Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1985-02-08
1987-08-11
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
162162, 534567, 534582, 534602, 534604, 534608, 534612, 534710, 534728, 534740, 534756, 534760, 534764, 534772, 534775, 534776, 544181, 544198, C09B 3147, C09B 3508, C09B 4526, C09B 4408
Patent
active
046862854
DESCRIPTION:
BRIEF SUMMARY
The invention relates to heterocyclic compounds containing basic and/or cationic groups suitable for use as dyestuffs and to intermediates for making such dyestuffs.
According to the invention there is provided compounds which, in one of the possible tautomeric forms, correspond to formula I, ##STR2## which compounds may be in salt form or acid addition salt form and mixtures of such compounds, aliphatic, cycloaliphatic, aromatic or heterocyclic amine group or a heterocyclic amine group in which the nitrogen atom is part of the heterocycle which contains one to three hetero atoms and which may be further substituted by up to three C.sub.1-4 alkyl groups; a group Z or a radical which, in one of the possible tautomeric forms, corresponds to formula II, ##STR3## each Z, independently, is an N-bonded organic radical containing 1 to 5 nitrogen atoms of which at least one nitrogen atom has basic character or forms an ammonium cation, --COOR.sub.3, --CONR.sub.4 R.sub.5 or --COZ, and R.sub.5, independently, is hydrogen; C.sub.1-4 alkyl; phenyl(C.sub.1-4 alkyl), the phenyl group of the latter two substituents being unsubstituted or substituted by one or two groups selected from methyl, ethyl, methoxy and ethoxy; or cyclohexyl, -phenylene, in which each of the aromatic rings may be substituted by one or two groups selected from halogen, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, carboxy and sulpho, X.sub.a is a direct bond or a divalent bridging group, electron attracting group on the side which is attached to W, ##STR4## R.sub.6 is hydrogen; C.sub.1-4 alkyl; C.sub.2-4 alkyl monosubstituted by hydroxy, cyano, chlorine or C.sub.1-4 alkoxy; phenyl(C.sub.1-4 alkyl) or cyclohexyl; contain further azo groups, 2 when R.sub.o is --N.dbd.N--T--N.dbd.N--; polyazo compounds, in metal-free or in 1:1 or 1:2 metal complex form and are free from anionic groups or may contain anionic groups in addition to basic and/or cationic groups.
In the specification halogen means fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, especially chlorine.
Any alkyl, alkylene or alkenylene present is linear or branched unless indicated otherwise. The alkyl group of any alkoxy group is linear or branched unless indicated to the contrary.
In any hydroxy-substituted alkyl group which is linked to a nitrogen atom, the hydroxy group is bound to a carbon atom other than to the C.sub.1 -atom.
R.sub.1 is preferably O or NH; most preferably it is O.
R.sub.3 is preferably R.sub.3a where R.sub.3a is hydrogen, methyl or ethyl.
R.sub.4 and R.sub.5 are preferably R.sub.4a and R.sub.5a where each of R.sub.4a and R.sub.5a, independently, is hydrogen, methyl, ethyl, 2-hydroxyethyl, benzyl or cyclohexyl; most preferably, R.sub.4 and R.sub.5 are hydrogen.
R.sub.2 is preferably R.sub.2a where R.sub.2a is methyl, ethyl, methoxy, ethoxy, --COOR.sub.3a, --CONH.sub.2 or --COZ; more preferably, it is R.sub.2b where R.sub.2b is methyl, --COOH, --COOCH.sub.3, --CONH.sub.2 or --COZd, wherein Zd is defined below; most preferably, R.sub.2 is methyl.
A is preferably unsubstituted 1,3- or 1,4-phenylene.
The bridging group X is preferably C.sub.1-6 alkylene, --C*ONHC.sub.1-6 alkylene or --S*O.sub.2 NHC.sub.1-6 alkylene in which the * denotes the atom attached to the --A--.sub.a group.
a is preferably 1; x is preferably 0.
W is preferably --NH--, --NCH.sub.3 -- or ##STR5## especially --NH--.
Z is preferably a group of the formula ##STR6## in which each R.sub.7 is independently hydrogen or C.sub.1-4 alkyl, each of R.sub.8 and R.sub.9 is independently hydrogen; C.sub.1-6 alkyl; C.sub.2-6 alkyl monosubstituted by hydroxy or cyano; phenyl(C.sub.1-3 alkyl), the phenyl group of which is unsubstituted or substituted by one to three groups selected from chlorine, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; C.sub.5-6 cycloalkyl unsubstituted or substituted by one to three C.sub.1-4 alkyl groups, or attached, form a 5- or 6-membered saturated or unsaturated ring which contains one to three hetero atoms, noncyclic significances of R.sub.8 and R.sub.9 except hydrogen, a
REFERENCES:
patent: 4273707 (1981-06-01), Pedrazzi
patent: 4550158 (1985-10-01), Doswald et al.
Higel Floyd D.
Kassenoff Melvyn M.
Sandoz Ltd.
Sharkin Gerald D.
Vila Richard E.
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