WO2019054436A1 - 重合性基を有する色素化合物及びそれをモノマー単位として含有する重合体 - Google Patents
重合性基を有する色素化合物及びそれをモノマー単位として含有する重合体 Download PDFInfo
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- WO2019054436A1 WO2019054436A1 PCT/JP2018/033941 JP2018033941W WO2019054436A1 WO 2019054436 A1 WO2019054436 A1 WO 2019054436A1 JP 2018033941 W JP2018033941 W JP 2018033941W WO 2019054436 A1 WO2019054436 A1 WO 2019054436A1
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- compound
- polymerizable
- exemplified compound
- alkyl group
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- 0 *C(C(C1=O)=CC=C2Oc(cccc3)c3N2*)=NN1c1ccccc1 Chemical compound *C(C(C1=O)=CC=C2Oc(cccc3)c3N2*)=NN1c1ccccc1 0.000 description 1
- CGPBOMIJLSDIAC-KQWKDUQZSA-N CC(C)(C)C(/C1=C/C=C2\Oc(cccc3)c3N2C)=NN(C)C1=O Chemical compound CC(C)(C)C(/C1=C/C=C2\Oc(cccc3)c3N2C)=NN(C)C1=O CGPBOMIJLSDIAC-KQWKDUQZSA-N 0.000 description 1
- XLVCAFITQRWVBS-TWHCVMCKSA-N CCCCN1c(cccc2)c2O/C1=C\C=C(\C(C(C)(C)C)=NN1c(cc2)ccc2NCCC(C)CC(C)(C)C)/C1=O Chemical compound CCCCN1c(cccc2)c2O/C1=C\C=C(\C(C(C)(C)C)=NN1c(cc2)ccc2NCCC(C)CC(C)(C)C)/C1=O XLVCAFITQRWVBS-TWHCVMCKSA-N 0.000 description 1
- NJVBJKRFBHMDOI-IJWBNVHUSA-N CCCCN1c(cccc2)c2O/C1=C\C=C(\C(C(C)(C)C)=NN1c(ccc(NCCC(C)CC(C)(C)C)c2)c2NCCC(C)CC(C)(C)C)/C1=O Chemical compound CCCCN1c(cccc2)c2O/C1=C\C=C(\C(C(C)(C)C)=NN1c(ccc(NCCC(C)CC(C)(C)C)c2)c2NCCC(C)CC(C)(C)C)/C1=O NJVBJKRFBHMDOI-IJWBNVHUSA-N 0.000 description 1
- XOCHNCJEMNHCDD-IHNODLEPSA-N CCCCN1c(cccc2)c2O/C1=C\C=C(\C(N(CC)C(CCO)=O)=NN1c(cc2)ccc2N(CCC(C)CC(C)(C)C)C(CCO)=O)/C1=O Chemical compound CCCCN1c(cccc2)c2O/C1=C\C=C(\C(N(CC)C(CCO)=O)=NN1c(cc2)ccc2N(CCC(C)CC(C)(C)C)C(CCO)=O)/C1=O XOCHNCJEMNHCDD-IHNODLEPSA-N 0.000 description 1
- OIRJKPVKKINNHA-FMIHOGGJSA-N CCCCN1c(cccc2)c2O/C1=C\C=C(\C(c(cc1)ccc1N(CCC(C)CC(C)(C)C)C(C(C)(CO)CO)=O)=NN1c(cc2)ccc2N(CCC(C)CC(C)(C)C)C(C(C)(CO)CO)=O)/C1=O Chemical compound CCCCN1c(cccc2)c2O/C1=C\C=C(\C(c(cc1)ccc1N(CCC(C)CC(C)(C)C)C(C(C)(CO)CO)=O)=NN1c(cc2)ccc2N(CCC(C)CC(C)(C)C)C(C(C)(CO)CO)=O)/C1=O OIRJKPVKKINNHA-FMIHOGGJSA-N 0.000 description 1
- OLMGGFFEVVCSRY-XWIKOFCXSA-N CCCCc1nnc2[n]1N=C(CCC)/C2=C\C=C1/Oc2cc(CCCNCC)ccc2N1CNCC Chemical compound CCCCc1nnc2[n]1N=C(CCC)/C2=C\C=C1/Oc2cc(CCCNCC)ccc2N1CNCC OLMGGFFEVVCSRY-XWIKOFCXSA-N 0.000 description 1
Classifications
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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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/105—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a methine or polymethine dye
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
-
- 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
- C09B23/10—The polymethine chain containing an even number of >CH- groups
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
Definitions
- the present invention relates to a dye compound having a polymerizable group and a polymer containing the same as a monomer unit.
- pyrazolone dyes and pyrazoloazole dyes have been synthesized so far, their usefulness has been confirmed, and they are widely used.
- the present invention has been widely applied to various applications such as photographic light-sensitive materials, heat-sensitive transfer recording materials, color toners, optical recording media, and inkjets.
- the performance required for the above-mentioned application includes, for example, favorable spectral characteristics for color reproduction, solubility in a desired organic solvent, large molecular absorption coefficient, and fastness to light and heat. They are robust to various chemicals, easy to synthesize, and safe.
- Patent Documents 1 to 6 many pyrazolone dyes and pyrazoloazole dyes have been proposed for the purpose of improving them, for example, improvement of light and heat fastness has been proposed (Patent Documents 1 to 6), but solubility Further improvement is desired because
- Patent Document 7 proposes the improvement of the solvent solubility, but in the above-mentioned application, it is applied in the form of a solution or a dispersion, but it may be applied to other organic solvents in order to be soluble in a desired organic solvent. In many cases, it becomes soluble, and as a result, the solvent resistance after coating becomes weak.
- patent document 9 is proposed about improvement of solvent resistance by providing a polymeric group, it is inadequate, the further improvement is desired and examination is necessary.
