8 [here, R 8 is hydroxy, and structure Bangjok hydroxyl, is selected from ester, ether, carbonate, and C 1 -C 20 aliphatic, OR 9, the group consisting of OOCR 10 and R 11 containing a substituted group selected from the group consisting of a combination thereof, R 9 is 3 carbon atoms To 20 primary or secondary aliphatic groups or aromatic groups of 6 to 20 carbon atoms and primary or secondary aliphatic groups of 3 to 20 carbon atoms containing aliphatic hydroxyl, ester, ether, carbonate and combinations thereof in the structure R 10 is selected from the group consisting of a primary, secondary or tertiary aliphatic group having 4 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, an aliphatic hydroxyl, an ester, an ether, a carbonate and combinations thereof in the structure A primary, secondary or tertiary aliphatic group having 4 to 20 carbon atoms and R 11 is selected from the group consisting of C 2 -C 20 organic radicals, Joan aliphatic hydroxyl, an ester, ether, carbonate, and C 2 -C 20 which forms a cyclic ring structure thereof containing formulation C 2 -C 20 organic radical, and 5 or 6 carbon atoms and R 6 together with the part Organic radicals; N is from about 1 to about 4; and R 12 is selected from the group consisting of alkyl, alkyl diisocyanate radicals, alkenyl, alkenyl diisocyanate radicals, aromatic and aromatic diisocyanate radicals do. 제17항에 있어서, 폴리올이 폴리에스테르 중합체, 아크릴 중합체, 알키드 중합체, 및 에폭시 중합체 및 이들의 혼합물로 이루어진 그룹 중에서 선택되는 중합체 비히클.18. The polymeric vehicle of claim 17 wherein the polyol is selected from the group consisting of polyester polymers, acrylic polymers, alkyd polymers, and epoxy polymers and mixtures thereof. 제17항에 있어서, 폴리올이 약 200 내지 약 20,000 범위의 수평균 분자량을 갖는 폴리에스테르 중합체인 중합체 비히클.18. The polymer vehicle of claim 17, wherein the polyol is a polyester polymer having a number average molecular weight in the range of from about 200 to about 20,000. 제17항에 있어서, 폴리올이 약 300 내지 약 5,000 범위의 수평균 분자량을 갖는 아크릴 중합체인 중합체 비히클.18. The polymer vehicle of claim 17, wherein the polyol is an acrylic polymer having a number average molecular weight in the range of from about 300 to about 5,000. 제17항에 있어서, 폴리올이 약 500 내지 약 20,000 범위의 수평균 분자량을 갖는 알키드 중합체인 중합체 비히클.18. The polymer vehicle of claim 17 wherein the polyol is an alkyd polymer having a number average molecular weight ranging from about 500 to about 20,000. 제17항에 있어서, 폴리올이 약 500 내지 약 6,000 범위의 수평균 분자량을 갖는 에폭시 중합체인 중합체 비히클.18. The polymer vehicle of claim 17 wherein the polyol is an epoxy polymer having a number average molecular weight ranging from about 500 to about 6,000. 제17항에 있어서, 폴리에스테르가 약 200 내지 약 20,000 의 분자량을 갖고 페놀 우레탄 반응성 희석제가 약 240 내지 약 1140 범위의 분자량을 갖는 중합체 비히클.18. The polymer vehicle of claim 17, wherein the polyester has a molecular weight of from about 200 to about 20,000 and the phenol urethane reactive diluent has a molecular weight in the range of from about 240 to about 1140. 제17항에 있어서, 폴리올이 약 300 내지 약 5,000의 수 평균 분자량을 갖는 아크릴 중합체이고 페놀 우레탄 반응성 희석제가 약 240 내지 약 1140 범위의 분자량을 갖는 중합체 비히클.18. The polymer vehicle of claim 17, wherein the polyol is an acrylic polymer having a number average molecular weight of from about 300 to about 5,000 and the phenol urethane reactive diluent has a molecular weight in the range of from about 240 to about 1140. 