JP2003286420A - Aqueous ink - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an aqueous ink having a clear hue and excellent in light resistance. <P>SOLUTION: The aqueous ink contains a compound represented by general formula (1) or a salt thereof. [wherein R<SB>1</SB>-R<SB>4</SB>are each independently a hydrogen atom, halogen atom, alkyl group aryl group, -COOH, -SO<SB>3</SB>H, -CONR<SB>7</SB>R<SB>8</SB>(wherein R<SB>7</SB>and R<SB>8</SB>are each independently a hydrogen atom, alkyl group, aryl group or a heterocyclic group, and may form a ring with an alkylene group), or -SO<SB>2</SB>R<SB>9</SB>R<SB>10</SB>(wherein R<SB>9</SB>and R<SB>10</SB>are each independently a hydrogen atom, alkyl group, aryl group or a heterocyclic group, and R<SB>7</SB>and R<SB>8</SB>may form a ring with an alkylene group), R<SB>5</SB>is a methyl group or -COOH, R<SB>6</SB>is an alkyl group or an aryl group, but at least one of R<SB>1</SB>-R<SB>4</SB>is -COOH]. <P>COPYRIGHT: (C)2004,JPO

Description

DETAILED DESCRIPTION OF THE INVENTION [0001] BACKGROUND OF THE INVENTION 1. Field of the Invention
The present invention relates to an aqueous ink having light fastness. [0002] 2. Description of the Related Art Writing instruments or ink jet recording methods
Aqueous ink used for recording such as formulas is basically
It is composed of dyes, water and organic solvents, but has
Use water as the main solvent for safety considerations for the body and surrounding environment.
Water-based ink is the mainstream. Also, as a dye
In general, acid dyes, basic dyes, reactive dyes, and
And water-soluble dyes such as direct dyes. [0003] These dyes and aqueous inks have various characteristics.
Is required. In particular, inkjet recording
The aqueous ink used for the recording liquid includes the following
There are various required characteristics. That is, (1) Ink viscosity, surface tension, specific conductivity, density, pH
Physical property values such as (2) Good long-term storage stability of the ink (3) High dissolution stability of dissolved components, nozzle clogging
Don't let (4) Good quick-drying property on the recording material (5) The recorded image is clear and has good light fastness and water fastness
Being And so on. Various studies have been made to satisfy these characteristics.
Have been. For example, in JP-A-2-153977,
Formula (2) (Formula 2) to (5) (Formula 5) as a low dye
Has proposed an ink containing the pyridone azo compound shown
You. [0004] Embedded image [0005] Embedded image [0006] Embedded image [0007] Embedded image However, these compounds have clear hues.
Despite its low light resistance, it satisfies all required characteristics
Not yet. In addition, as a yellow dye,
Azo dyes are being considered, but all of the required properties are satisfied.
At present, nothing has been obtained. Ink resistance
Ink using pigments, oil-soluble dyes to improve light properties
Inks using inks are being studied. But the pigment
When used, dispersion stability is poor and storage stability is poor.
Or cause nozzle clogging.
Was. When an oil-soluble dye is used, an organic solvent is
There was a problem in environmental hygiene such as odor due to the use. Special
Characteristics of ink used for inkjet recording system
In the case of, it is greatly affected by the intrinsic properties of the dye.
Therefore, it is extremely important to create dyes that meet these conditions.
You. [0009] SUMMARY OF THE INVENTION An object of the present invention is to provide a hue.
Provides water-based ink that is sharp and has high lightfastness
It is to be. [0010] Means for Solving the Problems The present inventors have set forth the above object.
As a result of intensive studies to solve the problem,
Water-based ink containing the compound
And has high lightfastness, and completed the present invention.
It came to be. That is, the present invention relates to the general formula (1)
Aqueous solution containing a compound represented by the following formula (6) or a salt thereof:
Ink. [0011] Embedded image [In the general formula (1), R₁~ R_FourIs German
First, a hydrogen atom, a halogen atom, a substituted or unsubstituted
Alkyl group, substituted or unsubstituted aryl group, hydroxyl group,-
COOH, -SO_ThreeH, -CONR₇R₈(Where R₇, R
₈Are each independently a hydrogen atom, a substituted or unsubstituted
Alkyl group, substituted or unsubstituted aryl group, or
Represents a substituted or unsubstituted heterocyclic group,₇And R₈Is replaced
Or a ring may be formed by an unsubstituted alkylene group.
Or -SO_TwoR₉R_Ten(Where R₉, R_{1 0}Haso
Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl
Group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group.
Represents an unsubstituted heterocyclic group;₇And R₈Is replaced or nothing
A ring may be formed by a substituted alkylene group)
Represents, R_FiveRepresents a methyl group or -COOH;₆Is
Substituted or unsubstituted alkyl group, or substituted or unsubstituted
Represents a substituted aryl group. Where R₁~ R_FourLess of
One is -COOH. ] [0013] DETAILED DESCRIPTION OF THE INVENTION The aqueous ink of the present invention has a general formula
The compound represented by (1) or a salt thereof is contained. one
In the general formula (1), R₁~ R_FourAre each independently hydrogen
Atom, halogen atom, substituted or unsubstituted alkyl group,
A substituted or unsubstituted aryl group, hydroxyl group, -COOH,
-SO_ThreeH, -CONR₇R₈(Where R₇, R₈Each
Independently a hydrogen atom, a substituted or unsubstituted alkyl group,
A substituted or unsubstituted aryl group, or a substituted or unsubstituted
Represents a substituted heterocyclic group,₇And R₈Is substituted or unsubstituted
May form a ring with the alkylene group of
Is -SO_TwoR₉R_Ten(Where R₉, R_TenAre independent
A hydrogen atom, a substituted or unsubstituted alkyl group,
Or an unsubstituted aryl group, or a substituted or unsubstituted
R represents a heterocyclic group;₇And R₈Is a substituted or unsubstituted al
A ring may be formed by a kylene group);_Five
Represents a methyl group or -COOH;₆Is replaced or
Unsubstituted alkyl group or substituted or unsubstituted ant
Represents a hydroxyl group. Where R₁~ R_FourAt least one of
Is -COOH. Specific examples of the halogen atom include fluorine,
Chlorine, bromine and iodine. Substituted or unsubstituted
Specific examples of the alkyl group include a methyl group, an ethyl group, n
-Propyl group, n-butyl group, n-pentyl group, n-
Xyl group, n-heptyl group, n-octyl group, n-decyl
Group, n-tetradecyl group, n-octadecyl group, n-
The total carbon number of the icosyl group and the like is 20 or less, preferably 15 or less
Linear alkyl group, isopropyl group, isobutyl group, s
ec-butyl group, isopentyl group, sec-pentyl
Group, 1-methylpentyl group, 2-methylpentyl group, 3
-Methylpentyl group, 4-methylpentyl group, 1-ethyl
Rubutyl group, 2-ethylbutyl group, 1-methylhexyl
Group, 2-methylhexyl group, 3-methylhexyl group, 4
-Methylhexyl group, 5-methylhexyl group, 1-ethyl
Rupentyl group, 2-ethylpentyl group, 3-ethyl pen
Tyl group, 1-n-propylbutyl group, 1-iso-pro
