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WO2017110387A1 - Composition colorante, encre pour jet d'encre, procédé d'impression sur tissu, et composé - Google Patents

Composition colorante, encre pour jet d'encre, procédé d'impression sur tissu, et composé Download PDF

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Publication number
WO2017110387A1
WO2017110387A1 PCT/JP2016/085446 JP2016085446W WO2017110387A1 WO 2017110387 A1 WO2017110387 A1 WO 2017110387A1 JP 2016085446 W JP2016085446 W JP 2016085446W WO 2017110387 A1 WO2017110387 A1 WO 2017110387A1
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group
general formula
integer
compound represented
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English (en)
Japanese (ja)
Inventor
一成 八木
彰宏 原
立石　桂一
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Fujifilm Corp
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Fujifilm Corp
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Priority to JP2017557821A priority Critical patent/JPWO2017110387A1/ja
Publication of WO2017110387A1 publication Critical patent/WO2017110387A1/fr
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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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C09B11/20—Preparation from other triarylmethane derivatives, e.g. by substitution, by replacement of substituents
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C09B11/14—Preparation from aromatic aldehydes, aromatic carboxylic acids or derivatives thereof and aromatic amines
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C09B11/16—Preparation from diarylketones or diarylcarbinols, e.g. benzhydrol
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/54—Inks based on two liquids, one liquid being the ink, the other liquid being a reaction solution, a fixer or a treatment solution for the ink
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/241—Polyamides; Polyurethanes using acid 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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/30—Ink jet printing
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06C—FINISHING, DRESSING, TENTERING OR STRETCHING TEXTILE FABRICS
    • D06C23/00—Making patterns or designs on fabrics
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/14—Wool
    • D06P3/16—Wool using acid 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/248—Polyamides; Polyurethanes using reactive 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/66—Natural or regenerated cellulose using reactive dyes

Definitions

  • the present invention relates to a coloring composition, an inkjet ink, a printing method, and a compound.
  • a technique for dyeing a fabric using a triarylmethane dye has been studied conventionally.
  • dyeing polyamide such as silk or nylon Acid Blue 7 (AB7) and Acid Blue 9 (AB9) have been used.
  • screen printing, roller printing, transfer printing, and the like have been performed as industrial dyeing methods for dyeing fabrics.
  • These methods are dyeing techniques that are completed only after a series of processes such as design pattern planning, engraving or plate making, creation of printing paste, and preparation of fabrics are integrated.
  • ink jet textile printing using an ink jet method capable of directly supplying a dye to a cloth has been proposed.
  • inkjet textile printing has the advantage that it is not necessary to prepare a plate and can quickly form an image with excellent gradation.
  • Patent Document 1 describes a triarylmethane compound having a heterocycle bonded to a metal atom. Using a coloring composition containing this compound, printing is performed on paper by an inkjet method, and the hue is determined. The light resistance has been studied.
  • An object of the present invention is to provide a coloring composition having excellent cyan optical density and excellent light resistance. Another object of the present invention is to provide an ink-jet ink and a textile printing method containing the above colored composition. Another object of the present invention is to provide a compound having excellent cyan optical density and light resistance.
  • R 101 and R 103 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R 102 and R 104 each independently represents an alkyl group, an aryl group, or a heterocyclic group.
  • R 105 and R 106 are each independently a halogen atom, alkyl group, cyano group, nitro group, alkoxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino Represents a group, sulfamoylamino group, alkylsulfonylamino group, alkylthio group, sulfamoyl group, alkylsulfinyl group, alkylsulfonyl group, acyl group, alkoxycarbonyl group, carbamoyl group, imide group or sulfo group.
  • R 107 , R 108 , R 109 , R 110 and R 111 each independently represent a substituent
  • X 101 , X 102 and X 103 each independently represent CH or a nitrogen atom.
  • at least one of X 101 to X 103 represents CH.
  • X 101 to X 103 represent CH
  • a hydrogen atom may be removed and R 109 may be bonded.
  • n 101 and n 102 each independently represents an integer of 0 to 3
  • n 103 represents an integer of 0 to 5
  • n 104 and n 105 each independently represents an integer of 0 or more.
  • n 101 , n 102 , n 103 , n 104 and n 105 each represent an integer of 2 or more, a plurality of R 107 , R 108 , R 109 , R 110 and R 111 are the same or different. Also good.
  • Ar 101 and Ar 102 each independently represent a benzene ring, a naphthalene ring, or an aromatic heterocycle.
  • the compound represented by the general formula (1) has at least two ionic hydrophilic groups.
  • the compound represented by the general formula (1) has a counter anion in the molecule.
  • R 201 and R 203 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R 202 and R 204 each independently represents an alkyl group, an aryl group, or a heterocyclic group.
  • R 221 , R 222 , R 223 and R 224 are each independently a halogen atom, alkyl group, cyano group, nitro group, alkoxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, amino group, acylamino group, aminocarbonyl Amino group, alkoxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, alkylthio group, sulfamoyl group, alkylsulfinyl group, alkylsulfonyl group, acyl group, alkoxycarbonyl group, carbamoyl group, imide group or sulfo group .
  • R 207 , R 208 , R 209 , R 210 and R 211 each independently represent a substituent
  • X 201 , X 202 and X 203 each independently represent CH or a nitrogen atom.
  • at least one of X 201 to X 203 represents CH.
  • X 201 to X 203 represent CH
  • a hydrogen atom may be removed and R 209 may be bonded.
  • n 201 and n 202 each independently represents an integer of 0 to 3
  • n 203 represents an integer of 0 to 5
  • n 204 and n 205 each independently represents an integer of 0 or more.
  • n 201 , n 202 , n 203 , n 204, and n 205 each represent an integer of 2 or more, a plurality of R 207 , R 208 , R 209 , R 210, and R 211 are the same or different. Also good.
  • Ar 201 and Ar 202 each independently represent a benzene ring, a naphthalene ring, or an aromatic heterocycle.
  • the compound represented by the general formula (2) has at least two ionic hydrophilic groups.
  • the compound represented by the general formula (2) has a counter anion in the molecule. ⁇ 3>
  • R 301 and R 303 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R 302 and R 304 each independently represents an alkyl group, an aryl group, or a heterocyclic group.
  • R 321 , R 322 , R 323 and R 324 are each independently a halogen atom, alkyl group, cyano group, nitro group, alkoxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, amino group, acylamino group, aminocarbonyl Amino group, alkoxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, alkylthio group, sulfamoyl group, alkylsulfinyl group, alkylsulfonyl group, acyl group, alkoxycarbonyl group, carbamoyl group, imide group or sulfo group .
  • R 307 , R 308 , R 309 , R 310 and R 311 each independently represent a substituent
  • X 301 , X 302 and X 303 each independently represent CH or a nitrogen atom.
  • at least one of X 301 to X 303 represents CH.
  • X 301 to X 303 represent CH
  • a hydrogen atom may be removed and R 309 may be bonded.
  • n 301 and n 302 each independently represents an integer of 0 to 3
  • n 303 represents an integer of 0 to 5
  • n 304 and n 305 each independently represents an integer of 0 to 3.
  • n 301 , n 302 , n 303 , n 304, and n 305 each represent an integer of 2 or more, a plurality of R 307 , R 308 , R 309 , R 310, and R 311 are the same or different. Also good.
  • the compound represented by the general formula (3) has at least two ionic hydrophilic groups.
  • the compound represented by the general formula (3) has a counter anion in the molecule. ⁇ 4> ⁇ 1> to ⁇ 3>, wherein the compound represented by the general formula (1), (2) or (3) is a compound represented by the following general formula (4): Coloring composition.
  • R 401 and R 403 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R 402 and R 404 each independently represents an alkyl group, an aryl group, or a heterocyclic group.
  • R 421 , R 422 , R 423 and R 424 are each independently a halogen atom, alkyl group, cyano group, nitro group, alkoxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, amino group, acylamino group, aminocarbonyl Amino group, alkoxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, alkylthio group, sulfamoyl group, alkylsulfinyl group, alkylsulfonyl group, acyl group, alkoxycarbonyl group, carbamoyl group, imide group or sulfo group .
  • R 407 , R 408 , R 409 , R 410 and R 411 each independently represent a substituent.
  • n 401 and n 402 each independently represents an integer of 0 to 3
  • n 403 represents an integer of 0 to 4
  • n 404 and n 405 each independently represents an integer of 0 to 3.
