WO2024122629A1 - Colorant pour colorer utilisant du dioxyde de carbone supercritique - Google Patents

Colorant pour colorer utilisant du dioxyde de carbone supercritique Download PDF

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Publication number
WO2024122629A1
WO2024122629A1 PCT/JP2023/043964 JP2023043964W WO2024122629A1 WO 2024122629 A1 WO2024122629 A1 WO 2024122629A1 JP 2023043964 W JP2023043964 W JP 2023043964W WO 2024122629 A1 WO2024122629 A1 WO 2024122629A1
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carbon atoms
alkyl group
aralkyl group
formula
group
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PCT/JP2023/043964
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English (en)
Japanese (ja)
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松本敏昭
小林樹
杉村亮治
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紀和化学工業株式会社
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Publication of WO2024122629A1 publication Critical patent/WO2024122629A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • 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
    • 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
    • D06P1/94—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 dyes dissolved in solvents which are in the supercritical state

Definitions

  • the present invention relates to a dye for dyeing fibers using supercritical carbon dioxide, a method for dyeing fibers using supercritical carbon dioxide, fibers dyed by the dyeing method, and compounds.
  • JP 41-3515 B describes an example of the production of a blue dye in which a phenoxy group having an alkyl group with 1 to 9 carbon atoms or a halogeno group as a substituent is introduced into an anthraquinone dye, and an example of the dyeing of polyolefin resin fibers using the dye.
  • the supercritical carbon dioxide dyeing equipment used for dyeing is shown.
  • the present invention also provides a fiber dyed by a dyeing method including a step of dyeing a fiber in the presence of supercritical carbon dioxide using the dye of the present invention.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms;
  • R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • dyes containing the following specific compounds have improved affinity for fibers and dye fibers a high concentration of yellow in the presence of supercritical carbon dioxide, and thus completed the present invention.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms;
  • R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R1 and R2 are each independently an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R1 and R2 are each independently an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 are each independently an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.
  • R 1 and R 2 are each independently an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.
  • R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 are each independently an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 or 2 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms
  • R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms
  • R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • R 1 and R 2 are each independently preferably an optionally branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, preferably an optionally branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and more preferably an optionally branched alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 are each independently preferably an optionally branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, preferably an optionally branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, preferably an optionally branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and preferably an optionally branched alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atom
  • R 1 and R 2 are each independently preferably an optionally branched alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, more preferably an optionally branched alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, still more preferably an optionally branched alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 3 , R 4 , R 5 , and R 6 are each independently a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 are each independently an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 are each independently an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 are each independently an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.
  • R 1 and R 2 are each independently an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 are each independently an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 12 carbon atoms.
  • R 1 and R 2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms.
  • R1 and R2 are each independently an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms.
  • R 1 and R 2 are each independently an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having one carbon atom.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms or an aralkyl group having 7 to 9 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having one carbon atom.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 12 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 12 carbon atoms or an aralkyl group having 7 to 9 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having one carbon atom.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 10 carbon atoms or an aralkyl group having 7 to 9 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having one carbon atom.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or an aralkyl group having 7 to 9 carbon atoms substituted with an alkyl group having 1 to 2 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 7 to 9 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 8 carbon atoms, an aralkyl group having 7 carbon atoms, or an aralkyl group having 7 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms; It is more preferable that R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having one carbon atom.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 6 carbon atoms;
  • R 3 , R 4 and R 6 each represent a hydrogen atom;
  • R5 is preferably an alkyl group having 1 to 4 carbon atoms.
  • the compound of formula (I) of the dye from the viewpoints of dye concentration, light fastness, sublimation fastness, etc., the following compounds are preferred, and the compounds of formulas (1) and (2) are more preferred.
  • the compound represented by formula (I) can be obtained by formylation of an aniline derivative represented by formula (i-A) (in formula (i-A), R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), followed by a condensation reaction with malononitrile.
