WO2012121179A1 - β-HYDROXYALKYLAMIDE ET COMPOSITION DE RÉSINE - Google Patents

β-HYDROXYALKYLAMIDE ET COMPOSITION DE RÉSINE Download PDF

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WO2012121179A1
WO2012121179A1 PCT/JP2012/055480 JP2012055480W WO2012121179A1 WO 2012121179 A1 WO2012121179 A1 WO 2012121179A1 JP 2012055480 W JP2012055480 W JP 2012055480W WO 2012121179 A1 WO2012121179 A1 WO 2012121179A1
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group
acid
compound
parts
hydrocarbon group
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PCT/JP2012/055480
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Japanese (ja)
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直宏 ▲濱▼田
菅野　真樹
純平 早川
彩子 宮本
進 白鳥
知 宮下
雅則 野城
貴志 狩野
慶一 近藤
桑原　章史
綾子 冨田
佳奈子 水野
水嶋　克彦
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東洋インキＳｃホールディングス株式会社
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Priority to CN201280011606.4A priority Critical patent/CN103402975B/zh
Priority to KR1020137024623A priority patent/KR101930048B1/ko
Publication of WO2012121179A1 publication Critical patent/WO2012121179A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
    • C07C235/74—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/20—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/21—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of an unsaturated carbon skeleton containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/60—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/69—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C08L101/06—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
    • C08L101/08—Carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
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    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
    • C07C2602/28—Hydrogenated naphthalenes
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    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Definitions

  • the present invention relates to ⁇ -hydroxyalkylamide and a resin composition containing the same.
  • the present invention also relates to a photosensitive resin composition.
  • the present invention relates to a color filter, a black matrix, a color filter protective film, a photo spacer, a protrusion for liquid crystal alignment, a microlens, an insulating film for a touch panel, a flexible printed wiring board, which is used for a color liquid crystal display device, a color image pickup tube element, etc.
  • the present invention relates to a resin composition for an electronic component used for an adhesive for electronic materials, an adhesive sheet, and the like in the vicinity.
  • a crosslinking agent having a functional group capable of reacting with the carboxyl group is used.
  • the functional group include an isocyanate group, a blocked isocyanate group, an epoxy group, and a ⁇ -hydroxyalkylamide group.
  • the isocyanate group and the carboxyl group are said to react at 130 ° C. or higher.
  • the isocyanate group is more reactive with the OH group, water, and alcohol in the resin, when using an alcohol as a solvent or when using a solvent containing water, the carboxyl group and It cannot be used because it reacts with water and alcohol before reacting.
  • long-term storage after blending also reacts with moisture in the air, it is difficult to make a single solution.
  • blocked isocyanate is used in order to solve the above-mentioned problems
  • the physical properties may be adversely affected by the blocking agent remaining in the cured product.
  • the blocking agent there is a concern that the blocking agent is scattered in the air at the time of heat curing, which adversely affects the operator or the environment. Even when using an alcoholic solvent with a boiling point higher than the temperature at which the blocking agent comes off and hardens, it reacts with the alcoholic solvent prior to the carboxyl group contained in the resin. Can not.
  • the crosslinking agent having an epoxy group is widely used for crosslinking a resin having a carboxyl group along with the isocyanate, and many types are commercially available.
  • There is no by-product in the reaction of the epoxy group and the carboxyl group and it is considered that no adverse effect such as a blocking agent for blocked isocyanate occurs.
  • the reaction does not proceed so much without a catalyst, but it can be cured at a temperature of 150 ° C. or lower by adding a tertiary amine or a quaternary ammonium salt as a catalyst.
  • the reaction proceeds little by little at room temperature due to the influence of the catalyst to be added, and the storage stability is poor.
  • ⁇ -hydroxyalkylamide is also a crosslinking agent that reacts with a carboxyl group (Patent Document 1).
  • the only by-product during the reaction is water, and there is little effect on the cured product, and there is a merit that there is no effect on the worker or the environment. Further, it can be cured at 150 ° C.
  • Examples of ⁇ -hydroxyalkylamides currently available on the market include Primid XL-552 manufactured by Ems Chemie, which is mainly used as a crosslinking agent for powder coatings (Patent Document 2).
  • Patent Document 4 an example in which a photosensitive composition is combined with a resin containing a photopolymerizable functional group (Patent Document 4), or an example in which a photopolymerizable functional group is added to ⁇ -hydroxyalkylamide to form a photosensitive composition (
  • ⁇ -hydroxyalkylamide is poorly soluble in the composition and does not become a uniform coating agent. There has been a problem that the optical properties are lowered and the optical properties are lowered.
  • the present invention has been made in view of the above situation, and an object thereof is to provide ⁇ -hydroxyalkylamides that are soluble in organic solvents. Moreover, it aims at providing the resin composition containing this and the photosensitive resin composition.
  • An embodiment of the present invention relates to a compound represented by the following formula (1).
  • X represents an n-valent group consisting of carbon, hydrogen, nitrogen, oxygen, sulfur, or halogen
  • n is an integer from 2 to 6
  • R 1 and R 2 are each independently a hydrogen atom, a group represented by the following formula (2), a group represented by the following formula (3), an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, Or an aromatic hydrocarbon group, and at least one of one or more R 1 and R 2 bonded to one or more nitrogen atoms is a group represented by the following formula (2), and at least one is It is group represented by following formula (3).
  • R 3 to R 6 each independently represents a hydrogen atom, a hydrocarbon group, or a hydrocarbon group substituted with a hydroxyl group
  • R 7 represents a compound having a functional group capable of reacting with a hydroxyl group. Represents a residue.
  • the compound having a functional group capable of reacting with the hydroxyl group may be an isocyanate, a carboxylic acid, a carboxylic acid halide, or a carboxylic acid anhydride.
  • the compound having a functional group capable of reacting with the hydroxyl group may be a monofunctional isocyanate or a monofunctional carboxylic acid.
  • R 7 in Formula (3) may be represented by the following Formula (9) or Formula (10).
  • R 16 is: a single bond; a (m 1 +1) -valent hydrocarbon group; or at least one of a urethane bond, a urea bond, an allophanate bond, a biuret bond, and an isocyanurate ring, a carbon atom, and a hydrogen atom.
  • (M 1 +1) valent group consisting of A 1 represents a single bond, a urethane bond or a urea bond
  • R 17 represents a divalent hydrocarbon group
  • a 2 represents an ether bond or an ester bond
  • R 18 represents a monovalent hydrocarbon group
  • m 1 represents an integer of 1 to 5
  • p 1 represents an integer of 0 to 100.
  • R 19 represents a single bond; a (m 2 +1) valent hydrocarbon group; or a (m 2 +1) valent group consisting of a carbon atom, a hydrogen atom and an oxygen atom,
  • a 3 represents a single bond or an ester bond
  • R 20 represents a divalent hydrocarbon group
  • a 4 represents an ether bond or an ester bond
  • R 21 represents a monovalent hydrocarbon group
  • m 2 represents an integer of 1 to 5
  • p 2 represents an integer of 0 to 100.
  • the compound having a functional group capable of reacting with the hydroxyl group may be a compound represented by the following formula (4), formula (5), or formula (6).
  • R 8 is a linear, cyclic or branched saturated or unsaturated hydrocarbon group having 2 to 18 carbon atoms.
  • R 9 is a hydrogen atom or a methyl group
  • R 10 is a linear or branched alkylene group having 2 to 8 carbon atoms, a divalent alicyclic hydrocarbon group, or an aromatic hydrocarbon group
  • R 11 is a linear or branched alkylene group having 2 to 8 carbon atoms, a divalent alicyclic hydrocarbon group, or an aromatic hydrocarbon group.
  • R 12 is a hydrogen atom or a methyl group
  • R 13 is a group represented by the following formula (7) or formula (8).
  • n 1 is an integer of 1 to 2.
  • R 14 is a linear or branched alkylene group having 2 to 8 carbon atoms, a divalent alicyclic hydrocarbon group, or an aromatic hydrocarbon group
  • R 15 is a group having 6 to 13 carbon atoms.
  • the atom in X that is directly bonded to the carbonyl group in formula (1) may be a carbon atom that is not included in the aromatic ring.
  • X in the formula (1) may be an n-valent aliphatic hydrocarbon group or alicyclic hydrocarbon group having 6 or more carbon atoms.
  • an embodiment of the present invention relates to a resin composition containing the compound represented by the above formula (1), a resin having a carboxyl group, and an organic solvent.
  • the resin composition may be a photosensitive resin composition containing a photopolymerization initiator and / or a photopolymerizable monomer.
  • the compound represented by the formula (1) may further have a photopolymerizable double bond.
  • the embodiment of this invention is related with the resin composition for electronic components containing the compound represented by following formula (1), and resin which has a carboxyl group.
  • X represents an n-valent group consisting of carbon, hydrogen, nitrogen, oxygen, sulfur, or halogen
  • n is an integer from 2 to 6
  • R 1 and R 2 are each independently a hydrogen atom, a group represented by the following formula (2), a group represented by the following formula (3), an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, Or an aromatic hydrocarbon group, Among one or more R 1 and R 2 bonded to one or more nitrogen atoms, at least one is a group represented by the following formula (2), and at least one is represented by the following formula (3). The group.
  • R 3 to R 6 each independently represents a hydrogen atom, a hydrocarbon group, or a hydrocarbon group substituted with a hydroxyl group
  • R 7 represents a residue or hydrogen of a compound capable of reacting with a hydroxyl group. Represents.
  • the above embodiment includes the following embodiments (1) to (4).