  • n 401 , n 402 , n 403 , n 404, and n 405 each represent an integer of 2 or more
  • a plurality of R 407 , R 408 , R 409 , R 410, and R 411 are the same or different. Also good.
  • the compound represented by the general formula (4) has at least two ionic hydrophilic groups.
  • R 501 and R 502 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R 521 , R 522 , R 523 , R 524 , R 531 and R 532 are each independently a halogen atom, alkyl group, cyano group, nitro group, alkoxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, amino group , Acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, alkylthio group, sulfamoyl group, alkylsulfinyl group, alkylsulfonyl group, acyl group, alkoxycarbonyl group, carbamoyl group, imide Represents a group or a sulfo group.
  • R 507 , R 508 , R 509 , R 510 , R 511 , R 512 and R 513 each independently represent a substituent.
  • n 501 and n 502 each independently represents an integer of 0 to 3
  • n 503 represents an integer of 0 to 4
  • n 504 and n 505 each independently represents an integer of 0 to 3
  • n 506 and n 507 Each independently represents an integer of 0 or more.
  • n 501 , n 502 , n 503 , n 504 , n 505 , n 506, and n 507 each represent an integer of 2 or more
  • a plurality of R 507 , R 508 , R 509 , R 510 , R 511 , R 512 And R 513 may be the same or different.
  • Ar 501 and Ar 502 each independently represent a benzene ring, a naphthalene ring, or an aromatic heterocycle.
  • the compound represented by the general formula (5) has at least two ionic hydrophilic groups. ⁇ 6> ⁇ 1> to ⁇ 5>, wherein the compound represented by the general formula (1), (2), (3), (4) or (5) is a compound represented by the following general formula (6): The coloring composition of any one of these.
  • R601 and R602 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R 621 , R 622 , R 623 , R 624 , R 631 , R 632 , R 633 and R 634 are each independently a halogen atom, alkyl group, cyano group, nitro group, alkoxy group, acyloxy group, carbamoyloxy group, alkoxy Carbonyloxy, amino, acylamino, aminocarbonylamino, alkoxycarbonylamino, sulfamoylamino, alkylsulfonylamino, alkylthio, sulfamoyl, alkylsulfinyl, alkylsulfonyl, acyl, alkoxycarbonyl Represents a group, a carbamoyl group, an imide group or a sulfo group.
  • R 607 , R 608 , R 609 , R 610 , R 611 , R 612 and R 613 each independently represent a substituent.
  • n 601 and n 602 each independently represents an integer of 0 to 3
  • n 603 represents an integer of 0 to 4
  • n 604 and n 605 each independently represents an integer of 0 to 3
  • n 606 and n 607 Each independently represents an integer of 0 to 3.
  • n 601 , n 602 , n 603 , n 604 , n 605 , n 606, and n 607 each represent an integer of 2 or more
  • a plurality of R 607 , R 608 , R 609 , R 610 , R 611 , R 612 And R 613 may be the same or different.
  • the compound represented by the general formula (6) has at least two ionic hydrophilic groups.
  • a printing method comprising the following steps (1) to (4).
  • (1) A step of adding a colored composition as described in ⁇ 7> to a liquid containing at least a polymer compound and water to prepare a colored paste.
  • (2) Printing the colored paste of (1) on a fabric.
  • Step (3) Step of applying steam to the printed fabric (4) Step of washing the printed fabric with water and drying the washed fabric ⁇ 10>
  • a printing method comprising the following steps (11) to (14).
  • (11) A step of applying a paste containing at least a polymer compound and water to the fabric.
  • (12) A step of printing the ink-jet ink according to ⁇ 8> on the fabric by an ink-jet method.
  • (13) Vapor is applied to the printed fabric.
  • (14) Washing the printed fabric with water and drying the washed fabric ⁇ 11>
  • ⁇ 12> A compound represented by the following general
  • R 101 and R 103 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R 102 and R 104 each independently represents an alkyl group, an aryl group, or a heterocyclic group.
  • R 105 and R 106 are each independently a halogen atom, alkyl group, cyano group, nitro group, alkoxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino Represents a group, sulfamoylamino group, alkylsulfonylamino group, alkylthio group, sulfamoyl group, alkylsulfinyl group, alkylsulfonyl group, acyl group, alkoxycarbonyl group, carbamoyl group, imide group or sulfo group.
  • R 107 , R 108 , R 109 , R 110 and R 111 each independently represent a substituent
  • X 101 , X 102 and X 103 each independently represent CH or a nitrogen atom.
  • at least one of X 101 to X 103 represents CH.
  • X 101 to X 103 represent CH
  • a hydrogen atom may be removed and R 109 may be bonded.
  • n 101 and n 102 each independently represents an integer of 0 to 3
  • n 103 represents an integer of 0 to 5
  • n 104 and n 105 each independently represents an integer of 0 or more.
  • n 101 , n 102 , n 103 , n 104 and n 105 each represent an integer of 2 or more, a plurality of R 107 , R 108 , R 109 , R 110 and R 111 are the same or different. Also good.
  • Ar 101 and Ar 102 each independently represent a benzene ring, a naphthalene ring, or an aromatic heterocycle.
  • the compound represented by the general formula (1) has at least two ionic hydrophilic groups.
  • the compound represented by the general formula (1) has a counter anion in the molecule.
  • a colored composition having excellent cyan optical density and excellent light resistance can be provided.
  • the inkjet ink containing the said coloring composition and the textile printing method can be provided.
  • a compound having excellent cyan optical density and light resistance can be provided.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • alkyl group examples include linear, branched, and cyclic substituted or unsubstituted alkyl groups, and include cycloalkyl groups, bicycloalkyl groups, and tricyclo structures having many ring structures.
  • An alkyl group (for example, an alkyl group of an alkoxy group or an alkylthio group) in a substituent described below also represents such an alkyl group.
  • an alkyl group having 1 to 30 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group, an n-octyl group, an eicosyl group, 2- Examples thereof include a chloroethyl group, a 2-cyanoethyl group, a 2-ethylhexyl group, etc.
  • the cycloalkyl group is preferably a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, such as a cyclohexyl group, a cyclopentyl group, 4 -N-dodecylcyclohexyl group and the like
  • the bicycloalkyl group is preferably a substituted or unsubstituted bicycloalkyl group having 5 to 30 carbon atoms, that is, one hydrogen atom from a bicycloalkane having 5 to 30 carbon atoms.
  • Monovalent groups removed for example, bicyclo [1,2,2] heptan-2-yl group, bicyclo [2,2 2] octan-3-yl group.
  • aralkyl group examples include a substituted or unsubstituted aralkyl group, and the substituted or unsubstituted aralkyl group is preferably an aralkyl group having 7 to 30 carbon atoms. Examples thereof include a benzyl group and a 2-phenethyl group.
  • alkenyl group examples include linear, branched, and cyclic substituted or unsubstituted alkenyl groups, and include cycloalkenyl groups and bicycloalkenyl groups.
  • Preferred examples of the alkenyl group include substituted or unsubstituted alkenyl groups having 2 to 30 carbon atoms such as vinyl group, allyl group, prenyl group, geranyl group, and oleyl group.
  • cycloalkenyl group examples include Is a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom of a cycloalkene having 3 to 30 carbon atoms, such as a 2-cyclopenten-1-yl group, 2-cyclohexen-1-yl group and the like.
  • bicycloalkenyl group a substituted or unsubstituted bicycloalkenyl group, preferably a substituted or unsubstituted bicycloalkenyl group having 5 to 30 carbon atoms, that is, a double bond
  • the alkynyl group is preferably a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, such as an ethynyl group, a propargyl group, a trimethylsilylethynyl group, and the like.
  • the aryl group is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a p-tolyl group, a naphthyl group, an m-chlorophenyl group, an o-hexadecanoylaminophenyl group, and the like. Can be mentioned.
  • the heterocyclic group is preferably a monovalent group obtained by removing one hydrogen atom from a 5- or 6-membered substituted or unsubstituted aromatic or non-aromatic heterocyclic compound, and more preferably a carbon number.
  • Examples thereof include 3 to 30 5- or 6-membered aromatic heterocyclic groups such as a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, and a 2-benzothiazolyl group.
  • non-aromatic heterocyclic groups include morpholinyl groups.
  • the alkoxy group is preferably a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, such as a methoxy group, an ethoxy group, an isopropoxy group, a t-butoxy group, an n-octyloxy group, or a 2-methoxyethoxy group. Etc.
