AZO compounds and process for producing the same

Details AZO compounds and process for producing the same AZO compounds and process for producing the same

2000-06-16

2002-06-25

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031480, C106S031500, C106S031770, C106S031790, C106S031800, C106S496000, C106S506000, C106S799000, C106S807000, C106S807000, C106S807000, C106S506000, C106S157900

Reexamination Certificate

active

06409812

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a novel azo compound, a process for producing the same and use of the same. The present invention also relates to a novel naphthol derivative, which can be a starting material for synthesis of the novel azo compound of the present invention.
BACKGROUND ART
In order to provide or improve paints, inks, photosensitive materials and the like with added value or higher properties, especially to provide those with light resistance, solvent resistance, water resistance and chemical resistance, development of novel pigment or dyes have been intensively conducted. For example, the inventors had already disclosed an azo compound synthesized by using 2-hydroxynaphthalene-3,6-dicarboxylic acid, or its ester, amide or ureido derivative as a coupler(WO98/16587).
SUMMARY OF INVENTION
The present invention provides an azo compound, which exhibits outstanding water resistance, chemical resistance, thermal resistance, and especially light resistance, good dispersion property and coloring power and can provide wide range of bright color from orange to purple with excellent transparency.
The present invention provides a novel azo type coloring agent obtained by modifying 3- and/or 6-carboxy group of 2-hydroxynaphthalene-3,6-dicarboxylic acid with an alkylamide derivative. The azo compound of the present invention exhibits an excellent light resistance.
Accordingly, the present invention relates to a novel azo compound having the general formula (I):
wherein Y is —(CONH)n-X or an optionally esterified carboxyl group,
Y′ is —(CONH)n-X′ or an optionally esterified carboxyl group,
(wherein X and X′ are optionally substituted and/or branched saturated or unsaturated aliphatic hydrocarbon groups, optionally substituted aromatic groups, or optionally substituted heterocyclic groups having conjugated double bonds,
n is an integer of 1 or 2,
provided that when either Y or Y′ is a carboxylic group, said carboxylic group may optionally form an acceptable salt),
R
2
is a hydrogen atom, an optionally branched alkyl group having 1-6 carbon atoms, an acyl group having 1-6 carbon atoms or a phenyl alkyl group,
Q is an optionally branched alkyl group having 1-6 carbon atoms, an optionally branched alkoxy group having 1-6 carbon atoms, a halogen atom, a sulfo group, a nitro group, a nitroso group, or an amino group,
m is an integer of 0-3, provided that when m is 1, the Q may be combined with either of the two condensed rings, when m is 2 or 3, the Qs may be combined with either or both of the condensed rings, or may form a ring together with the two condensed rings,
Z is an optionally substituted monovalent aromatic group, and
provided that at least one of Y and Y′ represents a group wherein X or X′ is an optionally substituted and/or branched unsaturated or saturated aliphatic hydrocarbon group;
a process for producing the same, and coloring composition comprising the azo compound of the present invention. According to the present application, the term “coloring composition” include pigment, ink, paint, dye, mass-coloring agent for polymer material and charge generating material, and the like.
The present invention also provides a novel naphthol derivative having the general formula (IV):
wherein Y is —(CONH)n-X or an optionally esterified carboxyl group,
Y′ is —(CONH)n-X′ or an optionally esterified carboxyl group,
(wherein X and X′ are optionally substituted and/or branched saturated or unsaturated aliphatic hydrocarbon groups, optionally substituted aromatic groups, or optionally substituted heterocyclic groups having conjugated double bonds,
n is an integer of 1 or 2,
provided that when either Y or Y′ is a carboxylic group, said carboxylic group may optionally form an acceptable salt),
R
2
is a hydrogen atom, an optionally branched alkyl group having 1-6 carbon atoms, an acyl group having 1-6 carbon atoms or a phenyl alkyl group,
Q is an optionally branched alkyl group having 1-6 carbon atoms, an optionally branched alkoxy group having 1-6 carbon atoms, a halogen atom, a sulfo group, a nitro group, a nitroso group, or an amino group,
m is an integer of 0-3, provided that when m is 1, the Q may be combined with either of the two condensed rings, when m is 2 or 3, the Qs may be combined with either or both of the condensed rings, or may form a ring together with the two condensed rings, and
provided that at least one of Y and Y′ represents a group wherein X or X′ is an optionally substituted and/or branched unsaturated or saturated aliphatic hydrocarbon group.
As described above, the coupler used in this invention, i.e. the compound represented by the general formula [IV], may be synthesized from 2-hydroxynaphthalene-3,6-dicarboxyamide, or ureide or carboxylic acid derivative thereof. The starting material, 2-hydroxynaphthalene-3,6-dicarboxylic acid may be obtained by means of Kolbe-Schmitt reaction, i.e. by reacting potassium 2-hydroxynaphthalene with carbon dioxide in the presence of a potassium salt such as potassium phenoxide under high pressure and high temperature.
In the present invention, the amide or ureide derivative may be prepared by obtaining acid chloride of the starting compound by means of thionyl chloride or the like in a solvent such as xylene or sulfolane in a conventional manner, and then reacting the acid chloride with amine or urea. Alternatively, they can be prepared by reacting the starting compound directly with amine or urea in the presence of phosphorous trichloride, dicyclohexylcarbodiimide or the like.
Examples of the amines or ureas, starting materials which constitutes the group X or X′ in the Y or Y′ may include optionally substituted and/or branched saturated or unsaturated aliphatic amines, optionally substituted aromatic amino compounds such as aniline (X or X′ is a phenyl group), amino naphthalene (X or X′ is a naphthyl group), aminoanthracene (X or X′ is a anthryl group), aminopyrene (X or X′ is a pyrenyl group), amino fluorene (X or X′ is a fluororenyl group) or aminoanthraquinone (X or X′ is an anthraquinonyl group); and optionally substituted heterocyclic compounds having conjugated double bond(s) such as aminobenzimidazolone (X or X′ is a benzimidazolonyl group), aminocarbazole (X or X′ is a carbazolyl group), aminopyridine (X or X′ is a pyridyl group), aminothiazole (X or X′ is a thiazolyl group), aminobenzothiazole (X or X′ is a benzothiazolyl group), or aminoimidazole (X or X′ is an imidazolyl group) as well as aminoindole (X or X′ is an indolyl group), aminothiophene (X or X′ is a thiofuryl group), aminophenothiazine (X or X′ is a phenothiazinyl group), aminoacridine (X or X′ is an acridinyl group), and aminoquinoline (X or X′ is a quinolinyl group). Examples of the substituents include halogen atoms, nitro group, lower alkyl groups, lower alkoxy groups, cyano groups, phenyl groups, morpholino groups, phenoxy groups, sulfo groups, carboxyl groups, amide groups (for example, phenylaminocarbonyl group) and the like, and the phenoxy and amide groups may also have another substituent such as halogen atom, lower alkyl group, lower alkoxy group, alkylaminosulfonyl group, nitrile group or the like.
In the present invention, at least one of Y and Y′ in the compound of the formulae [I] and [IV] represents a group wherein X or X′ is an optionally substituted and/or branched saturated or unsaturated aliphatic hydrocarbon group.
Ureas may be prepared by reacting the above-described amino compound with potassium cyanate. That is, for example, phenylurea may be obtained from aniline. Y or Y′ may represent an optionally esterified carboxyl group, for example those represent by the general formula of —COR or —COR′. When either R or R′ is a hydroxy group, it may form an acceptable salt. The term “an acceptable salt” represents a salt, which does not impair diazotizing reaction and does no

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