제17항에 있어서, 폴리올이 약 500 내지 약 10,000의 수 평균 분자량을 갖는 알키드 중합체이고 페놀 우레탄 반응성 희석제가 약 240 내지 약 1140 범위의 분자량을 갖는 중합체 비히클.18. The polymer vehicle of claim 17, wherein the polyol is an alkyd polymer having a number average molecular weight of from about 500 to about 10,000 and the phenol urethane reactive diluent has a molecular weight in the range of from about 240 to about 1140. 제17항에 있어서, 폴리올이 약 500 내지 약 6,000의 수 평균 분자량을 갖는 에폭시 중합체이고 페놀 우레탄 반응성 희석제가 약 240 내지 약 1140 범위의 분자량을 갖는 중합체 비히클.18. The polymer vehicle of claim 17, wherein the polyol is an epoxy polymer having a number average molecular weight of from about 500 to about 6,000 and the phenol urethane reactive diluent has a molecular weight in the range of from about 240 to about 1140. & 제17항에 있어서, 가교결합제, 폴리올 및 페놀 반응성 희석제가 각각 경화된 중합체 비히클로부터 제조된 코팅 바인더에 적어도 약 HB의 펜슬 경도 및 적어도 30인치 파운드 다이렉트 및 적어도 약 30인치 파운드 인다이렉트의 내충격성을 제공하기 위한 각각의 양으로 존재하는 중합체 비히클.18. The method of claim 17, wherein the crosslinking agent, polyol, and phenolic reactive diluent each have a pencil hardness of at least about HB and a impact resistance of at least about 30 inches pounds direct and at least about 30 inches pounds to a coating binder made from a cured polymer vehicle ≪ / RTI > polymeric vehicle. 제27항에 있어서, 폴리올이 약 200 내지 약 20,000의 수평균 분자량을 갖는 폴리에스테르인 중합체 비히클.28. The polymer vehicle of claim 27, wherein the polyol is a polyester having a number average molecular weight of from about 200 to about 20,000. 제27항에 있어서, 폴리올이 약 300 내지 약 5,000의 수평균 분자량을 갖는 아크릴 중합체인 중합체 비히클.28. The polymer vehicle of claim 27, wherein the polyol is an acrylic polymer having a number average molecular weight of from about 300 to about 5,000. 제27항에 있어서, 폴리올이 약 500 내지 약 6,000의 수평균 분자량을 갖는 알키드 중합체인 중합체 비히클.28. The polymer vehicle of claim 27, wherein the polyol is an alkyd polymer having a number average molecular weight of from about 500 to about 6,000. 제27항에 있어서, 폴리올이 약 500 내지 약 6,000의 수평균 분자량을 갖는 에폭시 중합체인 중합체 비히클.28. The polymer vehicle of claim 27, wherein the polyol is an epoxy polymer having a number average molecular weight of from about 500 to about 6,000. 제17항에 있어서, 중합체 비히클이 디페놀계 경화제인 제2경화제를 갖는 중합체 비히클.The polymer vehicle according to claim 17, wherein the polymer vehicle has a second curing agent which is a diphenolic curing agent. 제4항에 있어서, R12가5. The compound of claim 4 wherein R < 12 > is 로 이루어진 그룹 중에서 선택되고 R12가 이작용성 라디칼인 중합체 비하클Selected from the group consisting of and R 12 is proceed, the polymer is large compared soluble radical 제17항에 있어서, 이작용성 라디칼이18. The method of claim 17, wherein the bifunctional radical 로 이루어진 그룹 중에서 선택되는 중합체 비히클A polymeric vehicle selected from the group consisting of 제17항에 있어서, R12가18. The compound of claim 17, wherein R < 12 > is 로 이루어진 그룹 중에서 선택되고 R12가 이작용성 라디칼인 중합체 비히클R 12 is selected from the group consisting of a bifunctional radical of a polymer vehicle ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed by the contents of the first application.
KR1019970702300A 1995-08-09 1996-08-07 POLYMERIC VEHICLES WHICH INCLUDE A PHENOLIC URETHANE REACTIVE DILUENT, KR970706233A (en)

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US206395P 1995-08-09 1995-08-09
US08/621,177 1996-03-21
US60/002,063 1996-03-21
US08/621,177 US5973072A (en) 1996-03-21 1996-03-21 Polymeric vehicles which include a phenolic urethane reactive diluent
PCT/US1996/012915 WO1997006129A1 (en) 1995-08-09 1996-08-07 Polymeric vehicles which include a phenolic urethane reactive diluent

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