WO2016067865A1 - Sel métallique alcalin de colorant azoïque, sel métallique alcalino-terreux ainsi que tautomère de celui-ci, composition colorante, procédé de teinture et produit teinté - Google Patents

Sel métallique alcalin de colorant azoïque, sel métallique alcalino-terreux ainsi que tautomère de celui-ci, composition colorante, procédé de teinture et produit teinté Download PDF

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WO2016067865A1
WO2016067865A1 PCT/JP2015/078536 JP2015078536W WO2016067865A1 WO 2016067865 A1 WO2016067865 A1 WO 2016067865A1 JP 2015078536 W JP2015078536 W JP 2015078536W WO 2016067865 A1 WO2016067865 A1 WO 2016067865A1
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group
heterocyclic
alkyl
aryl
groups
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神保　良弘
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富士フイルム株式会社
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
    • D06P1/10—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes containing metal
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form

Definitions

  • the present invention relates to a novel azo dye alkali metal salt, alkaline earth metal salt and tautomer thereof having a good hue and fastness and a high molecular extinction coefficient, and further, a coloring composition using them Article, dyeing method, and dyed article.
  • azo dyes often have various visible light absorption, they have been used as dyes in various fields. For example, it has come to be used in various fields such as coloring of synthetic resins, printing inks, dyes for sublimation thermal transfer materials, inks for inkjets, and dyes for color filters.
  • color images have become mainstream as image recording materials, and the uses of dyes have also diversified. Specifically, it is actively used for inkjet recording materials, thermal transfer recording materials, electrophotographic recording materials, transfer silver halide photosensitive materials, printing inks, and the like.
  • a color filter that records and reproduces a color image is used in an imaging device such as a CCD or a CMOS in a photographing apparatus and in an LCD or a PDP in a display.
  • three primary colorants (dyes or pigments) of the so-called additive color mixture method or subtractive color mixture method are used to reproduce or record a full color image.
  • the present situation is that there is no colorant that has an absorption characteristic capable of realizing a preferable color gamut, can withstand various use conditions and environmental conditions, and has a good hue and is robust, and improvement is strongly desired.
  • Examples of conventional azo dyes having dissociable protons include azo dyes disclosed in Japanese Patent No. 4080947.
  • An object of one embodiment of the present invention is to provide alkali metal salts, alkaline earth metal salts and tautomers of azo dyes having a novel dissociative proton having a good hue and fastness and a high molecular extinction coefficient. Is to provide.
  • the present inventor has found that the alkali metal salts, alkaline earth metal salts and tautomers of the azo dyes having a novel dissociative proton have a good hue and good fastness. As a result, the present invention has been completed.
  • the present invention includes the following aspects.
  • a ⁇ N NB
  • A is a heterocyclic group represented by any of the following formulas (A-1) to (A-25) which may have a substituent, and is a carboxy group or a sulfo group. A group which does not contain and is bonded to an azo group via a carbon atom is shown.
  • R 21 to R 50 are independently hydrogen atom, halogen atom, alkyl group, aryl group, heterocyclic group, cyano group, hydroxyl group, nitro group, alkoxy group, aryloxy group, amino group (including anilino group), acylamino Group, aminocarbonylamino group, alkoxycarbonylamino group, alkylsulfonylamino group, arylsulfonylamino group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, alkylsulfonyl group, arylsulfonyl group, acyl group, alkoxycarbonyl group Alternatively, it represents a carbamoyl group, and adjacent groups among R 21 to R 50 may be bonded to each other to form a saturated or unsaturated 5-membere
  • B represents a group containing a dissociable proton represented by any of the following formulas (B-1) to (B-12) and not containing a carboxy group or a sulfo group.
  • R 101 is a halogen atom, alkyl group, aryl group, heterocyclic group, cyano group, alkoxy group, amino group (including anilino group), acylamino group, alkylsulfonylamino group, arylsulfonylamino group, alkylthio group, arylthio group, Represents a sulfamoyl group, an alkylsulfonyl group or a carbamoyl group
  • R 102 and R 104 are each independently a cyano group, alkylsulfonyl group, arylsulfonyl group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, arylsulfonyl group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group or carb
  • Z 1 represents an oxygen atom, a sulfur atom or —N (R 103 ) —
  • R 103 represents a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group
  • v represents an integer of 0 to 4
  • R 101s may be the same or different.
  • R 105 and R 106 independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R107 represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group (including an anilino group), an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group, an arylthio group.
  • Z 2 and Z 3 independently represent —C (R 108 ) ⁇ or —N ⁇
  • R 108 represents an alkyl group, an aryl group, a heterocyclic group, an alkylthio group, an arylthio group, an alkoxycarbonyl group or a carbamoyl group
  • Z 2 and Z 3 are both —C (R 108 ) ⁇
  • the two R 108 groups may be the same or different and are bonded together to form a carbocyclic or heterocyclic ring. Also good.
  • R 109 represents an alkyl group, an aryl group or a heterocyclic group
  • R 110 represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an acyl group, an alkylsulfonyl group or an arylsulfonyl group
  • R 111 represents an alkyl group, an aryl group, an alkoxy group, an amino group (including anilino group), an alkoxycarbonyl group, a cyano group, an acylamino group or a carbamoyl group
  • R 112 represents a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group
  • R 113 Represents a hydroxyl group or an amino group.
  • R 114 and R 115 are halogen atoms, alkyl groups, aryl groups, heterocyclic groups, nitro groups, alkoxy groups, aryloxy groups, amino groups (including anilino groups), acylamino groups, alkoxycarbonylamino groups, aminocarbonylamino groups.
  • w represents an integer of 0 to 4, and w R 114 groups may be the same or different.
  • R x represents an integer of 0 to 6, and the x R 115 groups may be the same or different.
  • R 116 , R 117 , R 118 and R 119 independently represent an alkyl group or an aryl group.
  • R 120 and R 121 independently represent an alkyl group, an aryl group, a heterocyclic group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, an alkoxycarbonyl group, or a carbamoyl group
  • R 122 represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an acylamino group, an alkylsulfonylamino group or an arylsulfonylamino group.
  • R 123 and R 124 independently represent an alkyl group, an aryl group, a heterocyclic group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, an alkoxycarbonyl group, or a carbamoyl group
  • Z 4 represents a nonmetallic atomic group that forms a 5- or 6-membered ring with two nitrogen atoms and one carbon atom
  • y represents an integer of 0-2
  • Z 4 forms a 6-membered ring y represents an integer of 0-3
  • R 125 represents an alkyl group, aryl group, alkoxy group, amino group, acylamino group, alkylsulfonylamino group, arylsulfonylamino group, alkylthio group, arylthio group, acyl group, alkoxycarbonyl group or carbamoyl group
  • R 126 represents an alkyl group, an aryl group
  • R 201 represents an alkyl group, an aryl group, an alkoxy group, an amino group (including an anilino group), an alkoxycarbonyl group, a cyano group, an acylamino group, or a carbamoyl group
  • R 202 represents a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group
  • R 203 , R 205 and R 207 are each independently a hydrogen atom, alkyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, amino group (including anilino group), acylamino group, alkylsulfonylamino group , an arylsulfonylamino group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group,
  • R 206 represents an alkyl group, an aryl group, a heterocyclic group, an alkylthio group, an arylthio group, an alkoxycarbonyl group or a carbamoyl group.
  • R 208 is a halogen atom, alkyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, amino group (including anilino group), acylamino group, alkylsulfonylamino group, arylsulfonylamino group, alkylthio group, arylthio group Represents an alkylsulfonyl group, an arylsulfonyl group, an alkoxycarbonyl group or a carbamoyl group, aa represents an integer of 0 to 4, and aa R 208 may be the same or different.
  • R 210 and R 211 are independently a hydrogen atom, halogen atom, alkyl group, aryl group, acylamino group, alkoxycarbonyl group, aminocarbonylamino group, alkylsulfonylamino group, arylsulfonylamino group, alkoxycarbonylamino group or carbamoyl. And at least one of R 210 and R 211 is a hydrogen atom, and R 212 and R 213 independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an acylamino group.
