Patent GB-300549-A (GB)
Title: Manufacture of acid dyestuffs of the phenonaphthosafranine series
IPC: C09B17/04
Filed: 1928-11-09
Abstract: 300,549. Geigy Akt.-Ges., J. R. Nov. 14, 1927, [Convention date]. Addition to 265,986, 284,614, 284,615, 285,486, and 297,441. Azinc dyes.-An unsynmetrical N-alkylated-pphenylenediaminesulphonic acid, in which the sulphonic-group occupies the ortho position to the primary amino group is condensed with an isorosinduline-6-sulphonic acid, having the following general formula, the 6-sulphonic group being removed during the condensation as in the processes of Specification 265,986, 284,614, and 284,615 :- wherein Rand R<1> represent hydrogen, alkyl or aryl, R<2> represents an alkyl or substituted alkyl group and X an acid radical, positions 1, 2, 8, 9, 10 being possibly occupied by a monovalent radical, such as a halogen, hydroxy, alkyloxy, methyl, acidylamino or sulphonic group. Acid wool dyestuffs, fast to alkali and light are thus produced, which give more violet shades than those produced by the processes of the parent Specifications. Similar dyestuffs may also be produced by using phenonaphthosafranines having an alkyl or substituted alkyl group attached to the meso azine nitrogen in the sulphonation processes of Specifications 285,486 and 297,441. According to examples :-(1) an isorosinduline having the formula : is condensed, by boiling in a reflux, with 1- methyl-2-ethylamino-5-aminobenzene-4- sulphonic acid dissolved in the theoretical amount of sodium carbonate solution; (2) isorosindulines having the formulµ: with 1-methyl-2-methylamino-5-aminobenzene-4- sulphonic acid; (3) a phenonapthosafranine having the formula : obtainable from the isorosinduline used in example 1 by condensation with 1-amino-4-ethylamino-3-methylbenzene is further sulphonated according to the process of Specification 285,486, the resulting dyestuff being identical with that obtained according to example 1; (4) the phenonaphthosafranine obtained by condensing 1- methyl-2-oxy-5-aminobenzene - 4 - sulphonic acid with the isorosinduline having the formula: is further sulphonated, the new sulphonic group entering the benzyl nucleus. The meso alkylisorosinduline-6-sulphonic acids used as parent material may be made from monoalkylated-2- naphthylamines by treatment with p-nitrosoarylamines or by other known methods, with subsequent treatment with a sulphite according to Specification 14962/98. For example, the isorosinduline required in the fourth example is prepared by coupling nitrosoethylbenzylaniline with ethyl-2-naphthylamine and sulphonating to introduce the sulphonic acid group into the 6-position. The isorosinduline required in the first example is prepared by condensing monoethyl-2-naphthylamine with the azo dyestuff 2 : 5-dichloraniline # diethylmetanilic acid, and further sulphonating to form the 1 : 6-disulphonic. acid. The isorosindulines required in example 2 are similarly prepared from the corresponding alkyl-2.naphthylamines. 2-Napthylaminoaceticacidmethylester and its homologues, oxyethyl-2-naphthylamines and its homologues and the corresponding 6 and 7 sulphonic acids of these bases are also mentioned as suitable starting materials. Specifications 24410/97 and 14961/98 also are referred to. 2-Napthylaminoacetic acid methyl (and ethyl) ester-6-for 7)-sulphonic acids are prepared by heating sodium 2-naphthylamine-6-(or 7)-sulphonate with chloracetic acid methyl (or ethyl) ester and magnesia in an autoclave. 2 - Oxyethylaminonaphtaline-6-(or 7)-sulphonic acid is prepared by heating sodium-2-naphthylamine-6(or 7)-sulphonate with ethylenechlorhydrin and magnesia. 2-Napthylaminoaceticethyl ester (example 2) is prepared by refluxing monochloracetic ethyl ester with B-naphthylamine and sodium carbonate.