Classifications

• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
  • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
  • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
• • 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
  • C09B47/00—Porphines; Azaporphines
  • C09B47/04—Phthalocyanines abbreviation: Pc
  • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
  • C09B47/18—Obtaining compounds having oxygen atoms directly bound to the phthalocyanine 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
  • C09B67/006—Preparation of organic pigments
• • 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
• • 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

Definitions

• the present disclosure relates to fluorophthalocyanine compounds, coloring compositions, and inkjet inks.
• Fluorinated phthalocyanine compounds are used in various applications such as colorants and materials for various optical filters.
• Patent Document 1 describes a compound that is a fluorophthalocyanine compound with a specific structure and that is applied to a near-infrared absorbing material.
• Patent Document 2 describes a colored curable composition containing a phthalocyanine compound that is soluble in an organic solvent and has a main absorption in the range of 680 nm to 800 nm in a chloroform solvent.
• Patent Document 3 describes a phthalocyanine compound having a specific structure, which is applied to a photosensitive resin composition used for forming a color filter.
• Patent Document 4 describes a resin composition for forming a light selective transmission filter containing a fluorophthalocyanine compound having a specific structure.
• Patent Document 1 JP-A-4-345861
• Patent Document 2 JP-A-2013-182214
• Patent Document 3 Korean Patent Publication No. 10-2016-0060542
• Patent Document 4 JP-A-2014-6361
• An object of one embodiment of the present disclosure is to provide a fluorophthalocyanine compound having excellent light resistance and moisture resistance.
• Another embodiment of the present disclosure aims to provide a coloring composition or inkjet ink containing the fluorophthalocyanine compound.
• a fluorophthalocyanine compound represented by the following formula (1) represented by the following formula (1).
• a fluorophthalocyanine compound represented by the following formula (1) A fluorophthalocyanine compound represented by the following formula (1).
• M represents a metal atom or an oxide of a metal atom
• R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 and R 108 each independently It represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
• R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 and R 108 are all —CH 2 CH 2 (OCH 2 CH 2 ) p R 1 or not all —(C q H 2q )NR 2 R 3 .
• R 1 represents an acyl group or an alkoxy group having 1 to 4 carbon atoms
• R 2 and R 3 each independently represent an alkyl group having 1 to 4 carbon atoms
• p is an integer of 0 to 5
• q is an integer from 1 to 6;
• R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 and R 108 are each independently an unsubstituted alkyl group or the following formula ( 2), provided that a set A of R101 and R102 , a set B of R103 and R104 , a set C of R105 and R106 , and R107 and R108
• the fluorinated phthalocyanine compound according to ⁇ 1> wherein at least one of the two groups in each group consisting of Group D with and represents an unsubstituted alkyl group.
• R 201 , R 202 , R 203 , R 204 and R 205 each independently represent a hydrogen atom or a monovalent substituent. However, at least one of R 201 , R 202 , R 203 , R 204 and R 205 represents a group represented by the following formula (3).
• R301 represents a hydrogen atom or a monovalent substituent
• L3 represents a single bond or a divalent linking group.
• each set consisting of a set A of R 101 and R 102 , a set B of R 103 and R 104 , a set C of R 105 and R 106 , and a set D of R 107 and R 108
• ⁇ 4> A colored composition comprising the fluorophthalocyanine compound according to any one of ⁇ 1> to ⁇ 3>.
• ⁇ 5> An inkjet ink containing the fluorophthalocyanine compound according to any one of ⁇ 1> to ⁇ 3>.
• a fluorophthalocyanine compound with excellent light resistance and moisture resistance is provided.
• a coloring composition or inkjet ink comprising the fluorinated phthalocyanine compound.
• FIG. 10 is a diagram showing a print pattern used for evaluation in Examples.
• the numerical range indicated using “ ⁇ ” means a range that includes the numerical values before and after " ⁇ " as lower and upper limits, respectively.
• upper or lower limits described in a certain numerical range may be replaced with upper or lower limits of other numerical ranges described step by step.
