GB999795A - Fluorocarbon compounds - Google Patents

Fluorocarbon compounds

Info

Publication number
GB999795A
GB999795A GB3173461A GB3173461A GB999795A GB 999795 A GB999795 A GB 999795A GB 3173461 A GB3173461 A GB 3173461A GB 3173461 A GB3173461 A GB 3173461A GB 999795 A GB999795 A GB 999795A
Authority
GB
United Kingdom
Prior art keywords
group
perfluoroalkyl
formaldehyde
adducts
isocyanate
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
GB3173461A
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 GB999795A publication Critical patent/GB999795A/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
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8083—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen
    • C08G18/8087—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen containing halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C11/00—Surface finishing of leather
    • C14C11/003—Surface finishing of leather using macromolecular compounds
    • C14C11/006—Surface finishing of leather using macromolecular compounds using polymeric products of isocyanates (or isothiocyanates) with compounds having active hydrogen
    • 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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
    • 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
    • D06M13/425—Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes
    • D06M13/428—Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes 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
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/438—Sulfonamides ; Sulfamic acids
    • 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
    • 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
    • D21H17/09—Sulfur-containing compounds
    • 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

Landscapes

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

Abstract

The invention comprises adducts obtained by reacting an organic isocyanate and a sulphonamide containing a perfluoroalkyl terminal group having at least 4 carbon atoms and containing active hydrogen, the isocyanate being substantially free of acid, alcohol, amine, unsubstituted amide, ethylene and carboxylic ester groups. A preferred class of compounds is represented by the formula R[N(R1)SO2X]2 where R is an organic radical linked to the nitrogen atom via a carbon atom and contains a group derived from the isocyanate such as a urethane, a urea, a ureide or a mixed anhydride of carbamic acid, R1 is an alkyl radical containing less than 20 carbon atoms, and X is an organic radical containing a perfluoroalkyl grouo of the formula -(CF2)3- 17CF3. Suitable examples of fluorinated sulphonamides and isocyanates are given. In addition, a third compound containing reactive hydrogen but which does not contain a perfluoroalkyl group may also be present during the reaction. Examples given are alcohols, amines and acids. In detailed examples, urethanes or carbamic acid mixed anhydrides are made by reacting polyisocyanates with perfluoralkylsulphonamide-containing alcohols or acids. Specification 832,490 is referred to.ALSO:A process for imparting oil repellancy to a substrate comprises applying to the outer surface of said substrate an adduct obtained by reacting an organic isocyanate and a compound containing a sulphonamide group, a perfluoroalkyl terminal group having at least 4 carbon atoms, and a group containing an active hydrogen, for example an acid, alcohol, amine or amide group, with or without another compound containing a reactive hydrogen atom which does not contain a perfluoroalkyl group. The preferred adducts thus contain a urethane, urea, ureide or mixed anhydride of carbamic acid in addition to a sulphonamide and perfluoroalkyl group. The adducts may be applied by known methods of coating, such as spraying, roll coating, brushing or dipping from an organc solvent, solution or anionic, cationic or non-ionic emulsion. In treatment of textile fabrics the adducts may be employed in combination with crease resisting resin, e.g. urea-formaldehyde, ethylene urea-formaldehyde, melamine-formaldehyde, triazine-formaldehyde, and triazone-formaldehyde resins, epoxy resins, and polyglycol acetals; sizes, e.g. polyethylene glycols, polyethylene, dimethyl polysiloxanes, amines and amides derived from fatty acids and ethylene oxide; water repellants, e.g. waxes, polyvalent metal salts of fatty acids, silicone resins, chromium complexes of fatty acids, N-alkyl amidomethyl pyridinium salts, and melamine-formaldehyde resin condensates with amides from fatty acids. In the treatment of paper the adduct may be present in a wax, starch, casein, elastomer or wet strength resin formulation. The adduct may be mixed in an aqueous or oil type paint formulation and applied to unpainted asbestos siding, wood, metal and masonry. In the treatment of floors and tile surfaces the adducts may be incorporated in a based emulsion or solution. Illustrative articles to be treated are papers, textiles, glass, wood, leather, fur, asbestos, bricks, concrete, metals, ceramics, plastics, painted surfaces, sponges, and plaster. Illustrative papers are carbonizing tissue, wallpaper, asphalt laminates, liner board, cardboard and papers derived from synthetic fibres. Illustrative textiles are those based on cotton, wool, mohair, linen, jute, silk, ramie, sisal kenaf, rayon, acrylics, polyesters, "Saran" (Registered Trade Mark), azylon, nytril, nylon, spandex, vinal, reevon, vinyon, and glass fibres. Detailed examples are given.ALSO:Textiles and leather are made oil-repellent by impreganting with an adduct obtained by reacting an organic isocyanate and a compound containing a sulphonamide group, a perfluoroalkyl terminal group having at least 4 carbon atoms, and a group containing an active hydrogen atom, with or without another compound containing a reactive hydrogen atom which does not contain a perfluoroalkyl group. In examples, compounds made from totylene isocyanate and <FORM:0999795/D1-D2/1> are used to impregnate cloth and suede leather.
GB3173461A 1960-09-02 1961-09-04 Fluorocarbon compounds Expired GB999795A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US5362660A 1960-09-02 1960-09-02

