TW201130868A - Photocuring resin and dispersing agent using the same - Google Patents

Abstract

This invention provides a dispersing agent, which has high dispersibility, and the photocurability during film coating and the fitness to the substrate are high. As the dispersing agent in this invention, a photocurable resin is obtained by adding a compound (D) in which the same molecule has active hydrogens and tertiary amino groups after adding a compound (B) in which the same molecule has one or two hydroxyl groups and number average molecular weight is 300 to 5000 and a compound (C) in which the same molecule has two hydroxyl groups and two ethylene unsaturated groups to a diisocyanate compound (A).

Description

201130868 VI. Description of the Invention: [Technical Field] The present invention relates to a novel photocurable resin having a specific structure and a dispersing agent using the same. [Prior Art] Various dispersants have been used in the fields of paints, inks, and the like in order to improve the dispersibility of pigments, improve the storage stability of coatings, and the gloss of coating films. For example, in the patent document, a dispersing agent derived from a compound having at least one basic group containing a ring nitrogen is disclosed. In Patent Document 2, a polyisocyanate, an acrylate compound or a ring is disclosed. A dispersing agent for a reaction product obtained by reacting an oxygen compound and a cyclic compound, and Patent Document 3 discloses a photoresist composition for a color light-passing sheet using a specific dispersion resin as a dispersing agent. Further, in recent years, the industry has attempted to impart photocurability to the dispersant itself, and to improve compatibility with the photocurable adhesive, photocurability at the time of coating, and adhesion to the substrate. Patent Document 4 discloses a polyaminoformate resin-based photocurable coating material, and Patent Document 5 discloses a pigment obtained by reacting a (meth) acrylate compound with a monoamine compound. A dispersing agent, but the coating or dispersing agent is insufficient in photocurability or adhesion. [Patent Document 1] Japanese Patent Laid-Open Publication No. Hei No. Hei. No. Hei. No. Hei. 〇 丨 丨 丨 专利 专利 丨 丨 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 146 2011 Problem] An object of the present invention is to provide a dispersant having high dispersibility, high photocurability at the time of coating, and high adhesion to a substrate. [Means for Solving the Problems] The present invention achieves the above object by providing a photocurable resin which is one or two in the same molecule by addition of a diisocyanate compound (A). After compound (B) having a number of molecular weights of 300 to 5,000 and a compound having two hydroxyl groups and two ethylenically unsaturated groups in the same molecule, Michael has an active hydrogen in the same molecule. Obtained from the compound (D) of the tertiary amino group. Further, the present invention provides a photocurable resin obtained by further esterifying the photocurable resin with a polybasic acid anhydride (E). Further, the present invention achieves the above object by providing a dispersing agent containing the photocurable resin as an effective component. [Effects of the Invention] Since the photocurable resin of the present invention has excellent photocurability, the photocurability of the coating film using the photocurable resin as a dispersing agent as an active component and the adhesion to the substrate after photocuring Higher sex. [Embodiment] Hereinafter, the photocurable resin of the present invention and a dispersing agent using the same will be described in detail based on preferred embodiments. The photocurable resin of the present invention is obtained by reacting a diisocyanate compound 146899.doc 201130868 ethylenically unsaturated group compound (C), and the same addition of the same molecule has one or two hydroxyl groups in the same molecule. After the number average molecule 300~5_the compound (8) and the same molecule have #2 interesting C), the wheat may be added to the compound (D) having the active hydrogen and the tertiary amino group in the same molecule, and further, depending on the desired anhydride ( Ε) obtained by esterification. To be multivariate

The diisocyanate compound (Α) for obtaining the photocurable resin of the present invention may, for example, be 1,2-ethylidene diisocyanate, 1,4-tetramethylammonium isoester, i,6J. Hexamethylene diisocyanate, 2,2,4-xanthine Gongyi '6 ', methyl diisocyanate, 2,4,4-trimethyl-1,6-six-leaf Gong*^, An aliphatic diisocyanate such as cyanic acid S, 1,12-dodecane diisocyanate, or a di-isoisocyanate diether; cyclobutane-1,3-diisocyanurate, hexanide, '3' isocyanate, cyclohexene-1,4-diisocyanate, 2,2-; isocyanazin-1-methyl·cyclohexane, 2,6 diiso-acidic small methyl-ring Married, different Buddha _ diisocyanate vinegar, 2,5 winter (isocyanato fluorenyl) each methyl mountain 4-methyl bridge decalin, 3,5-bis-(isohalo acid fluorenyl) -8-mercapto-I,4-middle bridge-ten"naphthalene 1,5-bis(isocyanatomethyl)-4,7-fluorene bridge-hexahydro-segmentation, 2' bis(isocyanato Sulfhydryl)-4,7_曱 bridge-hexahydroindan, 1,6-bis(isocyanatomethyl 2/7-methyl bridge-hexahydro-segmentation, 2,6-bis(isocyanatomethyl) The bridge is full of chlorine, 1,5-, 2,5-, 1,6· and 2,6- (Isocyanate)-4,7-Medium bridge j-block full, dicyclohexyl·2,4,_ and 4,4,_diisocyanate, 2々 and 2, Y-methylisocyanate, all hydrogen-2, 4ι_二苯甲院西异王虱-4,4'_Diphenylmethane diisocyanate, 4,4,-bis(isocyanium hexyl) di 3 isocyanatomethyl_3 , 5,5-tridecylcyclohexyl isocyanate, etc., cyclic aliphatic-isocyanate; ω, ω, diisocyanyl-1,4-diethylbenzene, 146899.doc 201130868 Benzene monoisocyanate, p-benzene Diisocyanate, 4,4'-diisocyanatobiphenyl, 4,4-isoisocyanyl-3,3·dichlorobiphenyl, 4,4,diisocyanato-3,3 ,-Dimethoxybiphenyl '4,4'-diisocyanato-3,3,-dimethylbiphenyl, 4,4,-diisocyanato-3,3'-diphenyl Biphenyl, 2 4,_ and 4,4,-diisocyanato-diphenylmethane-1,5--isocyanate, 2,4-toluene diisocyanate, 2,6-nonylbenzene-isoisocyanate Sg, ν, Ν'-(4,4-dimercapto-3,3'-diisocyanatodiphenyl)urea-ketone, m-methyl-diisocyanate, diphenylnonane-2,4 ^Diisocyanate, benzoxane_4,4'-diisocyanate, 2,4,4,_triisocyanide An aromatic diisocyanate such as a diphenyl ether, a 4,4,4-diisocyanato triphenyl decane or a triisocyanate phenyl phosphorothioate. The above diisocyanate compound (Α) can be carbon bismuth The form of the modified substance such as the imine modification, the isocyanuric acid hydrazine modification, the digestive modification or the like can also be used in the form of the blocked isocyanate g which is blocked by various sealing agents. As the diisocyanate compound (A), yttrium phenylene diisocyanate and isophorone diisocyanate are preferred because the photocurable resin obtained has a higher adsorption property to the pigment. high. As a compound for obtaining a photocurable resin of the present invention, which has one or two hydroxyl groups in the molecule and a number average molecular weight of 3 〇〇 5 5 Å, a polyether is exemplified. Glycols, polyglycols, polyacetal glycols, polycarbonates, poly-diols, and alkyl groups having a carbon number of 1 to 25 (4) Those who are the recipients of the base filaments, etc., may also be used in combination. Ethylene glycol, triethylene glycol, and the like are added as the above polyether glycol, and examples thereof include an alcohol-specific epoxy epoxide adduct, dipropylene glycol, and diwa 146899.doc 201130868. Ethylene oxide and/or propylene oxide adduct of molecular polyol, polytetramethylene glycol, and the like. Examples of the polyester diols include ester-forming derivatives such as dicarboxylic diols having less than a stoichiometric amount of dicarboxylic acids or esters thereof, acid anhydrides, and halides, and/or Alternatively, the lactone or the hydroxycarboxylic acid obtained by subjecting it to hydrolysis and ring-opening is subjected to a direct esterification reaction and/or a transesterification reaction. Ο Ο Examples of the low molecular weight diols include ethylene glycol, diethylene glycol, triethylene glycol, L2-propylene glycol, propylene glycol, 2-methyl-nonanediol, and 2-butyl-2_B. Base_!,3_propylene glycol, M_butanediol, neopentyl glycol, 3:methyl-2,4-pentanediol, 2,4-pentanediol, pentanediol, %methyl-iso-penta Alcohol 2-methyl-2,4-pentanediol, 2,4-diethylfluorene pentanediol, hexanol-alcohol,! , an aliphatic diol such as 7_heptanediol, 3,5·heptanediol, a-octanediol, 2-methylidene-1, 1,8-octyl-alcohol, oxime diol, "o-decanediol; % hexane-aliphatic diol such as methanol or cyclohexane diol; aromatic diol such as benzenedimethanol or bis(hydroxyethoxy). Examples of the above binary 敎//I include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, heptanoic acid, suberic acid, sebacic acid, and decylene. Acid, maleic acid, dodecanedioic acid, 2-mercaptohexanedi-T-butyl-methyl adipate, 3-mercaptoglutaric acid, 2-carbazone, 3,8 -Dimethicone. Dimer acid, two (four) diacid, 3,7. dimethyl azelaic acid, hydrogenated formic acid, meta-hypo-acids such as phthalic acid, terephthalic acid, etc. (4) An aromatic di-lowering acid such as hydrazine formic acid, a cyclohexyl-carboxylic acid; and as the above-mentioned ester-forming derivative, 146899.doc 201130868: an acid anhydride of the dicarboxylic acid, a halogenated gas of the dicarboxylic acid or the like And a lower aliphatic ester such as a methyl ester, an ethyl ester, a propyl ester, an isopropyl ester, a dibutyl sulfonium ketone, or a pentyl ester of the dicarboxylic acid, which may be used in combination. Examples of the internal vinegar include γ_本内自, δ_内内, ε·caprolactone, dimethyl-ε-hexene s, δ-pentene, and γ-pentene. In the case of D. Examples of the polyester polycarbonate diol include those obtained by simultaneously reacting a diol, a dicarboxylic acid, and a carbonate compound such as a dialkyl carbonate, an alkylene carbonate, or a diaryl carbonate; A method of reacting a pre-synthesized polyester polyol and a polycarbonate polyol with a carbonate compound; or obtaining a pre-synthesized polyglycol and a polyacetate (IV) with a polyol and a polycarboxylic acid Wait. The polycarbonate diols may, for example, be poly(1,6-exexyl)carbonate or poly(3.methyl-indole-pentyl)carbonate. As the polyolefin diol, examples of the polyolefin diol include polybutadiene diol, hydrogenated polybutadiene diol, and hydrogenated polyisoprene diol. The compound (Β) having one or two hydroxyl groups in the same molecule is particularly preferably a polyether diol and/or a polyester diol, because the affinity with the solvent is preferable. The dispersibility of the photocurable resin is improved. The compound having one or two hydroxyl groups in the same molecule has a number average molecular weight of from 300 to 5,000 Å, preferably from 500 to 3,000. As the compound (c) having two hydroxyl groups and two ethylenically unsaturated groups in the same molecule for obtaining the photocurable resin of the present invention, for example, 146899.doc 201130868~μ listener and unsaturated- An adduct of a meta acid. : For the above difunctional epoxy compound, for example, it can be used: binary... = diglycidyl scale of the product, diglycidyl vinegar of the dibasic acid? The compound of the dilute ring or the cyclopentane ring is epoxidized with an oxidizing agent to obtain a compound of the epoxide or epoxycyclopentane, and the like, and specifically, the following compounds can be mentioned. Ο

