Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-07-16
1995-01-10
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
534772, 534861, 534869, 534642, 534730, 534757, 534764, 534583, 534784, 534785, 534782, 534773, 534821, 534827, 534836, 534837, 534845, 534851, 546294, C07D21172, C07D21184, C07D21362, C07D21369, C09D 2942, C09D 31153
Patent
active
053808592
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a novel benzophenoneazo dye of the formula I ##STR3## where the ring A can be benzofused and a benzofused ring A can be bridged by C.sub.2 H.sub.4, position 3 is unsubstituted or substituted by carbamoyl, C.sub.2 -C.sub.5 -alkanoyl, hydroxysulfonylmethyl or hydroxysulfonyl, or is the radical of a coupling component of the phenylazopyridone, diaminopyridine, imidazolopyridine, aminopyrazole, hydroxypyrazole, aminothiazole, pyrimidine, indole, quinolone, aniline or aminonaphthalene series, radical of a diazo or coupling component, or, when m is 2, is hydrogen, the other hydrogen or hydroxysulfonyl, independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxyethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula one of the two radicals X.sup.1 and X.sup.2 is hydrogen and the other hydroxysulfonyl, independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxyethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula ##STR4## where L.sup.1 is a chemical bond, C.sub.1 -C.sub.4 -alkylene, oxygen or a radical of the formula O--CH.sub.2, O--CH.sub.2 CH.sub.2 --O, O--CH.sub.2 CH.sub.2 CH.sub.2 --O or O--CH(CH.sub.3)CH.sub.2 --O, and X.sup.1, X.sup.2, R.sup.4, K and the ring A are each as defined above, and compounds, to a process for preparing disulfonated pyridone compounds, and to the use of the novel dyes for dyeing natural or synthetic substrates.
The novel benzophenoneazo dyes of the formula I are shown in the form of the free acid. However, their salts are of course also included.
The salts in question are metal or ammonium salts. Metal salts are in particular the lithium, sodium or potassium salts. Ammonium salts suitable for the purposes of the present invention are those salts which have either substituted or unsubstituted ammonium cations. Substituted ammonium cations are for example monoalkyl-, dialkyl-, trialkyl-, tetraalkyl- or benzyltrialkyl-ammonium cations or those cations which are derived from nitrogen-containing five- or six-membered saturated heterocycles, such as pyrrolidinium, piperidinium, morpholinium, piperazinium or N-alkylpiperazinium cations or their N-monoalkyl- or N,N-dialkyl-substituted products. Alkyl here is to be understood as meaning in general straight-chain or branched C.sub.1 -C.sub.20 -alkyl, which can be substituted by hydroxyl groups and/or interrupted by oxygen atoms.
EP-A-302,401 and the earlier patent application EP-A 413 229 disclose benzophenoneazo dyes which, however, have no water-solubilizing group in the molecule.
DE-A-2 223 622 describes a dye with 3-aminobenzophenone-4-sulfonic acid as diazo component and 1-methyl-6-hydroxy-3,4-trimethylenepyrid-2-one as coupling component.
Furthermore, DE-A-3 316 887 describes an azo dye whose coupling component is 1-hydroxysulfonylbenzyl-3-hydroxysulfonyl-4-methyl-6-hydroxypyrid-2-one .
EP-A-154 816 discloses azo dyes with 4-aminobenzophenone as diazo component and diaminopyridines as coupling component.
Finally, EP-A-126 324 describes a phenylazo dye with a sulfonated N-benzylpyridone as coupling component.
It is an object of the present invention to provide novel benzophenoneazo dyes which have at least one hydroxysulfonyl group in the molecule and advantageous application properties.
We have found that this object is achieved by the benzophenoneazo dyes of the formula I defined at the beginning.
Any alkyl or alkylene appearing in the above-mentioned formula I may be either straight-chain or branched.
If substituted phenyl groups appear in the formulae of the dyes of the invention, they generally have from 1 to 3 substituents. Suitable substituents are for example C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen and hydroxysulfonyl.
Coupling components KH of the pyridone or phenylazopyridone series conform for example to the formula IIc
REFERENCES:
patent: 3763170 (1973-10-01), Austin et al.
patent: 3867392 (1975-02-01), Heinrich et al.
patent: 3912744 (1975-10-01), Heinrich et al.
patent: 5153356 (1992-10-01), Lamm et al.
Beichelt Helmut
Lamm Gunther
Schaffer Ortwin
BASF - Aktiengesellschaft
Higel Floyd D.
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