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WO2010123071A1 - Nouveau composé de triarylméthane - Google Patents

Nouveau composé de triarylméthane Download PDF

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Publication number
WO2010123071A1
WO2010123071A1 PCT/JP2010/057160 JP2010057160W WO2010123071A1 WO 2010123071 A1 WO2010123071 A1 WO 2010123071A1 JP 2010057160 W JP2010057160 W JP 2010057160W WO 2010123071 A1 WO2010123071 A1 WO 2010123071A1
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group
test
value
compound
parts
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PCT/JP2010/057160
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English (en)
Japanese (ja)
Inventor
高明 倉田
裕 石井
宜樹 赤谷
諒 寺西
あさ子 近藤
秀洋 新井
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日本化薬株式会社
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Priority to CN201080005820.XA priority Critical patent/CN102300938A/zh
Priority to JP2011510363A priority patent/JP5442004B2/ja
Publication of WO2010123071A1 publication Critical patent/WO2010123071A1/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
    • C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • 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
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/0086—Non common dispersing agents anionic dispersing agents
    • 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
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to novel triarylmethane compounds.
  • Triarylmethane dyes are characterized by their extremely sharp color and high color developability, and they are used as a wide range of applications such as various paints, water-based inks, oil-based inks, ink-jet inks, and color filter inks as violet, blue or green color materials. Used in In general, the properties required for coloring materials are different depending on the application, but the hue is sharp, high color forming ability is required, and in many applications, it is required that the coloring matter is fast to light, heat, etc. .
  • a cationic dye having a cationic group such as quaternary nitrogen in the structure and an anionic dye having an anionic group such as a sulfone group introduced into the cationic dye structure are known. Although all of them have excellent color forming properties, they have the disadvantage that they have poor fastness such as light resistance, heat resistance, moist heat resistance, water resistance and the like.
  • Patent Document 1 describes a salt compound of a cationic triarylmethane compound and a chloride ion or an arylsulfonate ion, but as a result of studies by the present inventors, a triarylmethane disclosed in this patent document The compound was insufficient in light resistance, heat resistance and water resistance.
  • Patent Document 2 also describes a triarylmethane cationic dye having a fluorinated alkylsulfonyl counter ion, but there is no specific example of a compound, and light resistance, heat resistance, moist heat resistance, water resistance, etc. There is no mention of robustness.
  • salt compounds of a cationic triphenylmethane compound and a chloride ion or an oxalate ion are commercially available, as a result of studies by the present inventors, these known triphenylmethane compounds have light resistance, heat resistance, and moisture resistance. The heat resistance and water resistance were insufficient.
  • the present invention is a novel triarylmethane compound which has the sharpness and color forming properties of triarylmethane dyes and is excellent in fastness such as light resistance, heat resistance, moist heat resistance, water resistance, etc. It is an object of the present invention to provide an oily or aqueous dye composition used.
  • the present inventors conducted intensive studies to solve the problems as described above, and as a result, a salt compound of cationic triarylmethane and a specific anion maintains the sharpness and colorability of triarylmethane dyes. And, it has been found that the light resistance, heat resistance, moisture heat resistance and water resistance are dramatically improved as compared with the prior art, and the present invention has been completed.
  • the present invention (1) triarylmethane compounds represented by the general formula (1), (In the formula (1), Ar 1 , Ar 2 and Ar 3 each independently represent an aromatic residue bonded to a central carbon atom by a carbon atom, and X ⁇ represents a bistrifluoromethanesulfonyl imide anion or tristrifluoromethanesulfonyl Represents methide anion) (2)
  • the triarylmethane compound according to (1) which is represented by the general formula (2):
  • R 1a to R 6a each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group or a benzyl group, and R 7a to R 20a each independently represent a hydrogen atom or carbon And represents an alkyl group of 1 to 6 or a halogen atom, and X - is as defined in the above formula (1))
  • the triarylmethane compound of the present invention is excellent in sharpness and color development as described above, and when it is formed into an oil or aqueous dye composition and processed into a dye colored body, exhibits superior fastness to conventional products. It is. That is, the triarylmethane compound of the present invention can be used as a dye-colored material, and can be applied to a wide range of applications such as color filter inks and inkjet inks.