Pyrbutyl group 1-iso-propyl-2-methylpro
Pill group, 1-methylheptyl group, 2-methylheptyl
Group, 3-methylheptyl group, 4-methylheptyl group, 5
-Methylheptyl group, 6-methylheptyl group, 1-ethyl
Ruhexyl group, 2-ethylhexyl group, 3-ethylhexyl
Sil group 4-ethylhexyl group, 1-n-propyl pen
Tyl group, 2-n-propylpentyl group, 1-iso-propyl
Ropylpentyl group, 2-iso-propylpentyl group,
1-n-butylbutyl group, 1-iso-butylbutyl
Group, 1-sec-butylbutyl group, 1-tert-butyl
Rubutyl group, 2-tert-butylbutyl group, 2-methyl
Octadecyl group, tert-butyl group, tert-pe
Methyl group, 1,1-dimethylbutyl group, 1,2-dimethyl
Rubutyl group, 1,3-dimethylbutyl group, 2,3-dimethyl
Butyl group, 1-ethyl-2-methylpropyl group,
1,1-dimethylpentyl group, 1,2-dimethylpentyl
Group, 1,3-dimethylpentyl group, 1,4-dimethyl
Pentyl group, 2,2-dimethylpentyl group, 2,3-di
Methylpentyl group, 2,4-dimethylpentyl group, 3,
3-dimethylpentyl group, 3,4-dimethylpentyl
Group, 1-ethyl-1-methylbutyl group, 1-ethyl-2
-Methylbutyl group, 1-ethyl-3-methylbutyl group,
2-ethyl-1-methylbutyl group, 2-ethyl-3-methyl
Butyl group, 1,1-dimethylhexyl group, 1,2-
Dimethylhexyl group, 1,3-dimethylhexyl group,
1,4-dimethylhexyl group, 1,5-dimethylhexyl
Group, 2,2-dimethylhexyl group, 2,3-dimethyl
Hexyl group, 2,4-dimethylhexyl group, 2,5-di
Methylhexyl group, 3,3-dimethylhexyl group, 3,
4-dimethylhexyl group, 3,5-dimethylhexyl
Group, 4,4-dimethylhexyl group, 4,5-dimethylhexyl group
Xyl group, 1-ethyl-2-methylpentyl group, 1-d
Tyl-3-methylpentyl group, 1-ethyl-4-methyl
Pentyl group, 2-ethyl-1-methylpentyl group, 2-
Ethyl-2-methylpentyl group, 2-ethyl-3-methyl
Rupentyl group, 2-ethyl-4-methylpentyl group, 3
-Ethyl-1-methylpentyl group, 3-ethyl-2-me
A tylpentyl group, a 3-ethyl-3-methylpentyl group,
3-ethyl-4-methylpentyl group, 1-n-propyl
-1-methylbutyl group, 1-n-propyl-2-methyl
Butyl group, 1-n-propyl-3-methylbutyl group, 1
-Iso-propyl-1-methylbutyl group, 1-iso
-Propyl-2-methylbutyl group, 1-iso-propyl
Ru-3-methylbutyl group, 1,1-diethylbutyl group,
1,2-diethylbutyl group, 2,3-dimethylhexade
A sil group, a 1,1,2-trimethylpropyl group, 1,2,2
2-trimethylpropyl group, 1,1,2-trimethylbut
Tyl group, 1,1,3-trimethylbutyl group, 1,2,3
-Trimethylbutyl group, 1,2,2-trimethylbutyl
Group, 1,3,3-trimethylbutyl group, 2,3,3-to
Limethylbutyl group, 1,1,2-trimethylpentyl
Group, 1,1,3-trimethylpentyl group, 1,1,4-
Trimethylpentyl group, 1,2,2-trimethylpentyl
1,2,3-trimethylpentyl group, 1,2,4
-Trimethylpentyl group, 1,3,4-trimethylpen
Butyl, 2,2,3-trimethylpentyl, 2,2
4-trimethylpentyl group, 2,3,4-trimethylpe
Methyl group, 1,3,3-trimethylpentyl group, 2,
3,3-trimethylpentyl group, 3,3,4-trimethyl
Rupentyl group, 1,4,4-trimethylpentyl group,
2,4,4-trimethylpentyl group, 3,4,4-tri
Methylpentyl group, 1-ethyl-1,2-dimethylbutyi
Group, 1-ethyl-1,3-dimethylbutyl group, 1-E
Tyl-2,3-dimethylbutyl group, 2-ethyl-1,1
-Dimethylbutyl group, 2-ethyl-1,2-dimethylbutyl
Tyl group, 2-ethyl-1,3-dimethylbutyl group, 2-
Ethyl-2,3-dimethylbutyl group, 2,2,3-tri
Total carbon number 20 or less, such as methyl heptadecyl group, preferably
Represents 15 or less branched alkyl groups, cyclopentyl groups,
Rohexyl group, methylcyclopentyl group, methylcyclo
Hexyl group, 1,2-dimethylcyclohexyl group, 1,
3-dimethylcyclohexyl group, 1,4-dimethylcycl
Total carbon number 2 such as rohexyl group, ethylcyclohexyl group, etc.
0 or less, preferably 15 or less saturated cyclic alkyl groups, Benzyl group, 4-methylbenzyl group,
Nylethyl group, phenylpropyl group, naphthylethyl group
Other specific examples of the substituted or unsubstituted aryl groups described below
Methyl group, ethyl group, having an aryl group in the side chain
Total carbon number 20 or less such as propyl group, preferably 15 or less
Aryl substituted alkyl group, fluoromethyl group, difur
Oromethyl group, trifluoromethyl group, chloromethyl
Group, dichloromethyl group, trichloromethyl group,
Tyl group, dibromomethyl group, tribromomethyl group, full
Oroethyl, chloroethyl, bromoethyl, tri
Fluoroethyl group, pentafluoroethyl group, tetrac
Halo such as loroethyl group and hexafluoroisopropyl group
20 or less total carbon atoms partially or completely substituted by a gen atom,
Preferably no more than 15 halogenated alkyl groups, hydroxy
Cimethyl group, 1-hydroxyethyl group, 2-hydroxy
Ethyl group, 1-hydroxypropyl group, 2-hydroxy
Propyl group, 3-hydroxypropyl group, 1-hydroxy
Cybutyl group, 2-hydroxybutyl group, 3-hydroxy
Butyl group, 4-hydroxybutyl group, 1-hydroxype
Methyl group, 2-hydroxypentyl group, 3-hydroxy
Pentyl group, 4-hydroxypentyl group, 5-hydroxy
Cypentyl group, 1-hydroxyhexyl group, 2-hydro
Xyhexyl group, 3-hydroxyhexyl group, 4-hydrid
Loxyhexyl group, 5-hydroxyhexyl group, 6-h
Droxyhexyl group, dihydroxypropyl group, dihydric
Roxybutyl group, dihydroxypentyl group, dihydroxy
Sihexyl group, trihydroxybutyl group, trihydroxy
Cipentyl group, trihydroxyhexyl group, tetrahydrid
Roxypentyl group, tetrahydroxyhexyl group, pen
Some or all of the hydroxyl groups such as tahydroxyhexyl are hydroxyl groups
Substituted humans having a total carbon number of 20 or less, preferably 15 or less.
Droxyalkyl group, carboxymethyl group, 1-carbo
Xyethyl group, 2-carboxyethyl group, 1-carboxy
Cypropyl group, 2-carboxypropyl group, 3-carbo
Xypropyl group, 1-carboxybutyl group, 2-carbo
Xybutyl group, 3-carboxybutyl group, 4-carboxy
Cybutyl group, 1-carboxypentyl group, 2-carboxy
Cipentyl group, 3-carboxypentyl group, 4-carbo
Xypentyl group, 5-carboxypentyl group, 1-cal
Boxyhexyl group, 2-carboxyhexyl group, 3-ca
Ruboxyhexyl group, 4-carboxyhexyl group, 5-
Carboxyhexyl group, 6-carboxyhexyl group, di
Carboxymethyl group, 1,2-dicarboxyethyl group,
2,2-dicarboxyethyl group, 2,3-dicarboxy
Propyl group, 1,2-dicarboxypropyl group, 3,3
-Dicarboxypropyl group, 1,2-dicarboxybuty
Group, 2,3-dicarboxybutyl group, 3,4-dical
Boxybutyl group, 2,4-dicarboxybutyl group, 1,
2-dicarboxypentyl group, 2,3-dicarboxype
Methyl group, 2,4-dicarboxypentyl group, 2,5-
Dicarboxypentyl group, 4,5-dicarboxypent
1,2-dicarboxyhexyl group, 1,3-dica
Ruboxyhexyl group, 2,3-dicarboxyhexyl
Group, 2,4-dicarboxyhexyl group, 2,5-dical
Boxyhexyl group, 2,6-dicarboxyhexyl group,
3,5-dicarboxyhexyl group, 3,6-dicarboxy
Sihexyl group, 1,2,2-tricarboxybutyl group,
1,2,4-tricarboxybutyl group, 2,3,4-to
Licarboxybutyl group, 3,4,4-tricarboxybu
Tyl group, 1,2,2-tricarboxypentyl group, 1,
2,3-tricarboxypentyl group, 2,3,4-tri
Carboxypentyl group, 3,4,5-tricarboxype
An ethyl group, a 3,5,5-tricarboxypentyl group,
1,2,3-tricarboxyhexyl group, 1,2,4-
Tricarboxyhexyl group, 2,3,4-tricarboxy
Cyhexyl group, 2,3,5-tricarboxyhexyl
Group, 2,3,6-tricarboxyhexyl group, 3,4
5-tricarboxyhexyl group, 3,4,6-trical
Boxyhexyl group, 4,5,6-tricarboxyhexyl
A 1,2,3,3-tetracarboxypentyl group,
2,3,4,5-tetracarboxypentyl group, 2,
4,5,5-tetracarboxypentyl group, 3,4
5,5-tetracarboxypentyl group, 1,2,3
3,5-pentacarboxyhexyl group, 1,2,3
4,5-pentacarboxyhexyl group, 2,3,4
5,5-pentacarboxyhexyl group, 3,4,4,
5,5-pentacarboxyhexyl group, 1,2,4
Part or all of the 5,5-pentacarboxyhexyl group, etc.