  • R is a residue of a compound capable of reacting with a hydroxyl group
  • X is a (m + n) -valent group excluding the hydroxyl group of ⁇ -hydroxyalkylamide
  • m and n are integers of 1 or more
  • (2) (b-1) a compound obtained by reacting a divalent or higher carboxylic acid or derivative thereof with (b-2) a primary or secondary amine having one or more hydroxyl groups at the ⁇ -position, And (B) ⁇ -hydroxyalkylamide, which is soluble in an organic solvent.
  • a photosensitive composition comprising ⁇ -hydroxyalkylamide (A) that is soluble in an organic solvent, a polymer (B) containing a carboxyl group, and a photopolymerization initiator (C).
  • a photosensitive composition comprising a photopolymerizable functional group as an essential component in the composition.
  • X represents an n-valent straight-chain aliphatic hydrocarbon having 6 or more carbon atoms or an alicyclic hydrocarbon group
  • n is an integer of 2 to 6
  • R 1 and R 2 are Each independently represents a hydrogen atom, a group represented by formula (c), an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, or an aromatic hydrocarbon group, and at least one of R 1 and R 2 ; Is a group represented by the formula (c).
  • R 3 to R 6 each independently represents a hydrogen atom or an aliphatic hydrocarbon group.
  • ⁇ -hydroxyalkylamides that are soluble in organic solvents can be provided. Further, according to the resin composition and the photosensitive composition containing the same, it is possible to form a film or a fine pattern that satisfies heat resistance, chemical resistance, smoothness, and optical characteristics.
  • FIG. 1 is an IR spectrum of the ⁇ -hydroxyalkylamide of Example 1 for embodiment I.
  • FIG. 2 is a 1H-NMR spectrum of compound 2 of Example 2 for embodiment II. (In heavy dimethyl sulfoxide solvent)
  • FIG. 3 is an IR spectrum of compound 2 of Example 2 for embodiment II.
  • FIG. 4 is the 1H-NMR spectrum of Example 2 for embodiment I.
  • FIG. 5 is the 1H-NMR spectrum of Example 3 for embodiment I.
  • FIG. 6 is the 1H-NMR spectrum of Example 4 for embodiment I.
  • FIG. 7 is the 1H-NMR spectrum of Example 3 for embodiment II.
  • FIG. 8 is a 1H-NMR spectrum of Synthesis Example 27 relating to embodiment IV.
  • (meth) acrylate means acrylate and / or methacrylate
  • (meth) acrylic acid means acrylic acid and / or methacrylic acid.
  • ⁇ -Hydroxyalkylamide (A)> ⁇ -hydroxyalkylamide (A) is a compound represented by the formula (1), wherein X represents an n-valent group composed of carbon, hydrogen, nitrogen, oxygen, sulfur, or halogen. n is an integer of 2 to 6. Specific examples of X include an n-valent aliphatic hydrocarbon group having 2 or more carbon atoms, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group having a hetero atom.
  • halogen examples include fluorine, chlorine, bromine, iodine and the like, and fluorine is preferable from the viewpoint of transparency. From the viewpoint of imparting flame retardancy, chlorine and bromine are preferred.
  • n-valent group is a group obtained by removing n hydrogen atoms from a compound. Hereinafter, this is referred to as an n-valent group derived from the compound.
  • n-valent aliphatic hydrocarbon group examples include n-valent groups derived from alkanes, alkenes, and alkynes.
  • Alkanes include ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, heptadecane, hexadecane, octadecane, nonadecane, icosane, heicossan, docosane, isobutane, isopentane, Neopentane, methylpentane, dimethylpentane, ethylmethylpentane, diethylpentane, methylhexane, tetramethylheptane, and the like.
  • n-valent group derived from alkane examples include 1,6-hexyl group, 1,7-heptyl group, 1,8-octyl group, 1,9-nonyl group, 1,10-decyl group, 1,11 -Undecyl, 1,12-dodecyl, 1,13-tridecyl, 1,14-tetradecyl, 1,15-pentadecyl, 1,16-hexadecyl, 1,17-heptadecyl, 1,18- Octadecyl group, 1,19-nonadecyl group, 1,3,6-hexyl group, 1,4,7-heptyl group, 1,2,8-octyl group, 1,3,9-nonyl group, 1,3, Examples include 4,6-hexyl group, 1,4,6,7-heptyl group, 1,4,5,6,7-heptyl group and 1,2,3,4,5,6-hexyl group.
  • Alkenes include ethylene, propylene, butylene, pentene, hexene, heptene, octene, nonene, decene, undecene, docene, tridecene, tetracene, pentadecene, heptadecene, hexadecene, octadecene, nonadecene, icosene, heicocene, dococene, methylpentene, etc. Is mentioned.
  • n-valent groups derived from alkenes include 1,6- (2-hexenyl) group, 1,7- (2-heptenyl) group, 1,8- (2-octenyl) group, 1,9- (2-nonenyl) group, 1,10- (2-decenyl) group, 1,11- (2-undecenyl) group, 1,12- (2-dodecenyl) group, 1,13- (2-tridecenyl) group 1,14- (2-tetradecenyl) group, 1,15- (2-pentadecenyl) group, 1,16- (2-hexadecenyl) group, 1,17- (2-heptadecenyl) group, 1,18- ( 2-octadecenyl) group, 1,19- (2-nonadecenyl) group, 1,3,6- (2-hexenyl) group, 1,4,7- (3-heptenyl) group, 1,2,8- ( 4-octen
  • alkynes examples include ethyne, propyne, butyne, pentyne, hexyne, peptin, octyne, nonin, decyne, undecine, dodecin, tridecine, icosin, henicosin, docosin, and the like.
  • n-valent group derived from alkyne examples include 1,6- (2-hexynyl) group, 1,7- (2-hepsinyl) group, 1,8- (2-octynyl) group, 1,9- (2-nonyl) group, 1,10- (2-decynyl) group, 1,11- (2-undecynyl) group, 1,12- (2-dodecynyl) group, 1,13- (2-tridecynyl) group 1,14- (2-tetradecynyl) group, 1,15- (2-pentadecynyl) group, 1,16- (2-hexadecynyl) group, 1,17- (2-heptadecynyl) group, 1,18- ( 2-octadecynyl) group, 1,19- (2-nonadecynyl) group, 1,3,6- (2-hexynyl) group, 1,4,7- (3-hep
  • n-valent alicyclic hydrocarbon groups include cyclopropane, cyclobutane, cyclopentane, methylcyclopentane, dimethylcyclopentane, trimethylcyclopentane, cyclohexane, methylcyclohexane, dimethylcyclohexane, cyclohexene, methylcyclohexene, norbornane, norbornene, bicyclo And n-valent groups derived from octene, decahydronaphthalene, adamantane, dimethyladamantane, and the like.
  • n-valent aromatic hydrocarbon groups examples include n-valent aromatic hydrocarbon groups derived from benzene, naphthalene, biphenyl, anthracene, toluene, xylene, ethylbenzene, tert-butylbenzene, diphenylethane, diphenylacetylene, 9,9-diphenylfluorene, and the like.
  • examples of the group in which an aromatic ring contains a carbon atom bonded to a carbonyl group include a phenylene group and a tolylene group.
  • Examples of the group in which the carbon atom bonded to the carbonyl group is not contained in the aromatic ring include toluene- ⁇ , ⁇ -diyl group, ethylbenzene- ⁇ , ⁇ -diyl group, ethylbenzene- ⁇ , ⁇ -diyl group, 1,2-diphenyl And ethane-1,2-diyl group.
  • N-valent groups having heteroatoms include ethanol, ethylene glycol, ethylene diacetate, ethylene dipivalate, ethylene dibenzoate, ethylene bis (methyl benzoate), ethylene bis (methoxy Benzoate), propanol, isopropanol, ethyl acetate, erythritol, ethylene oxide, acetaldehyde, acetone, dipropyl ketone, ⁇ -pentadecanolactone, 1,2-cyclohexane, ⁇ -butyrolactone, ethylamine, ethylmethylamine, propylamine, N- Propylacetamide, ethanethiol, ethanedithiol, tetrafluoroethane, dibromoethane, hexafluoropropane, octofluorobutane, dodecafluorohexane, hex
  • the atom in X that is directly bonded to the carbonyl group is a carbon atom that is not included in the aromatic ring.
  • a straight chain aliphatic hydrocarbon group having 6 to 18 carbon atoms or an alicyclic hydrocarbon group is preferable, and a straight chain aliphatic hydrocarbon group having 6 to 12 carbon atoms is more preferable, or It is an alicyclic hydrocarbon group, and more preferably a linear aliphatic hydrocarbon group having 6 to 12 carbon atoms.
  • R 1 and R 2 are each independently a hydrogen atom, a group represented by the formula (2), a group represented by the formula (3), an aliphatic hydrocarbon group, an alicyclic hydrocarbon group. Or an aromatic hydrocarbon group, and at least one of one or more R 1 and R 2 bonded to one or more nitrogen atoms is a group represented by the formula (2), and at least one is It is group represented by Formula (3).
  • Examples of the aliphatic hydrocarbon group include an alkyl group, an alkenyl group, and an alkynyl group.
  • alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, decyl , Dodecyl group, pentadecyl group, and octadecyl group.
  • Alkenyl groups include vinyl, 1-propenyl, 2-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-octenyl, 1-decenyl, 1-octadecenyl Groups.
  • alkynyl group examples include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-octynyl group, 1-decynyl group and 1-octadecynyl group. .
  • alicyclic hydrocarbon groups include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclooctadecyl group, 2-indeno group, decahydronaphthyl group, adamantyl group, dicyclopenta And a cycloalkyl group such as a nyl group.
  • aromatic hydrocarbon group examples include a single ring, a condensed ring, and a ring assembly aromatic hydrocarbon group.
