Patent GB-1082976-A (GB)
Title: Unsaturated amides and polymers thereof
IPC: C08F8/00
Filed: 1964-06-29
Abstract: Monomers of the formula <FORM:1082976/C3/1> wherein R is hydrogen or C1- 18 alkyl, m is 0, 1 or 2 and n is 1 or 2, are polymerized in bulk, solution, emulsion or suspension, or on fibres, filaments, woven or knitted fabrics or carded webs, alone or with one or more other copolymerizable monomers in the presence of polymerization catalysts. Alternatively, monomers of the formula H2C = CHCH2(CH2)mCONH2 may be so polymerized and subsequently methylolated or alkoxymethylated.  The monomers may be applied to starch, cellulose, e.g. cotton, incompletely etherified or esterified cellulose, e.g. rayon, polyamide nylons, wool, silk or casein, and subjected to conditions such that the monomers react with free hydroxy groups and are simultaneously or subsequently polymerized, or such that the monomers are polymerized and subsequently reacted with free hydroxy groups. The polymerization catalysts may be ammonium persulphate or tertiary-butyl hydroperoxide, and may be incorporated during or after impregnation with the monomer.  Other peroxy and azo catalysts are also specified.  Effects so-produced are stiffening, crease - proofing, shrink - proofing, water-resistance or -repellency and lubricity. The polymers may also be obtained in the form of granules.  They may be used as coating, impregnating or moulding resins; in admixture with starch, gelatine or plasticizers for coatings, films, thickening materials and warp sizes; in admixture with vinyl and acrylic resins and optional dyes and pigments to provide coatings on textiles, leather, paper, wood, metal or glass; as lacquers and enamels e.g. as solutions in xylene or butoxyethyl acetate; and as ingredients of water-based paints.  The polymers may also be modified by reaction with polyisocyanates, polyepoxides, urea-formaldehyde, N, N1-ethyleneurea-formaldehyde or amino-triazine-formaldehyde condensates.  In examples the monomers are homopolymerized or emulsion copolymerized with one or more of methyl, ethyl, butyl or 2-ethylhexyl acrylate, methacrylic acid, methylmethacrylate, vinylidene chloride, vinyl toluene, styrene, acrylamide and acrylonitrile, in the presence of ammonium persulphate, sodium hydrosulphite, an ethylene oxide condensate of tertiary-octylphenol and bromotrichloromethane.  Mercaptans, e.g. mercapto-ethanol, may also be used.  In another example an aqueous solution of N-methylol-4-pentenamide and the hydrochloride of 2-amino-2-methyl-propanol-1 is applied to cotton print-cloth, cured, washed with hot dilute sodium nitrite solution, padded with ammonium persulphate solution and further cured to impart crease-resistance. The aqueous dispersions of polymers obtained in the examples may be further admixed with water-soluble cellulose ethers, polyvinyl alcohol, partially saponified polyvinyl acetate, copolymers of acrylic or methacrylic acid with methyl or ethyl acrylate, sodium acetate, sodium carbonate, chalk, morpholine, N-methyl-morpholine, triethylamine, ammonia, titanium dioxide, zinc oxide, zinc sulphide, barium sulphate, lithopone, mica, silica, iron oxides, chrome yellows, carbon black, powdered or flaked aluminium, bronze, brass, chromium and gold, sodium alginate, blue copper phthalocyanine pigment, diethylene glycol, tertiary-octylphenoxypolyethoxyethanol and the ammonium salt of a diisobutylene/ maleic anhydride copolymer, to provide paints, adhesives and coating compositions.ALSO:Novel monomers of the formula <FORM:1082976/C2/1> wherein R is hydrogen or C1- 18 alkyl, m is 0, 1 or 2 and n is 1 or 2, are prepared by methylolating or alkoxymethylolating the corresponding amides of the above formula in which n is 0 or by etherifying methylolamides of the above formula in which R represents hydrogen.ALSO:Aqueous dispersions of copolymers of monomers of the formula:  <FORM:1082976/D1-D2/1> wherein R is hydrogen or C1-18 alkyl, m is 0, 1 or 2 and n is 1 or 2, with other polymerisable monomers such as ethyl, butyl or 2-ethylhexyl acrylate or vinylidene chloride, are added to paper pulp and cast into sheets; mixed with blue copper phthalocyanine pigment, sodium alginate and aqueous tertiary-octylphenoxypoly-ethoxyethanol and applied to cotton percale; applied to non-woven fabrics such as rugs to impart bodying and to prevent ravelling; padded onto carded webs of viscose rayon fibres, air dried and cured at 300 DEG F. to impart flexibility and soft hand; applied by means of spraying, brushing, roller-coating, dipping or knife-coating to fibres, filaments, and woven or knitted fabrics of polyamide nylon, wool, silk, cotton, rayon or other cellulose derivatives, and dried and cured in presence of a curing catalyst (a list of which is specified) to impart stiffness, shrink- or crease-proofing properties, water-resistance or -repellency, or lubricity; or similarly applied to leather, wood panels, chipboard, kraft bag paper, wall paper, asbestos cement shingles and siding sheets, stone, cement, concrete, bricks and cinder block to impart water-resistance and -repellency.ALSO:Homopolymers or copolymers of monomers of the formula:-<FORM:1082976/B1-B2/1> wherein R is hydrogen or C1-18 alkyl, m is 0, 1 or 2 and n is 1 or 2, are applied alone (e.g. as hot-melt coatings) or in admixture with water, xylene or butoxyethyl acetate solvents, vinyl and acrylic resins, an ammonium salt of a diisobutylene/maleic anhydride copolymer, titanium dioxide, zinc sulphide and barium sulphate, as paints, coatings or lacquers to leather, wood panels, chipboard, kraft bag paper, wall paper, asbestos cement shingles and siding sheets, glass, ceramics, stone, cement, concrete, bricks, cinder block, textiles, bare and primed cold rolled steel, aluminium and brass, or the bibulous fibrous backing of masking tape, or for backing pile fabrics used in upholstery.  Application may be accomplished by spraying, brushing, roller-coating, dipping or knife-coating, and may be followed by curing by ageing or heating to 200 to 750 DEG F., e.g. with infra-red lamps, in the presence or absence of curing catalysts, lists of which are specified.