The total number of carbon atoms substituted with a carboxyl group is 20 or less,
Preferably no more than 15 carboxyalkyl groups, hydroxy
Carboxymethyl group, 1-hydroxy-2-carboxy
Ethyl group, 2-hydroxy-1-carboxyethyl group,
1-hydroxy-2-carboxypropyl group, 1,2-
Dihydroxy-2-carboxypropyl group, 1,2-di
Hydroxy-3-carboxypropyl group, 4-hydroxy
C-1-carboxybutyl group, 1,2-dihydroxy-
2-carboxybutyl group, 1,2-dihydroxy-3-
Carboxybutyl group, 1,2,3-trihydroxy-4
-Carboxybutyl group, 4-hydroxy-1-carboxy
Cypentyl group, 5-hydroxy-2-carboxy pent
Group, 1,2-dihydroxy-3-carboxypentyl
Group, 1,2-dihydroxy-4-carboxypentyl
Group, 1,2,2-trihydroxy-5-carboxypen
A tyl group, a 5-hydroxy-1-carboxyhexyl group,
1,2-dihydroxy-2-carboxyhexyl group,
1,2-dihydroxy-3-carboxyhexyl group,
1,2,2-trihydroxy-4-carboxyhexyl
Group, 1,2,2-trihydroxy-5-carboxyhex
Sil group, 2,3-dihydroxy-6-carboxyhexyl
Group, 1-hydroxy-2,3-dicarboxypropyl
A 2-hydroxy-3,4-dicarboxybutyl group,
2,3-dihydroxy-3,5-dicarboxypentyl
Group, 1,2,3-trihydroxy-5,6-dicarboxy
Sihexyl group, 2-hydroxy-3,4,4-trical
Boxybutyl group, 2,3-hydroxy-2,3,5-to
Licarboxypentyl group, 5-hydroxy-2,3,6
-Tricarboxyhexyl group, 5-hydroxy-2,
3,4,4-tetracarboxypentyl group, 2-hydro
A xy-2,4,6,6-tetracarboxyhexyl group,
2,3-dihydroxy-2,3,4,5,6-pentaka
Some or all of the hydroxyl groups such as ruboxyhexyl are hydroxyl
20 or less total carbon atoms substituted with a group and a carboxyl group, preferably
Preferably no more than 15 hydroxycarboxyalkyl groups, Sulfomethyl group, 1-sulfoethyl group, 2
-Sulfoethyl group, 1-sulfopropyl group, 2-sulfo
Propyl group, 3-sulfopropyl group, 1-sulfobutyl
Group, 2-sulfobutyl group, 3-sulfobutyl group, 4-s
Rufobutyl group, 1-sulfopentyl group, 2-sulfopenpene
Tyl group, 3-sulfopentyl group, 4-sulfopentyl
Group, 5-sulfopentyl group, 1-sulfohexyl group, 2
-Sulfohexyl group, 3-sulfohexyl group, 4-sulfo
Hohexyl group, 5-sulfohexyl group, 6-sulfohex
Sil group, disulfopropyl group, disulfobutyl group, dis
Ruhopentyl group, disulfohexyl group, trisulfobuti
Group, trisulfopentyl group, trisulfohexyl group,
Tetrasulfopentyl group, tetrasulfohexyl group,
Some or all of the sulfahexyl group, etc. are sulfo groups
The total number of substituted carbon atoms is 20 or less, preferably 15 or less.
Ruhoalkyl group, hydroxysulfomethyl group, 2-hydrido
Roxy-1-sulfoethyl group, 1-hydroxy-2-s
Rufoethyl group, 2,3-dihydroxy-1-sulfopro
Pill group, 2,3-dihydroxy-2-sulfopropyl
Group, 2-hydroxy-3-sulfopropyl group, 4-hydrido
Roxy-1-sulfobutyl group, 3,4-dihydroxy-
2-sulfobutyl group, 2,3,4-trihydroxy-3
-Sulfobutyl group, 2,3,4-trihydroxy-4-
Sulfobutyl group, 5-hydroxy-1-sulfopentyl
A 2,5-dihydroxy-2-sulfopentyl group,
2,5-dihydroxy-3-sulfopentyl group, 1,
2,5-trihydroxy-4-sulfopentyl group, 1,
2,3,4-tetrahydroxy-5-sulfopentyl
Group, 6-hydroxy-1-sulfohexyl group, 5-hydr
Roxy-2-sulfohexyl group, 6-hydroxy-3-
Sulfohexyl group, 5,6-dihydroxy-4-sulfo
Hexyl group, 1,3,6-trihydroxy-5-sulfo
Hexyl group, 2,3,4,5-tetrahydroxy-6-
Sulfohexyl group, 1-hydroxy-2,3-disulfo
Propyl group, 2-hydroxy-3,4-disulfobutyl
Group, 2,3-dihydroxy-4,5-disulfopentyl
Group, 2,3,3-trihydroxy-4,5-disulfohe
Xyl group, 2-hydroxy-2,3,4-trisulfob
Tyl group, 2-hydroxy-3,4,5-trisulfopene
Tyl group, 2,4-dihydroxy-3,5,6-trisul
Hohexyl group, 1,3-dihydroxy-2,4,5,5
-Tetrasulfopentyl group, 1,3,6-trihydroxy
C-2,4,5,6-tetrasulfohexyl group, 3,5
-Dihydroxy-1,2,3,4,6-pentasulfohe
Total substituted with hydroxyl groups such as xyl groups and sulfo groups
Hydroxysulfone having 20 or less, preferably 15 or less carbon atoms
A hoalkyl group, Carboxysulfomethyl group, carboxys
Rufoethyl group, carboxysulfopropyl group, carboxy
Disulfobutyl group, carboxysulfopentyl group, cal
Boxysulfohexyl group, dicarboxysulfoethyl
Group, dicarboxy sulfopropyl group, dicarboxy sulf
Hobutyl, dicarboxysulfohexyl, carboxyl
Sidisulfoethyl group, carboxydisulfopropyl group,
Ruboxisulfobutyl group, carboxydisulfohexyl
And carboxyl groups such as dicarboxydisulfo group
A total of 20 or less, preferably 15 carbon atoms,
The following carboxysulfoalkyl groups, hydroxycarbo
Xisulfoethyl group, hydroxycarboxysulfopro
Pill group, hydroxycarboxysulfobutyl group, hydro
Xycarboxysulfopentyl group, hydroxycarboxy
Disulfohexyl group, dihydroxycarboxysulfop
Ropyl group, dihydroxycarboxysulfobutyl group, di
Hydroxycarboxysulfopentyl group, dihydroxy
Carboxysulfohexyl group, hydroxydicarboxy
Sulfoethyl group, hydroxydicarboxysulfoprop
Group, hydroxydicarboxysulfobutyl group, hydro
Xydicarboxysulfohexyl group, hydroxycarbo
Xydisulfoethyl group, hydroxycarboxydisulfop
Propyl group, hydroxycarboxydisulfobutyl group,
Droxycarboxydisulfohexyl group, hydroxydi
Carboxyl group such as carboxydisulfo group and sulfo group
Substituted humans having a total carbon number of 20 or less, preferably 15 or less.
Substituted alkyl such as droxycarboxysulfoalkyl group
Groups. Specific examples of substituted or unsubstituted aryl groups
Such as phenyl, naphthyl, and anthranyl groups
Aromatic hydrocarbon having a total carbon number of 20 or less, preferably 15 or less
Element, 2-methylphenyl group, 3-methylphenyl group, 4
-Methylphenyl group, 2-ethylphenyl group, propyl
Phenyl group, butylphenyl group, hexylphenyl group,
Cyclohexylphenyl group, octylphenyl group, 2-
Methyl-1-naphthyl group, 3-methyl-1-naphthyl
Group, 4-methyl-1-naphthyl group, 5-methyl-1-na
Phthyl group, 6-methyl-1-naphthyl group, 7-methyl-
1-naphthyl group, 8-methyl-1-naphthyl group, 1-methyl
A tyl-2-naphthyl group, a 3-methyl-2-naphthyl group,
4-methyl-2-naphthyl group, 5-methyl-2-naphthyl
Group, 6-methyl-2-naphthyl group, 7-methyl-2-
Naphthyl group, 8-methyl-2-naphthyl group, 2-ethyl
-1-naphthyl group, 2,3-dimethylphenyl group, 2,
4-dimethylphenyl group, 2,5-dimethylphenyl
Group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group
Phenyl, 3,5-dimethylphenyl, 3,6-dimethyl
Tylphenyl group, 2,3,4-trimethylphenyl group,
2,3,5-trimethylphenyl group, 2,3,6-tri
Methylphenyl group, 2,4,5-trimethylphenyl
Group, 2,4,6-trimethylphenyl group, 3,4,5-
Total carbon number 20 or less such as trimethylphenyl group, preferably
Is an alkyl-substituted aryl group of 15 or less, a biphenyl group,
Substitution or no substitution of styrylphenyl group, stilbenyl group, etc.