  • R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms
  • R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen
  • the reaction temperature for the formylation is preferably 0 to 20°C, more preferably 0 to 10°C.
  • a compound represented by formula (i-A1) is reacted with an alkyl halide or an aralkyl halide represented by R 1 -X and R 2 -X (R 1 and R 2 each independently represent an alkyl group having 4 to 14 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, and X represents a halogen atom) to obtain a compound represented by formula (i-A).
  • the dyes of the present invention have the compound of formula (I).
  • the dye of the present invention may further contain additives.
  • additives include auxiliary colorants, dispersants, fillers, stabilizers, plasticizers, crystal nucleating agents, modifiers, foaming agents, UV absorbers, light stabilizers, antioxidants, antibacterial agents, antifungal agents, antistatic agents, flame retardants, inorganic fillers, and elastomers for improving impact resistance.
  • fibers to be dyed with the dye composition of the present invention include polyester fibers, polyolefin fibers, acrylic fibers, etc., and polyolefin fibers are preferred. Furthermore, polyolefin fibers are more preferred as the fibers to be dyed with the dye of the present invention.
  • the polyolefin fibers may be, for example, fibers formed from a polymer selected from homopolymers of ⁇ -olefins such as propylene, ethylene, 1-butene, 3-methyl-1-butene, 4-methyl-1-pentene, 1-octene, etc., copolymers of these ⁇ -olefins, or copolymers of these ⁇ -olefins with other unsaturated monomers that can be copolymerized with these ⁇ -olefins.
  • the types of copolymers may be, for example, block copolymers, random copolymers, graft copolymers, etc.
  • polymers include polypropylene-based resins such as propylene homopolymers, propylene-ethylene block copolymers, propylene-ethylene random copolymers, and propylene-ethylene-(1-butene) copolymers, polyethylene-based resins such as low-density polyethylene, medium-density polyethylene, high-density polyethylene, linear low-density polyethylene, ethylene-vinyl acetate copolymers, and ethylene-ethyl acrylate copolymers, poly-1-butene, poly-4-methyl-1-pentene, etc.
  • polypropylene-based resins such as propylene homopolymers, propylene-ethylene block copolymers, propylene-ethylene random copolymers, and propylene-ethylene-(1-butene) copolymers
  • polyethylene-based resins such as low-density polyethylene, medium-density polyethylene, high-density polyethylene, linear low-density polyethylene
  • the above polymers may be used alone or in combination to form polyolefin fibers.
  • the polyolefin fibers are preferably made of polypropylene-based resin and/or polyethylene-based resin, and more preferably made of polypropylene-based resin.
  • the polyolefin fiber may be in any shape, such as a block (molded product, etc.), a film, or a fiber (fabric (woven fabric, knitted fabric, nonwoven fabric, etc.), thread (filament yarn, spun yarn, slit yarn, split yarn, etc.), etc.), and is preferably in a fiber shape.
  • the polyolefin fiber may be a fiber formed by blending other polymer components with polypropylene resin and/or polyethylene resin, bonding, etc.
  • the polyolefin fiber may be a fiber obtained by blending or blending polypropylene fiber with other fibers such as polyester.
  • the present invention relates to a method for dyeing a fiber using supercritical carbon dioxide, which comprises a step of dyeing a fiber with the dye of the present invention in the presence of supercritical carbon dioxide.
  • supercritical carbon dioxide is used as a dyeing medium.
  • the dyeing method that uses supercritical carbon dioxide as the dyeing medium does not use water during dyeing, does not require a washing process, and therefore does not generate wastewater, does not require dyeing auxiliaries, has a short dyeing time, and allows the carbon dioxide dyeing medium to be reused. As a result, it has attracted attention as an environmentally friendly dyeing method.
  • the dye of the present invention when used to dye fibers or the like that use polyolefin resin, the dye of the present invention and the polyolefin resin are both lipophilic, so there is a high affinity between the dyeing medium, the dye and the object to be dyed, resulting in a high-quality dyed product.