  • the aryloxy group is preferably a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, such as a phenoxy group, 2-methylphenoxy group, 4-t-butylphenoxy group, 3-nitrophenoxy group, 2 -Tetradecanoylaminophenoxy group and the like.
  • silyloxy group examples include substituted or unsubstituted silyloxy groups having 0 to 20 carbon atoms, such as trimethylsilyloxy group and diphenylmethylsilyloxy group.
  • the heterocyclic oxy group is preferably a substituted or unsubstituted heterocyclic oxy group having 2 to 30 carbon atoms, such as a 1-phenyltetrazol-5-oxy group and a 2-tetrahydropyranyloxy group.
  • the acyloxy group is preferably a formyloxy group, a substituted or unsubstituted alkylcarbonyloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyloxy group having 6 to 30 carbon atoms, such as an acetyloxy group, Examples include pivaloyloxy group, stearoyloxy group, benzoyloxy group, p-methoxyphenylcarbonyloxy group and the like.
  • the carbamoyloxy group is preferably a substituted or unsubstituted carbamoyloxy group having 1 to 30 carbon atoms, such as N, N-dimethylcarbamoyloxy group, N, N-diethylcarbamoyloxy group, morpholinocarbonyloxy group, N , N-di-n-octylaminocarbonyloxy group, Nn-octylcarbamoyloxy group and the like.
  • the alkoxycarbonyloxy group is preferably a substituted or unsubstituted alkoxycarbonyloxy group having 2 to 30 carbon atoms, such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a t-butoxycarbonyloxy group, or an n-octylcarbonyloxy group. Etc.
  • aryloxycarbonyloxy group a substituted or unsubstituted aryloxycarbonyloxy group having 7 to 30 carbon atoms such as phenoxycarbonyloxy group, p-methoxyphenoxycarbonyloxy group, pn-hexadecyloxy is preferable. Examples include phenoxycarbonyloxy group.
  • the amino group includes an alkylamino group, an arylamino group, and a heterocyclic amino group, preferably an amino group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 6 to 30 carbon atoms.
  • the substituted anilino group include a methylamino group, a dimethylamino group, an anilino group, an N-methyl-anilino group, a diphenylamino group, and a triazinylamino group.
  • the acylamino group is preferably a formylamino group, a substituted or unsubstituted alkylcarbonylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylcarbonylamino group having 6 to 30 carbon atoms, such as an acetylamino group, Examples include pivaloylamino group, lauroylamino group, benzoylamino group, 3,4,5-tri-n-octyloxyphenylcarbonylamino group, and the like.
  • the aminocarbonylamino group is preferably a substituted or unsubstituted aminocarbonylamino group having 1 to 30 carbon atoms, such as a carbamoylamino group, N, N-dimethylaminocarbonylamino group, N, N-diethylaminocarbonylamino group. And a morpholinocarbonylamino group.
  • the alkoxycarbonylamino group is preferably a substituted or unsubstituted alkoxycarbonylamino group having 2 to 30 carbon atoms, such as a methoxycarbonylamino group, an ethoxycarbonylamino group, a t-butoxycarbonylamino group, or an n-octadecyloxycarbonylamino group. Group, N-methyl-methoxycarbonylamino group and the like.
  • the aryloxycarbonylamino group is preferably a substituted or unsubstituted aryloxycarbonylamino group having 7 to 30 carbon atoms, such as phenoxycarbonylamino group, p-chlorophenoxycarbonylamino group, mn-octyloxyphenoxy. Examples thereof include a carbonylamino group.
  • the sulfamoylamino group is preferably a substituted or unsubstituted sulfamoylamino group having 0 to 30 carbon atoms, such as a sulfamoylamino group, N, N-dimethylaminosulfonylamino group, Nn- Examples include octylaminosulfonylamino group.
  • the alkyl or arylsulfonylamino group is preferably a substituted or unsubstituted alkylsulfonylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfonylamino group having 6 to 30 carbon atoms, such as a methylsulfonylamino group.
  • the alkylthio group is preferably a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, such as a methylthio group, an ethylthio group, and an n-hexadecylthio group.
  • the arylthio group is preferably a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, such as a phenylthio group, a p-chlorophenylthio group, and an m-methoxyphenylthio group.
  • heterocyclic thio group examples include substituted or unsubstituted heterocyclic thio groups having 2 to 30 carbon atoms, such as 2-benzothiazolylthio group and 1-phenyltetrazol-5-ylthio group.
  • the sulfamoyl group is preferably a substituted or unsubstituted sulfamoyl group having 0 to 30 carbon atoms, such as N-ethylsulfamoyl group, N- (3-dodecyloxypropyl) sulfamoyl group, N, N-dimethylsulfuryl group.
  • Examples include a famoyl group, an N-acetylsulfamoyl group, an N-benzoylsulfamoyl group, and an N- (N′-phenylcarbamoyl) sulfamoyl group.
  • the alkyl or arylsulfinyl group is preferably a substituted or unsubstituted alkylsulfinyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfinyl group having 6 to 30 carbon atoms, such as a methylsulfinyl group or an ethylsulfinyl group. , Phenylsulfinyl group, p-methylphenylsulfinyl group and the like.
  • the alkyl or arylsulfonyl group is preferably a substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfonyl group having 6 to 30 carbon atoms, such as a methylsulfonyl group or an ethylsulfonyl group. , Phenylsulfonyl group, p-methylphenylsulfonyl group and the like.
  • the acyl group is preferably a formyl group, a substituted or unsubstituted alkylcarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyl group having 7 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms.
  • Heterocyclic carbonyl groups bonded to carbonyl groups at substituted carbon atoms eg, acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl, pn-octyloxyphenylcarbonyl, 2-pyridyl
  • Examples thereof include a carbonyl group and a 2-furylcarbonyl group.
  • the aryloxycarbonyl group is preferably a substituted or unsubstituted aryloxycarbonyl group having 7 to 30 carbon atoms, such as a phenoxycarbonyl group, an o-chlorophenoxycarbonyl group, an m-nitrophenoxycarbonyl group, pt- A butylphenoxycarbonyl group etc. are mentioned.
  • the alkoxycarbonyl group is preferably a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group, and an n-octadecyloxycarbonyl group.
  • the carbamoyl group is preferably a substituted or unsubstituted carbamoyl group having 1 to 30 carbon atoms, such as a carbamoyl group, an N-methylcarbamoyl group, an N, N-dimethylcarbamoyl group, or an N, N-di-n-octyl group.
  • a carbamoyl group, an N- (methylsulfonyl) carbamoyl group, and the like can be given.
  • the aryl or heterocyclic azo group is preferably a substituted or unsubstituted arylazo group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic azo group having 3 to 30 carbon atoms, such as a phenylazo group, p-chlorophenylazo Group, 5-ethylthio-1,3,4-thiadiazol-2-ylazo group and the like.
  • Preferred examples of the imide group include an N-succinimide group and an N-phthalimide group.
  • the phosphino group is preferably a substituted or unsubstituted phosphino group having 0 to 30 carbon atoms, such as a dimethylphosphino group, a diphenylphosphino group, a methylphenoxyphosphino group, and the like.
  • the phosphinyl group is preferably a substituted or unsubstituted phosphinyl group having 0 to 30 carbon atoms, such as a phosphinyl group, a dioctyloxyphosphinyl group, a diethoxyphosphinyl group, and the like.
  • the phosphinyloxy group is preferably a substituted or unsubstituted phosphinyloxy group having 0 to 30 carbon atoms, such as a diphenoxyphosphinyloxy group and a dioctyloxyphosphinyloxy group.
  • the phosphinylamino group is preferably a substituted or unsubstituted phosphinylamino group having 0 to 30 carbon atoms, such as a dimethoxyphosphinylamino group or a dimethylaminophosphinylamino group.
  • silyl group examples include substituted or unsubstituted silyl groups having 0 to 30 carbon atoms, such as a trimethylsilyl group, a t-butyldimethylsilyl group, and a phenyldimethylsilyl group.
  • the ionic hydrophilic group examples include a sulfo group, a carboxyl group, a thiocarboxyl group, a sulfino group, a phosphono group, a dihydroxyphosphino group, and a quaternary ammonium group. Particularly preferred are a sulfo group and a carboxyl group.
  • the ionic hydrophilic group may be in a state containing a cation or an anion (also referred to as “salt state”).
  • the carboxyl group, the phosphono group, and the sulfo group may be in a state containing a cation.
