GB1122404A - Polyfluoroalkyl derivatives of phosphorous acids - Google Patents

Polyfluoroalkyl derivatives of phosphorous acids

Info

Publication number
GB1122404A
GB1122404A GB32597/65A GB3259765A GB1122404A GB 1122404 A GB1122404 A GB 1122404A GB 32597/65 A GB32597/65 A GB 32597/65A GB 3259765 A GB3259765 A GB 3259765A GB 1122404 A GB1122404 A GB 1122404A
Authority
GB
United Kingdom
Prior art keywords
radical
compounds
epoxyalkoxy
hydrogen
halogen
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
GB32597/65A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of GB1122404A publication Critical patent/GB1122404A/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
    • 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
    • D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
    • 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
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/3804—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • 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
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • 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
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/42—Halides thereof
    • 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
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/44—Amides thereof
    • C07F9/4403—Amides thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4407—Amides of acyclic saturated acids which can have further substituents on alkyl
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
    • C08G59/304—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing phosphorus
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4071—Curing agents not provided for by the groups C08G59/42 - C08G59/66 phosphorus containing compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/061—Metal salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/063—Ammonium or amine salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Textile Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)

Abstract

A lubricating or hydraulic oil composition comprises a compound of the formula <FORM:1122404/C4-C5/1> and <FORM:1122404/C4-C5/2> wherein Rf is a perfluoroalkyl radical of more than 5 carbon atoms, which may have a chlorine or hydrogen atom replacing a fluorine atom in the o -position, X is hydrogen or an alkyl radical, Y is alkoxy, aralkoxy, aryloxy, epoxyalkoxy, an amine radical, halogen, -SH or -OH, n is 2-7 and Q is oxygen or sulphur. Certain of the compounds may themselves be used as lubricants, e.g. for metal surfaces.ALSO:Polyfluoroalkyl phosphorus compounds of the formulae <FORM:1122404/C2/1> <FORM:1122404/C2/2> wherein Rf is a perfluoroalkyl radical of more than 5 carbon atoms which may have a chlorine or hydrogen atom replacing a fluorine atom in the o -position, X is hydrogen or an alkyl radical, Y is alkoxy, aralkoxy, aryloxy, epoxyalkoxy, an amine radical, halogen -SH or -OH, n is 2 to 7 and Q is oxygen or sulphur, may be prepared by (a) reacting a trialkyl phosphite with a fluorohaloalkane which has no fluorine in the a - and b -positions to the reactive halogen, (b) reacting ionically or by a radical mechanism an alkyl phosphonic, thiophosphonic, phosphinic or thiophosphinic acid with a fluoro-olefin or fluorohalo-olefin which has no fluorine on the double bond, or (c) reacting thermally or by a radical mechanism a chlorofluoroiodoalkane or fluoroiodoalkane with an unsaturated alkyl phosphonic, thiophosphonic, phosphinic or thiophosphinic acid or a derivative thereof and deiodinating the resulting product. Process (a) is suitably effected by mixing the components in molar proportions and heating to 120-170 DEG C. under a nitrogen atmosphere. Reaction (b) is suitably effected by initiating the reaction with ultraviolet irradiation, azoisobutyronitrile at 60-70 DEG C. or with peroxide initiators; sodium alcoholate may also be employed to catalyze the reaction and in the case of alkyl thiophosphonic and thiophosphinic acids being used as starting materials, heating of the reaction mixture is sufficient. Reaction (c) may be effected by heating the reactants at a temperature greater than 150 DEG C. or with radical-forming irradiation or a radicalforming catalyst; the resulting compounds are subsequently de-iodinated, e.g. by treatment with zinc turnings in HCl. The acids may be converted to glycidyl esters by treatment with epichlorhydrin and subsequent elimination of HCl in the presence of an HCl acceptor. Ethyleneimine diamides may be prepared by reacting the fluoralkyl phosphinic acid dichlorides with a stoichiometric amount of ethyleneimine in pyridine-ether solution.ALSO:Substrates, e.g. varnished layers, metals, plastics and wood may be treated with a composition comprising a compound of the formula:- <FORM:1122404/B1-B2/1> and <FORM:1122404/B1-B2/2> wherein R1 is a perfluoroalkyl radical of more than 5 carbon atoms which may have a chlorine or hydrogen atom replacing a fluorine atom in the o -position, x is hydrogen or an alkyl radical, Y is alkoxy, aralkoxy, aryloxy, epoxyalkoxy, an amine radical, halogen, -SH or -OH, n is 2-7 and Q is oxygen or sulphur. The composition applied may be cured by heating for a short period at 120 DEG C. Preferred compounds for use are those which carry polymerisable ester and amide groups, e.g. compounds of the above formula where the group Y is an ethyleneimine or epoxyalkoxy group. In specific examples a glycidyl ester precondensate mixture of one of the above compounds is (a) added to a varnish preparation into which two degreased iron plates are dipped and subsequently dried at 25 DEG C for 30 hours and at 150 DEG C for 10 minutes respectively, and (b) dissolved in trichloroethylene mixed with diethylenetriamine and sprayed onto an epoxide resin varnish layer which is subsequently allowed to harden; this same solution is also used to treat a Cellophane (Trade Mark) film, a polyethylene film and a polyester textile fabric.ALSO:Textiles, paper and leather are impregnated with a compound of the formula:- <FORM:1122404/D1-D2/1> and <FORM:1122404/D1-D2/2> wherein Rf is a perfluoroalkyl radical of more than 5 carbon atoms which may have a chlorine or hydrogen atom replacing a fluorine atom in the o -position, x is hydrogen or an alkyl radical, Y is alkoxy, aralkoxy, aryloxy, epoxyalkoxy, an amine radical, halogen, -SH or -OH, n is 2 to 7 and Q is oxygen or sulphur. The impregnating agent on the substrate may be cured by heating for a short period at 120 DEG C. Preferred compounds are those which carry polymerisable ester and amide groups, e.g. compounds of the above formula where the group Y is an ethyleneimine or an epoxyalkoxy group, and such derivatives are suitably applied in the form of very dilute aqueous solutions or emulsions in trichloroethylene. In specific examples, suede, cotton cloth a polyester textile fabric and filter paper are treated.
GB32597/65A 1964-07-31 1965-07-30 Polyfluoroalkyl derivatives of phosphorous acids Expired GB1122404A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB0077905 1964-07-31

