Patent GB-924002-A (GB)
Title: Process of colouring organic materials with pigment dyestuffs
IPC: C08K5/3462
Filed: 1961-05-19
Abstract: Organic products are coloured in the mass with pigment dyestuffs free from groups imparting solubility in water and having the formula <FORM:0924002/IV(a)/1> where A and B each represent an arylene residue, preferably a benzene radical, n is a whole number from 1-6, preferably 1, 2 or 3, and X and Y each represent an oxygen or sulphur atom or a group of the formula <FORM:0924002/IV(a)/2> where R represents a hydrogen atom or an alkyl, cycloalkyl, aralkyl or aryl group.  Preferably X and Y each represent an -NH- group.  Preferred dyestuffs are those of the formula <FORM:0924002/IV(a)/3> where R represents a halogen atom or an alkyl, alkoxy, nitro or amino group and n = 1, 2 or 3.  Dyestuffs specified include fluoflavine <FORM:0924002/IV(a)/4> and fluorubin <FORM:0924002/IV(a)/5> and compounds of the formulae (i) <FORM:0924002/IV(a)/6> (ii)-(vii) <FORM:0924002/IV(a)/7> <FORM:0924002/IV(a)/8> <FORM:0924002/IV(a)/9> <FORM:0924002/IV(a)/100> <FORM:0924002/IV(a)/111> <FORM:0924002/IV(a)/122> (viii) dyestuffs of the general formula <FORM:0924002/IV(a)/133> in which X and Y are respectively (a) -H,-CH3, (b) -CH3, -CH3, (c) -H, -Cl, (d) -Cl, -Cl, (e) -CH3, -Cl, (f) -NH2, -NH2, dyestuff of the <FORM:0924002/IV(a)/144> and dyestuffs of the formulae <FORM:0924002/IV(a)/155> <FORM:0924002/IV(a)/166> <FORM:0924002/IV(a)/177> <FORM:0924002/IV(a)/188> <FORM:0924002/IV(a)/199> The organic product to be coloured may be a spinnable mass, e.g. a high melting spinnable material, or a spinning solution.  Examples include viscose, cellulose acetate, polyamides, e.g. hexamethylene diamine adipamide and products made from e -caprolactam or o -amino undecanoic acid, polyesters, e.g. polyethylene terephthalate, polyethylene and polypropylene.  Other organic products which may be mass coloured include polyvinyl chloride, polyvinyl acetals, polystyrene and copolymers thereof, polyacrylates and silicone resins. Nitrocellulose lacquers may be coloured in this way, and titanium dioxide may be used as an additional pigment.  Desirably, the pigment dyestuff before incorporation into the organic product should have an average particle size not exceeding 3m .  A pigment preparation may be utilised, containing the dyestuff ground to this particle size, together with a dispersant and possibly also a binding agent. Addition polymer compositions  The colouring of addition polymer compositions by the process of the invention is described in Examples 4 (polyethylene); 6 (polyvinyl chloride containing dioctyl phthalate, cadmium stearate and titanic coloured with a paste of fluorubin of below 3m  particle size in dioctyl phthalate); and 11 (terpolymer latex of isobutyl acrylate/acrylonitrile/acrylic acid mixed with a modified methylol-melamine allyl ether emulsified with Turkey Red oil, an etherified ureaformaldehyde condensate and formic acid coloured with < = 1m  particles of fluoflavine dispersed in water containing 1,11-dinaphthylmethane-2,21 disulphonic acid sodium salt). Specification 924,001 is referred to.ALSO:A pigment dyestuff free from groups imparting solubility in water has the formula <FORM:0924002/IV(a)/1> where A and B each represent an arylene residue, preferably a benzene radical, n is a whole number from 1-6, preferably 1, 2 or 3, and X and Y each represent an oxygen or sulphur atom or a group of the formula <FORM:0924002/IV(a)/2> where R represents a hydrogen atom, or an alkyl, cycloalkyl, aralkyl or aryl group.  Preferably X and Y each represent an -NH- group.  Preferred dyestuffs are those of the formula <FORM:0924002/IV(a)/3> where R represents a halogen atom or an alkyl, alkoxy, nitro or amino group and n=1, 2 or 3.  Dyestuffs specified include fluoflavine <FORM:0924002/IV(a)/4> and fluorubin <FORM:0924002/IV(a)/5> and compounds of the formulae (i) <FORM:0924002/IV(a)/6> (ii)-(vii) <FORM:0924002/IV(a)/7> (viii) dyestuffs of the general formula <FORM:0924002/IV(a)/8> in which X and Y are respectively (a) -H, -CH3, (b) -CH3, -CH3, (c) -H, -Cl, (d) -Cl, Cl, (e) -CH3,- Cl, (f) -NH2, -NH2, a dyestuff of the formula <FORM:0924002/IV(a)/9> and dyestuffs of the formulae <FORM:0924002/IV(a)/100> The pigment dyestuff is desirably ground to an average particle size not exceeding 3m  before use, and may be used in the form of a pigment preparation containing the ground dyestuff together with a dispersant and possibly also a binding agent.  Sulphite waste liquor or a dinaphthyl methane disulphonate may be used as dispersants in making water-dispersible preparations.  In an example, a cotton fabric is dyed in a dye bath containing, per 1000 parts of water, 15 parts of a copolymer latex from 85,8 parts of isobutyl acrylate, 9,6 parts of acrylonitrile and 4,6 parts of acrylic acid, 15 parts of an emulsion of 70% strength of a methylol-melamine allyl ether emulsified with Turkey red oil and modified with soybean fatty acid, 50 parts of a water-soluble methyl ether of a urea-formaldehyde condensation product in which for every mol. of urea more than two mols. of formaldehyde have been condensed, 5 parts of a pigment suspension made by grinding 4,8 parts of fluoflavine, 4,8 parts of the sodium salt of 1:11-dinaphthyl methane -2:21-disulphonic acid and 22,1 parts of water to a particle size of 1m , and 20 parts of 10% formic acid to obtain a fast yellow dyeing.  In a further example a textile printing paste is made from fluorubin, a condensation product of 2:6-ditertiarybutylpara-cresol with ethylene oxide, and a melamineformaldehyde-casein lacquer resin emulsion.  Specification 924,001 is referred to.