  • R 214 and R 215 independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R216 is a halogen atom, alkyl group, aryl group, heterocyclic group, cyano group, alkoxy group, amino group (including anilino group), acylamino group, alkylsulfonylamino group, arylsulfonylamino group, alkylthio group, arylthio group , A sulfamoyl group, an alkylsulfonyl group or a carbamoyl group, Z 5 represents an oxygen atom, a sulfur atom or —N (R 217 ) —, and R 217 represents a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group.
  • R 216s may be the same or different.
  • R 218 is synonymous with R 210 or represents a sulfamoyl group
  • R 220 and R 223 are a hydrogen atom, a halogen atom, an acylamino group, an alkoxycarbonylamino group, an aminocarbonylamino group, an alkylsulfonylamino group or an arylsulfonylamino group.
  • R 219 , R 221 and R 222 represent a hydrogen atom, a chlorine atom, a bromine atom, an alkyl group or an acylamino group.
  • R 224 represents an alkylcarbonyl group or an arylcarbonyl group.
  • M represents alkali metal or alkaline earth metal 1/2
  • the alkali metal salt, alkaline earth metal salt and tautomer thereof of the azo dye of the present invention are excellent in hue and are effective against light, heat, humidity and the active gas in the environment.
  • novel compounds and dyes having sufficient fastness and a high molecular absorption coefficient can be provided.
  • This relates to the reflection spectrum of the dyed product obtained in Example 15. This relates to the reflection spectrum of the dyed product obtained in Example 16. This relates to the reflection spectrum of the dyed product obtained in Example 17.
  • a numerical range expressed using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • the amount of each component in the composition is the total amount of the plurality of substances present in the composition unless there is a specific indication when there are a plurality of substances corresponding to each component in the composition. Means.
  • the alkali metal salt, alkaline earth metal salt and tautomer thereof of an azo dye according to one embodiment of the present invention are an alkali metal salt and an alkaline earth metal salt of an azo dye represented by the following general formula (1). And tautomers thereof.
  • a and B in the general formula (1) have the same meaning as described above. That is, the alkali metal salt, alkaline earth metal salt and tautomer thereof of the azo dye of the present invention are represented by the above formula in which A may have a substituent in the general formula (1) described in detail below.
  • the general formula (1) will be described in detail.
  • the heterocyclic group represented by A is a 5-membered or 6-membered heterocyclic group containing one or more heteroatoms selected from an oxygen atom, a sulfur atom or a nitrogen atom in the ring.
  • the aromatic heterocyclic group is more preferable.
  • the heterocyclic group represented by A may be a ring condensed with another ring. Of such fused ring groups, those fused with a 5-membered or 6-membered ring are preferred.
  • the number of carbon atoms in the heterocyclic group represented by A is preferably 2 to 20, and more preferably 2 to 10.
  • the heterocyclic group represented by A in the general formula (1) those derived from a diazo component are preferable.
  • the diazo component is a partial structure that can be introduced by converting a heterocyclic compound having an amino group as a substituent into a diazo compound and reacting with a coupler by a diazo coupling reaction.
  • the heterocyclic group represented by A is a substituent which is a monovalent group by removing the amino group in an amino-substituted heterocyclic compound capable of diazotization reaction.
  • the heterocyclic group represented by A can include one or more substituents, and the two or more substituents may be the same or different.
  • substituents include a halogen atom, an alkyl group (including a cycloalkyl group), an alkenyl group (including a cycloalkenyl group), an alkynyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxyl group, a nitro group, and an alkoxy group.
  • aryloxy group silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy, amino group (including anilino group), acylamino group, aminocarbonylamino group, alkoxycarbonyl Amino group, aryloxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, alkylsulfinyl group Arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, arylazo group, heterocyclic
  • examples of the substituent include a halogen atom (for example, a chlorine atom, a bromine atom, and an iodine atom), an alkyl group (a straight chain having 1 to 10, preferably 1 to 6 carbon atoms, Branched or cyclic alkyl groups such as methyl, ethyl, n-propyl, isopropyl, t-butyl, n-octyl-2-chloroethyl-2-cyanoethyl-2-ethylhexyl, cyclopropyl, cyclopentyl), alkenyl groups (2-10 Linear, branched or cyclic alkenyl groups having 2 to 6 carbon atoms, such as vinyl, allyl, prenyl, cyclopenten-1-yl, alkynyl groups (2 to 10, preferably 2 to 6) Alkynyl groups having 1 carbon atom, eg ethynyl, propargyl),
  • these groups are groups that can be further substituted, these groups can further contain a substituent, and this substituent is preferably described as a preferred substituent of the heterocyclic group represented by A. And groups having the same meaning. When these groups are substituted with two or more substituents, these substituents may be the same or different.
  • the substituent of the heterocyclic group represented by A in the general formula (1) is a halogen atom, alkyl group, aryl group, heterocyclic group, cyano group, hydroxyl group, nitro group, alkoxy group, aryloxy Group, amino group (including anilino group), acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, alkylsulfonylamino group, arylsulfonylamino group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, alkylsulfonyl Group, arylsulfonyl group, acyl group, alkoxycarbonyl group and carbamoyl group, and more preferably, this substituent is a halogen atom, alkyl group, cyano group, hydroxyl group, nitro group, alkoxy group, amino group (anilino group),
  • heterocyclic group represented by A examples include heterocyclic groups represented by any one of the above formulas (A-1) to (A-25) which may have a substituent.
  • R 21 to R 50 independently represent a hydrogen atom or a substituent, preferably a halogen atom, an alkyl group, an aryl group, a heterocyclic group, cyano Group, hydroxyl group, nitro group, alkoxy group, aryloxy group, amino group (including anilino group), acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, alkylsulfonylamino group, arylsulfonylamino group, alkylthio group, arylthio Group, heterocyclic thio group, sulfamoyl group, alkylsulfonyl group, arylsulfonyl group, acyl group, alkoxycarbonyl group and carbam
  • a, p, q, r and s represent an integer of 0 to 4
  • b and c represent an integer of 0 to 6
  • d, e, f, g, t and u represent an integer of 0 to 3
  • h, i, j, k, l, and o represent an integer of 0 to 2
  • m represents an integer of 0 to 1.
  • groups adjacent to each other represented by R 21 to R 50 may be bonded to form a ring structure.
  • the ring structure thus formed may be a heterocyclic ring or a carbocyclic ring, and may be a saturated ring or an unsaturated ring.
  • the total number of carbon atoms and heteroatoms is 3-6, preferably 5 or 6.
  • R 21 to R 50 can further include a substituent.
  • the substituent is represented by A in the general formula (1). The same as those listed as the substituent of the heterocyclic group.
  • the heterocyclic group represented by A is preferably a group represented by the formula (A-1), (A-5), (A-8), (A -9), (A-10), (A-11), (A-12), (A-13), (A-14), (A-15), (A-17), (A-19) ), (A-22), (A-23), (A-24) and (A-25), more preferably (A-8), (A-9), (A-10), (A A-11), (A-14), (A-15), (A-22) and (A-23).
  • B in the general formula (1) represents an atomic group essential for forming the azo dye represented by the general formula (1), and is preferably derived from a coupler component.
  • the coupler component means a partial structure derived from a coupler compound that can react with a diazonium salt to obtain an azo dye.
  • the carbon number of B in the azo dye represented by the general formula (1) is preferably 3 to 30, more preferably 3 to 20, and further preferably 3 to 12.
  • B in the general formula (1) is a 5-membered or 6-membered heterocyclic ring or condensed condensed ring containing one or more heteroatoms selected from a sulfur atom, a nitrogen atom or an oxygen atom; An optionally fused aromatic ring; or a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group or a C 2 -C 6 alkynyl group, optionally containing an ⁇ -CO group, of these rings and groups Each can contain one or more substituents.
  • the coupler component is preferably a residue of what is known as a coupler in the field of silver halide color photographic materials.