• upper or lower limits described in a certain numerical range may be replaced with values shown in Examples.
• the amount of each component in the composition when referring to the amount of each component in the composition, if there are multiple substances corresponding to each component in the composition, unless otherwise specified, the amount of the multiple components present in the composition is means total volume.
• notations that do not specify substitution and unsubstituted include those that do not have substituents as well as those that have substituents. , include not only unsubstituted hydrocarbon groups but also substituted hydrocarbon groups.
• substituent S means the substituent group shown below.
• the substituent S includes halogen atoms (e.g., fluorine atom, chlorine atom, bromine atom, etc.), alkyl groups (linear, branched and cyclic), alkenyl groups, alkynyl groups, aryl groups, hetero Cyclic group, cyano group, silyl group, hydroxy group, nitro group, amino group, alkylamino group, alkoxy group, aryloxy group, acylamino group, arylamino group, ureido group, sulfamoylamino group, alkylthio group, arylthio group , alkoxycarbonylamino group, sulfonamide group, carbamoyl group, sulfamoyl group, sulfonyl group, alkoxycarbonyl group, heterocyclic
• the fluorophthalocyanine compound represented by formula (1) (hereinafter also referred to as a specific fluorophthalocyanine compound) is excellent in light resistance and moisture resistance is not clear, but it has a fluorophthalocyanine skeleton and At least one of the two groups in each set consisting of A, set B, set C, and set D (i.e., a group such as R 101 that bonds to the ⁇ -position of the phthalocyanine ring via an oxygen atom) is substituted or It is presumed that the unsubstituted alkyl group appropriately relaxes the association and aggregation state due to intermolecular interaction, and efficiently acts to dissipate light energy and reduce the affinity for water.
• the coloring composition and the inkjet ink according to the present disclosure contain the specific fluorophthalocyanine compound, they are excellent in light resistance and moisture resistance.
• the appropriate relaxation of the association-aggregation state of the specific fluorophthalocyanine compound can contribute to excellent ejection stability when the specific fluorophthalocyanine compound is applied to an inkjet ink. Therefore, continuous printing can be stably performed by using an inkjet ink containing a specific fluorophthalocyanine compound.
• the phthalocyanine compounds described in Patent Documents 1 to 4 above are inferior to the specific fluorinated phthalocyanine compounds in both light resistance and moisture resistance. Inkjet inks to which these phthalocyanine compounds are applied also do not provide ejection stability.
• the fluorophthalocyanine compound (specific fluorophthalocyanine compound) represented by formula (1) is a novel fluorophthalocyanine compound.
• M represents a metal atom or an oxide of a metal atom
• R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 and R 108 each independently It represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
• R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 and R 108 are all —CH 2 CH 2 (OCH 2 CH 2 ) p R 1 or all —(C q H 2q ) NR 2 R 3 .
• R 1 represents an acyl group or an alkoxy group having 1 to 4 carbon atoms
• p is an integer of 0 to 5
• q is an integer of 1 to 6.
• M represents a metal atom or an oxide of a metal atom.
• the metal atoms include iron, magnesium, nickel, cobalt, copper, palladium, zinc, vanadium, titanium, indium, and tin.
• M is preferably copper, zinc, cobalt, nickel, iron, oxytitanium or oxyvanadium, more preferably copper, zinc or oxyvanadium.
• M is preferably zinc or copper.
• M is preferably zinc.
• one of the two groups in each set of set A, set B, set C and set D is a substituted or unsubstituted alkyl group and the other is a substituted or unsubstituted aryl group or substituted Alternatively, it may be an unsubstituted heterocyclic group, or both groups may be substituted or unsubstituted alkyl groups.
• one of the two groups in each of Group A, Group B, Group C and Group D is a substituted or unsubstituted alkyl group, and the other is a substituted or It is preferably an unsubstituted alkyl group or a substituted or unsubstituted aryl group, more preferably one is an unsubstituted alkyl group and the other is a substituted aryl group.
• two groups in each set of set A, set B, set C and set D may be a combination of the same groups in each group or a combination of different groups in each group.
