Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1998-06-22
1999-10-12
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534689, 534763, 534797, 534812, 534819, 534813, 534DIG4, 106 3181, 106496, 430 72, 524190, C09B 35023, C09B 35033, C09D 1100, C08J 320
Patent
active
059657154
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a novel bisazo compound and a process for producing the same.
BACKGROUND OF THE ART
Azo compounds are useful as dyes, pigments, carrier generation materials and the like, and a large number of such compounds have been provided for many years. Particularly in recent years, many compound suitable for OPC have been developed. For example, a highly sensitive and highly durable carrier generation material which uses a hydroxynaphthalenedicarboxyimide as a coupler has been proposed in Japanese Patent Publication No. 95-234530 A. The imide proposed in this Patent Publication is 2-hydroxynaphthalene-4,5-dicarboxyimide.
DISCLOSURE OF THE INVENTION
The feature of the present invention is to provide a bisazo-coloring material which is superior in resistance to water, chemical agents, solvents, heat and the like.
The present invention provides a novel bisazo compound each of which has two azo groups in its molecule and which uses a 2-hydroxynaphthalene-3,6-dicarboxylic acid, ester, amide, or ureide derivative as a coupler, as well as a coloring matirial comprising the same, and a method for producing said bisazo compounds. Thus, the present invention provides a bisazo compound represented by the following general formula [I]: following general formula [II]: ##STR1## (wherein, Y is --(CONH)n--X or --COR, substituted aromatic group or an optionally substituted heterocyclic group having a conjugated double bond), optionally branched alkoxy group having 1-6 carbon atoms, a benzyloxy group, a phenoxy group, or a phenacyloxy group, having 1-6 carbon atoms, an acyl group having 1-6 carbon atoms or a phenylalkyl group; optionally branched alkoxy group having 1-6 carbon atoms, a halogen atom, a nitro group or a nitroso group, and m represents an integer from 0 to 3, and when one of R and R' represents a hydroxy group, it may optionally form an acceptable salt; specification, the term "coloring material" refers to dyes, pigments, inks, paints, printing inks, carrier generation materials and the like.
The present invention further relates to a process for producing said bisazo compound in which process a compound represented by the general formula [VI]: diazotized, and the bisdiazonium compound so obtained is coupled with a compound represented by the general formula [VII]: ##STR2## [wherein, Y is --(CONH)n--X or --COR, substituted aromatic group or an optionally substituted heterocyclic group having a conjugated double bond, optionally branched alkoxy group having 1-6 carbon atoms, a benzyloxy group, a phenoxy group, or a phenacyloxy group, having 1-6 carbon atoms, an acyl group having 1-6 carbon atoms or a phenylalkyl group; optionally branched alkoxy group having 1-6 carbon atoms, a halogen atom, a nitro group or a nitroso group, and m represents an integer from 0 to 3]. a metal compound, when at least one of R and R' is a hydroxy group.
As described above, a coupler in the invention (a group represented by the general formula [II] or a compound represented by [VII]) is prepared from 2-hydroxynaphthalene-3,6-dicarboxamide, carbonylurea or carboxylic acid derivative as a raw material. The raw material, 2-hydroxynaphthalene-3,6-dicarboxylic acid may be obtained by the Kolbe-Schmitt method of reacting carbon dioxide with potassium 2-naphtholate under a high pressure and at a high temperature in the presence of a potassium salt such as potassium naphthol.
The amide or ureide may be obtained by preparing an acid chloride according to a conventional method, for example, using thionyl chloride in a solvent such as sulfolane, and by reacting it with amines or ureas. Alternatively, the same may also be obtained by directly reacting with amines or ureas using phosphorous trichloride or dicyclohexylcarbodiimide.
Examples of the amines or ureas, that is, a compound which constitutes X or X' in Y and Y', include an optionally substituted aromatic amino compound such as aniline (X or X' is a phenyl group), .alpha.- or .beta.-aminonaphthalene (X or X' is a naphthyl group), or aminoanth
REFERENCES:
patent: 3877957 (1975-04-01), Bradley et al.
patent: 4663442 (1987-05-01), Ohta
patent: 4737430 (1988-04-01), Kinoshita et al.
patent: 5459247 (1995-10-01), Hashimoto
Hasegawa et al., Chemical Abstracts, 107:68100 (1987).
Kitayama Masaya
Minami Kenji
Ueno Ryuzo
Wakamori Hiroyuki
Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
Powers Fiona T.
LandOfFree
Bisazo compounds and process for the preparation thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Bisazo compounds and process for the preparation thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Bisazo compounds and process for the preparation thereof will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-653937