  • Research Disclosure 37038 (February 1995), pages 80 to 85, and pages 87 to 89.
  • the skeleton portion of a silver halide color photographic coupler described in detail on the page (the portion which becomes a chromophore of a dye upon coupling with an oxidized aromatic amine developing agent such as p-phenylenediamine) can be used.
  • couplers known as yellow color image-forming couplers in the field of silver halide color photographic materials include pivaloyl acetamide type, benzoylacetamide type, malon diester type, malon diamide type, dibenzoyl methane type, benzo type.
  • couplers known as magenta color image forming couplers in the field of silver halide color photographic light-sensitive materials include 5-pyrazolone type, 1H-pyrazolo [1,5-a] benzimidazole type, 1H-pyrazolo [5, 1-c] [1,2,4] triazole type, 1H-pyrazolo [1,5-b] [1,2,4] triazole type, 1H-imidazo [1,2-b] pyrazole type, cyanoacetophenone type ,
  • couplers known as cyan image forming couplers in the field of silver halide color photographic light-sensitive materials include phenol type, naphthol type, and 2,5-diphenylimidazole described in European Patent Application No. 0249453.
  • Examples of the group represented by B include groups represented by any of the above formulas (B-1) to (B-12).
  • R 101 is preferably a halogen atom, an acylamino group, an alkylsulfonylamino group, a sulfamoyl group and a carbamoyl group
  • R 102 is preferably a cyano group and a carbamoyl group
  • 1 is preferably an oxygen atom, a sulfur atom or —N (R 103 ) — in which R 103 is an alkyl group.
  • v represents an integer of 0 to 4. When v is 1 to 4, the R 101 groups may be the same or different.
  • R 104 is preferably a cyano group, an acyl group, or a carbamoyl group, and one of R 105 and R 106 is preferably a hydrogen atom.
  • R 107 is preferably a hydrogen atom, an alkyl group or an aryl group, and more preferably a hydrogen atom or an alkyl group.
  • R 108 is preferably an alkyl group, an aryl group or a heterocyclic ring, and more preferably an alkyl group.
  • R 109 is preferably an alkyl group or an aryl group
  • R 110 is preferably a hydrogen atom or an alkyl group.
  • R 111 is preferably an alkoxycarbonyl group, a cyano group, or a carbamoyl group
  • R 112 is preferably an alkyl group or an aryl group.
  • R 114 is preferably a halogen atom, an alkyl group, an acylamino group, an alkoxycarbonylamino group, an aminocarbonylamino group, an alkylsulfonylamino group, an arylsulfonylamino group or a carbamoyl group. More preferably, they are an atom, an alkyl group, an acylamino group, or an alkylsulfonylamino group.
  • w represents an integer of 0 to 4, and when w is 2 to 4, the R 114 groups may be the same or different.
  • R 115 is preferably a halogen atom, an acylamino group, an alkoxycarbonylamino group, an aminocarbonylamino group, an alkylsulfonylamino group, an arylsulfonylamino group or a carbamoyl group.
  • a sulfonylamino group or a carbamoyl group is more preferable.
  • x represents an integer of 0 to 6, and when x is 2 to 6, the R 115 groups may be the same or different.
  • R 116 and R 117 , and R 118 and R 119 are preferably the same as each other.
  • R 120 and R 121 are preferably an alkyl group, an aryl group, a heterocyclic group, or a cyano group
  • R 122 is a hydrogen atom, an alkyl group, an aryl group, an acylamino group, or an alkylsulfonyl group.
  • An amino group is preferred.
  • R 123 is preferably an alkyl group, an aryl group, a heterocyclic group, or a cyano group
  • R 124 is an alkylsulfonyl group, an arylsulfonyl group, an alkoxycarbonyl group, or a carbamoyl group
  • R 125 is preferably an alkyl group, an aryl group, an alkylthio group, an amino group, or an acylamino group.
  • R 126 is preferably an alkyl group or an aryl group.
  • R 101 to R 126 in formulas (B-1) to (B-12) are groups that can be further substituted, R 101 to R 126 can further have a substituent, and in this case, the substituent Are the same as those enumerated as substituents of the heterocyclic group represented by A in the general formula (1).
  • azo dyes represented by the general formula (1) are particularly preferable.
  • a in the formulas DS-1 to DS-9 has the same meaning as A in the general formula (1).
  • R 201 represents an alkyl group, an aryl group, an alkoxy group, an amino group (including an anilino group), an alkoxycarbonyl group, a cyano group, an acylamino group, or a carbamoyl group
  • R 202 represents a hydrogen atom
  • R 201 is preferably an alkoxycarbonyl group, a cyano group, or a carbamoyl group
  • R 202 is preferably an alkyl group or an aryl group.
  • R 203 represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group (including an anilino group), an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group. It represents group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, or carbamoyl group, R 204 represents an alkyl group, an aryl group or a heterocyclic group.
  • R 203 is preferably a hydrogen atom or an alkyl group, and the alkyl group is more preferably a methyl group, an ethyl group, an isopropyl group or a t-butyl group.
  • R 204 is preferably an alkyl group.
  • R 205 represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group (including an anilino group), an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group.
  • R 206 represents an alkyl group, an aryl group, a heterocyclic group, an alkylthio group, an arylthio group, an alkoxycarbonyl group or a carbamoyl group.
  • R 205 is preferably a hydrogen atom or an alkyl group, and the alkyl group is more preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group.
  • R 206 is preferably an alkyl group, an aryl group or an alkylthio group, and more preferably an alkyl group.
  • R 207 represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group (including an anilino group), an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group.
  • R 208 represents a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an amino group (an anilino group).
  • acylamino group an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an alkoxycarbonyl group, or a carbamoyl group, aa represents an integer of 0 to 4, aa number of R 08 may be the same or different.
  • R 207 is preferably a hydrogen atom or an alkyl group, and the alkyl group is more preferably a methyl group, an ethyl group, an isopropyl group or a t-butyl group.
  • R 208 is preferably a halogen atom, an alkyl group, an alkoxy group, an acylamino group, or an alkylsulfonylamino group.
  • R 210 and R 211 are a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an acylamino group, an alkoxycarbonyl group, an aminocarbonylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkoxycarbonylamino.
  • R 212 and R 213 represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or an acylamino group.
  • R 210 and R 211 are preferably a hydrogen atom, a chlorine atom, a bromine atom, an alkyl group or an acylamino group, and more preferably at least one of R 210 and R 211 is a hydrogen atom.
  • R 214 and R 215 independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group, and one of R 214 and R 215 is preferably a hydrogen atom.
  • R 216 is a halogen atom, alkyl group, aryl group, heterocyclic group, cyano group, alkoxy group, amino group (including anilino group), acylamino group, alkylsulfonylamino group, arylsulfonylamino group , an alkylthio group, an arylthio group, a sulfamoyl group, an alkylsulfonyl group or a carbamoyl group, Z 5 represents an oxygen atom, a sulfur atom, or -N (R217) - represents, R 217 is a hydrogen atom, an alkyl group, an aryl group Or represents a heterocyclic group.
  • R 216 is preferably a halogen atom, an acylamino group, an alkylsulfonylamino group, a sulfamoyl group or a carbamoyl group.
  • Z 5 is preferably an oxygen atom, a sulfur atom, or —N (R 217 ) — in which R 217 is an alkyl group, and more preferably Z 5 is an oxygen atom or a sulfur atom.
  • R 218 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkoxycarbonyl group, an aminocarbonylamino group, a carbamoyl group, or a sulfamoyl group.
  • R 220 and R 223 represent a hydrogen atom, a halogen atom, an acylamino group, an alkoxycarbonylamino group, an aminocarbonylamino group, an alkylsulfonylamino group or an arylsulfonylamino group
  • R 219 , R 221 and R 222 are A hydrogen atom, a chlorine atom, a bromine atom, an alkyl group or an acylamino group is represented.
  • R 218 is preferably a hydrogen atom, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkoxycarbonyl group, an aminocarbonylamino group, a carbamoyl group, and a sulfamoyl group, and R 220 and R 223 are a hydrogen atom.
