GB1088672A - Reactions of polymeric materials with vinyl phosphonium compounds - Google Patents

Reactions of polymeric materials with vinyl phosphonium compounds

Info

Publication number
GB1088672A
GB1088672A GB3897163A GB3897163A GB1088672A GB 1088672 A GB1088672 A GB 1088672A GB 3897163 A GB3897163 A GB 3897163A GB 3897163 A GB3897163 A GB 3897163A GB 1088672 A GB1088672 A GB 1088672A
Authority
GB
United Kingdom
Prior art keywords
vinyl
phosphonium
group
iodide
cellulosic
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
GB3897163A
Inventor
Leslie Mackenzie Valentine
Henry Fletcher
John Holden Lupton
Ronald Cowling
James Albert Moyse
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.)
Imperial Chemical Industries Ltd
TOOTAL Ltd
Original Assignee
Imperial Chemical Industries Ltd
TOOTAL 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
Application filed by Imperial Chemical Industries Ltd, TOOTAL Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB3897163A priority Critical patent/GB1088672A/en
Priority to BE653936A priority patent/BE653936A/xx
Priority to NL6411531A priority patent/NL6411531A/xx
Priority to FR990220A priority patent/FR1414979A/en
Publication of GB1088672A publication Critical patent/GB1088672A/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
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/0036—Dyeing and sizing in one process
    • 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 System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • 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
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/01—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with hydrogen, water or heavy water; with hydrides of metals or complexes thereof; with boranes, diboranes, silanes, disilanes, phosphines, diphosphines, stibines, distibines, arsines, or diarsines or complexes thereof
    • D06M11/05—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with hydrogen, water or heavy water; with hydrides of metals or complexes thereof; with boranes, diboranes, silanes, disilanes, phosphines, diphosphines, stibines, distibines, arsines, or diarsines or complexes thereof with water, e.g. steam; with heavy water
    • 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
    • D06M13/313—Unsaturated compounds containing phosphorus atoms, e.g. vinylphosphonium compounds
    • 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
    • D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03—Polysaccharides or derivatives thereof
    • D06M15/05—Cellulose or derivatives thereof
    • D06M15/09—Cellulose ethers
    • 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
    • D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03—Polysaccharides or derivatives thereof
    • D06M15/11—Starch or derivatives 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/15—Proteins or derivatives 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
    • 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
    • D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
    • D06M15/3564—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing phosphorus

