KR970065579A - Moisture-curable one-pack type polyurethane composition and method for producing the same - Google Patents

Moisture-curable one-pack type polyurethane composition and method for producing the same Download PDF

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KR970065579A
KR970065579A KR1019960007238A KR19960007238A KR970065579A KR 970065579 A KR970065579 A KR 970065579A KR 1019960007238 A KR1019960007238 A KR 1019960007238A KR 19960007238 A KR19960007238 A KR 19960007238A KR 970065579 A KR970065579 A KR 970065579A
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amine
isocyanate
moisture
curable
ketone
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KR100192201B1 (en
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최근배
오주영
송요승
송병창
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김평기
삼성포리머 주식회사
김동규
대한주택공사
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/302Water
    • C08G18/307Atmospheric humidity
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/32Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225Polyamines
    • C08G18/3253Polyamines being in latent form
    • C08G18/3256Reaction products of polyamines with aldehydes or ketones
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D175/00Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2190/00Compositions for sealing or packing joints

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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)
  • Polyurethanes Or Polyureas (AREA)

Abstract

하절기와 같은 고온 다습한 불리한 환경 조건하에서도 적용이 가능한 습기 경화성 1액형 폴리우레탄 조성물 및 그 제조 방법이 개시되어 있다. 폴리우레탄 조성물은 2가 또는 3가의 1차 아민에 케톤 단량체를 당량비로 아민의 30 - 70%를 혼합 반응시켜 세미케티민 화합물을 수득하고, 상기 세미케티민 화합물에 알데히드 단량체를 당량비로 아민의 30 - 70%를 혼합 반응시켜 잠재성 경화제 폴리알디민 - 케티민을 수득하고, 상기 폴리알디민 - 케티민과 폴리 이소시아네이트, 2개 이상의 이소시아네이트 기를 가지는 폴리우레탄 프리폴리머 또는 이들의 혼합물로 구성된 이소시아네이트 화합물을 혼합하여 제조한다 특히, 상기 조성물을 적용하여 폴리우레탄 방수재를 제조하면 습도 80%RH 이상, 적용 표면 온도 50℃ 이상의 조건하에서도 부플림 현상이 없고 인장 강도 35㎏f/㎠, 인열 강도 30㎏f/㎝, 신장을 500% 이상의 물성을 확보 할 수 있다.A one-pack type polyurethane composition capable of being applied under adverse environmental conditions such as high temperature and high humidity such as the summer season, and a method for manufacturing the same. The polyurethane composition is prepared by mixing 30 to 70% of amines with a di- or tri-valent primary amine and a ketone monomer in an equivalent ratio to obtain a semicetrimine compound, adding an aldehyde monomer to the semi- - 70% are mixed and reacted to obtain a polyadimine-ketimine as a latent curing agent, and an isocyanate compound composed of the polyaldimine-ketimine and a polyisocyanate, a polyurethane prepolymer having two or more isocyanate groups, In particular, when a polyurethane waterproofing material is prepared by applying the composition described above, even when the humidity is 80% RH or more and the application surface temperature is 50 占 폚 or more, there is no flaking phenomenon and the tensile strength is 35 kgf / Cm and elongation of 500% or more can be secured.

Description

습기 경화성 1액형 폴리우레탄 조성물 및 이의 제조 방법Moisture-curable one-pack type polyurethane composition and method for producing the same

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

Claims (14)

