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GB939902A - Process for imparting oil-repellency to solid materials and materials thus produced - Google Patents

Process for imparting oil-repellency to solid materials and materials thus produced

Info

Publication number
GB939902A
GB939902A GB31993/61A GB3199361A GB939902A GB 939902 A GB939902 A GB 939902A GB 31993/61 A GB31993/61 A GB 31993/61A GB 3199361 A GB3199361 A GB 3199361A GB 939902 A GB939902 A GB 939902A
Authority
GB
United Kingdom
Prior art keywords
water
integer
phosphate
materials
acetate
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
GB31993/61A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and 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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB939902A publication Critical patent/GB939902A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/80—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone of only ceramics
    • C04B41/81—Coating or impregnation
    • C04B41/82—Coating or impregnation with organic materials
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
    • C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
    • C04B41/466—Halogenated compounds, e.g. perfluor-compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/004—Surface-active compounds containing F
    • C11D1/006—Surface-active compounds containing fluorine and phosphorus
    • 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
    • D06M13/282—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 phosphorus
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • 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
    • D06M13/282—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 phosphorus
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • D06M13/298—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof 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
    • 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
    • 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
    • D21H17/10—Phosphorus-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)
  • Organic Chemistry (AREA)
  • Ceramic Engineering (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Paper (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Polyfluoroalkyl phosphates of the formula <FORM:0939902/IV(a)/1> in which m is an integer of 3-12, y is 1 or 2, r is an integer of 2-16 and Z is a hydrogen atom or water solubilizing cation, e.g. Na, K, Li, ammonium, diethanol ammonium, triethanolammonium or morpholinium, are prepared by heating together 1-iodopolyfluoroalkanes, e.g. 1-iodopentadecafluoroheptane, and omega-alkenyl acetates, e.g. vinyl acetate, 4-pentenyl acetate and 10-undecenyl acetate, in the presence of 2,21-azodiisobutyronitrile, reacting the iodofluoroalkyl acetates thus produced with a mixture comprising zinc dust and concentrated hydrochloric acid in ethanol and treating the product with a solution of potassium hydroxide in ethanol to produce fluoroalcohols having the formula F(CF2)m (CH2)rOH which are then reacted with POCl3 in benzene in presence of pyridine to yield the mono or dichlorophosphates which are subsequently hydrolysed with pyridine and water. Specifications 475,131 and 475,132 are referred to.ALSO:Water in soluble solid materials, e.g. textile fibres such as cotton, viscose rayon, cellulose acetate (including triacetate), wool, silk, nylon, acrylic and polyester fibres, leather, paper, plastic sheeting, wood and ceramic clays, are rendered oil repellent and may be rendered water repellent by treating them with an aqueous bath containing a water-soluble polyfluoroalkyl phosphate of the formulae <f1> or <f2> in which m is an integer of 3-12, n is an integer of 6-12, y is 1 or 2, r is an integer of 2-16 and Z is a hydrogen atom or a water-solubilizing cation, e.g. Na, K, Li, ammonium, diethanolammonium, triethanolammonium or morpholinium, and drying them to form in intimate contact with the material an evenly distributed deposit of the polyfluoroallyl phosphate. The polyfluoro alkyl phosphates may be applied to the materials treated from a purely aqueous bath or from an aquenous bath containing acetone, alcohol or any other water miscible, volatile adjuvant by padding or exhaustion. Before, simultaneously with or after treatment with the polyfluoroalkyl phosphate the material may be treated with an aqueous bath comprising a water-soluble linear polymer containing cationic N- atoms, e.g. polymers or copolymers of quaternary or acid salts of a dialkylamino alcohol and acrylic or methacrylic acid, urea-formaldehyde resins, melamine-formaldehyde resins, quaternized or acid salts of polymerized ethylene imine and cationically modified nitrogen containing starches, to deposit 0,05-10% by weight of polymer on the material. The polyfluoro alkyl phosphate and the linear polymer containing cationic N- atoms may be added to aqueous paper pulp prior to sheet formation. Specifications 475,131 and 475,132 are referred to.
GB31993/61A 1960-09-06 1961-09-06 Process for imparting oil-repellency to solid materials and materials thus produced Expired GB939902A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US53884A US3112241A (en) 1960-09-06 1960-09-06 Process of imparting oil-repellency to solid materials, and materials thus produced
US53885A US3096207A (en) 1960-09-06 1960-09-06 Process of imparting oil-repellency to solid materials