Abstract

Cellulosic or proteinaceous material such as wool, glue, gelatin or leather is reacted in the presence of an alkaline catalyst with a vinyl phosphonium compound or with a substance which forms or liberates a vinyl phosphonium compound under the reaction conditions. The cellulosic or proteinaceous material contains at least one reactive -OH, -NH- or -SH group in the molecule and may be paper, wood, cellulosic film, cellulose ethers and esters, wool, glue, gelatin or leather. The vinyl phosphonium compound suitably has the formula <FORM:1088672/C3/1> wherein R1 is a vinyl or substituted vinyl group, R2, R3 and R4 each represents R1 or a grou R which is alkyl, substituted alkyl, alicyclic, aralkyl, aryl or heterocyclic or alkenyl other than R1 and X- represents the anion of an acid or a hydroxyl anion. Substances which form or liberate vinyl phosphonium compounds are especially the esters of b -hydroxyalkyl phosphonium compounds of the formula <FORM:1088672/C3/2> wherein R5, R6 and R7 independently represent hydrogen or an alkyl group of 1 to 3 carbon atoms and R8, R9 and R10 each represent a group of the formula -CHR5CR6R7OH or the group R. The cellulosic or proteinaceous materials are preferably in the form of a textile material (see Division D1)ALSO:Triethyl acetoxyethyl phosphonium chloride or iodide may be prepared by first preparing triethyl phosphine by reaction of phosphorus trichloride with a reaction product of ethyl bromide and magnesium turnings in diethyl ether and then reacting the triethyl phosphine with b -chloro-(or iodo-)ethyl acetate. Similarly tris-(b -cyanoethyl) b -acetoxyethyl phosphonium iodide may be prepared by reacting tris-(b -cyanoethyl) phosphine with b -iodoethyl acetate. On heating the phosphonium compounds with an alkaline catalyst they form the corresponding vinyl phosphonium compounds.ALSO:Cellulosic or proteinaceous textile materials may have various properties improved, e.g. crease-resistance, swelling resistance and shrink resistance, by treatment with a vinyl phosphonium compound or with a substance which forms or liberates a vinyl phosphonium compound. Alternatively a textile material may be treated with a cellulosic or proteinaceous polymer and a vinyl phosphonium compound. The vinyl phosphonium compound suitably has the formula: <FORM:1088672/D1-D2/1> wherein R1 represents a vinyl or substituted vinyl group, R2, R3 and R4 represent the group R1 or a group R which represents an alkyl, substituted alkyl, alicyclic, aralkyl, aryl or heterocyclic group or an alkenyl group other than R1 and X- represents the anion of an acid or a hydroxyl anion. Substances which form or liberate the vinyl phosphonium compounds may be the esters of b -hydroxyalkyl phosphonium compounds. A combined treatment wherein, the vinyl phosphonium compound is used in conjunction with or independently of a synthetic thermosetting resin, resin precursor or formaldehyde may also be used. The vinyl phosphonium compound is suitably applied in the form of an aqueous solution. Examples describe the treatment of mercerised cotton poplin fabric with (1) methyltrivinylphosphonium iodide, (2) a mixture of methyltrivinylphosphonium iodide and dimethylol ethylene urea (5) triethyl acetoxyethyl phosphonium chloride (8) methyltrivinyl phosphonium iodide and 1,3-dimethylol hexahydropyrimidone-2, viscose rayon staple fibre fabric with (3) methyltrivinyl phosphonium iodide, cotton cloth with (6) triethyl acetoxyethyl phosphonium iodide and (7) tris-(b -cyanoethyl) b -acetoxyethyl phosphonium iodide and a polyethylene terephthalate fibre fabric with (4) hydroxyethylated cellulose and methyltrivinylphosphonium iodide.
GB3897163A 1963-10-03 1963-10-03 Reactions of polymeric materials with vinyl phosphonium compounds Expired GB1088672A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB3897163A GB1088672A (en) 1963-10-03 1963-10-03 Reactions of polymeric materials with vinyl phosphonium compounds
BE653936A BE653936A (en) 1963-10-03 1964-10-02
NL6411531A NL6411531A (en) 1963-10-03 1964-10-02
FR990220A FR1414979A (en) 1963-10-03 1964-10-02 A method of reacting a polymeric material and a vinyl phosphonium compound

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3897163A GB1088672A (en) 1963-10-03 1963-10-03 Reactions of polymeric materials with vinyl phosphonium compounds

Publications (1)

Publication Number Publication Date
GB1088672A true GB1088672A (en) 1967-10-25

Family

ID=10406826

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3897163A Expired GB1088672A (en) 1963-10-03 1963-10-03 Reactions of polymeric materials with vinyl phosphonium compounds

Country Status (3)

Country Link
BE (1) BE653936A (en)
GB (1) GB1088672A (en)
NL (1) NL6411531A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4982793A (en) * 1989-03-10 1991-01-08 Halliburton Company Crosslinkable cellulose derivatives
US5067565A (en) * 1989-03-10 1991-11-26 Halliburton Company Crosslinkable cellulose derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4982793A (en) * 1989-03-10 1991-01-08 Halliburton Company Crosslinkable cellulose derivatives
US5067565A (en) * 1989-03-10 1991-11-26 Halliburton Company Crosslinkable cellulose derivatives

Also Published As

Publication number Publication date
NL6411531A (en) 1965-04-05
BE653936A (en) 1965-04-02

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