It can also be enumerated: double (four) type epoxy resin, double-shut type epoxy resin, two kinds of oxygen-based resin of the formula (I), etc.: glycidol (four) epoxy tree moon 曰 'the double 朌 two Chlorinated bisphenol-type diglycidyl ether obtained by hydrogenation of glycidyl-based epoxy resin; ethylene glycol diglycidyl ether, i, propylene glycol diglycidyl ether, 1,2-propylene glycol diglycidyl ether, M- Butanediol dimerizer glycerin hydrazine, 1,6-hexanol diglycidyl hydrazine, I, octanediol dimethyl glycerol, 1,1 〇-nonanol diglycidyl fluoresce, 2,2-dimethyl Base-1,3-propanol-glycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidol a glycidyl ether of an aliphatic diol such as 1,4-cyclohexanediall diglycidyl ether; a phenolic novolac type epoxy compound, a biphenol novolak type epoxy compound, and a varnish type Epoxy compound, bismuth A anti-clear epoxide type epoxy compound, dicyclopentadiene novolac type epoxy compound, etc. 3,4-epoxy-3-methylcyclohexylcarboxylic acid _ 3',4'-epoxy-3-methylcyclohexylmethyl ester, 3,4-epoxy-5-methylcyclohexyl Formic acid _3',4,-epoxy-5-methylcyclohexylmethyl ester, 3,4-epoxy-6-methylcyclohexyl decanoic acid-3,,4,-epoxy-6- Nonylcyclohexylmethyl ester, 3,4-epoxycyclohexylcarboxylic acid _3',4,-epoxycyclohexylmethyl ester, 1-epoxyethyl-146S99.doc 201130868 3,4-epoxy Cyclohexane, bis(3,4-epoxycyclohexyldecyl) adipate, bis-(3,4-epoxycyclohexane), isopropylidene bis (3,4) _epoxycyclohexane), dicyclopentadiene dioxide, ethyl bis(3,4-epoxycyclohexylcarboxylate), 1,2-epoxy-2-epoxy An alicyclic ring gas compound such as ethylcyclohexene, a glycidyl ester of a dibasic acid such as phthalic acid diglycidyl hydrate, tetrahydrophthalic acid diglycidyl ester or dimer acid glycidyl ester; , glycidylamines such as n-diglycidylaniline; heterocyclic epoxy compounds such as i, 3_diglycidyl-5,5-dimethylhydantoin; dicyclopentadiene dioxide, etc. two Compounds thereof; naphthalene type epoxy compound, a stupid ρ methane type epoxy compound, a dicyclopentadiene-type epoxy compounds. [Chemical 1]

(wherein, Μ represents a direct bond, an alkylene group having a carbon number of 4, an anthracene ring = a group, a fluorene, a 8, 8 〇 2, a heart palpitus, a _ _ or a selected one; The above-mentioned sub-alkyl group can also be obtained by the imine atom = and R2 are independently represented by a hydrogen atom, the number of carbon atoms is 丨~5, and the number of carbon atoms is 2 to 5, and the number of carbon atoms is 2 to 5. The base or the substituent: and the alkyl group, the alkoxy group and the dilute group may also be taken by the atom. Μ can also be joined to form a ring structure, η is. Or "丨. The whole 146899.doc •10- 201130868 [Chem. 2]

〇 (wherein Q and B each independently represent a hydrogen atom, an alkyl group having a carbon number of 丨~(7) or an alkoxy group having a carbon number of (7), or a carbon atom number of 3 to 10; a cycloalkyl group, Z&E, respectively, independently represents an alkyl group having a carbon number, an alkoxy group having a carbon number, an alkenyl group having a carbon number of 2 to 1 Å, or an alkene atom, and the alkyl group, the alkoxy group The base group and the alkenyl group may also be substituted by a dentate element, and A and D each independently represent an alkyl group having 1 to 10 carbon atoms which may be substituted by a halogen atom, and the number of carbon atoms which may be substituted by a halogen atom is 6 to 2 〇. An aryl group, an aralkyl group having 7 to 2 ring carbon atoms which may be substituted by a sulfonium atom, a heterocyclic group having 2 to 20 carbon atoms which may be substituted with a fluorene atom, or a olefin atom The thiol group in the aryl group, the aryl group or the aralkyl group may also be interrupted by an unsaturated bond, -〇- or -S-, and the octagonal group may form a ring by A, 〇 or each of the eight and 1)' a ring, R3 represents a hydrogen atom, an alkyl group having a carbon number of U., an alkoxy group having a carbon number of U, an alkenyl group having 2 to 5 carbon atoms or a halogen atom, and the alkane , Alkoxy and alkenyl groups can also be substituted by atoms prime _, P represents the number of 0~5, k represents a number of 0~5, a represents the number of 〇~4, d represents the number of 0~4). 146899.doc -11 - 201130868 In the above formula (1), the alkylene group having a carbon number of 1 to 4 represented by M is exemplified by: methylene ymethylidene), ethylene (King Meling propylene) (pr〇pyildene), butylene (butylide), etc.; as an alicyclic hydrocarbon group, a cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group or a cyclooctyl group, or a ring a cycloalkenyl group such as a propylene group, a cyclobutenyl group, a cyclopentylene group, a cyclohexenyl group, a cycloheptenyl group or a cyclooctenyl group; and an alkyl group having 5 carbon atoms represented by R1 and R2, Examples thereof include a mercapto group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a second butyl group, a tert-butyl group, an isobutyl group, a pentyl group, an isopentyl group, a third pentyl group and the like; The oxy group of the formula is methoxy, ethoxy, isopropoxy, propyl, butoxy, pentyloxy, isoamyl, hexyloxy, heptyloxy, octyloxy Examples of the alkenyl group having 2 to 5 carbon atoms include a vinyl group, a propenyl group, and a butyl group, "Φ 呉 propylene group, butenyl group, isobutenyl group, pentene. Base Examples of the halogen atom include fluorine, chlorine, molybdenum, and hydrazine. Examples of the ring structure in which R1 and R2 are bonded to each other include a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a benzene ring, and a (iv) ring. a ring of 5 to 7 members such as a ring of styrene, an inner vinegar ring, an inner (four) ring, and a condensed ring such as a ring of Cai ring, a core ring, a ring of a ring, a ring of an anthracene, a ring of a naphthalene ring, or the like. Group

In the substituent, the number of carbon atoms which can be substituted for the phenyl group represented by Q and B is exemplified by methyl group, ethyl group, propyl group, isopropyl group and butyl group: : a third pentyl group, a hexyl group, a heptyl group, an iso-heptylisooctyl group, or the like, an isobutyl group, a pentyl group, an isopentyl group, a third heptyl group, a n-octyl group, a n-decyl group, a n-decyl group Trioctyl, 2-ethylhexyl as alkoxy group having 1 to 10 carbon atoms which may be substituted by benzene 198899.doc -12- 201130868, represented by Q and B, except as indicated by Examples of the alkoxy group having 1 to 8 carbon atoms and the same groups are exemplified, and examples thereof include a decyloxy group and a decyloxy group. Examples of the ring group having a carbon number of 3 to 1 Å include a ring. Propyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, cyclodecyl and the like. As a group based on the number of carbon atoms represented by ME, 盥 is used as a hydrazine which can replace the phenyl group represented by QAB and has a carbon number of H0.