  • Examples of the cation that forms a salt state include ammonium ion, alkali metal ion (eg, lithium ion, sodium ion, potassium ion). Ion) and organic cations (eg, tetramethylammonium ion, tetramethylguanidinium ion, tetramethylphosphonium), lithium ion, sodium ion, potassium ion, and ammonium ion are preferable, and lithium ion or sodium ion is more preferable. .
  • alkali metal ion eg, lithium ion, sodium ion, potassium ion
  • organic cations eg, tetramethylammonium ion, tetramethylguanidinium ion, tetramethylphosphonium
  • lithium ion, sodium ion, potassium ion, and ammonium ion are preferable, and lithium ion or sodium ion is more preferable.
  • the salt when the compound is a salt, the salt is dissociated into ions in the water-soluble ink.
  • the coloring composition of this invention is a coloring composition containing the compound represented by General formula (1).
  • the coloring composition of the present invention is used as a coloring composition for textile printing, a fabric dyed in cyan can be obtained. Improvement in light resistance was observed in the colored portion of the dyed fabric. Although the mechanism of action is unknown, the compound represented by the general formula (1) improves the light resistance because it shields the site that is easily photodegraded. Further, R 105 and R 106 in the general formula (1) It is considered that the hue has become cyan because it has a specific substituent.
  • R 101 and R 103 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R 102 and R 104 each independently represents an alkyl group, an aryl group, or a heterocyclic group.
  • R 105 and R 106 are each independently a halogen atom, alkyl group, cyano group, nitro group, alkoxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino Represents a group, sulfamoylamino group, alkylsulfonylamino group, alkylthio group, sulfamoyl group, alkylsulfinyl group, alkylsulfonyl group, acyl group, alkoxycarbonyl group, carbamoyl group, imide group or sulfo group.
  • R 107 , R 108 , R 109 , R 110 and R 111 each independently represent a substituent
  • X 101 , X 102 and X 103 each independently represent CH or a nitrogen atom.
  • at least one of X 101 to X 103 represents CH.
  • X 101 to X 103 represent CH
  • a hydrogen atom may be removed and R 109 may be bonded.
  • n 101 and n 102 each independently represents an integer of 0 to 3
  • n 103 represents an integer of 0 to 5
  • n 104 and n 105 each independently represents an integer of 0 or more.
  • n 101 , n 102 , n 103 , n 104 and n 105 each represent an integer of 2 or more, a plurality of R 107 , R 108 , R 109 , R 110 and R 111 are the same or different. Also good.
  • Ar 101 and Ar 102 each independently represent a benzene ring, a naphthalene ring, or an aromatic heterocycle.
  • the compound represented by the general formula (1) has at least two ionic hydrophilic groups.
  • the compound represented by the general formula (1) has a counter anion in the molecule.
  • R 101 , R 102 , R 103 and R 104 in the general formula (1) represent an alkyl group, an aryl group or a heterocyclic group, these may have a substituent.
  • R 105 and R 106 are alkyl groups, alkoxy groups, acyloxy groups, carbamoyloxy groups, alkoxycarbonyloxy groups, amino groups, acylamino groups, aminocarbonylamino groups, alkoxycarbonylamino groups, sulfamoylamino groups, alkylsulfonylamino groups.
  • substituents in the case where each group has a substituent include a substituent selected from the above substituent group A.
  • R 101 and R 103 are preferably a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent.
  • R 102 and R 104 are preferably an alkyl group which may have a substituent, or an aryl group which may have a substituent, and has an alkyl group having a substituent or a substituent.
  • An aryl group which may be substituted is more preferable, and an alkyl group having a substituent or an aryl group having a substituent is more preferable.
  • the alkyl group for R 101 , R 102 , R 103 and R 104 is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and still more preferably a methyl group or an ethyl group.
  • R 102 and R 104 are alkyl groups, a methyl group substituted with a phenyl group is most preferred.
  • the methyl group substituted with the phenyl group may further have a substituent.
  • the aryl group for R 101 , R 102 , R 103 and R 104 is preferably a phenyl group or a naphthyl group, and more preferably a phenyl group. If R 102 and R 104 represents an alkyl group or an aryl group, R 101 and R 103 preferably represents a hydrogen atom.
  • R 105 and R 106 preferably have a halogen atom, a cyano group, a nitro group, an amino group, an optionally substituted carbamoyl group, an optionally substituted alkyl group, or a substituent.
  • R 105 and R 106 are more preferably an alkyl group which may have a substituent, or a halogen atom (a chlorine atom is particularly preferable as a halogen atom), and may have a substituent. More preferred is an alkyl group.
  • the alkyl group preferably has 1 to 6 carbon atoms, and more preferably 1 to 4 carbon atoms.
  • the alkyl group is preferably a non-substituted group (unsubstituted alkyl group).
  • Examples of the substituent represented by R 107 , R 108 , R 109 , R 110 , and R 111 include a substituent selected from the above substituent group A, preferably an alkyl group, a sulfo group, a cyano group, a nitro group, A sulfamoyl group which may have a substituent, a halogen atom, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, a heterocyclic oxy group which may have a substituent, An acyloxy group which may have a substituent, an alkylamino group which may have a substituent, an arylamino group which may have a substituent, a heterocyclic amino group which may have a substituent, a substituent An acylamino group which may have a substituent, an aminocarbonylamino group which may have a substituent, an alkoxycarbonylamino group which may have a substituent
  • n 101 and n 102 preferably represent an integer of 0 to 2.
  • n 103 preferably represents an integer of 0 to 3, more preferably 0 or 1.
  • n 104 and R 105 preferably represent an integer of 0 to 5.
  • X 101 , X 102 and X 103 each independently represent CH or a nitrogen atom, and preferably represents CH.
  • X 101 , X 102 and X 103 represent CH, a hydrogen atom may be removed and a substituent R 109 may be bonded.
  • Ar 101 and Ar 102 each independently represent a benzene ring, a naphthalene ring, or an aromatic heterocycle.
  • the aromatic heterocycle is preferably a 5-membered ring or a 6-membered ring, preferably a nitrogen-containing aromatic heterocycle, specifically a pyridine ring or a pyrimidine ring.
  • Ar 101 and Ar 102 represent a benzene ring.
  • the compound represented by the general formula (1) has at least two ionic hydrophilic groups.
  • the compound represented by the general formula (1) preferably has at least two ionic hydrophilic groups from the viewpoint of ink storage stability and dyeability to fibers.
  • the ionic hydrophilic group is preferably an anionic ionic hydrophilic group (an ionic hydrophilic group that generates an anion when dissociated), a sulfo group, a carboxyl group, a thiocarboxyl group, a sulfino group, A phosphono group, a dihydroxyphosphino group, etc.
  • the number of ionic hydrophilic groups possessed by the compound represented by the general formula (1) is preferably 2 to 6, and more preferably 2 to 4.
  • the compound represented by the general formula (1) has a counter anion in the molecule.
  • the ionic hydrophilic group of the general formula (1) is an anionic ionic hydrophilic group, and the anion generated by dissociation of one of the anionic ionic hydrophilic groups is the counter anion.
  • the counter anion is particularly preferably a sulfonate group (—SO 3 ⁇ ) generated by dissociating a sulfo group.
  • a triphenylmethane compound is an ionic compound and has a resonance structure. For example, in the compound 001, the following (A) to (C) represent the same compound.
  • the compound represented by the general formula (1) is a compound represented by the following general formula (2).
  • R 201 and R 203 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R 202 and R 204 each independently represents an alkyl group, an aryl group, or a heterocyclic group.
  • R 221 , R 222 , R 223 and R 224 are each independently a halogen atom, alkyl group, cyano group, nitro group, alkoxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, amino group, acylamino group, aminocarbonyl Amino group, alkoxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, alkylthio group, sulfamoyl group, alkylsulfinyl group, alkylsulfonyl group, acyl group, alkoxycarbonyl group, carbamoyl group, imide group or sulfo group .
  • R 207 , R 208 , R 209 , R 210 and R 211 each independently represent a substituent
  • X 201 , X 202 and X 203 each independently represent CH or a nitrogen atom.
  • at least one of X 201 to X 203 represents CH.
  • X 201 to X 203 represent CH
  • a hydrogen atom may be removed and R 209 may be bonded.
  • n 201 and n 202 each independently represents an integer of 0 to 3
  • n 203 represents an integer of 0 to 5
  • n 204 and n 205 each independently represents an integer of 0 or more.