• the two groups in each of Group A, Group B, Group C and Group D are preferably combinations of the same group.
• R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 or R 108 represents a substituted or unsubstituted alkyl group
• the alkyl chain in the alkyl group may be linear, branched or Although it may be cyclic, the alkyl chain is preferably linear from the viewpoint of further improving light resistance and moisture resistance.
• the substituted or unsubstituted alkyl group represented by R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 or R 108 is preferably an alkyl group having a total of 1 to 18 carbon atoms.
• An alkyl group having 1 to 12 carbon atoms is more preferable, an alkyl group having a total carbon number of 1 to 8 is more preferable, and an alkyl group having a total carbon number of 1 or 2 is particularly preferable.
• Alkyl groups also include cycloalkyl groups. Examples of alkyl groups include methyl, ethyl, propyl, butyl, hexyl, cyclohexyl, decyl, dodecyl, stearyl groups and the like.
• R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 or R 108 represents a substituted or unsubstituted alkyl group, from the viewpoint of further improving light resistance and moisture resistance,
• An unsubstituted alkyl group is preferable, an unsubstituted alkyl group having 1 to 8 carbon atoms is more preferable, and an unsubstituted alkyl group having 1 or 2 carbon atoms (ie, a methyl group or an ethyl group) is even more preferable.
• R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 or R 108 is a substituted alkyl group
• the substituent of the alkyl group is selected from substituents S, From the viewpoint of availability of raw materials, halogen atoms, alkoxy groups, amino alkenyl groups, alkynyl groups, aryl groups, heterocyclic groups, hydroxy groups, alkylamino groups, aryloxy groups, acylamino group, arylamino group, ureido group, sulfamoylamino group, alkylthio group, arylthio group, alkoxycarbonylamino group, sulfonamide group, carbamoyl group, sulfamoyl group, sulfonyl group, alkoxycarbonyl group, heterocyclicoxy group, acyloxy group , a carbamoyloxy group, a silyloxy
• the substituted or unsubstituted aryl group represented by R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 or R 108 is not particularly limited, and may be monocyclic or condensed ring. Alternatively, it may be an aryl group having a total carbon number of 6 to 18, or an aryl group having a total carbon number of 6 to 14.
• the substituted or unsubstituted aryl group represented by R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 or R 108 is an aryl group represented by the following formula (2). It is particularly preferred to have
• R 201 , R 202 , R 203 , R 204 and R 205 each independently represent a hydrogen atom or a monovalent substituent.
• R 201 , R 202 , R 203 , R 204 and R 205 are all hydrogen atoms, and one or two of R 201 , R 202 , R 203 , R 204 and R 205
• An embodiment in which one is a monovalent substituent is preferred. From the viewpoint of light resistance and moisture resistance, one or two of R 201 , R 202 , R 203 , R 204 and R 205 are more preferably monovalent substituents .
• R 205 is a monovalent substituent
• R 201 or R 205 and R 203 are monovalent substituents
• the monovalent substituent represented by R 201 , R 202 , R 203 , R 204 or R 205 is not particularly limited, and examples thereof include substituents selected from substituents S, halogen atoms, linear Alternatively, branched-chain alkyl groups, cyano groups, alkoxy groups, amino groups, alkoxycarbonyl groups, carboxy groups, and acyl groups are preferred, and among these, groups represented by the following formula (3) are more preferred.
• R301 represents a hydrogen atom or a monovalent substituent
• L3 represents a single bond or a divalent linking group.
• a divalent linking group can be mentioned.
• linking groups R each independently represent a hydrogen atom or a monovalent substituent.
• the monovalent substituents in R A , R B , and R C may have substituents such as substituent S.
• R A , R B , and R C are preferably each independently a hydrogen atom or a substituent S, and more preferably each independently a hydrogen atom or an alkyl group.
• L3 is preferably a single bond.
• the monovalent substituent represented by R 301 is not particularly limited and includes, for example, a substituent selected from the substituent S, preferably an alkyl group or an aryl group.