- the present invention has been made in view of the above problems and circumstances, and the problem to be solved is a novel polymer which is excellent in solubility in organic solvents and is excellent in heat resistance, light resistance and solvent resistance. It is an object of the present invention to provide a dye compound having a polymerizable group. By having excellent solubility in an organic solvent, it can be easily made into various application forms, and by giving a polymerizable group, a dye having excellent solvent resistance can be obtained by performing heat or light treatment. Another object of the present invention is to provide a polymer containing a novel dye group having a polymerizable group as a monomer unit.
- dye compound which has a polymeric group which has a structure represented by following General formula (1).
- R ' represents an alkyl group.
- L 1 represents an alkylene group or an arylene group.
- R 4 represents a single bond, an alkylene group or an arylene group.
- R 5 , R 6 and R 7 each represent a hydrogen atom, an alkyl group, a carboxy group, an alkyloxycarbonyl group or an aryl group.
- X 1 represents an oxygen atom or N—Y, and R 1 and X 1 may form a ring.
- Y represents a substituent.
- X 2 represents -O-, -S-, -Se-, -NR 8 -or -CR 9 R 10- .
- R 11 to R 16 each represent a hydrogen atom or a substituent, and R 11 and R 12 may combine with each other to form a ring.
- n represents an integer of 1 to 3. ] 2.
- R 1 , R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 or Y At least one of R 1 , R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 or Y.
- the dye compound having a polymerizable group according to item 1 or 2 wherein the dye compound represented by the general formula (1) has a structure represented by the following general formula (2).
- L 1 represents an alkylene group or an arylene group.
- R 4 represents a single bond, an alkylene group or an arylene group.
- R 5 , R 6 and R 7 each represent a hydrogen atom, an alkyl group, a carboxy group, an alkyloxycarbonyl group or an aryl group. At least two of R 1 , R 2 , R 3 or R 17 have a polymerizable group, or at least one of R 1 , R 2 , R 3 or R 17 has a plurality of the above-mentioned polymerizable groups.
- n represents an integer of 1 to 3.
- n1 represents an integer of 0 to 4; ] 4.
- R 18 represents an alkyl group or an aryl group.
- R 5 , R 6 and R 7 each represent a hydrogen atom, an alkyl group, a carboxy group, an alkyloxycarbonyl group or an aryl group.
- Each of R 20 , R 21 and R 22 independently represents an alkyl group, an aryl group, a hydrogen atom or —OCOR 23 .
- R 23 represents an alkyl group or an aryl group.
- R ' represents an alkyl group.
- L 1 represents an alkylene group or an arylene group.
- R 4 represents a single bond, an alkylene group or an arylene group.
- At least two of R 2, R 3, R 17 or R 19 have a polymerizable group, or at least one of R 2 , R 3 , R 17 or R 19 has a plurality of polymerizable groups.
- n represents an integer of 1 to 3.
- n2 represents an integer of 0 to 4;
- n3 represents an integer of 0 to 5; ] 5.
- a polymer comprising, as a monomer unit, the dye compound having a polymerizable group according to any one of items 1 to 4.
- the above means of the present invention it is possible to provide a dye compound having a novel polymerizable group, which enables a polymer excellent in solubility and excellent in heat resistance, light resistance and solvent resistance. Moreover, the polymer which contains the pigment
- the mechanism for expressing the effect of the present invention or the mechanism of action is not clear but is presumed as follows.
- the dye compound having a polymerizable group of the present invention is confirmed to have improved heat resistance by having an amide group at the bonding portion. Further, the solubility is considered to be improved by substituting a hydrogen atom on the nitrogen of the amide group with an alkyl group or the like.
- the dye compound having a polymerizable group of the present invention is characterized by having a structure represented by the following general formula (1).
- the dye compound having a structure represented by the following general formula (1) preferably has a structure represented by the following general formula (2) or the following general formula (3).
- L 1 represents an alkylene group or an arylene group.
- R 4 represents a single bond, an alkylene group or an arylene group.
- R 5 , R 6 and R 7 each represent a hydrogen atom, an alkyl group, a carboxy group, an alkyloxycarbonyl group or an aryl group.
- n represents an integer of 1 to 3;
- L 1 represented by General Formula (1), (2) or (3) represents a linking group and represents an alkylene group or an arylene group. These may or may not have a substituent.
- Examples of the substituent of these linking groups represented by L 1 in the general formulas (1), (2) or (3) include a halogen atom, a cyano group and an alkyl group. However, the present invention is not limited to these.
- R 'represented by General formula (1), (2) or (3) represents an alkyl group.
- the alkyl group include a methyl group, an ethyl group, a propyl group and a butyl group. These may or may not have a substituent. However, the present invention is not limited to these.
- R 5 , R 6 and R 7 represented by the general formula (1), (2) or (3) each represent a hydrogen atom, an alkyl group, a carboxy group, an alkyloxycarbonyl group or an aryl group.
- the alkyl group include a methyl group, an ethyl group and a butyl group
- the present invention is not limited to these.
- an alkyl group is exemplified by, for example, a methyl group And ethyl, propyl, iso-propyl, tert-butyl, pentyl, hexyl, octyl, dodecyl, tridecyl, tetradecyl and pentadecyl groups.
- a phenyl group, a naphthyl group, etc. are mentioned, for example.
- heterocyclic group examples include pyridine ring, pyrazole ring, imidazole ring, pyrazine ring, pyrimidine ring, triazine ring, thiazole ring, oxazole ring, quinoline ring, benzothiazole ring, benzooxazole ring and the like.
- pyridine ring examples include pyridine ring, pyrazole ring, imidazole ring, pyrazine ring, pyrimidine ring, triazine ring, thiazole ring, oxazole ring, quinoline ring, benzothiazole ring, benzooxazole ring and the like.
