Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1999-03-22
2000-02-01
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534638, 534642, C09B 62008, C09B 62085, D06P 1382
Patent
active
060204702
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to novel water-soluble azo compounds and a process for preparing the same.
BACKGROUND ART
In recent years, novel pigments, dyes and the like have been actively developed in order to provide them with high added values or improved properties. Dyes are color materials having affinities for fibers, i.e., color materials having dyeing abilities, and therefore they are required to have solubility somehow or other. In that context, water-soluble azo compounds have been developed as azo dyes. As specific examples of such water-soluble azo compounds, those prepared from 2-hydroxynaphthalene-6-carboxylic acid (see, for example, the Japanese Patent Publication (Kokai) Nos. H1-215862 (1989) and H1-245060 (1989)) are known.
DISCLOSURE OF THE INVENTION
The present invention is characterized in that it provides water-soluble azo compounds having excellent dyeing properties and fastness (fastness to washing, light, rubbing, perspiration and the like). Furthermore, the present invention aims to provide water-soluble azo compounds of which color and vividness can be regulated by appropriately selecting the substituents on the molecules.
The present invention provides novel water-soluble azo compounds prepared using 2-hydroxynaphthalene-3,6-dicarboxylic acid or an ester or amide derivative thereof as a coupler, and dyes comprising the same, as well as a process for preparing such water-soluble azo compounds.
In particular, the present invention relates to a water-soluble azo compound represented by the general formula [I]: ##STR1## [wherein, Y is --OM, --OR1, or --NH--X and Y' is --OM', --OR1', or --NH--X', (in which M and M' each represent a hydrogen atom or an alkali metal; saturated or unsaturated aliphatic hydrocarbon group having 1 to 6 carbon atoms, an optionally substituted cycloalkyl group having 3 to 6 carbon atoms, and an optionally substituted aromatic group; and optionally substituted heterocyclic group having conjugated double bonds; ##STR2## (in which R2, R3 and R4 each represent a hydrogen atom or a halogen atom; and W1 and W2 each represent a hydrogen atom, a halogen atom, or a group selected from ##STR3## (in which the aromatic rings may optionally have further substituent(s);) m1 and m2 each represent an integer 1 or 2, and n1 and n2 each represent an integer from 1 to 3;)] and to dyes comprising such water-soluble azo compounds.
The present invention further relates to a process for preparing a water-soluble azo compound, the process being characterized in that an amine represented by the general formula [II]: ##STR4## [wherein p represents an integer 1 or 2; Z is ##STR5## (in which R2, R3 and R4 each represent a hydrogen atom or a halogen atom; and W1 and W2 each represent a hydrogen atom, a halogen atom, or a group selected from ##STR6## (in which the aromatic rings may optionally have further substituent(s);) m1 and m2 each represent an integer 1 or 2, and n1 and n2 each represent an integer from 1 to 3;)] is diazotized, and the resulting diazonium compound is coupled with a compound represented by the general formula [III]: ##STR7## [wherein Y is --OM, --OR1, or --NH--X, and Y' is --OM', --OR1', or --NH--X', (in which M and M' each represent a hydrogen atom or an alkali metal; saturated or unsaturated aliphatic hydrocarbon group having 1 to 6 carbon atoms, an optionally substituted cycdoalyl group having 3 to 6 carbon atoms, and an optionally substituted aromatic group; and optionally substituted heterocyclic group having conjugated double bonds;
As described above, a coupler used in the present invention (a compound represented by the general formula [III]) is characteristically prepared from 2-hydroxynaphthalene-3,6-dicarboxylic acid, or an ester or amide derivative thereof. Since such couplers have carboxyl groups or derivatives thereof at both of the 3 and 6-positions, they can confer superior dyeing properties and fastness (fastness to washing, rubbing, perspiration and the like) on the dyes, compared to hydroxynaphthalenemonocarboxylic acids h
Kitayama Masaya
Kittaka Masaharu
Minami Kenji
Ueno Ryuzo
Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
Powers Fiona T.
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