The bases exemplified are the same, and the group exemplified as the alkoxy group having a carbon number of H0 may be exemplified as the alkoxy group having 1 to 10 carbon atoms which may be substituted with the base of q and BT. The same as the "area", as an alkenyl group having 2 to 1 ring of carbon atoms, except for the base which is not based on the number of carbon atoms represented by Q and 矣 - ^ ^ In addition to the above, it may also be a hexyl group, a heptenyl group, a heptyl group, a decyl group, a decyl group, a decyl group, etc., and a halogen atom, which is exemplified as a halogen atom represented by Q and The base of the illustration is the same. As the alkyl groups of the carbon atom disks 1 to 10 which are represented by A and D, which are substituted by a prime atom, are represented by 丨 _ > H 卩 and 8 as the ', the number is the alkene The number of carbon atoms is from 1 to 10, and the m-substituent of the base group is substituted by w. Further, difluoromethyl, difluoromethyl, monofluoromethyl, which is a radical of the self-purine atom: Pentafluoroethyl, tetraethyl, trifluoroethyl, di-a 5-ethyl, pentafluoropropyl, tetrafluoro-- propyl propyl, hexafluoropropyl, difluoropropyl, perfluorobutan The number of carbon atoms in which 聱HA can be substituted by a ruthenium atom is 6 to 20=set as a group, 1-naphthyl group, 2-naphthyl group, ^ i. Illustrative: Benzene-'----------phenanyl, ortho-X Its base, p-tolyl, 3_dry base, m-methyl y. soil, 9·diyl, 1-tetrahydro-hydrogen, hydroquinone, b β fly-free, 2-tetra- Heart group, 2_dihydrogenated group, 4-ethenyl group 146899.doc -13· 201130868 Phenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4- Isobutylphenyl, 4-tert-butylphenyl ' 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4_(2-ethyl Phenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2 6-dimethylphenyl, 3,4-dimethyl Phenyl, 3,5-dimethylphenyl, 2,4-di-tert-butylphenyl, 2,5-di-t-butylphenyl, 2,6-di-t-butylphenyl, 2, 4_di-t-amylphenyl 2,5--second amylphenyl, biphenyl, 2,4,5-trifylphenyl, 4 chlorophenyl 3,4-monophenyl, 4 _ trichloromethylphenyl, trimethylmethyl group, all-% phenyl, etc.; as a aryl group which can be substituted by a halogen atom and having 7 to 2 碳, a benzyl group , 2-phenylpropyl, dibenzylmethyl, triphenylmethyl, styryl, phenylallyl, 4-phenylphenylyryloxy, 1-naphthyloxy, 2• Naphthylmethoxy oxalyl methoxy, etc.; as a heterocyclic group which may be substituted by a silane atom, a base group: a base group, a base group, a base group, a (tetra) group, a bottom base group, a base group ,. Compared with the seat base, the three 卩 well, the 咐 〜 ~ w ^ open I than slightly. Anthracenyl, quinolyl, isoquinolyl, imsylbenzopyranyl, disalyl, carbyl y), fUranyl, benzofuranyl...thienyi ), phenylthio-CP11 — ), benzophenylthio 1 di-salyl, hydrazine, benzene, sulphate, sulphate, benzo-xyl-based, iso-anthracene, hetero- 10 m-based long-term cough Base, taste Linji, thio-terinyl, 嘻 嗣 其 、 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- The halogen atom is the same as the one exemplified as the halogen atom represented by Q and B. The alkoxy group having a carbon atom number of (4) represented by R3, the alkoxy group having a carbon number of 146 146899.doc -14 to 201130868, the alkenyl group having 2 to 5 carbon atoms, and a halogen atom are exemplified by the above formula. The base illustrated in the description of (I). As the ring structure which can be formed by A, D, or A and D, the groups exemplified in the above formula (I) can be listed. The above-mentioned difunctional epoxy compound can also be used by a commercially available person, and examples thereof include NC-3000, AK-601, GAN, and GOT (manufactured by Sakamoto Chemical Co., Ltd.).

Adeka Resin EP-4000, Adeka Resin EP-4003S, Adeka Resin EP-4080, Adeka Resin EP-4085, Adeka Resin EP-

4088, Adeka Resin EP-4100, Adeka Resin EP-4900, Adeka Resin ED-505, Adeka Resin ED-506, Adeka Resin KRM-2110 ' Adeka Resin KRM-2199 ' Adeka Resin KRM-2720 (made by ADEKA), R -508, R-531, R-710 (manufactured by Mitsui Chemicals, Inc.), Epikote 190P, Epikote 191P, Epikote 604, Epikote 801, Epikote 828, Epikote 871, Epikote 872, Epikote 1031, Epikote RXE15, Epikote YX-4000, Epikote YDE-205, Epikote YDE-305 (made by Japan Epoxy Resins Co., Ltd.), Sumiepoxy ELM-120, Sumiepoxy ELM-434 (manufactured by Sumitomo Chemical Co., Ltd.), Denacol EM-150, Denacol EX 0.001, Denacol EX -211, Denacol EX-212, Denacol EX-313, Denacol EX-314, Denacol EX-322, Denacol EX-411, Denacol EX-421, Denacol EX-512 ' Denacol EX- 521, Denacol EX-614, Denacol EX -711, Denacol EX-721, Denacol EX-731, Denacol EX-811, Denacol EX- 821 > Denacol EX-850, Denacol EX-851, Denacol EX- 146899.doc -15- 201130868 911 (长濑化成( Nagase Chemtex), Epolight 7 0P, Epolight 200P, Epolight 400P, Epolight 40E, Epolight 100E, Epolight 200E, Epolight 400E 'Epolight 80MF, Epolight 100MF, Epolight 1500NP, Epolight 1600, Epolight 3002, Epolight 4000, Epolight FR-1500, Epolight M-1230, Epolight EHDG -L (manufactured by Kyoeisha Chemical Co., Ltd.), SB-20 (manufactured by Okamura Oil Company), Epiclon 720 (manufactured by Dainippon Ink Chemical Co., Ltd.), UVR-6100, UVR-6105, UVR-6110, UVR-6200, UVR- 6228 (manufactured by Union Carbide), Celloxide 2021, Celloxide 2021P, Celloxide 2081, Celloxide 2083, Celloxide 2085, Celloxide 3000, Epolead HD300, EHPE-3150, ETHB, Epofriend (Daicel Chemical Co., Ltd.), PY- 306, 0163, DY-022 (Ciba Specialty)

Chemicals) 811111'〇1^〇81[0000, Qiu〇1〇1^〇¥1> Oil ' Epotohto YD-115 ' Epotohto YD-127 ' Epotohto YD- 134 ^ Epotohto YD-172 ' Epotohto YD -6020 ^ Epotohto YD-716 ' Epotohto YD-70HR ' Epotohto YD-901 ' Epotohto YDPN-638 ' Epotohto YH-300 ' Neotohto PG-202 '

Neotohto PG-207 (manufactured by Tohto Kasei Co., Ltd.) Epl01 E_100, Epl01 E-400, Epiol E-1000, Epio1 NPG-100 (manufactured by Nippon Oil Co., Ltd.) '苐-based epoxy compounds BPF-G, BCF_G, BPEF_G (〇saka) Gas company) and so on. The difunctional epoxy compound is preferably a compound represented by the above formula (1), and more preferably M in the above formula (1) is represented by the above [Chemical Formula 2], 146899.doc •16·201130868 especially Those represented by the following general formula (II), (III) or (IV) are represented by the following general formula (V), or an anthracene epoxy compound BPF-G, BCF-G, G (manufactured by Osaka Gas Co., Ltd.) The reason for this is that the dispersibility of the photocurable resin obtained is improved. [Chemical 3]

(Π) (wherein, Rl, R2, Q, z, n, and p are the same as the above formula (I))

(III) ❹ The same as in the general formula (I)) (wherein R 1 , R 2 and η and upper [5]

146899.doc (IV) 201130868 a, d and n are the same as the above formula (!). (where R', r2, A, D [6]

(wherein R and R each independently represent a hydrogen atom, an alkoxy group having a number of carbon atoms of 1 to 5 of 1 to 8, a dilute group having 2 to $ carbon atoms, or a dimer: The base, the oxy group and the alkenyl group may be substituted by a crypto atom or may form a ring structure, and n is the same as the above formula (1). In the above formula (V), a group having 1 to 5 carbon atoms in the range of R 4 and R 5 , an alkoxy group having 1 to 8 carbon atoms, and an alkene having 2 to 5 carbon atoms; The base and the imine atom are classified as the groups exemplified in the description of the above formula (1). Examples of the unsaturated-acid acid include acrylic acid H (tetra) acid, crotonic acid, cinnamic acid, sorbic acid, and methyl propyl superphosphate-maleic acid S. B from the purpose of - maleic acid from the purpose, hydroxypropyl methacrylate - maleate, hydroxypropyl acrylate - cis butyl; diester, dicyclopentadiene A difunctional (meth) acrylate having a propylene group and the like. The above difunctional (meth) acrylate having one carboxyl group and two (meth) acryloyl fluorenyl groups can be, for example, one hydroxyl group and two (meth) propyl groups in one molecule. 146899.doc -18- 201130868 A difunctional (meth) acrylate of fluorenyl is obtained by reacting with a dibasic acid anhydride or a carboxylic acid. Examples of the difunctional (fluorenyl) acrylate having one carboxyl group and two (meth) acrylonitrile groups include the following compounds N〇.1 or N〇.2. [Chem. 7] Compound No. 1