- thiazole ring imidazole ring
- pyrazine ring pyrimidine ring
- triazine ring examples include thiazole ring, oxazole ring, quinoline ring, benzothiazole ring, benzooxazo
- the alkyl group is, for example, methyl group, ethyl group, propyl group, iso-propyl group, tert-butyl group, pentyl group, hexyl group And 2-ethylhexyl group, 3,5,5-trimethylhexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group and the like.
- an aryl group a phenyl group, a naphthyl group, etc. are mentioned, for example.
- heterocyclic ring examples include a pyridine ring, a pyrazole ring, an imidazole ring, a pyrazine ring, a pyrimidine ring, a triazine ring, a thiazole ring, an oxazole ring, a quinoline ring, a benzothiazole ring, a benzooxazole ring and the like.
- the present invention is not limited to these.
- R 19 represented by the general formula (3) represents -CO-CR 20
- R 21 R 22 and R 20 R 21 and R 22 each independently represent an alkyl group, an aryl group, a carboxy group or an alkyloxycarbonyl group, a hydrogen atom or an -OCOR 23,
- R 23 represents an alkyl group, an aryl group.
- X 1 represented by General Formula (1) represents an oxygen atom or N—Y, and when N—Y, R 1 and X 1 may form a ring.
- Examples of the ring to be formed include structures represented by the following formulas (4), (5), (6) and (7). However, the present invention is not limited to these.
- R 2 ′ represents an alkyl group, an aryl group, a heterocyclic group and a polymerizable group
- R 24 , R 25 , R 26 and R 27 each represent a hydrogen atom
- It represents an alkyl group, an aryl group, a heterocyclic group and a polymerizable group, and may further have a substituent.
- * Represents a linking site.
- X 2 represented by the general formula (1) represents -O-, -S-, -Se-, -NR 8 -or -CR 9 R 10- , preferably -O- or -S- And most preferably -O-.
- R 8 represented by the general formula (1) represents a hydrogen atom, an alkyl group, or a polymerizable group, and the same groups as R 1 , R 2 and R 3 can be mentioned, but the same substitution as R 3
- the group is preferable in the synthesis and may further have a substituent.
- Examples of the substituent of these groups represented by R 8 in the general formula (1) include a halogen atom, a cyano group and an alkyl group. However, the present invention is not limited to these.
- R 9 and R 10 represented by the general formula (1) represent a hydrogen atom, an alkyl group or a polymerizable group, and examples of the polymerizable group include the same groups as R 1 , R 2 and R 3 above, and an alkyl group Examples thereof include a methyl group, an ethyl group and a butyl group, but a hydrogen atom and an alkyl group having 1 to 3 carbon atoms are preferable, and may further have a substituent.
- Examples of the substituent of these groups represented by R 9 and R 10 in the general formula (1) include a halogen atom, a cyano group and an alkyl group. However, the present invention is not limited to these.
- the substituent for Z in the general formula (1) is not particularly limited, and examples thereof include an alkyl group, an alkoxy group, an alkoxycarbonyl group, an aryl group, a cyano group or a halogen atom.
- the halogen atom includes fluorine, chlorine, bromine and iodine.
- Examples of the alkyl group include ethyl group, propyl group, iso-propyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group and the like.
- alkoxy group examples include methoxy group, ethoxy group, propoxy group, iso-propoxy group, butoxy group, tert-butoxy group, iso-butoxy group, pentoxy group and the like.
- alkoxycarbonyl group examples include a methoxycarbonyl group, an ethoxycarbonyl group and the like.
- aryl group include, for example, a phenyl group and a naphthyl group, preferably an alkyl group and an alkoxy group, and more preferably a hydrogen atom or an alkyl group.
- R 11 and CR 12 may be bonded to each other to form a ring, and examples thereof include a cyclopentane ring, a cyclohexane ring, a benzene ring, a pyridine ring, a naphthalene ring and the like, preferably a benzene ring, and further It may have a substituent.
- the present invention is not limited to these.
- the dye compound having a polymerizable group represented by the general formula (1), (2) or (3) may be a copolymer with another monomer, and the monomer is not particularly limited, but it is acrylic or styrenic And vinyl. However, the present invention is not limited to these.
- the structural unit contained in the polymer containing the dye compound having a polymerizable group represented by the general formula (1), (2) or (3) of the present invention as a monomer unit is not particularly limited, but It is represented by the general formula (8). However, the present invention is not limited to these. Further, since the polymer having the structural unit represented by the general formula (8) is linked by a covalent bond, the heat resistance becomes good, and the compatibility with other polymers can be improved and mixed.
- Dye 1 represents the dye structural unit of the dye compound according to the present invention
- M 1 represents another monomer structural unit
- n 1 represents the composition of the dye compound according to the present invention
- n 2 Represents the composition of the other monomer. * Represents a linking site.
- the polymerization initiator for polymerizing the above polymerizable monomer is not particularly limited, and examples thereof include tert-butylperoxy-iso-butyrate, 2,5-dimethyl-2,5-bis (benzoyldioxy) hexane, 1 , 4-Bis [ ⁇ - (tert-butyldioxy) -iso-propoxy] benzene, di-tert-butylperoxide, 2,5-dimethyl-2,5-bis (tert-butyldioxy) hexene hydroperoxide, ⁇ - (iso -Propylphenyl) -iso-propyl hydroperoxide, 2,5-bis (hydroperoxy) -2,5-dimethylhexane, tert-butyl hydroperoxide, 1,1-bis (tert-butyldioxy) -3,3,5 -Trimethylcyclohexane, butyl-4,4-bis (tert-
- the molar ratio of n1: n2 is preferably in the range of 100: 0 to 5:95. More preferably, it is in the range of 90:10 to 10:90.