  • An acylamino group, an alkoxycarbonylamino group or an alkylsulfonylamino group, and R 219 , R 221 and R 222 are preferably hydrogen atoms.
  • R 224 represents an alkyl group or an aryl group.
  • M represents an alkali metal or an alkaline earth metal 1/2.
  • alkali metal lithium, sodium, potassium, and cesium are preferable, and sodium and potassium are more preferable.
  • Alkaline earth metal 1/2 is an alkaline earth metal in the state where one alkaline earth metal ion is bonded to two molecules of the dissociated azo dye of the general formula (1) having a dissociating proton.
  • alkaline earth metal calcium, strontium and barium are preferable, and calcium and barium are more preferable.
  • R 201 to R 224 in the formulas DS-1 to DS-9 are groups with the possibility of further substitution, these can have further substituents.
  • the substituent is the same as that described in the description of the substituent for the heterocyclic group represented by A in the general formula (1).
  • alkali metal salt and alkaline earth metal salt of the azo dye represented by the general formula (1) are described below, but are not limited by these examples.
  • the azo dye represented by the general formula (1) can be synthesized, for example, by the method described in Japanese Patent No. 4080947.
  • the alkali metal salt, alkaline earth metal salt and tautomer thereof of the azo dye represented by the general formula (1) are prepared by replacing the azo dye represented by the general formula (1) with the corresponding alkali metal salt, alkaline earth salt. It can be obtained by reacting with a metal salt.
  • Examples of the alkali metal salt that can be used in the reaction include lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, potassium t-butoxide. And sodium hydride.
  • Examples of the alkaline earth metal salt that can be used for the reaction include magnesium hydroxide, magnesium chloride, magnesium acetate, calcium hydroxide, calcium chloride, calcium acetate, barium hydroxide, barium chloride, and barium acetate.
  • the alkali metal salt, alkaline earth metal salt and tautomer thereof of the azo dye represented by the general formula (1) are prepared by replacing the azo dye represented by the general formula (1) with the corresponding alkali metal salt, alkaline earth salt.
  • a solvent As the solvent that can be used, water, methanol, ethanol, n-propanol, isopropanol, t-butanol and the like are preferable.
  • the reaction temperature is preferably ⁇ 20 ° C. to the boiling point of the reaction solvent, more preferably room temperature to 100 ° C.
  • the alkali metal salt, alkaline earth metal salt or tautomer of the azo dye according to one embodiment of the present invention is preferably used as a coloring composition, and the alkali metal salt of the azo dye, the alkali A colored composition containing an earth metal salt or a tautomer is more preferable.
  • the dyeing method using the alkali metal salt, alkaline earth metal salt or tautomer of the azo dye according to one embodiment of the present invention includes the alkali metal salt, alkaline earth metal salt or tautomer of the azo dye of the present invention.
  • Mutant bodies can be used in methods such as dipping, kneading, coating, printing, or inkjet printing.
  • the dyeing materials include cashmere, wool, silk, cotton, hemp and other natural fibers, nylon, polyester, acrylic, polyurethane and other inorganic materials, glass, metal, ceramics and other inorganic materials, plain paper, resin-coated paper, and inkjet. Paper such as dedicated recording paper can be used.
  • alkali metal salt, alkaline earth metal salt and tautomer thereof of the azo dye represented by the general formula (1) are used for solid-state imaging devices such as CCD and CMOS, and displays such as LCD and PDP.
  • solid-state imaging devices such as CCD and CMOS
  • displays such as LCD and PDP.
  • Examples thereof include a color filter for reproducing a color image, a curable composition for producing these color filters, and a color image recording material for forming a color image.
  • color filters and curable compositions for producing these color filters ink jet recording materials, sublimation thermal recording materials, recording materials using electrophotographic methods, transfer type silver halide photosensitive materials, printing It is used for ink, recording pen, fiber dyeing, hair dyeing and the like, and preferably used for ink jet recording material, transfer type silver halide photosensitive material, printing ink, fiber dyeing and the like.
  • the alkali metal salt, alkaline earth metal salt, and tautomer thereof of the azo dye according to one embodiment of the present invention can be obtained by adjusting the physical properties such as solubility and dispersibility suitable for the application by adjusting substituents. Can be optimized and used.
  • the alkali metal salt, alkaline earth metal salt and tautomer thereof of the azo dye of the present embodiment can be used in a dissolved state, an emulsified dispersion state, and a solid dispersion state depending on the system used.
  • the colored composition of the present embodiment means a composition containing at least one of an alkali metal salt, an alkaline earth metal salt and a tautomer thereof of the azo dye represented by the general formula (1).
  • the alkali metal salt, alkaline earth metal salt and tautomer thereof of the azo dye represented by the general formula (1) may be used alone or other direct dyes or You may use it in combination with a disperse dye.
  • the coloring composition of the present embodiment can contain a medium.
  • the coloring composition of the present embodiment uses a lipophilic medium or an aqueous medium as a medium, and includes an alkali metal salt or alkaline earth metal salt of an azo dye that is a compound according to an embodiment of the present invention. And its tautomers can be made by dissolving and / or dispersing.
  • an aqueous medium is used.
  • the total content of the alkali metal salt, alkaline earth metal salt and tautomer of the azo dye represented by the general formula (1) contained in the coloring composition is the general formula (1) used in the coloring composition.
  • the total content of the alkali metal salt, alkaline earth metal salt and tautomer thereof of the azo dye represented by the general formula (1) in the coloring composition is 0.001 with respect to the total mass of the coloring composition. It is preferably contained in an amount of ⁇ 20% by mass, more preferably 0.1 ⁇ 10% by mass.
  • the total content of the alkali metal salt, alkaline earth metal salt and tautomer thereof of the azo dye represented by the general formula (1) By coloring the total content of the alkali metal salt, alkaline earth metal salt and tautomer thereof of the azo dye represented by the general formula (1) to 0.001% by mass or more, coloring of the dye on the coloring medium The concentration can be secured. Moreover, the low-viscosity coloring composition is obtained by setting the total content of the alkali metal salt, alkaline earth metal salt and tautomer thereof of the azo dye represented by the general formula (1) to 20% by mass or less. It can be adjusted and is easy to handle.
  • the coloring composition containing at least one selected from the alkali metal salts, alkaline earth metal salts and tautomers thereof of the azo dye represented by the general formula (1) has any pH within the range of pH 5-11.
  • the colored composition is preferably used in the range of pH 6 or higher, from the viewpoint of the stability and dyeability of alkali metal salts, alkaline earth metal salts and tautomers thereof of azo dyes. It is more preferable to use in the range of pH 7-11.
  • pH adjuster used in the coloring composition of the present embodiment examples include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, ammonia, monoethanolamine, diethanolamine, guanidine, and the like. Is mentioned.
  • the coloring composition of the present embodiment can contain a surfactant.
  • a surfactant that can be used, an anionic, nonionic, cationic, amphoteric or zwitterionic surfactant can be added.
  • surfactant may be used individually by 1 type and may be used in combination of 2 or more types.
  • anionic surfactant examples include monoalkyl sulfuric acid or a salt thereof, alkylbenzene sulfonic acid or a salt thereof, and ⁇ -olefin sulfonate or a salt thereof.
  • Particularly preferred are sodium dodecylbenzenesulfonate, sodium dodecylsulfate, and alkali salts of sulfosuccinic acid half ester, such as monooctylsulfosuccinic acid disodium salt and long-chain monoalkylethoxysulfosuccinic acid alkali salt.
  • nonionic surfactant examples include alkyl polyglycosides; sorbitan esters such as polyethylene glycol sorbitan stearate.
  • Examples of the cationic surfactant that can be used in the coloring composition of the present embodiment include a long-chain quaternary ammonium compound.