Publications (1)

Publication Number Publication Date
GB1122404A true GB1122404A (en) 1968-08-07

Family

ID=6979649

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32597/65A Expired GB1122404A (en) 1964-07-31 1965-07-30 Polyfluoroalkyl derivatives of phosphorous acids

Country Status (6)

Country Link
AT (5) AT270675B (en)
BE (1) BE667479A (en)
CH (1) CH449573A (en)
FR (1) FR1454535A (en)
GB (1) GB1122404A (en)
NL (1) NL6509545A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4052485A (en) * 1971-02-25 1977-10-04 Ciba-Geigy Corporation Perfluoro compounds containing phosphorus
EP1616713A2 (en) * 2004-07-16 2006-01-18 Heidelberger Druckmaschinen Aktiengesellschaft Reusable printing plate
CN112011657A (en) * 2019-05-31 2020-12-01 劳力士有限公司 Composition for impregnating substrates, in particular watch straps

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2110767C3 (en) * 1971-03-06 1974-02-14 Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt Perfluoroalkyl phosphorus compounds
FR2616150B1 (en) * 1987-06-05 1990-11-23 Atochem FLUOROPHOSPHONIC COMPOUNDS AND PROCESS FOR THEIR PREPARATION

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4052485A (en) * 1971-02-25 1977-10-04 Ciba-Geigy Corporation Perfluoro compounds containing phosphorus
EP1616713A2 (en) * 2004-07-16 2006-01-18 Heidelberger Druckmaschinen Aktiengesellschaft Reusable printing plate
EP1616713A3 (en) * 2004-07-16 2006-04-05 Heidelberger Druckmaschinen Aktiengesellschaft Reusable printing plate
CN112011657A (en) * 2019-05-31 2020-12-01 劳力士有限公司 Composition for impregnating substrates, in particular watch straps

Also Published As

Publication number Publication date
AT264544B (en) 1968-09-10
FR1454535A (en) 1966-02-11
AT270675B (en) 1969-05-12
AT279534B (en) 1970-03-10
NL6509545A (en) 1966-02-01
CH449573A (en) 1968-04-11
AT266863B (en) 1968-12-10
CH1052165A4 (en) 1967-09-30
BE667479A (en) 1965-11-16
AT276605B (en) 1969-11-25

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