Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
1999-08-26
2001-05-29
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C534S642000, C534S643000
Reexamination Certificate
active
06239263
ABSTRACT:
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. S63-309559(1988), Hei 1-215862 (1989) and Hei 1-245060 (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). Further, 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. Furthermore, the purpose of the present invention is to provide water soluble azo compounds which are excellent in the dye-affinity even in a small amount as compared with a usual one.
The present invention provides novel water-soluble azo compounds prepared using 2-hydroxynaphtdalene-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]:
[wherein, Y is —OM, —OR
1
, or —NH-X, and Y′ is —OM′, —OR
1
′, or —NH-X′, (in which M and M′ each represent a hydrogen atom or an alkali metal;
R
1
and R
1
′ each represent a group selected from an optionally branched 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
X and X′ each represent an optionally substituted aromatic group or an optionally substituted heterocyclic group having conjugated double bonds;
provided that at least one of Y and Y′ represents —OM or —OM′;)
A is a group represented by the formula [IV]
(wherein B and B′ represent a group selected from a group consisting of —SO
2
—, —CO—, —NHSO
2
—, or —NHCO—,
Q and Q′ represent a group bonding the ethyl group at the &bgr;-position and capable of forming a vinyl group by alkaline decomposition; and
m represents an integer 1 or 2, and n represents an integer 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, which comprises diazotizing an amine represented by the general formula [II]:
H
2
N-A [II]
[wherein A is the general formula [IV],
(in which B and B′ represent a group selected from a group consisting of —SO
2
—, —CO—, —NHSO
2
—, or —NHCO—; and
Q and Q′ represent a group bonding the ethyl group at the &bgr;-position and capable of forming a vinyl group by alkaline decomposition;]
m represents an integer 1 or 2, and n represents an integer 1 to 3;)] and coupling the resulting diazonium compound with a compound represented by the general formula [III]:
[wherein Y is —OM, —OR
1
, or —NH-X, and Y′ is —OM′, —OR
1
′, or —NH-X′, (in which M and M′ each represent a hydrogen atom or an alkali metal;
R
1
and R
1
′ each represent a group selected from an optionally branched saturated or unsaturated aliphatic hydrocarbon group having 1 to 6 carbon atoms, an optionally substituted cycloalkyl group having 3 to 6 carbon atoms, or an optionally substituted aromatic group; and
X and X′ each represent an optionally substituted aromatic group or an optionally substituted heterocyclic group having conjugated double bonds;
provided that at least one of Y and Y′ represents —OM or —OM′;)].
As described above, a coupler used in the present invention (a compound represented by the general formula [III]) is characteristically prepared from 2-bydroxynaphthalene-3,6-carboxylic 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 having a carboxyl group at only one of the 3-and 6-positions. In addition, such couplers allow easier regulation of color and vividness by appropriately selecting the carboxyl group or derivatives thereof. Furthermore only a little amount of them can confer deep dyeing.
The carboxylic acids (wherein M or M′ is a hydrogen atom) may be in the form of alkali metal salt (wherein M or M′ is an alkali metal). Specific examples of such alkali metal are sodium, potassium, and lithium.
In the case of esters, i.e., when Y is —OR
1
or Y′ is —OR
1
′, R
1
and R
1
′ represent an optionally branched saturated or unsaturated aliphatic hydrocarbon group having 1 to 6 carbon atoms, preferably an optionally branched saturated alkyl having 1 to 4 carbon atoms, and in particular, for example, methyl or ethyl; a cycloalkyl having 3 to 6 carbon atoms, or an aromatic group, preferably a phenyl, benzyl, or phenacyl group; and the cycloalkyl or aromatic group contained in such group may have also substituent(s). Examples of such substituents are halogen atoms, nitro, lower alkyl, lower alkoxy, cyano, phenyl, morpholino, phenoxy, amide, carboxyl, and sulfo groups.
Amides, i.e., those compounds wherein Y is —NH-X or Y′ is —NH-X′, may be obtained by converting the acid to acid chloride in the usual manner using, for example, thionyl chloride in a solvent such as xylene or sulfolane and then reacting the product with an amine. Alternatively, the same may also be obtained by directly reacting the acid with an amine using phosphorus trichiloride, dicyclohexylcarbodiimide or the like.
Examples of amine, i.e., those compounds which constitute —NH-X or —NH-X′, may include optionally substituted aromatic amino compounds such as aniline (X or X′ is a phenyl group), aminonaphthalene (X or X′ is a naphthyl group), aminoanthracene (X or X′ is an antihyl group), aminopyrene (X or X′ is a pyrenyl group), aminofluorene (X or X′ is a fluorenyl group) and aminoanthaquinone (X or X′ is an anthraquinonyl group), optionally substituted heterocyclic amio compounds having conjugated double bonds such as aminobenzimidazolone (X or X′ is a benzimidazolonyl group), aminocarbazole (X or X′ is a carbanoly) group), ammo pyridine (X or X′ is a pyridyl group), aminothiazole (X or X′ is a ihiazolyl group), aminobenzothiazole (X or X′ is a benzothiazolyl group), and aminoimidazole (X or X′ is an imidazolyl group), as well as aminoindole, aminothiophene, aminophcnothiazine, aminoacridine, aminoquinoline and the like. Examples of substituent on such compounds include halogen atoms, nitro, sulfo, lower alkyl, lower alkoxy, cyano, phenyl, morpholino, phenoxy, carboxyl, amide (e.g., phenylairnocarbonyl) groups, and sulfonyl (e.g., sulfatoethylsulfonyl), and such phenoxy or amide group may have additional substituent(s). Examples of such additional substituent are halogen atoms, lower aIkyl, lower alkoxy, alkylaminosulfonyl, and cyano groups.
A water-soluble azo compound of the present invention may be obtained by diazotizing an amine represented by the general formula [II] using sodium nitrite or other agents, and coupling the d
Kitayama Masaya
Kittaka Masaharu
Minami Kenji
Ueno Ryuzo
Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
Powers Fiona T.
Sughrue Mion Zinn Macpeak & Seas, PLLC
LandOfFree
Water-soluble azo compounds and process for the preparation... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Water-soluble azo compounds and process for the preparation..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Water-soluble azo compounds and process for the preparation... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2513936