- the dye compound having a polymerizable group according to the present invention is preferably dissolved in the following solvent, and can dissolve the dye compound having a polymerizable group, and it does not cause hindrance in performance maintenance or processing.
- Solvents preferably used for the coloring compound having a polymerizable group of the present invention include aromatic solvents such as toluene and xylene, acetate solvents such as ethyl acetate and propylene glycol monomethyl ether acetate, acetone, methyl ethyl ketone and methyl isobutyl Ketone solvents such as ketone, nitrogen-containing solvents such as N, N-dimethylformamide, N-methyl-2-pyrrolidone, halogenated hydrocarbon solvents such as dichloromethane and 1,1,2-trichloroethane, methanol, ethanol, Examples thereof include alcohol solvents such as trifluoroethanol and butanol, and ether solvents such as tetrahydro
- the coloring compound having a polymerizable group of the present invention may contain various additives depending on the purpose and application.
- aqueous resin non-aqueous resin, anionic surfactant, cationic surfactant, nonionic surfactant, amphoteric surfactant, surface tension regulator, viscosity regulator, non-resistance regulator, defoaming agent Agents, fungicides and the like.
- the dye compound having a polymerizable group of the present invention can be processed in a state of being dissolved or dispersed in a solvent containing the above additive.
- the amount of the additive in the solvent and the amount of the dye compound having a polymerizable group may be appropriately determined depending on the purpose.
- the processing method is not particularly limited, but can be performed by a conventionally known method such as kneading method, bar coat, blade coat, microgravure coat, knife coat, dip coat and the like.
- the exemplified compound 113 was synthesized in the same manner as in Example 3 except that the compound 5A was used instead of the compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 226 was synthesized in the same manner as in Example 3 except that Compound 6A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 109 was synthesized in the same manner as in Example 3 except that Compound 7A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 151 was synthesized in the same manner as in Example 3 except that Compound 8A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 153 was synthesized in the same manner as in Example 3 except that Compound 9A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 117 was synthesized in the same manner as in Example 3 except that Compound 10A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- the exemplified compound 118 was synthesized by the same method as that of Example 3 except that the compound 11A was used instead of the compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- the exemplified compound 187 was synthesized in the same manner as in Example 3 except that the compound 12A was used instead of the compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- the exemplified compound 188 was synthesized in the same manner as in Example 3 except that the compound 13A was used instead of the compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- the exemplified compound 233 was synthesized in the same manner as in Example 3 except that the compound 14A was used instead of the compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- the exemplified compound 326 was synthesized in the same manner as in Example 3 except that the compound 15A was used instead of the compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 327 was synthesized in the same manner as in Example 3 except that Compound 16A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 336 was synthesized in the same manner as in Example 3 except that Compound 17A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 303 was synthesized in the same manner as in Example 3 except that Compound 18A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 330 was synthesized by the same method as in Example 3 except that Compound 19A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- the exemplified compound 271 was synthesized in the same manner as in Example 3 except that the compound 20A was used instead of the compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 4 was synthesized in the same manner as in Example 3 except that Compound 21A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 12 was synthesized in the same manner as in Example 3 except that Compound 22A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 13 was synthesized in the same manner as in Example 3 except that Compound 23A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- the exemplified compound 32 was synthesized in the same manner as in Example 3 except that the compound 24A was used instead of the compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 40 was synthesized in the same manner as in Example 3 except that Compound 25A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 47 was synthesized in the same manner as in Example 3 except that Compound 26A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 57 was synthesized in the same manner as in Example 3 except that Compound 27A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 69 was synthesized in the same manner as in Example 3 except that Compound 28A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 73 was synthesized in the same manner as in Example 3 except that Compound 29A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- the exemplified compound 75 was synthesized in the same manner as in Example 3 except that the compound 30A was used instead of the compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 81 was synthesized in the same manner as in Example 3 except that Compound 31A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 89 was synthesized in the same manner as in Example 3 except that Compound 32A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 121 was synthesized in the same manner as in Example 3 except that Compound 33A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 135 was synthesized in the same manner as in Example 3 except that Compound 34A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 140 was synthesized in the same manner as in Example 3 except that Compound 35A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 164 was synthesized in the same manner as in Example 3 except that Compound 36A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 182 was synthesized by the same method as in Example 3 except that Compound 37A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 208 was synthesized by the same method as in Example 3 except that Compound 38A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 221 was synthesized in the same manner as in Example 3 except that Compound 39A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 249 was synthesized in the same manner as in Example 3 except that Compound 40A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 255 was synthesized in the same manner as in Example 3 except that Compound 41A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- the exemplified compound 278 was synthesized in the same manner as in Example 3 except that the compound 42A was used instead of the compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- the exemplified compound 289 was synthesized in the same manner as in Example 3 except that the compound 43A was used instead of the compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 307 was synthesized in the same manner as in Example 3 except that Compound 44A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 311 was synthesized in the same manner as in Example 3 except that Compound 45A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 316 was synthesized in the same manner as in Example 3 except that Compound 46A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- the exemplified compound 342 was synthesized in the same manner as in Example 3 except that Compound 47A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 349 was synthesized in the same manner as in Example 3 except that Compound 48A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 353 was synthesized by the same method as in Example 3 except that Compound 49A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 365 was synthesized in the same manner as in Example 3 except that Compound 50A was used instead of Compound 4A used in Example 3.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 102 was synthesized by the same method as in Example 50 except that Compound 52A was used instead of Compound 29A used in Example 50.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 115 was synthesized in the same manner as in Example 50 except that Compound 53A was used instead of Compound 29A used in Example 50.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Exemplified compound 129 was synthesized in the same manner as in Example 50 except that Compound 54A was used instead of Compound 29A used in Example 50.
- the structure was identified by MASS, 1 H-NMR and IR spectra.