2가 또는 3가의 1차 아민에 케톤 단량체를 단량비고 아민의 30 - 70%를 혼합 반응시켜 수득한 세미케티민 화합물에 알데히드 단량체를 단량비로 아민의 30 - 70%를 혼합 반응시켜 얻은 잠재성 경화제 폴리알디민 - 케티민; 및 폴리이소시아네이트, 2개 이상의 이소시아네이트 기를 가지는 폴리우레탄 프리롤리머 또는 이들의 혼합물로 구성된 이소시아네이트 화합물로 이루어진 습기 경화성 1액형 폴리우레탄 조성물.A latent curing agent obtained by mixing 30 to 70% of an amine with a mono-, di- or trivalent primary amine and a ketone monomer in an amount of 30 to 70% of an amine with a monomeric ratio of an aldehyde monomer to a semicetrimine compound obtained by mixing 30 to 70% Polyadmin-ketamine; And an isocyanate compound composed of a polyisocyanate, a polyurethane prorolymer having two or more isocyanate groups, or a mixture thereof. 제1항에 있어서, 상기 아민으로서 지방족 1급 아민 및 2급 아민으로 구성되고 분자량이 200 - 1000인 이소포론디아민, 폴리옥시프로필렌디아민, 폴리옥시프로필렌트리아민 및 이들의 유기체, 메탄, 디아민, 에틸렌디아민, 프로필렌디아민, 메타크실렌디아민으로 구성된 군에서 선택된 적어도 어느 하나를 사용하는 것을 특징으로 하는 습기 경화성 1액형 폴리우레탄 조성물.The method of claim 1, wherein the amine is selected from the group consisting of isophoronediamine, polyoxypropylene diamine, polyoxypropylene triamine, and organisms thereof, which are composed of aliphatic primary and secondary amines and have a molecular weight of 200 to 1000, methane, diamine, ethylene Wherein the moisture-curable one-component polyurethane composition is at least one selected from the group consisting of diamine, propylene diamine, and metaxylenediamine. 제1항에 있어서, 상기 케톤 단량체로서 메킬이소부틸케톤, 디아소부틸케톤, 메틸에틸케톤, 아세톤, 메틸 - n - 프로필케톤, 메틸 - n - 부틸케톤, 에틸부틸케톤으로 구성된 군에서 선택한 적어도 어는 하나를 사용하는 것을 특징으로 하는 습기 경화성 1액형 폴리우레탄 조성물.The method of claim 1, wherein the ketone monomer is at least one selected from the group consisting of methyl isobutyl ketone, diisobutyl ketone, methyl ethyl ketone, acetone, methyl-n-propyl ketone, methyl-n-butyl ketone and ethyl butyl ketone Wherein the moisture-curable one-pack type polyurethane composition is used as the moisture-curable one-pack type polyurethane composition. 제1항에 있어서, 상기 알데이드 단량체로서 아세트알데히드,프로피온알데히드, 벤잘데히드, 부틸알데히드,이소부틸알데히드로 구성된 군에서 선택된 적어도 하나를 하용하는 것을 특징으로 하는 습기 경화성 1액형 폴리우레탄 조성물.The moisture-curable one-pack type polyurethane composition according to claim 1, wherein the aldehyde monomer is at least one selected from the group consisting of acetaldehyde, propionaldehyde, benzaldehyde, butylaldehyde, and isobutylaldehyde. 제1항에 있어서, 상기 이소시아네이트 화합물로서 지방족 또는 방향족 디아소시아네이트, 변성 이소시아네이트, 폴리머릭 이소시아네이트, 또는 이들로부터 선택되어진 이소시아네이트와 디올 또는 트리올의 폴리에테르폴리올, 폴리에스테르폴리올, 하이드록실폴리카보네이트 등의 단독 또는 이들의 혼합물과의 반응에 의해 수득한 프리폴리머로서 이소시아네이트의 기의 함량%가 상기 프리폴리머 100중량%에 대해 2 - 10중량%인 것을 특징으로 하는 습기 경화성 1액형 폴리우레탄 조성물.The method of claim 1, wherein the isocyanate compound is an aliphatic or aromatic diisocyanate, a modified isocyanate, a polymeric isocyanate, or a polyether polyol of a diol or a triol selected from the group consisting of a polyether polyol, a polyester polyol and a hydroxyl polycarbonate Wherein the content of isocyanate groups in the prepolymer obtained by the reaction with a mixture of a polyisocyanate and a polyisocyanate is from 2 to 10% by weight based on 100% by weight of the prepolymer. 제1항에 있어서, 상기 폴리알디민 - 케티민과 상기 이소시아네이트의 혼합 비율은 상기 폴리알디민 - 케티민이 촉매 존재 하에서 가수분해되어 생성되는 아미노기의 수가 이소시아네이트 화합물의 이소시아네이트 기수의 1.0 - 1.5배가 되도록 혼합하는 것을 특징으로 하는 습기 경화성 1액형 폴리우레탄 조성물.The method of claim 1, wherein the mixing ratio of the polyaldimine-ketimine and the isocyanate is such that the number of amino groups produced by the hydrolysis of the polyaldimine-ketimine in the presence of a catalyst is 1.0-1.5 times the number of isocyanate groups of the isocyanate compound Wherein the moisture-curable one-component polyurethane composition is a polyurethane composition. 