  • n 201 , n 202 , n 203 , n 204, and n 205 each represent an integer of 2 or more, a plurality of R 207 , R 208 , R 209 , R 210, and R 211 are the same or different. Also good.
  • Ar 201 and Ar 202 each independently represent a benzene ring, a naphthalene ring, or an aromatic heterocycle.
  • the compound represented by the general formula (2) has at least two ionic hydrophilic groups.
  • the compound represented by the general formula (2) has a counter anion in the molecule.
  • R 201 , R 202 , R 203 , R 204 , R 207 , R 208 , R 209 , R 210 , R 211 , Ar 201 , and Ar 202 are The same as R 101 , R 102 , R 103 , R 104 , R 107 , R 108 , R 109 , R 110 , R 111 , Ar 101 , and Ar 102 in (1).
  • preferred ranges of X 201 , X 202 , and X 203 are the same as X 101 , X 102 , and X 103 in the general formula (1).
  • n 201 , n 202 , n 203 , n 204 , and n 205 are n 101 , n 102 , n 103 , n 104 , and n 105 in the general formula (1).
  • R 221 and R 223 are the same as R 105 and R 106 in General Formula (1).
  • R 222 and R 224 are the same as those of R 221 and R 223 .
  • the compound represented by the general formula (2) has at least two ionic hydrophilic groups. Specific examples and preferred ranges of the ionic hydrophilic groups are the same as those described in the general formula (1).
  • the compound represented by the general formula (1) or (2) is preferably a compound represented by the following general formula (3).
  • R 301 and R 303 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R 302 and R 304 each independently represents an alkyl group, an aryl group, or a heterocyclic group.
  • R 321 , R 322 , R 323 and R 324 are each independently a halogen atom, alkyl group, cyano group, nitro group, alkoxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, amino group, acylamino group, aminocarbonyl Amino group, alkoxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, alkylthio group, sulfamoyl group, alkylsulfinyl group, alkylsulfonyl group, acyl group, alkoxycarbonyl group, carbamoyl group, imide group or sulfo group .
  • R 307 , R 308 , R 309 , R 310 and R 311 each independently represent a substituent
  • X 301 , X 302 and X 303 each independently represent CH or a nitrogen atom.
  • at least one of X 301 to X 303 represents CH.
  • X 301 to X 303 represent CH
  • a hydrogen atom may be removed and R 309 may be bonded.
  • n 301 and n 302 each independently represents an integer of 0 to 3
  • n 303 represents an integer of 0 to 5
  • n 304 and n 305 each independently represents an integer of 0 to 3.
  • n 301 , n 302 , n 303 , n 304, and n 305 each represent an integer of 2 or more, a plurality of R 307 , R 308 , R 309 , R 310, and R 311 are the same or different. Also good.
  • the compound represented by the general formula (3) has at least two ionic hydrophilic groups.
  • the compound represented by the general formula (3) has a counter anion in the molecule.
  • R 301 , R 302 , R 303 , R 304 , R 307 , R 308 , R 309 , R 310 , and R 311 are R in General Formula (1).
  • 101 , R 102 , R 103 , R 104 , R 107 , R 108 , R 109 , R 110 , and R 111 are the same.
  • the preferable ranges of X 301 , X 302 , and X 303 are the same as X 101 , X 102 , and X 103 in general formula (1).
  • n 301 , n 302 , and n 303 are the same as n 101 , n 102 , and n 103 in general formula (1).
  • n304 and n305 preferably represent 0 or 1.
  • specific examples and preferred ranges of R 321 , R 322 , R 323 , and R 324 are the same as R 221 , R 222 , R 223 , and R 224 in General Formula (2).
  • the compound represented by the general formula (3) has at least two ionic hydrophilic groups, and specific examples and preferred ranges of the ionic hydrophilic groups are the same as those described in the general formula (1).
  • the compound represented by the general formula (1), (2) or (3) is preferably a compound represented by the following general formula (4).
  • R 401 and R 403 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R 402 and R 404 each independently represents an alkyl group, an aryl group, or a heterocyclic group.
  • R 421 , R 422 , R 423 and R 424 are each independently a halogen atom, alkyl group, cyano group, nitro group, alkoxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, amino group, acylamino group, aminocarbonyl Amino group, alkoxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, alkylthio group, sulfamoyl group, alkylsulfinyl group, alkylsulfonyl group, acyl group, alkoxycarbonyl group, carbamoyl group, imide group or sulfo group .
  • R 407 , R 408 , R 409 , R 410 and R 411 each independently represent a substituent.
  • n 401 and n 402 each independently represents an integer of 0 to 3
  • n 403 represents an integer of 0 to 4
  • n 404 and n 405 each independently represents an integer of 0 to 3.
  • n 401 , n 402 , n 403 , n 404, and n 405 each represent an integer of 2 or more
  • a plurality of R 407 , R 408 , R 409 , R 410, and R 411 are the same or different. Also good.
  • the compound represented by the general formula (4) has at least two ionic hydrophilic groups.
  • R 401 , R 402 , R 403 , R 404 , R 407 , R 408 , R 409 , R 410 , and R 411 are R in the general formula (1).
  • 101 , R 102 , R 103 , R 104 , R 107 , R 108 , R 109 , R 110 , and R 111 are the same.
  • preferred ranges of n 401 , n 402 , n 403 , n 404 , and n 405 are n 301 , n 302 , n 303 , n 304 , and n 305 in the general formula (3) . The same.
  • R 421 , R 422 , R 423 and R 424 are the same as R 221 , R 222 , R 223 and R 224 in General Formula (2).
  • the compound represented by the general formula (4) has a sulfonate group (—SO 3 ⁇ ), and the number of ionic hydrophilic groups possessed by the compound represented by the general formula (4) including the sulfonate group. Is preferably from 2 to 6, more preferably from 2 to 4. Specific examples and preferred ranges of the ionic hydrophilic group are the same as those described in the general formula (1).
  • the compound represented by the general formula (1), (2), (3) or (4) is a compound represented by the following general formula (5).
  • R 501 and R 502 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R 521 , R 522 , R 523 , R 524 , R 531 and R 532 are each independently a halogen atom, alkyl group, cyano group, nitro group, alkoxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, amino group , Acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, alkylthio group, sulfamoyl group, alkylsulfinyl group, alkylsulfonyl group, acyl group, alkoxycarbonyl group, carbamoyl group, imide Represents a group or a sulfo group.
  • R 507 , R 508 , R 509 , R 510 , R 511 , R 512 and R 513 each independently represent a substituent.
  • n 501 and n 502 each independently represents an integer of 0 to 3
  • n 503 represents an integer of 0 to 4
  • n 504 and n 505 each independently represents an integer of 0 to 3
  • n 506 and n 507 Each independently represents an integer of 0 or more.
  • n 501 , n 502 , n 503 , n 504 , n 505 , n 506, and n 507 each represent an integer of 2 or more
  • a plurality of R 507 , R 508 , R 509 , R 510 , R 511 , R 512 And R 513 may be the same or different.
  • Ar 501 and Ar 502 each independently represent a benzene ring, a naphthalene ring, or an aromatic heterocycle.
  • the compound represented by the general formula (5) has at least two ionic hydrophilic groups.
  • R 501 , R 502 , R 507 , R 508 , R 509 , R 510 , R 511 , Ar 501 , and Ar 502 are R in the general formula (1).
  • 101 , R 103 , R 107 , R 108 , R 109 , R 110 , R 111 , Ar 101 , and Ar 102 are the same.
  • specific examples and preferred ranges of R 512 and R 513 are the same as those of R 507 , respectively.
  • R 521 , R 522 , R 523 , and R 524 are the same as R 221 , R 222 , R 223 , and R 224 in General Formula (2).
  • specific examples and preferred ranges of R 531 and R 532 are the same as those of R 521 and R 522 .
  • preferred ranges of n 501 , n 502 , n 503 , n 504 , and n 505 are n 301 , n 302 , n 303 , n 304 , and n 305 in the general formula (3) . The same.
  • the preferable range of n506 and n507 is the same as n104 and n105 in general formula (1).
  • the compound represented by the general formula (5) has a sulfonate group (—SO 3 ⁇ ), and the number of ionic hydrophilic groups possessed by the compound represented by the general formula (5) including this sulfonate group. Is preferably from 2 to 6, more preferably from 2 to 4. Specific examples and preferred ranges of the ionic hydrophilic group are the same as those described in the general formula (1).
