Patent GB-1115631-A (GB)
Title: Sulphur-containing carbonamides and polymers and use thereof
IPC: D06P1/44
Filed: 1965-04-06
Abstract: The invention comprises polymers and copolymers of compounds of formula <FORM:1115631/C3/1> <FORM:1115631/C3/2> <FORM:1115631/C3/3> where A is -CONHCH2NR2.SO2R1, -COOH, -CONH2 or -CONHCH2OR111; R1 is unsubstituted or substituted alkyl, aryl, aralkyl, cycloalkyl or heterocyclic; R2 is hydrogen or a group as for R1; or R1, R2 and -SO2-together with N form a heterocyclic ring; R1 and R11 are each hydrogen or methyl; and R111 is hydrogen or C1- 4 alkyl (see Division C2); polymers of the compounds of Specification 1,092,873 are disclaimed.  The polymerization may be effected in solution or emulsion and in the presence of ionic or free-radical catalysts. Suitable comonomers are vinyl esters; vinyl alkyl ketones; vinyl halides; vinyl-aryl compounds; acrylonitrile; acrylamides and methacrylamides; esters of acrylic, methacrylic, a -chloroacrylic, crotonic, maleic, fumaric or itaconic acid with C1- 18 mono- or di-alcohols or with phenols; unsaturated mono- or dicarboxylic acids; or olefines such as isobutylene, butadiene or chloroprene.  The polymers may be used for the manufacture of shaped articles, coating, impregnating textile materials, or as binders for pigments.  In examples, compounds of the first formula above (viz. derivatives of acrylamide, methacrylamide or crotonamide) are homopolymerized or copolymerized in aqueous medium (with or without emulsifiers or acetone) using hydrogen peroxide/ascorbic acid/ferro-ammonium sulphate or ammonium or potassium persulphate catalyst, sometimes together with sodium bisulphite, or in an organic solvent (ethyl acetate or acetone) using benzoyl peroxide or azodiisobutyronitrile as catalyst; comonomers used are one or more of n-butyl acrylate, vinylidene chloride, vinyl acetate, calcium acrylate, diethyl aminopropylacrylamide quaternated with chloracetamide, methyl acrylate, acrylonitrile, 2-ethylhexyl acrylate or acrylic acid.  The products form films which can be cured on heating.  Examples also illustrate the incorporation of these products in printing, deressing or coating compositions for natural or synthetic fabrics, other components used being selected from petroleum fractions, azo pigments, methylol melamine or ethylene urea ethers, ammonium acid phosphate, polyethylene, magnesium chloride, citric acid, sodium alginate, copper phthalocyanine, gas soot, dioctyl phthalate, hydroabietyl alcohol - ethylene oxide condensate (isocyanate cross-linked) benzine, oleyl alcoholethylene oxide condensate, methylcellulose, ammonium chloride.ALSO:The invention comprises compounds of the formula <FORM:1115631/C2/1> <FORM:1115631/C2/2> <FORM:1115631/C2/3> where A is -CONHCH2NR2.SO2R1, -COOH, -CONH2 or -CONHCH2OR111; R1 is unsubstituted or substituted alkyl, aryl, aralkyl, cycloalkyl or heterocyclic; R2 is hydrogen or a group as for R1; or R1, R2 and -SO2-together with N form a heterocyclic ring; R1 and R11 are each hydrogen or methyl; and R111 is hydrogen or C1- 4 alkyl; and their production by condensing R1SO2NHR2 with an N-methylolamide of an appropriate unsaturated acid.  The compounds claimed in Specification 1,092,873 are disclaimed.  The compounds of the invention may be polymerized (see Division C3); they may also be prepared by condensation of an appropriate unsaturated acid amide with an appropriate N-methylolsulphonamide.ALSO:Coatings on non-porous materials such as metal, glass or wood or on porous materials such as textiles, paper or leather comprise a polymer of a compound of formula:-  <FORM:1115631/B1-B2/1> or <FORM:1115631/B1-B2/2> or <FORM:1115631/B1-B2/3> where A is -CONHCH2NR2-SO2R1, -COOH2, -CONH2 or -CONHCH2OR111, R1 is unsubstituted or substituted alkyl, aryl, aralkyl, cycloalkyl or heterocyclic; R2 is hydrogen or a group as for R1; or R1, R2 and -SO2- together with N form a heterocyclic ring; R1 and R11 are each hydrogen or methyl; and R\yG is hydrogen or C1-4 alkyl (see Division C3).  In Example 29 a nylon fabric is so coated.ALSO:Dressing agents for textiles and other porous materials and binders for printing inks comprise a polymer of a compound <FORM:1115631/D1-D2/1> where A is - CONHCH2NR2.  SO2R1, -COOH, -CONH2 or -CONHCH2OR111; R1 is unsubstituted or substituted alkyl, aryl, aralkyl, cycloalkyl or heterocyclic; R2 is hydrogen or a group as for R1; or R1, R2 and -SO2-together with N form a heterocyclic ring; R1 and R11 are each hydrogen or methyl; and R111 is hydrogen or C1-4 alkyl (see Division C3).  The polymers may be impregnated into porous materials such as textiles, paper and leather e.g. cotton, viscose rayon, cellulose esters or synthetic materials.  Examples of dressing agents and printing inks containing such polymers are given.  Printing pastes are exemplified in Examples 23 and 27.