- Example Compound 113 was used instead of Example Compound 112 used in Example 54.
- Comparative Example 1 Synthesis of Comparative Compound A The following Comparative Compound A described in JP-A-2015-147825 was synthesized.
- Comparative Example 2 Synthesis of Comparative Compound B The following Comparative Compound B described in JP-A-2015-147825 was synthesized.
- Comparative Example 3 Synthesis of Comparative Compound C The following Comparative Compound C described in JP-A-2006-16564 was synthesized.
- Comparative Example 4 Synthesis of Copolymer (3) A copolymer was prepared by the same method as in Example 54 except that 2.5 g of the above-mentioned Comparative Compound A was used instead of the exemplified compound 112 used in Example 54. 2.4 g of (3) was obtained.
- Comparative Example 5 Synthesis of Copolymer (4) A copolymer was prepared by the same method as in Example 54 except that 2.5 g of the above-mentioned Comparative Compound B was used instead of the exemplified compound 112 used in Example 54. 2.4 g of (4) was obtained.
- Example 56 The pigment solution having a polymerizable group of the present invention and azobisisobutyronitrile as a photopolymerization initiator are dissolved in a 1: 1 mixed solution of toluene and methyl ethyl ketone (MEK), and the obtained colored solution is made 150 ⁇ m thick A wet film thickness of 60 ⁇ m was applied and dried on synthetic paper (Yupo FPG-150: made by Oji Yuka Co., Ltd.) respectively, and then exposed with a high pressure mercury lamp (3 kW, 200 mJ / cm 2 ) to prepare a coated sample . By adjusting the dye concentration of each solution, a coated sample having a reflection density of 1 at the maximum absorption wavelength was produced (hereinafter referred to as a coated film A), and performance evaluation was performed.
- a coated film A a coated film A
- Example 57 The dye compound having a polymerizable group of the present invention is dissolved in a 1: 1 mixed solution of toluene and MEK, and the obtained colored solution is synthetic paper having a thickness of 150 ⁇ m (Yupo FPG-150: manufactured by Oji Oil Co., Ltd.
- the coated sample was prepared by coating and drying each on a wet film thickness of 60 ⁇ m. By adjusting the dye concentration of each solution, a coated sample having a reflection density of 1 at the maximum absorption wavelength was produced (hereinafter referred to as a coated film B), and performance evaluation was performed.
- coated samples were produced in the same manner as in Examples 56 and 57.
- a coated sample was produced in the same manner as in Example 57.
- solvent resistance (%) (maximum absorption wavelength concentration of a immersion sample / maximum absorption wavelength concentration of a non-immersion sample) x 100, and evaluated four steps based on the following evaluation criteria. : solvent resistance 90% or more ⁇ : solvent resistance 80% or more and less than 90% ⁇ : solvent resistance 60% or more and less than 80% ⁇ : less than 60% solvent resistance ⁇ or more Above no problem.