  • the triarylmethane compound of the present invention is represented by the above formula (1).
  • Ar 1 , Ar 2 and Ar 3 each independently represent an aromatic residue bonded to a central carbon atom at a carbon atom.
  • the aromatic residue in Ar 1 , Ar 2 and Ar 3 of the formula (1) is, for example, an aromatic hydrocarbon residue such as phenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group and benzopyrenyl group; And aromatic heterocyclic residues such as pyridyl group, pyrazyl group, pyrimidyl group, quinolyl group, isoquinolyl group, pyrrolyl group, indoleyl group, imidazolyl group, carbazolyl group, thienyl group, furyl group, etc.
  • a naphthyl group is preferred.
  • a phenyl group or a naphthyl group may have a substituent, and the substituent is not particularly limited, but an aliphatic hydrocarbon residue, an aromatic Group, cyano group, isocyano group, thiocyanato group, isothiocyanato group, nitro group, acyl group, halogen atom, hydroxyl group, substituted or unsubstituted amino group, alkoxyl group, alkoxyalkyl group, and substituent group Aromatic oxy group, carboxyl group, carbamoyl group, aldehyde group, alkoxycarbonyl group, aromatic oxycarbonyl group and the like can be mentioned.
  • X 2 - represents a bistrifluoromethanesulfonylimide anion or a tristrifluoromethanesulfonyl methide anion, and among these, a tristrifluoromethanesulfonyl methide anion is preferable.
  • the compound of the above formula (2) is preferable in that it is excellent in fastness such as heat resistance, moist heat resistance and water resistance.
  • R 1a to R 6a each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group or a benzyl group
  • R 7a to R 20a each independently represent a hydrogen atom or a carbon number It represents an alkyl group of 1 to 6 and a halogen atom.
  • X - represents a bistrifluoromethanesulfonylimide anion or a tristrifluoromethanesulfonyl methide anion, and a tristrifluoromethanesulfonyl methide anion is particularly preferable.
  • examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a pentyl group, a cyclopentyl group, a hexyl group and a cyclohexyl group And alkyl groups such as 1-ethylpropyl group, 1-methylpropyl group and 1,2-dimethylpropyl group.
  • alkyl groups may have a substituent, and the substituent is not particularly limited, and as the alkyl group having 1 to 6 carbon atoms having a substituent, for example, hydroxyethyl group, hydroxypropyl group, Examples thereof include hydroxybutyl group, 2-sulfoethyl group, carboxyethyl group, cyanoethyl group, methoxyethyl group, ethoxyethyl group, butoxyethyl group, trifluoromethyl group, pentafluoroethyl group, phenylmethyl group and the like.
  • the phenyl group or the benzyl group may have a substituent, and examples of the substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group and a butyl group (C1-C5) alkyl group such as t-butyl group, pentyl group, etc., fluorine atom, halogen atom such as chlorine atom, bromine atom, iodine atom, etc., sulfonic acid group, methoxy group, ethoxy group, propoxy group, butoxy group (C1-C6) alkoxy group such as t-butoxy group and hexyloxy group; hydroxy (C1-C5) alkyl group such as hydroxyethyl group and hydroxypropyl group; methoxyethyl group, ethoxyethyl group, ethoxy (C1-C5) alkoxy (C1-
  • R 1a to R 6a of the formula (2) a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted phenyl group or an unsubstituted benzyl group is preferable.
  • R 7a to R 20a in the formula (2) include a hydrogen atom, a halogen atom, or a C 1 to C 6 unsubstituted alkyl group.
  • examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a pentyl group, a cyclopentyl group, a hexyl group and a cyclohexyl group And alkyl groups such as.