  • Examples of the monocyclic aromatic hydrocarbon group include monocyclic aromatic groups such as phenyl group, benzyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,4-xylyl group, p-cumenyl group, and mesityl group.
  • Group hydrocarbon group examples include monocyclic aromatic groups such as phenyl group, benzyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,4-xylyl group, p-cumenyl group, and mesityl group.
  • Group hydrocarbon group examples include monocyclic aromatic groups such as phenyl group, benzyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,4-xylyl group, p-cumenyl group, and mesityl group.
  • the condensed ring aromatic hydrocarbon group includes 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 5-anthryl group, 1-phenanthryl group, 9-phenanthryl group, 1-acenaphthyl group, Examples thereof include condensed ring aromatic hydrocarbon groups such as 2-azurenyl group, 1-pyrenyl group and 2-triphenylyl group.
  • ring-assembled aromatic hydrocarbon group examples include ring-assembled aromatic hydrocarbon groups such as o-biphenylyl group, m-biphenylyl group, and p-biphenylyl group.
  • R 1 and R 2 other than those represented by formula (2) and formula (3) are preferably aliphatic hydrocarbon groups, alicyclic hydrocarbons, or monocyclic aromatic hydrocarbon groups, and more preferably An aliphatic hydrocarbon group or an alicyclic hydrocarbon, and more preferably an aliphatic hydrocarbon group having 4 or more carbon atoms.
  • R 3 to R 6 in the groups represented by the formulas (2) and (3) each independently represent a hydrogen atom, a hydrocarbon group, or a hydrocarbon group substituted with a hydroxyl group
  • R 7 represents Represents a residue or hydrogen of a compound having a functional group capable of reacting with a hydroxyl group.
  • hydrocarbon groups are the same as those described above for R 1 and R 2 .
  • examples of the hydrocarbon group substituted with a hydroxyl group include a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a hydroxyphenyl group, a hydroxycyclohexyl group, and the like.
  • the residue of the compound having a functional group capable of reacting with a hydroxyl group is not particularly limited, but isocyanate, carboxylic acid, carboxylic acid halide, carboxylic acid anhydride, carboxylic acid ester, silanol, alkoxysilane, silanol ester, amino Examples thereof include resins, compounds having an epoxy, and the like, and isocyanates, carboxylic acids, carboxylic acid halides, and carboxylic anhydrides are preferable, and monofunctional isocyanates or monofunctional carboxylic acids are more preferable.
  • R 7 in formula (3) is more preferably represented by the formula (9). Moreover, since photocurability becomes favorable, it is preferable to use the compound represented by Formula (6).
  • R 7 in formula (3) is more preferably represented by formula (10). Moreover, since it is easy to provide the solubility to an organic solvent, it is preferable to use the compound represented by Formula (4), and since photocurability becomes favorable, it is represented by Formula (5). It is preferable to use a compound.
  • the resin composition containing the compound represented by the formula (1) is used for, for example, a coating agent for a touch panel interlayer insulating film or a photosensitive composition for a color filter, chemical resistance, heat resistance, and hardness are improved. Therefore, it is preferable that at least one of X, R 1 and R 2 contains a photopolymerizable functional group.
  • X in the above formula (1) is A hydrocarbon group having 6 or more carbon atoms is preferred.
  • R 7 has a functional group capable of reacting with a hydroxyl group: [1] (a-1) formed by amidation of a divalent or higher carboxylic acid or derivative thereof and (a-2) a primary or secondary amine having one or more hydroxyl groups at the ⁇ -position (a- 3) A part of the hydroxyl group of ⁇ -hydroxyalkylamide is reacted with a compound having (a-4) one or more functional groups capable of reacting with the hydroxyl group.
  • (a-2) A compound having one or more functional groups capable of reacting with a hydroxyl group by protecting the amino group of a primary or secondary amine having one or more hydroxyl groups at the ⁇ -position React. After removing the protecting group of this compound, (a-1) amidation with a divalent or higher carboxylic acid or derivative thereof is performed.
  • the above method [1] is preferable.
  • (a-3) ⁇ -hydroxyalkylamide is available, (a-1) a divalent or higher carboxylic acid or derivative thereof and (a-2) 1 having one or more hydroxyl groups at the ⁇ -position (A-3) a compound having at least one functional group capable of reacting with a hydroxyl group as a part of the hydroxyl group of (a-3) ⁇ -hydroxyalkylamide without undergoing a reaction of a secondary or secondary amine; The method of making it react may be sufficient.
  • R 7 is a hydrogen atom: [4] Amidation of (a-1) a divalent or higher carboxylic acid or derivative thereof and (a-2) a primary or secondary amine having one or more hydroxyl groups at the ⁇ -position.
  • ⁇ -hydroxyalkylamide may or may not contain a photopolymerizable functional group.
  • A-1) a divalent or higher carboxylic acid or derivative thereof,
  • (a-2) a primary or secondary amine having one or more hydroxyl groups at the ⁇ -position, or
  • (a-4) a functional group capable of reacting with a hydroxyl group
  • a photopolymerizable functional group can be introduced by using a compound containing a photopolymerizable functional group as a compound having one or more groups. From the viewpoint of stability during synthesis, it is preferred that (a-4) a compound having one or more functional groups capable of reacting with a hydroxyl group contains a photopolymerizable functional group.
  • the divalent or higher carboxylic acids include the following. (Hereinafter, “” is used to indicate an alias for the same compound.)
  • Linear saturated aliphatic dicarboxylic acids oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid , Pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, Branched saturated aliphatic dicarboxylic acids: methylmalonic acid,
  • carboxylic acid derivatives include acid anhydrides, acid chlorides, acid bromides, methyl esters, ethyl esters, phenyl esters, and tert-butyl esters of the above carboxylic acids.
  • Examples of compounds having one or more functional groups capable of reacting with a hydroxyl group include isocyanate, carboxylic acid, carboxylic acid halide, carboxylic acid anhydride, carboxylic acid ester, silanol, alkoxysilane, silanol ester, Examples thereof include amino resins and compounds having an epoxy.
  • an isocyanate group, a carboxyl group, a carboxylic acid anhydride group, and a carboxylic acid halide group are particularly preferable, and a carboxyl group and an isocyanate group are more preferable.
  • isocyanates examples include the following.
  • Monofunctional isocyanate methyl isocyanate, butyl isocyanate, hexyl isocyanate, heptyl isocyanate, lauryl isocyanate, stearyl isocyanate, phenyl isocyanate, cyclopropyl isocyanate, phenethyl isocyanate, tosyl isocyanate, acryloyloxyethyl isocyanate, methacryloyloxyethyl isocyanate, vinyl isocyanate, allyl isocyanate 2- (2-acryloyloxyethyloxy) ethyl isocyanate, 2- (2-methacryloyloxyethyloxy) ethyl isocyanate, 1,1-bis (acryloyloxymethyl) ethyl isocyanate, 1,1-bis (methacryloyloxymethyl) Ethyl isocyanate, Bifunctional isocyanates: tolylene diisocyanate, di
  • the above monofunctional isocyanate or one of the polyfunctional isocyanate or biuret of polyfunctional isocyanate, uretdione, isocyanurate, adduct It is preferable to use a monofunctional isocyanate which is obtained by leaving a group and reacting the remainder with an active hydrogen compound.
  • Examples of the carboxylic acid that is, the compound having a carboxy group include the following.
  • Aliphatic saturated monofunctional carboxylic acids formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid ⁇ pentanoic acid>, 2-methylbutyric acid, isovaleric acid ⁇ 3-methylbutyric acid>, pivalic acid ⁇ 2,2-dimethyl Propionic acid, caproic acid, hexanoic acid, methylvaleric acid, dimethylbutyric acid, ethylbutyric acid, enanthic acid, heptanoic acid, caprylic acid, octanoic acid, 2-ethylhexanoic acid, pelargonic acid, nonanoic acid, capric acid ⁇ decanoic acid >>, undecanoic acid, lauric acid ⁇ dodecanoic acid >>, tridecanoic acid, myristic acid ⁇ tetradecanoic acid >>, pentadecanoic acid, palmitic acid ⁇ hexade
  • a compound having a carboxyl group is a part of a compound mentioned as a divalent or higher carboxylic acid or derivative thereof with alcohol or amine. Also included are esterified and amidated compounds.
  • Silanol is a compound having a Si—OH structure in the molecule, and OH in the silanol reacts with a hydroxyl group. Further, alkoxysilane, sulfuric acid of silanol, sulfonic acid ester, and halogenated silane (hereinafter collectively referred to as “silanol derivatives”) generate silanol by hydrolysis, and thus can be used in the same manner as silanol.
  • a silanol derivative is commercially available from the viewpoint of storage stability.
  • silanol derivatives examples include the following.
  • Monofunctional silanol derivatives trimethylsilyl triflate, triethylsilyl triflate, tert-butyldimethylsilyl triflate, diethylisopropylsilyl triflate, tripropylsilyl triflate, bis (trimethylsilyl) sulfate, chlorotrimethylsilane, chlorotriethylsilane, trimethylmethoxysilane, Multifunctional silanol derivatives: dimethyldimethoxysilane, methyltrimethoxysilane, tetramethoxysilane, trimethylethoxysilane, dimethyldiethoxysilane, methyltriethoxysilane, tetraethoxysilane, phenyltriethoxysilane, hexyltrimethoxysilane, vinyltriethoxysilane , Vinyltrimethoxysilane, 2- (3,4-epoxycyclohexyl)
  • An amino resin is a compound having a hydroxymethylamino group in which an electron withdrawing group is bonded to a nitrogen atom, and reacts with a hydroxyl group to form an ether bond.
