Patent GB-769255-A (GB)
Title: Improvements in or relating to aqueous coloring compositions and preparation thereof
IPC: C07D233/32
Filed: 1955-04-05
Abstract: An aqueous composition comprises a pigment and a binder comprising a water-insoluble linear copolymer of one or more monoethylenically-unsaturated monomers and 1 to 15 per cent by weight of a monomer of the formula CH2=CH-O-A-NRCONHR1 where A is an ether-oxygen linked alkylene group having 2 to 3 carbon atoms or a branched or straight chain alkylene group having 2 to 4 carbon atoms between adjoining oxygen and nitrogen atoms, and R and R1 are hydrogen, methyl, ethyl, propyl, ispropyl, or ether-linked lower aliphatic groups of 1 to 3 carbon atoms, except that R may form with R1 a ring-closing alkylene group consisting of -CH2CH2-, -CH(CH3)CH2- or -CH2.CH2.CH2-.  The composition may also contain a thickener and a cross-linking agent.  Monomers of the above formula specified are vinyloxyethylurea, N-vinyloxyethyl - N,N1 - ethylene urea, 1 - (2 - vinyloxyethyl - 2 - hexahydropyrimidine, 1 - (2 - vinyloxypropyl) - 2 - imidazolidone, N - methyl - N - vinyloxyethylurea, N - vinyloxyethyl - N1 - ethyl urea, vinyloxyethyoxyethyl urea, vinyloxyethoxyethoxyethyl urea, and beta-ureidoisobutyl vinyl ether. The other monomer or monomers may be N-dimethyl to N-dioctyl acrylamide, the methyl to amyl, or the phenyl, benzyl or phenylethyl, esters of acrylic, methacrylic, ethacrylic, propylacrylic, chloroacrylic or bromoacrylic acids, styrene, alpha-methyl styrene, dimethylstyrene, dichlorostyrene, cyanostyrene, methoxystyrene, 4 - chloro - 1 - vinyl - naphthalene, vinyl and vinylidene chlorides or bromides, methyl or ethyl vinyl ketone, methyl isopropenyl ketone, the dimethy to dibutyl and the diphenyl, dibenzyl, ditolyl and di-(phenyethyl) esters of itaconic acid, the vinyl, allyl and methallyl esters of acetic, propionic and valeric acids, vinyl thiophene, 4-vinyl pyridine, vinyl pyrrole, acrylonitrile and methacrylonitrile.  The pigment may be an azo compound, a phthalocyanine compound, or a vat dyestuff, or carbon black, iron oxide, chrome yellow, titanium dioxide, lithopone, aluminium, bronze, brass, chromium, gold, or mixtures.  Thickening agents mentioned are gum tragacanth, water-soluble cellulose ethers, polyvinyl alcohol or partially saponified polyvinyl acetate.  The composition may also contain an alkaline buffer such as sodium acetate, sodium carbonate, chalk, morpholine, or ammonia.  The cross-linking agent may be formaldehyde, N,N-ethyleneurea, N,N1-ethyleneurea, N,N1-dimethylurea, N,N1 - diethylurea, N,N1 - dimethoxymethylurea, N,N-dimethoxymethylurea, N,N1-diethoxyethylurea, tetramethoxymethylurea, tetrathoxyethylurea, N,N-dimethylmelamine, dimethoxymethyl - monomethylol melamine, hexamethylene - bis - N,N - ethyleneurea, the mono-biguanidines obtained from dicyandiamide and ethylamine, or di - ethylamine, hydroxyethylamine, propylamine, butylamine, 2-hydroxy-propylamine, benzylamine, aniline toluidines, or methoxy-aniline, or biguanides from ethylene-diamine, alpha-beta-diaminopropane, trimethylene diamine or hexamethylene diamine, or polyacrylic or methacrylic acid.  The cross-linking is preferably effected by heating the applied dispersion to a temperature of 180 DEG  to 350 DEG  F.  The compositions are used for coating, dyeing and printing textiles, paper, paperboard, wallboard, plastered walls, metals, wood, leather, cements, stucco, concrete, or glass.  In an example, n-butyl acrylate and beta-ureidoisobutyl vinyl ether are copolymerized in aqueous emulsion in the presence of a redox catalyst system consisting of ammonium bisulphite, triethanolamine and ammonium persulphate, using as the emulsifier an ethylene oxide condensation product with t-octylphenol.  Copolymers of ethyl acrylate and vinyloxybutylurea, n-butyl acrylate and N,N1-ethyleneureidoethyl vinyl ether, ethyl acrylate, methylmethacrylate and 1 - (2 - vinyloxypropyl) - 2 - imidazolidone, isopropyl acrylate and N-methylN-vinyloxyethyl urea, ethyl acrylate and 1-(2-vinyloxyethyl) - 2 - hexahydropyrimidone, and styrene, n-propyl acrylate and vinyloxyethoxyethylurea may be similarly prepared.ALSO:Textiles and other substrates are coloured, e.g. by printing or padding, and also crease proofed and rendered resistant to shrinkage on washing, by applying to the textile material an aqueous composition comprising a pigment and a water-insoluble linear copolymer of one or more monoethylenically unsaturated monomers of the formula:-CH2 = CH-O-A-NRCO NHR1 where A is an ether - oxygen linked alkyllene group having 2 or 3 carbon atoms or a branched or straight chain alkylene group having 2 to 4 carbon atoms between adjoining oxygen and nitrogen atoms, and R and R1 are each hydrogen, methyl, ethyl, propyl, isopropyl, or an ether-linked lower aliphatic group of 1 to 3 carbon atoms, except that R may form with R1 a ringclosing alkylene group consisting of -CH2 CH2-, CH(CH3)CH2- or CH2. CH2 CH2, and optionally a thickener and cross-linkage agent, and drying and hardening the treated textile at elevated temperature e.g. 180-350 DEG F.  The Specification contains an extensive list of monomers and crosslinking agents (see Group IV(a)).  The pigment may be an azo compound, a phthalocyanine compound, or a vat dyestuff, or carbon black, iron oxide, chrome yellow, titanium oxide, lithopone, aluminium, bronze, chromium, gold, or mixtures.  Thickening agents mentioned are gum tragacanth, water-soluble cellulose ethers, polyvinyl alcohol, or partially saponified polyvinyl acetate.  The composition may also contain an alkaline buffer such as sodium acetate, sodium carbonate, chalk, morpholine, or ammonia.  The textile material may be woven, knitted, or felted and the fibres or yarns may be cotton, rayon, silk, wool, linen, cellulose acetate, casein, soya bean protein, polyamides, polyglycol terephthalate, polyethylene, polyvinyl chloride, polyvinylidene chloride, polyacrylonitrile, polyvinylidene chloride, copolymers of vinylidene chloride and vinylacetate, or ethylene, or acrylonitrile, or copolymers of acrylonitrile with vinyl acetate, methacrylonitrile, or vinyl pyridine.  The colouring may be applied to the textile by padding, printing rolls when localized colour is required, or by stencilling.  In an example a rayon challis is crease-proofed and coloured by padding the challis with an aqueous dispersion consisting of a copolymer of ethyl acrylate with vinyloxybutylurea, a phthalocyanine blue pigment, a water-soluble hydroxyethyl cellulose, and dimethoxymethyl urea and pyridine hydrochloride as the cross-linkage agents, and the fabric dried and cured between 240-300 DEG F. for ten minutes.  Other substrates mentioned are paper, paperboard, wall board, and leather.