2가 또는 3가의 1차 아민에 케톤 단량체를 당량비로 아민의 30 - 70%를 혼합 반응시켜 세미케티민 화합물을 수득하는 단계; 상기 세미케티민 화합물에 알데히드 단량체를 당량비로 아민의 30 - 70% 혼합 반응시켜 잠재성 경화제 폴리알디민 - 케티민을 수득하는 단계; 및 상기 폴리알디민 - 케티민과 폴리 이소시아네이트. 2개 이사의 이소시아네이트 기를 가지는 폴리우레탄 프리폴리머 또는 이들의 혼합물로 구성된 이소시아네이트 화합물을 혼합하는 단계로 이루어진 습기 경화성 1액형 폴리우레탄 조성물의 제조 방법.Reacting a divalent or trivalent primary amine with a ketone monomer in an equivalent ratio of 30 to 70% of an amine to obtain a semicetrimine compound; Reacting the semi-ketimine compound with an aldehyde monomer in an equivalent ratio of 30 to 70% of amine to obtain a latent curing agent polyadimine-ketimine; And polyadimine-ketimine and polyisocyanate. A polyurethane prepolymer having an isocyanate group of two isocyanate groups, or an isocyanate compound composed of a mixture thereof. 제7항에 있어서, 상기 세미케티민 화합물의 반응시에 촉진제로 칼슘클로라이드, 마그네슘설페이트, 티타늄테트라클로라이드, 포타슘카보네이트, 바륨옥사이드, 징크클로라이드, 제올라이트로 이루어진 군에서 선택한 적어도 어느 하나의 흡습제를 사용하는 것을 특징으로 하는 습기 경화성 1액형 폴리우레탄 조성물의 제조 방법.The method of claim 7, wherein at least one of the moisture absorbers selected from the group consisting of calcium chloride, magnesium sulfate, titanium tetrachloride, potassium carbonate, barium oxide, zinc chloride and zeolite is used as a promoter in the reaction of the semicetrimine compound Wherein the moisture-curable one-component polyurethane composition is a polyurethane composition. 제7항에 있어서, 상기 이소시아네이트 화합물은 지방족 또는 방향족 디이소시아네이트, 변성 이소시아네이트, 폴리머릭 이소시아네이트, 또는 이들로부터 선택되는 이소시아네이트와 디올 또는 트리올의 폴리에테르폴리올, 폴리에스테르폴리올, 하이드록실폴리카보네이트 등의 단독 또는 이들의 혼합물에 사슬 연장제로써 반응시켜 스득하는 것을 특징으로 하는 습기 경화성 1액형 폴리우레탄 조성물의 제조 방법.The method of claim 7, wherein the isocyanate compound is selected from the group consisting of an aliphatic or aromatic diisocyanate, a modified isocyanate, a polymeric isocyanate, or a polyether polyol of a diol or triol selected from the group consisting of polyether polyol, polyester polyol and hydroxyl polycarbonate Or a mixture thereof is reacted with a chain extender to obtain a moisture-curable one-pack type polyurethane composition. 2가 또는 3가의 1차 아민에 케톤 단량체를 당량비로 아민의 30 - 70%를 혼합 반응시켜 수득한 세미케티민 화합물에 알데히드 단량체를 당량비로 아민의 30 - 70%를 혼합 반응시켜 얻은 잠재성 경화제 폴리알디민 - 케티민과 폴리 이소시아네이트, 2개의 이상의 이소시아네이트 기를 가지는 폴리우레탄 프리폴리머 또는 이들의 혼합물로 구성된 이소시아네이트 화합물을 포함하고, 충진제로서 탄산칼륨, 탈크, 실리카, 황산 바륨, 카올린, 클레이에서 선택되는 적어도 어느 하나를 전체 배합물의 30 - 50중량% 범위에서 포함하고, 착색제, 가소제, 첨가제를 포함하는 습기 경화성 1액형 풀리우레탄 방수재.A latent curing agent obtained by mixing 30 to 70% of an amine with an equivalent amount of a primary or secondary amine of a di- or trivalent amine and mixing 30 to 70% of an amine with an aldehyde monomer in an equivalent ratio to a semi- An isocyanate compound composed of polyadimine-ketimine and polyisocyanate, a polyurethane prepolymer having two or more isocyanate groups, or a mixture thereof, wherein the filler is at least one selected from the group consisting of potassium carbonate, talc, silica, barium sulfate, kaolin and clay A moisture-curable one-part pulley-urethane waterproofing material comprising one of a colorant, a plasticizer and an additive in a range of 30 to 50% by weight of the total blend. 