Publications (1)

Publication Number Publication Date
GB939902A true GB939902A (en) 1963-10-16

Family

ID=26732342

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31993/61A Expired GB939902A (en) 1960-09-06 1961-09-06 Process for imparting oil-repellency to solid materials and materials thus produced

Country Status (5)

Country Link
US (2) US3112241A (en)
DE (1) DE1260059B (en)
FI (1) FI40279B (en)
FR (1) FR1305612A (en)
GB (1) GB939902A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2951474A1 (en) * 1978-12-20 1980-07-10 Minnesota Mining & Mfg ANTISTATIC MIXTURE AND THEIR USE
US11214763B2 (en) 2018-01-26 2022-01-04 Ecolab Usa Inc. Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a carrier
US11377628B2 (en) 2018-01-26 2022-07-05 Ecolab Usa Inc. Solidifying liquid anionic surfactants
US11655436B2 (en) 2018-01-26 2023-05-23 Ecolab Usa Inc. Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a binder and optional carrier

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3188340A (en) * 1961-12-08 1965-06-08 Du Pont Polyfluoro alkanamidoalkyl phosphates
US3431140A (en) * 1964-09-29 1969-03-04 American Cyanamid Co Oil and water repellent textiles
US3318240A (en) * 1966-02-21 1967-05-09 Beveridge Paper Company Matrix mat for plastic printing plate
US3468697A (en) * 1966-03-02 1969-09-23 Colgate Palmolive Co Method of treating textile articles which are usually laundered
US3754979A (en) * 1970-05-01 1973-08-28 Du Pont Line resolution in screen printing
US4145303A (en) * 1971-03-08 1979-03-20 Minnesota Mining And Manufacturing Company Cleaning and treating compositions
US3953283A (en) * 1972-10-05 1976-04-27 Continental Can Company, Inc. Paperboard having improved oil resistance
JPS5545680B2 (en) * 1972-11-11 1980-11-19
US4097297A (en) * 1975-08-07 1978-06-27 E. I. Du Pont De Nemours And Company Barrier coatings
US4118235A (en) * 1975-09-18 1978-10-03 Daikin Kogyo Co., Ltd. Mold release agent
US4064067A (en) * 1976-04-26 1977-12-20 E. I. Du Pont De Nemours And Company Fluorosurfactant leveling agent
US4380565A (en) * 1982-01-08 1983-04-19 Champion International Corporation Color preservation of wax-coated paperboard
JPS63267792A (en) * 1987-04-22 1988-11-04 Daikin Ind Ltd Method for producing phosphoric acid di(fluoroalkyl group-containing group-substituted alkyl) salt
EP0462063A1 (en) * 1990-06-13 1991-12-18 Ciba-Geigy Ag Fluorinated paper sizes
US5120364A (en) * 1990-10-10 1992-06-09 Ciba-Geigy Corporation Heteroatom containing perfluoroalkyl terminated neopentyl sulfates and salts thereof
JP3030863B2 (en) * 1990-12-25 2000-04-10 ダイキン工業株式会社 Leather modifying agent, leather modifying method and modified tanned leather
ES2185626T3 (en) * 1992-01-27 2003-05-01 Daikin Ind Ltd USE OF A TREATMENT AGENT FOR FIBER PRODUCTS, PROCESSING PROCESSING OF FIBER PRODUCTS TREATED ACCORDING TO THIS PROCEDURE.
CA2146726A1 (en) 1994-05-18 1995-11-19 Susan S. Harrison Fluorine-containing phosphates
IT1269886B (en) * 1994-06-14 1997-04-15 Ausimont Spa PROCESS FOR SURFACE TREATMENT OF CELLULOSE, METAL, GLASS, OR CEMENT, MARBLE, GRANITE AND SIMILAR MATERIALS
US5525261A (en) * 1994-10-18 1996-06-11 Henkel Corporation Anti-static composition and method of making the same
US6191389B1 (en) * 2000-03-31 2001-02-20 General Electric Company Grease resistant oven grille
CA2554293A1 (en) 2004-01-30 2005-08-18 Great Lakes Chemical Corporation Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers
KR20060132888A (en) * 2004-01-30 2006-12-22 그레이트 레이크스 케미칼 코퍼레이션 Compositions, Halogenated Compositions, Chemical Preparations and Telomerization Methods
CA2553930A1 (en) * 2004-01-30 2005-08-18 Great Lakes Chemical Corporation Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers
KR20070101402A (en) * 2004-01-30 2007-10-16 그레이트 레이크스 케미칼 코퍼레이션 Fluorinated compounds
EP1907343A2 (en) * 2005-07-28 2008-04-09 Great Lakes Chemical Corporation Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers
US20070027349A1 (en) * 2005-07-28 2007-02-01 Stephan Brandstadter Halogenated Compositions
US20080076892A1 (en) * 2006-08-03 2008-03-27 Bruno Ameduri Telomer compositions and production processes
US8318656B2 (en) 2007-07-03 2012-11-27 E. I. Du Pont De Nemours And Company Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers
US7989566B2 (en) * 2008-01-22 2011-08-02 Dupont Performance Elastomers Llc Process for producing fluoropolymers
US8695810B2 (en) * 2010-06-10 2014-04-15 University of Pittsburgh—of the Commonwealth System of Higher Education Superoleophobic and superhydrophilic fabric filters for rapid water-oil separation
US20130210976A1 (en) * 2012-02-13 2013-08-15 E. I. Du Pont De Nemours And Company Fluorinated phosphates as surface active agents

