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GB1102903A - Fluoro alkyl-containing compounds and water- and oil-repellent compositions containing them - Google Patents

Fluoro alkyl-containing compounds and water- and oil-repellent compositions containing them

Info

Publication number
GB1102903A
GB1102903A GB732265A GB732265A GB1102903A GB 1102903 A GB1102903 A GB 1102903A GB 732265 A GB732265 A GB 732265A GB 732265 A GB732265 A GB 732265A GB 1102903 A GB1102903 A GB 1102903A
Authority
GB
United Kingdom
Prior art keywords
compounds
prepared
formula
copolymers
formulae
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
GB732265A
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.)
Daikin Industries Ltd
Original Assignee
Daikin Industries Ltd
Daikin Kogyo Co Ltd
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 JP3154064A external-priority patent/JPS4841152B1/ja
Application filed by Daikin Industries Ltd, Daikin Kogyo Co Ltd filed Critical Daikin Industries Ltd
Publication of GB1102903A publication Critical patent/GB1102903A/en
Expired legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/11—Halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
    • C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
    • C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
    • C07C53/19—Acids containing three or more carbon atoms
    • C07C53/21—Acids containing three or more carbon atoms containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/38—Acyl halides
    • C07C53/46—Acyl halides containing halogen outside the carbonyl halide group
    • C07C53/50—Acyl halides containing halogen outside the carbonyl halide group of acids containing three or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
    • C07D203/18—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carboxylic acids, or by sulfur or nitrogen analogues thereof
    • 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
    • C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
    • 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
    • C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
    • C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/12—Aldehydes; Ketones
    • D06M13/133—Halogenated aldehydes; Halogenated ketones ; Halogenated ketenes
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • D06M13/236—Esters of carboxylic acids; Esters of carbonic acid containing halogen atoms
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/395—Isocyanates
    • D06M13/398—Isocyanates containing fluorine atoms
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/487—Aziridinylphosphines; Aziridinylphosphine-oxides or sulfides; Carbonylaziridinyl or carbonylbisaziridinyl compounds; Sulfonylaziridinyl or sulfonylbisaziridinyl compounds
    • D06M13/493—Aziridinylphosphines; Aziridinylphosphine-oxides or sulfides; Carbonylaziridinyl or carbonylbisaziridinyl compounds; Sulfonylaziridinyl or sulfonylbisaziridinyl compounds perfluorinated
    • 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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
    • 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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/347—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated ethers, acetals, hemiacetals, ketones or aldehydes
    • D06M15/353—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated ethers, acetals, hemiacetals, ketones or aldehydes containing fluorine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises homopolymers and copolymers of compounds of the formulae Rt(CH2)m1OCO(CH2)p1CR1 =CH2 Rt(CH2)mCOO(CH2)p2CH=CH2 and RtCONH(CH2)rOCO(CH2)p1CR1 =CH2 wherein Rt is (CF3)2CF(CF2)n-, R1 is H or CH3, n is 2-20, m is 0-20, m1 is 1-20, p1 is 0-20, p2 is 1-20 and r is 2-10. The copolymers may be copolymers of at least two of said unsaturated compounds or copolymers of at least one of said unsaturated compounds in an amount of at least 25% by weight and a polymerizable ethylenic monomer. The invention also comprises a polyester prepared by esterifying 30 to 100% of the hydroxyl groups in a polyvinyl alcohol, having an average polymerization degree of 300 to 1000 and a saponification