- the dye compound of the present invention has high solubility in an organic solvent and a monomer thereof It was confirmed that the polymer contained as a unit is excellent in light resistance and heat resistance. In addition, we succeeded in significantly improving the solvent resistance by introducing one or more polymerizable groups.
- the pigment dye more excellent with respect to light resistance, heat resistance, and solvent resistance was able to be provided by this invention compared with the conventional pyrazolone pigment and pyrazoloazole pigment.
- the dye compound having a polymerizable group of the present invention can enable a polymer excellent in solubility and excellent in heat resistance, light resistance and solvent resistance. By having excellent solubility in organic solvents, various application forms can be easily achieved.
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Abstract
Description
R1、R2及びR3は、それぞれ独立に、-R4-NR´-CO-L1-(OCO-R5C=CR6R7)n、-L1-NR´CO-R5C=CR6R7及び-NR´CO-R5C=CR6R7の中から選ばれる重合性基、アルキル基、それぞれ置換基を有しても良いアリール基又は複素環基を表す。R´は、アルキル基を表す。L1は、アルキレン基又はアリーレン基を表す。R4は、単結合、アルキレン基又はアリーレン基を表す。R5、R6及びR7は、水素原子、アルキル基、カルボキシ基、アルキルオキシカルボニル基又はアリール基を表す。
R8、R9及びR10は、-R4-NR´-CO-L1-(OCO-R5C=CR6R7)n、-L1-NR´CO-R5C=CR6R7及び-NR´CO-R5C=CR6R7の中から選ばれる重合性基、アルキル基、アリール基又は複素環基を表す。
R11~R16は、水素原子又は置換基を表し、R11とR12は互いに結合して環を形成しても良い。
2.前記一般式(1)において、前記R1、R2、R3、R8、R9、R10、R11、R12、R13、R14、R15、R16若しくはYの少なくとも二つに前記重合性基を有するか、又は前記R1、R2、R3、R8、R9、R10、R11、R12、R13、R14、R15、R16若しくはYの少なくとも一つに複数の前記重合性基を有することを特徴とする第1項に記載の重合性基を有する色素化合物。
R1、R2、R3及びR17は、それぞれ独立に、-R4-NR´-CO-L1-(OCO-R5C=CR6R7)n、-L1-NR´CO-R5C=CR6R7及び-NR´CO-R5C=CR6R7の中から選ばれる重合性基、アルキル基、それぞれ置換基を有しても良いアリール基又は複素環基を表す。R´は、アルキル基を表す。L1は、アルキレン基又はアリーレン基を表す。R4は、単結合、アルキレン基又はアリーレン基を表す。R5、R6及びR7は、水素原子、アルキル基、カルボキシ基、アルキルオキシカルボニル基又はアリール基を表す。R1、R2、R3若しくはR17の少なくとも二つに重合性基を有するか、又はR1、R2、R3、若しくはR17の少なくとも一つに複数の前記重合性基を有する。
4.前記一般式(2)で表される重合性基を有する色素化合物が下記一般式(3)で表される構造を有することを特徴とする第3項に記載の重合性基を有する色素化合物。
R18は、アルキル基又はアリール基を表す。R19、は、-CO-L1-(OCO-R5C=CR6R7)n、-CO-R5C=CR6R7又は-CO-CR20R21R22を表す。
R5、R6、R7は、水素原子、アルキル基、カルボキシ基、アルキルオキシカルボニル基又はアリール基を表す。R20、R21、R22は、それぞれ独立に、アルキル基、アリール基、水素原子、-OCOR23を表す。R23は、アルキル基又はアリール基を表す。
R3は、-L1-NR´CO-R5C=CR6R7で表される重合性基、アルキル基、それぞれ置換基を有しても良いアリール基又は水素原子を表す。
5.第1項から第4項までのいずれか一項に記載の重合性基を有する色素化合物をモノマー単位として含有する重合体。
一般式(4)、(5)、(6)及び(7)においてR2´で表される、アルキル基、アリール基、複素環基及び重合性基としては前記一般式(1)、(2)及び(3)で表されるR1、R2及びR3と同様の基を挙げることができる。
上記重合性モノマーを重合させるための重合開始剤としては特に限定されないが、例えばtert-ブチルペルオキシ-iso-ブタレ-ト、2,5-ジメチル-2,5-ビス(ベンゾイルジオキシ)ヘキサン、1,4-ビス[α-(tert-ブチルジオキシ)-iso-プロポキシ]ベンゼン、ジ-tert-ブチルペルオキシド、2,5-ジメチル-2,5-ビス(tert-ブチルジオキシ)ヘキセンヒドロペルオキシド、α-(iso-プロピルフェニル)-iso-プロピルヒドロペルオキシド、2,5-ビス(ヒドロペルオキシ)-2,5-ジメチルヘキサン、tert-ブチルヒドロペルオキシド、1,1-ビス(tert-ブチルジオキシ)-3,3,5-トリメチルシクロヘキサン、ブチル-4,4-ビス(tert-ブチルジオキシ)バレレート、シクロヘキサノンペルオキシド、2,2′,5,5′-テトラ(tert-ブチルペルオキシカルボニル)ベンゾフェノン、3,3′,4,4′-テトラ(tert-ブチルペルオキシカルボニル)ベンゾフェノン、3,3′,4,4′-テトラ(tert-アミルペルオキシカルボニル)ベンゾフェノン、3,3′,4,4′-テトラ(tert-ヘキシルペルオキシカルボニル)ベンゾフェノン、3,3′-ビス(tert-ブチルペルオキシカルボニル)-4,4′-ジカルボキシベンゾフェノン、tert-ブチルペルオキシベンゾエート、ジ-tert-ブチルジペルオキシイソフタレート等の有機過酸化物や、9,10-アンスラキノン、1-クロロアンスラキノン、2-クロロアンスラキノン、オクタメチルアンスラキノン、1,2-ベンズアンスラキノン等のキノン類や、ベンゾインメチル、ベンゾインエチルエーテル、α-メチルベンゾイン、α-フェニルベンゾイン等のベンゾイン誘導体や、トリフェニルホスホニウム クロリド、トリフェニルホスホニウム ブロミド、トリ(4-メトキシフェニル)ホスホニウムテトラフルオロボレート、トリ(p-メトキシフェニル)ホスホニウム ヘキサフルオロホスホネート、トリ(4-エトキシフェニル)ホスホニウム