A total of 20 or less carbon atoms substituted with a substituted aryl group, preferably
Or an aryl group of 15 or less, 2-hydroxyphenyl
Group, 3-hydroxyphenyl group, 4-hydroxyphenyl
Group, 2-hydroxy-1-naphthyl group, 3-hydroxy
C-1-naphthyl group, 4-hydroxy-1-naphthyl
Group, 5-hydroxy-1-naphthyl group, 6-hydroxy
-1-naphthyl group, 7-hydroxy-1-naphthyl group,
8-hydroxy-1-naphthyl group, 1-hydroxy-2
-Naphthyl group, 3-hydroxy-2-naphthyl group, 4-
Hydroxy-2-naphthyl group, 5-hydroxy-2-na
Phthyl group, 6-hydroxy-2-naphthyl group, 7-hydr
Roxy-2-naphthyl group, 8-hydroxy-2-naphthyl
, A 2,3-dihydroxyphenyl group, a 2,4-dihi group
Droxyphenyl group, 2,5-dihydroxyphenyl
Group, 2,6-dihydroxyphenyl group, 3,4-dihydrido
Roxyphenyl group, 3,5-dihydroxyphenyl group,
3,6-dihydroxyphenyl group, 2,3-dihydroxy
C-1-naphthyl group, 2,4-dihydroxy-1-naph
A tyl group, a 2,6-dihydroxy-1-naphthyl group,
7-dihydroxy-1-naphthyl group, 2,8-dihydro
Xy-1-naphthyl group, 3,4-dihydroxy-1-na
A futyl group, a 3,5-dihydroxy-1-naphthyl group,
3,6-dihydroxy-1-naphthyl group, 3,6-dihi
Droxy-1-naphthyl group, 3,7-dihydroxy-1
-Naphthyl group, 3,8-dihydroxy-1-naphthyl
Group, 4,5-dihydroxy-1-naphthyl group, 4,6-
Dihydroxy-1-naphthyl group, 4,7-dihydroxy
-1-naphthyl group, 4,8-dihydroxy-1-naphthyl
Group, 5,6-dihydroxy-1-naphthyl group, 5,7
-Dihydroxy-1-naphthyl group, 5,8-dihydroxy
C-1-naphthyl group, 6,7-dihydroxy-1-naph
Tyl group, 6,8-dihydroxy-1-naphthyl group, 7,
8-dihydroxy-1-naphthyl group, 1,3-dihydro
Xy-2-naphthyl group, 1,4-dihydroxy-2-na
A futyl group, a 1,6-dihydroxy-2-naphthyl group,
1,7-dihydroxy-2-naphthyl group, 1,8-dihi
Droxy-2-naphthyl group, 3,4-dihydroxy-2
-Naphthyl group, 3,5-dihydroxy-2-naphthyl
Group, 3,6-dihydroxy-2-naphthyl group, 3,6-
Dihydroxy-2-naphthyl group, 3,7-dihydroxy
-2-naphthyl group, 3,8-dihydroxy-2-naphthyl
Group, 4,5-dihydroxy-2-naphthyl group, 4,6
-Dihydroxy-2-naphthyl group, 4,7-dihydroxy
C-2-naphthyl group, 4,8-dihydroxy-2-naph
A tyl group, a 5,6-dihydroxy-2-naphthyl group,
7-dihydroxy-2-naphthyl group, 5,8-dihydro
Xy-2-naphthyl group, 6,7-dihydroxy-2-na
A phthyl group, a 6,8-dihydroxy-2-naphthyl group,
Total carbon number 2 such as 7,8-dihydroxy-2-naphthyl group
0 or less, preferably 15 or less hydroxyaryl groups, 2-carboxyphenyl group, 3-carboxy
Cyphenyl group, 4-carboxyphenyl group, 2,3-di
Carboxyphenyl group, 2,4-dicarboxyphenyl
Group, 2,5-dicarboxyphenyl group, 2,6-dical
Boxyphenyl group, 3,4-dicarboxyphenyl group,
3,5-dicarboxyphenyl group, 3,6-dicarboxy
Cyphenyl group, 2,3,4-tricarboxyphenyl
Group, 2,3,5-tricarboxyphenyl group, 2,3
6-tricarboxyphenyl group, 2,4,5-trical
Boxyphenyl group, 2,4,6-tricarboxyphenyl
Group, 3,4,5-tricarboxyphenyl group, 4-ca
Ruboxyl-1-naphthyl group, 5-carboxy-1-naph
Tyl group, 6-carboxy-1-naphthyl group, 7-carbo
Xy-1-naphthyl group, 8-carboxy-1-naphthyl
Group, 1-carboxy-2-naphthyl group, 3-carboxy
-2-naphthyl group, 4-carboxy-2-naphthyl group,
5-carboxy-2-naphthyl group, 6-carboxy-2
-Naphthyl group, 7-carboxy-2-naphthyl group, 8-
Total carbon number of 20 or less such as carboxy-2-naphthyl group is preferable.
Preferably no more than 15 carboxyaryl groups, 2-hydro
Xy-3-carboxyphenyl group, 2-hydroxy-4
-Carboxyphenyl group, 2-hydroxy-5-carbo
Xyphenyl group, 2-hydroxy-6-carboxyphen
A nyl group, a 3-hydroxy-2-carboxyphenyl group,
3-hydroxy-4-carboxyphenyl group, 3-hydr
Roxy-5-carboxyphenyl group, 3-hydroxy-
6-carboxyphenyl group, 4-hydroxy-2-cal
Boxyphenyl group, 4-hydroxy-3-carboxyphen
Monohydroxymonocarbox having 10 or less carbon atoms such as phenyl group
Boxyaryl group, 2,3-dihydroxy-4-carbo
Xyphenyl group, 2,3-dihydroxy-5-carboxy
Cyphenyl group, 2,3-dihydroxy-6-carboxy
Phenyl group, 2,4-dihydroxy-3-carboxyphen
Enyl group, 2,4-dihydroxy-5-carboxyphenyl
Nyl group, 2,4-dihydroxy-6-carboxyphenyl
Group, 2,5-dihydroxy-3-carboxyphenyl
Group, 2,5-dihydroxy-4-carboxyphenyl
Group, 2,5-dihydroxy-6-carboxyphenyl
Group, 2,6-dihydroxy-3-carboxyphenyl
Group, 2,6-dihydroxy-4-carboxyphenyl
Group, 3,4-dihydroxy-2-carboxyphenyl
Group, 3,4-dihydroxy-5-carboxyphenyl
Group, 3,4-dihydroxy-6-carboxyphenyl
Group, 3,5-dihydroxy-2-carboxyphenyl
Group, 3,5-dihydroxy-4-carboxyphenyl
Group, 3,6-dihydroxy-2-carboxyphenyl
Group, 3,6-dihydroxy-4-carboxyphenyl
Group, 3,6-dihydroxy-5-carboxyphenyl group
Dihydro having a total carbon number of 20 or less, preferably 15 or less
Xymonocarboxyaryl group, 2,3-dicarboxy
-4-hydroxyphenyl group, 2,3-dicarboxy-
5-hydroxyphenyl group, 2,3-dicarboxy-6
-Hydroxyphenyl group, 2,4-dicarboxy-3-
Hydroxyphenyl group, 2,4-dicarboxy-5-h
Droxyphenyl group, 2,4-dicarboxy-6-hydrido
Roxyphenyl group, 2,5-dicarboxy-3-hydro
Xyphenyl group, 2,5-dicarboxy-4-hydroxy
Cyphenyl group, 2,5-dicarboxy-6-hydroxy
Phenyl group, 2,6-dicarboxy-3-hydroxy
Enyl group, 2,6-dicarboxy-4-hydroxyphene
Nyl group, 3,4-dicarboxy-2-hydroxyphenyl
Group, 3,4-dicarboxy-5-hydroxyphenyl
Group, 3,4-dicarboxy-6-hydroxyphenyl
Group, 3,5-dicarboxy-2-hydroxyphenyl
Group, 3,5-dicarboxy-4-hydroxyphenyl
Group, 3,6-dicarboxy-2-hydroxyphenyl
Group, 3,6-dicarboxy-4-hydroxyphenyl
Group, 3,6-dicarboxy-5-hydroxyphenyl group
