GB1011572A - Phosphorus-containing carboxylic acid amides - Google Patents

Phosphorus-containing carboxylic acid amides

Info

Publication number
GB1011572A
GB1011572A GB17563/63A GB1756363A GB1011572A GB 1011572 A GB1011572 A GB 1011572A GB 17563/63 A GB17563/63 A GB 17563/63A GB 1756363 A GB1756363 A GB 1756363A GB 1011572 A GB1011572 A GB 1011572A
Authority
GB
United Kingdom
Prior art keywords
group
linked
carbon atoms
compounds
alkylene
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
GB17563/63A
Inventor
Sheik Abdul-Cader Zahir
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.)
BASF Schweiz AG
Ciba ARL Ltd
Original Assignee
Ciba AG
Ciba ARL 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
Priority to BE647376D priority Critical patent/BE647376A/xx
Application filed by Ciba AG, Ciba ARL Ltd filed Critical Ciba AG
Priority to GB17563/63A priority patent/GB1011572A/en
Priority to CH297667A priority patent/CH474605A/en
Priority to FR972541A priority patent/FR1395178A/en
Priority to CH553564A priority patent/CH474540A/en
Priority to DE1469281A priority patent/DE1469281C3/en
Publication of GB1011572A publication Critical patent/GB1011572A/en
Priority to US649395A priority patent/US3381062A/en
Priority to US649396A priority patent/US3381063A/en
Priority to US646119A priority patent/US3374292A/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
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • D06M15/43—Amino-aldehyde resins modified by phosphorus compounds
    • D06M15/432—Amino-aldehyde resins modified by phosphorus compounds by phosphonic 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
    • C07F9/06—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
    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
    • C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
    • 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
    • D06M13/288—Phosphonic or phosphonous acids or derivatives thereof