テトラフルオロボレート等のトリアリールホスホニウム塩化合物やジフェニルヨードニウムクロライド、ジフェニルヨードニウムトリフルオロメタンスルホネート、ジフェニルヨードニウムメシレート、ジフェニルヨードニウムメシレート、ジフェニルヨードニウムトシレート、ジフェニルヨードニウムブロミド、ジフェニルヨードニウムテトラフルオロボレート、ジフェニルヨードニウムヘキサフルオロホスフェート、ジフェニルヨードニウムヘキサフルオロアンチモネート、ジフェニルヨードニウムヘキサフルオロアルセネート、ビス(p-tert-ブチルフェニル)ヨードニウムヘキサフルオロホスフェート、ビス(p-tert-ブチルフェニル)ヨードニウムメシレート、ビス(p-tert-ブチルフェニル)ヨードニウムトシレート、ビス(p-tert-ブチルフェニル)ヨードニウムトリフルオロメタンスルホネート、ビス(p-tert-ブチルフェニル)ヨードニウムテトラフルオロボレート、ビス(p-tert-ブチルフェニル)ヨードニウムクロリド、ビス(p-クロロフェニル)ヨードニウムクロライド、ビス(p-クロロフェニル)ヨードニウムテトラフルオロボレート等のジアリールヨードニウム塩化合物や鉄アレーン錯体等を使用することができる。しかし、本発明はこれらに限定されるものではない。
特開2015-147825号公報記載の下記比較化合物Aを合成した。
特開2015-147825号公報記載の下記比較化合物Bを合成した。
特開2006-16564号公報記載の下記比較化合物Cを合成した。
実施例54で使用した例示化合物112の代わりに、2.5gの上記比較化合物Aを使用した以外は実施例54と同様の方法により共重合体(3)を2.4g得た。
実施例54で使用した例示化合物112の代わりに、2.5gの上記比較化合物Bを使用した以外は実施例54と同様の方法により共重合体(4)を2.4g得た。
本発明の重合性基を有する色素化合物、それをモノマー単位として含有する重合体(本発明の共重合体)及び比較(比較化合物及び比較の共重合体)のそれぞれをメタノール、酢酸エチル、トルエン、エチレングリコール及びN-メチル-2-ピロリドン(NMP)に、3質量%濃度になる様に溶解させ、その溶解性を目視評価で以下の評価基準に基づいて4段階評価した。その結果を表I及びIIに示す。
◎:直ちに完溶
○:室温で一晩振とうすることで完全に溶解している。
△:加温することで完全に溶解している。
×:加温しても溶け残りが存在している。
○以上であることが望ましい。
(実施例56)
本発明の重合性基を有する色素化合物と、光重合開始剤としてアゾビスイソブチロニトリルとをトルエンとメチルエチルケトン(MEK)の1:1混合溶液に溶解させ、得られた着色溶液を150μmの厚さを有する合成紙(ユポFPG-150:王子油化社製)上に、それぞれウェット膜厚60μmで塗布・乾燥後、高圧水銀灯で露光し(3kW、200mJ/cm2)、塗布試料を作製した。それぞれの溶液の色素濃度を調整することにより、最大吸収波長の反射濃度が1となる塗布試料を作製(以下、塗布膜A)し、性能評価を実施した。
本発明の重合性基を有する色素化合物を、トルエンとMEKの1:1混合溶液に溶解させ、得られた着色溶液を150μmの厚さを有する合成紙(ユポFPG-150:王子油化社製)上に、それぞれウェット膜厚60μmで塗布・乾燥し、塗布試料を作製した。それぞれの溶液の色素濃度を調整することにより、最大吸収波長の反射濃度が1となる塗布試料を作製(以下、塗布膜B)し、性能評価を実施した。
塗布膜Aと実施例56と同様な方法で作製した比較色素(比較化合物A~C)及び実施例57と同様な方法で作成した共重合体(1)~(4)を塗布した試料について、キセノンフェードメーターにて120時間曝射した後、未曝射試料の可視領域の極大吸収波長における反射スペクトル濃度からの、残存率を評価した。その結果を表III及びIVに示す。
◎:耐光性が95% 以上
○:耐光性が90% 以上、95% 未満
△:耐光性が80% 以上、90% 未満
×:耐光性が80% 未満
○以上であれば実用上問題ない。
塗布膜Aと実施例56と同様な方法で作製した比較色素(比較化合物A~C)及び実施例57と同様な方法で作成した共重合体(1)~(4)を塗布した試料について、77℃、10%RH以下の条件下7日間保存し、保存開始前後の濃度比からの、残存率を評価した。その結果を表V及びVIに示す。
◎:耐熱性が95% 以上
○:耐熱性が80% 以上、95% 未満
△:耐熱性が60% 以上、80% 未満
×:耐熱性が60% 未満
○以上であれば実用上問題ない。
得られた塗布膜A、塗布膜B及びそれぞれの比較(比較化合物及び比較の共重合体)のそれぞれを、メタノール、酢酸エチル、トルエン、エチレングリコール及びNMPに25℃、30分間浸漬させた。この処理前後の試料について、浸漬前の可視領域の極大吸収波長における反射スペクトル濃度からの、残存率を評価し、表VII及び表VIIIに示す。
◎:耐溶剤性が90%以上
○:耐溶剤性が80%以上、90%未満
△:耐溶剤性が60%以上、80%未満
×:耐溶剤性が60%未満
○以上であれば実用上問題ない。
Claims (5)
- 下記一般式(1)で表される構造を有する重合性基を有する色素化合物。
R1、R2及びR3は、それぞれ独立に、-R4-NR´-CO-L1-(OCO-R5C=CR6R7)n、-L1-NR´CO-R5C=CR6R7及び-NR´CO-R5C=CR6R7の中から選ばれる重合性基、アルキル基、それぞれ置換基を有しても良いアリール基又は複素環基を表す。R´は、アルキル基を表す。L1は、アルキレン基又はアリーレン基を表す。R4は、単結合、アルキレン基又はアリーレン基を表す。R5、R6及びR7は、水素原子、アルキル基、カルボキシ基、アルキルオキシカルボニル基又はアリール基を表す。
X1は、酸素原子又はN-Yを表し、R1とX1で環を形成しても良い。Yは、置換基を表す。
X2は、-O-、-S-、-Se-、-NR8-又は-CR9R10-を表す。
R8、R9及びR10は、-R4-NR´-CO-L1-(OCO-R5C=CR6R7)n、-L1-NR´CO-R5C=CR6R7及び-NR´CO-R5C=CR6R7の中から選ばれる重合性基、アルキル基、アリール基又は複素環基を表す。
Zは、環を形成するのに必要な原子群であって、-CR11=CR12-又は-CR13R14-CR15R16-を表す。
R11~R16は、水素原子又は置換基を表し、R11とR12は互いに結合して環を形成しても良い。
R1、R2、R3、R8、R9、R10、R11、R12、R13、R14、R15、R16又はYの少なくとも一つは、-R4-NR´-CO-L1-(OCO-R5C=CR6R7)n、-L1-NR´CO-R5C=CR6R7及び-NR´CO-R5C=CR6R7の中から選ばれる重合性基を有す。
nは、1~3の整数を表す。〕 - 前記一般式(1)において、前記R1、R2、R3、R8、R9、R10、R11、R12、R13、R14、R15、R16若しくはYの少なくとも二つに前記重合性基を有するか、又は前記R1、R2、R3、R8、R9、R10、R11、R12、R13、R14、R15、R16若しくはYの少なくとも一つに複数の前記重合性基を有することを特徴とする請求項1に記載の重合性基を有する色素化合物。
- 前記一般式(1)で表される色素化合物が下記一般式(2)で表される構造を有することを特徴とする請求項1又は請求項2に記載の重合性基を有する色素化合物。