  • the compound represented by the general formula (1), (2), (3), (4) or (5) is preferably a compound represented by the following general formula (6).
  • R601 and R602 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • R 621 , R 622 , R 623 , R 624 , R 631 , R 632 , R 633 and R 634 are each independently a halogen atom, alkyl group, cyano group, nitro group, alkoxy group, acyloxy group, carbamoyloxy group, alkoxy Carbonyloxy, amino, acylamino, aminocarbonylamino, alkoxycarbonylamino, sulfamoylamino, alkylsulfonylamino, alkylthio, sulfamoyl, alkylsulfinyl, alkylsulfonyl, acyl, alkoxycarbonyl Represents a group, a carbamoyl group, an imide group or a sulfo group.
  • R 607 , R 608 , R 609 , R 610 , R 611 , R 612 and R 613 each independently represent a substituent.
  • n 601 and n 602 each independently represents an integer of 0 to 3
  • n 603 represents an integer of 0 to 4
  • n 604 and n 605 each independently represents an integer of 0 to 3
  • n 606 and n 607 Each independently represents an integer of 0 to 3.
  • n 601 , n 602 , n 603 , n 604 , n 605 , n 606, and n 607 each represent an integer of 2 or more
  • a plurality of R 607 , R 608 , R 609 , R 610 , R 611 , R 612 And R 613 may be the same or different.
  • the compound represented by the general formula (6) has at least two ionic hydrophilic groups.
  • R 601 , R 602 , R 607 , R 608 , R 609 , R 610 , and R 611 are R 101 , R 103 , R in General Formula (1). 107 , R 108 , R 109 , R 110 , and R 111 are the same.
  • specific examples and preferred ranges of R 612 and R 613 are the same as R 512 and R 513 in General Formula (5).
  • specific examples and preferred ranges of R 621 , R 622 , R 623 , and R 624 are the same as R 221 , R 222 , R 223 , and R 224 in General Formula (2). .
  • R 631 , R 632 , R 633 and R 634 are the same as those of R 621 , R 622 , R 623 and R 624 .
  • preferred ranges of n 601 , n 602 , n 603 , n 604 , and n 605 are n 301 , n 302 , n 303 , n 304 , and n 305 in general formula (3) .
  • a preferred range of n 606 and n 607 are the same as n 604 and n 605.
  • the compound represented by the general formula (6) has a sulfonate group (—SO 3 ⁇ ), and the number of ionic hydrophilic groups possessed by the compound represented by the general formula (6) including this sulfonate group. Is preferably from 2 to 6, more preferably from 2 to 4. Specific examples and preferred ranges of the ionic hydrophilic group are the same as those described in the general formula (1).
  • Me represents a methyl group
  • Et represents an ethyl group
  • iPr represents an isopropyl group
  • a tBu group represents a tert-butyl group
  • Ph represents a phenyl group.
  • Synthesis method A method for synthesizing the compound represented by any one of the general formulas (1) to (6) will be described. It can be synthesized according to a conventionally known method for synthesizing triarylmethane dyes. For example, a compound of the general formulas (1) to (6) can be obtained by subjecting 2 equivalents of an aniline derivative and 1 equivalent of a benzaldehyde derivative to a condensation reaction, followed by oxidation.
  • the method for introducing an aryl group substituted at the ortho position can be obtained, for example, by Suzuki-Miyaura coupling between an ortho-position haloaniline and an aryl boron derivative.
  • substituents substituted on the N atom of the aniline derivative R 101 , R 102 , R 103 , R 104 in formula (1)
  • aniline and the corresponding halogenated alkane are used as bases. It can be obtained by reacting in the presence.
  • An aryl group or a heterocyclic group can be obtained by an Ullmann reaction or a Backward-Hartwig-cross coupling reaction between aniline and a corresponding aryl halide or halogenated heterocycle.
  • the method for producing the compounds represented by the general formulas (1) to (6) can be synthesized by a known production method and is not limited to the above method.
  • the coloring composition of this invention contains the compound represented by the said General formula (1) at least.
  • the coloring composition of this invention may contain only 1 type of compounds represented by General formula (1), and may contain 2 or more types.
  • the coloring composition of the present invention may contain only the compound represented by the general formula (1) as a coloring agent. However, other coloring agents may be used as long as the effects of the present invention are not impaired. May be contained. Examples of the colorant that may be used in combination include known dyes such as dyeing notes (24th edition issued by Color Dyeing Co., Ltd. and the like), dyes on pages 33 to 121, and pigments on pages 124 to 130. Etc.
  • the content of the compound represented by the general formula (1) in the coloring composition is preferably 1 to 20% by mass, and more preferably 1 to 10% by mass.
  • the content of the compound represented by the general formula (1) contained in the coloring composition is preferably 1 to 20% by mass, and more preferably 1 to 10% by mass.
  • the colored composition in the present invention generally contains a solvent.
  • the type and amount of the solvent vary depending on the type of the compound represented by the general formula (1), the dyeing concentration, and the dyeing method, but the solvent is preferably contained in an amount of 40% by mass or more based on the total amount of the colored composition. .
  • a solvent it is preferable to contain water, and it is preferable to contain 50 mass% or more of water with respect to the solvent whole quantity. Moreover, it is preferable to contain 30 mass% or more of water with respect to the whole quantity of a coloring composition.
  • the recording medium for printing the colored composition of the present invention includes various fabrics, paper, coated paper coated with an ink receiving layer, a plastic film, and the like. Development of ink suitable for ink jet recording has also been performed.
  • the coloring composition of the present invention is preferably a coloring composition for dyeing, and is used for coloring compositions for dyeing on fabrics, ink for ink jet recording for printing on paper, color toners, resists for color filters, and the like. However, it is particularly suitable as a coloring composition for dyeing a fabric.
  • the coloring composition for dyeing of the present invention is preferably a coloring composition for dyeing fibers (coloring composition for printing).
  • the dyeing method for fibers is roughly divided into a dip dyeing method and a printing method. Dipping is a process in which a dyed cloth or yarn is immersed in a dye solution in which a dye is dissolved or dispersed in a solvent, uniformly adsorbed on the fiber surface, diffused into the fiber, and dyed by bonding. is there.
  • Textile printing is a dyeing method in which dyes or pigments are applied onto a fabric to give a pattern shape, and dyed pigments are dyed or fixed to make a dyed product with a pattern. The pattern effect is developed on the fabric to be dyed. Industrially, screen printing using a plate, roller printing, transfer printing using transfer paper, and ink-jet printing without plate making are performed.
  • the dip dyeing comprises a step of immersing a fabric or thread in a dye solution to dye the dye, a washing step of washing away unfixed dye that is not dyed on the fiber, and a drying step.
  • the colored composition of the present invention is used as a dyeing solution capable of immersing a fabric or yarn.
  • the dyeing solution may contain a solvent, a leveling assistant, a pH adjuster, an inorganic neutral salt, a dispersant and the like in addition to the dye.
  • water is used as the solvent.
  • Known additives can be used as additives such as leveling assistants.
  • the dye In order to dye the dye uniformly at a high concentration, it can be adjusted by controlling the dye concentration, dye bath pH, salt concentration, dyeing temperature, dyeing time, pressure, and liquid flow, in addition to using the additive.
  • water or hot water in the range from room temperature to 100 ° C. is generally used.
  • the water to be washed may contain a soaping agent.
  • good results can be obtained in various water resistances such as washing fastness and sweat fastness.
  • the washed fabric is squeezed or dehydrated and then dried or dried using a dryer, heat roll, iron, or the like.
  • the textile printing method of the present invention preferably includes at least the following steps (1) to (4).
  • a step of adding a coloring composition of the present invention to a liquid containing at least a polymer compound and water to prepare a color paste (2)
  • a step of printing the color paste of (1) on a fabric (3)
  • the process of applying steam to the printed fabric (4)
  • the process of washing the printed fabric with water and drying the washed fabric it is preferable to satisfy the printing appropriateness necessary for the printed matter, such as washing with water.
  • the color paste can contain a paste, a solvent, a dyeing assistant and the like in addition to the dye.
  • the paste is a medium for the colored composition, and a water-soluble polymer is preferably used.
  • the water-soluble polymer include known natural water-soluble polymers such as starches, seaweeds, natural gums, cellulose derivatives, sodium alginate, protein substances, tannin substances, and lignin substances.