  • the electron withdrawing group include a carbonyl group, a thiocarbonyl group, and a triazine ring.
  • a compound having an alkoxymethylamino group in which the hydroxyl group is capped with an alcohol can also be used because it generates a hydroxyl group by hydrolysis.
  • amino resins examples include the following.
  • Monofunctional amino resin N-hydroxymethylacrylamide, N-hydroxymethylmethacrylamide, N-methoxymethylacrylamide, N-methoxymethylmethacrylamide, N-butoxymethylacrylamide, N-butoxymethylmethacrylamide, N-hydroxymethylacetamide, N-hydroxymethylurea, 1- (hydroxymethyl) -5,5-dimethylhydantoin, N- (hydroxymethyl) nicotinamide, Multifunctional amino resin: N, N′-dimethylolurea, 1,3-bis (hydroxymethyl) -5- [1,3-bis (hydroxymethyl) ureido] hydantoin, 1,3,4,6-tetrakis (methoxy) Methyl) glycoluril, hexamethylolmelamine, hexamethoxymethylmelamine, hexabutoxymethylmelamine, etc., nitrogen, hydroxyl, methoxymethyl, butoxymethyl groups are substituted, urea, melamine, benzoguanamine, glycoluril, etc
  • the monofunctional amino resin in consideration of solubility, storage stability, ease of production, etc., it is preferable to use the monofunctional amino resin.
  • Examples of the compound having an epoxy group include the following.
  • Monofunctional epoxy allyl glycidyl ether, 2-ethylhexyl glycidyl ether, lauryl glycidyl ether, phenyl glycidyl ether, phenylphenol glycidyl ether, sec-butylphenol monoglycidyl ether, polyethylene glycol monophenyl ether monoglycidyl ether, N-glycidyl phthalimide, styrene oxide 1,2-epoxy-4-vinylcyclohexane, 3,4-epoxycyclohexane-1-carboxylic acid ester, 3,4-epoxycyclohexane-1-methanol, 3,4-epoxycyclohexane-1-carbaldehyde, 4, 5-epoxy-1,2-dicarboxylic acid ester, Multifunctional epoxy: sorbitol polyglycidyl ether, polyglycerin polyglycidyl ether, penta
  • (Amidation) There are various methods for amidating (a-1) a divalent or higher carboxylic acid or derivative thereof and (a-2) a primary or secondary amine having one or more hydroxyl groups at the ⁇ -position. -1)
  • the reaction can proceed by removing water when the divalent or higher carboxylic acid or derivative thereof is a carboxylic acid, and removing the acid when the carboxylic acid ester is an alcohol, carboxylic acid anhydride or halide. . In the case of water or alcohol, it is easy to remove out of the reaction system by heating.
  • a catalyst can be used during the amidation.
  • acid catalysts such as sulfuric acid, hydrochloric acid, methanesulfonic acid and p-toluenesulfonic acid
  • base catalysts such as sodium hydroxide, sodium carbonate and sodium methoxide (hereinafter collectively referred to as “base catalysts”), triethylamine, tributylamine
  • Amine catalysts such as octylamine, tetramethylethylenediamine, N, N-dimethylethanolamine, N, N-dimethylbenzylamine, pyridine, 4- (dimethylamino) pyridine, imidazole, N-methylimidazole (hereinafter referred to as “amine catalyst”) Summarize), salts and complexes containing metal ions such as iron (III), zirconium (IV), scandium (III), titanium (IV), tin (IV), hafnium (IV), diphenylammonium triflate, pentafluor
  • a solvent can be used in the amidation reaction.
  • the solvent to be used can be used as long as it is other than a solvent that reacts with a reaction substrate such as alcohol, amine, or carboxylic acid.
  • a reaction substrate such as alcohol, amine, or carboxylic acid.
  • a condensing agent activates a carboxylic acid or an amine, and the esterification reaction can be carried out under mild conditions.
  • the by-product water is combined with the condensing agent to form another compound. And a compound having a water removing action.
  • Examples of such a condensing agent include dicyclohexylcarbodiimide, diisopropylcarbodiimide, p-toluenesulfonyl chloride, 1-ethyl-3- (N, N-dimethylaminopropyl) carbodiimide hydrochloride, carbonyldiimidazole, ethyl chloroformate, chloroformate Acid isobutyl, 2,4,6-trichlorobenzoic acid chloride, 2-methyl-6-nitrobenzoic anhydride, O- (7-azabenzotriazol-1-yl) -N, N, N ′, N′— Examples thereof include tetramethyluronium hexafluorophosphate.
  • Suitable catalysts include, for example, amines such as triethylamine, tributylamine, 1,8-diazabicyclo [5.4.0] -7-undecene, and salts thereof, tetrabutyl titanate, dibutyltin dilaurate, tin octylate. And metal salts and complexes.
  • the dehydration condensation reaction proceeds by heating to 100 ° C. or higher, preferably 140 ° C. or higher without a catalyst. Alternatively, the reaction can be allowed to proceed at a lower temperature by adding an appropriate catalyst.
  • the catalysts, condensing agents, etc. described for the amidation reaction can be used for this reaction.
  • a base catalyst or an amine catalyst may be added and reacted at 0 to 100 ° C. preferable. At this time, it is preferable to use 1 mol or more of the base catalyst or amine catalyst with respect to 1 mol of carboxylic acid anhydride or carboxylic acid halide.
  • (A-4) When the compound having one or more functional groups capable of reacting with a hydroxyl group is silanol, it is preferable to add a base catalyst or an amine catalyst and react at 0 to 100 ° C. At this time, it is preferable to use 1 mol or more of the base catalyst or amine catalyst with respect to 1 mol of carboxylic acid anhydride or carboxylic acid halide.
  • a strong base catalyst such as potassium hydroxide, sodium hydroxide, sodium methoxide, sodium ethoxide, or sodium hydride
  • the reaction is preferably performed at 0 to 200 ° C. using a metal catalyst such as tetrafluoroboric acid or tin (IV) chloride.
  • a gas having a polymerization inhibiting effect may be introduced into the reaction system during the reaction, or a polymerization inhibitor may be added. Good. By introducing a gas having a polymerization inhibition effect into the reaction system or adding a polymerization inhibitor, gelation during the addition reaction can be prevented.
  • Examples of the gas having an effect of inhibiting radical polymerization include a gas containing oxygen that does not enter the explosion range of the substance in the system, for example, air.
  • radical polymerization inhibitor known ones can be used and are not particularly limited.
  • These polymerization inhibitors may be used alone or in combination of two or more.
  • the amount of the polymerization inhibitor to be used is preferably 0.005 to 5 parts by weight, more preferably 0.03 to 3 parts by weight, more preferably 0.05 to 3 parts by weight with respect to 100 parts by weight of the total solid content in the reaction system. Most preferred is 1.5 parts by weight.
  • the amount of the polymerization inhibitor is 0.005 parts by weight or more, the polymerization inhibition effect is sufficient, while when it is 1.5 parts by weight or less, the exposure sensitivity is good. Moreover, it is more preferable to use a gas having a polymerization inhibiting effect in combination with the polymerization inhibitor because the amount of the polymerization inhibitor to be used can be reduced or the polymerization inhibiting effect can be enhanced.
  • the polymer (B) having a carboxyl group has terminal and / or side chains used for the purpose of imparting alkali developability to the resin composition and thermosetting reaction with ⁇ -hydroxyalkylamide (A).
  • a polymer having a carboxyl group It may or may not contain a photopolymerizable functional group.
  • the polymer may be linear, branched or star-shaped, and may be thermoplastic or thermosetting.
  • Examples of the polymer (B) containing a carboxyl group that does not contain a photopolymerizable functional group include, for example, carboxy-terminated polyester, polyamide, polyesteramide, polyetherester, acrylic, polybutadiene, polyisoprene, and carboxyl group side chain polyurethane, Examples thereof include carboxylic acid-added cellulose, (meth) acrylate copolymer containing a carboxyl group, and a carboxylic acid anhydride adduct of a phenol resin.
  • polymer (B) containing a carboxyl group containing a photopolymerizable functional group radically polymerizable, cationically polymerizable, and anionic polymerizable photopolymerizable functional groups can be introduced. It is preferable to contain a polymerizable photopolymerizable functional group.
  • a polymerizable photopolymerizable functional group For example, you can: (B-1) A method of introducing a photopolymerizable functional group into a polymer containing a carboxyl group; (B-2) A method in which a photopolymerizable functional group is introduced into a polymer that does not contain a carboxyl group, and a carboxyl group is introduced.
  • each polymer such as an acrylic type, a urethane type, a polyester type, a polyolefin type, a polyether type, a natural rubber, a block copolymer rubber, and a silicone type. it can.
  • (B-14) A method of reacting a hydroxyl group or the like in a compound containing a photopolymerizable functional group with an acid anhydride group in a polymer containing a carboxylic anhydride group;
  • (B-15) A method of reacting an acid anhydride group and a compound containing a photopolymerizable functional group with a hydroxyl group or amino group in a polymer containing a hydroxyl group or an amino group, etc. It is done.
  • the polymer (B) containing a carboxyl group can be used alone or in combination of two or more.
  • the ratio of the carboxyl group in the polymer (B) containing a carboxyl group to the hydroxyl group in the ⁇ -hydroxylamide group is preferably 10/1 to 1/10, more preferably 3/1 to 1/3 in molar ratio. Further, 1.5 / 1 to 1 / 1.5 is preferable. When it is in the range of 10/1 to 1/10, the hydroxyl group in the carboxyl group or ⁇ -hydroxyalkylamide group does not remain in the cured film or fine pattern, and the chemical resistance and heat resistance are very excellent.