• a substituent selected from the substituent S preferably an alkyl group or an aryl group.
• a straight or branched chain alkyl group having 1 to 18 carbon atoms, or a phenyl group is more preferable, an alkyl group having 1 to 6 carbon atoms is more preferable, an alkyl group having 1 to 2 carbon atoms (methyl group, or ethyl group) is particularly preferred.
• the substituted or unsubstituted heterocyclic group represented by R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 or R 108 is preferably a heterocyclic group having a total of 2 to 12 carbon atoms, A heterocyclic group having a total of 3 to 8 carbon atoms is more preferred. Heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, and the like.
• the heterocyclic group may be either a saturated ring or an unsaturated ring, preferably a heteroaromatic ring.
• the number of ring members of the heterocyclic group is preferably 5 or 6, more preferably 6.
• the substituent of the substituted heterocyclic group is not particularly limited, and examples thereof include the substituent S.
• the group represented by the above-described formula (3) is preferably exemplified.
• one preferred embodiment of the specific fluorophthalocyanine compound is 107 and R 108 each independently represent an unsubstituted alkyl group or an aryl group represented by formula (2) above.
• R 201 , R 202 , R 203 , R 204 and R 205 represents the group represented by formula (3) above.
• Another preferred aspect of the specific fluorophthalocyanine compound is, from the viewpoint of improving light resistance and humidity resistance, Of the two groups in each set consisting of set B, set C of R 105 and R 106 , and set D of R 107 and R 108 , one group is an alkyl group having 1 to 2 carbon atoms and the other is a substituted or unsubstituted aryl group.
• the maximum absorption wavelength of the specific fluorophthalocyanine compound is preferably in the wavelength range of 630 nm to 690 nm, more preferably in the wavelength range of 640 nm to 680 nm, and even more preferably in the wavelength range of 650 nm to 670 nm.
• the molar extinction coefficient at the maximum absorption wavelength of the specific fluorophthalocyanine compound is 100,0 It is preferably 00 L/(mol ⁇ cm) or more, more preferably 120,000 L/(mol ⁇ cm) or more.
• the maximum absorption wavelength and molar absorption coefficient are the maximum absorption wavelength and molar absorption coefficient in the absorption spectrum of the solution of the fluorophthalocyanine compound, and are measured using a spectrophotometer.
• a specific measuring method is as follows. That is, for example, using ethyl acetate, chloroform, or dimethylformamide as a solvent, a solution having a concentration of 1 ⁇ 10 ⁇ 6 M is prepared, and the obtained solution is measured with a spectrophotometer (eg, UV-3100 manufactured by Shimadzu Corporation). using a quartz cell with an optical path length of 10 mm.
• Compound (G-2) is a mixture of isomers (G-2-1) to (G-2-4) shown in Table 1 below.
• the method for producing the specific fluorophthalocyanine compound is not particularly limited, and for example, it may be produced by referring to known methods. For example, it can be synthesized according to the method described in Japanese Patent No. 6054649. Specifically, for example, a specific fluorophthalocyanine compound can be produced by heating and stirring a difluorophthalonitrile having optional substituents at the 4- and 5-positions and an inorganic compound in an organic solvent.
• a specific fluorophthalocyanine compound can be suitably used as a coloring agent. Further, since the specific fluorophthalocyanine compound exhibits a hue (specifically, cyan to green), a colored composition containing the specific fluorophthalocyanine compound or an inkjet ink containing the fluorophthalocyanine compound according to the present disclosure It can be preferably used as.
• the coloring composition according to the present disclosure is not particularly limited as long as it contains the specific fluorophthalocyanine compound.
• the coloring composition according to the present disclosure contains the specific fluorophthalocyanine compound, and thus has excellent light resistance and moisture resistance.
• the properties of the coloring composition according to the present disclosure are not particularly limited, and for example, it may be liquid, solid, or semi-solid at 25°C.
• Components other than the specific fluorinated phthalocyanine compound (hereinafter also referred to as other components) contained in the coloring composition according to the present disclosure may be appropriately determined according to the application of the coloring composition.
