Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1998-06-05
2000-06-06
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534854, 534820, 534811, 548145, 5483054, 562451, 562455, 564153, C07C23566, C07C23102, C07D27110, C07D40312
Patent
active
060720425
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a bis (aminocarbonylnaphthol) derivative which is useful as a raw material of an azo compound, and a process for producing the same.
BACKGROUND OF THE INVENTION
Recently, novel pigments and dyes have been developed, intensively, in order to improve paint, ink and photosensitive materials, etc. by imparting higher addition value and better characteristics, particularly light resistance, solvent resistance, water resistance, chemical resistance, etc. in comparison with the prior art. As a specific example thereof, an azo compound from bisamide of 2-hydroxynaphthalene-6-carboxylic acid as a raw material has already been known (e.g. Japanese Patent Kokai Publication No. Hei 7-238231).
DISCLOSURE OF THE INVENTION
The present invention provides a novel compound whose utility is more expected as a raw material for azo compound.
The present invention provides a bisamide compound obtained from 2-hydroxynaphthalene-3, 6-dicarboxylic acid as a raw material. It is expected that an azo pigment using the compound as a coupler shows excellent chemical resistance, water resistance and solvent resistance.
Namely, the present invention relates to a bis (aminocarbonylnaphthol) derivative represented by the general formula [I], [II] or [III]: ##STR1## [wherein Y represents --(CONH)n--X or --COR; Y' represents--(CONH)n--X' or --COR'; substituted aromatic group or an optionally substituted heterocyclic group having a conjugated double bond; an optionally branched alkoxyl group having 1 to 6 carbon atoms, a benzyloxy group, a phenoxy group or a phenacyloxy group; alkyl group having 1 to 6 carbon atoms, an optionally branched acyl group having 1 to 6 carbon atoms or a phenylalkyl group; atoms, an optionally branched alkoxyl group having 1 to 6 carbon atoms, a halogen atom, a nitro group or a nitroso group; atoms, or a cyclic group having a conjugated double bond].
The compound of the present invention is characterized in the bisamidation of one of carboxyl groups of naphthol having carboxyl groups at the 3- and 6-positions, using an aliphatic or aromatic diamine.
The present invention also relates to a process for producing a bis(aminocarbonylnaphthol)derivative represented by the general formula [I], [II] or [III]: ##STR2## [wherein Y, Y', R.sub.2, R.sub.2 ', Q, Q', m, m' and A are as defined above], which comprises reacting compounds represented by the general formulas [VII] [VII'] and/or [VIII] [VIII']: ##STR3## [wherein Y, Y', R.sub.2, R.sub.2 ', Q, Q', m, and m' are as defined above; and R" represents a hydroxyl group or a halogen atom.] with diamines represented by the general formula [IX]:
The present invention also relates to a process for producing bis(aminocarbonylnaphthol) derivative represented by the general formula [I], [II] or [III]: ##STR4## [wherein Y, Y', R.sub.2, R.sub.2 ', Q, Q', m, m' and A are as defined above], which comprises reacting a compound represented by the general formula [VII] or [VII']: ##STR5## [wherein Y, R.sub.2, Q and m are as defined above; and R" represents a hydroxyl group or a halogen atom] with nitroamines represented by the general formula [X]:
[wherein A is as defined above], converting the nitro group of the obtained compounds to an amino group to give an amine derivative represented by the general formula [XI] or [XI']: ##STR6## [wherein Y, R.sub.2, Q and m are as defined above], and then reacting it with the compounds represented by the general formula [VIII] or [VIII']: ##STR7## [wherein Y', R.sub.2 ', Q' and m' are as defined above; and R" represents a hydroxyl group or a halogen atom].
The compound constituting a group X or X' in Y and Y' includes optionally substituted aromatic group, such as phenyl group, naphthyl group, anthraquinonyl group, etc.; or optionally substituted heterocyclic group having a conjugated double bond, such as benzimidazolonyl group, carbazoryl group, pyridyl group, thiazolyl group, benzothiazolyl group, imidazolyl group, indolyl group, thionyl group, phenothiazinyl group, acridinyl group, quinolinyl
REFERENCES:
patent: 1579121 (1926-03-01), Krizikalla et al.
patent: 2195443 (1940-04-01), Benade
patent: 5071967 (1991-12-01), Hari et al.
patent: 5298609 (1994-03-01), Hari
Kitayama Masaya
Minami Kenji
Tanigawa Mariko
Tanikawa Katsunori
Ueno Ryuzo
Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
Powers Fiona T.
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