value of 70-100%, with an acid halide Rt(CH2)mCOX, where X is -F, -Cl, -Br or -I and Rt, n and m are as defined above. The above compositions may be dissolved or suspended in dispersion media, e.g., acetone, ether or C2Cl3F3.ALSO:The invention comprises compounds of the general formulae Rf(CH2)mCOX Rf(CH2)m1OCOCH2X Rf(CH2)m1OCO-NHR-NCO Rf(CH2)m1OCO(CH2)p1 -CR1 = CH2 Rf(CH2)mCOO(CH2)p2-CH = CH2 [Rf(CH2)m1-O-]q-T -X3- q [Rf(CH2)m1-NH-]q-T -X3- q Rf-CONH(CH2)rOCOCH2X Rf-CONH(CH2)rOCO-NHR-NCO Rf-CONH(CH2)rOCO(CH2)p1 -CR1 = CH2 <FORM:1102903/C2/1> [Rf-CONH(CH2)rO-]q-T -X3- q [Rf-CONH(CH2)rNH-]q-T-X3- q\t and Fe, Zr, Al and Cr salts of compounds of the formula Rf(CH2)mCOOH; in the above formulae Rf is (CF3)2CF(CF2)n-, R is selected from <PICT:1102903/C2/1> <PICT:1102903/C2/2> and -(CH2)k-, R1 is H or CH3 Y is C1- 3 alkyl, X is F, Cl, Br or I, T is the 1,3,5-triazin-2,4,6-triyl radical, k is 2-20, n is 2-20, m is 0-20, m1 is 1-20, p1 is 0-20, p2 is 1-20, q is 1 or 2, and r is 2-10. The compounds are prepared by conventional general processes from corresponding starting materials of the formulae Rf(CH2)m1OH . . . . (1) Rf(CH2)mCOOH . . . (2) RfCONH(CH2)rOH . . (3) RfCONH(CH2)rNH2 . . (4) and Rf(CH2)m1NH2 . . . (5) The starting materials of Formula (1) above are prepared by the reaction of a compound RfI with CH2 = CH(CH2)m2-2OH or CH2 = CH(CH2)m2-2OCOR11 where m2 is 3-20 and R11 is C1- 3 alkyl, to give products of the formula RfCH2CHI(CH2)m2-2OH or RfCH2CHI(CH2)m2-2OCOR11 respectively, which products are then, respectively, reduced or reduced and hydrolysed. The compounds of Formula (2) above are prepared by reacting Rf I with CH2 = CH(CH2)m2-2COOH or CH2 = CH(CH2)m2-2COOR11 to give, respectively, RfCH2CHI(CH2)m2-2COOH or RfCH2CHI(CH2)m2-2COOR11 which are then, respectively, reduced or reduced and hydrolysed. The compounds of Formula (3) above are prepared by reaction of RfCOOH with H2N(CH2)rOH. The compounds of Formulae (4) and (5) above are obtained from compounds of Formulae (3) and (1), respectively, by reaction with ammonia water. The compounds RfI where n is even are prepared from (CF3)2CFI and CF2 = CF2. The compound RfI where n is 4 may be reacted with ethylene to give RfCH2CH2I which is dehydroiodinated to RfCH = CH2 and the latter oxidized to RfCOOH.ALSO:Articles are rendered oil- and water-repellent by impregnating with compositions comprising at least one fluoroalkyl-containing compound dissolved or suspended in at least one liquid medium, said fluoralkyl-containing compound being present in the composition in an amount of at least 0.1 gram/100 ml. of said liquid medium and being selected from Groups A, B, C-1 and C-2 below. Group A consists of compounds of the formul <FORM:1102903/D1-D2/1> and {RtCONH(CH2)2NH-}a -T-X3-a where Rt is (CF3)2CF-(CF2)n-, R is selected from <FORM:1102903/D1-D2/2> and -(CH2)k-, R1 is H or CH3, T is the 1,3,5-triazin-2,4, or 6-triyl radical, X is F, Cl, Br or I, Y is C1-3 alkyl, k is 2-10, n is 2-20, m is 0-20, m1 is 1-20, p1 is 0-20, p2 is 1-20, q is 1 or 2 and r is 2-10. Group B consists of the Fe, Zr, Al and Cr salts of acids of the formula Rt(CH2)mCOOH where the symbols Rt and m have the same significance as in Group A alone. Group C2 consists of polyesters prepared by branched-chain fluoralkylcontaining unsaturated compounds, copolymers of at least two of said compounds, and copolymers of at least one of said compounds in at least 25% by weight with an ethylenic polymerisable substance, the said unsaturated compound being of formula Rt(CH2)m1 OCO(CH2)p1 CR1=CH2 Rt(CH2)mCOO(CH2)p2CH=CH2 or RtCONH(CH2)r OCO(CH2)p1 CR1=CH2 where Rt, R1, m, m1, p1, p2 and r are as defined alone. Group C2 consists of polyesters prepared by esterfying 30-100% of the hydroxyl groups of a polyvinyl alcohol, having an average polymerization degree of 300-1,000 and a saponification value of 70-100%, with a compound Rt(CH2)m COX where Rt, m and X are as defined above.
GB732265A 1964-02-24 1965-02-19 Fluoro alkyl-containing compounds and water- and oil-repellent compositions containing them Expired GB1102903A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP995764 1964-02-24
JP3154064A JPS4841152B1 (en) 1964-06-03 1964-06-03

