GB1476175A - Bis-triazinylamino-stilbene-disulphonic acid derivatives - Google Patents

Abstract

1476175 Bis-(triazinylamino)stilbene derivatives HOECHST AG 17 May 1974 [19 May 1973] 22041/74 Heading C2C [Also in Divisions C3 and D1] Novel compounds have the Formula I in which X represents -Cl, -NR<SP>1</SP>R<SP>2</SP>, -OR<SP>3</SP> or -NRCH 2 CH 2 SZ; R<SP>1</SP> represents -H, alkyl or alkenyl each of up to 20 carbon atoms, C 4-8 cycloalkyl, aryl of the benzene or naphthalene series or an aromatic or saturated 5- or 6-membered heterocyclic ring containing 1 or 2 N, O and/or S heteroatoms or the benzo analogues thereof, which groups R<SP>1</SP> are optionally substituted by non-chromophoric substituents; R<SP>2</SP> represents -H, or a C 1-4 alkyl group optionally substituted by non-chromophoric substituents or R<SP>1</SP> and R<SP>2</SP> together with the common nitrogen atom form a saturated heterocyclic 5- to 7-membered ring which optionally contains a further O or N atom and which is optionally substituted by non-chromophoric substituents; R<SP>3</SP> represents a C 1-4 alkyl, a phenyl or a naphthyl group each of which is optionally substituted by non-chromophoric substituents; M is hydrogen or a colourless cation; Z is the same as M or is -SO 3 M or is a bond to another sulphur atom in the molecule; and R is -H, or C 1-4 alkyl or Z and R together represent a methylene group. The compounds of Formula I in which Z represents the group -SO 3 M are prepared by the sequential condensation of the corresponding amines and hydroxy compounds with cyanuric chloride in the stoichiometric molar proportions. Compounds of Formula I in which Z is other than -SO 3 M are obtained from the latter by (i) hydrolysing in an aqueous acidic alcoholic medium to give the corresponding mercapto derivative (Z=M), (ii) reaction with CH 2 O/HCl to give the corresponding thiazolidine (Z + R = -CH 2 -), or (iii) heating with a water-soluble sulphide to yield the corresponding polydisulphide (Z is a bond to another S atom in the molecule). The conversion of the mercapto derivatives to the corresponding polydisulphides is also achieved by oxidation. Examples prepare compounds of Formula I in which X is an anilino group optionally substituted by 1 or 2 -SO 3 Na groups, or X is a morpholino, methylamino, diethanolamino, methoxy, phenoxy, -Cl or group. The compounds of Formula I are optical brighteners for organic materials, e.g. natural or regnerated cellulose, polyamide or polyurethane.