  • the dyeing process in the fiber dyeing method using supercritical carbon dioxide of the present invention is preferably carried out at a temperature of 31°C or higher and a pressure of 7.4 MPa or higher. This is because the dyeing temperature and dyeing pressure must be equal to or higher than the critical point of carbon dioxide, which is the dyeing medium (7.4 MPa at 31°C).
  • the dyeing temperature is mainly determined by the type of resin in the fiber to be dyed.
  • the dyeing temperature is usually in the range of 60 to 180°C, and preferably in the range of 80 to 160°C.
  • the dyeing pressure is mainly determined by the type of resin in the dyed fiber.
  • the dyeing pressure is usually in the range of about 7.4 to 40.0 MPa, and preferably 20 to 30 MPa.
  • the dyeing time in the dyeing process is determined by the type of resin in the dyed fiber and the dyeing temperature.
  • the dyeing time is usually about 10 to 120 minutes, preferably 30 to 90 minutes.
  • the concentration of the dye relative to the fiber depends on the type and processing state of the fiber to be dyed.
  • the concentration of the dye relative to the fiber is 0.1 to 6.0% o.m.f. (on the mass of fiber), preferably 0.1 to 4.0% o.m.f.
  • the bath ratio (mass ratio of material to be dyed: carbon dioxide) depends on the type of material to be dyed and the processing state.
  • the bath ratio is usually 1:2 to 1:100, preferably 1:5 to 1:75.
  • the bath ratio in the dyeing method of the present invention is relatively low, for example, 1:2 to 1:5.
  • the present invention provides a fiber dyed by the dyeing method of the present invention.
  • the fiber is dyed to a high concentration, particularly a high concentration yellow, and has excellent color fastness to light, sublimation, washing, etc.
  • Applications of the fiber include, for example, clothing, underwear, hats, socks, gloves, sportswear, and other clothing items, vehicle interior materials such as seats, and interior goods such as carpets, curtains, mats, sofa covers, and cushion covers.
  • Step 1 A mixture of m-toluidine (10.6 g), triethylamine (25.2 g), DMF (30 g) and 1-bromooctane (57.9 g) was heated to 100° C. and stirred at the same temperature for 5 hours to obtain N,N-dioctyl-3-methylaniline represented by the following formula (1a) as a reaction mixture.
  • Step 2 The reaction mixture of N,N-dioctyl-3-methylaniline obtained in the above step 1 was cooled to 5°C. Phosphorus oxychloride (23.0 g) was added dropwise to this mixture over 1 hour at a temperature range of 5 to 10°C, pyridine (11.9 g) was added dropwise at a temperature range of 5 to 10°C, and the mixture was then heated to 40 to 45°C and stirred for 1 hour. This reaction mixture was cooled to 10°C, methanol (40 g) was added dropwise at a temperature range of 10 to 20°C, and anhydrous sodium acetate (35 g) was added at a temperature range of 10 to 20°C.
  • Step 1 N,N-dihexyl-3-methylaniline represented by the following formula (2a) was obtained as a reaction mixture in the same manner as in Step 1 of Synthesis Example 1, except that 1-bromohexane (49.5 g) was used instead of 1-bromooctane.
  • Step 2 A yellow dye compound represented by the following formula (2) (23.4 g, yield 66.7%) was obtained in the same manner as in step 2 of Synthesis Example 1, except that the reaction mixture of N,N-dihexyl-3-methylaniline obtained in step 1 was used instead of N,N-dioctyl-3-methylaniline.
  • the structure of the yellow dye compound was confirmed by LCMS analysis (m/z 352 (M + )).
  • Step 1 N,N-dioctylaniline represented by the following formula (3a) was obtained as a reaction mixture in the same manner as in Step 1 of Synthesis Example 1, except that aniline (9.31 g) was used instead of m-toluidine.