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2597702A (en) * 1950-06-29 1952-05-20 Du Pont Fluoroalkylphosphoric compounds
US2920979A (en) * 1956-01-13 1960-01-12 Minnesota Mining & Mfg Paper sized with fluorocarbon agents on one side and coated on the opposite side with thermoplastic materials
US2955958A (en) * 1956-03-05 1960-10-11 Nathan J Brown Process of treating woven textile fabric with a vinyl chloride polymer
US2957796A (en) * 1957-05-01 1960-10-25 Michigan Res Lab Inc Grease-proof paper
US2913427A (en) * 1957-06-25 1959-11-17 Stamford Chemical Company Water repellent composition and article coated therewith
US2917409A (en) * 1958-12-31 1959-12-15 Du Pont Fluorine compounds, process of preparing said compounds, and process of rendering textile oil repellent

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2951474A1 (en) * 1978-12-20 1980-07-10 Minnesota Mining & Mfg ANTISTATIC MIXTURE AND THEIR USE
US11214763B2 (en) 2018-01-26 2022-01-04 Ecolab Usa Inc. Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a carrier
US11377628B2 (en) 2018-01-26 2022-07-05 Ecolab Usa Inc. Solidifying liquid anionic surfactants
US11655436B2 (en) 2018-01-26 2023-05-23 Ecolab Usa Inc. Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a binder and optional carrier
US11834628B2 (en) 2018-01-26 2023-12-05 Ecolab Usa Inc. Solidifying liquid anionic surfactants
US11976255B2 (en) 2018-01-26 2024-05-07 Ecolab Usa Inc. Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a binder and optional carrier
US12006488B2 (en) 2018-01-26 2024-06-11 Ecolab Usa Inc. Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a carrier
US12359147B2 (en) 2018-01-26 2025-07-15 Ecolab Usa Inc. Solidifying liquid anionic surfactants

Also Published As

Publication number Publication date
US3112241A (en) 1963-11-26
US3096207A (en) 1963-07-02
FI40279B (en) 1968-09-02
DE1260059B (en) 1968-02-01
FR1305612A (en) 1962-10-05

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