Monohydric having 20 or less, preferably 15 or less total carbon atoms
Roxydicarboxyaryl group, 2-sulfophenyl
Group, 3-sulfophenyl group, 4-sulfophenyl group, 2
-Sulfo-1-naphthyl group, 3-sulfo-1-naphthyl
Group, 4-sulfo-1-naphthyl group, 5-sulfo-1-na
Phthyl group, 6-sulfo-1-naphthyl group, 7-sulfo-
1-naphthyl group, 8-sulfo-1-naphthyl group, 1-s
A ruho-2-naphthyl group, a 3-sulfo-2-naphthyl group,
4-sulfo-2-naphthyl group, 5-sulfo-2-naphthyl
Group, 6-sulfo-2-naphthyl group, 7-sulfo-2-
Naphthyl group, 8-sulfo-2-naphthyl group, 2,3-di
Sulfophenyl group, 2,4-disulfophenyl group, 2,
5-disulfophenyl group, 2,6-disulfophenyl
Group, 3,4-disulfophenyl group, 3,5-disulfofoff group
Phenyl, 3,6-disulfophenyl, 2,3-dis
Rufo-1-naphthyl group, 2,4-disulfo-1-naphthy
, A 2,6-disulfo-1-naphthyl group, a 2,7-di
Sulfo-1-naphthyl group, 2,8-disulfo-1-naph
Tyl group, 3,4-disulfo-1-naphthyl group, 3,5-
Disulfo-1-naphthyl group, 3,6-disulfo-1-na
Phthyl group, 3,6-disulfo-1-naphthyl group, 3,7
-Disulfo-1-naphthyl group, 3,8-disulfo-1-
Naphthyl group, 4,5-disulfo-1-naphthyl group, 4,
6-disulfo-1-naphthyl group, 4,7-disulfo-1
-Naphthyl group, 4,8-disulfo-1-naphthyl group,
5,6-disulfo-1-naphthyl group, 5,7-disulfo
-1-naphthyl group, 5,8-disulfo-1-naphthyl
Group, 6,7-disulfo-1-naphthyl group, 6,8-dis
Rufo-1-naphthyl group, 7,8-disulfo-1-naphthy
Group, 1,3-disulfo-2-naphthyl group, 1,4-di
Sulfo-2-naphthyl group, 1,6-disulfo-2-naph
Tyl group, 1,7-disulfo-2-naphthyl group, 1,8-
Disulfo-2-naphthyl group, 3,4-disulfo-2-na
Phthyl group, 3,5-disulfo-2-naphthyl group, 3,6
-Disulfo-2-naphthyl group, 3,6-disulfo-2-
Naphthyl group, 3,7-disulfo-2-naphthyl group, 3,
8-disulfo-2-naphthyl group, 4,5-disulfo-2
-Naphthyl group, 4,6-disulfo-2-naphthyl group,
4,7-disulfo-2-naphthyl group, 4,8-disulfo
-2-naphthyl group, 5,6-disulfo-2-naphthyl
Group, 5,7-disulfo-2-naphthyl group, 5,8-dis
Ruho-2-naphthyl group, 6,7-disulfo-2-naphthy
Group, 6,8-disulfo-2-naphthyl group, 7,8-di
Sulfo-2-naphthyl group, 2,3,4-trisulfofe
Nyl group, 2,3,5-trisulfophenyl group, 2,3
6-trisulfophenyl group, 2,4,5-trisulfoff
Phenyl, 2,4,6-trisulfophenyl, 3,
4,5-trisulfophenyl group, trisulfo-1-naph
Total carbon number 20 such as tyl group and trisulfo-2-naphthyl group
Or less, preferably 15 or less sulfoaryl groups, A 2-hydroxy-3-sulfophenyl group,
2-hydroxy-4-sulfophenyl group, 2-hydroxy
Ci-5-sulfophenyl group, 2-hydroxy-6-sul
Hophenyl group, 3-hydroxy-2-sulfophenyl
Group, 3-hydroxy-4-sulfophenyl group, 3-hydr
Roxy-5-sulfophenyl group, 3-hydroxy-6
Sulfophenyl group, 4-hydroxy-2-sulfophenyl
Group, 4-hydroxy-3-sulfophenyl group, hydro
Xy-2-sulfo-1-naphthyl group, hydroxy-3-
Sulfo-1-naphthyl group, hydroxy-4-sulfo-1
-Naphthyl group, hydroxy-5-sulfo-1-naphthyl
Group, hydroxy-6-sulfo-1-naphthyl group, hydro
Xy-7-sulfo-1-naphthyl group, hydroxy-8-
Sulfo-1-naphthyl group, hydroxy-1-sulfo-2
-Naphthyl group, hydroxy-3-sulfo-2-naphthyl
Group, hydroxy-4-sulfo-2-naphthyl group, hydro
Xy-5-sulfo-2-naphthyl group, hydroxy-6
Sulfo-2-naphthyl group, hydroxy-7-sulfo-2
-Naphthyl group, hydroxy-8-sulfo-2-naphthyl
Monohydric group having a total carbon number of 20 or less, preferably 15 or less
Droxymonosulfoaryl group, 2,3-dihydroxy
-4-sulfophenyl group, 2,3-dihydroxy-5-
Sulfophenyl group, 2,3-dihydroxy-6-sulfo
Phenyl group, 2,4-dihydroxy-3-sulfophenyl
A 2,4-dihydroxy-5-sulfophenyl group,
2,4-dihydroxy-6-sulfophenyl group, 2,5
-Dihydroxy-3-sulfophenyl group, 2,5-dihi
Droxy-4-sulfophenyl group, 2,5-dihydroxy
C-6-sulfophenyl group, 2,6-dihydroxy-3
-Sulfophenyl group, 2,6-dihydroxy-4-sul
Hophenyl group, 3,4-dihydroxy-2-sulfofe
Nyl group, 3,4-dihydroxy-5-sulfophenyl
Group, 3,4-dihydroxy-6-sulfophenyl group,
3,5-dihydroxy-2-sulfophenyl group, 3,5
-Dihydroxy-4-sulfophenyl group, 3,6-dihi
Droxy-2-sulfophenyl group, 3,6-dihydroxy
C-4-sulfophenyl group, 3,6-dihydroxy-5
-Sulfophenyl group, dihydroxy-2-sulfo-1-
Naphthyl group, dihydroxy-3-sulfo-1-naphthyl
Group, dihydroxy-4-sulfo-1-naphthyl group, dihi
Droxy-5-sulfo-1-naphthyl group, dihydroxy
-6-sulfo-1-naphthyl group, dihydroxy-7-s
Rufo-1-naphthyl group, dihydroxy-8-sulfo-1
-Naphthyl group, dihydroxy-1-sulfo-2-naphthy
Group, dihydroxy-3-sulfo-2-naphthyl group, di
Hydroxy-4-sulfo-2-naphthyl group, dihydroxy
C-5-sulfo-2-naphthyl group, dihydroxy-6-
Sulfo-2-naphthyl group, dihydroxy-7-sulfo-
2-naphthyl group, dihydroxy-8-sulfo-2-naph
Dicarbons having a total carbon number of 20 or less, preferably 15 or less, such as a tyl group
Hydroxymonosulfoaryl group, hydroxy-3,6
-Disulfo-1-naphthyl group, hydroxy-3,7-di
Sulfo-1-naphthyl group, hydroxy-4,5-disul
E-1-naphthyl group, hydroxy-4,7-disulfo-
1-naphthyl group, hydroxy-4,8-disulfo-1-
Naphthyl group, hydroxy-5,8-disulfo-1-naph
Tyl group, hydroxy-6,7-disulfo-1-naphthyl
A hydroxy-3,6-disulfo-2-naphthyl group;
Hydroxy-3,7-disulfo-2-naphthyl group, hydrido
Roxy-4,5-disulfo-2-naphthyl group, hydroxy
C-4,7-disulfo-2-naphthyl group, hydroxy-
4,8-disulfo-2-naphthyl group, hydroxy-5
8-disulfo-2-naphthyl group, hydroxy-6,7-
Total carbon number of 20 or less such as disulfo-2-naphthyl group is preferred.