  • These alkyl groups may have a substituent, and the substituent is not particularly limited, and examples of the alkyl group having 1 to 6 carbon atoms having a substituent include hydroxyethyl, hydroxypropyl and hydroxy.
  • Examples thereof include a butyl group, 2-sulfoethyl group, carboxyethyl group, cyanoethyl group, methoxyethyl group, ethoxyethyl group, butoxyethyl group, trifluoromethyl group and pentafluoroethyl group.
  • Examples of the halogen atom in R 7a to R 20a of the formula (2) include fluorine, chlorine, bromine and iodine.
  • R 1b to R 4b each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group or a benzyl group
  • R 5b to R 16b each independently represent a hydrogen atom or a carbon number
  • R 1-7 represents an alkyl group or a halogen atom
  • R 17 b represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a halogen atom or an amino group.
  • X - represents a bistrifluoromethanesulfonylimide anion or a tristrifluoromethanesulfonyl methide anion, and a tristrifluoromethanesulfonyl methide anion is particularly preferred.
  • examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a pentyl group, a cyclopentyl group, a hexyl group and a cyclohexyl group And alkyl groups such as 1-ethylpropyl group, 1-methylpropyl group and 1,2-dimethylpropyl group.
  • alkyl groups may have a substituent, and the substituent is not particularly limited, and as the alkyl group having 1 to 6 carbon atoms having a substituent, for example, hydroxyethyl group, hydroxypropyl group, Examples thereof include hydroxybutyl group, 2-sulfoethyl group, carboxyethyl group, cyanoethyl group, methoxyethyl group, ethoxyethyl group, butoxyethyl group, trifluoromethyl group, pentafluoroethyl group, phenylmethyl group and the like.
  • the phenyl group or the benzyl group may have a substituent, and the substituent is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group and isopropyl Group, butyl group, t-butyl group, (C1 to C5) alkyl group such as pentyl group, fluorine atom, halogen atom such as chlorine atom, bromine atom or iodine atom, sulfonic acid group, methoxy group, ethoxy group, propoxy group (C1 to C6) alkoxy groups such as butoxy, t-butoxy and hexyloxy; hydroxy (C1 to C5) alkyl groups such as hydroxyethyl and hydroxypropyl; methoxyethyl, ethoxyethyl and ethoxypropyl Groups, (C1-C5) alkoxy (C1-C5) alkyl groups, (C1-C5) alk
  • R 1b to R 4b in the formula (3) a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted phenyl group, or an unsubstituted benzyl group is preferable.
  • examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a pentyl group, a cyclopentyl group, a hexyl group and a cyclohexyl group And alkyl groups such as.
  • These alkyl groups may have a substituent, and the substituent is not particularly limited, and examples of the alkyl group having 1 to 6 carbon atoms having a substituent include hydroxyethyl and hydroxypropyl.
  • Examples of the halogen atom in R 5b to R 17b of the formula (3) include fluorine, chlorine, bromine and iodine.
  • the amino group in R 17b of Formula (3) may have a substituent, and the substituent includes, for example, an alkyl group having 1 to 6 carbon atoms, a phenyl group or a benzyl group, and these are further substituted It may have a group, and the substituent is not particularly limited, and as the alkyl group having 1 to 6 carbon atoms having a substituent, for example, hydroxyethyl, hydroxypropyl, hydroxybutyl, 2-sulfoethyl Groups, carboxyethyl group, cyanoethyl group, methoxyethyl group, ethoxyethyl group, butoxyethyl group, trifluoromethyl group, pentafluoroethyl group and the like.
  • the substituent includes, for example, an alkyl group having 1 to 6 carbon atoms, a phenyl group or a benzyl group, and these are further substituted It may have a group, and the
  • examples of the substituent include a (C1 to C5) alkyl group such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group and pentyl group, fluorine atom, chlorine A halogen atom such as an atom, a bromine atom and an iodine atom, a sulfonic acid group, a sulfonic acid group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a t-butoxy group and a hexyloxy group, and a (C1-C6) alkoxy group; Hydroxy (C1-C5) alkyl group such as hydroxypropyl group; (C1-C5) alkoxy (C1-C5) alkyl group such as methoxyethyl group, ethoxyethyl
  • R 5b to R 16b in the formula (3) a hydrogen atom, a chlorine atom, or an unsubstituted alkyl group having 1 to 6 carbon atoms is preferable, and R 17b is preferably a hydrogen atom or an amino group.
