GB933056A - Improvements in fluorinated ethers - Google Patents

Improvements in fluorinated ethers

Info

Publication number
GB933056A
GB933056A GB281960A GB281960A GB933056A GB 933056 A GB933056 A GB 933056A GB 281960 A GB281960 A GB 281960A GB 281960 A GB281960 A GB 281960A GB 933056 A GB933056 A GB 933056A
Authority
GB
United Kingdom
Prior art keywords
treated
hydrogen
acetate
treatment
compound
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
GB281960A
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.)
3M Co
Original Assignee
Minnesota Mining and Manufacturing Co
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
Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Publication of GB933056A publication Critical patent/GB933056A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
    • B23Q—DETAILS, COMPONENTS, OR ACCESSORIES FOR MACHINE TOOLS, e.g. ARRANGEMENTS FOR COPYING OR CONTROLLING; MACHINE TOOLS IN GENERAL CHARACTERISED BY THE CONSTRUCTION OF PARTICULAR DETAILS OR COMPONENTS; COMBINATIONS OR ASSOCIATIONS OF METAL-WORKING MACHINES, NOT DIRECTED TO A PARTICULAR RESULT
    • B23Q3/00—Devices holding, supporting, or positioning work or tools, of a kind normally removable from the machine
    • B23Q3/02—Devices holding, supporting, or positioning work or tools, of a kind normally removable from the machine for mounting on a work-table, tool-slide, or analogous part
    • B23Q3/06—Work-clamping means
    • B23Q3/08—Work-clamping means other than mechanically-actuated
    • 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
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/438—Sulfonamides ; Sulfamic acids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
    • B23Q—DETAILS, COMPONENTS, OR ACCESSORIES FOR MACHINE TOOLS, e.g. ARRANGEMENTS FOR COPYING OR CONTROLLING; MACHINE TOOLS IN GENERAL CHARACTERISED BY THE CONSTRUCTION OF PARTICULAR DETAILS OR COMPONENTS; COMBINATIONS OR ASSOCIATIONS OF METAL-WORKING MACHINES, NOT DIRECTED TO A PARTICULAR RESULT
    • B23Q2703/00—Work clamping
    • B23Q2703/02—Work clamping means
    • B23Q2703/04—Work clamping means using fluid means or a vacuum
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2164—Coating or impregnation specified as water repellent
    • Y10T442/2172—Also specified as oil repellent
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2279—Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric
    • Y10T442/2287—Fluorocarbon containing

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Paper (AREA)

Abstract

Cellulosic materials are treated with quaternary ammonium salts of <FORM:0933056/IV(a)/1> where Rf C4-12 perfluoroalkyl, R is C1-12 alkylene, R1 is hydrogen or C1-6 alkyl and X is chlorine or bromine (for preparation see Group IV(b)). The compounds may react with cellulosic hydroxyl groups. The material may be treated in aqueous medium buffered to pH 5.5 to 6.5, dried at 40 DEG -100 DEG C., heated to fix the finish at 100 DEG -140 DEG C. and then, desirably, treated with a mild alkaline wash. Examples describe the treatment of cotton cloth using sodium acetate buffered solutions; rayon, acetate and paper are also specified cellulosic materials. Specifications 471,130 and 857,906 are referred to. ALSO:The invention comprises compounds of formula <FORM:0933056/IV(a)/1> where Rf is C4-12 perfluoroalkyl, R is C1-12 alkylene, R1 is hydrogen or C1-6 alkyl, and X is chlorine or bromine; and quaternary ammonium salt derivatives thereof with a tertiary organic base. They are prepared by treating a compound of formula <FORM:0933056/IV(a)/2> with formaldehyde and hydrogen chloride or hydrogen bromide, conveniently by passing gaseous hydrogen halide into a solution of the above alkanol and paraformaldehyde in an inert solvent; the mixture may be heated to about 25-100 DEG C. for completion. Quarternisation is conveniently effected by dissolving the halomethyl compound in ether or other solvent (e.g. toluene, benzene or dioxane) in which the quaternary salt is insoluble and adding the tertiary base while heating at 25-100 DEG C. Specified tertiary bases include trialkylamines, alkarylamines and heterocyclic amines. The quaternary derivatives are used to impart water-, oil- and soil-repellant properties to fibrous materials (see Groups IV(a) and IV(c)). 5-(N- methylperfluorooctanesulphonamido)-pentanol is obtained by alkaline hydrolysis (followed by acdification) of N-methyl-5-perfluorooctanesulphonamidopentyl acetate itself obtained by reacting the sodium salt of N-methylperfluorooctanesulphonamide with 5-chloropentyl acetate. Specifications 471,130 and 857,906 are referred to.ALSO:Water-, oil- and soil-repellant properties are imparted to woven and non-woven fibrous materials such as wool, cotton, rayon, acetate, nylon, paper, leather, wood, felt and to vitreous surfaces including glass fibres by treatment with a quaternary ammonium salt of a compound of formula <FORM:0933056/IV(a)/1> where Rf is C4-12 perfluoroalkyl, R is C1-12 alkylene, R1 is hydrogen or C1-6 alkyl and X is chlorine or bromine (for preparation see Group IV(b)). The material may be treated in aqueous medium buffered to pH 5,5 to 6,5, dried at 40 DEG -100 DEG C., heated to fix the finish at 100 DEG -140 DEG C., then desirably mildly alkaline washed and dried. The fluorinated compound may react with the material. The treatment may be applied to resin-treated, crease-resistant fabrics. Examples describe the treatment of cotton cloth using sodium acetate buffered solutions. Specifications 471,130 and 857,906 are referred to.
GB281960A 1959-02-02 1960-01-26 Improvements in fluorinated ethers Expired GB933056A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US79033459 US3147064A (en) 1959-02-02 1959-02-02 Fluorinated ethers and derivatives