  • Examples of long-chain quaternary ammonium compounds include cetyltrimethylammonium chloride, dimethylstearylammonium chloride, trimethylacetylammonium bromide, stearyltrimethylammonium chloride, dimethylstearylbenzylammonium chloride, benzyltetradecyldimethylammonium chloride, dimethyldi-hydrogenated-tallow Examples include ammonium chloride, lauryldimethylbenzylammonium chloride, behenyltrimethylammonium chloride, lauryltrimethylammonium chloride, tris (oligooxy-ethyl) alkylammonium phosphate, cetylpyridinium chloride and the like.
  • amphoteric or zwitterionic surfactants that can be used in the coloring composition of the present embodiment include fatty acids-amide alkylbetaines, sulfobetaines and the like (eg, lauryl hydroxysulfobetaine), cocoaminoacetate, cocoaminopro Long chain alkyl amino acids such as pionate, sodium cocoamphopropionate, sodium cocoamphoacetate and the like can be mentioned.
  • aqueous solvent When the coloring composition of the present embodiment is used as an aqueous coloring composition, the following aqueous solvent can be used in combination.
  • Usable aqueous solvents include ethanol, isopropanol, n-propanol, butanol, n-pentanol, propylene glycol, ethylene glycol monoethyl ether, 1,2-hexanediol, butoxyethanol, phenoxyethanol, benzyl alcohol, propylene carbonate, and And mixtures thereof, among which 1,2- or 1,3-propanediol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, 1,3- or 1,4-butane Diol, diethylene glycol and its monomethyl or monoethyl ether, and dipropylene glycol and its monomethyl or monoethyl ether are preferred.
  • the blending amount of these aqueous solvents is preferably 0.5 to 30% by mass, more preferably 1 to 15% by mass, and further preferably 5 to 10% by mass with respect to the total mass of the colored composition.
  • a component selected from polyhydric alcohols such as glycerin and hexanetriol; ethyl carbitol; benzyl alcohol; benzyloxyethanol; n-alkylpyrrolidone; and urea may be used in combination.
  • the coloring composition of the present embodiment can contain a thickener.
  • the blending amount of the thickener is preferably 0.05 to 20% by mass, more preferably 0.1 to 10% by mass, and more preferably 0.5 to 5% with respect to the total mass of the coloring composition. More preferably, it is mass%.
  • the thickener that can be used for the colored composition of the present embodiment include oleic acid, cetyl alcohol, oleyl alcohol, sodium chloride, cetearyl alcohol, and stearyl alcohol.
  • the colored composition of the present embodiment contains other colored compounds together with at least one selected from alkali metal salts, alkaline earth metal salts and tautomers thereof of the azo dye represented by the general formula (1).
  • magenta dye that can be used can be used.
  • magenta dyes include aryl or heteryl azo dyes having phenols, naphthols, anilines, etc. as coupler components; azomethine dyes having pyrazolones, pyrazolotriazoles, etc.
  • coupler components arylidene dyes, styryl dyes, merocyanine dyes Methine dyes such as cyanine dyes and oxonol dyes; carbonium dyes such as diphenylmethane dyes, triphenylmethane dyes and xanthene dyes; quinone dyes such as naphthoquinone, anthraquinone and anthrapyridone; condensations such as dioxazine dyes Examples include polycyclic dyes.
  • cyan dyes include aryl or heteryl azo dyes having phenols, naphthols, anilines and the like as coupler components; azomethine dyes having heterocycles such as phenols, naphthols, and pyrrolotriazole as coupler components; cyanine Polymethine dyes such as dyes, oxonol dyes, merocyanine dyes; carbonium dyes such as diphenylmethane dyes, triphenylmethane dyes, xanthene dyes; phthalocyanine dyes; anthraquinone dyes; indigo / thioindigo dyes.
  • each of the above-mentioned dyes may exhibit yellow, magenta, and cyan colors only after a part of the chromophore is dissociated.
  • the counter cation is an alkali metal or an inorganic cation such as ammonium.
  • it may be an organic cation such as pyridinium or quaternary ammonium salt, and may further be a polymer cation having these in a partial structure.
  • the coloring composition of this embodiment can also contain a black dye.
  • black dyes that can be used include disazo, trisazo, and tetraazo dyes.
  • examples of the black coloring compound include a dispersion of carbon black.
  • silicone oil polyalkylsiloxane, polyarylsiloxane, polyalkylarylsiloxane are suitable examples of silicone oil
  • cationic silicone and silicone.
  • silicone resin silicone resin
  • hydrocarbon oil polyolefin, fatty acid ester and the like.
  • the coloring composition of the present embodiment can be blended with other additives as necessary within a range that does not impair the effects of the present invention. Examples of additives in each application will be described later.
  • the coloring composition according to one embodiment of the present invention can be a coloring composition (coloring composition for color filter) used for color filter applications.
  • the coloring composition for color filters contains a polymeric compound.
  • the polymerizable compound include addition polymerizable compounds having at least one ethylenically unsaturated double bond.
  • Specific examples of the polymerizable compound include a compound group having at least one terminal ethylenically unsaturated bond, preferably two or more.
  • Such a group of compounds may be any of chemical forms such as, for example, monomers, polymers, that is, dimers, trimers and oligomers, or mixtures thereof, and (co) polymers thereof.
  • unsaturated carboxylic acid for example, acrylic acid, methacrylic acid
  • its ester body, amide body, these (co) polymer, etc. are mentioned.
  • an addition reaction product of an unsaturated carboxylic acid ester or amide having a nucleophilic substituent such as a hydroxyl group, an amino group, or a mercapto group with a monofunctional or polyfunctional isocyanate or epoxy A dehydration condensation reaction product with a polyfunctional carboxylic acid can also be used.
  • a compound in which an unsaturated phosphonic acid, styrene, vinyl ether, or the like is substituted for the above unsaturated carboxylic acid may be used.
  • the content of the polymerizable compound in the total solid content of the color filter coloring composition is preferably 10 to 80% by mass, more preferably 15 to 75% by mass from the viewpoint of more effectively obtaining the effects of the present invention. More preferably, it is more preferably 20 to 60% by mass.
  • the coloring composition for color filters contains at least 1 type of photoinitiator.
  • the photopolymerization initiator is not particularly limited as long as it can polymerize a polymerizable compound, and is preferably selected from the viewpoints of characteristics, initiation efficiency, absorption wavelength, availability, cost, and the like.
  • Examples of the photopolymerization initiator include at least one active halogen compound selected from halomethyloxadiazole compounds and halomethyl-s-triazine compounds, 3-aryl-substituted coumarin compounds, lophine dimers, benzophenone compounds, acetophenone compounds And derivatives thereof, cyclopentadiene-benzene-iron complex and salts thereof, and oxime compounds.
  • an oxime compound or a biimidazole compound is preferable from the viewpoint of rapid polymerization reaction.
  • the content of the photopolymerization initiator in the total solid content of the color filter coloring composition is preferably 3 to 20% by mass, more preferably 4 to 19% by mass, and 5 to 18% by mass. More preferably it is.
  • the color filter coloring composition preferably contains at least one organic solvent.
  • the organic solvent is basically not limited as long as it can satisfy the solubility of the coexisting core components and the coating property of the coloring composition, and may be selected in consideration of solubility, coating property, and safety. preferable.
  • esters, ethers, ketones, and aromatic hydrocarbons can be used as the organic solvent. These organic solvents may contain only 1 type, and can also mix and use 2 or more types.
  • a mixed solution composed of two or more selected from carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether, and propylene glycol methyl ether acetate is particularly preferable.
  • the content of the organic solvent in the total solid content of the color filter coloring composition is preferably 10 to 80% by mass, and more preferably 15 to 60% by mass.
  • the color filter coloring composition preferably contains at least one alkali-soluble binder.
  • the alkali-soluble binder is not particularly limited except that it has alkali solubility, and can be preferably selected from the viewpoints of heat resistance, developability, availability, and the like.
  • the alkali-soluble bath binder is preferably a linear organic high molecular weight polymer that is soluble in an organic solvent and can be developed with a weak alkaline aqueous solution. Examples of such linear organic high molecular polymers include polymers having a carboxylic acid in the side chain, such as JP-A-59-44615, JP-B-54-34327, JP-B-58-12577, JP-B-54-. No.
