KR910011979A - 지방족 플루오로 알콜, 이소시아네이트 및 카복실산으로부터 제조된 우레탄, 이의 제조방법 및 이의 용도 - Google Patents

지방족 플루오로 알콜, 이소시아네이트 및 카복실산으로부터 제조된 우레탄, 이의 제조방법 및 이의 용도 Download PDF

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KR910011979A
KR910011979A KR1019900021909A KR900021909A KR910011979A KR 910011979 A KR910011979 A KR 910011979A KR 1019900021909 A KR1019900021909 A KR 1019900021909A KR 900021909 A KR900021909 A KR 900021909A KR 910011979 A KR910011979 A KR 910011979A
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radical
carboxylic acid
aliphatic
aromatic
general formula
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크나우프 볼프강
쿱퍼 라이너
클레버 롤프
젝켈 로타르
골크 프리츠-요아힘
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펜스케, 라피스
훽스트 아크티엔게젤샤프트
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Publication of KR910011979A publication Critical patent/KR910011979A/ko

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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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • 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
    • 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
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
    • C07C275/58—Y being a hetero atom
    • C07C275/62—Y being a nitrogen atom, e.g. biuret
    • 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
    • C08G18/2885—Compounds containing at least one heteroatom other than oxygen or nitrogen containing halogen atoms
    • 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
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C08G18/343—Polycarboxylic acids having at least three carboxylic acid groups
    • C08G18/346—Polycarboxylic acids having at least three carboxylic acid groups having four carboxylic acid 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
    • C08G18/28—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
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C08G18/348—Hydroxycarboxylic 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
    • C08G18/3821—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • D06M15/576—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them containing fluorine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

내용 없음

Description

지방족 플루오로 알콜, 이소시아네이트 및 카복실산으로부터 제조된 우레탄, 이의 제조방법 및 이의 용도
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (5)