  • Triarylmethane compound of the present invention may, for example, obtained by a known synthesis method described in Yutaka Hosoda al, issued by Gihodo Co. "Theoretical production Dye Chemistry” (781-787 pages), X - is chlorine anion It can also be synthesized by purchasing a commercially available product, adding the corresponding salt or acid, and performing salt exchange.
  • a compound in which X ⁇ is a chloride anion is a reaction solvent (eg, water, methanol, ethanol, isopropanol, acetone, N, N-dimethylformamide) And water-soluble polar solvents such as N-methyl-2-pyrrolidone (hereinafter abbreviated as NMP), which may be used alone or in combination, and the corresponding salts or
  • NMP N-methyl-2-pyrrolidone
  • the acid can be added by about 0.5 to 3 equivalents, stirred at a predetermined temperature (for example, 0 to 100 ° C.), easily synthesized, and obtained by filtering the precipitated crystals.
  • triarylmethane compounds represented by the formula (2) are shown in Table 1 below, and specific examples of the triarylmethane compounds represented by the formula (3) are shown in Table 2 below, but the present invention It is not limited.
  • Tables 1 and 2 for the substituent R, Me is methyl, Et is ethyl, Ph is phenyl, Bz is benzyl, CF 3 is trifluoromethyl, n-Bu is normal Sec-Bu represents a secondary butyl group, i-Pr represents an isopropyl group, and CyHex represents a cyclohexyl group.
  • X - when X - is ⁇ , it represents a tristrifluoromethanesulfonyl methide anion, and when it is a ⁇ , it represents a bistrifluoromethanesulfonyl imide anion.
  • the triarylmethane compound of the present invention is used as an oil-based dye composition, or a coloring composition such as various paints, water-based inks, oil-based inks, inks for inkjets, inks for color filters as an aqueous dye composition.
  • Oily dye compositions and aqueous dye compositions are used, for example, for colored materials such as plain paper, coated paper, plastic films, plastic substrates and the like.
  • various printing methods such as offset printing, letterpress printing, flexographic printing, ink jet printing, or coating methods using a spin coater, roll coater or the like can be mentioned.
  • the oily or aqueous dye compositions according to the invention comprise the triarylmethane compounds according to the invention and, in the case of oily dye compositions, an oil-soluble organic solvent, and in the case of aqueous dyes, an aqueous medium.
  • the triarylmethane compound of the present invention is preferably contained in an amount of 0.2 to 40% by weight, more preferably 0.5 to 20% by weight.
  • a coloring material other than the above-mentioned formula (1) may be added as needed for the purpose of adjusting the hue and the like.
  • coloring materials examples include water-soluble dyes such as acid dyes, reactive dyes, direct dyes, cationic dyes and basic dyes, oil-soluble dyes such as disperse dyes and solvent dyes, organic pigments, carbon black and the like. And added in a state of being dissolved or dispersed in a solvent.
  • the aqueous dye composition of the present invention can be prepared by dispersing the triarylmethane compound of the formula (1) in an aqueous medium.
  • Aqueous media include water or water soluble organic solvents.
  • the water-soluble organic solvent include alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, t-butanol, pentanol and benzyl alcohol; ethylene ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, polyethylene Polyhydric alcohols such as glycol, polypropylene glycol, glycerin, trimethylolpropane, 1,3-pentanediol and 1,5-pentanediol; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, Triethylene glycol monoethyl ether, triethylene glycol
  • the oil-based dye composition of the present invention can be prepared by dissolving or dispersing the triarylmethane compound of the above formula (1) in at least one or more oil-soluble organic solvents.