• Applications of the colored composition according to the present disclosure include, for example, various inks, paints, dyes, colored resins, color masterbatches, colored resin pellets, and the like.
• coloring compositions include, for example, solvents, resins, coloring agents other than specific fluorophthalocyanine compounds, release agents, antioxidants, surfactants, various additions such as preservatives agents and the like.
• the content of the specific fluorophthalocyanine compound in the coloring composition according to the present disclosure may be appropriately determined according to the application of the coloring composition.
• the inkjet ink according to the present disclosure is not particularly limited as long as it contains a specific fluorophthalocyanine compound.
• the inkjet ink according to the present disclosure includes an ink in which a specific fluorophthalocyanine compound is dissolved and/or dispersed in a lipophilic medium or an aqueous medium.
• the inkjet ink according to the present disclosure contains the specific fluorophthalocyanine compound, it has excellent light resistance and moisture resistance, as well as excellent ejection stability.
• the inkjet ink according to the present disclosure contains a specific fluorophthalocyanine compound and a lipophilic medium or an aqueous medium, and optionally a coloring agent other than the fluorophthalocyanine compound according to the present disclosure and a drying inhibitor (wetting agent). , anti-fading agent, emulsion stabilizer, penetration accelerator, UV absorber, preservative, anti-mold agent, pH adjuster, surface tension adjuster, antifoaming agent, viscosity adjuster, dispersant, dispersion stabilizer, rust preventive agents, chelating agents, and other known additives.
• a drying inhibitor wetting agent
• the inkjet ink according to the present disclosure may be an ink that is cured by irradiation with active energy rays.
• a curable component e.g., a polymerizable compound, a polymerization initiator, an epoxy compound, a curing agent, etc.
• Colorants other than the fluorophthalocyanine compound according to the present disclosure, known additives, and the like are preferably included.
• the content of the fluorophthalocyanine compound according to the present disclosure in the inkjet ink according to the present disclosure may be appropriately determined according to the type of ink.
• the content of the fluorophthalocyanine compound according to the present disclosure is, for example, preferably 0.5% by mass to 8% by mass, more preferably 3% by mass to 6% by mass, relative to the total mass of the inkjet ink according to the present disclosure. % is more preferable.
• the compounds (G-1) to (G-6) shown below are the same as the compounds (G-1) to (G-6) given as specific examples of the specific fluorophthalocyanine compound described above. .
• this coarse particle dispersion was passed through a microfluidizer (manufactured by MICROFLUIDEX INC) five times at a pressure of 60 MPa to make fine particles. Further, the resulting emulsion was desolvated with a rotary evaporator until the odor of ethyl acetate disappeared.
• An ink was prepared by adding 140 g of diethylene glycol, 50 g of glycerin, 7 g of SURFYNOL® 465 (Air Products & Chemicals), and 900 mL of deionized water to the microemulsion of compound (G-1) thus obtained.
• Inkjet ink (2) was prepared in the same manner as for inkjet ink (1), except that any one of compounds (G-2) to (G-6) was used instead of compound (G-1). ⁇ (6) was obtained.
• the resulting printed sample was irradiated with xenon light (85000 lux) for 7 days using a weather meter (Atlas, Ci65), and the reflection density before and after irradiation with xenon light was 1.0.
• the reflection density of the solid image was measured using a reflection densitometer (manufactured by X-Rite, trade name: X-Rite i1Pro). Further, since the solid image had a reflection density of 1.0 before irradiation with xenon light, the compound residual rate (%) before and after irradiation with xenon light was calculated from the following formula. The higher the compound residual rate (%), the more excellent the light resistance of the fluorophthalocyanine compound contained in the print sample.

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• Dispersion Chemistry (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)
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• 2022
  • 2022-12-13 WO PCT/JP2022/045857 patent/WO2023136027A1/ja not_active Ceased
  • 2022-12-13 JP JP2023573915A patent/JP7785810B2/ja active Active

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