Or 15 or less monohydroxydisulfoaryl groups, Carboxysulfophenyl group, carboxy
Disulfophenyl group, dicarboxysulfophenyl group,
Dicarboxydisulfophenyl group, carboxysulfona
Phthyl group, carboxydisulfonaphthyl group, dicarboxy
Disulfonaphthyl group, dicarboxydisulfonaphthyl group
Having a total carbon number of 20 or less, preferably 15 or less
Disulfoaryl group, hydroxycarboxysulfofe
Group, hydroxycarboxydisulfophenyl group,
Droxydicarboxysulfophenyl group, hydroxydi
Carboxydisulfophenyl group, dihydroxycarboxy
Disulfophenyl group, hydroxycarboxysulfonaf
Tyl group, hydroxycarboxydisulfonaphthyl group,
Droxydicarboxysulfonaphthyl group, hydroxydi
Carboxydisulfonaphthyl group, dihydroxycarboxy
20 or less total carbon atoms such as a sulfonaphthyl group, preferably
15 or less hydroxycarboxysulfoaryl groups, 2
-Methoxyphenyl group, 3-methoxyphenyl group, 4-
Methoxyphenyl group, 2-ethoxyphenyl group, propo
Xyphenyl group, butoxyphenyl group, hexyloxy
Phenyl group, cyclohexyloxyphenyl group, octy
Luoxyphenyl group, 2-methoxy-1-naphthyl group,
3-methoxy-1-naphthyl group, 4-methoxy-1-na
Phthyl group, 5-methoxy-1-naphthyl group, 6-methoxy
C-1-naphthyl group, 7-methoxy-1-naphthyl group,
8-methoxy-1-naphthyl group, 1-methoxy-2-na
Phthyl group, 3-methoxy-2-naphthyl group, 4-methoxy
C-2-naphthyl group, 5-methoxy-2-naphthyl group,
6-methoxy-2-naphthyl group, 7-methoxy-2-na
Phthyl group, 8-methoxy-2-naphthyl group, 2-ethoxy
Substituted or unsubstituted C 10 or less carbon atoms such as 1-naphthyl group;
The total number of carbon atoms substituted by the substituted alkoxy group is 20 or less, preferably
Or 15 or less monoalkoxyaryl groups, 2,3-
Dimethoxyphenyl group, 2,4-dimethoxyphenyl
Group, 2,5-dimethoxyphenyl group, 2,6-dimethoxy
Cyphenyl group, 3,4-dimethoxyphenyl group, 3,5
-Dimethoxyphenyl group, 3,6-dimethoxyphenyl
Group, 4,5-dimethoxy-1-naphthyl group, 4,7-di
Methoxy-1-naphthyl group, 4,8-dimethoxy-1-
Naphthyl group, 5,8-dimethoxy-1-naphthyl group,
C10 or more carbon atoms such as 5,8-dimethoxy-2-naphthyl group
Total carbons substituted by the substituted or unsubstituted alkoxy groups below
Dialkoxy aryl of number 20 or less, preferably 15 or less
Group, 2,3,4-trimethoxyphenyl group, 2,3
5-trimethoxyphenyl group, 2,3,6-trimethoxy
Cyphenyl group, 2,4,5-trimethoxyphenyl group,
2,4,6-trimethoxyphenyl group, 3,4,5-to
Substitution having 10 or less carbon atoms such as a limethoxyphenyl group or
20 or less total carbon atoms substituted with an unsubstituted alkoxy group, preferably
Preferably no more than 15 trialkoxyaryl groups, chloro
Phenyl group, dichlorophenyl group, trichlorophenyl
Group, bromophenyl group, dibromophenyl group, iodofu
Phenyl, fluorophenyl, chloronaphthyl, butyl
Lomonaphthyl group, difluorophenyl group, trifluoro
Phenyl group, tetrafluorophenyl group, pentafluoro
20 total carbon atoms substituted by halogen atoms such as a rophenyl group
Or less, preferably 15 or less, halogenated aryl groups,
Trifluoromethylphenyl group, trichloromethylphenyl
A part or all of which has 10 or less carbon atoms such as
The total number of carbon atoms substituted by the substituted alkyl group is 20 or less, preferably
Or 15 or less halogenated alkylaryl groups, 2-aminophenyl group, 3-aminophenyl
Group, 4-aminophenyl group, 2-amino-1-naphthy
Group, 3-amino-1-naphthyl group, 4-amino-1-
Naphthyl group, 5-amino-1-naphthyl group, 6-amino
-1-naphthyl group, 7-amino-1-naphthyl group, 8-
Amino-1-naphthyl group, 1-amino-2-naphthyl
Group, 3-amino-2-naphthyl group, 4-amino-2-na
Phthyl group, 5-amino-2-naphthyl group, 6-amino-
2-naphthyl group, 7-amino-2-naphthyl group, 8-a
Total carbon number of 20 or less such as mino-2-naphthyl group, preferably
Is 15 or less monoaminoaryl groups, 2,3-diamino
Phenyl group, 2,4-diaminophenyl group, 2,5-di
Aminophenyl group, 2,6-diaminophenyl group, 3,
4-diaminophenyl group, 3,5-diaminophenyl
Group, 3,6-diaminophenyl group, diamino-1-naph
Total carbon number 20 or more such as tyl group, diamino-2-naphthyl group
And preferably 15 or less diaminoaryl groups,
Tylaminophenyl group, N-ethylaminophenyl group,
N-phenylaminophenyl group, N-tolylaminophen
Total coal such as Nyl group, N-cyclohexylaminophenyl group
N-monosubstituted amino having a prime number of 20 or less, preferably 15 or less
Substituted aryl group, N, N-dimethylaminophenyl group,
N, N-diethylaminophenyl group, N-phenyl-N
-Methylaminophenyl group, N-tolyl-N-ethyla
Minophenyl group, N-chlorophenyl-N-cyclohexyl
Silaminophenyl group, N, N-ditolylaminophenyl
N, having a total carbon number of 20 or less, preferably 15 or less, such as
N-disubstituted amino-substituted aryl group, 3-amino-2-s
Ruhophenyl group, 4-amino-2-sulfophenyl group,
5-amino-2-sulfophenyl group, 6-amino-2-
Sulfophenyl group, 2-amino-3-sulfophenyl
Group, 4-amino-3-sulfophenyl group, 5-amino-
3-sulfophenyl group, 6-amino-3-sulfophenyl
Group, 2-amino-4-sulfophenyl group, 3-amino
-20 or less total carbon number such as 4-sulfophenyl group is preferable
15 or less aminosulfoaryl groups, 3-amino-
2-carboxyphenyl group, 4-amino-2-carboxy
Cyphenyl group, 5-amino-2-carboxyphenyl
Group, 6-amino-2-carboxyphenyl group, 2-amido
No-3-carboxyphenyl group, 4-amino-3-cal
Boxyphenyl group, 5-amino-3-carboxyphenyl
Group, 6-amino-3-carboxyphenyl group, 2-A
Mino-4-carboxyphenyl group, 3-amino-4-ca
Total carbon number of 20 or less such as ruboxyphenyl group, preferably
15 or less aminocarboxyaryl groups;
Methylthiophenyl, ethylthiophenyl, methyl
Alkyls such as ruthionaphthyl and phenylthiophenyl
And a luthioaryl group and an arylthioaryl group.
It is. Specific examples of substituted or unsubstituted alkylene groups
Are ethylene, trimethylene, tetramethyl
Group, pentamethylene group, hexamethylene group, heptame
Tylene group, octamethylene group, methylethylene group, ethyl
20 or less, preferably 15 or less
The following linear or branched alkylene groups are exemplified.
You. Specific examples of the substituted or unsubstituted heterocyclic group include
Tetrahydrofuryl group, tetrahydropyranyl group, pyro
Lysinyl group, pyrrolinyl group, imidazolidinyl group, imi
Dazolinyl group, pyrazolidinyl group, pyrazolinyl group,
Total coal such as peridyl group, piperazinyl group, morpholinyl group
Heterocyclic aliphatic carbon having a prime number of 20 or less, preferably 15 or less
Hydrogen, thienyl, furyl, pyranyl, isoben
Zofuranyl group, chromenyl group, pyrrolyl group, imidazoly
, Pyrazolyl, isothiazolyl, isoxazolyl
Group, pyridyl group, pyrazinyl group, pyrimidyl group, pyr
Dazinyl, triazinyl, indolizinyl, iso
Indolyl, indolyl, indazolyl, quinolyl
, A total carbon number of 20 or less such as an isoquinolyl group, preferably
Is a heterocyclic aromatic hydrocarbon of 15 or less, methylthienyl
Group, methylfuryl group, methylpyranyl group, methylimida
Zolyl group, phenylpyrazolyl group, etc.
20 total carbon atoms substituted with an alkyl or aryl group
Or less, preferably 15 or less heterocyclic aliphatic or aromatic
Group hydrocarbon, hydroxypyridyl group, hydroxypyrazo
Ryl group, hydroxyimidazolyl group, dihydroxytri
Total number of carbon atoms 20 or more substituted with hydroxy group such as azyl group
Below, preferably up to 15 heterocyclic aliphatic or aromatic
Hydrocarbons, cyanopyridyl groups, dicyanoimidazolyl, etc.
A total of 20 or less carbon atoms substituted with a cyano group, preferably
15 or less heterocyclic aliphatic or aromatic hydrocarbon, dic
Halogen atoms such as lolotriazyl and chloropyridyl groups
20 or less, preferably 15 or less
Heterocyclic aliphatic or aromatic hydrocarbon, carboxypyri
Substitute with a carboxy group such as a jyl group or carboxypyrazolyl group
The total number of carbon atoms replaced is 20 or less, preferably 15 or less.