R1、R2、R3及びR17は、それぞれ独立に、-R4-NR´-CO-L1-(OCO-R5C=CR6R7)n、-L1-NR´CO-R5C=CR6R7及び-NR´CO-R5C=CR6R7の中から選ばれる重合性基、アルキル基、それぞれ置換基を有しても良いアリール基又は複素環基を表す。R´は、アルキル基を表す。L1は、アルキレン基又はアリーレン基を表す。R4は、単結合、アルキレン基又はアリーレン基を表す。R5、R6及びR7は、水素原子、アルキル基、カルボキシ基、アルキルオキシカルボニル基又はアリール基を表す。R1、R2、R3若しくはR17の少なくとも二つに重合性基を有するか、又はR1、R2、R3、若しくはR17の少なくとも一つに複数の前記重合性基を有する。
nは、1~3の整数を表す。n1は、0~4の整数を表す。〕 - 前記一般式(2)で表される重合性基を有する色素化合物が下記一般式(3)で表される構造を有することを特徴とする請求項3に記載の重合性基を有する色素化合物。
R18は、アルキル基又はアリール基を表す。R19、は、-CO-L1-(OCO-R5C=CR6R7)n、-CO-R5C=CR6R7又は-CO-CR20R21R22を表す。
R5、R6、R7は、水素原子、アルキル基、カルボキシ基、アルキルオキシカルボニル基又はアリール基を表す。R20、R21、R22は、それぞれ独立に、アルキル基、アリール基、水素原子、-OCOR23を表す。R23は、アルキル基又はアリール基を表す。
R2及びR17は、それぞれ独立に、-R4-NR´-CO-L1-(OCO-R5C=CR6R7)n、-L1-NR´CO-R5C=CR6R7及び-NR´CO-R5C=CR6R7の中から選ばれる重合性基、アルキル基、それぞれ置換基を有しても良いアリール基又は複素環基を表す。
R3は、-L1-NR´CO-R5C=CR6R7で表される重合性基、アルキル基、それぞれ置換基を有しても良いアリール基又は水素原子を表す。
R´は、アルキル基を表す。L1はアルキレン基又はアリーレン基を表す。R4は、単結合、アルキレン基又はアリーレン基を表す。
R2、R3、R17若しくはR19の少なくとも二つに重合性基を有するか、又はR2、R3、R17、若しくはR19の少なくとも一つに複数の重合性基を有する。
nは、1~3の整数を表す。n2は、0~4の整数を表す。n3は0~5の整数を表す。〕 - 請求項1から請求項4までのいずれか一項に記載の重合性基を有する色素化合物をモノマー単位として含有する重合体。
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0643586A (ja) * | 1992-07-24 | 1994-02-18 | Konica Corp | ハロゲン化銀写真感光材料 |
JP2008176176A (ja) * | 2007-01-22 | 2008-07-31 | Konica Minolta Business Technologies Inc | 電子写真用トナー |
JP2015147825A (ja) * | 2014-02-05 | 2015-08-20 | コニカミノルタケミカル株式会社 | 重合性基を有する新規色素化合物 |
JP2016001276A (ja) * | 2014-06-12 | 2016-01-07 | Jsr株式会社 | カラーフィルタ用着色組成物、カラーフィルタ用着色硬化膜、表示素子及びカラーフィルタ用着色剤分散液 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09226259A (ja) | 1995-12-20 | 1997-09-02 | Konica Corp | 感熱転写記録材料及び感熱転写記録方法 |
JPH1062978A (ja) | 1996-08-21 | 1998-03-06 | Konica Corp | 光開始剤、光重合組成物、ラジカル発生方法、平版印刷版作成用感光性材料及び平版印刷版の作成方法 |
JP3650865B2 (ja) | 1997-03-28 | 2005-05-25 | コニカミノルタホールディングス株式会社 | 感熱転写記録材料 |
JP3736221B2 (ja) | 1998-08-28 | 2006-01-18 | 凸版印刷株式会社 | カラーフィルターおよびこれを備えた液晶表示装置 |
DE10111731A1 (de) * | 2001-03-09 | 2002-09-12 | Bayer Ag | Verfahren zur Herstellung von unsymmetrischen Methinfarbstoffen |
JP4821095B2 (ja) | 2004-07-05 | 2011-11-24 | コニカミノルタホールディングス株式会社 | ピラゾロン色素 |
JP4238184B2 (ja) | 2004-07-05 | 2009-03-11 | 大日本印刷株式会社 | 感熱転写記録材料及び感熱転写記録方法 |
DE102004036609A1 (de) * | 2004-07-28 | 2006-03-23 | Wella Ag | Kationische Pyrazolonfarbstoffe, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Färbemittel für Keratinfasern |
JP4617774B2 (ja) | 2004-08-26 | 2011-01-26 | コニカミノルタホールディングス株式会社 | カラートナー及びカラーフィルター |
JP5130630B2 (ja) | 2005-03-28 | 2013-01-30 | コニカミノルタホールディングス株式会社 | 着色組成物、インクジェット記録液、インクジェット記録方法、カラートナー、カラーフィルター及び金属キレート色素 |
JP5215538B2 (ja) * | 2006-06-30 | 2013-06-19 | 富士フイルム株式会社 | アゾ色素、着色組成物、感熱転写記録用インクシート、感熱転写記録方法、カラートナー、インクジェット用インクおよびカラーフィルタ |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0643586A (ja) * | 1992-07-24 | 1994-02-18 | Konica Corp | ハロゲン化銀写真感光材料 |
JP2008176176A (ja) * | 2007-01-22 | 2008-07-31 | Konica Minolta Business Technologies Inc | 電子写真用トナー |
JP2015147825A (ja) * | 2014-02-05 | 2015-08-20 | コニカミノルタケミカル株式会社 | 重合性基を有する新規色素化合物 |
JP2016001276A (ja) * | 2014-06-12 | 2016-01-07 | Jsr株式会社 | カラーフィルタ用着色組成物、カラーフィルタ用着色硬化膜、表示素子及びカラーフィルタ用着色剤分散液 |
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