Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1986-02-28
1989-04-11
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534602, 534603, 534604, 534606, 534612, 534615, 534629, 534641, 534642, 534588, 534887, 534589, C09B 62507, C09B 6251, C09B 62513, C09B 62515
Patent
active
048208060
DESCRIPTION:
BRIEF SUMMARY
The invention relates to water-soluble azo compounds which contain basic groups and are free from sulphonic acid groups which compounds are metal-free or are in 1:1 or 1:2 metal complex form. These compounds are suitable for use as dyestuffs.
According to the invention there is provided monoazo and disazo compounds in metal-free form or in 1:1 or 1:2 metal complex form which in metal-free form correspond to formula I tetrahydronaphthalene series, pyrazol-5-one, pyridine, pyridone, barbituric acid, quinoline, isoquinoline, benzene- or naphthalene- or tetrahydronaphthalene-azo-benzene or -azo-naphthalene, or of the acetoacetamide series, quaternary ammonium group, a hydrazinium group or a ternary sulphonium group, bound to the carbon atom of a triazine or pyrimidine group which therefore constitutes part of a fibre-reactive grouping is excluded; formed by the addition of dilute aqueous organic or mineral acids, and mixtures of compounds of formula I.
Preferably, D is the radical of a diazo component of the benzene or naphthalene series in which the group --W.sub.1 --SO.sub.2 CH.dbd.CH.sub.2 is preferably bound in the 3- or 4-position of any phenyl group; on any naphthyl group --W.sub.1 --SO.sub.2 CH.dbd.CH.sub.2 is particularly preferred in the 4-position. D is further unsubstituted or may contain one or two further substituents conventional in the chemistry of fibre-reactive azo compounds (with the exception of sulphonic acid groups) including any metallisable substituent in the ortho position to a carbon atom bound to the azo group, such as a hydroxy, amine, substituted amine, methoxy or carboxy group.
K is preferably the radical of a coupling component of the aminobenzene, phenol, aminophenol, aminonaphthalene, naphthol or aminonaphthol series or of the naphthalene series containing any other substituent enabling the coupling; of the 1-arylpyrazol-5-one, aminopyridine, hydroxypyridone, barbituric acid, N-alkyl or N-aryl substituted acetoacetamide, benzene- or naphthalene-azo-benzene, benzene-azo-naphthalene or tetrahydronaphthalene-azo-benzene series.
Additionally to the n groups --W.sub.2 --Z K is further unsubstituted or may contain one or two further substituents conventional in the chemistry of basic azo compounds including those substituents which enable the metallisation and therefore are in the ortho position to a carbon atom bound to the azo group.
n is preferably 1 or 2.
W.sub.1 is preferably a direct bond; a C.sub.1-6 alkylene or C.sub.2-6 alkenylene group which groups are straight chain or branched, unsubtituted or monosubstituted by hydroxy, halogen, cyano, C.sub.1-4 alkoxy or phenyl and in which the carbon chains may be interrupted by one or two hetero atoms; --CONH--X--, --CO--X--, --SO.sub.2 NH--X--, --NHCO--x--, --NH--X-- or --NHNHCO--X--, in which X is C.sub.1-6 alkylene or C.sub.2-6 alkenylene and which groups are bound to the --SO.sub.2 -- group by a carbon atom of X; --CH.sub.2 CONHCH.sub.2 -- or --CH.sub.2 NHCOCH.sub.2 --.
Each W.sub.2, independently, has preferably one of the significances of W.sub.1 except a direct bond where Z is attached to a carbon atom of X.
Each Z, independently, is preferably a water-solubilising protonatable amino group or a quaternary ammonium group; preferably Z is a primary amino group, a secondary or tertiary aliphatic, cycloaliphatic, aromatic or saturated or partially unsaturated heterocyclic amino group in which latter group the N-atom or a carbon atom is attached to W.sub.2 ; or a quaternary ammonium group corresponding to the above.
In the specification any halogen means fluorine, chlorine, bromine or iodine, preferably chlorine or bromine.
The term "basic groups" also includes quaternary ammonium groups, hydrazinium groups and ternary sulphonium groups.
Any alkyl, alkylene or alkenylene present may be 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, alkylene or alkenylene group which is attached to a nitrogen atom the hydroxy g
REFERENCES:
patent: 3939141 (1976-02-01), Meininger et al.
patent: 3998805 (1976-12-01), Koller et al.
patent: 4000966 (1977-01-01), Meininger et al.
patent: 4002606 (1977-01-01), Schlafer et al.
Baumann Werner
Diest Joseph V.
Eichenberger Herbert
Oppliger Max
Higel Floyd D.
Kassenoff Melvyn M.
Sandoz Ltd.
Sharkin Gerald D.
Vila Richard E.
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