  • the oil-soluble organic solvent for example, alcohols such as ethanol, pentanol, octanol, cyclohexanol, benzyl alcohol and tetrafluoropropanol; ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol mono Glycol derivatives such as ethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, triethylene glycol monoethyl ether, ethylene glycol diacetate, propylene glycol diacetate; ketones such as methyl ethyl ketone and cyclohexanone; butyl phenyl ether, benzyl
  • Dispersants used in the oil-based dye composition include sodium dodecylbenzene sulfonate, sodium lauryl acid, formalin condensate of naphthalene sulfonic acid, formalin condensate of alkyl naphthalene sulfonic acid, formalin condensate of creosote oil sulfonic acid, poly Well-known anionic surfactants such as ammonium salt of oxyethylene alkyl ether sulfate, ammonium salt of polyoxyethylene alkyl phenyl ether sulfate, polyoxyalkyl ether phosphate ester salt, etc., vinyl naphthalene derivative, fat of ⁇ , ⁇ -ethylenically unsaturated carboxylic acid Alcohol ester etc., styrene, styrene derivative, acrylic acid, acrylic acid derivative, methacrylic acid, methacrylic acid derivative, maleic acid, maleic acid derivative, maleic anhydride,
  • nonionic surfactants and silicones such as polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, copolymer of ethylene oxide and propylene oxide, etc. If necessary, known antifoaming agents based on acetylene may be added during and / or after pigment dispersion.
  • Examples of the method of dispersing the pigment into fine particles include a method using a sand mill (beads mill), a roll mill, a ball mill, a paint shaker, an ultrasonic disperser, a microfluidizer, etc., among which sand mills (bead mills) are preferred.
  • a sand mill beads mill
  • the dye composition of the present invention may contain, as other additives, surface conditioners, preservatives, fungicides, pH adjusters and the like.
  • Surface conditioners include polysiloxane or polydimethylsiloxane surfactants; preservatives and fungicides include sodium dehydroacetate, sodium benzoate, sodium pyridinethione-1-oxide, zinc pyridinethione-1-oxide And an amine salt of 1,2-benzisothiazolin-3-one, 1-benzisothiazolin-3-one and the like, and as a pH adjuster, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, Examples thereof include tertiary amines such as triethanolamine, diethanolamine, dimethylethanolamine, diethylethanolamine and the like, and these can be added as necessary.
  • oil-based or aqueous dye composition of the present invention for the purpose of improving the fixability of the dye to the colored material, a polyamide based, polyurethane based, polyester compatible with the medium in the composition within the necessary range. It is preferable to contain a system, epoxy resin or polyacrylic resin. Further, in order to improve the fixing property, monomers, oligomers, polymerization initiators and the like having an ethylenically unsaturated group may be contained within the necessary range.
  • the oily or aqueous dye composition of the present invention can be prepared by dissolving, dispersing or mixing the above-mentioned components in a solvent.
  • Example 1 (Synthesis of Compound No. 1a in Table 1) Dissolve 2 parts of BasicBlue 7 (made by Tokyo Chemical Industry Co., Ltd., decomposition temperature: 217 ° C.) of the following formula (100) in 150 parts of water and, while stirring, add 30 parts of acetonitrile and cesium salt of tristrifluoromethanesulfonium methide 2.1. A solution in which parts were dissolved was added. After stirring for 3 hours, precipitated crystals were collected by filtration, washed with water and dried to obtain 1.5 parts of blue crystals (triarylmethane compound of the present invention). Decomposition temperature: 256 ° C
  • Example 2 Synthesis of Compound No. 2a in Table 1
  • Two parts of BasicBlue 7 of the following formula (100) were dissolved in 150 parts of water, and a solution of 1.2 parts of potassium salt of bistrifluoromethanesulfonium imide in 10 parts of water was added while stirring. After stirring for 3 hours, the precipitated crystals were collected by filtration, washed with water and dried to obtain 0.7 parts of blue crystals (the triarylmethane compound of the present invention).