Publications (1)

Publication Number Publication Date
GB933056A true GB933056A (en) 1963-07-31

Family

ID=25150356

Family Applications (1)

Application Number Title Priority Date Filing Date
GB281960A Expired GB933056A (en) 1959-02-02 1960-01-26 Improvements in fluorinated ethers

Country Status (3)

Country Link
US (1) US3147064A (en)
DE (1) DE1150383B (en)
GB (1) GB933056A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2639473A1 (en) * 1976-09-02 1978-03-09 Bayer Ag ALCOXYLATED PERFLUORALCAN SULPHONAMIDE

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3734687A (en) * 1969-04-04 1973-05-22 Fmc Corp A fabric finished with a fluorinated quarternized halomethyl ether
CH499470D (en) * 1969-04-04
US3923840A (en) * 1971-06-07 1975-12-02 Minnesota Mining & Mfg N-(furanylmethyl) fluoroalkanesulfonamides
US3993744A (en) * 1974-05-31 1976-11-23 Alberto Culver Company Live human hair treatment compositions containing perfluorinated compounds
US4176176A (en) * 1974-05-31 1979-11-27 Alberto-Culver Company Hair shampoo and cleanser compositions
US4013786A (en) * 1974-05-31 1977-03-22 Alberto Culver Company Hair creme rinses and hair conditioners containing hydrophobic-lipophobic perfluorinated compounds
US3993745A (en) * 1974-05-31 1976-11-23 Alberto Culver Company Perfluorinated compounds in hair treatment compositions
US4484990A (en) * 1980-06-16 1984-11-27 Minnesota Mining And Manufacturing Company Mist suppressant for solvent extraction metal electrowinning
US4362527A (en) * 1982-01-04 1982-12-07 The United States Of America As Represented By The Secretary Of Agriculture Radiation-resistant fluoroaromatic cellulosic ethers
US4873020A (en) * 1988-10-04 1989-10-10 Minnesota Mining And Manufacturing Company Fluorochemical surfactants and process for preparing same
US5821195A (en) * 1996-08-16 1998-10-13 Monsanto Company Sequential application method for enhancing glyphosate herbicidal effectiveness with reduced antagonism
JP4191250B2 (en) * 1996-08-16 2008-12-03 モンサント・テクノロジー・エルエルシー Sequential application method for treating plants with exogenous chemicals
US6992045B2 (en) 2000-05-19 2006-01-31 Monsanto Technology Llc Pesticide compositions containing oxalic acid
US7135437B2 (en) 2000-05-19 2006-11-14 Monsanto Technology Llc Stable liquid pesticide compositions
US6800117B2 (en) 2000-09-05 2004-10-05 Donaldson Company, Inc. Filtration arrangement utilizing pleated construction and method
EP1925352B1 (en) 2000-09-05 2015-07-01 Donaldson Company, Inc. Polymer, polymer microfiber, polymer nanofiber and applications including filter structure
US6743273B2 (en) 2000-09-05 2004-06-01 Donaldson Company, Inc. Polymer, polymer microfiber, polymer nanofiber and applications including filter structures
US7008904B2 (en) * 2000-09-13 2006-03-07 Monsanto Technology, Llc Herbicidal compositions containing glyphosate and bipyridilium
US8021457B2 (en) 2004-11-05 2011-09-20 Donaldson Company, Inc. Filter media and structure