  • the concentration of the carboxyl group in the polymer (B) containing a carboxyl group is preferably an acid value of 10 to 250 mgKOH / g, more preferably 20 to 200 mgKOH / g, and further preferably 40 to 100 mgKOH / g.
  • the functional group (carboxyl group) capable of reacting with the hydroxyl group in ⁇ -hydroxyalkylamide (A) is sufficient, and the chemical resistance and heat resistance are excellent.
  • the viscosity of a coating agent is moderate and the storage stability is excellent.
  • an active methylene group such as phenolic hydroxyl group, aromatic mercapto group, ⁇ -diketone, etc. can be used in addition to the carboxyl group.
  • the functional group can be introduced into the polymer (B) containing a carboxyl group. It may be contained in ⁇ -hydroxyalkylamide (A) or photopolymerizable monomer (D).
  • the visible light region has a wavelength of 400 to 700 nm.
  • a polymer having a transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region is used. From the viewpoint of transparency, a (meth) acrylic copolymer containing a carboxyl group is preferably used.
  • the polymer (B) containing a carboxyl group is required to satisfy photosensitivity to active energy rays and developability to dilute aqueous alkali solution. It is preferable to use a polymer containing a carboxyl group containing a photopolymerizable functional group. More preferably, a polymer having a double bond equivalent of 200 to 5000 g / eq and an acid value of 10 to 200 mgKOH / g is preferably used. Specifically, (meth) acrylic copolymers can be used, but urethane resins, addition-type ester resins, phenoxy resins, and the like can also be used.
  • the polymer (B) containing a carboxyl group is 100 parts by weight in total of the solid content of the interlayer insulating film coating agent for the touch panel from the viewpoint of adhesion, hardness, and transmittance. Among them, it is preferably used in an amount of 10 to 60 parts by weight.
  • the ⁇ -hydroxyalkylamide (A) and the polymer (B) containing a carboxyl group are 1 to 400 parts by weight, preferably 1 to 400 parts by weight with respect to 100 parts by weight of the pigment. It can be used in an amount of 250 parts by weight.
  • the carboxyl group-containing polymer (B) is 100 parts by weight to 1000 parts by weight with respect to 100 parts by weight of ⁇ -hydroxyalkylamide (A) in the photosensitive solder resist ink. It is preferably added at a rate of 100 parts by weight to 500 parts by weight.
  • ((Meth) acrylic copolymer containing carboxyl group) As a method of obtaining a (meth) acrylic copolymer containing a carboxyl group, a method of copolymerizing (meth) acrylic acid or a (meth) acrylate containing a carboxyl group with another monomer, or a hydroxyl group (meta ) A method of reacting a hydroxyl group in a polymer obtained by copolymerizing an acrylate with another monomer with an acid anhydride group in a polybasic acid anhydride.
  • Examples of the (meth) acrylate containing a carboxyl group include acrylic acid dimer, 2- (meth) acryloyloxyethyl phthalate, 2- (meth) acryloyloxypropyl phthalate, 2- (meth) acryloyloxyethylhexa Examples thereof include hydrophthalate, 2- (meth) acryloyloxypropyl hexahydrophthalate, ethylene oxide-modified succinic acid (meth) acrylate, ⁇ -carboxyethyl (meth) acrylate, and ⁇ -carboxypolycaprolactone (meth) acrylate.
  • Itaconic acid maleic acid, fumaric acid, crotonic acid, ⁇ - (hydroxymethyl) acrylic acid, ⁇ - (hydroxymethyl) methacrylic acid, p-vinylbenzoic acid and the like can also be used.
  • (Meth) acrylic acid is preferred from the viewpoints of copolymerizability and availability.
  • Examples of the (meth) acrylate containing an epoxy group include glycidyl (meth) acrylate, methyl glycidyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate glycidiether, 3,4-epoxybutyl (meth) acrylate, 3-methyl-3,4-epoxybutyl (meth) acrylate, 3-ethyl-3,4-epoxybutyl (meth) acrylate, 4-methyl-4,5-epoxypentyl (meth) acrylate, 5-methyl-5 , 6-epoxyhexyl (meth) acrylate, glycidyl ⁇ -ethyl acrylate, allyl glycidyl ether, crotonyl glycidyl ale, (iso) crotonic acid glycidyl ether, (3,4-epoxycyclohexyl) methyl (meth) acrylate, Further, aromatic
  • ⁇ -methyl-o-vinylbenzylglycidyl ether ⁇ -methyl-m-vinylbenzylglycidyl ether, ⁇ -methyl-p-vinylbenzylglycidyl ether, 2,3-diglycidyloxymethylstyrene, 2,4-diglycidyl Oxymethylstyrene, 2,5-diglycidyloxymethylstyrene, 2,6-diglycidyloxymethylstyrene, 2,3,4-triglycidyloxymethylstyrene, 2,3,5-triglycidyloxymethylstyrene, 2, 3,6-trig Glycidyloxy-methylstyrene, 3,4,5-glycidyloxy-methylstyrene, etc.
  • Glycidyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate glycidyl ether are preferable from the viewpoint of easy availability of industrial products, and the concentration of ethylenically unsaturated groups can be increased and formed from a photosensitive composition. Glycidyl (meth) acrylate is more preferable in that UV curing in the coating film is easy to proceed.
  • Examples of the (meth) acrylate containing a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 1 , 4-cyclohexanedimethanol mono (meth) acrylate, 2-acryloyloxyethyl-2-hydroxyethyl (meth) phthalate, diethylene glycol mono (meth) acrylate, dipropylene glycol mono (meth) acrylate, polyethylene glycol mono (meth) Acrylate, propylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, polytetramethylene glycol mono (meth) acrylate, poly (ethylene glycol) -Propylene glycol) mono (meth) acrylate, poly (ethylene glycol-tetramethylene glycol) mono (meth) acrylate, poly
  • 2-Hydroxyethyl (meth) acrylate is preferred from the viewpoint of copolymerization and availability.
  • polybasic acid anhydride examples include maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, chlorendic anhydride, trimellitic anhydride And polybasic acid anhydrides. From the viewpoint of solvent solubility, tetrahydrophthalic anhydride and hexahydrophthalic anhydride are preferred.
  • Examples of (meth) acrylates containing isocyanate groups include (meth) acryloyl isocyanate, 1,1-bis ((meth) acryloylmethyl) ethyl isocyanate, m- (meth) acryloylphenyl isocyanate, and 2- (meth) acryloyl. Examples thereof include oxyethyl isocyanate, 2- (meth) acryloyloxyethyl isocyanate, and 2- (meth) acryloyloxyethoxyethyl isocyanate.
  • 2-Methacryloyloxyethyl isocyanate is preferred because the concentration of the ethylenically unsaturated group can be increased, ultraviolet curing in the coating film formed from the photosensitive composition is easy to proceed, and it is easily available.
  • Examples of unsaturated acid anhydrides include maleic anhydride and itaconic anhydride.
  • (meth) acrylic copolymer containing a carboxyl group other monomers such as copolymerizable (meth) acrylate can be copolymerized, and known ones can be used without limitation. .
  • a compound represented by the following formula (11) When a (meth) acrylate containing a compound represented by the formula (11) is copolymerized to obtain a resin, a cyclization reaction of the compound represented by the formula (11) proceeds simultaneously with the polymerization, thereby producing a tetrahydropyran ring. A structure is formed.
  • R 22 and R 23 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
  • the hydrocarbon group having 1 to 25 carbon atoms which may have a substituent is not particularly limited.
  • methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, t -Linear or branched alkyl groups such as amyl, stearyl, lauryl, 2-ethylhexyl; aryl groups such as phenyl; cyclohexyl, t-butylcyclohexyl, dicyclopentadienyl, tricyclodecanyl, isobornyl, adamantyl, And alicyclic groups such as 2-methyl-2-adamantyl; alkyl groups substituted with alkoxy such as 1-methoxyethyl and 1-ethoxyethyl; alkyl groups substituted with aryl groups such as benzyl; and the like.
  • R 22 and R 23 may be the same or different.
  • Specific examples of the compound represented by the formula (11) include, for example, dimethyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate, diethyl-2,2 ′-[oxybis (methylene)] bis.
  • dimethyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate, diethyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate, dicyclohexyl -2,2 '-[oxybis (methylene)] bis-2-propenoate and dibenzyl-2,2'-[oxybis (methylene)] bis-2-propenoate are preferred, and only one kind may be used. There may be more than species.
  • the ratio at the time of polymerizing the compound represented by the formula (11) is not particularly limited, but it is 2 to 60 parts by weight, preferably 5 to 55 parts by weight, based on 100 parts by weight of all monomer components used for the polymerization.
  • the amount is preferably 5 to 50 parts by weight.
  • the amount of the compound represented by the formula (11) is 60 parts by weight or less, a low molecular weight product is obtained during the copolymerization, and no gelation occurs.
  • the amount is 2 parts by weight or more, Good film performance such as transparency and heat resistance.
  • the weight average molecular weight (Mw) of the polymer (B) containing a carboxyl group is preferably 2000 to 25000, and more preferably 4000 to 15000.
  • the weight average molecular weight (Mw) is 2000 or more, the heat resistance is excellent, and when it is 25000 or less, the coating property is excellent.
  • Examples of a method for obtaining a urethane resin containing a carboxyl group include a method of reacting a compound having two hydroxyl groups in the molecule, a carboxylic acid compound having two hydroxyl groups in the molecule, and a diisocyanate compound. is there.
  • a method for obtaining a urethane resin containing a photopolymerizable functional group and a carboxyl group there are the methods (B-1) and (B-2) described above.