  • Decomposition temperature 240 ° C
  • Example 3 Preparation of Oily Dye Composition and Dye Colored Material
  • 10 parts of tetrafluoropropanol the compound No. 1 obtained in the above example was used.
  • Compound No. 1a Each 0.5 part of 2a was dissolved to prepare an oily dye composition.
  • the obtained oily dye composition was spin-coated on a polycarbonate substrate and dried at 80 ° C. for 30 minutes to prepare a dye-colored material.
  • the comparative example 1 in the following Table 5 and Table 9 represents the test result of what prepared dye coloring matter similarly using BasicBlue7 of following formula (100).
  • Moisture and heat resistance test 1 The dye-colored material obtained by the above method was left to stand in a constant temperature and humidity chamber at 85 ° C. and 85% RH for 40 hours.
  • the dye colored materials before and after the test were measured for L value, a value and b value with a C light source as a standard light with a spectrophotometer and a viewing angle of 2 degrees as standard light, and the color difference was determined from the following formula. The smaller the color difference is, the smaller the change in hue is.
  • Color difference [(pre-test L value-post-test L value) 2 + (pre-test a value-post-test a value) 2 + (pre-test b value-post-test b value) 2 ] 1/2 Measured values of colorimetry and color differences in the moisture resistance test are shown in Tables 3 to 6 below.
  • the dye colored body of Comparative Example 1 before and after the test shows a very large value of 22.7
  • the dye colored body of the present invention has a color difference of 1.4 and 1 It shows a very small value of .6, and it can be seen that the heat and humidity resistance is extremely excellent.
  • the dye-colored product obtained by the above method was left in hot water at 70 ° C. for 5 minutes.
  • the dye colored materials before and after the test were measured for L value, a value and b value with a C light source as a standard light with a spectrophotometer and a viewing angle of 2 degrees as standard light, and the color difference was determined from the following formula. The smaller the color difference is, the smaller the change in hue is, and thus the better.
  • Color difference [(pre-test L value-post-test L value) 2 + (pre-test a value-post-test a value) 2 + (pre-test b value-post-test b value) 2 ] 1/2 Measured values of colorimetry and color differences in the water resistance test are shown in Tables 7 to 10 below.
  • Example 5 Preparation of Oily Dye Composition and Dye Colored Material
  • 10 parts of tetrafluoropropanol the compound No. 1 obtained in Example 4 was used.
  • An oil dye composition was prepared by dissolving 0.5 parts of 5a.
  • the obtained oily dye composition was spin-coated on a polycarbonate substrate and dried at 80 ° C. for 30 minutes to prepare a dye-colored material.
  • the comparative example 2 in the following Table 12 represents the evaluation result of what prepared dye coloring matter similarly using BasicBlue26 of said Formula (101).
  • Moisture and heat resistance test 2 The test method is the same as moist heat resistance test 1.
  • the colorimetric measurement values and color differences are shown in Tables 11 to 13 below.
  • Water resistance test 2 The test method is the same as water resistance test 1. Measured values of colorimetry and color differences are shown in Tables 14 to 16 below.