And rocyclic aliphatic or aromatic hydrocarbons. The hydroxyl group in the general formula (1), -COO
H or -SO_ThreeAs a specific example of forming a salt with H,
Alkali metals such as lithium, sodium, potassium, etc.
Alkaline earths such as lilium, magnesium and calcium
Metal, NH_Four, NH_ThreeEt, NH _ThreePr, NH_ThreeBu, NH
_ThreeC₈H₁₇, NH_TwoEt_Two, NH_TwoPr_Two, NH_TwoBu_Two, NH
_Two(CH_TwoCH: CH_Two)_Two, NHEt_Three, NHBu_Three, NH
(C_TwoH_FourOH)_Three, NH (CH_TwoCH: CH_Two)_Three, NMe
_ThreeCH_TwoC₆H_Five, NMe_Four, NBu_FourSuch as ammonium
No. The compounds contained in the aqueous ink of the present invention
Table 1 shows specific examples. The water-based ink of the present invention contains
The compounds or salts thereof are listed in Table 1 (Tables 1 to 3).
It is not limited to a compound or a salt thereof. [0026] [Table 1][0027] [Table 2][0028] [Table 3]The general formula contained in the aqueous ink of the present invention
Preferred among the compounds represented by (1)
Is R of the general formula (1)₆Is a substituted or unsubstituted aryl
And more preferably R.₆Is -C
OOH or -SO_ThreeAn aryl group substituted with H
Things. Hydroxyl group in the general formula (1), -C
OOH or -SO_ThreeGood for forming salt with H
Preferred examples are sodium, potassium, N
H_Four, NH (C_TwoH _FourOH)_Three, NMe_ThreeCH_TwoC₆H_Five, NM
e_Four, NBu_FourIs mentioned. Also, represented by the general formula (1)
The compound represented by the general formula (2)
It is also possible to adopt a structure such as 7). [0030] Embedded image [Wherein R₁~ R₆Is of general formula (1)
Is the same as ] It is represented by the general formula (1) contained in the aqueous ink of the present invention.
Compound according to a conventional azo coupling, for example,
Anilines represented by the general formulas (3) and (8) and a general formula
(4) Coupling with pyrazolones represented by (Formula 9)
Manufactured by [0032] Embedded image [0033] Embedded image [Wherein, R₁~ R₆Is of general formula (1)
Is the same as ] The compound represented by the general formula (1) is specifically, for example,
For example, in hydrochloric acid, an aniline represented by the general formula (3)
After diazotization by adding aqueous sodium nitrite solution,
This diazotized compound is added to pyrazolones represented by the formula (4).
After performing the azo coupling reaction, the reaction solution
In a poor solvent, and the resulting crystals are filtered off.
It is. A method for producing the compound represented by the general formula (1)
Is not limited to this method. The aqueous solution of the present invention
Inks are aqueous marker inks, aqueous printing inks, inks
Inkjet for recording liquid of inkjet recording system, inkjet
Can be used as various aqueous inks such as dye liquids for printing.
it can. Aqueous especially for ink jet recording liquid
Useful as ink. The general formula contained in the aqueous ink of the present invention
The compound represented by (1) can be used as it is.
In addition, it is especially used for the recording liquid of the ink jet recording method.
If the recording device discharges due to inorganic salts, etc., contained in the dye,
To prevent clogging of the exit nozzle, for example, ion
Desalination by exchange resin or ultrafiltration, or other desalination
It can also be used after purification by a physical method or the like. The aqueous ink of the present invention is represented by the following general formula (1).
Compounds, water, and, if necessary, organic solvents and
It contains a seed additive. As an aqueous ink,
0.5 to 20% by weight of a compound represented by the general formula (1), water
10 to 99.5% by weight and 0 to 80% by weight of organic solvent are preferred.
It is a new range. More preferably, represented by the general formula (1)
1 to 10% by weight of water, 30 to 94% by weight of water, organic
The solvent is 5 to 60% by weight. Formula represented by general formula (1)
Compounds may be used alone or in combination.
You may. Also, in order to adjust the hue of the ink,
To the extent that other water-soluble dyes and ink properties are not impaired,
Process known dyes and pigments into emulsions or finely dispersed
It is possible to add a processed material. In the aqueous ink of the present invention, the solvent component is mainly
As water, but prevents ink drying and compound solubility
Water is mixed with an organic solvent for the purpose of improving
You can also. In this case, as an organic solvent that can be used
Is ethylene glycol, diethylene glycol, tri
Ethylene glycol, polyethylene glycol, propylene
Len glycol, polypropylene glycol, 1,3-
Propanediol, glycerin, thioglycol, etc.
Polyhydric alcohols, ethylene glycol monoethyl ether
, Ethylene glycol monobutyl ether, diethyl
Glycol monobutyl ether, dipropylene glycol
Monoethyl ether, triethylene glycol mono
Methyl ether, triethylene glycol monobutyl ether
-Polyhydric alcohol ethers such as
Ketones such as ethyl ketone, N, N-dimethylform
Amide, N, N-diethylformamide, N, N-dimethyl
Amides such as tilacetamide, 2-pyrrolidone, N-
Methyl-2-pyrrolidone, N-vinyl-2-pyrrolidone
Nitrogen, 1,3-dimethyl-2-imidazolidinone, etc.
Ethers such as nitrogen compounds, tetrahydrofuran and dioxane
, Methanol, ethanol, 1-propanol, 2
-Propanol, 1-butanol, 2-butanol and the like
Alcohols and the like. These organic solvents are used alone
Or a mixture of two or more types.
The dose is between 0 and 80% by weight of the water-soluble ink, preferably 5%.
-60% by weight, more preferably 10-40% by weight.
You. The water-based ink of the present invention further improves water resistance.
Ammonia, amines, triethanol
Hydroxyamines such as amines can be used in combination
You. The amount used is 10% by weight or less based on the water-soluble ink.
Below, preferably 0.1 to 5% by weight. These nets
Compounds form a counter ion with the compound represented by the general formula (1).
It may be used after being formed. Also, urea, thiourea and
And derivatives thereof. The amount used is relative to the ink
About 0.1 to 15% by weight, preferably 3 to 10% by weight
is there. Further, the aqueous ink of the present invention is
When used as recording ink,
Various additives conventionally used, for example, UV absorption
Agents, antioxidants, chelating agents, water-soluble polymers,
King agent, fungicide, preservative, viscosity modifier, surfactant
Agent, surface tension adjuster, pH adjuster, specific resistance adjuster,
Infrared absorbers, penetrants and the like can be added. Said
The aqueous ink of the present invention composed of the composition of
Ink or ink jet recording ink
Recording characteristics, storage stability, fixability to recording material, recording
It has excellent image clarity and light fastness. The aqueous ink of the present invention is represented by the following general formula (1).
Compound, water, an organic solvent, if necessary,
After dissolving with the listed additives, remove insolubles
Filter with a small pore size such as a membrane filter
It is produced by filtration through a filter. Made in this way
The produced aqueous ink is an aqueous marker ink, aqueous printing
Ink, ink for recording liquid of inkjet recording system,
It can be used as a dye liquid for inkjet printing, etc.
Wear. Particularly useful as a recording liquid for inkjet recording
It is. In addition, ballpoint pens, felt pens, fountain pens, etc.
Also used as ink for writing instruments. [0041] The present invention will be specifically described below with reference to examples.
However, the present invention is not limited to the following examples.
No. In addition,% and part are “weight%” and “weight part”, respectively.
Represent. Embodiment 1 Compound No. Synthesis of 16 3.6 parts of 2-aminoterephthalic acid, 30 parts of water, and
After charging 6 parts of 36% hydrochloric acid into the flask, the mixture was stirred,
Cooled down to: 13% aqueous solution of sodium nitrite
12 parts of the solution was added dropwise, and after stirring for 1 hour, sulfamic acid was added.
0.1 part was added and stirred for 30 minutes (diazonium salt solution
liquid). On the other hand, 30 parts of water and a compound of the formula (5)
3.5 parts and 15 parts of a 30% aqueous sodium hydroxide solution
Charge into a scoop and cool to below 10 ° C while mixing
Was. [0043] Embedded image Here, the diazonium salt solution was added,
The reaction was performed for 1.5 hours. Here 100 parts of water, 36% hydrochloric acid
After charging 20 parts and stirring for 30 minutes, the precipitated crystals were separated by filtration,
After washing with water and drying, compound No. 16 to 6.
9 parts were obtained (yield 94%). The elemental analysis for this compound is shown below.