Abstract

Compounds of the general formula (I): <FORM:1011572/C3/1> where R represents hydrogen, allyl, or an alkyl group of up to six carbon atoms; n is either 1, when X represents hydrogen, methyl or a -CH2CONHCH2OR group, or zero, when X represents a -CH2CONHCH2OR group; and R1 and R2 either each represent the same or different alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxyalkyl, alkoxyalkenyl, aryl, alkoxyaryl or alkylene residues, which may be substituted by one or more chlorine and/or bromine atoms, the terminal valencies of such alkylene residues being linked to a group of Formula II: <FORM:1011572/C3/2> the free valency of which, if only one of R1 and R2 is alkylene, is linked to a further monovalent R1 or R2 residue, or R1 and R2 together represent a polymethylene chain containing from two to six carbon atoms, which may be linked to a second polymethylene chain containing two to six carbon atoms, via a spirocarbon, which polymethylene chains may be substituted by one or more chlorine and/or bromine atoms and/or methyl groups, the terminal valencies of the second polymethylene chain, if such be present, being linked to a group of Formula (II), and in which at least one of R, R1 or R2 is allyl may be polymerized using a free radical catalyst. The polymers may be used in flame-proofing cellulosic materials. In Example (XVII), N - hydroxymethyl - 3-(diallyloxyphosphinyl) propionamide is polymerized using ammonium persulphate as catalyst. Specifications 693,742 and 695,782 are referred to.ALSO:The invention comprises compounds of the general Formula I <FORM:1011572/C2/1> where R represents hydrogen, allyl, or an alkyl group of up to six carbon atoms; n is either 1, when X represents hydrogen, methyl or a -CH2CONHCH2OR group, or zero, when X represents a -CH2CONHCH2OR group; and R1 and R2 either each represent the same or different alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxyalkyl, alkoxyalkenyl, aryl, alkoxyaryl or alkylene residues, which may be substituted by one or more chlorine and/or bromine atoms, the terminal valencies of such alkylene residues being linked to a group of Formula II <FORM:1011572/C2/2> the free valency of which, if, only one of R1 and R2 is alkylene, is linked to a further monovalent R1 or R2 residue, or R1 and R2 together represent a polymethylene chain containing from two to six carbon atoms, which may be linked to a second polymethylene chain containing two to six carbon atoms, via a spiro-carbon, which polymethylene chains may be substituted by one or more chlorine and/or bromine atoms and/or methyl groups, the terminal valencies of the second polymethylene chain, if such be present, being linked to a group of Formula II. Preparative methods include: (1) reacting corresponding -CHXCONH2 compounds with formaldehyde or a source thereof to give products in which R=H; (2) etherifying compounds in which R=H by reaction with an alcohol in the presence of acid; (3) reacting compounds of type (CH2=)n-CX1=CONHCH2OR, where X1 is as X except that when n=O, X1 is =CHCONHCH2OR, with an appropriate secondary phosphite; (4) introduction of halogen, e.g. by reacting 3-(diallyloxyphosphinyl)-propionamide with a polyhalomethane (e.g. trichloro-bromo-methane) in the presence of a free radical catalyst and then hydroxymethylating. A number of starting materials of type <FORM:1011572/C2/3> including compounds illustrating the alkylene, polymethylene chain and spiro aspects of R1 and R2, are prepared by reacting (CH2=)2-CX1-CONH2 and (R1O)(R2O)P(O)H or by the action of ammonia on esters of (R1O)(R2O)P(O)(CH2)nCH(COOH)2. n-Butyl ethyl phosphite and secondary phosphites derived from butane-1,3-diol/cyclic phosphite, cyclohexanol, neopentyl glycol (cyclic phosphite) pentaerythritol (cyclic diphosphite) and ethylene glycol (diphosphite) are prepared by means of PCl3 or transesterification. Dimethyl - 2 - (diethoxyphosphinylmethyl)-succinate and di-n-propyl - 2 - (diethoxy - phosphinyl) succinate are prepared from diethyl phosphite and dimethyl itaconate and di-n-propyl maleate respectively. N - (Allyloxymethyl) acrylamide is prepared from acrylamide, paraformaldehyde and allyl alcohol. Specifications 693,742 and 695,782 are referred to.ALSO:Compounds of the general formula I <FORM:1011572/D1-D2/1> where R represents hydrogen, allyl, or an alkyl group of up to six carbon atoms; n is either 1, when X represents hydrogen, methyl or a <FORM:1011572/D1-D2/2> group, or zero, when X represents a -CH2CONCH2 or group; and R1 and R2 either each represent the same or different alkyl, alkenl, cycloalkyl, cycloalkenyl, alkoxyalkyl, alkoxyalkenyl, aryl, alkoxyaryl or alkylene residues, which may be substituted by one or more chlorine and/or bromine atoms, the terminal valencies of such alkylene residues being linked to a group of formula II: <FORM:1011572/D1-D2/3> the free valency of which, if only one of R1 and R2 is alkylene, is linked to a further monovalent R1 or R2 residue, or R1 and R2 together represent a polymethylene chain containing from two to six carbon atoms, which may be linked to a second polemethylene chain containing two to six carbon atoms, via a spiro-carbon, which polymethylene chains may be substituted by one or more chlorine and/or chromine atoms and/or methyl groups, the terminal valencies of the second polymethylene chain, if such be present, being linked to a group of formula II, or polymer of uch compounds in which at least one of R, R1 and R2 is alkyl are used in flameproofing cellulosic materials. If only one -CONHCH2OR group is present in the compound, an aminoplast is also necessary, but this is optional if there are two or more -CONHCH2Or groups. A latent acid catalyst is preferably present. Suitable aminoplast include urea-formaldehyde, ethyleneurea-formaldehyde, melamine-formaldehyde and etherified melamine-formaldehyde resins. Cellulosic materials treated in examples are cotton, viscose and paper. Other substancess present in examples are Na1CO3, MgCl2, NH4H2PO4, mer emulsion, a polyethylene wax emulsion and a wetting agent derived from ethylene oxide. Specifications 693,742 and 695,782 are referred to.
GB17563/63A 1963-05-03 1963-05-03 Phosphorus-containing carboxylic acid amides Expired GB1011572A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
BE647376D BE647376A (en) 1963-05-03
GB17563/63A GB1011572A (en) 1963-05-03 1963-05-03 Phosphorus-containing carboxylic acid amides
CH297667A CH474605A (en) 1963-05-03 1964-04-28 Use of phosphonamides to make cellulose-containing textile material flame-resistant
FR972541A FR1395178A (en) 1963-05-03 1964-04-28 New compounds containing phosphorus
CH553564A CH474540A (en) 1963-05-03 1964-04-28 Process for the preparation of phosphonamides
DE1469281A DE1469281C3 (en) 1963-05-03 1964-04-30 Phosphonocarboxamides, processes for their preparation and their use for flame retardancy
US649395A US3381062A (en) 1963-05-03 1967-05-11 Cyclic diphosphono-carboxylic amides
US649396A US3381063A (en) 1963-05-03 1967-05-11 Cyclic phosphono-carboxylic amides
US646119A US3374292A (en) 1963-05-03 1967-06-14 Phosphono carboxamides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB17563/63A GB1011572A (en) 1963-05-03 1963-05-03 Phosphorus-containing carboxylic acid amides