  • (B-19) a method of reacting a part of the carboxyl group in the carboxyl group-containing urethane resin with the epoxy group in the (meth) acrylate containing an epoxy group
  • (B-20) After reacting a part of the carboxyl groups in the carboxyl group-containing urethane resin with the epoxy groups in the (meth) acrylate containing an epoxy group, A method of reacting with a basic acid anhydride, Etc.
  • the compound having two hydroxyl groups in the molecule is not particularly limited as long as it is a compound having two hydroxyl groups in the molecule, but has a repeating unit having a polymerization degree of 2 or more in its structure (polyol compound). And those that do not have (diol compounds).
  • polyol compound examples include polyethylene oxide, polypropylene oxide, block copolymer or random copolymer of ethylene oxide / propylene oxide, polytetramethylene glycol, block copolymer or random copolymer of tetramethylene glycol and neopentyl glycol
  • Polyether polyols such as A polyester polyol which is a condensate of a polyhydric alcohol or polyether polyol and a polybasic acid such as maleic anhydride, maleic acid, fumaric acid, itaconic anhydride, itaconic acid, adipic acid, isophthalic acid; A polycarbonate polyol obtained by a reaction of glycol or bisphenol with a carbonic acid ester or a reaction of phosgene with glycol or bisphenol in the presence of alkali; Examples include caprolactone-modified polyol such as caprolactone-modified polytetramethylene polyol, polyolefin-based polyol
  • polyether polyols are preferred from the viewpoints of developability with dilute alkaline aqueous solution and flexibility of the cured coating film.
  • diol compound examples include ethylene glycol, propylene glycol, 2-methyl-1,3-propanediol, 2-methyl-2-ethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, 2-butyl-2-methyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 3-methyl-1 , 5-pentanediol, 2,4-diethyl-1,5-pentanediol, 2-methyl-2,4-pentanediol, 1,3,5-trimethyl-1,3-pentanediol, 2-methyl-1 , 8-octanediol, 3,3′-dimethylolheptane, propanediol, 1,3-butanediol, 1,4-butanedi
  • phosphorus atom-containing diols examples include phosphorus atom-containing diols, sulfur atom-containing diols, bromine atom-containing diols, and fluorine atom-containing diols.
  • the carboxylic acid compound having two hydroxyl groups in the molecule is not particularly limited as long as it is a compound having two hydroxyl groups and one or more carboxyl groups in the molecule.
  • dimethylol butanoic acid, dimethylol Propionic acid and derivatives thereof caprolactone adduct, ethylene oxide adduct, propylene oxide adduct, etc.
  • 3-hydroxysalicylic acid 4-hydroxysalicylic acid, 5-hydroxysalicylic acid, 2-carboxy-1,4-cyclohexanedimethanol Etc.
  • dimethylolbutanoic acid and dimethylolpropionic acid are preferred in the present invention in that the concentration of carboxyl groups in the resin can be increased.
  • diisocyanate compound examples include aromatic diisocyanate, aliphatic diisocyanate, araliphatic diisocyanate, and alicyclic diisocyanate.
  • addition type ester resin containing carboxyl group As a method for obtaining an addition type ester resin containing a carboxyl group, for example, a compound having two carboxyl groups in a molecule and a compound having two epoxy groups in the molecule are reacted to contain a side chain hydroxyl group. There is a method of synthesizing an addition type ester resin and then modifying the hydroxyl group to a carboxyl group with a polybasic acid anhydride.
  • an addition type ester resin containing a photopolymerizable functional group and a carboxyl group there are the methods (B-1) and (B-2) described above, and more specifically: (B-21) a method of reacting a part of the carboxyl group in the carboxyl group-containing addition-type ester resin with the epoxy group in the (meth) acrylate containing an epoxy group, (B-22) A part or all of the carboxyl groups in the carboxyl group-containing addition-type ester resin are reacted with the epoxy groups in the (meth) acrylate containing an epoxy group, and then formed in the hydroxyl group-containing urethane resin.
  • the compound having two carboxyl groups in the molecule is not particularly limited as long as it is a compound having two carboxyl groups in the molecule, and the compounds listed above for (a-1) divalent or higher carboxylic acids, etc. Is mentioned.
  • the compound having two epoxy groups in the molecule is not particularly limited as long as it is a compound having two epoxy groups in the molecule.
  • 1,6-hexanediol diglycidyl ether is preferable from the viewpoint of flexibility of the cured coating film
  • bisphenol A / epichlorohydrin type epoxy resin is preferable from the viewpoint of heat resistance of the cured coating film.
  • Phenoxy resin containing carboxyl group As a method for obtaining a phenoxy resin containing a carboxyl group, for example, a compound having two phenolic hydroxyl groups in the molecule and a compound having two epoxy groups in the molecule are reacted to form a side chain hydroxyl group-containing phenoxy. There is a method of modifying a hydroxyl group to a carboxyl group with a polybasic acid anhydride after synthesizing the resin.
  • an addition type ester resin containing a photopolymerizable functional group and a carboxyl group there are the methods (B-1) and (B-2) described above, and more specifically: (B-23) a method of reacting a part of the carboxyl group in the carboxyl group-containing phenoxy resin with the epoxy group in the (meth) acrylate containing an epoxy group, (B-24) After reacting a part or all of the carboxyl groups in the carboxyl group-containing phenoxy resin with the epoxy groups in the (meth) acrylate containing an epoxy group, A method of reacting with a polybasic acid anhydride, Etc.
  • the compound having two phenolic hydroxyl groups in the molecule is not particularly limited as long as it is a compound having two phenolic hydroxyl groups in the molecule.
  • 2,2-bis (4-hydroxyphenyl) propane also known as bisphenol A
  • bisphenol A is a representative example.
  • Bisphenols in which a hydrogen atom is bonded to a central carbon such as bis (4-hydroxyphenol) methane (also known as bisphenol F); Bisphenols in which one methyl group is bonded to the central carbon such as 2,2-bis (4-hydroxyphenyl) -n-butane; Bisphenols in which two methyl groups are bonded to a central carbon such as 2,2-bis (3-methyl-4-hydroxyphenyl) propane (commonly called bisphenol C); Bisphenols which are diphenylmethane derivatives such as bis (4-hydroxyphenyl) -1,1-diphenylmethane; Bisphenols which are cyclohexane derivatives such as 1,1-bis (4-hydroxyphenyl) cyclohexane (commonly called bisphenol Z); Bisphenols which are -3,3,5-trimethylcyclohexane derivatives such as 1,1-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane; Bisphenols which are fluorene derivative
  • dihydroxybenzenes such as hydroquinone, resorcinol, catechol, methylhydroquinone;
  • dihydroxynaphthalene such as 1,5-dihydroxynaphthalene and 2,6-dihydroxynaphthalene.
  • 2,2-bis (4-hydroxyphenyl) propane is preferred from the viewpoints of production cost, ease of reaction, and heat resistance of the cured coating film.
  • the resin composition may contain a resin that does not contain a carboxyl group.
  • the thermoplastic resin include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, and polyester resin. , Acrylic resins, alkyd resins, polystyrene, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene, polybutadiene, polyimide resins, and the like.
  • thermosetting resin examples include epoxy resin, benzoguanamine resin, rosin-modified maleic acid resin, rosin-modified fumaric acid resin, melamine resin, urea resin, phenol resin and the like.
  • epoxy resin publicly known ones can be used, and the following compounds having an epoxy group, compounds having an alicyclic epoxy group described as cationically polymerizable among the photopolymerizable monomers (D), fats Group epoxy resins, compounds having an oxetanyl group, (a-4) compounds described as compounds having an epoxy group among compounds having at least one functional group capable of reacting with a hydroxyl group, and the like can be used.
  • examples of products that are preferably used when used as a photosensitive composition for a color filter include the following.
  • Epicoat 807, Epicoat 815, Epicoat 825, Epicoat 827, Epicoat 828, Epicoat 190P, Epicoat 191P (the above are trade names; manufactured by Yuka Shell Epoxy Co., Ltd.), Epicoat 1004, Epicoat 1256, JER 1032H60, JER 157S65, JER 157S70 , JER152, JER154 (the above are trade names; manufactured by Japan Epoxy Resin Co., Ltd.), TECHMORE VG3101L (trade names; manufactured by Mitsui Chemicals, Inc.), EPPN-501H, 502H, EPPN-501H, EPPN-201, EOCN-102S , EOCN-103S, EOCN-104S, EOCN-1020, XD-1000, NC-3000, (trade name; manufactured by Nippon Kayaku Co., Ltd.), Celoxide 2021, EHPE-3 50, EHPE-3150CE (trade name; manufactured by Daicel Chemical Industries, Ltd.), Denacol EX-9
  • the resin composition when it is a photosensitive composition for a color filter, it is a polymer having a transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region.
  • a thermoplastic resin containing no carboxyl group and a thermosetting resin may be used in combination.
  • an epoxy resin is preferably used in combination as a thermosetting resin.
  • the content can be within a range that does not impair the effects of the present invention.
  • the total amount of the ⁇ -hydroxyalkylamide (A), the polymer (B) containing a carboxyl group, the thermoplastic resin containing no carboxyl group and the thermosetting resin is 100 parts by weight of the pigment in the photosensitive composition for color filters. On the other hand, it is preferably 1 to 400 parts by weight, more preferably 1 to 250 parts by weight.
  • thermoplastic resin and a thermosetting resin that do not contain a carboxyl group can be used in combination as required, as long as the physical properties are not impaired.
  • epoxy resin or blocked isocyanate is preferably used as the thermosetting resin in order to satisfy the required properties such as flexibility, insulation, adhesion, solder heat resistance, coating film resistance, and flame resistance of the cured coating film.