  • Step 2 A yellow dye compound represented by the following formula (3) (26.5 g, yield 67.4%) was obtained in the same manner as in step 2 of Synthesis Example 1, except that the reaction mixture of N,N-dioctylaniline obtained in step 1 was used instead of N,N-dioctyl-3-methylaniline.
  • the structure of the yellow dye compound was confirmed by LCMS analysis (m/z 394 (M+)).
  • Step 1 A mixture of N-benzylaniline (18.3 g), triethylamine (17.6 g), DMF (50 g) and 1-bromohexane (33.0 g) was heated to 110° C. and stirred at the same temperature for 8 hours to obtain N-benzyl-N-hexylaniline represented by the following formula (4a) as a reaction mixture.
  • Step 2 A yellow dye compound represented by the following formula (4) (21.2 g, yield 57.1%) was obtained in the same manner as in step 2 of Synthesis Example 1, except that the reaction mixture of N-benzyl-N-hexylaniline obtained in step 1 was used instead of N,N-dioctyl-3-methylaniline.
  • the structure of the yellow dye compound was confirmed by LCMS analysis (m/z 372 (M+)).
  • the reaction mixture was cooled to room temperature, and a mixture of 5-amino-anthra[9,1-cd]isothiazol-6-one (25.2 g) and toluene (30 g) was added dropwise to the reaction mixture.
  • the reaction mixture was heated to 110° C. and stirred for 2 hours, after which the solvent was distilled off from the mixture under reduced pressure, and methanol (100 g) was added to the residue to cause precipitation.
  • the mixture was filtered, and the filtered product was washed with methanol and then with water, and dried at 60° C. until the moisture content was 1.0 wt % or less, to obtain a yellow dye compound represented by the following formula (8) (36.7 g, yield 74.7%).
  • the structure of the yellow dye compound was confirmed by LCMS analysis (m/z 491 (M + )).
  • the reaction mixture was heated to 110°C and stirred for 2 hours, and then cooled to room temperature, and 20 g of a 24% aqueous sodium hydroxide solution was added, and 300 g of water was added to extract the organic layer. This extract was washed with saturated saline, and then the solvent was distilled off under reduced pressure, and methanol (300 g) was added to the residue to cause precipitation. The mixture was filtered, and the filtered product was washed with methanol and then with water, and dried at 60° C. until the moisture content was 1.0 wt % or less to obtain a yellow dye compound represented by the following formula (14) (22.6 g, yield 31.6%). The structure of the yellow dye compound was confirmed by LCMS analysis (m/z 715 (M + )).
  • the supercritical carbon dioxide dyeing apparatus used for dyeing is shown in Figure 1.
  • the dyeing apparatus is composed of a liquid CO2 cylinder (1), a filter (2), a cooling jacket (3), a cooler (4), a high-pressure pump (5), a preheater (6), pressure gauges (7 to 9), a magnetic drive unit (10), a DC motor (11), safety valves (12, 13), stop valves (14 to 18), a needle valve (19), and a heater (20).
  • the polypropylene cloth was cut into pieces of approximately 50 to 70 g, weighed, and wrapped around a stainless steel cylinder (21) with punched holes in the order of cotton cloth, polypropylene cloth, and cotton cloth from the inside, and then loosely secured with cotton thread.
  • the inner cotton cloth was the undercloth, and the outer cotton cloth was the cover cloth.
  • a stainless steel cylinder wrapped with the above-mentioned fabric samples (cotton fabric, polypropylene fabric, cotton fabric) was fixed to a pressure-resistant stainless steel tank (22), and the yellow dye compound 1 obtained in Synthesis Example 1, which corresponds to 0.3% by mass relative to the mass of the polypropylene fabric, was wrapped in a paper wipe and placed in the fluid passage at the top of the stainless steel cylinder.
  • the volume of the pressure-resistant stainless steel tank was 2230 cm3 . All valves in the dyeing apparatus were closed, and the tank was heated to 120°C by a preheater.