2가 또는 3가의 1차 아민에 케톤 단량체를 당량비로 아민의 30 - 70%를 혼합 반응시켜 얻어진 세미케티민 화합물에 알데히드 단량체를 당량비로 아민의 30 - 70%를 혼합 반응시켜 얻은 잠재성 경화제 폴리알디민 - 케티민과 폴리 이소시아네이트, 2개 이상의 이소시아네이트 기를 가지는 폴리우레탄 프리폴리머 또는 이들의 혼합물로 구성된 이소시아네이트 화합물을 포함하고, 충진제로서 탄산칼륨, 탈크 실리카, 황산 바륨, 카올린, 클레이에서 선택돈 적어도 어느 하나를 전체 배합물 중의 30 - 50중량% 범위에서 포함하고, 착색제, 가소제, 첨가제를 포함하는 습기 경화성 1액형 폴리우레탄 바닥재.A latent curing agent obtained by mixing 30 to 70% of amines with a di- or tri-valent primary amine and a ketone monomer in an equivalent ratio to 30 to 70% of an amine in an equivalent ratio of an aldehyde monomer to a semi- At least one selected from potassium carbonate, talc silica, barium sulfate, kaolin and clay as a filler, and an isocyanate compound composed of a polyisocyanate, a polyurethane prepolymer having two or more isocyanate groups, In the range of 30 to 50 weight percent of the total formulation, and comprising a colorant, a plasticizer, and an additive. 2가 또는 3가의 1차 아민에 케톤 단량체를 당량비로 아민의 30 - 70%를 혼합 반응시켜 얻어진 세미케티민 화합물에 알데히드 단량체를 당량비로 아민의 30 - 70%를 혼합 반응시켜 얻은 잠재성 경화제 폴리알디민 - 케티민과 폴리 이소시아네이트, 2개 이상의 이소시아네이트 기를 가지는 폴리우레탄 프리폴리머 또는 이들의 혼합물로 구성된 이소시아네이트 화합물을 포함하고, 흐림 방지용 충진제, 착색제, 가소제, 및 첨가제를 포함하는 습기 경화성 1액형 폴리우레탄 씰링제.A latent curing agent obtained by mixing 30 to 70% of amines with a di- or tri-valent primary amine and a ketone monomer in an equivalent ratio to 30 to 70% of an amine in an equivalent ratio of an aldehyde monomer to a semi- A moisture-curable one-component polyurethane sealant comprising an isocyanate compound composed of an aldimine-ketimine and a polyisocyanate, a polyurethane prepolymer having two or more isocyanate groups, or a mixture thereof, and containing an anti-fogging filler, a colorant, a plasticizer, My. 2가 또는 3가의 1차 아민에 케톤 단량체를 당량비로 아민의 30 - 70%를 혼합 반응시켜 얻어진 세미케티민 화합물에 알데히드 단량체를 당량비로 아민의 30 - 70%를 혼합 반응시켜 얻은 잠재성 경화제 폴리알디민 - 케티민과 폴리 이소시아네이트, 2개 이상의 이소시아네이트 기를 가지는 폴리우레탄 프리폴리머 또는 이들의 혼합물로 구성된 이소시아네이트 화합물을 포함하고, 충진제, 착색제, 가소제, 및 첨가제를 포함하는 습기 경화성 1액형 폴리우레탄 접착제.A latent curing agent obtained by mixing 30 to 70% of amines with a di- or tri-valent primary amine and a ketone monomer in an equivalent ratio to 30 to 70% of an amine in an equivalent ratio of an aldehyde monomer to a semi- 1-part polyurethane adhesive comprising an isocyanate compound composed of an aldimine-ketimine and a polyisocyanate, a polyurethane prepolymer having two or more isocyanate groups, or a mixture thereof, and containing a filler, a colorant, a plasticizer and an additive. 2가 또는 3가의 1차 아민에 케톤 단량체를 당량비로 아민의 30 - 70%를 혼합 반응시켜 얻어진 세미케티민 화합물에 알데히드 단량체를 당량비로 아민의 30 - 70%를 혼합 반응시켜 얻은 잠재성 경화제 폴리알디민 - 케티민과 폴리 이소시아네이트, 2개 이상의 이소시아네이트 기를 가지는 폴리우레탄 프리폴리머 또는 이들의 혼합물로 구성된 이소시아네이트 화합물을 포함하고, 충진제, 착색제, 가소제, 및 첨가제를 포함하는 습기 경화성 1액형 폴리우레탄 코팅제.A latent curing agent obtained by mixing 30 to 70% of amines with a di- or tri-valent primary amine and a ketone monomer in an equivalent ratio to 30 to 70% of an amine in an equivalent ratio of an aldehyde monomer to a semi- A moisture-curable one-pack type polyurethane coating composition comprising an isocyanate compound composed of an aldimine-ketamine and a polyisocyanate, a polyurethane prepolymer having two or more isocyanate groups, or a mixture thereof, and containing a filler, a colorant, a plasticizer and an additive. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed by the contents of the first application.
KR1019960007238A 1996-03-18 1996-03-18 Moisture curing one component polyurethane composition and preparation method thereof KR100192201B1 (en)

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