  • the alkali-soluble binder may have a polymerizable group in the side chain in order to improve the crosslinking efficiency, and includes, for example, an allyl group, a (meth) acryl group, an allyloxyalkyl group, etc. in the side chain.
  • Polymers and the like are also useful. Examples of the polymer containing a polymerizable group described above include commercially available KS resist-106 (manufactured by Osaka Organic Chemical Industry Co., Ltd.), cyclomer P series (manufactured by Daicel Corporation), and the like.
  • alcohol-soluble nylon polyether of 2,2-bis- (4-hydroxyphenyl) -propane and epichlorohydrin, etc. are also useful.
  • alkali-soluble binders from the viewpoint of heat resistance, polyhydroxystyrene resins, polysiloxane resins, acrylic resins, acrylamide resins, and acrylic / acrylamide copolymer resins are preferable, and from the viewpoint of development control.
  • acrylic resins, acrylamide resins, and acrylic / acrylamide copolymer resins are preferably acrylic resins, acrylamide resins, and acrylic / acrylamide copolymer resins.
  • acrylic resins include copolymers composed of monomers selected from benzyl (meth) acrylate, (meth) acrylic acid, hydroxyethyl (meth) acrylate, (meth) acrylamide, and the like, and commercially available KS resist 106 (Osaka). Organic Chemical Industry Co., Ltd.) and Cyclomer P Series (manufactured by Daicel Corporation) are preferred.
  • the alkali-soluble binder is preferably a polymer having a weight average molecular weight (polystyrene equivalent value measured by GPC method) of 1,000 to 200,000 from the viewpoint of developability, liquid viscosity, etc., and 2,000 to 100,000. More preferred is a polymer of 5,000 to 50,000.
  • the content of the alkali-soluble binder in the total solid content of the color filter coloring composition is preferably 10 to 80% by mass, and more preferably 20 to 60% by mass.
  • the acid value of the alkali-soluble binder is preferably 10 to 1000 mg / KOH, more preferably 50 to 300 mg / KOH, still more preferably 50 to 200 mg / KOH, and particularly preferably 105 to 200 mg / KOH.
  • the coloring composition for color filters may contain only one type of alkali-soluble binder, or may contain two or more types. When two or more types are included, the total amount is preferably within the above range.
  • the color filter coloring composition preferably contains at least one crosslinking agent.
  • the crosslinking agent is not particularly limited as long as it can cure the film by a crosslinking reaction.
  • the crosslinking agent is substituted with at least one substituent selected from an epoxy resin, a methylol group, an alkoxymethyl group, and an acyloxymethyl group.
  • a phenol compound, a naphthol compound or a hydroxyanthracene compound substituted with at least one substituent selected from a melamine compound, a guanamine compound, a glycoluril compound or a urea compound, a methylol group, an alkoxymethyl group, and an acyloxymethyl group .
  • polyfunctional epoxy resins are preferred.
  • the coloring composition for a color filter contains at least one kind of antioxidant.
  • the antioxidant include a radical scavenger, a peroxide decomposer, an ultraviolet absorber, and a singlet oxygen quencher.
  • radical scavengers include phenolic antioxidants and hindered amine antioxidants.
  • phenolic antioxidants include hydroxyphenylpropionate compounds, hydroxybenzyl compounds, thiobisphenol compounds, thiomethylphenol compounds, alkanediylphenol compounds, and the like. Of these, hydroxyphenylpropionate compounds are preferred from the viewpoint of the stability of color characteristics.
  • ultraviolet absorbers examples include salicylate-based antioxidants and benzophenone-based antioxidants.
  • the singlet oxygen quencher examples include ethylenic compounds such as tetramethylethylene and cyclopentene, amines such as diethylamine, triethylamine, 1,4-diazabicyclooctane (DABCO), and N-ethylimidazole.
  • ethylenic compounds such as tetramethylethylene and cyclopentene
  • amines such as diethylamine, triethylamine, 1,4-diazabicyclooctane (DABCO), and N-ethylimidazole.
  • Good condensed polycyclic aromatic compounds such as naphthalene, dimethylnaphthalene, dimethoxyanthracene, anthracene, diphenylanthracene; 1,3-diphenylisobenzofuran, 1,2,3,4-tetraphenyl-1,3-cyclopentadiene, pentaphenyl
  • aromatic compounds such
  • the antioxidants can be used alone or in admixture of two or more.
  • the content of the antioxidant in the total solid content of the color filter coloring composition is preferably 0.01 to 20 parts by mass, particularly preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the colorant. .
  • the colored composition according to one embodiment of the present invention can be a colored composition (colored composition for color toner) used for color toner applications.
  • the content of at least one selected from the alkali metal salts, alkaline earth metal salts and tautomers thereof of the azo dye represented by the general formula (1) in the color toner coloring composition is
  • the coloring composition for toner is 100 parts by mass, it is preferably contained in an amount of 0.1 part by mass or more, more preferably 1 to 20 parts by mass, and further preferably 2 to 10 parts by mass.
  • the color toner coloring composition preferably contains a binder resin.
  • a binder resin all commonly used binders can be used. Examples thereof include styrene resin, acrylic resin, styrene / acrylic resin, and polyester resin.
  • inorganic fine powder and organic fine powder can be externally added for the purpose of fluidity of the composition, charge control and the like.
  • silica fine particles or titania fine particles whose surface is treated with an alkyl group-containing coupling agent or the like are preferable.
  • the number average primary particle diameter of these is preferably 10 to 500 nm, and 0.1 to 20% by mass is preferably added to the toner.
  • the color toner coloring composition preferably contains a release agent.
  • a release agent all conventionally used release agents can be used. Specific examples include olefins such as low molecular weight polypropylene / low molecular weight polyethylene / ethylene-propylene copolymer, microcrystalline wax, carnauba wax, sazol wax, and paraffin wax.
  • the addition amount of the release agent is preferably 1 to 5% by mass based on the total mass of the color toner composition.
  • the color toner coloring composition preferably contains a charge control agent.
  • the charge control agent include those having a quaternary ammonium salt structure and those having a calixarene structure.
  • the coloring composition for color toner can contain a carrier.
  • a carrier either an uncoated carrier constituted only by magnetic material particles such as iron or ferrite, or a resin-coated carrier obtained by coating the surface of the magnetic material particles with a resin or the like may be used.
  • the average particle diameter of the carrier is preferably 30 to 150 ⁇ m in volume average particle diameter.
  • the colored composition according to an embodiment of the present invention can be a colored composition (inkjet recording ink) used for inkjet recording ink applications.
  • the ink for inkjet recording is preferably an ink obtained by dissolving and / or dispersing a coloring composition in an oleophilic medium or an aqueous medium, and more preferably an ink using an aqueous medium. .
  • drying inhibitor for ink jet recording ink, drying inhibitor (wetting agent), anti-fading agent, emulsification stabilizer, penetration enhancer, ultraviolet absorber, preservative, antifungal agent, pH adjuster, surface hearing adjuster as necessary
  • Known additives such as an agent, an antifoaming agent, a viscosity modifier, a dispersant, a dispersion stabilizer, a rust inhibitor, and a chelating agent can be used.
  • these various additives are directly added to the ink liquid in the case of water-soluble ink.
  • an oil-soluble dye is used in the form of a dispersion, it is generally added to the dispersion after the preparation of the dye dispersion, but it may be added to the oil phase or the aqueous phase at the time of preparation.
  • the anti-drying agent is preferably used for the purpose of preventing clogging due to drying of the ink for ink jet recording at the ink ejection port of the nozzle used in the ink jet recording method.
  • a drying inhibitor a water-soluble organic solvent having a vapor pressure lower than that of water is preferable.
  • Specific examples include ethylene glycol, propylene glycol, diethylene glycol, polyethylene glycol, thiodiglycol, dithiodiglycol, 2-methyl-1,3-propanediol, 1,2,6-hexanetriol, acetylene glycol derivatives, glycerin.