  • the stop valves (14) and (16) were opened, and 1.13 kg of liquid carbon dioxide was introduced into the pressure-resistant stainless steel tank using a high-pressure pump connected via a cooling jacket. After that, the stop valves (14) and (16) were closed, and the liquid was circulated by the impeller and magnetic drive unit at the bottom of the pressure-resistant stainless steel tank.
  • the rotation speed of the magnetic drive unit was 750 rpm, and the circulation direction was from the inside to the outside of the cylinder.
  • the polypropylene dyed fabrics obtained in dyeing examples P1 to P14 were subjected to dyeability evaluation, light fastness test, sublimation fastness test, washing fastness test, sweat fastness test, friction fastness test, and hot pressing fastness test.
  • Dyeability Evaluation was evaluated based on the total K/S value and K/S value (measured at the maximum wavelength) obtained by color measurement of the dyed fabric, and by visual inspection of the dye residue after dyeing.
  • the color of the dyed fabric was measured using an integrating sphere spectrophotometer Color-Eye 5 (manufactured by GretagMacbeth) with the dyed fabric glued onto white paper, under an observation light source of D65 and a 2-degree visual field.
  • the light fastness test was performed by the ultraviolet carbon arc lamp method according to JIS L0842: 2004.
  • the outline of the test method is as follows: Using an ultraviolet fade meter U48 (manufactured by Suga Test Instruments Co., Ltd.), the dyed fabric was exposed to light for 20 hours under the condition of a black panel temperature of 63 ⁇ 3° C., and then discoloration was judged.
  • Sublimation Fastness Test was performed according to JIS L0854: 2013. The outline of the test method is as follows: The dyed fabric was sandwiched between nylon fabrics and held at 120 ⁇ 2° C. for 80 minutes under a load of 12.5 kPa, and then the discoloration and staining of the nylon fabric were evaluated.
  • the washing fastness test was performed according to JIS L0844:2011 (A-2).
  • the outline of the test method is as follows. A multi-woven fabric was attached to the dyed fabric, and washed for 30 minutes at 50 ⁇ 2°C in the presence of soap, and discoloration and staining of the cotton and nylon parts of the multi-woven fabric were evaluated. In addition, staining of the residual liquid after washing was evaluated.
  • Sweat fastness test was performed according to JIS L0848: 2004.
  • the outline of the test method is as follows: A multi-woven fabric was attached to the dyed fabric, and the fabric was immersed in acidic artificial sweat or alkaline artificial sweat for 30 minutes, and then kept at 37 ⁇ 2°C for 4 hours under a load of 12.5 kPa, and then dried at 60°C or less, and the discoloration and staining of the cotton and nylon parts of the multi-woven fabric were evaluated.
  • Friction Fastness Test was performed according to JIS L0849:2013. The outline of the test method is as follows. Using a friction fastness tester RT-300 (manufactured by Daiei Scientific Instruments Co., Ltd.), the dyed fabric was rubbed back and forth 100 times with a dry cotton fabric or a wet cotton fabric under a load of 2N, and the coloring of the cotton fabric was judged.
  • Table 5 shows the evaluation results for dyeing examples using the compound of formula (I)
  • Table 6 shows the evaluation results for dyeing examples using dye compounds other than the compound of formula (I).
  • the present invention is not limited to the above-mentioned embodiments, and suitable combinations or substitutions of the configurations of the embodiments are also included in the present invention.