  • a group-containing compound is used in combination.
  • the above epoxy resin can be used as appropriate.
  • an isocyanurate ring-containing epoxy compound such as trishydroxyethyl isocyanurate triglycidyl ether or triglycidyl isocyanurate.
  • polyfunctional epoxy compounds such as a phenol novolak-type epoxy resin, a cresol novolak-type epoxy resin, and a biphenol epichlorohydrin type epoxy resin.
  • the blocked isocyanate group-containing compound is not particularly limited as long as the isocyanate group in the isocyanate group-containing compound is a blocked isocyanate group-containing compound protected with ⁇ -caprolactam, MEK oxime, cyclohexanone oxime, pyrazole, phenol, or the like. Is not to be done.
  • hexamethylene diisocyanate trimer having an isocyanurate ring and blocked with MEK oxime or pyrazole may be used. preferable.
  • thermosetting resin containing no carboxyl group is 1 part by weight to 100 parts by weight of the polymer (B) containing ⁇ -hydroxyalkylamide (A) and carboxyl group in the photosensitive solder resist ink. It is preferably added in a proportion of 50 parts by weight, more preferably in a proportion of 5 to 30 parts by weight.
  • Organic solvent is not particularly limited, but methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol, tert-butanol, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, methyl acetate, ethyl acetate, propyl acetate,
  • Examples include butyl acetate, benzene, toluene, ethylbenzene, xylene, cyclohexane, hexane, octane, cyclomethane, chloroform, dimethylformamide, dimethylacetamide, acetonitrile, dimethyl sulfoxide, and the like. These can be used alone or in combination of two or more.
  • ketone-based, ester-based, or ether-based solvent because the solubility of other constituent elements is good.
  • a high boiling point solvent of 160 ° C. or higher
  • a high boiling point solvent for example, 3-methoxy-3-methyl-1-butanol (bp 174 ° C.), 1,3-butanediol (bp 203 ° C.), 3-methyl-1,3-butanediol (bp 203 ° C.), 2-methyl-1, 3-propanediol (bp 213 ° C.), diisobutyl ketone (bp 168.1 ° C.), ethylene glycol monobutyl ether (bp 171.2 ° C.), ethylene glycol monohexyl ether (bp 208.1 ° C.), ethylene glycol monobutyl ether acetate (bp 191.5) ° C), ethylene glycol dibutyl ether (bp 203.3 ° C.), diethylene glycol
  • the compound represented by the formula (1) is soluble in an organic solvent, for example, a solubility of 5 weight at 25 ° C. in at least one organic solvent among isopropanol, methyl ethyl ketone, ethyl acetate, and toluene. % Or more.
  • the amount of the organic solvent used is preferably such that the solid concentration of the resin composition is 5 to 50% by weight.
  • the solid content concentration of the resin composition is 5 to 50% by weight.
  • the resin composition is a coating agent for touch panel interlayer insulation or a photosensitive composition for color filters, it can be easily applied on a transparent substrate such as a glass substrate so that the dry film thickness is 0.2 to 10 ⁇ m.
  • An organic solvent is used for the purpose.
  • the preferable content of the organic solvent in the resin composition varies depending on the use of the resin composition.
  • a coating agent for a touch panel interlayer insulating film 200 to 4000 parts by weight with respect to a total solid content of 100 parts by weight. It is preferable to use it in the quantity.
  • the photosensitive composition for a color filter When used, it is preferably used in an amount of 100 to 10,000 parts by weight, preferably 500 to 5000 parts by weight with respect to 100 parts by weight of the pigment.
  • the solvent does not evaporate during handling until the application to the substrate, such as the storage process and the coating process, is completed.
  • the diluting solvent at the time of preparing the ink those having the above high boiling point are preferable. Of these, carbitol acetate, methoxypropyl acetate, cyclohexanone, diisobutyl ketone and the like are particularly preferable.
  • liquid resist inks there are also two-component types that are stored in advance separately from the curing agent in consideration of storage stability and handling, and mixed with a curing agent as necessary before coating. is there. In the case of the present invention, it can also be used as a two-component type, for example, by storing separately from the others as necessary.
  • the solvent to be used is preferably a low boiling point solvent because it is necessary to dry the solvent completely in a short time.
  • the organic solvent is preferably used in an amount of 100 to 1000 parts by weight based on 100 parts by weight of the total solid content in the photosensitive solder resist ink.
  • One embodiment of the resin composition may contain a photopolymerization initiator (C).
  • the photopolymerization initiator (C) is a compound that initiates polymerization of a photopolymerizable functional group by generating radicals, cations, and anions upon irradiation with light.
  • Thioxanthone compounds 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxy) Phenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (trichloro) Methyl) -s-triazine, 2,4-bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2 -(4-Methoxy-naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl
  • Oxime ester compounds such as N-phenylcarbazole skeleton oxime ester having a group, phosphine compounds such as bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide 2,2′-bis (o-chlorophenyl) -4,5,4 ′, 5′-tetraphenyl-1,2′-biimidazole, 2,2′-bis (o-methoxyphenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl) -4,4', 5,5'-tetra (p Examples include imidazole compounds such as -methylphenyl) biimidazole, quinone compounds such as 9,10-phenanthrenequinone, camphorquinone, and ethylanthraquinon
  • Examples include onium salt compounds.
  • onium salt compounds include sulfonium salt compounds, iodonium salt compounds, phosphonium salt compounds, diazonium salt compounds, pyridinium salt compounds, benzothiazolium salt compounds, sulfoxonium salt compounds, and ferrocene compounds. These structures are not particularly limited, and may have a polyvalent cation structure such as a dication, and known counter anions can be appropriately selected and used.
  • Acid generators other than onium salts include nitrobenzyl sulfonates, alkyl or aryl-N-sulfonyloxyimides, optionally halogenated alkyl sulfonate esters, 1,2-disulfones, oxime sulfonates Compounds having a trihaloalkyl group such as benzoin tosylates, ⁇ -ketosulfones, ⁇ -sulfonylsulfones, bis (alkylsulfonyl) diazomethanes, iminosulfonates, imidosulfonates, trihalomethyltriazines, etc. It can be mentioned, but is not limited to these.
  • Specific examples include tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium hydrogen sulfate, tetraethylammonium tetrafluoroborate, tetraethylammonium, p-toluenesulfonate, N, N-dimethyl-N-benzylanilinium.
  • Antimony hexafluoride N, N-dimethyl-N-benzylanilinium tetrafluoride, N, N-dimethyl-N-benzylpyridinium antimony hexafluoride, N, N-diethyl-N-benzyltrifluoromethanesulfonic acid, N, N-dimethyl-N- (4-methoxybenzyl) pyridinium antimony hexafluoride, N, N-diethyl-N- (4-methoxybenzyl) toluidinium hexafluoride antimony Ethyltriphenylphosphonium hexafluoride antimony, tetrabutylphosphonium hexafluoride antimony, triphenylsulfonium boron tetrafluoride, triphenylsulfonium hexafluoroantimony, triphenylsulfonium hexafluoroarsenide, tri
  • Examples of the photopolymerization initiator (C) that generate anions include o-nitrobenzoin carbamate, benzoin carbamate, ⁇ , ⁇ -dimethylbenzyloxycarbamoylamine, o-acyloxime, formanilide derivatives, ⁇ -ammonium acetophenone. Etc.
  • photopolymerization initiators (C) those generating radicals, cations and anions can be used alone or in combination. Moreover, it can be used 1 type or in mixture of 2 or more types by arbitrary ratios as needed.
  • the photopolymerization initiator (C) is preferably from 0.01 to 60 parts by weight, more preferably from 0.01 to 10 parts by weight, and still more preferably from 0.03 to 100 parts by weight in 100 parts by weight of the solid content in the resin composition. 7 parts by weight. When it is 0.01 parts by weight or more, the photocuring reactivity is good, and when it is 60 parts by weight or less, the initiator is not yellowed and the transparency is good.
  • the resin composition when used as, for example, a coating agent for a touch panel interlayer insulating film, since it is necessary to satisfy both hardness and adhesion, a radical polymerizable photopolymerization initiator and a cationic polymerizable photopolymerization initiator are required. It is preferable to use together.
  • radical polymerizable initiators examples are given above, but when used as a coating agent for touch panel interlayer insulation films, acetophenone photopolymerization initiators and oxime ester photopolymerization initiators have high sensitivity, Since the addition amount may be small, the transmittance increases, so that it is preferably used.
  • the photopolymerization initiator (C) is preferably used in an amount of 1 to 30 parts by weight in a total of 100 parts by weight of the solid content of the resin composition. From the viewpoint of transmittance, it is more preferably used in an amount of 1 to 10 parts by weight.
  • the photopolymerization initiator (C) is preferably used in an amount of 1 to 200 parts by weight, more preferably 1 to 150 parts by weight, based on 100 parts by weight of the pigment in the photosensitive composition for color filters.
  • the photopolymerization initiator (C) is preferably added in the range of 1 to 20 parts by weight with respect to 100 parts by weight of the solid content in the photosensitive solder resist ink.
  • the resin composition may contain a sensitizer.
  • Sensitizers include unsaturated ketones represented by chalcone derivatives and dibenzalacetone, 1,2-diketone derivatives represented by benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives and other polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azurenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylpor
  • Specific examples include Okawara Nobu et al., “Dye Handbook” (1986, Kodansha), Okawara Nobu et al., “Functional Dye Chemistry” (1981, CMC), Ikemori Chusaburo et al., “Special Examples include, but are not limited to, sensitizers described in “Functional Materials” (1986, CMC).
  • a sensitizer that absorbs light from the ultraviolet region to the near infrared region can also be contained.