Compound No. 2 0

As the above unsaturated monobasic acid, acrylic acid or methacrylic acid is preferred because it is easily available. Examples of the compound (D) having an active hydrogen and a tertiary amino group in the same molecule include ruthenium, osmium-dimercapto-1,3-propanediamine, ruthenium, osmium-diethyl-1. 3-propanediamine, hydrazine, hydrazine-dipropyl-hydrazine, 3-propanediamine, hydrazine, hydrazine-dibutyl-hydrazine, 3-propanamine, hydrazine, hydrazine-dimethylethylenediamine, hydrazine , Ν-diethylethylenediamine, hydrazine, hydrazine-dipropylethylenediamine, hydrazine, hydrazine-dibutylethylenediamine, hydrazine, hydrazine-dimethyl-1,4-butanediamine, 146899. Doc •19· 201130868 N,N-Diethyl-1,4-butanediamine, N _ ,-propyl-1,4-butanediamine, n,N-dibutyl-1,4-butyl Diamine and other fats are lost to one amine, still piped, piped, i 3__ f piperidine) propane, 2_methyl travels - (4' ^, () one base Brigade 51 well, 2, 5 - Dimethyl morphine, menthol diamine, etched earth, ketone diamine, bis(4-amino-3-indolyl-cyclohexyl) decane, diamine 瑷Pb T soil, Alkane, diaminodicyclohexylmethane, 3,9, bis(3-aminopropyl)_2 4 8 in m soil) A4,8,10•tetramilospiro[5,5]undecane, Amino-2-mercaptopropyl) piperene, 丞""Γ曰1 each diamine, poly ring Methyl)bicyclo[2.2.U heptane, α bis (amine fluorenylmethyl bis (furanmethylamine)) and other alicyclic diamines, dibenzoic acid diamine, dichlorodibenzoic acid diamine, toluene An aromatic diamine such as diamine, diethyltoluenediamine, benzidine or phenylenediamine; an aromatic aliphatic diamine such as xylylenediamine or tetramethylaniline; Ν-methyl 派, Ν _ Ethyl piperene, Ν _ butyl piper, octyl cisplatin and other alicyclic amines; containing pyrazole ring ... rice saliva ring, three wah ring, four ring ring 'ten ring ... card catal ring, ten sitting, Benzene oxime ring, benzotrisene ring, benzoxene ring, benzoxanthine, benzopyrene, and other nitrogen-containing five-membered rings "bite ring"荅唯环, ^ a three-membered ring of a three-ring ring, a (four) ring, a bite ring, a heterocyclic ring, and the like, and a compound of a nitrogen-containing six-membered ring and a class of an amine group, preferably a hydrazine-methyl group or a Ν_乙娘Ρ井The reason for this is that the photocurable resin obtained has an improved adsorption property to the pigment. Among the compounds containing a nitrogen-containing heteropentacyclic ring and a primary amino group, for example, a compound containing an imidazole ring and a primary amino group can be enumerated :-amine Propyl)imidazole, histidine, 2-aminoimidazole, anthraquinone-ethylamino), etc. As a compound containing a triazole ring and a primary amino group, 3 amino group-1, 2 , 4-triazole, 5-(2-amino-5-chlorophenyl)-3-phenyl_1Η-1 2 4_彡I46899.doc -20- 201130868 base-5-phenyl-1H-, 3-amino-1.-benzylazole, 4-amino-4H-1,2,4-triazole_3,5-diol, 3-amine 1,3,4-diazole, 5-amino group_ι , 4_diphenyl-indole, 2,3-triazolyl-1Η-2,4-trisal, and the like. The introduction amount of the compound (1)) having an active hydrogen and a tertiary amino group in the same molecule is preferably controlled in the range of 1 to 1 〇〇 mg K 〇 H / g based on the amine value of the photocurable resin obtained. Preferably, it is controlled within a range of 5 to 95 mgKOH/g J5. If it is difficult to be outside the range of ±, there is a tendency for the ability to decrease.

The polyvalent sulfonic anhydride (E) which is used as needed in order to obtain the photocurable resin of the present invention may be exemplified by succinic anhydride, maleic anhydride, trimellitic anhydride, and pyrethic anhydride. 2,_3,3,_dibenzophenone tetracarboxylic anhydride, 3,3·-4,4ΐ-benzophenone tetracarboxylic anhydride, ethylene glycol trimellitous anhydride, glyceryl trimellitic anhydride, Phthalic anhydride, hexahydrophthalic anhydride, liver of methyltetrahydrophthalic acid, tetrahydrophthalic anhydride, terephthalic anhydride, methylic acid anhydride, trialkyltetrahydroortylene Formic anhydride, hexahydrophthalic anhydride, 5-(2,5-dioxotetrahydrofuranyl)_3_methyl_3_cyclohexene-n monocarboxylic anhydride, trialkyltetrahydrophthalic anhydride The maleic anhydride adduct is undecenyl succinic anhydride, methyl bicycloheptylene anhydride, and the like. Among these, succinic anhydride, trimellitic anhydride, and hexahydrophthalic anhydride are preferred. The photocurable resin of the present invention is a compound having i or 2 hydroxyl groups in the same molecule and having an average number of 300 to 5000 in the same molecule with respect to the isocyanate group of the diisocyanate compound (b). The ratio of 羟基2 to 0.5, and two hydroxyl groups and two ethylenically unsaturated groups in the same molecule. 146899.doc -21 - 201130868 Compound (c) hydroxy 0 5~0 98 ratio After the addition, a compound having two hydroxyl groups and two ethylenically unsaturated groups in the same molecule (an ethylenically unsaturated group of fluorene, a compound having an active hydrogen and a tertiary amino group in the same molecule) D) The active hydrogen hydrazine. The ratio of 〇1 to 0.4 is obtained by adding wheat. Among them, the total of the hydroxyl group of the compound (B) which contributes to the reaction and the hydroxyl group of the compound (c) and the compound (A) Further, the isocyanate group may be the same, and may be further esterified with a hydroxyl group of the polybasic acid anhydride (E) in an amount of 0.1 to 1 to 0. The photocurable resin of the present invention is used by SEC (Size Exclusi). ()n

ChiOmatc), volume exclusion chromatography) has a mass average molecular weight of from 1 〇〇〇 to 50,000. When the mass average molecular weight is 10,000 or less, the dispersibility and the dispersion stability are not obtained. When the mass average molecular weight is 50,000 or more, the solubility is lowered, the dispersibility is deteriorated, and the control of the reaction is difficult. In the reaction for obtaining the photocurable resin of the present invention, a usual amine sulfonate S catalyst can be used as a catalyst. Examples of the urethane reaction reaction catalyst include, for example, dibutyltin dilaurate, dioctyltin dilaurate, dibutyltin-octanoate, dibutyltin diacetate, and dibutyltin thioformate. Tin-butyltin, dioctyltin thioate, stannous octoate, etc., iron such as iron acetonitrile, iron oxide, triethylamine, pentamethyl-ethylamine, pentadecyldipropylenetriamine, Tertiary amines such as tetradecyl fluorene, triethylmethyl π wei, sulfhydryl ethyl „ well, methyl phenanthrene, dimercaptoethyl porphyrin, dimethylimidazole and other cyclic amines Etc.: The reaction for obtaining the photocurable resin of the present invention may be as appropriate. 146899.doc • 22· 201130868 The solvent is used. As the solvent, methyl ethyl ketone, decyl amyl ketone, and diethyl ketone may be mentioned. , acetone, methyl isopropyl ketone, methyl isobutyl ketone 'cyclopentanone, cyclohexanone, isophorone and other ketones; ether, two saki, tetrachloro. Fu Wei, Ϊ, 2- An ether solvent such as methoxyethane, diethoxyethane or dipropylene glycol dimethyl ether; methyl acetate, ethyl acetate, and n-propyl acetate Ester solvent such as isopropyl acetate or n-butyl acetate; ethylene glycol monomethyl sulphate, ethylene glycol mono succinct, propylene glycol monomethyl acetate acetic acid, cellulose cellosolve and other cellosolve ❹ 〇 solvent; methanol Alcohol solvent such as ethanol, iso- or n-propanol, iso- or n-butanol, pentanol or acetol; ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl acetate, propylene glycol oxime ether acetic acid Ether ester esters such as esters; BTX (benzen-toluene-xylene, | _ _ _ _ _ _ _ _ 1-toluene) solvent; hexane, heptane, octane An aliphatic hydrocarbon solvent such as cyclohexane; a terpene hydrocarbon oil such as turpentine, D-limonene or decene; mineral spirits, Swasol #310 (Cosmo Matsuyama Oil Co., Ltd.) Solvesso #100 (Exxon Chemical Co., Ltd.) Company), etc. six kinds of paraffin wax; four gasified carbon, gas imitation, three gas ethylene, two gas methane, dichloroethane, etc. _ _ aliphatic hydrocarbon solvent; gas benzene and other _ aromatic hydrocarbon solvent ·, N , non-protonic polar solvent such as N-dimethylformamide, N-methylpyrrolidinium, dimethyl arsenate; carbitol solvent, aniline Two, -G amine, η ratio. The solvent may be used in the form of acetic acid, acetonitrile, carbon disulfide, water, etc., or a mixed solvent of two or more kinds may be used. The photocurable resin of the present invention can be produced, for example, by the method shown by the following reaction [Chemical Formula 9]. First, on the diisocyanate compound (1) as the (Α) component, 146899.doc •23- 201130868 is added as the component (B), and the compound (2) having one or two warp groups in the same molecule, and The compound (3) having two hydroxyl groups and two ethylenically unsaturated groups in the same molecule as the component (C). The addition reaction of the component (b) and the component (C) to the component (A) can be carried out according to a usual method, and it is preferred to carry out the reaction at 60 to 90 ° C for 1 to 10 hours. Then, 'Mcco can be added as a compound having active hydrogen and a tertiary amino group in the same molecule as the component (D), for example, an amine (4). The methic acid addition reaction of the component (D) can be carried out according to a usual method, and it is preferred to carry out the reaction at 2 Torr to 5 ° C for 1 to 10 hours. Then, the polybasic acid anhydride as the component (E) is subjected to an esterification reaction to obtain a compound (6) as a photocurable resin. The esterification reaction of the component (E) can be carried out according to a usual method. It is preferred to carry out the reaction at 20 to 50 ° C for 1 to 1 hour. [Chemistry 9]

rVkh

146899.doc •24· 201130868 (wherein X represents a residue of a non-difunctional epoxy compound, γ represents a diisocyanate-residue 'R represents a non-atom atom or a methyl group, and Rc& Rd has a single atomic number a heterocyclic group HRd having a carbon number of from 2 to 5 and an aryl group having 6 to 20 carbon atoms and having a carbon number of 2 to 2 G may be bonded to form a ring structure = and R independently represents a chlorine atom, The alkyl group having a carbon number of 5 is an alkoxy group having a number of slave atoms of 1 to 8, a dilute group having 2 to 5 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a halogen atom. Base, alkoxy group and alkene

