Patent GB-795339-A (GB)
Title: New diazoamino-compounds and process for making them
Filed: 1954-08-27
Abstract: The invention comprises diazo-amino compounds of formula: <FORM:0795339/IV (b)/1> where R is a benzene residue, Y is p and X and H o to -N = N-, X is Me, MeO, EtO (U), H, Cl or NO2, Y is H or a substituent and Z is Et or n-propyl (V), isopropyl or phenyl (W) or Me and the residue Y(X)R.H-N = N- is the residue of an amine free of water-solubility imparting groups, the free amine of which has a pKA value which must be less than 3.7 and, subject to this limitation, differ by not more than \sB 0.7 from the value C = CX;Z-CY, where C(X = H; Z = Me) = 3.4, C(X = U; Z = Me) = 2.7, C(X = Cl, Z = Me) = 2.3, C(X = NO2; Z = Me) = 1.0, C(X = H; Z = V) = 3.2, C(X = U; Z = V) = 2.2, C(X = Cl; Z = V) = 2.0, C(X = NO2; Z = V) = 0.5, C(X = H, Z = W) = 2.8, C(X = U, Z = W) = 2.0, C(X = Cl; Z = W) = 1.7, C(X = NO2; Z = W) = 0.1, C(Y = CN, SO2\t alkyl, sulphonamide) = 1.0 and C(Y = NO2) = 1.4 and CY = O when Y is H or a substituent other than one of those specified above.  They are made by condensing appropriate aminodicarboxylic acids and diazotized amines, advantageously in an alkaline medium.  Specified acids are a -(2-carboxyphenyl)-amino-propionic, butyric, valeric, b -methylbutyric and phenylacetic acids.  Substituents which may be in the amines other than those already specified are chlorine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, nitro, acylamino, cyano, alkyl or aryl sulphone and sulphonamide groups.  Specified amines are 1-amino-2,5-dichloro-, 2-chloro - 5 - trifluoromethyl -, 2 - methyl - and methoxy - 4 - nitro -, 2 - nitro - 4 - methoxy-, 4 - methylsulphonyl - and 2 - chloro - 4 - cyano-5-methyl-benzenes.  The products may be isolated from their solutions by means of rapid drying processes and especially by spray drying.  Precipitation with an excess of alkali metal hydroxide may be used in some cases.  The products are used in printing pastes which may be developed under neutral or acid conditions.  Examples are provided of the preparation of the diazo-amino compounds from the above specified reactants and their use in printing processes.  The dicarboxylic acid reactants are made by condensing anthranilic acid with potassium cyanide and an appropriate aldehyde in the presence of methanol and hydrolysing the product with aqueous potassium hydroxide, details of the reactions being given in the examples.  Specifications 729,156, 729,157 and 780,266 are referred to.ALSO:Printing pastes which may be developed under neutral or acid conditions contain a diazoamino compound of the formula: <FORM:0795339/IV (b)/1> where R is a benzene residue, Y is p and X and Ho to -N = N-, X is Me, MeO, EtO (U), H, Cl or NO2, Y is H or a substituent and Z is Et or n-propyl (V), isopropyl or phenyl (W) or Me and the residue Y(X)R.H-N = N- is the residue of an amine free of water-solubility imparting groups, the free amine of which has a pKA value which must be less than 3.7 and, subject to this limitation, differ by not more than \sB 0.7 from the value C = CX;Z-CY, where <FORM:0795339/IV (b)/2> alkyl, sulphonamide)= <FORM:0795339/IV (b)/3> 1.4 and CY = O when Y is H or a substituent other than one of those specified above.  The preparation of the compounds and components used in their manufacture are described (see Group IV (b)).  Specified coupling components for use with the diazoamino compounds are acetoacetylamino compounds, 2-naphthol-3-carboxylic acid arylides and oxydiphenylene oxide-, oxycarbazole- and oxyanthracene-carboxylic acid arylides.  Examples are provided of the use of certain of the diazoamino compounds in printing processes as pastes containing sodium diisopropylnaphthalene sulphonate together with compounds such as urea, glycerol, alcohol, thiodiethylene glycol, glycol monoethyl ether, aqueous sodium hydroxide, sodium chlorate, neutral chromate solution; terpentine, starchtragacanth and coupling components such as the sodium salts of 2,3-oxynaphthoic acid anilide, 11-naphthylamide and 21-methoxyanilide. Specifications 729,156, 729,157 and 780,266, [both in Group IV (b)], are referred to.