Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1998-11-18
1999-12-21
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534657, 534689, 534797, 534812, 534820, 106 3146, 106 3152, 106 3181, 106 3178, 106496, 524 89, 524 91, 524 95, 524105, 524111, 524190, 548261, 5482684, 548305, 5483054, 548444, 549480, 560 45, 564153, C09B 33147, C09B 6720, C09D 1100, C09D 712, C08J 320, G03G 506
Patent
active
060050853
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to novel condensed azo compounds and a process for preparing the same.
BACKGROUND OF THE INVENTION
In recent years, novel pigments, dyes and the like have been actively developed in order to improve, for example, paints, inks, photosensitive materials by providing them with high added values or superior properties, in particular superior light resistance, solvent resistance, water resistance, and/or chemical resistance. As exempla of such compounds, condensed azo compounds prepared from bisamides of 2-hydroxynaphthalene-3-carboxylic acid (e.g., Chromophthal Scarlet RN or BRN, The Japanese Patent Publication No. S48-11205 B (1973)), and condensed azo compounds prepared from bisamides of 2-hydroxynaphthalene-6-carboxylic acid (e.g., The Japanese Patent Publication No. H7-238231 A (1995)) are already known.
DISCLOSURE OF THE INVENTION
The present invention is characterized in that it provides azo coloring materials having excellent properties such as excellent water resistance, chemical resistance, solvent resistance, and heat resistance. Furthermore, the present invention aims to provide a series of azo compounds of which color and vividness can be regulated by appropriately selecting the substituents on the molecules.
The present invention provides novel condensed azo compounds using bisamide compounds prepared from 2-hydroxynaphthalene-3,6-dicarboxylic acid as couplers, as well as coloring materials comprising the same, and a process for preparing said condensed azo compounds. In particular, the present invention relates to a condensed azo compound represented by the general formula [I], [II], or [III]: ##STR1## wherein, Y represents --(CONH).sub.n --X or --COR; Y' represents --(CONH).sub.n --X' or --COR'; atoms, an optionally substituted aromatic group, or an optionally substituted heterocyclic group having conjugated double bonds; group of 1-30 carbon atoms, a benzyloxy group, a phenyloxy group, or a phenacyloxy group, provided that if one of R and R' is a hydroxyl group, then it may form an acceptable salt; branched alkyl group of 1-6 carbon atoms, an acyl group of 1-6 carbon atoms, or a phenylalkyl group; atoms, an optionally branched alkoxy group of 1-6 carbon atoms, a halogen atom, a nitro group, or a nitroso group; 1, then Q or Q' may bind to either of the two fused rings, and if m or m' is 2 or 3, then Q or Q' may bind to one or both of the fused rings or may form a ring together with the two fused rings; a cyclic group having conjugated double bonds; and group, comprising such condensed azo compound. The azo compound of the present invention has non-condensed amide group(s), hydroxyl group(s), or alkoxy group(s), and in particular when the amide group is an aromatic amide group, color and vividness of the compound can be regulated by introducing an appropriate substituent(s) into such aromatic group. As used herein, the term "coloring materials" refers to, for example, dyes, pigments, inks, paints, printing inks, and organic photoconductive materials.
Furthermore, the present invention relates to a process for preparing a condensed azo compound represented by the general formula [I], [II], or [III]: ##STR2## wherein, Y represents --(CONH).sub.n --X or --COR; Y' represents --(CONH).sub.n --X' or --COR'; atoms, an optionally substituted aromatic group, or an optionally substituted heterocyclic group having conjugated double bonds; group of 1-30 carbon atoms, a benzyloxy group, a phenyloxy group, or a phenacyloxy group, provided that if one of R and R' is a hydroxyl group, then it may form an acceptable salt; branched alkyl group of 1-6 carbon atoms, an acyl group of 1-6 carbon atoms, or a phenylalkyl group; atoms, an optionally branched alkoxy group of 1-6 carbon atoms, a halogen atom, a nitro group, or a nitroso group; 1, then Q or Q' may bind to either of the two fused rings, and if m or m' is 2 or 3, then Q or Q' may bind to one or both of the fused rings or may form a ring together with the two fused rings; a cyclic group having conjugated dou
REFERENCES:
patent: 3658785 (1972-04-01), Ronco et al.
patent: 4051121 (1977-09-01), Tcherkinsky et al.
patent: 4053464 (1977-10-01), Roueche
patent: 4247614 (1981-01-01), Ohta et al.
Kitayama Masaya
Minami Kenji
Tanikawa Katsunori
Ueno Ryuzo
Wakamori Hiroyuki
Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
Powers Fiona T.
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