The group may also be substituted with a (tetra) atom. 'RaARb may also be bonded to form a ring structure, and S and t are respectively 〇~1〇〇〇, and the sum of s + t is 2 or more.) The photohardenability of the present invention described above Resins can be used in a wide range of applications such as lithographic inks, gravure inks, inkjet inks, coatings, cosmetics, adhesives, conductive materials, conductive papers, resin pigments, electrophotographic materials, fillers, and reinforcing agents. , coating materials, battery materials, electrode materials, electronic materials, antistatic materials, electromagnetic wave shielding materials, cable semi-conductors, planar heating elements, adsorbents, catalysts, plastic or rubber modifiers, lubricants, non-linear Optical materials, fibers, carbon nanotubes, plating, various recording media, sealants. Next, a pigment composition using the photocurable resin of the present invention as a dispersing agent will be described. The photocurable resin of the present invention can be dispersed as a dispersing agent together with a pigment and a binder resin in a solvent to prepare a pigment composition. In the pigment composition, the content of the photocurable resin as a dispersing agent is preferably 轻 θ ^ , which is preferably 30 to 90 in the solid content of the pigment composition, and more preferably 40. ~60% by mass. 146899.doc -25- 201130868 For example, the following organic or inorganic pigments can be used: sulphate WW compound, peroxide, "peroxide" hawthorn star::, gueline compound, onion compound , citronin compound, (four) chemical compound, iso, dolonone compound, iso, lindane compound, onion scallop compound, purple ring compound, flower compound, diterpene: bismuth compound, sulfur Indigo compound, ... compound, three:: burning compound, money ketone compound, naphthalene tetracarboxylic acid; azo dye, granule-material metal complex compound; color house pigment, activated carbon, carbon fiber, carbon nanotube, Coiled carbon fiber, carbon nanohorn, carbon aerogel, fullerene; hydrophobic resin; chromium oxide, oxidation record, iron oxide, silver oxide, titanium oxide, zinc oxide, atmosphere (four), potassium oxide, dioxane, Oxidized metal oxides; layered clay minerals, milorie blue, carbonic acid, magnesium carbonate, cobalt, talc, talc, kaolin, ferrous compound, various metal sulfates, sulfides, selenides, phosphoric acid Salt green, iron blue, ultramarine, Blue, chrome green, green Weng like. These pigments may be used singly or in combination of plural kinds. In the above pigment composition, the content of the pigment is preferably from 10 to 80% by mass, more preferably from 30 to 7% by mass, based on the total solid content of the pigment composition. A commercially available product can also be used as the above pigment. Examples of commercially available products include pigment red 1, 2, 3, 9, 1 , 14, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90, 97, 112, and 119. 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, U4 '185, 192, 200, 202, 209, 215, 216, 217, 220, 146899.doc -26· 201130868 223, 224, 226, 227, 228, 240, 254; Pigment Orange η, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64 , 65, 71; Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 95, 97, 98, 100, 1〇9 , 110, 113, 114, 117, 12 〇, i25, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168, 175, 18 〇, 185 Pigment Green 7, 1, 〇, 36; Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 〇I5 · 6, 22, 24, 56, 60, 61, 62 , 64; pigment purpura, 19, 23, 27, 29, 30, 32, 37, 40, 50, and the like. The binder resin is not particularly limited, and an adhesive commonly used for ink, coating, coating (4), and solder resist # can be used. For the binder resin, for example, a photocurable resin other than the photocurable resin of the present invention, a thermosetting resin, an alkali-soluble resin, an acrylic resin, a synthetic nylon, and a southern molecular latex can be used. Melamine resin, phenol tree Q 曰裒 树 曰, diallyl phthalate resin, petroleum resin, maleic acid resin, phenol resin, acid alcohol resin, polyoxyn resin, fluorocarbon resin, borrow Polyamine-based acid vinegar, gelatin, road protein, temple powder, cellulose derivative, alginic acid and other natural polymer materials obtained from the reaction of a cyclic (alicyclic or aromatic) isocyanate with a polyhydric alcohol, polyethylene Butyraldehyde, polyethylene oxime, polyvinyl alcohol, polyanthracene, polyvinyl chloride, styrene copolymer, polystyrene, polycarbonate, polyamide, polyester, and the like. The content of the above-mentioned binder resin in the above pigment composition is preferably from 1 to 70% by mass in the total solid content contained in the pigment composition, and further 146899.doc • 27-201130868 is preferably 3~ 30% by mass. The solvent is not particularly limited as long as it is a solvent capable of dispersing the above-mentioned respective components, and for example, a solvent which is used in the reaction for obtaining the photocurable resin can be used. These solvents may be used alone or in combination of two or more. Mixed solvent. The above pigment composition is preferably prepared in such a manner that the content of the solvent is as follows: even if all the solid content contained in the pigment composition is 〇·1 to 30% by mass. A photopolymerization initiator can be used in the above pigment composition. As the photopolymerization initiator, a previously known compound can be used, and examples thereof include: benzamidine peroxide, 2,2,-azobisisobutyronitrile, benzamidine, phenylbiphenyl ketone, and hydroxy group. Benzyl decyl Cyclohexane, Benzene oxime, Benzene dimethyl, condensed _, 节 基 -1 - didecylamino-1-(4,- sylylene benzoyl) propane , 2_ porphyrinyl 2_(4,-methylmercapto) benzhydryl propane, 9-oxothiopurine, 1-gas-4-propoxy -9 gastric oxygen sulfide, hawthorn, isopropyl _9_ oxysulfonium, diethyloxosulfuric acid, hawthorn, ethyl hydrazine, 4-phenylidene methyl diphenyl sulfide, benzoin butyl ether, 2-hydroxy-2-benzhydryl Propane, 2-hydroxy-2-(4·-isopropyl)benzhydrylpropane, 4-butylbenzylidene-based tri-aeration, meta- 4 oxo-oxybenzoic acid, gas-burning, benzoquinone Methyl carbazate, 1,7_bis(9|united) Gengyuan, 9-n-butyl-3,6^(2,_weilinylisobutyl). Sit, 2-methyl-indole _[4_(indenylthio)phenyl]_2_ porphyrinylpropane-b-b, p-methoxyphenyl-2,4, bis(trioxanyl)_three tillage , 2_曱基_4,6_ bis (three gas sulfhydryl)-all three sprays, 2_phenyl_46_bis(trichloromethyl)_ all three wells, 2-naphthyl-4,6-double (trichloromethyl)_all three tillage, 2_(p-butoxystyryl)_ 146899.doc -28· 201130868 all three tillage, 2-(p-butoxystyryl)_5_trimethylmethyl _,3,4•oxadiazole, 9-phenyl acridine, 9,10-dimethylbenzophenone, benzophenone/micilerone, hexaarylbiimidazole/mercaptobenzimidazole , 9-oxopurine pf/amine, bis(2,4,6-diamidinobenzoyl)-phenylphosphine oxide, and Japanese Patent Laid-Open No. 2000-80068, Japanese Patent Laid-Open No. 2 Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. A compound or the like described in the publication. Among the above, etc., a compound represented by the following formula (a) or (c) is preferred. [化 10] Λ I?*2

❹ (wherein R71, R72 and R73 each independently represent R, OR, CORR, SR, CONRRi or CN' R and a ruler, and represent an alkyl group, an aryl group, an arylalkyl group or a heterocyclic group, and the oxime can also be used. Substituted by a halogen atom and/or a heterocyclic group, wherein the alkyl moiety of the alkyl group and the aralkyl group may also be interrupted by an unsaturated bond, an ether bond, a thioether bond or a vinegar bond, and X, RAR may also be used together. Forming a ring, r74 represents a dentate atom or a burnt group, and R75 represents a hydrogen atom, a _ atom, a burnt group or a substituent represented by the following formula (b), and § is an integer of 〇~4' when § is 2 or more When a plurality of R74 can also be different bases). 146899.doc •29· 201130868 [Chem. 10-1]

(b) (wherein 'ring Μ denotes a ring-burning ring, Guanfuban fangfang% or a heterocyclic ring, R76 represents a symplectic symplectic; f or an alkyl group, Y' represents oxygenate _ primogen β 7 *, &quot ; atom or selenium atom, Ζ71 indicates that the number of carbon atoms is 1~5, and the η base h is not an integer of 0~4. When h is 2, the plurality of X73 may be different. Base). [Chem. 11]