  • known synthetic polymers such as polyvinyl alcohol compounds, polyethylene oxide compounds, acrylic acid-based aqueous polymers, styrene-based aqueous polymers, and maleic anhydride-based aqueous polymers are also used as the paste.
  • a water-soluble solvent is preferably used, and a solvent containing at least water is most preferably used.
  • Coloring agents such as acids and alkalis, dye solubilizers, wetting agents, hygroscopic agents, thickening agents, anti-reduction agents, metal ion sealing agents, ultraviolet absorbers, dispersants, anti-dyeing agents, and discharge Agents, antiseptics, antifungal agents, antioxidants, migration inhibitors, dye fixing agents, antifoaming agents and the like.
  • a dyeing aid is added to a paste solution in which the paste is dissolved or dispersed in a solvent, and then a dye solution in which the dye is dissolved or dispersed in the solvent is added and stirred to prepare the color paste.
  • a dyeing aid is added to a paste solution in which the paste is dissolved or dispersed in a solvent, and then a dye solution in which the dye is dissolved or dispersed in the solvent is added and stirred to prepare the color paste.
  • the printing method unlike the dip dyeing method, after the color paste is printed on the fabric (the step of printing the color paste on the fabric), the color material printed on the fabric is dyed onto the fiber.
  • This is called a coloring process, and there are a method using heated air, a method using normal pressure saturated steam and superheated steam, and a method using normal pressure saturated steam is preferred.
  • the temperature and time for treatment with steam vary depending on the type of the colored composition and the type of the fabric, but the temperature is preferably 90 ° C to 140 ° C, more preferably 100 ° C to 108 ° C. preferable.
  • the time is preferably 1 to 60 minutes, more preferably 1 to 30 minutes.
  • a printed product is obtained through a washing process and a drying process similar to the dip dyeing.
  • the fabric preferably contains polyamide.
  • the colored composition of the present invention is preferably used as an ink for inkjet printing.
  • “Inkjet ink” is ink used in a printing machine (inkjet printer) having a mechanism for ejecting ink from an inkjet nozzle to form an image.
  • the ink used for textile printing using inkjet is called ink for inkjet textile printing.
  • the inkjet textile printing method of the present invention preferably includes the following steps (11) to (14).
  • a step of applying a paste containing at least a polymer compound and water to a fabric (12) A step of printing the ink-jet ink of the present invention on a fabric by an inkjet method (13) A step of applying steam to the printed fabric ( 14) The process of washing and drying the printed fabric
  • the inkjet printing method tends to cause clogging of the nozzle when the color paste used in the conventional printing method is used.
  • It is preferable to perform a pretreatment step (a step of applying a paste containing at least a polymer compound and water to the fabric). By performing the pretreatment step, the fabric can be easily handled. Specifically, a pretreated fabric is obtained by attaching a paste solution containing a paste, a solvent and a hydrotropic agent to the fabric and drying it.
  • the fabric preferably contains polyamide.
  • the paste the same paste as used in screen printing or the like can be used.
  • the solvent a water-soluble solvent is preferably used, and a solvent containing at least water is most preferably used.
  • the hydrotropic agent generally serves to increase the color density of an image when the fabric to which the ink composition is applied is heated under steam.
  • urea, alkylurea, ethyleneurea, propyleneurea, thiourea, guanidate, halogen-valent tetraalkylammonium and the like are usually used.
  • known ones can be used, and examples thereof include dye fixing agents described on pages 426 to 429 of dyeing notes.
  • the content of the hydrotropic agent with respect to the total solid content of the paste solution is preferably 0.01% by mass to 20% by mass.
  • the paste solution may further contain a pH adjuster, an aqueous (water-soluble) metal salt, a water repellent, a surfactant, a migration inhibitor, a microporous forming agent, and the like as necessary.
  • the paste solution is preferably put in a range of 5% to 150%, preferably 10% to 130%.
  • a method for incorporating the respective paste solutions into the fabric is not particularly limited, and examples include a usual dipping method, pad method, coating method, screen method, spray method, transfer method, and ink jet method. .
  • the ink for inkjet printing can be produced by dissolving and / or dispersing the compound represented by the general formula (1) in an oleophilic medium or an aqueous medium.
  • the ink uses an aqueous medium. Therefore, for the purpose of imparting appropriate ink, proper printing, and image fastness, the ink-jet printing ink can contain a solvent and a surfactant in addition to the dye.
  • the solvent is determined by the type of substituent in the compound represented by the general formula (1) to be used, the type of solvent component used to produce the colored composition, the type of fabric to be dyed, and the like.
  • An aqueous medium more preferably water or a water-soluble organic solvent is used.
  • the solvent can be prepared by dissolving and / or dispersing the compound represented by the general formula (1) in a lipophilic solvent or a water-soluble solvent.
  • the organic solvent that can be contained in the ink-jet printing ink of the present invention is preferably an aqueous organic solvent.
  • polyhydric alcohols such as diethylene glycol and glycerin, amines, monohydric alcohols, polyhydric alcohols can be used. Examples thereof include alkyl ethers.
  • each compound exemplified as an example of the water-miscible organic solvent described in paragraph [0076] of JP-A No. 2002-371079 is preferable.
  • the content of the organic solvent in the ink for inkjet printing of the present invention is preferably 10% by mass or more and 60% by mass or less with respect to the total mass of the ink for inkjet printing.
  • the surfactant any of cationic, anionic, amphoteric and nonionic surfactants can be used.
  • the ink for inkjet textile printing of this invention can contain another additive in the range which does not impair the effect of this invention as needed.
  • the ink for inkjet textile printing of the present invention preferably has a viscosity of 30 mPa ⁇ s or less.
  • the surface tension is preferably 25 mN / m or more and 70 mN / m or less.
  • Viscosity and surface tension are various additives such as viscosity modifiers, surface tension modifiers, specific resistance modifiers, film modifiers, UV absorbers, antioxidants, antifading agents, antifungal agents, and rust inhibitors. It can be adjusted by adding a dispersant and a surfactant.
  • the fabric printed by the inkjet method is dried and then subjected to a coloring process, a washing process, and a drying process in the same manner as other printing methods to obtain a printed product.
  • a preferred method of the color development step to the drying step is the same as that for screen printing.
  • the fabric used in the present invention may be pretreated if necessary.
  • the treatment may be performed before or after the paste is attached to the fabric.
  • you may add and use a pre-processing agent to the paste solution adhering before dyeing
  • the method for inkjet printing using the colored composition of the present invention is not limited as long as it includes a step of ejecting ink onto a fabric using an inkjet apparatus.
  • the compound represented by the general formula (1) contained in the coloring composition of the present invention can dye a fabric as a dye.
  • Various types of dyes can be prepared by changing the type of substituent of the compound represented by the general formula (1).
  • the compound represented by the general formula (1) contains at least one acidic group such as a sulfo group or a carboxyl group, as an acidic dye, protein fibers such as silk and wool, polyamide fibers such as 6 nylon and 66 nylon Can be dyed.
  • the compound represented by the general formula (1) is an oil-soluble compound insoluble in water, it is common to dye hydrophobic fibers such as polyester as a disperse dye, but also dye acrylic resins and polyamide fibers. be able to.
  • an acrylic fiber can be dyed as a cationic dye.
  • cellulose fiber such as cotton or polyamide fiber can be dyed as a reactive dye.
  • Specific examples of the group that reacts with the fiber include a chlorotriazinyl group, a chloropyrimidyl group, a vinylsulfonyl group, a chloroethylsulfonyl group, a sulfatoethylsulfonyl group, and a thiosulfatoethylsulfonyl group.
  • a fabric composed of one type of fiber may be used, or a composite fiber composed of two or more types of fibers may be used.
  • the compound represented by the general formula (1) is preferably an acid dye, and particularly has a high dyeing property when dyeing polyamide fibers, and has light resistance, water resistance, and resistance to light. Various performances such as chlorination can be improved.
  • a polyamide fiber As a preferable polyamide fiber as a fabric to be dyed, a polyamide fiber may be used as long as it contains a polyamide fiber, and a fabric made of polyamide alone or a fabric made of composite fiber may be used.
  • the composite fiber include fibers described in JP-A-2008-202210, JP-A-2006-322131, JP-A-2007-100200, and the like.
  • polyamide fibers fibers containing 6 nylon and 66 nylon are preferable.
  • the fiber used is preferably a fabric, but the same effect can be obtained even if the yarn is dyed.