Publications (1)

Publication Number Publication Date
GB999795A true GB999795A (en) 1965-07-28

Family

ID=21985521

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3173461A Expired GB999795A (en) 1960-09-02 1961-09-04 Fluorocarbon compounds

Country Status (4)

Country Link
CH (2) CH410616A (en)
DE (1) DE1468295A1 (en)
GB (1) GB999795A (en)
NL (1) NL139786B (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4525305A (en) * 1982-10-25 1985-06-25 Minnesota Mining And Manufacturing Company Leather with fluorochemical finish
EP0283892A1 (en) * 1987-03-20 1988-09-28 Asahi Glass Company Ltd. Fluorine containing polyurethanes and polyisocyanate compound composition for its preparation
US4834764A (en) * 1984-09-28 1989-05-30 Ciba-Geigy Corporation Process for obtaining wash-and cleaning resistant textile finishes with reactive perfluoroalkyl-containing (co) polymers and/or precondensates and a blocked isocyanate compound
US4835300A (en) * 1982-08-17 1989-05-30 Daikin Kogyo Co., Ltd. Fluorine containing urethane compounds
US5254660A (en) * 1991-11-08 1993-10-19 Bayer Aktiengesellschaft Polyisocyanate solutions useful for impregnating porous inorganic substrates
US5508370A (en) * 1991-10-17 1996-04-16 Bayer Aktiengesellschaft Water-dispersible blocked isocyanates, method of manufacture, and use thereof
US6171983B1 (en) 1991-11-12 2001-01-09 3M Innovative Properties Company Fluroaliphatic dimer acid derivatives and use thereof
WO2002072657A1 (en) * 2001-03-09 2002-09-19 3M Innovative Properties Company Water- and oil-repellency imparting urethane oligomers comprising perfluoroalkyl moieties
ES2377692A1 (en) * 2010-01-25 2012-03-30 Main Style Sl Procedure for obtaining a yute floor for footwear. (Machine-translation by Google Translate, not legally binding)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3607773C2 (en) * 1986-03-08 1995-06-22 Cassella Ag Polyurethanes containing fluoroalkyl ligands, processes for their preparation and their preparations and their use
EP0605105B1 (en) * 1992-12-30 1999-05-06 Imperial Chemical Industries Plc Process for rigid foams
FR2855968B1 (en) 2003-06-13 2012-11-30 Coletica STIMULATION OF THE SYNTHESIS AND ACTIVITY OF A LYSYL OXIDASE-LIKE LOXL ISOFORM TO STIMULATE THE FORMATION OF ELASTIC FIBERS
DE102006046368A1 (en) 2006-09-29 2008-04-03 Construction Research & Technology Gmbh New functionalized polyurethane resins, based on fluoro-modified, stabilized oligo- or polyurethane binder, useful for permanent oil-, water- and dirt-repellent coating of surfaces
DE102009048945A1 (en) 2009-10-10 2011-04-14 Jansen, Bernhard, Dr. Aqueous dispersion of a thermosetting polyurethane composition
CN118006203A (en) * 2024-01-30 2024-05-10 广东裕田霸力科技股份有限公司 Leather product surface treating agent and preparation method thereof

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4835300A (en) * 1982-08-17 1989-05-30 Daikin Kogyo Co., Ltd. Fluorine containing urethane compounds
US4525305A (en) * 1982-10-25 1985-06-25 Minnesota Mining And Manufacturing Company Leather with fluorochemical finish
US4834764A (en) * 1984-09-28 1989-05-30 Ciba-Geigy Corporation Process for obtaining wash-and cleaning resistant textile finishes with reactive perfluoroalkyl-containing (co) polymers and/or precondensates and a blocked isocyanate compound
EP0283892A1 (en) * 1987-03-20 1988-09-28 Asahi Glass Company Ltd. Fluorine containing polyurethanes and polyisocyanate compound composition for its preparation
US5508370A (en) * 1991-10-17 1996-04-16 Bayer Aktiengesellschaft Water-dispersible blocked isocyanates, method of manufacture, and use thereof
US5693737A (en) * 1991-10-17 1997-12-02 Bayer Aktiengesellschaft Water-dispersible blocked isocyanates, method of manufacture, and use thereof
US5254660A (en) * 1991-11-08 1993-10-19 Bayer Aktiengesellschaft Polyisocyanate solutions useful for impregnating porous inorganic substrates
US6171983B1 (en) 1991-11-12 2001-01-09 3M Innovative Properties Company Fluroaliphatic dimer acid derivatives and use thereof
WO2002072657A1 (en) * 2001-03-09 2002-09-19 3M Innovative Properties Company Water- and oil-repellency imparting urethane oligomers comprising perfluoroalkyl moieties
ES2377692A1 (en) * 2010-01-25 2012-03-30 Main Style Sl Procedure for obtaining a yute floor for footwear. (Machine-translation by Google Translate, not legally binding)

Also Published As

Publication number Publication date
NL139786B (en) 1973-09-17
DE1418985A1 (en) 1969-10-02
CH378279A (en) 1964-07-31
CH974061A4 (en) 1964-02-28
DE1468295A1 (en) 1969-05-29
CH410616A (en) 1966-03-31

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