EP2311543B1 (en) 2004-11-05 2015-07-01 Donaldson Company, Inc. Aerosol separator
US8057567B2 (en) 2004-11-05 2011-11-15 Donaldson Company, Inc. Filter medium and breather filter structure
EP3138621B1 (en) 2004-11-05 2020-01-08 Donaldson Company, Inc. Filter medium and structure
MX2007009400A (en) 2005-02-04 2007-08-16 Donaldson Co Inc Aerosol separator.
EP1858618B1 (en) 2005-02-22 2009-09-16 Donaldson Company, Inc. Aerosol separator
EP2117674A1 (en) 2007-02-22 2009-11-18 Donaldson Company, Inc. Filter element and method
WO2008103821A2 (en) 2007-02-23 2008-08-28 Donaldson Company, Inc. Formed filter element
US8267681B2 (en) 2009-01-28 2012-09-18 Donaldson Company, Inc. Method and apparatus for forming a fibrous media
BR112013023955B1 (en) 2011-03-18 2021-01-12 Donaldson Company, Inc. NON-WOVEN BLANKET UNDERSTANDING FIBERS IN A THERMALLY LINED BLANKET, METHOD FOR THE PRODUCTION OF A NON-WOVEN BLANKET THAT UNDERSTANDS A THERMALLY LINED BLANKET AND SUITABLE PASTAAQUOSA TO FORM A NON-WOVEN BLANKET
US9317068B2 (en) 2012-09-24 2016-04-19 Donaldson Company, Inc. Venting assembly and microporous membrane composite

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2146392A (en) * 1939-02-07 Quaternary ammonium salts
DE710965C (en) * 1937-12-25 1941-09-24 I G Farbenindustrie Akt Ges Process for the preparation of halogen-containing formaldehyde condensation products from sulfonamides
DE729892C (en) * 1937-12-25 1943-01-04 Ig Farbenindustrie Ag Process for the preparation of condensation products of sulfonic acid amides
US2204653A (en) * 1938-12-06 1940-06-18 Rohm & Haas Aliphatic di-oxymethylene quaternary ammonium halides and process for producing them
US2212654A (en) * 1938-12-17 1940-08-27 Du Pont Process for preparing quaternary ammonium compounds and intermediates therefor
US2314277A (en) * 1939-05-23 1943-03-16 Rohm & Haas Process for glazing fabric
US2567011A (en) * 1949-01-10 1951-09-04 Minnesota Mining & Mfg Fluorocarbon acids and derivatives
US2609270A (en) * 1949-11-15 1952-09-02 Inst Textile Tech Mildewproof cellulose produced by reaction with chlord-benzyl quaternary ammonium salts
US2732398A (en) * 1953-01-29 1956-01-24 cafiicfzsojk
US2793929A (en) * 1953-12-04 1957-05-28 Onyx Oil And Chemical Company Process of shrinkproofing regenerated cellulose fabric with alkoxymethylene quaternary ammonium compositions and product produced therefrom
US2759019A (en) * 1954-08-09 1956-08-14 Minnesota Mining & Mfg Perfluoro amine compounds and quaternary derivatives
US2803656A (en) * 1956-01-23 1957-08-20 Minnesota Mining & Mfg Fluorocarbonsulfonamidoalkanols and sulfates thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2639473A1 (en) * 1976-09-02 1978-03-09 Bayer Ag ALCOXYLATED PERFLUORALCAN SULPHONAMIDE

Also Published As

Publication number Publication date
DE1150383B (en) 1963-06-20
US3147064A (en) 1964-09-01

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