  • the present invention can be utilized for dyeing fibers used in clothing such as clothes, underwear, hats, socks, gloves, and sportswear, vehicle interior materials such as seat covers, and interior goods such as carpets, curtains, mats, sofa covers, and cushion covers.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Abstract

La présente invention aborde le problème de la fourniture : d'un colorant pour colorer des fibres à l'aide de dioxyde de carbone supercritique, qui peut colorer des fibres en jaune très dense et peut fournir un produit coloré ayant une excellente stabilité de couleur à la lumière, à la sublimation, au blanchissage et similaire ; d'un procédé de coloration de fibres à l'aide de dioxyde de carbone supercritique ; de fibres colorées par le procédé de coloration ; et d'un composé.　L'invention concerne : un colorant pour colorer des fibres à l'aide de dioxyde de carbone supercritique, le colorant comprenant un composé représenté par la formule (I) ; un procédé de coloration de fibres à l'aide de dioxyde de carbone supercritique ; des fibres colorées par le procédé de coloration ; et un composé. [Formule chimique 1] [Dans la formule (I), R1 et R2 représentent chacun indépendamment un groupe alkyle ayant de 4 à 14 atomes de carbone, un groupe aralkyle ayant de 7 à 12 atomes de carbone, ou un groupe aralkyle ayant de 7 à 12 atomes de carbone et substitué par un groupe alkyle ayant de 1 à 4 atomes de carbone ; et R3, R4, R5 et R6 représentent chacun indépendamment un atome d'hydrogène ou un groupe alkyle ayant de 1 à 4 atomes de carbone.]
PCT/JP2023/043964 2022-12-08 2023-12-08 Colorant pour colorer utilisant du dioxyde de carbone supercritique WO2024122629A1 (fr)

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Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5978895A (ja) * 1982-10-28 1984-05-07 Mitsubishi Chem Ind Ltd 感熱転写記録用色素
JPS60253596A (ja) * 1984-05-30 1985-12-14 Sumitomo Chem Co Ltd 昇華転写体
JPS61148096A (ja) * 1984-12-24 1986-07-05 Mitsubishi Chem Ind Ltd 転写シ−ト
JPS6364044A (ja) * 1986-09-05 1988-03-22 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
JPS63142062A (ja) * 1986-12-05 1988-06-14 Dainippon Printing Co Ltd 熱転写シ−ト用染料
JPH04245981A (ja) * 1990-09-03 1992-09-02 Ciba Geigy Ag 分散染料で疎水性繊維材料を染色する方法
JPH11100523A (ja) * 1997-09-29 1999-04-13 Mitsubishi Chemical Corp 気化性色素及びこれを用いた記録方法
JP2000247942A (ja) * 1999-02-23 2000-09-12 Mitsubishi Chemicals Corp スチリル系化合物
JP2001501661A (ja) * 1996-10-01 2001-02-06 ゼネカ・リミテッド 組成物
JP2013185126A (ja) * 2012-03-09 2013-09-19 Mitsubishi Chemicals Corp スチリル系、トリシアノビニル系化合物を含むインク

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5978895A (ja) * 1982-10-28 1984-05-07 Mitsubishi Chem Ind Ltd 感熱転写記録用色素
JPS60253596A (ja) * 1984-05-30 1985-12-14 Sumitomo Chem Co Ltd 昇華転写体
JPS61148096A (ja) * 1984-12-24 1986-07-05 Mitsubishi Chem Ind Ltd 転写シ−ト
JPS6364044A (ja) * 1986-09-05 1988-03-22 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
JPS63142062A (ja) * 1986-12-05 1988-06-14 Dainippon Printing Co Ltd 熱転写シ−ト用染料
JPH04245981A (ja) * 1990-09-03 1992-09-02 Ciba Geigy Ag 分散染料で疎水性繊維材料を染色する方法
JP2001501661A (ja) * 1996-10-01 2001-02-06 ゼネカ・リミテッド 組成物
JPH11100523A (ja) * 1997-09-29 1999-04-13 Mitsubishi Chemical Corp 気化性色素及びこれを用いた記録方法
JP2000247942A (ja) * 1999-02-23 2000-09-12 Mitsubishi Chemicals Corp スチリル系化合物
JP2013185126A (ja) * 2012-03-09 2013-09-19 Mitsubishi Chemicals Corp スチリル系、トリシアノビニル系化合物を含むインク

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