  • Example 6 (Synthesis of Compound No. 45a in Table 1) A cesium salt of tristrifluoromethanesulfonium methide is dissolved in a mixed solution of 2 parts of DMF and 12 parts of methanol while dissolving 2 parts of a dye of the following formula (102) in a mixed solution of 30 parts of water and 75 parts of methanol while stirring. A solution of 48 parts was added. After heating and stirring for 3 hours at 60 ° C., the precipitated crystals were collected by filtration, washed with water and dried to obtain 1.3 parts of blue crystals (triarylmethane compound of the present invention). Decomposition temperature: 262 ° C
  • Example 7 (Synthesis of Compound No. 57a in Table 1) A cesium salt of tristrifluoromethanesulfonium methide is dissolved in a mixed solution of 2 parts of DMF and 12 parts of methanol while dissolving 2.5 parts of a dye of the following formula (103) in a mixed solution of 2 parts of water and 38 parts of methanol while stirring. A solution of 2.87 parts dissolved was added. After heating and stirring for 3 hours at 60 ° C., the precipitated crystals were collected by filtration, washed with water and dried to obtain 2.8 parts of blue crystals (triarylmethane compound of the present invention). Decomposition temperature: 269 ° C
  • Example 8 (Synthesis of Compound No. 69a in Table 1) A cesium salt of tristrifluoromethanesulfonium methide is dissolved in a mixed solution of 3 parts of DMF and 25 parts of methanol while dissolving 3 parts of the dye of the following formula (104) in a mixed solution of 10 parts of water and 53 parts of methanol while stirring. A solution of 94 parts was added. After heating and stirring for 3 hours at 60 ° C., the precipitated crystals were collected by filtration, washed with water and dried to obtain 3.5 parts of blue crystals (triarylmethane compound of the present invention). Decomposition temperature: 267 ° C
  • Example 9 (Synthesis of Compound No. 1b in Table 2) In 50 parts of water, 1 part of malachite green oxalate of the following formula (105) was dissolved in 50 parts of water, and 2 parts of a cesium salt of tristrifluoromethanesulfonium methide was dissolved in 5 parts of DMF. The solution was added. After stirring for 3 hours, the precipitated crystals were collected by filtration, washed with water and dried to obtain 0.5 parts of dark green crystals (the triarylmethane compound of the present invention). Decomposition temperature: 190 ° C
  • Example 10 (synthesis of compound No. 3b in Table 2) In 500 parts of water was dissolved 5 parts of BasicBlue 1 (decomposition temperature: 190 ° C.) of the following formula (106), and a solution in which 2 parts of a cesium salt of tristrifluoromethanesulfonium methide was dissolved in 10 parts of DMF was added while stirring. . After stirring for 3 hours, the precipitated crystals were collected by filtration, washed with water and dried to obtain 0.7 parts of blue crystals (the triarylmethane compound of the present invention). Decomposition temperature: 230 ° C
  • Example 11 (synthesis of compound No. 5b in Table 2) In 500 parts of water, 5 parts of BasicViolet 3 (decomposition temperature: 205 ° C.) of the following formula (107) was dissolved, and a solution in which 1 part of a cesium salt of tristrifluoromethanesulfonium methide was dissolved in 10 parts of DMF was added while stirring. . After stirring for 3 hours, the precipitated crystals were collected by filtration, washed with water and dried to obtain 1.2 parts of purple crystals (triarylmethane compound of the present invention). Decomposition temperature: 240 ° C
  • Example 12 Preparation of Oily Dye Composition and Dye Colored Material
  • 10 parts of tetrafluoropropanol the compound No. 1 obtained in each of the above examples was used.
  • Compound No. 1b. 3b the compound No.
  • An oil dye composition was prepared by dissolving 0.5 parts of 5b.
  • the obtained oily dye composition was spin-coated on a polycarbonate substrate and dried at 80 ° C. for 30 minutes to prepare a dye-colored material.
  • Comparative Example 3 described in Tables 17 and 18 below is malachite green oxalate of the following Formula (105), Comparative Example 4 is BasicBlue 1 of the following Formula (106), and Comparative Example 5 is the following Formula (107)
  • the dye-colored bodies were similarly prepared using Basic Violet 3 of the above).
  • the dye-colored product obtained by the above method was left in warm water at 70 ° C. for 30 seconds.
  • the dye colored materials before and after the test were measured for L value, a value and b value with a C light source as a standard light with a spectrophotometer and a viewing angle of 2 degrees as standard light, and the color difference was determined from the following formula. The smaller the color difference is, the smaller the change in hue is, and thus the better.
  • Color difference [(pre-test L value-post-test L value) 2 + (pre-test a value-post-test a value) 2 + (pre-test b value-post-test b value) 2 ] 1/2 Measured values of colorimetry and color differences in the water resistance test are shown in Tables 17 to 23 below.
