Patent GB-1074237-A (GB)
Title: Polymerisable monomers containing phosphorus and process for their manufacture
IPC: C08F283/01
Filed: 1964-09-10
Abstract: The invention comprises compounds of the general formula <FORM:1074237/C2/1> where A represents <FORM:1074237/C2/2> -COOH, -CONH2 or -CONHCH2OR111, R represents an alkyl radical containing 1 to 18 carbon atoms, a cycloalkyl or aryl radical, R1 and R11 each represents a hydrogen atom or a methyl group, R111 represents a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms and n and p each is 1 or 2.  They may be prepared by one of three methods (a) by reacting an N-methylolamide of an a ,b -unsaturated monocarboxylic or dicarboxylic acid with a b -[di-alkyl-, -cycloalkyl- or -arylphosphono]-propionamide, (b) by reacting an amide of an a ,b -unsaturated monocarboxylic or dicarboxylic acid with a b -[di-alkyl-, -cycloalkyl- or arylphosphono] - N - methylolpropionamide or (c) by reacting an amide of an a ,b -unsaturated monocarboxylic or dicarboxylic acid, which is substituted on the amide nitrogen atom by N-methylene -b -chloropropionamide with a dialkyl, dicycloalkyl or diarylphosphite. The condensation reaction according to (a) and (b) is advantageously carried out in aqueous solution at a pH ranging from 0 to 6.5 and at a temperature from 20 DEG  C. to 70 DEG  C. and the reaction according to (c) is advantageously carried out in the presence of an acid acceptor.  The novel compounds are particularly useful as monomers in the preparation of linear polymers of high molecular weight (see Division C3).ALSO:Linear high molecular weight polymers having flame-inhibiting and biocidal properties are manufactured from at least one monomer of the general formula <FORM:1074237/C3/1> wherein A represents <FORM:1074237/C3/2> -COOH, -CONH2 or -CONHCH2OR111, R represents an alkyl radical containing 1 to 18 carbon atoms, a cycloalkyl or aryl radical, R1 and R11 each representsan hydrogen atom or a methyl group, R111 represents an hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms and n and p each is 1 or 2 by homopolymerisation or copolymerisation with another monomer of the above formula, or with at least one other polymerizable compound, in solution or emulsion, in the presence of an ionic catalyst or of a catalyst capable of furnishing free radicals.  The polymers may be obtained in the form of liquids, gels, emulsions or granulates.  Monomers suitable for the manufacture of copolymers are vinyl esters of organic acids, vinyl alkyl ketones, vinyl halides, vinylaryl compounds, derivatives of the acrylic acid series such as salts, acrylonitrile or acrylic acid amide and preferably its derivatives substituted on the amide nitrogen, acids and especially esters of a ,b -ethylenically unsaturated monocarboxylic or dicarboxylic acids containing 3 to 5 carbon atoms, and polymerizable olefines. They may also be copolymerized with polymerizable polyesters e.g. with polyesters from maleic anhydride and ethylene glycol or from maleic anhydride.  Tetrachlorophthalic anhydride and ethylene glycol.  The polymers can be insolubilized by heating at 100-180 DEG  C. The polymers may be used in combination with other high polymers or pre-condensates such as aminoplasts e.g. condensation products of formaldehyde with urea, cyanamide, dicyandiamide or especially melamine.  Solutions and emulsions of the polymers are suitable for forming shaped articles, coatings and impregnations.ALSO:Textiles may be flame-proofed by impregnating them with a composition containing as the flame proofing agent a polymer derived from a monomer of the general formula: <FORM:1074237/D1-D2/1> wherein A represents <FORM:1074237/D1-D2/2> -CONHCH2OR\yG, R represents an alkyl radical containing 1 to 18 carbon atoms, a cycloalkyl or aryl radical, R\sv and R\yF each represents a hydrogen atom or a methyl group, R\yG represents a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms and n and p is each 1 or 2.  The polymers may be homopolymers or copolymers of the above mentioned compounds.  Monomers suitable for the manufacture of copolymers are vinyl esters of organic acids, vinyl alkyl ketones, vinyl halides, vinyl aryl compounds, derivatives of the acrylic acid series and polymerisable olefines. The polymers may also be used in combination with other polymers or pre-condensates such as urea-formaldehyde, cyanamide, dicyandamide and melamine.  Examples describe the impregnation of cotton fabric, spun rayon fabric and polyester fabric by padding the fabric with an aqueous resin solution containing a polymer derived from the novel monomers of the invention, hexamethylol-melamine pentamethyl ether and ammonium chloride. Other textiles which may be impregnated are cellulose 2 1/2 -acetate, cellulose triacetate, polyesters, acrylonitrile or nylon fibres.  A stick of wood is also impregnated with various compositions to demonstrate the flame-proofing properties of various polymers derived from monomers of the invention.ALSO:Non-porous materials such as metals, glass or wood and porous materials such as textiles, paper or leather may be coated with polymers derived from a monomer of the general formula: <FORM:1074237/B1-B2/1> wherein A represents -CONH-CH2-NHCO <FORM:1074237/B1-B2/2> or -CONHCH2OR\yG, R represents an alkyl radical containing 1 to 18 carbon atoms, a cycloalkyl or aryl radical; R' and R\yF each represents a hydrogen atom or a methyl group, R\yG represents a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms and n and p is each 1 or 2.  The polymers may be homopolymers or copolymers of the above mentioned compounds. Monomers suitable for the manufacture of copolymers are vinyl esters of organic acids, vinyl alkyl ketones, vinyl halides, vinyl aryl compounds, derivatives of the acrylic acid series and polymerisable olefines.  The polymers may also be used in combination with other polymers or pre-condensates such as urea-formaldehyde, cyanamide, dicyandiamide and melamine.