  • the obtained residue was purified by column chromatography (filler: silica gel, developing solution: n-hexane / ethyl acetate (10/1)) to obtain 13 g of intermediate 001-1.
  • 10 g of the intermediate 001-1 and 50 mL of ethanol were stirred at room temperature for 30 minutes.
  • 3g of acetaldehyde was added here, and also it stirred for 30 minutes at room temperature.
  • 10 g of sodium borohydride was added in increments of 1 g while paying attention to foaming, and the mixture was further stirred for 1 hour.
  • the reaction solution was poured into 100 mL of 1M hydrochloric acid, extracted with ethyl acetate, and then concentrated under reduced pressure using an evaporator.
  • the obtained residue was purified by column chromatography (filler: silica gel, developing solution: n-hexane / ethyl acetate (10/1)) to obtain 8 g of intermediate 001-2.
  • 21 g of the intermediate 001-2, 12 g of disodium 4-formylbenzene-1,3-disulfonate, and 80 mL of methanesulfonic acid were placed in a flask and stirred at 130 ° C. for 6 hours.
  • the obtained reaction solution was poured into 500 mL of ice water, and the crystals of the obtained intermediate 001-3 were collected by filtration (20 g).
  • the obtained residue was purified by column chromatography (filler: silica gel, developing solution: n-hexane / ethyl acetate (10/1)) to obtain 15 g of intermediate 004-1.
  • 33 g of intermediate 004-1, 12 g of disodium 4-formylbenzene-1,3-disulfonate, and 80 mL of methanesulfonic acid were placed in the flask and stirred at 130 ° C. for 6 hours.
  • the obtained reaction liquid was poured into 500 mL of ice water, and the crystals of the obtained intermediate 004-2 were collected by filtration (25 g).
  • the flask was mixed with 10 g of intermediate 004-2, 3.4 g of chloranil, and 200 mL of methanol, and stirred at 65 ° C. for 3 days. The temperature was returned to room temperature, and the obtained crystals of intermediate 004-3 were collected by filtration (8 g). Compound 004-3 (5 g) and sulfuric acid (20 mL) were added and stirred while cooling. To this, 15 mL of 25% fuming sulfuric acid was added dropwise over 4 hours so that the internal temperature did not exceed 5 ° C. After stirring for 30 minutes at an internal temperature of 5 ° C. or less, the reaction solution was poured onto 200 g of ice and the precipitated crystals were collected by filtration.
  • the obtained residue was purified by column chromatography (filler: silica gel, developing solution: n-hexane / ethyl acetate (10/1)) to obtain 16 g of Intermediate 007-1.
  • 33 g of intermediate 007-1, 12 g of disodium 4-formylbenzene-1,3-disulfonate, and 80 mL of methanesulfonic acid were placed in the flask and stirred at 130 ° C. for 6 hours.
  • the obtained reaction solution was poured into 500 mL of ice water, and the crystals of the obtained intermediate 007-2 were collected by filtration (27 g).
  • 2,6-Diisopropylbromobenzene was obtained by the method described in the published patent (WO2015-14835A1).
  • Compound 012 was obtained by synthesizing by the same synthesis method, replacing bromomesitylene with 2,6-diisopropylbromobenzene.
  • [lambda] max 615 nm (aqueous solution).
  • 2,6-Diisopropylphenylboric acid was obtained by a method described in a known document (Dalton Transactions, 2015, 44, 8552). To the flask, 21 g of 2,6-diisopropylphenylboric acid, 17 g of o-bromoaniline, 30 g of tert-butoxypotassium, 100 mL of 1,4-dioxane and 100 mL of water were added and stirred for 1 hour under a nitrogen atmosphere. .
  • 2,6-Diethyl-4-methylphenylboric acid was obtained by the method described in the published patent (WO2008-11038A2).
  • 2,6-diisopropylphenylboric acid was changed to 2,6-diethyl-4-methylphenylboric acid and synthesized by the same synthesis method to obtain Compound 010.
  • [lambda] max 616 nm (aqueous solution).
  • Inkjet printing evaluation Ink jet textile printing was performed according to the method described in JP2013-209786A. ⁇ Pretreatment process> About the nylon 6 jersey which is a fabric, the component shown below was mixed and the pretreatment agent A was prepared. Using the obtained pretreatment agent A, the fabric was put at a drawing ratio of 50% and naturally dried to obtain a treated fabric.
  • Pretreatment agent A ⁇ Glue: Guar gum [Nippon Co., Ltd. MEYPRO GUM NP] 2g ⁇ Hydrotropy: Urea (Wako Pure Chemical Industries) 5g ⁇ PH adjuster: ammonium sulfate (manufactured by Wako Pure Chemical Industries, Ltd.) 4g ⁇ Water 89g
  • CMYK density was measured under the above conditions, and the color density was measured with the reflection density of C (Cyan) as OD-Cyan. The results are shown in “OD value (cyan)” in Table 1 below.
  • the prepared dyed sample was subjected to a light resistance test based on the third exposure method of “JIS L0842 Test Method for Dye Fastness to Ultraviolet Carbon Arc Lamp Light”.
  • the dyed fabric was irradiated with an ultraviolet carbon lamp for 5 hours.
  • nylon 66 jersey or nylon 6 taffeta was used as the fabric instead of nylon 6 jersey, the same light resistance results were obtained. Further, the fabric dyed by nylon dyeing instead of inkjet printing and dyed into nylon 6 jersey, nylon 66 jersey, and nylon 6 taffeta showed the same OD value, hue and light resistance as the fabric dyed by inkjet printing.
  • the colored composition of the present invention has an excellent cyan optical density and excellent light resistance. Moreover, the inkjet ink containing the said coloring composition and the textile printing method can be provided. Furthermore, the compound of the present invention has excellent cyan optical density and light resistance.

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

Abstract

L'invention fournit un composé représenté par la formule générale (1) définie dans la description, une composition colorante comprenant ledit composé, une encre pour jet d'encre comprenant ladite composition colorante, et un procédé d'impression sur tissu.
PCT/JP2016/085446 2015-12-25 2016-11-29 Composition colorante, encre pour jet d'encre, procédé d'impression sur tissu, et composé Ceased WO2017110387A1 (fr)

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
CN108640909A (zh) * 2018-06-29 2018-10-12 山东朱氏药业集团有限公司 一种二呋喃甲酚紫磺酸内酯及其制备方法和使用方法

Citations (5)

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Publication number Priority date Publication date Assignee Title
GB614391A (en) * 1944-03-11 1948-12-15 Gen Printing Ink Corp Improvements in or relating to dyes and manufacture thereof
US3883529A (en) * 1971-12-15 1975-05-13 Ici Ltd New cellulose reactive dyestuffs
JPH09240149A (ja) * 1996-03-13 1997-09-16 Ricoh Co Ltd 光記録媒体
WO2009078970A1 (fr) * 2007-12-14 2009-06-25 Biotium, Inc. Composés fluorescents
JP2010204132A (ja) * 2008-02-27 2010-09-16 Mitsubishi Chemicals Corp カラーフィルター用着色樹脂組成物、カラーフィルター、有機ｅｌディスプレイおよび液晶表示装置

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Publication number Priority date Publication date Assignee Title
GB614391A (en) * 1944-03-11 1948-12-15 Gen Printing Ink Corp Improvements in or relating to dyes and manufacture thereof
US3883529A (en) * 1971-12-15 1975-05-13 Ici Ltd New cellulose reactive dyestuffs
JPH09240149A (ja) * 1996-03-13 1997-09-16 Ricoh Co Ltd 光記録媒体
WO2009078970A1 (fr) * 2007-12-14 2009-06-25 Biotium, Inc. Composés fluorescents
JP2010204132A (ja) * 2008-02-27 2010-09-16 Mitsubishi Chemicals Corp カラーフィルター用着色樹脂組成物、カラーフィルター、有機ｅｌディスプレイおよび液晶表示装置

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ALINEZHAD, H. ET AL.: "Synthesis of 4,4' - diaminotriphenylmethane derivatives using H3PW12O40 and HZSM5 zeolite under solvent-free conditions", J. IRAN. CHEM. SOC., vol. 6, no. 4, 2009, pages 816 - 822, XP055395820 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108640909A (zh) * 2018-06-29 2018-10-12 山东朱氏药业集团有限公司 一种二呋喃甲酚紫磺酸内酯及其制备方法和使用方法

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