  1. 지방족 플루오로 알콜, 이소시아네이트 및 카복실산으로부터 제조된 하기 일반식(1)의 우레탄.
    상기식에서, Rf및 R'f는 각각 탄소수 4 내지 22의 퍼플루오로 알킬 그룹이고, x및 x′는 각각 1내지 4의 수이며, y및 y′는 각각 0 내지 7 의 수이고, A는 지방족, 방향족 또는 사이클로 지방족 트리이소시아네이트의 라디칼이며, R은 1내지 5개의 -COOM그룹(여기서, M은 수소 또는 염기 라디칼이다)을 갖는 방향족, 지방족 또는 사이클로 지방족 카복실산의 라디칼 또는 카복실산의 염이고, X는 -O-, 단일결합 또는 -NR′-[여기서, R′는 H, C1내지 C4-알킬 또는 -CH2COOM (여기서, M은 상기에서 정의된 바와 같다)이다]이며, s는 1 내지 3의 수이고, 단, Rf및 R'f가 각각 (C8F17-C16F33)-이고 x및x′및 y및y′가 각각 2이고, A가 구조식
    의 트리이소시아네이트 라디칼이며, X가 -O-또는 -NH-이고, R이 구조식
    의 방향족 카복실산 라디칼이며 s가 1인 우레탄 화합물은 제외된다.
  2. 제1항에 있어서, Rf및 R'f가 각각 탄소수 6 내지 18의 퍼플루오로알킬 그룹이고, x및x′가 각각 2이며, y및y′가 각각 1내지 7의 수이거나 또는 두지수중 하나는 0이고 다른 하나는 1내지 7의 수이고, A가 지방족 또는 방향족 트리이소시아네이트의 라디칼이며, R이 일반식 (8),
    또는 일반식(9)
    (여기서, M은 제1항에서 정의된 의미를 가지며 a1및 a2는 각각 1내지 5의 수이다)의 방향족 카복실산의 라디칼 또는 방향족 카복실산의 염이거나, 일반식(10)-R1-COOM (여기서, M은 상기에서 정의된 바와 같고 R1은 탄소수가 15이하인 지방족 탄화수소 라디칼이다)의 지방족 카복실산의 라디칼 또는 지방족 카복실산의 염이고, X는 -O-, 단일결합 또는 -NR′- (여기서, R′는 H 또는 C1내지C4-알킬이다)이고, s는 1내지 3의 수이고, 단 X가 -O- 또는 -NR′-인 경우 s는 1인 우레탄.
  3. 제1항에 있어서, Rf및 R'f가 각각 탄소수 6내지 18의 퍼플루오로알킬 그룹이고, x 및 x′가 각각 2이며, y및 y′가 각각 1 내지 7의 수이거나 또는 두지수중 하나는 0이고 다른 하나는 1내지 7의 수이고, A는 지방족 또는 방향족 트리이소시아네이트의 라디칼이며, R은 일반식(8)
    또는 일반식(9)
    (여기서, M은 제1항에서 정의된 의미를 가지며, a1및 a2는 각각 1,2 또는 3이다)의 방향족 카르복실산의 라디칼 또는 방향족 카복실산의 염이거나, 일반식(10)- R1-COOM (여기서, M은 제1항에서 정의된 바와 같고 R′은 -( CH2)z-라디칼이며, 여기에서 z는 1내지 10이다)의 지방족 카복실산의 라디칼 또는 지방족 카복실산의 염이거나, 또는 일반식 (11)내지 (13)의 라디칼이며,
    (11)
    (12)
    (13)
    (여기서, M은 제1항에서 정의된 바와 같고, m은 0이거나 1내지 7의 수이며, n은 1,2 또는 3이고, R2는 H,OH 또는 C1내지 C4-알킬이다)X는 -O-, 단일결합 또는 -NR′- (여기서, R′는 H 또는 C1내지C4-알킬이다)이고, s는 1내지 3의 수이고, 단 X가 -O- 또는 -NR′-인 경우 s는 1인 우레탄.
  4. 하기 일반식(27)의 플루오로 알콜/트리이소시아네이트 부가물 1 내지 3몰을 방향족, 지방족 또는 사이클로 지방족 카복실산 1 내지 3몰과 반응시키고, 부가물의 -NCO그룹에 대해 -OH, -NHR′(여기서, R1은 제1항에서 정의된 의미를 갖는다)또는 -COOH형의 카복실산 화합물 1내지 3H원자를 가함에 의해 목적하는 우레탄을 산의 형태로 수득하거나 또는 염기로 중화시킴에의해 목적하는 우레탄을 염의 형태로 수득함을 특징으로하여, 제1항에서 청구된 우레탄을 제조하는 방법.
    상기식에서 Rf및 R'f, x, x′, y, y′및 A는 제1항에서 정의된 바와 같다.
  5. 물, 오일 및 토양 기피성을 성취하기 위한 직물의 마무리 처리를 위한 제1항에서 청구된 우레탄의 용도.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900021909A 1989-12-28 1990-12-27 지방족 플루오로 알콜, 이소시아네이트 및 카복실산으로부터 제조된 우레탄, 이의 제조방법 및 이의 용도 KR910011979A (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3943127A DE3943127A1 (de) 1989-12-28 1989-12-28 Urethane als aliphatischen fluoralkoholen, isocyanaten und carbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung
DEP39431274 1989-12-28

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KR910011979A true KR910011979A (ko) 1991-08-07

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Country Link
US (1) US5171877A (ko)
EP (1) EP0435220A3 (ko)
JP (1) JPH03294258A (ko)
KR (1) KR910011979A (ko)
CA (1) CA2033313A1 (ko)
DE (1) DE3943127A1 (ko)