It was as shown in the following.                 C% H% N%   Calculated: 59.02 3.85 15.29   Found: 58.86 3.92 15.08 The results of the mass spectrum were as follows. Calculated value: m / z = 366 Actual value: m / z = 366 Compound No. Synthesis of potassium salt of 16 50 parts of distilled water and Compound No. 16, 3.0 parts,
It was charged into a flask and heated to 70 ° C. with stirring.
Here, 9.2 parts of a 10% aqueous potassium hydroxide solution was dropped and charged.
And stirred for 2 hours. This reaction solution is placed in 700 parts of acetone.
The precipitated crystals are separated by filtration, washed with acetone and dried.
In Table 1, Compound No. 3.6 parts of the potassium salt of 16
Was obtained (100% yield). This potassium salt in aqueous solution
The maximum absorption wavelength is 444 nm, and the gram extinction coefficient is 8100.
It was 0 ml / g · cm. Solubility in water is more than 3%
there were. ・ Preparation of ink With the composition shown below, each compound is mixed and dissolved,
Filter through a 0.45 micron pore size membrane filter
To prepare an ink.     In Table 1, Compound No. 16% potassium salt 3%     30% diethylene glycol     N-methyl-2-pyrrolidone 10%     Distilled water 57% ・ Evaluation of characteristics The prepared ink is transferred to a piezo inkjet printer.
-Ink cartridge for EM-930C (manufactured by Seiko Epson Corporation)
Filled into cartridges, printed with the same printer, and lightfast
The sex was evaluated. We also evaluated the storage stability of the ink.
Was. as a result, (A) Light fastness evaluation: ○ (B) Evaluation of storage stability of ink: ○ Was good. The evaluation criteria for each test item are
It is as follows. (A) Light fastness evaluation: Xenon fade meter (Suga Test
After irradiating the printed portion for 100 hours,
The print density (OD value) was measured, and the light resistance was evaluated.     Evaluation criteria: OD value is 80% or more before irradiation: ◎               OD value is 70% or more and less than 80% before irradiation: ○               OD value is 50% or more and less than 70% before irradiation: △               OD value is less than 50% before irradiation: × (B) Evaluation of storage stability of ink: Recording solution was stored at 40 ° C for 3 months.
After storing for a month, record continuously for a long time
The presence or absence of clogging was observed. Embodiment 2 Compound No. Combination of 16 tetramethylammonium salts
Success 50 parts of distilled water and Compound No. 16, 3.0 parts,
It was charged into a flask and heated to 70 ° C. with stirring.
Here 10% tetramethylammonium hydroxide water
15 parts of the solution were added dropwise, and the mixture was stirred for 5 hours. This reaction solution
Was discharged into 600 parts of acetone, and the precipitated crystals were separated by filtration.
After washing with acetone and drying, Compound No. 16 Tetrame
4.0 parts of a tyl ammonium salt were obtained (95% yield). This
The maximum absorption wavelength of the compound in an aqueous solution is 446 nm.
The ram extinction coefficient was 70000 ml / g · cm. water
Solubility in water was 3% or more. ・ Preparation of ink In Table 1, Compound No. Instead of the potassium salt of 16,
Compound No. 1 in Table 1. 16 tetramethylammonium salts
An ink was prepared in the same manner as in Example 1 except that
Was. ・ Evaluation of characteristics The same test as in Example 1 was performed using the prepared ink.
Was. as a result, (A) Light fastness evaluation: ○ (B) Evaluation of storage stability of ink: ○ Was good. Embodiment 3 Compound No. Synthesis of 18 3.6 parts of 2-aminoterephthalic acid, 30 parts of water, and
After charging 6.1 parts of 36% hydrochloric acid into the flask, the mixture was stirred and stirred.
Cooled to below 0 ° C. Here 13% sodium nitrite
An aqueous solution (12 parts) was dropped and stirred for 2 hours.
Acid was added and stirred for 30 minutes (diazonium salt
solution). On the other hand, 30 parts of water and a compound of the formula (6)
4.4 parts, 16 parts of 30% sodium hydroxide aqueous solution mixed
While cooling to 10 ° C. or lower. [0047] Embedded image The diazonium salt solution described above was added thereto,
The reaction was performed for 2 hours. Next, 100 parts of 36% hydrochloric acid was charged.
After stirring for 30 minutes, the precipitated crystals are separated by filtration, washed with water and dried.
In Table 1, Compound No. 8.0 of 18 (yield
97%). The elemental analysis of this compound is shown below.
there were.                 C% H% N%   Calculated: 55.61 3.44 13.65   Found: 55.39 3.56 13.45 The results of the mass spectrum were as follows. Calculated value: m / z = 410 Actual value: m / z = 410 Compound No. Synthesis of sodium salt of 18 50 parts of distilled water and dye No. 3.0 parts of 1
It was charged into a scoop and heated to 70 ° C. with stirring. here
8.8 parts of 10% aqueous sodium hydroxide solution
And stirred for 2 hours. This reaction solution is placed in 500 parts of acetone.
The precipitated crystals are separated by filtration, washed with acetone and dried.
Compound No. 3.4 parts of the sodium salt of 18 were obtained.
(Yield 98%) The maximum absorption wavelength of this compound in an aqueous solution is 446 nm,
The gram extinction coefficient was 80000 ml / g · cm.
The solubility in water was 3% or more. ・ Preparation of ink In Table 1, Compound No. Instead of the potassium salt of 16,
Compound No. 1 in Table 1. Except for using the sodium salt of 18
An ink was prepared in the same manner as in Example 1. ・ Evaluation of characteristics The same test as in Example 1 was performed using the prepared ink.
Was. as a result, (A) Light fastness evaluation: ◎ (B) Evaluation of storage stability of ink: ○ Was good. Examples 4 to 30 According to Example 1 using various compounds described in Table 1
Inks were prepared and evaluated for light fastness and storage stability. So
As a result, as shown in Table 2 (Table 4), the
Has excellent light fastness and long-term storage stability
It turned out to show. [0050] [Table 4]Comparative Example 1 Yellow azo dye (CI Acid Yellow)
ow 23) according to the ink preparation method of Example 1.
The ink was prepared and the characteristics were evaluated in the same manner. The result
Fruit (A) Light resistance evaluation: × (B) Evaluation of storage stability of ink: ○ And light resistance was inferior to the ink of the present invention. Comparative Example 2 Using the pyridone azo compound of the formula (2),
Prepare the ink according to the ink preparation method and evaluate the characteristics in the same way.
Was done. as a result, (A) Light resistance evaluation: × (B) Evaluation of storage stability of ink: ○ And light resistance was inferior to the ink of the present invention. [0053] EFFECT OF THE INVENTION The compound represented by the general formula (1) or
The aqueous ink of the present invention containing a salt of
And shows excellent performance in light resistance and storage stability. Especially in
When used as ink for jet recording,
It becomes a recording liquid with high quality and excellent light resistance.

   ────────────────────────────────────────────────── ─── Continuation of front page    (72) Inventor Akira Ogiso             580-32 Nagaura, Sodegaura City, Chiba Prefecture Mitsui Chemicals, Inc.             Inside the company (72) Inventor Yasunori Saito             580-32 Nagaura, Sodegaura City, Chiba Prefecture Mitsui Chemicals, Inc.             Inside the company (72) Inventor Densumi Misawa             580-32 Nagaura, Sodegaura City, Chiba Prefecture Mitsui Chemicals, Inc.             Inside the company F term (reference) 2C056 EA13 FC02                 2H086 BA56                 4J039 BC03 BC05 BC07 BC19 BC36                       BC40 BC51 BC54 CA03 CA06                       EA21 EA35 GA24 GA26 GA27                       GA28 GA29

Claims (1)

[Claims] (1) a compound represented by the general formula (1):
Or an aqueous ink containing the salt thereof. Embedded image [Wherein, R₁~ R_FourAre each independently a hydrogen atom, halogen
Atom, substituted or unsubstituted alkyl group, substituted or unsubstituted
Substituted aryl group, hydroxyl group, -COOH, -SO _ThreeH,
-CONR₇R₈(Where R₇, R₈Are each independently water
Elemental atom, substituted or unsubstituted alkyl group, substituted or unsubstituted
A substituted aryl group or a substituted or unsubstituted hetero
A ring group;₇And R₈Is a substituted or unsubstituted alkylene
A ring may be formed by a group) or -SO_Two
R₉R_Ten(Where R₉, R_TenAre each independently a hydrogen source
, Substituted or unsubstituted alkyl group, substituted or unsubstituted
An aryl group or a substituted or unsubstituted heterocyclic group
And R₇And R₈Represents a substituted or unsubstituted alkylene group
May form a ring),_FiveIs a methyl group
Or -COOH;₆Is a substituted or unsubstituted
Represents a alkyl group or a substituted or unsubstituted aryl group.
You. Where R₁~ R_FourAt least one of which is -COO
H. ]