GB513170A - Photographic emulsions sensitized with the manufacture of dyes therefor - Google Patents

Abstract

513,170. Sensitizing dyes. KODAK, Ltd. March 29, 1938, No. 9535. Convention date, March 29, 1937. Drawings to Specification. [Class 2 (iii)] [Also in Group XX] Cyanine dyes are made by treating a hydroxyalkyl quaternary salt of a heterocyclic nitrogen base by the methods known to be capable of converting the alkyl or aryl or aralkyl quaternary salt of such heterocyclic base into a cyanine dye. The hydroxyalkyl quaternary salts are obtained by treating the heterocyclic nitrogen base with a halohydrin. In examples of preparing the quaternary salts (1)-(6) ethylenebromhydrin or trimethylenebromhydrin is heated with 1-methylbenzthiazole, quinaldine or lepidine ; the products may be converted into iodides or perchlorates &c. ; other heterocyclic bases are specified. The following methods for preparing the dyes are specified (a)-(k): (a) symmetrical cyanines by.condensing the hydroxyalkyl salts . with quaternary salts of the corresponding alkyl or arythiol compounds; (b) unsymmetrical cyanines by condensing the hydroxyalkyl salts with quaternary salts of a different alkyl or arythiol compound ; the arylthiol compounds can be prepared by condensing heterocyclic nitrogen bases containing a reactive chlorine atom in alpha- or gamma-position with a thiophenol, (c) pseudocyanines by condensing the hydroxyalkyl salts with a 2-halogenoquinoline or -benzquinoline, (d) pyrido-pseudocyanines by condensing the hydroxyalkyl salts with quaternary salts of a 2-halogenopyridine, (e) isocyanines by condensing the hydroxyalkyl salts with a quinoline quaternary salt, (f) carbocyanine by condensing the hydroxyaklyl salts with an ethyl orthoester, e.g. the acetate, propionate or benzoate, (g) dicarboxyanines by condensing the hydroxyalkyl. salts with a compound of the general formula R-N =CH-CH =CH-NHR.HX, where R =aryl, e.g. phenyl or tolyl, and X =an acid radicle, (h) unsymmetrical carbocyanines by condensing the hydroxyaklyl salts with the condensation product of diphenylformamidine and cyclamonium alkyl quaternary salts containing a reactive methyl group in alpha- or gamma-position to the pentavalent nitrogen atom (Specification 344,409), (i) tricarboxyamines by condensing the hydroxyalkyl salts with a compound of the general formula R-N =CH-CH =CH-CH =CH - NHR.HX, where R =aryl and X =an acid radical, (j) tetracarbocyanines by condensing the hydroxyalkyl salts with reactive heptadiene compounds and (k) pentacarbocyanines by condensing the hydroxyalkyl salts with reactive nonatriene compounds. All these processes are exemplified in the Specification. The dyes may be used for sensitizing photographic emulsions. Details'for preparing the emulsions and 22 spectrograms are given.