Publications (1)

Publication Number Publication Date
GB1011572A true GB1011572A (en) 1965-12-01

Family

ID=10097384

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17563/63A Expired GB1011572A (en) 1963-05-03 1963-05-03 Phosphorus-containing carboxylic acid amides

Country Status (5)

Country Link
US (1) US3374292A (en)
BE (1) BE647376A (en)
CH (2) CH474540A (en)
DE (1) DE1469281C3 (en)
GB (1) GB1011572A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0256191A1 (en) * 1986-08-20 1988-02-24 Dainippon Ink And Chemicals, Inc. Fire retardant for woody materials
US4839099A (en) * 1985-02-27 1989-06-13 Dainippon Ink And Chemicals, Inc. Fire-retardant for woody materials
AU642465B2 (en) * 1990-03-01 1993-10-21 Albright & Wilson Uk Limited Flame retardant composition and method of use

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH625070A4 (en) * 1970-04-27 1971-12-15
US3699192A (en) * 1970-10-20 1972-10-17 U S Oil Co Inc Phosphonium compounds
US3765837A (en) * 1971-09-03 1973-10-16 Burlington Industries Inc Flame retardant finish for polyester/cotton blends
DE2253663A1 (en) * 1972-11-02 1974-05-16 Hoechst Ag PHOSPHORUS COMPOUNDS CONTAINING AMIDE GROUPS AND THEIR USE AS FLAME PROTECTION AGENTS
US3903337A (en) * 1974-04-04 1975-09-02 Mitsui Toatsu Chemicals Method for processing cellulose containing material to impart flame resistance
US4017462A (en) * 1974-08-22 1977-04-12 The United States Of America As Represented By The Secretary Of Agriculture Treatment of organic textiles with adduct polymers and phenols
US4007318A (en) * 1975-05-21 1977-02-08 General Electric Company Phosphorylated polystyrene and method for forming same
US4162279A (en) * 1977-09-28 1979-07-24 Stauffer Chemical Company Phosphonoxycarboxamides
US4577013A (en) * 1983-12-22 1986-03-18 Ciba-Geigy Corporation Ionically modified cellulose material, its preparation and its use
IL98728A0 (en) * 1990-08-03 1992-07-15 Pfersee Chem Fab Flameproofing compositions containing phosphono compounds and organic acids
EP1935935A1 (en) * 2006-12-20 2008-06-25 Huntsman Textile Effects (Germany) GmbH Compound for treating fibre materials
EP2133461A1 (en) 2008-06-12 2009-12-16 Huntsman Textile Effects (Germany) GmbH Compound for treating fibrous material, in particular by the method of extraction

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4839099A (en) * 1985-02-27 1989-06-13 Dainippon Ink And Chemicals, Inc. Fire-retardant for woody materials
EP0256191A1 (en) * 1986-08-20 1988-02-24 Dainippon Ink And Chemicals, Inc. Fire retardant for woody materials
AU642465B2 (en) * 1990-03-01 1993-10-21 Albright & Wilson Uk Limited Flame retardant composition and method of use

Also Published As

Publication number Publication date
CH297667A4 (en) 1969-03-14
BE647376A (en)
DE1469281A1 (en) 1969-05-08
CH474605A (en) 1969-08-15
DE1469281B2 (en) 1973-04-26
US3374292A (en) 1968-03-19
DE1469281C3 (en) 1973-11-22
CH474540A (en) 1969-06-30

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