  • Polyhydric alcohols typified by trimethylolpropane, etc., lower alkyl ethers of polyhydric alcohols such as ethylene glycol monomethyl (or ethyl) ether, diethylene glycol monomethyl (or ethyl) ether, triethylene glycol monoethyl (or butyl) ether 2-pyrrolidone, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, heterocycles such as N-ethylmorpholine, sulfolane, dimethyl sulfoxide, 3 Sulfur-containing compounds such as sulfolane, diacetone alcohol, polyfunctional compounds such as diethanolamine, and urea derivatives.
  • lower alkyl ethers of polyhydric alcohols such as ethylene glycol monomethyl (or ethyl) ether, diethylene glycol monomethyl (or ethyl) ether, triethylene glycol monoethyl (or butyl) ether
  • drying inhibitor may be used independently and may be used together 2 or more types. These drying inhibitors are preferably contained in the ink for inkjet recording in an amount of 10 to 50% by mass.
  • UV absorbers are used for the purpose of improving image storage stability.
  • examples of the ultraviolet absorber include benzotriazoles described in JP-A Nos. 58-185677, 61-190537, JP-A-2-782, JP-A-5-97075, JP-A-9-34057, and the like.
  • the anti-fading agent is used for the purpose of improving image storage stability.
  • various organic and metal complex antifading agents can be used.
  • Organic anti-fading agents include hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, anilines, amines, indanes, chromans, alkoxyanilines, heterocycles, etc. Complex, zinc complex and the like. More specifically, Research Disclosure No. No. 17643, No. VII, I to J, ibid. 15162, ibid. No. 18716, page 650, left column, ibid. No. 36544, page 527, ibid. No. 307105, page 872, ibid. The compounds described in the patent cited in Japanese Patent No. 15162 and the compounds represented by the general formulas and compound examples of the representative compounds described on pages 127 to 137 of JP-A-62-215272 can be used.
  • antifungal agent examples include sodium dehydroacetate, sodium benzoate, sodium pyridinethione-1-oxide, ethyl p-hydroxybenzoate, 1,2-benzisothiazolin-3-one and salts thereof. These are preferably used in an amount of 0.02 to 1.00% by mass in the ink.
  • a neutralizer organic base, inorganic alkali
  • the pH adjuster is preferably added so that the ink for ink jet recording has a pH of 6 to 10, more preferably 7 to 10.
  • the surface tension adjusting agent examples include nonionic, cationic or anionic surfactants.
  • the surface tension of the ink for ink jet recording of the present invention is preferably 25 to 70 mN / m. Further, 25 to 60 mN / m is preferable. Further, the viscosity of the ink for ink jet recording of the present invention is preferably 30 mPa ⁇ s or less. Furthermore, it is more preferable to adjust to 20 mPa ⁇ s or less.
  • surfactants include fatty acid salts, alkyl sulfate esters, alkyl benzene sulfonates, alkyl naphthalene sulfonates, dialkyl sulfosuccinates, alkyl phosphate ester salts, naphthalene sulfonate formalin condensates, polyoxyethylene alkyl sulfates.
  • Anionic surfactants such as ester salts, polyoxyethylene alkyl ether, polyoxyethylene alkyl allyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkylamine, glycerin fatty acid ester
  • Nonionic surfactants such as oxyethyleneoxypropylene block copolymers are preferred.
  • SURFYNOLS Air Products & Chemicals
  • An amine oxide type amphoteric surfactant such as N, N-dimethyl-N-alkylamine oxide is also preferred.
  • fluorine-based, silicone-based compounds, chelating agents represented by EDTA, and the like can be used as necessary.
  • an alkali metal salt, alkaline earth metal salt of an azo dye or a tautomer thereof, which is a compound according to an embodiment of the present invention is dispersed in an aqueous medium
  • JP-A-11-286637 and JP-A-2001-2001 As described in each publication such as No. 240763, JP-A No. 2001-262039, JP-A No. 2001-247788, etc., colored fine particles containing a compound and an oil-soluble polymer are dispersed in an aqueous medium
  • the specific method for dispersing the compound of the present embodiment in an aqueous medium, the oil-soluble polymer to be used, the high-boiling organic solvent, the additive and the amount used thereof are preferably those described in the above-mentioned patent publications, etc. can do. Or you may disperse
  • Dispersing devices include simple stirrer, impeller stirring method, in-line stirring method, mill method (for example, colloid mill, ball mill, sand mill, attritor, roll mill, agitator mill, etc.), ultrasonic method, high-pressure emulsification dispersion method (high-pressure homogenizer)
  • mill method for example, colloid mill, ball mill, sand mill, attritor, roll mill, agitator mill, etc.
  • ultrasonic method for example, colloid mill, ball mill, sand mill, attritor, roll mill, agitator mill, etc.
  • ultrasonic method for example, colloid mill, ball mill, sand mill, attritor, roll mill, agitator mill, etc.
  • ultrasonic method for example, colloid mill, ball mill, sand mill, attritor, roll mill, agitator mill, etc.
  • ultrasonic method for example, colloid mill, ball mill, sand mill, attritor, roll mill, agitator
  • JP-A-5-148436 JP-A-5-295212, JP-A-7-97541, JP-A-7-82515, JP-A-7- Details are described in Japanese Patent Nos. 118584, 11-286637, and 2001-271003, and can be used for the preparation of an ink for ink jet recording containing a colored composition according to an embodiment of the present invention.
  • a mixture containing water as a main component and optionally adding a water-miscible organic solvent can be used.
  • the water-miscible organic solvent include alcohol (eg, methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol, t-butanol, pentanol, hexanol, cyclohexanol, benzyl alcohol), polyvalent Alcohols (eg, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, hexanediol, pentanediol, glycerin, hexanetriol, thiodiglycol), glycol derivatives (eg , Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene
  • the ink for inkjet recording 0.2 parts of at least one selected from alkali metal salts, alkaline earth metal salts and tautomers thereof of the azo dye represented by the general formula (1) with respect to 100 parts by mass of the ink for inkjet recording.
  • the content is preferably 10 to 10 parts by mass, and more preferably 1 to 6 parts by mass.
  • the ink for ink jet recording may be used in combination with other pigments. When two or more kinds of dyes are used in combination, the total content of the dyes is preferably in the above range.
  • a dyed product can be obtained by applying various dyeing methods to an object to be dyed using the colored composition according to an embodiment of the present invention. Although it does not limit as a dyeing
  • the material to be dyed (the material to be dyed) is not limited as long as it can be dyed such as fiber, cloth, leather, paper, film and the like.
  • Example 1 Synthesis of Exemplified Compound D-115
  • Compound D-200 represented by the following formula, 321 mg, was dissolved in 3.2 mL of isopropyl alcohol. To this solution, 36 mg of lithium hydroxide monohydrate was added and stirred at room temperature for 2 days. The precipitated crystals were collected by filtration and dried to obtain 152 mg (yield 47%) of Exemplary Compound D-115.
  • Example 2 Synthesis of Exemplary Compound D-114
  • Example 3 Synthesis of Exemplary Compound D-113
  • Example 4 Synthesis of Exemplary Compound D-54 A mixture of compound D-201, 255 mg represented by the following formula, potassium tert-butoxide 138 mg, and isopropyl alcohol 2.0 mL was stirred at room temperature for 2 days. The precipitated crystals were collected by filtration and dried to obtain 204 mg (yield 70%) of Exemplary Compound D-54.
  • Example 5 Synthesis of Exemplary Compound D-126 A mixture of Compound D-202 represented by the following formula, 221 mg, potassium acetate 96 mg, and isopropyl alcohol 3.2 mL was stirred at room temperature for 1 day. The precipitated crystals were collected by filtration and dried to obtain 86 mg (yield 34%) of Exemplary Compound D-126.
  • Example 6 Synthesis of Exemplary Compound D-131 After heating a mixture of Compound D-203 represented by the following formula, 304 mg, 124 mg of potassium tert-butoxide, and 3.0 mL of t-amyl alcohol to 50 ° C. And stirred for 18 hours at room temperature. The precipitated crystals were collected by filtration and dried to obtain 196 mg (yield 57%) of Exemplary Compound D-131.
