GB1499122A - Perfluoroalkylthio group-containing polyurethanes process for their manufacture and their use - Google Patents

Perfluoroalkylthio group-containing polyurethanes process for their manufacture and their use

Info

Publication number
GB1499122A
GB1499122A GB456175A GB456175A GB1499122A GB 1499122 A GB1499122 A GB 1499122A GB 456175 A GB456175 A GB 456175A GB 456175 A GB456175 A GB 456175A GB 1499122 A GB1499122 A GB 1499122A
Authority
GB
United Kingdom
Prior art keywords
urethanes
integer
alkylene
substituted
feb
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB456175A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US05/439,497 external-priority patent/US3935277A/en
Priority claimed from US05/462,169 external-priority patent/US3968066A/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1499122A publication Critical patent/GB1499122A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3863—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms
    • C08G18/3865—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms containing groups having one sulfur atom between two carbon atoms
    • C08G18/3868—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms containing groups having one sulfur atom between two carbon atoms the sulfur atom belonging to a sulfide group
    • C08G18/387—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms containing groups having one sulfur atom between two carbon atoms the sulfur atom belonging to a sulfide group in addition to a perfluoroalkyl group

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1499122 Fluoroalkylthio-urethanes CIBAGEIGY AG 3 Feb 1975 [4 Feb 1974 18 April 1974] 4561/75 Heading C2C [Also in Divisions C3 and D1-D2] Urethanes are prepared by reacting a monoisocyanate with an Rp-glycol of the formula wherein Rp is C 1-18 perfluoroalkyl which may be substituted by perfluoroalkoxy of 2 to 6 carbon atoms; R 1 is branched or straight chain C 1-12 alkylene, C 2-12 alkylenethioalkylene, alkyleneoxyalkylene or alkylene iminoalkylene where the nitrogen atom is optionally substituted by C 1-6 alkyl; R 2 and R 3 are each independently straight or branched chain alkylene of 1 to 12 carbon atoms and may be substituted by 1 or 2 phenyl and/or cyclohexyl radicals; or a group of formula C m H 2m (OC k H 2k ) r , where m is an integer from 1 to 12, k is an integer from 2 to 6, and r is an integer from 1 to 40. In Example 42 a commercial monoisocyanate containing 70% octadecyl isocyanate and 30% hexadecyl isocyanate is reacted with 2,3-bis-(1,1,2,2-tetrahydroperfluorodecylthio) - butane - 1,4 - diol. The urethanes may be used to render plastics soil repellent or for treating textiles to render them oil and/or water repellent.
GB456175A 1974-02-04 1975-02-03 Perfluoroalkylthio group-containing polyurethanes process for their manufacture and their use Expired GB1499122A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US05/439,497 US3935277A (en) 1974-02-04 1974-02-04 New Rf -glycols containing two perfluoroalkylthio groups and useful compositions therefrom
US05/462,169 US3968066A (en) 1974-04-18 1974-04-18 Oil and water repellent textile composition containing a fluorochemical polyurethane resin and a quaternary ammonium salt

Publications (1)

Publication Number Publication Date
GB1499122A true GB1499122A (en) 1978-01-25

Family

ID=27032062

Family Applications (1)

Application Number Title Priority Date Filing Date
GB456175A Expired GB1499122A (en) 1974-02-04 1975-02-03 Perfluoroalkylthio group-containing polyurethanes process for their manufacture and their use

Country Status (6)

Country Link
JP (1) JPS5518246B2 (en)
CA (1) CA1066842A (en)
CH (1) CH606175A5 (en)
DE (1) DE2503872A1 (en)
FR (1) FR2267334B1 (en)
GB (1) GB1499122A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2119708A (en) * 1982-04-29 1983-11-23 Duni Bila Ab Absorption pad

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4046944A (en) * 1976-04-06 1977-09-06 Ciba-Geigy Corporation Fluorinated condensation polymers and their use as soil release agents
JPS54128991A (en) * 1978-03-31 1979-10-05 Asahi Glass Co Ltd Water and oil repellent with superior durability
JPS56129281A (en) * 1980-03-14 1981-10-09 Asahi Glass Co Ltd Soil resistant finishing agent composition
DE3319368A1 (en) * 1983-05-27 1984-11-29 Bayer Ag, 5090 Leverkusen PERFLUORALKYL GROUPS CONTAINING POLYURETHANES AND METHOD FOR THE PRODUCTION THEREOF
US4496708A (en) * 1983-12-14 1985-01-29 Union Carbide Corporation Water-soluble polyurethane comb polymer production
JPS61252220A (en) * 1985-04-30 1986-11-10 Dainippon Ink & Chem Inc Polyurethane resin
ES2708202T3 (en) * 2015-06-25 2019-04-09 Covestro Deutschland Ag Polyurethane dispersions devoid of urea
KR20200055787A (en) * 2017-09-27 2020-05-21 알케마 인코포레이티드 Addition and condensation polymers prepared from halogenated reactants
WO2021117687A1 (en) * 2019-12-13 2021-06-17 Ａｇｃ株式会社 Fluorine-containing ether compound, composition, and article having water- and oil-repellent layer

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3759874A (en) * 1971-08-30 1973-09-18 Fmc Corp Fluorinated polyurethanes as soil release agents

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2119708A (en) * 1982-04-29 1983-11-23 Duni Bila Ab Absorption pad

Also Published As

Publication number Publication date
JPS50114497A (en) 1975-09-08
DE2503872C2 (en) 1987-11-19
CH606175A5 (en) 1978-10-31
FR2267334B1 (en) 1977-11-18
CA1066842A (en) 1979-11-20
FR2267334A1 (en) 1975-11-07
DE2503872A1 (en) 1975-10-30
JPS5518246B2 (en) 1980-05-17

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years

Effective date: 19950202