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US5350795A (en) * 1991-07-10 1994-09-27 Minnesota Mining And Manufacturing Company Aqueous oil and water repellent compositions which cure at ambient temperature
WO1993001349A1 (en) * 1991-07-10 1993-01-21 Minnesota Mining And Manufacturing Company Aqueous oil and water repellent compositions
DE4207851A1 (de) * 1992-03-12 1993-09-16 Bayer Ag Mittel und verfahren zur ausruestung von textilien
DE69324784T2 (de) * 1992-12-30 1999-10-21 Ici Plc Verfahren zur Herstellung von Hartschaumstoffen
US5496642A (en) * 1994-05-09 1996-03-05 Olin Corporation Low VOC, fluorocompound-containing one-component and two-component coating compositions for slippery coatings
US5629372A (en) * 1994-11-22 1997-05-13 E. I. Du Pont De Nemours And Company Acrylic fluorocarbon polymer containing coating
US5597874A (en) * 1995-10-16 1997-01-28 E. I. Du Pont De Nemours And Company Coating compositions of an acrylic fluorocarbon polymer and a fluorinated polyisocyanate
US5627238A (en) * 1995-10-16 1997-05-06 E. I. Du Pont De Nemours And Company Coating compositions of an acrylic polymer and a fluorinated polyisocyanate
US5605956A (en) * 1995-10-16 1997-02-25 E. I. Du Pont De Nemours And Company Fluorinated polyisocyanates
US5948851A (en) * 1997-11-21 1999-09-07 E. I. Du Pont De Nemours And Company Coating compositions containing a highly fluorinated polymeric additive
US5914384A (en) * 1997-11-21 1999-06-22 E. I. Du Pont De Nemours And Company Coating compositions containing a highly fluorinated hydroxyl containing additive
US6479612B1 (en) 1999-08-10 2002-11-12 E. I. Du Pont De Nemours And Company Fluorochemical water and oil repellents
US6824854B2 (en) * 2002-07-29 2004-11-30 E. I. Du Pont De Nemours And Company Carpets treated for soil resistance
EP1548001A4 (en) * 2002-08-06 2007-08-15 Daikin Ind Ltd Fluorinated urethane compounds and compositions containing them
US7160480B2 (en) * 2005-02-22 2007-01-09 E. I. Du Pont De Nemours And Company Leather treated with fluorochemicals
US20060188729A1 (en) * 2005-02-22 2006-08-24 Kai-Volker Schubert Washable leather with repellency
US10288543B2 (en) 2016-01-16 2019-05-14 Columbia Insurance Company Methods for determining moisture permeability in textiles

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US4564366A (en) * 1982-10-25 1986-01-14 Minnesota Mining And Manufacturing Company Leather with fluorochemical finish
US4525305A (en) * 1982-10-25 1985-06-25 Minnesota Mining And Manufacturing Company Leather with fluorochemical finish
US4539006A (en) * 1983-09-13 1985-09-03 Minnesota Mining And Manufacturing Company Leather treatment
US4606737A (en) * 1984-06-26 1986-08-19 Minnesota Mining And Manufacturing Company Fluorochemical allophanate compositions and fibrous substrates treated therewith
DE3540147A1 (de) * 1985-11-13 1987-05-14 Hoechst Ag Perfluoralkylgruppen, epichlorhydringruppen und dialkoholreste enthaltende urethane, verfahren zu ihrer herstellung und ihre verwendung
DE3622284A1 (de) * 1986-07-03 1988-01-07 Hoechst Ag Urethane aus aliphatischen fluoralkoholen, isocyanaten und aromatischen verbindungen, verfahren zu ihrer herstellung und ihre verwendung
DE3744423A1 (de) * 1987-12-29 1989-07-13 Hoechst Ag Urethane aus aliphatischen fluoralkoholen, isocyanaten und substituierten aromatischen verbindungen, verfahren zu ihrer herstellung und ihre verwendung

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JPH03294258A (ja) 1991-12-25
DE3943127A1 (de) 1991-07-04
CA2033313A1 (en) 1991-06-29
US5171877A (en) 1992-12-15
EP0435220A2 (de) 1991-07-03
EP0435220A3 (en) 1991-11-21

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