  • Example 7 Preparation of Colored Composition Containing Example Compound D-114 and Measurement of Absorption Spectrum 2.03 mg of the above D-200 was weighed and dissolved in 100 mL of 0.2 mM aqueous sodium hydroxide solution. 4.0 mL of this was taken, and pure water was added to make 10 mL. This prepared a composition containing D-114 at a concentration of 8.56 ppm. Using this composition, the absorption maximum and molar extinction coefficient were measured. The results are shown in Table 1.
  • Example 8 Preparation of colored composition containing exemplary compound D-55 and measurement of absorption spectrum 2.00 mg of the above D-201 was weighed and dissolved in 100 mL of 0.2 mM aqueous sodium hydroxide solution. 4.0 mL of this was taken, and pure water was added to make 10 mL. This prepared a composition containing D-55 at a concentration of 9.19 ppm. Using this composition, the absorption maximum and molar extinction coefficient were measured. The results are shown in Table 1.
  • Example 9 Preparation of Colored Composition Containing Example Compound D-127 and Measurement of Absorption Spectrum 2.02 mg of the above D-202 was weighed and dissolved in 100 mL of 0.2 mM aqueous sodium hydroxide solution. 4.0 mL of this was taken, and pure water was added to make 10 mL. This prepared a composition containing D-127 at a concentration of 9.21 ppm. Using this composition, the absorption maximum and molar extinction coefficient were measured. The results are shown in Table 1.
  • Example 10 Preparation of colored composition containing exemplary compound D-132 and measurement of absorption spectrum 2.00 mg of the above D-203 was weighed and dissolved in 100 mL of 0.2 mM aqueous sodium hydroxide solution. 4.0 mL of this was taken, and pure water was added to make 10 mL. Thus, a composition containing Exemplary Compound D-132 at a concentration of 9.00 ppm was prepared. Using this composition, the absorption maximum and molar extinction coefficient were measured. The results are shown in Table 1.
  • comparative compounds D-200 to D-203 are the above-mentioned compounds D-200 to D-203, respectively.
  • the compounds of Examples 11 to 14 and Comparative Examples 1 to 4 exhibit a high thermal decomposition temperature of 270 ° C. or higher.
  • the thermal decomposition temperature is increased with respect to comparative compounds that are not potassium salts, and the stability to heat is increased.
  • Example 15 Dyeing of inkjet paper by D-114 0.6 g of 10% aqueous solution of Emulgen 109P (manufactured by Kao Corporation) was added to 100 mL of pure water to prepare a surfactant solution. 10.0 g of the above surfactant solution was added and uniformly dissolved in a mixture of 0.100 g of Compound D-200 and 0.5 mL of 1M aqueous sodium hydroxide solution. This obtained the coloring composition containing exemplary compound D-114. This was applied to inkjet paper painting (manufactured by FUJIFILM Corporation) with a bar coater. The reflection spectrum of the dyed product obtained was measured. A bright purple dyeing was obtained.
  • Example 16 Dyeing of inkjet paper with D-55 0.6 g of 10% aqueous solution of Emulgen 109P (manufactured by Kao Corporation) was added to 100 mL of pure water to prepare a surfactant solution. 10.0 g of the above surfactant solution was added and uniformly dissolved in a mixture of 0.111 g of Compound D-201 and 0.5 mL of 1M aqueous sodium hydroxide solution. As a result, a colored composition containing Exemplified Compound D-55 was obtained, and this was applied to an inkjet paper image (Fuji Film Co., Ltd.) with a bar coater. The reflection spectrum of the dyed product obtained was measured. A bright red dyeing was obtained.
  • Emulgen 109P manufactured by Kao Corporation
  • Example 17 Dyeing of inkjet paper with D-132 0.6 g of 10% aqueous solution of Emulgen 109P (manufactured by Kao Corporation) was added to 100 mL of pure water to prepare a surfactant solution. 10.0 g of the above surfactant solution was added and uniformly dissolved in a mixture of 0.093 g of Compound D-203 and 0.5 mL of 1M aqueous sodium hydroxide solution. This obtained the coloring composition containing exemplary compound D-132. This was applied to inkjet paper painting (manufactured by FUJIFILM Corporation) with a bar coater. The reflection spectrum of the dyed product obtained was measured. A bright yellow dyeing was obtained.
  • the reflection spectra of the dyed products obtained in Examples 15 to 17 are shown in FIGS.
  • the L *, a *, and b * values are shown in Table 3.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention concerne un sel métallique alcalin de colorant azoïque représenté par la formule générale (1), un sel métallique alcalino-terreux ainsi qu'un tautomère de ce sel métallique alcalino-terreux, une composition colorante mettant en œuvre ce tautomère, un procédé de teinture et un produit teinté. A-N=N-B (1)
PCT/JP2015/078536 2014-10-27 2015-10-07 Sel métallique alcalin de colorant azoïque, sel métallique alcalino-terreux ainsi que tautomère de celui-ci, composition colorante, procédé de teinture et produit teinté WO2016067865A1 (fr)

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JP2014-218244 2014-10-27
JP2014218244A JP2016084421A (ja) 2014-10-27 2014-10-27 アゾ色素のアルカリ金属塩、アルカリ土類金属塩及びその互変異性体、着色組成物、染色方法及び染色物

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57159499A (en) * 1981-03-26 1982-10-01 Fuji Photo Film Co Ltd Substrate for determining alkaline phosphatase and determining method
JP2005162752A (ja) * 2003-11-28 2005-06-23 Kao Corp 染色毛の可逆的変色方法
JP2007326818A (ja) * 2006-06-08 2007-12-20 Kao Corp 染毛剤組成物
JP2009013072A (ja) * 2007-06-29 2009-01-22 Kao Corp 染毛剤組成物
JP2009013070A (ja) * 2007-06-29 2009-01-22 Kao Corp 染毛剤組成物
WO2013047386A1 (fr) * 2011-09-30 2013-04-04 富士フイルム株式会社 Composition colorante aqueuse pour l'impression de textile, procédé d'impression de textile et tissu

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Publication number Priority date Publication date Assignee Title
JPH08282133A (ja) * 1995-04-10 1996-10-29 Fuji Photo Film Co Ltd 熱転写記録材料
JP2000284440A (ja) * 1999-03-31 2000-10-13 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
JP4174143B2 (ja) * 1999-09-17 2008-10-29 富士フイルム株式会社 フェノールアゾ色素およびそれを含有するハロゲン化銀カラー感光材料
JP2002322383A (ja) * 2001-04-26 2002-11-08 Sumitomo Chem Co Ltd モノアゾ化合物又はその塩、及びそれらの繊維材料への適用
EP1366752A1 (fr) * 2002-05-28 2003-12-03 Kao Corporation Composition pour la coloration des cheveux
JP5317561B2 (ja) * 2008-07-16 2013-10-16 花王株式会社 染毛剤組成物

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57159499A (en) * 1981-03-26 1982-10-01 Fuji Photo Film Co Ltd Substrate for determining alkaline phosphatase and determining method
JP2005162752A (ja) * 2003-11-28 2005-06-23 Kao Corp 染色毛の可逆的変色方法
JP2007326818A (ja) * 2006-06-08 2007-12-20 Kao Corp 染毛剤組成物
JP2009013072A (ja) * 2007-06-29 2009-01-22 Kao Corp 染毛剤組成物
JP2009013070A (ja) * 2007-06-29 2009-01-22 Kao Corp 染毛剤組成物
WO2013047386A1 (fr) * 2011-09-30 2013-04-04 富士フイルム株式会社 Composition colorante aqueuse pour l'impression de textile, procédé d'impression de textile et tissu

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Title
H. IBRAHIM UGRAS ET AL.: "Synthesis and Extraction Studies of Some New Anionic Dye Extractors, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry", vol. 38, no. 4, 2008, pages 376 - 381, XP055277709 *

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