(wherein R6 and R7 independently represent (10) heart or CN, ~, R23 VIII. R - one, the number of atoms is - group, and the number of carbon atoms =, = argon aryl group and heterocyclic ring The hydrogen atom of the group may further be =: aromatic SR", NR32R33, c〇NR" C〇R, OCOR", _C(=N_OR31)_R32: tear-off 3, view _· prime atom, -CR31=CR32r33 : 〇 C〇R )_R32, CN, halo-substituted, R31, mR33 'carboxy or epoxy-yl, broken atomic number: :::::: argon: 'sub, sub-number is aralkyl or carbon number is ^ a heterocyclic group having an atomic number of 7 to 3 Å of 2 to 20, and the above-mentioned, R22, 146899.doc • 30 · 201130868 R23, R31, R32 and R33 represent a methyl group of the alkyl group of the substituent It may be interrupted 1 to 5 times by an unsaturated bond, an ether bond, a thioether bond, an ester bond, a thioester bond, a guanamine bond or a urethane bond, and the alkyl moiety of the above substituent may be a branched side chain ' It may be a cyclic alkyl group, the alkyl terminal of the above substituent may be an unsaturated bond ', and R22 and R23 and R32 and R33 may form a ring, respectively. R3 and R4 independently represent R21, 〇r21, sr21, COR21, CONR22R23 ' NR22C OR21, OCOR21, COOR21, SCOR21, OCSR21 'COSR21, CSOR21, CN, halogen atom or hydroxyl group, a and b are each independently 〇~4. X1 represents direct bonding or CO, χ2 represents oxygen atom, sulfur atom, selenium atom, CR41R42, CO, NR43 or PR44, R41, R, r43 and R44 each independently represent R2丨, OR21, COR21, SR21, CONR22R23 or CN, and R8 may be bonded to one carbon atom of the adjacent benzene ring via _Χ2_ Forming a ring structure 'or R8 and R9 may form a ring together, and R 1 , R43 and R44 are each independently, and may form a ring together with any adjacent benzene ring). Further use of the ethyl acetonate may be used in combination with the above pigment composition. a body, a chain transfer agent, a surfactant, etc. Examples of the ethylenically unsaturated bond monomer include ethyl acrylate, ethyl hydroxypropyl acrylate, isobutyl acrylate, n-octyl acrylate, and acrylic acid. Octyl ester, isodecyl acrylate, stearyl acrylate, methoxyethyl acrylate, decylaminoethyl acrylate, acrylic acid, 1,6-hexanediol diacrylate, trishydroxypropyl propane Acrylate, methyl propyl Acid 2-hydroxyethyl ester, 2-hydroxypropyl methacrylate, butyl methacrylate, tert-butyl methacrylate, cyclohexyl acrylate, = 146899.doc -31 · 201130868 methyl propane Dimethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol, acrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, tricyclodecane dimethylol diacrylate, and the like. As the above chain transfer agent, thioglycolic acid 'thiol fruit I & salicylic acid, 2 - mercaptopropionic acid, 3-mercaptopropionic acid, 3-sulfenyl butyl N (2-mercaptopropyl propyl) Glycosyl)glycine, 2_mercaptonicotinic acid, 3_[2(fluorenylethyl)amine hydrazino]propionic acid, 3_[n_(2-sulfoethyl)amino]propionic acid, N_ P Μ base;) alanine ' 2 _ mentyl acid, % mercapto propionic acid, 4 _ butyl butyl acid, undecyl (4 - methylthio) phenyl ether, mercaptoethanol, % Zhiji 1,2-propanol, 丨_疏基_2_propanol, 3·s-butanol, decyl benzene, 2-1-ethylamine, 2-carbyl oxazole, 2_weiki a mercapto compound such as pyridyl, ruthenium, fluorenylacetic acid, trimethyl methacrylic acid tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropionate), A disulfide compound obtained by oxidizing a thiol 4 s substance, a dialkyl compound such as iodoacetic acid, iodopropionic acid, hydrazine ethanol, 2 moth, and 3 fluorene acid. As the above-mentioned surfactant, an anion system such as a fluorine-based surfactant such as an all-I-based (10) §, a sulphur-based sulfonium salt, a higher fatty acid metal salt, a sulphuric acid salt, or a sulphur-based sulfate can be used. Surfactant, high-grade amine gas _ 酉夂 salt 'quaternary ammonium salt and other cationic surfactants, polyethylene glycol hospital base ^, polyethylene glycol fatty acid vinegar, sorbitol liver fatty acid vinegar, fatty acid monoglycerin _, etc. A nonionic surfactant, an amphoteric surfactant, a surfactant such as a polyoxyn surfactant, or the like may be used in combination. It is also possible to further use a thermoplastic organic polymer in the above pigment composition to improve the properties of the cured product. As (4) plastic money polymer, for example, 146899.doc •32· 201130868 List: polystyrene, polymethyl methacrylate, yttrium methacrylate __ ethyl acrylate copolymer, poly(meth)acrylic acid, phenethyl hydrazine - (meth)acrylic acid copolymer, (meth)acrylic acid-methyl methacrylate copolymer, polyethylene butyl phthalate, cellulose ester, polypropylene decylamine, saturated polyester, and the like. It may also be used in combination with the above pigment composition: viscosity adjuster, PJJ value adjuster, surface tension adjuster, thickener 'thixotropy imparting agent, leveling agent, antifoaming agent, adhesion imparting agent, anisole , hydrothermal polymerization inhibitors such as hydroquinone, o-stupid, third-butyl catechol, and thiophene, catalyst, hydrazine, plasticizer, adhesion improver, filler, Shi Xizhu Coupler, chelating agent, humectant, penetrant, mold inhibitor, rust inhibitor, preservative, anti-drying agent, quick-drying agent, fixative, antioxidant, ultraviolet absorber, thermal stabilizer, flame retardant , lubricants, processing aids, anti-caking agents, electrolytes, catalysts, other dispersants, etc. As a method of dispersing or pulverizing the above pigment by using the photocurable resin of the present invention as a dispersing agent, a mortar, a bead mill, a plastic mill, a ball mill, a vibratory ball mill, a roll mill, and a rod mill can be used. Machine, barrel mill, cone mill south amplitude ball mill, pin mill, key mill, knife key mill, spoiler, jet mill, back spray mill, spiral jet mill, jet mill Jetmizer), micronizer, nano pulverizer ((10) such as claw 丨), Majac mill, micro at〇mizer, micron mill, spinning A method such as a rotary cutter, an impact pulverizing mill, a compression shearing mill, a Henschel mixer, or the like. The above-mentioned pigment resin composition can be known by a spin coater, a slit coater, a 轺1 type coater, a curtain coater, a variety of printing, impregnation, etc. 146899.doc • 33· 201130868 The device is applied to a support substrate such as metal, paper or plastic. Further, the pigment resin composition may be temporarily applied to a support substrate such as ruthenium and then transferred to another support substrate, and the application method is not limited. The photocurable resin of the present invention can also be used as a coating material or an adhesive, a molding material or the like. In the case of use as a coating or an adhesive, a composition containing a photocurable resin is applied onto a substrate, and then cured by irradiation with light. Further, when it is used as a molding material, the photocurable resin is poured into a mold having a space portion, and then irradiated with light to be cured. As the light source of the active light used for hardening, it is possible to use a light having a wavelength of 24 〇 to 41 〇 nm, for example, an ultrahigh pressure mercury lamp, a mercury vapor arc lamp, a carbon arc lamp, a xenon arc lamp, a metal hydride. Lights, etc. The irradiation amount of the active light, the irradiation time, and the like can be appropriately set depending on the photocurable resin to be used and the use. [Examples] Hereinafter, the present invention will be described in more detail by way of examples and examples, but the present invention is not limited to the examples and the like. [Example 1] Production of photocurable resin No. 1 To a four-necked flask equipped with a stirrer, a nitrogen gas introduction tube, a reflux cooling tube, and a thermometer, a bisphenol quinone type soil as a difunctional epoxy compound was added. Oxygen resin (epoxy equivalent: 23 1) 75.0 g, 23.8 g of unsaturated acid as unsaturated monobasic acid, 2,6-di-t-butyl-p-cresol 〇.273 g, tetrabutyl chlorinated money 0.585 g And propylene glycol_1_monomethyl ether-2-acetate 65 9 g, and mixed at 9 ° C for 1 hour 'and then at i00. Stir under the arm for 1 hour, then pour for 1 hour at uOt' then at 12 Torr. (: stirring for 14 hours to prepare component (C). Cold 146899.doc -34·201130868 But up to room temperature, a commercially available quantity of polyethylene having a number average molecular weight of 1 Å as a component (B) is added. Alcohol monomethyl ether (Uniox M_1000 manufactured by Nippon Oil Co., Ltd.) 55.6 g, 2,4-toluene diisocyanate 28 6 g as component (A), dibutyltin monolaurate 0.182 g, and propylene glycol_monomethyl ether 2 g acetate (206 g), and stirred at 70 ° C for 2 hours. Further, after cooling to room temperature, 3.57 g of diethylamine as a component (D) was added and stirred at room temperature for 2 hours. E. component succinic anhydride 1.63 g and after 4 hours of Tc mixing, the photocurable resin No. 1 of the target is obtained as a propylene glycol-1-monodecyl ether-2-acetate solution. (Mw=11500, Mn=5300, the amine value (solid content) is 15 mgKOH/g, and the acid value (solid content) is 5 mgK0H/g). Further, the photocurable resin No. 1 has the following structure. That is, one of the isocyanate groups of the component (A) is added to the ratio of the hydroxy hydrazine 丨 of the component (B) and the base of the component (C) of 0.83, and One of the ethylenically unsaturated groups of the component, the wheat is added in a ratio of 15 parts of the active hydroquinone of the component (D), and the anhydride structure of the polybasic acid anhydride (E) is further added to the remaining one. [Example 2] Production of photocurable resin Νο·2 <Step 1> 1,1-bis(4-hydroxyphenyl)indane synthesis in nitrogen Under the environment, a 2 L four-necked flask equipped with a stirring device, a nitrogen inlet tube, a reflux cooling tube and a thermometer was charged with 2 〇〇g of chlorinone and 855 g of benzene at a temperature below 40 ° C. 59.4 g of sulfuric acid and 16.1 g of 3-mercaptopropionic acid were added dropwise slowly. After the dropwise addition, the mixture was stirred at 55 ° C for 20 hours, and then 300 g of acetic acid and 300 g of aqueous sodium hydroxide solution were added for neutralization. The precipitated crystals gave 224 g of crude product. The crude product 146899.doc -35·201130868 was dissolved in ethyl acetate 1450 § and washed with 500 g of a 5 mass% aqueous ammonium acetate solution until the pH of the organic layer was After reaching 4 to 5, 5 g of anhydrous magnesium sulfate was added to the organic layer obtained by liquid separation, followed by drying. The solvent was distilled off, and 400 g of toluene was added for crystallization. The obtained crystal was dispersed and washed with toluene, and then vacuum dried at 4 Torr: to obtain 135 g of 1,1 -double (4 g) in white crucible. -Phenylphenyl)indan (yield in <Step 2> 1,1_bis[4_(2,3_epoxypropoxy)phenyl)indane in a nitrogen atmosphere, The 1,1-bis(4-hydroxyphenyl)indole obtained in the step 1 was added to a four-necked flask equipped with a stirring device, a nitrogen introducing tube, a refluxing cold, a P g and a 'severity a 2 L'. 29·2 g and epichlorohydrin 142 g were then added with 0.412 g of kakitriethylammonium chloride and stirred at 7 μc for 14 hours. Then, the temperature was lowered to 60 t: 16.1 g of a 48% by mass aqueous sodium hydroxide solution was added dropwise under a reduced pressure of 13,000 Pa, and then the epichlorohydrin which azeotroped with water was returned to the system while stirring for 2.5 hours. At the time when the azeotropy of water disappeared, the temperature was gradually lowered while depressurizing, and then K12 (the TC was distilled to remove epichlorohydrin for 2 hours. The pressure was returned to normal pressure, and 205 g of toluene was added and washed three times. The oil was separated. To the organic layer, a solution of 48 g of sodium hydroxide in an amount of 3,99 g of benzyl-ethylammonium chloride (0.412 g) and water (0.870 g) were added, followed by stirring at 8 °t for 2.5 hours. 0.692 g of aqueous sodium dihydrogen phosphate solution was neutralized and washed with water three times. The organic layer obtained by separating the oil and water was filtered, and the solvent was distilled off to obtain 36.6 g of M-double as a pale yellow viscous material. 4_(2,3_epoxypropoxy)phenyl]-supplement (yield 92% 'epoxy equivalent is 212). <Step 3> Manufacture of photocurable resin ν〇·2 146899.doc •36· 201130868 Add the 1,1_double [4- obtained as the difunctional epoxy compound in the four-necked flask of 500 mL with a stirring device, nitrogen inlet tube, reflux cooling tube and thermometer. (2,3-epoxypropoxy)phenyl]indane 3〇.〇g, as an unsaturated monobasic acid 1 〇·4 g of enoic acid, 0.120 g of tert-butyl-p-cresol, 256 g of tetrabutylammonium hydride, and 26.9 g of propylene glycol monomethyl ether 2_ acetate, at 9 (TC) After stirring for 1 hour, then k1 1 〇 5 χ: stirring for 1 hour, and then stirring at 12 (TC for 17 hours to prepare component (C). Cooling to room temperature 'added as a commercially available quantity of component (B) 22.9 g of polypropylene glycol monoterpene ether having a molecular weight of 〇1000, 12.0 g of 4,4,-dibenzoic acid diisocyanate as component (A), dibutyltin dilaurate 〇76 g, and propylene glycol-1-monomethyl 65.3 g of ether-2_acetate was stirred at 70 ° C for 2 hours. After cooling to room temperature, 2 83 layers of diethanolamine as a component (D) was added, and the mixture was stirred at a temperature for 2 hours, and added as e) The succinic anhydride of the component is 5.39 g and is scrambled at 40 C for 5 hours, and then the photocurable resin N 〇.2 (Mw) of the target is obtained in the form of a propylene glycol ___monomethyl sulphate-2-acetic acid vinegar solution. =5400,

