Patent GB-443394-A (GB)
Title: A process for producing fast prints on paper
IPC: C09D11/037
Filed: 1935-01-14
Abstract: Fast prints on paper of water-soluble dyestuffs containing one or more sulphonic and/or carboxylic groups are obtained by use of the dyestuffs in solution in diethylene glycol or one or more organic liquids miscible with diethylene glycol together with a water-soluble salt of an organic compound containing at least one basic nitrogen atom and an aliphatic residue comprising at least 10 carbon atoms. Specified dyestuffs are: (a) azo dyes, viz., Orange II, Kiton red 6B, Kiton fast orange G, Acid black HA, Cloth fast blue GTB, Chrome fast red B, o-anisidine --> 1-naphthol-3 : 6-disulphonic acid, 2 : 5-dichloraniline --> 1-(21-chloro-51-sulpho) phenyl-3-methyl-5-pyrazolone, and the chromium compound of the dyestuff 1 : 2-aminonaphthol-4-sulphonic acid --> 1-naphthol-8-sulphonamide; (b) dyes of the anthraquinone series, viz., Alizarine cyanine fast green EF and Alizarine direct violet R; (c) a triphenylmethane dye, viz. Xylene blue AS; (d) azine dyes, viz. Xylene fast blue BL and GL.  Specified water-soluble salts of nitrogenous organic compounds are: (a) those in which the high molecular aliphatic residue is united directly to the basic nitrogen atom, e.g. the hydrochlorides of hexadecylamine, octodecylamine, diethylcetylamine, dimethyloctodecylamine and diethyloctodecenylamine, hexadecyl pyridinium chloride, octodecylpyridinium bromide, trimethyloctodecylammonium sulphomethylate, benzylcetyldiethylammonium chloride, triethylcetylammonium chloride; (b) those in which the said residue is united indirectly to the basic nitrogen atom, e.g. (1) salts of diamines unilaterally mono- or diacylated by high molecular fatty acids (cf. Specifications 219,304, 294,582, [both in Class 2 (iii)], and 346,387), such as the trimethylammonium sulphate of mono-stearoylethylenediamine, the hydrochlorides of oleoyl-diethylethylene and -propylene diamines and of oleoylbenzoyldiethylethylenediamine, oleoylaminoethylenediethylallylammonium bromide, oleoylaminoethylenetriethylammonium - p - toluenesulphonate, the hydrochlorides of oleoylpiperidyl - N - ethylamide, oleoyl - b  - oxy - g  - diethylpropylenediamine and p - oleoylaminophenyldiethylaminoethylmethylamine, p-stearoylaminophenyltrimethylammonium sulphomethylate; (2) salts of monoacylpiperazines; (3) salts of acylated polyalkylenepolyamines (cf. Specification 337,368, [Class 2 (iii)]); (4) salts of mixed ethers such as that from cetyl alcohol and N-oxymethylpyridinium chloride; (5) the hydrochloride of diethyl-aminoethyloctodecyl carbonate; (6) salts of esters such as that of stearic acid with dimethyl- or diethyl-aminoethanol, the chloride of choline stearic acid ester, the stearic acid ester of N-o -oxyethylpyridinium chloride or of the addition product of glycerin monochlorhydrin or a : a <1>-glycerin dichlorhydrin and pyridine, the palmitic acid ester of 1-oxyphenyl-3-trimethyl-ammonium chloride; (7) salts of imidazoles such as pentadecyldihydroimidazole hydrochloride and m -heptadecenyl-dibenzylbenzimidazolium chloride; (8) salts of basic urethanes such as the addition products of dimethyl sulphate and diethylaminoethylcetylurethane or m-dimethylaminophenylcetylurethane: in all such compounds the stearic, palmitic or oleic acid residues may be replaced by residues of other acids such as capric, lauric, myristic or ricinoleic acids and the cetyl alcohol residue may be replaced by other higher alcohol residues.  In an example, paper is printed with a paste containing Cloth fast blue GTB or Xylene fast blue BL and p-stearoylaminophenyltrimethylammonium sulphomethylate dissolved in a mixture of ethyl alcohol and glycerol or of ethyl alcohol, butyl glycol, glycerol and water and is dried to obtain a powerful dark blue print fast to light, water and rubbing; a similar blue-green print is obtained if the dyestuff is replaced by Alizarine fast green.  Specification 396,992 also is referred to. Oleoylbenzoyldiethylethylenediamine hydrochloride is obtained as addition product from benzoyl chloride and oleoyldiethylethylenediamine. Oleoylaminoethylenediethylallylammonium bromide is obtained as addition product from allyl bromide and oleoyldiethylethylenediamine. Oleoylaminoethylenetriethylammonium - p - toluenesulphonate is obtained as addition product from ethyl p-toluenesulphonate and oleoyldiethylethylenediamine.  Oleoylpiperidyl-N-ethylamide and oleoyl-b -oxyg -diethylpropylenediamine are obtained by acylation of o -aminoethyl-N-piperidine and b -oxy-g -diethylaminopropylamine and b  - oxy - g  - diethylaminopropylamine (cf. Specification 276,012 [Class 2 (iii)]) respectively with oleic acid.  p - Oleoylaminophenyldiethylaminoethylmethylamine is obtained by reacting oleic acid chlorides with asymmetrical methyldiethylaminoethyl-p-phenylenediamine (cf. Specification 274,058, [Class 2 (iii)]).  p - Stearoylaminophenyltrimethylammonium sulphomethylate is obtained by the action of dimethyl sulphate on p-stearoylaminodimethylaniline.  Diethylaminoethylcetylurethane is obtained by reaction of asymmetrical diethylethylenediamine with the chlorocarbonic acid cetyl ester obtainable by reaction of cetyl alcohol with phosgene.  m - Dimethylaminophenylcetylurethane is similarly obtained by reaction of asymmetrical dimethyl-m-phenylenediamine with chlorocarbonic acid cetyl ester. Reference has been directed by the Comptroller to Specification 396,992.