Patent GB-785613-A (GB)
Title: New diazoamino-compounds and process for making them
IPC: D06P1/12
Filed: 1954-08-27
Abstract: Printing preparations for steam development are described which contain a diazoamino compound of the formula <FORM:0785613/IV (b)/1> where R is a benzene residue, X and H are each in ortho-position to the azo group, X is Me, OMe, OEt (U) or H or Cl, and Z is Me or benzyl (V) or a straight chain alkyl group (W) of 2-4 carbon atoms bound to N by an end carbon atom, the residue XR(H)-N = N- being the residue of an amine XR(H).NH2 which is free of groups imparting solubility in water and of which the pKA value differs by at most \sB0.7 from the value C(X;Z) where the latter is one of C(X=H;Z=V)=4.8, C(X=H;Z=W)=4.2, C(X=U;Z=V)=4.0, C(X=U;Z=W)=3.5, C(X=Cl;Z=V)=3.6 and C(X=Cl;Z=W)=2.9.  The preparations also contain other usual ingredients, those specified in an example being the sodium salts of 2,3-oxynaphthoic acid anilide and its 21-methyl- and -ethoxy- and 21,61 - dimethyl - derivatives, 3 - oxycarbazole-2 - carboxylic acid -41 - chloranilide, 1 - aceto - aceto - acetylamino - 2,5 - dimethoxy - 4 - chlorobenzene and 1 - acetylamino - 2 - methoxy - 4 - aceto - acetylamino - 5 - chlorobenzene as coupling components, sodium diisopropyl naphthalenesulphonate, urea, glycerol, alcohol, thiodiethylene glycol, caustic soda solution, starchtragacanth, sodium chlorate and turpentine.  The preparation of the diazoamino compounds is described (see Group IV (b)).ALSO:The invention comprises diazoamino compounds of formula <FORM:0785613/IV (a)/1> where R is a benzene residue, X and H are each in o-position to the azo group, X is Me, MeO, EtO (U), H or Cl, Z is Me or benzyl (V) or a straight-chain alkyl residue (W) of 2-4 carbon atoms bound to N by an end carbon atom the residue X-R(H)-N=N-being the residue of an amine XR(H)NH2 which is free from groups imparting solubility in water and of which the pKA value differs by at most \sB0.7 from the value C(X ; Z) where the latter is one of C(X=H; Z=V)=4.8, C(X=H; Z=W)=4.2, C(X=U; Z=V)=4.0; C(X=U; Z=W)=3.5, C(X=Cl; Z=V)=3.6 and C(X=Cl; Z=W)=2.9.  They are made by treating an appropriate N-substituted 1-aminobenzene-2-carboxylic acid-4-sulphonic acid, advantageously in alkaline solution, with a diazo compound of the amine of formula XR(H)NH2.  1 - Methyl -, - benzyl -, -ethyl- and -n-butyl-aminobenzene-2-carboxylic acid - 4 - sulphonic acids are specified.  The amines from which diazo compounds are made may contain further substituents in positions other than those oto the amino groups, e.g. halogen atoms, such as chlorine atoms and methyl, ethyl, methoxy, ethoxy, trifluoromethyl, nitro and acylamino groups such as a benzoylamino group.  Specified amines of this character are 1-amino-3-chloro-, -2-methyl-4- and -5-chloro-, -4-methyl- and -methoxy-, -2-methoxy-5-chloro-, 2-methoxy-4-chloro- and -benzoylamino-5-methyl-, -2,5-dimethoxy- and -diethoxy - 4 - benzoylamino - and - 2 - chloro - 4-methoxy-benzenes.  The diazoamino compounds are isolated by means of a rapid drying process in which the material is subjected to a high temperature in the aqueous phase for a short time although when dry the material may be held at a high temperature for a long period. Advantageously a spray drying process is used.  A roller drying process is also described.  The products are used in printing processes (see Group IV (c)) and may be applied together with conventional coupling compounds and developed by neutral or acid steaming processes.  Examples are provided of the preparation of diazoamino compounds using certain of the above-specified reactants, the pKA values of the amines used being given.