Mn = 3i00 'the amine value (solid content) was 20 mgKOH/g, and the acid value (solid content) was 40 mgKOH/g). Further, the photocurable resin No. 2 has a structure in which one of the isocyanate groups of the component (A) has a base of 24 (b) and a basis of 0.76 of the component (C). After the ratio is added, the amount of the ethylenic unsaturated group (the one component of the component) and the amount of the active hydrogen group of the component (D) are 19, and the residual hydroxyl group is used. A structure in which the ratio of the acid anhydride structure of the polybasic acid anhydride (E) is 81 to be esterified. [Example 3] Production of photocurable resin N〇.3 146899.doc -37- 201130868 To the stirring device , a nitrogen-introducing tube, a reflux cooling tube, and a 500 mL four-necked flask of a thermometer were added as a difunctional epoxy compound, i _ bis[4·(2,3-epoxypropoxy)phenyl] 1-(4-biphenyl)-1-cyclohexyldecane (3⁄4•oxygen ϊ is 279) 33.0 g, as an unsaturated monobasic acid, 6.22 g of acrylic acid, 2,6-di-t-butyl 0.082 g of p-cresol, 0.153 g of tetrabutylammonium hydride and 10.5 g of propylene glycol-1-monomethyl ether-2-acetate were stirred at 901: for 1 hour, then at 100 ° C for 1 hour, then At 11 〇. (: stirring for 1 hour, and then stirring at 120 ° C for 17 hours to obtain a component (C). After cooling to room temperature, a commercially available number average molecular weight of 1 〇〇〇 as a component (B) was added. 16.9 g of monoterpene ether of alcohol/propylene glycol copolymer, 8.34 g of isophorone diisocyanate as component (A), 0.055 g of dibutyltin dilaurate, and propylene glycol-1-monodecyl ether-2-acetate 62.9 g Then, it was stirred at 70 ° C for 2 hours. After cooling to room temperature, 0.986 g of N-methyl piperene as component (D) was added and stirred at room temperature for 2 hours, and added as component (E). 1.50 g of tetrahydrophthalic anhydride and stirred at 4 ° C for 5 hours, and then obtained a photocurable resin No. of the target in the form of a propylene glycol-1 -monomethyl ether-2-acetate solution. 3 (Mw=13400, Mn=6500, amine value (solid content component): 20 mgKOH/g, acid value (solid content component): 1〇mgK〇H/g). Further, photocurable resin Νο·3 It has a structure in which one is added to the isocyanate group of the (Α) component, and the ratio of the hydroxy group of 23 components and the hydroxyl group of the component (C) is 0.77. One of the ethylenically unsaturated groups of the component (c) is added with a ratio of eight active hydrogen groups of the component (D), and further, with respect to the remaining hydroxyl groups, a polybasic acid anhydride (Ε) The structure of the acid anhydride structure 〇·16 is esterified. 146899.doc -38- 201130868 [Example 4] Production of photocurable resin ν〇·4 to a stirring device, a nitrogen introduction tube A bisphenol a-type epoxy resin (epoxy equivalent 186) as a difunctional epoxy compound was added to a four-liter four-necked flask of a reflux cooling tube and a thermometer. 75. 〇g, acrylic acid as an unsaturated monobasic acid 29.6 2,6-di-t-butyl-p-nonylphenol 0.321 g, tetrabutylammonium chloride 0.728 g, and propylene glycol-b-monodecyl ether-2-acetate 69 8 g at 12 Torr. [The mixture was stirred for 16 hours to prepare a component (C). To the room temperature, 69.7 g of a monodecyl ether of a commercially available ethylene glycol/propylene glycol copolymer having a number average molecular weight of 2 Å as a component (B), and 2,4-toluene as the component (A) were added. 26.0 g of diisocyanate vinegar, dibutyltin dilaurate 2 〇 ig, and 23 1 g of propylene glycol monomethicone-2-acetate, then stirred at 7 (TC for 2 hours) and then cooled to room temperature. Adding N 59-glycolic acid as a component to 3 59 g and stirring at room temperature for 2 hours to obtain a photocurable resin of the target in the form of a propylene glycol monomethyl ether-2 acetate solution. 4 (Mw=9500, Μη-5200, the amine value (solid content component) is 2〇mgKOH/g, and the acid value (solid content component) is 0 mgKOH/g). Further, the 'photocurable resin Νο·4 has the following The structure is obtained by adding one of the isocyanate groups of the (Α) component to the base of the (β) component and the base of the (C) component by a ratio of .88. One of the ethylenically unsaturated groups of the component is a structure in which the wheat is added in a ratio of nine active hydrogen hydrazines of the component (D). [Example 5] Photocurable resin Νο.5 Manufactured into a 500 mL four-necked flask equipped with a stirring device, a nitrogen inlet tube, a reflux cooling tube and a thermometer, was added as a difunctional epoxy compound. 146899.doc -39- 201130868 phenyl group Type epoxy resin (epoxy equivalent: 194) 50 g, acrylic acid as unsaturated monobasic acid 18_9 g, 2,6-di-t-butyl-p-cresol phenolphthalein 2〇9 g, tetrabutylammonium chloride 0.465 g And propylene glycol monomethyl ether-2_acetate 46 〇g, stirred at 90 C for 1 hour, then stirred at i 00 °c for 1 hour, then stirred at 110 ° for 1 hour, then at 12 〇. After stirring for 17 hours, the component (c) was prepared, and after cooling to room temperature, 32 7 g of a caprolactone 5 m〇i adduct of commercially available 2-hydroxyethyl acrylate as a component (B) was added as A) 2,4-toluene diisocyanate 157 g, dibutyltin dilaurate 118 g, and propylene glycol monomethyl ether-2-acetate 13 〇g, then stirred at 7 Torr for 2 hours, and then cooled to To the room temperature, 6.30 g of N-methyl piperene as the component (D) was added and stirred at room temperature for 2 hours to obtain propylene glycol monomethyl ether-2-acetic acid. The photocurable resin No. 5 (Mw = 4700, Mn = 27 〇 0 ' amine value (solid content)) of the target was 6 〇 mg K 〇 H / g, and the acid value (solid content) was obtained as a solution. Further, the photocurable resin No. 5 has a structure in which one of the isocyanate groups of the component (A) and the hydroxyl group of the (B) component are 27 and the hydroxyl group of the component (C). 73. The ratio of 73 is added to one of the ethylenically unsaturated groups of the component, and the structure is added by the ratio of the active hydroquinone of the component (D). [Example 6] Production of photocurable resin N〇.6 A binaphthol ring type as a difunctional epoxy compound was added to a 1 L four-necked flask equipped with a stirring device, a nitrogen gas introduction tube, a reflux cooling tube, and a thermometer. I Μ月日 (; epoxy reserve is 199) 3G.G g, as unsaturated-acidic acrylonitrile 11.1 g, 2,6-di-tert-butyl-p-phenol fluorene 124 g, tetrabutyl The base gasified ammonium 146899.doc •40·201130868 0.272 g and propylene glycol-b-monomethyl ether-2-acetate 27 4 g were stirred under i2〇〇c for 16 hours to prepare a component. To the room temperature, 19.6 g of a monomethyl ether of a commercially available ethylene glycol/propylene glycol copolymer having a number average molecular weight of 1 Å as a component (B), and 4,4'- as a component (A) were added. Benzophenone diisocyanate 17.6 g, dibutyltin dilaurate 0.078 g, and propylene glycol-1·monomethyl hydrazine-2-acetate 118 g, then 7 〇. Stir under the arm for 2 hours. Further, the mixture was cooled to room temperature, and dibutylamine 3 62 L as a component was added thereto, and the mixture was stirred at room temperature for 2 hours, and 2.10 g of hexahydrophthalic acid needle as the component (E) was added thereto at 40 ° C. After stirring for 5 hours, a photocurable resin N〇.6 of the target product was obtained in the form of a propylene glycol_丨_monomethyl ether-2-acetate solution (Mw=22000,

Mn = 8200, an amine value (solid content) of 20 mgKOH/g, and an acid value (solid content) of 1 〇 mgK 〇 H/g). Further, the photocurable resin No. 6 has a structure in which the ratio of the hydroxy group of the component (B) and the hydroxy group of the component (B) is 0 to 86, based on the isocyanate group of the component (A). After the addition, the amount of the ethylenic unsaturated group of the component (c) is increased by 0.19 of the active hydrogen of the component (D), and the amount of the remaining hydroxyl group is further The acid anhydride structure of the acid anhydride (e) has a structure in which the ratio of 46 is esterified.