  • Example 13 (synthesis of compound No. 53b in Table 2) In a mixed solution of 200 parts of water and 120 parts of methanol, 2.31 parts of a dye of the following formula (108) is dissolved, and 2.30 parts of a cesium salt of tristrifluoromethanesulfonium methide is dissolved in 4.2 parts of DMF while stirring. The added solution was added. After stirring for 3 hours, precipitated crystals were collected by filtration, washed with water and dried to obtain 3.64 parts of blue crystals (Compound No. 53b). Decomposition temperature: 231 ° C
  • Example 14 (synthesis of compound No. 21b in Table 2) Dissolve 3.1 parts of the dye of the following formula (109) in a mixed solution of 150 parts of water and 72 parts of methanol, add cesium in tristrifluoromethanesulfonium methide to a mixed solution of 6.3 parts of DMF and 16 parts of methanol while stirring. A solution of 3.55 parts salt was added. After heating and stirring for 3 hours at 40 ° C., the precipitated crystals were collected by filtration, washed with water and dried to obtain 1.63 parts of blue crystals (Compound No. 21b). Decomposition temperature: 234 ° C
  • Example 15 (Synthesis of Compound No. 33b in Table 2) Dissolve 1.0 part of a dye of the following formula (110) in a mixed solution of 100 parts of water and 40 parts of methanol, add cesium in tristrifluoromethanesulfonium methide to a mixed solution of 3.2 parts of DMF and 8 parts of methanol while stirring A solution of 1.31 parts of salt was added. After heating and stirring for 3 hours at 30 ° C., the precipitated crystals were collected by filtration, washed with water and dried to obtain 0.98 parts of blue crystals (Compound No. 33b). Decomposition temperature: 232 ° C
  • Example 16 (synthesis of compound No. 69b in Table 2) Dissolve 1.0 part of the dye of the following formula (111) in a mixed solution of 100 parts of water and 40 parts of methanol, add cesium in tristrifluoromethanesulfonium methide to a mixed solution of 3.2 parts of DMF and 8 parts of methanol while stirring A solution of 0.65 parts salt was added. After heating and stirring for 3 hours at 40 ° C., the precipitated crystals were collected by filtration, washed with water and dried to obtain 0.73 parts of blue crystals (Compound No. 69b). Decomposition temperature: 277 ° C
  • the triarylmethane compound represented by the said Formula (1) of this invention is excellent in heat resistance from the comparison of the decomposition temperature, and the dye colored body has the characteristic excellent in heat-and-moisture resistance and water resistance. It has been revealed that the triarylmethane dyes of the present invention have high industrial value such as broadening the range of applications such as color filter inks and ink jet inks.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Optical Filters (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention porte sur une composition de colorant qui a une clarté élevée et une aptitude au développement de couleur élevée tout en présentant d'excellentes solidités telles que la résistance à la chaleur, la résistance à la chaleur humide et la résistance à l'eau. De façon spécifique, l'invention porte sur un composé de triarylméthane représenté par la formule (1) et une composition colorante à base huileuse ou aqueuse qui contient le composé triarylméthane. (Dans la formule (1), Ar1, Ar2 et Ar3 représentent chacun indépendamment un reste aromatique ayant un atome de carbone qui est lié à l'atome de carbone central ; et X- représente un anion bis(trifluorométhanesulfonyl)imide ou un anion tris(trifluorométhanesulfonyl)méthide).
PCT/JP2010/057160 2009-04-24 2010-04-22 Nouveau composé de triarylméthane WO2010123071A1 (fr)

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KR20170016367A (ko) 2014-05-30 2017-02-13 와코 쥰야꾸 고교 가부시키가이샤 트리페닐메탄계 착색조성물
JP2016124968A (ja) * 2014-12-26 2016-07-11 大日本印刷株式会社 トリアリールメタン化合物
WO2017170617A1 (fr) 2016-03-29 2017-10-05 和光純薬工業株式会社 Composé polymérisable polyfonctionnel et composition colorée

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JP5442004B2 (ja) 2014-03-12
TW201100358A (en) 2011-01-01

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