Publications (1)

Publication Number Publication Date
GB1102903A true GB1102903A (en) 1968-02-14

Family

ID=26344783

Family Applications (1)

Application Number Title Priority Date Filing Date
GB732265A Expired GB1102903A (en) 1964-02-24 1965-02-19 Fluoro alkyl-containing compounds and water- and oil-repellent compositions containing them

Country Status (3)

Country Link
CH (2) CH443875A (en)
DE (1) DE1494430A1 (en)
GB (1) GB1102903A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0135705A1 (en) * 1983-07-29 1985-04-03 Kuraray Co., Ltd. Shaped article of synthetic resin having improved surface
GB2291439A (en) * 1994-07-19 1996-01-24 Secr Defence Oil and water repellent treatments
EP0849392A2 (en) * 1996-12-20 1998-06-24 Nippon Mektron, Ltd. Fluoroalkylated allylurethane, its copolymer and water- and oil-repellent, anti-soiling processing agent containing the copolymer as an effective component
WO1999005127A1 (en) * 1997-07-26 1999-02-04 The Secretary Of State For Defence Fluorinated triazine monomers
EP1033368A2 (en) * 1999-03-03 2000-09-06 Ausimont S.p.A. Fluorinated triazinic compounds
EP1557489A1 (en) * 1997-06-14 2005-07-27 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain Surface coatings
WO2008027736A1 (en) * 2006-08-31 2008-03-06 3M Innovative Properties Company Side chain fluorochemicals with crystallizable spacer groups
US8236425B2 (en) 2006-12-29 2012-08-07 3M Innovative Properties Company Long-chain polymethylene halide telomers
US8389070B2 (en) 2004-03-18 2013-03-05 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland Coating of a polymer layer using low power pulsed plasma in a plasma chamber of a large volume
CN105648770A (en) * 2016-03-25 2016-06-08 广州拜费尔空气净化材料有限公司 Method for preparing super-hydrophobic surfaces

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10057840A1 (en) * 2000-11-22 2002-06-06 Colloid Surface Technologies G Fibers and fabrics with fluorine-containing hydrophobic finish and process for making the same

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0135705A1 (en) * 1983-07-29 1985-04-03 Kuraray Co., Ltd. Shaped article of synthetic resin having improved surface
GB2291439A (en) * 1994-07-19 1996-01-24 Secr Defence Oil and water repellent treatments
EP0849392A2 (en) * 1996-12-20 1998-06-24 Nippon Mektron, Ltd. Fluoroalkylated allylurethane, its copolymer and water- and oil-repellent, anti-soiling processing agent containing the copolymer as an effective component
EP0849392A3 (en) * 1996-12-20 1999-07-21 Nippon Mektron, Ltd. Fluoroalkylated allylurethane, its copolymer and water- and oil-repellent, anti-soiling processing agent containing the copolymer as an effective component
EP1557489A1 (en) * 1997-06-14 2005-07-27 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain Surface coatings
USRE43651E1 (en) 1997-06-14 2012-09-11 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland Surface coatings
EP2275598A1 (en) * 1997-06-14 2011-01-19 The Secretary Of State For Defence DSLT Surface coatings
GB2342353A (en) * 1997-07-26 2000-04-12 Secr Defence Fluorinated triazine monomers
GB2342353B (en) * 1997-07-26 2001-10-03 Secr Defence Fluorinated triazine monomers and polymers providing oil- and water-repellency
US6514887B1 (en) 1997-07-26 2003-02-04 The Secretary Of State For Defence Fluorinated triazine monomers
WO1999005127A1 (en) * 1997-07-26 1999-02-04 The Secretary Of State For Defence Fluorinated triazine monomers
US6313291B1 (en) 1999-03-03 2001-11-06 Ausimont S.P.A. Fluorinated triazinic compounds
EP1033368A3 (en) * 1999-03-03 2000-09-20 Ausimont S.p.A. Fluorinated triazinic compounds
EP1033368A2 (en) * 1999-03-03 2000-09-06 Ausimont S.p.A. Fluorinated triazinic compounds
US8389070B2 (en) 2004-03-18 2013-03-05 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland Coating of a polymer layer using low power pulsed plasma in a plasma chamber of a large volume
WO2008027736A1 (en) * 2006-08-31 2008-03-06 3M Innovative Properties Company Side chain fluorochemicals with crystallizable spacer groups
CN101511768B (en) * 2006-08-31 2013-08-21 3M创新有限公司 Side chain fluorochemicals with crystallizable spacer groups
US8889230B2 (en) 2006-08-31 2014-11-18 3M Innovative Properties Company Side chain fluorochemicals with crystallizable spacer groups
US8236425B2 (en) 2006-12-29 2012-08-07 3M Innovative Properties Company Long-chain polymethylene halide telomers
CN105648770A (en) * 2016-03-25 2016-06-08 广州拜费尔空气净化材料有限公司 Method for preparing super-hydrophobic surfaces

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CH253565A4 (en) 1967-05-31
DE1494430A1 (en) 1969-10-09
CH443875A (en) 1967-09-15

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