[Evaluation Examples 1 to 6J The photocurable resins No. 1 to No. 6 obtained in Examples 丨 to 6 were evaluated in the following manner. <Evaluation of dispersibility> The photocurable resin N 〇 卜 N 〇 6 (solid content conversion) obtained in the above Example B was added to the pigment 1 〇 g of [Table 1]. 7_5 g, 146899.doc 201130868 Further, 32.5 g of propylene glycol-1-monodecyl ether-2-acetate was added. The mass of the dispersion obtained was 50 g. After premixing by a stirrer, dispersion treatment was carried out for 15 minutes in a range of 20 to 45 ° C by means of a planetary stirring device. As beads, 50 g of oxidized beads of 0.1 ηηηιΦ was added. The beads and the dispersion were separated by a weir to obtain pigment compositions No. 1 to No. 6, respectively. The evaluation of dispersibility was carried out by visually observing the dispersibility. When the slurry solution was uniformly dispersed to obtain a slurry solution, it was judged to be 〇, and aggregation or precipitation was judged as X. The results are shown in [Table 1]. <Evaluation of Photocurability> A coating liquid was prepared according to the following composition, and the obtained coating liquid was applied onto an aluminum substrate by a bar coater to a thickness of about 1 μm. After drying at 70 ° C for 15 minutes, the spectroscopic irradiation device CT-25CP manufactured by JASCO Corporation was used, and an ultrahigh pressure mercury lamp was used as a light source for exposure, followed by dipping in methyl ethyl ketone for 30 seconds, and then using two. The benzene was rinsed and the spectral sensitivity at 365 nm was measured. The sensitivity is determined by the amount of hardened film remaining on the aluminum plate and the amount of light emitted at 365 nm to determine the minimum hardening energy required for hardening at 365 nm. The results are shown in [Table 1]. (Composition) Pigment Composition No. 1 to No. 6 50.00 parts of polyether acrylate ("A-400" manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) 3.80 parts of polyacrylic acid urethane ("UN-made by Industrial Co., Ltd." -9000PEP") 1.90 parts of photopolymerization initiator ("Irg-907" by Ciba Specialty Chemicals Co., Ltd.) 1.10 parts of leveling agent ("BYK-323" by BYK-Chemie) 0_01 parts of propylene glycol-1-single Ethyl ether-2-acetate 43.19 parts 146899.doc • 42-201130868 <Adhesion evaluation> The coating liquid prepared above was applied to PET by a bar coater (p〇lyethyiene terephthalate, polyparaphenylene) The ethylene glycol formate film (A4300 manufactured by Toyobo Co., Ltd.) was coated on each of them! The thickness of μιη. After drying the shovel at 7 〇 Qc, the belt was irradiated with ultraviolet rays to obtain a coating using a conveyor belt type ultraviolet ray irradiator to reach 18 〇 mJ/cm 2 . The adhesion is adhered to the transparent adhesive tape manufactured by Nichiban Co., Ltd., and peeled off, and the degree of peeling is visually observed. The person who has almost no peeling of the film is judged as 〇, and a part of the tarnished film is judged as △, Most of the film peeling is judged as X. The results are shown in [Table 1]. [Comparative Evaluation Examples 1 to 3] The same operations as in the above Evaluation Examples 1 to 3 were carried out, except that the photocurable resin N〇 J to n〇.3 was not added. The results are shown in [Table]. [Comparative Evaluation Examples 4 to 7] The same as the above-mentioned evaluation examples 4 to 6 except that the commercially available dispersing agent shown in [Table 1] was added instead of the photocurable tree q Ν〇 4 4 to Ν . 6. operating. The results are shown in [Table 1]. 146899.doc -43· 201130868 [Table i]

Pigment Composition Pigment Dispersibility Photocuring Property (mJ/cm) Adhesion Evaluation Example 1 No. 1 Pigment Red 254 〇 4.8 〇 Evaluation Example 2 No. 2 Pigment Green 7 〇 15 〇 Evaluation Example 3 No. 3 Pigment Blue 15 〇 86 〇 Evaluation Example 4 No. 4 Pigment Violet 19 〇 ^ 0.8 〇 Evaluation Example 5 No. 5 Pigment Yellow 1 〇 153 Δ Evaluation Example 6 No. 6 Pigment Green 7 〇 15 〇 Comparative Evaluation Example 1 No Pigment Red 254 X Comparative Evaluation Example 2: Pigment Green 7X Comparative Evaluation Example 3 Pigment Free Blue 15 X Comparative Evaluation Example 4 Commercial Dispersant No. Γ1 Pigment Red 254 〇153 X Comparative Evaluation Example 5 Commercial Dispersant No. 2t2 Pigment Green 7 〇 153 X Comparative Evaluation Example 6 Commercial dispersant Nof3 Pigment Blue 15 〇 > 859 X Comparative Evaluation Example 7 Commercial Dispersant No. 4 Pigment Red 254 〇 859 X Wood 1: BYK-Chemie Co., Ltd. "ΒΥΚ-163" Wood 2 : "ΒΥΚ-164" manufactured by BYK Chemie. Wood 3: "EFKA-4046" manufactured by Ciba Specialty Chemicals Co., Ltd. * 4 : "Solsperse 3000" manufactured by Zeneca Co., Ltd. According to the results of [Table 1], the following items can be clarified. The pigment composition using the photohardenable resin of the present invention has the same dispersibility as the pigment composition using a commercially available dispersant. Further, the coating liquid obtained by using the pigment composition of the photocurable resin of the present invention has photocurability and photohardening at the time of coating with a coating liquid obtained by using a pigment composition of a commercially available dispersant. The adhesion to the substrate is higher afterwards. 146899.doc 44-

Claims (1)

201130868 VII. Patent application scope: 1. A photocurable resin which has an average of two or two hydroxyl groups in the same molecule and a number average molecular weight of 300 to 5000 by adding a p-diisocyanate compound (A). After the compound (B) and the compound (C) having two hydroxyl groups and two ethylenically unsaturated groups in the same molecule, the wheat can be added to the compound (D) having an active hydrogen and a tertiary amino group in the same molecule. . 2. The photocurable resin according to claim 1, wherein the compound (c) having two light groups and two ethylenically unsaturated groups in the same molecule is a difunctional epoxy ruthenium compound and (meth)acrylic acid. Adult. 3. The photocurable resin according to claim 2, wherein the difunctional epoxide is a compound represented by the following formula (I): [Chemical Formula 1] (wherein Μ represents a direct bond, an alkylene group having an atomic number, an alicyclic group, 0, S, S02, SS, so 'CO, oco or selected from the group consisting of the following [Chemical 2] The substituent of the group may be substituted by a dentate atom, and R1 and R2 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, and carbon. The alkenyl group having an atomic number of 2 to 5 or an imine atom 'and the alkyl group, the alkoxy group and the alkenyl group may be substituted by a _ atomic atom 'R1 and R2 may be bonded to each other to form a ring structure, and η is an integer). 146899.doc 201130868 [Chemical 2] Q and B each independently represent a hydrogen atom... from 〜 or < '« π 外丁双为1〜ίο的 alkyl or a carbon atom number 丨~1〇 alkoxy substituted phenyl or 妷 atomic number It is a cycloalkyl group of 3 to 10, and hydrazine and hydrazine each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or a county having 2 to ί. Atom, money, alkoxy, and dilute groups may also be substituted by a (a) atom. ' A&D independently represents a carbon atom which can be substituted by a (iv) atom and a carbon which can be substituted by a _ atom. An aryl group having 6 to 20 atoms, a carbon atom having a (tetra) atom substitution of ～4), a hetero atom group having a carbon atom number of 2 to 2 取代 substituted by a (tetra) atom, or a functional atom, And 嗲煊 — . . 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫 泫The ring may be an aromatic ring, and r3 represents an atom, an alkyl group having a carbon number of 5, a carbon primordyl group, a cation group having a carbon number of 2 to 5, or a dentate atom and an alkoxy group of 8 And the base can also be expressed by the element of the element (4), the surface of the table η, the number of ρ~5, k 4. the number, a means the number of 〇~4, d means the number of 〇~4). The photocurable resin of claim 2 or 3, 1 /, T, the above-mentioned difunctional epoxidation 146899.doc 201130868 is a compound represented by the following formula (II): [Chemical 3] CU) (wherein η and p are the same as the above formula (1)). The photocurable resin according to claim 2 or 3, wherein the difunctional epoxide is a compound represented by the following formula (III): [Chemical 4] «!〇 〇 (wherein, R1, R2 and η are the same as in the above formula (I)). 6. The photocurable resin according to claim 2, wherein the difunctional epoxide is a compound represented by the following formula (IV): 146899.doc (IV) 201130868 (wherein R R , VIII, 1), &, 4 and 11 are the same as in the above formula (1). 7. The photocurable resin according to claim 2, wherein the difunctional epoxide is a compound represented by the following formula (V): [Chem. 6] (wherein R4 and R5 each independently represent a hydrogen atom, an alkyl group having 5 carbon atoms, an alkoxy group having 8 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or a dentate atom, and The alkyl group, the alkoxy group and the alkenyl group may be substituted by a halogen group, and R4 and R5 may be bonded to each other to form a ring structure, and η is the same as the above formula (I). 8. The photocurable resin according to any one of claims 1 to 3 or 7, which has a mass average molecular weight of 1 〇〇〇 to 5 聚苯乙烯 in terms of polystyrene measured by SEC (SiZe Exclusion Chromatography). Hey. A photocurable resin obtained by esterifying a photocurable resin according to any one of the claims to the formula "3" to a polybasic acid anhydride (E). A dispersant which is an active ingredient of the photocurable resin as claimed in any one of claims 1 to 9. 146899.doc 201130868 IV. Designated representative map (1) The representative representative of the case is: (none) (2) The symbolic symbol of the representative figure is simple: 5. If there is a chemical formula in this case, please reveal the characteristics that can best show the invention. Chemical formula: (none) 146899.doc -2-