  • the sensitizer may contain two or more sensitizers in any ratio.
  • the sensitizer is preferably used in an amount of 0.1 to 150 parts by weight, preferably 1 to 100 parts by weight, with respect to 100 parts by weight of the photopolymerization initiator (C) in the photosensitive composition. Is more preferable.
  • the amount of the sensitizer used is 0.1 to 150 parts by weight with respect to 100 parts by weight of the photopolymerization initiator (C). It is preferable to use in.
  • a known organic amine can be added as a sensitizer. Further, it is preferably used in an amount of 0.1 to 150 parts by weight with respect to 100 parts by weight of the photopolymerization initiator (C).
  • One embodiment of the resin composition may contain a photopolymerizable monomer (D).
  • the photopolymerizable monomer (D) is a compound containing a photopolymerizable functional group, and the structure thereof may or may not have a carboxyl group.
  • those that do not have a carboxyl group and undergo radical polymerization include, for example, Methyl (meth) acrylate, ethyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, ⁇ -carboxyethyl (meth) acrylate , Tricyclodecanyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, trimethylol Propane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol
  • those that do not have a carboxyl group and undergo cationic polymerization include, for example, Examples of the compound having an epoxy group include bisphenol A type epoxy resin, glycidyl ether type epoxy resin, phenol novolac type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, cresol novolac type epoxy resin, glycidyl amine type epoxy resin, Alcohols such as naphthalene type epoxy resin, aliphatic epoxy resin, alicyclic epoxy resin, heterocyclic epoxy resin, polyfunctional epoxy resin, biphenyl type epoxy resin, glycidyl ester type epoxy resin, hydrogenated bisphenol A type epoxy resin Epoxy resin, halogenated epoxy resin such as brominated epoxy resin, rubber modified epoxy resin, urethane modified epoxy resin, epoxidized polybutadiene, epoxidized styrene-butadiene-styrene Examples include block copolymers, epoxy group-containing polyester resin
  • epoxy resins may be liquid or solid at room temperature
  • epoxy group-containing oligomers can also be suitably used, for example, bisphenol A type epoxy oligomers (for example, oil (Epicoat 1001, 1002, etc., manufactured by Kasei Shell Epoxy Co., Ltd.)
  • addition polymers of the above epoxy group-containing monomers and oligomers may be used, for example, glycidylated polyester, glycidylated polyurethane, glycidylated acrylic. Etc.
  • Examples of the compound having an alicyclic epoxy group include 1,2: 8,9-diepoxy limonene, 4-vinylcyclohexene monoepoxide, vinylcyclohexene dioxide, methylated vinylcyclohexene dioxide, (3,4-epoxy).
  • aliphatic epoxy resin examples include, for example, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, ethylene glycol diglycidyl ether, ethylene glycol monoglycidyl ether, propylene glycol diglycidyl ether, propylene Glycol monoglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, neopentyl glycol monoglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, trimethylolpropane diglycidyl Ether, trimethylolpropane monoglycidyl ether, trimethylolpropane trig Ether, diglycerol triglycidyl ether, sorbito
  • Examples of the compound having an oxetanyl group include phenoxymethyl oxetane, 3,3-bis (methoxymethyl) oxetane, 3,3-bis (phenoxymethyl) oxetane, 3-ethyl-3- (phenoxymethyl) oxetane, 3- Ethyl-3- (2-ethylhexyloxymethyl) oxetane, 3-ethyl-3- ⁇ [3- (triethoxysilyl) propoxy] methyl ⁇ oxetane, di [1-ethyl (3-oxetanyl)] methyl ether, oxetanyl And silsesquioxane, phenol novolac oxetane, 1,4-bis ⁇ [(3-ethyl-3-oxetanyl) methoxy] methyl ⁇ benzene, and the like.
  • Examples of the compound having a vinyl ether group include hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, and the like.
  • Other examples include compounds having an episulfide group, an ethyleneimine group, and a hydroxyl group.
  • Examples of the photopolymerizable monomer (D) that does not have a carboxyl group and undergoes anionic polymerization include compounds having the above epoxy group.
  • photopolymerizable monomers (D) can be used alone or in admixture of two or more.
  • a radical polymerizable photopolymerizable monomer and a cationic polymerizable photopolymerization are used. It is preferable to use an ionic monomer in combination.
  • the photopolymerizable monomer (D) is usually photocured by irradiating with ultraviolet rays or an electron beam [adding a photopolymerization initiator (C) if necessary]. If necessary, a thermal polymerization initiator may be added] to cause thermosetting.
  • radically polymerizable photopolymerizable monomers examples include a monomer containing 7 or more radically polymerizable photopolymerizable functional groups in one molecule. Further, from the viewpoint of maintaining transmittance and balancing pencil hardness and adhesion, it is preferable to include a photopolymerizable monomer containing 7 to 14, preferably 8 to 10 photopolymerizable functional groups.
  • a monomer having 7 or more polymerizable unsaturated bonds for example, from the group consisting of tripentaerythritol hepta (meth) acrylate, tripentaerythritol octa (meth) acrylate, and a compound represented by the following formula (12) It is preferable that it is at least one selected.
  • R 24 represents a divalent organic group excluding an oxygen atom
  • R 25 represents a hydrogen atom or a methyl group.
  • divalent organic group examples include alkylene groups such as methylene group, ethylene group and propylene group, arylene groups such as phenylene group, tolylene group and xylylene group, ether group, carbonyl group, sulfonyl group and ester group.
  • alkylene groups such as methylene group, ethylene group and propylene group
  • arylene groups such as phenylene group, tolylene group and xylylene group
  • ether group carbonyl group, sulfonyl group and ester group.
  • the structure represented by the following formula (13) is preferable.
  • R 26 represents an aliphatic, alicyclic or aromatic structure.
  • Examples of the compound represented by the formula (12) include compounds obtained by reacting dipentaerythritol penta (meth) acrylate and polyfunctional isocyanate, dipentaerythritol penta (meth) acrylate and tetrabasic acid dianhydride.
  • the compound obtained by making it react, the compound obtained by making dipentaerythritol penta (meth) acrylate and a polyfunctional epoxy compound react can be mentioned.
  • polyfunctional isocyanates include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, and isophorone diisocyanate.
  • tetrabasic acid dianhydrides include pyromellitic anhydride, biphenyltetracarboxylic dianhydride, naphthalenetetracarboxylic dianhydride, diphenyl ether tetracarboxylic dianhydride, butanetetracarboxylic dianhydride.
  • Cyclopentanetetracarboxylic dianhydride, oxydiphthalic anhydride, ethylene glycol bisanhydro trimellitate, glycerin bis (anhydro trimellitate monoacetate), benzophenone tetracarboxylic dianhydride, methylcyclohexylene tetracarboxylic acid A dianhydride etc. can be mentioned.
  • polyfunctional epoxy compound examples include tris (glycidylphenyl) methane, triglycidyl isocyanurate, bis (3,4-epoxycyclohexylmethyl) adipate, bis (3,4-epoxy-6-methylcyclohexylmethyl) Examples thereof include adipate, methylene bis (3,4-epoxycyclohexane), bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, and novolak type epoxy resin.
  • tripentaerythritol hepta (meth) acrylate or tripentaerythritol octa (meth) acrylate is preferable as the photopolymerizable monomer (D), and these are mixed. It may be included.
  • a photopolymerizable monomer (D) commercially available products include, for example, Biscoat # 802 (mixture of tripentaerythritol octaacrylate and tripentaerythritol heptaacrylate, manufactured by Osaka Organic Chemical Industry Co., Ltd.). it can.
  • the photopolymerizable monomer (D) may include a polyfunctional monomer having an acidic group.
  • a polyfunctional monomer having an acidic group For example, free hydroxyl group-containing poly (meth) acrylates of polyhydric alcohol and (meth) acrylic acid, and dicarboxylic acids
  • An esterified product of a polycarboxylic acid and a monohydroxyalkyl (meth) acrylate can be used.
  • monomethyl oligoacrylates or monohydroxy oligomethacrylates such as trimethylolpropane diacrylate, trimethylolpropane dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol pentamethacrylate.
  • Monoesterified products containing free carboxyl groups with dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, terephthalic acid; propane-1,2,3-tricarboxylic acid (tricarballylic acid), butane-1,2,4 -Tricarboxylic acids such as tricarboxylic acid, benzene-1,2,3-tricarboxylic acid, benzene-1,3,4-tricarboxylic acid, benzene-1,3,5-tricarboxylic acid And a free carboxyl group-containing oligoester product of monohydroxy monoacrylate or monohydroxy monomethacrylate such as 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, etc. be able to.
  • dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, terephthalic acid; propane-1,2,3-tricarboxylic
  • the content of the photopolymerizable monomer (D) is 100 parts by weight in total of the solid content of the coating agent for the touch panel interlayer insulating film,
  • the amount is preferably 5 to 80 parts by weight, more preferably 10 to 50 parts by weight. If it is 5 parts by weight or more, hardness and chemical resistance are sufficient, and if it is 80 parts by weight or less, transmittance and adhesion are excellent.
  • the photopolymerizable monomer (D) is preferably 10 to 300 parts by weight, more preferably 10 to 200 parts by weight, based on 100 parts by weight of the pigment in the color filter photosensitive composition.
  • the ratio [Ia / M] of the weight [Ia] of the photopolymerization initiator (C) to the weight [M] of the photopolymerizable monomer (D) is 0.03 to It is preferably 1.00, and more preferably 0.04 to 0.95.
  • the photosensitive composition for color filters contains a sensitizer
  • the total weight [Ib] of the photopolymerization initiator (C) and the sensitizer and the weight of the photopolymerizable monomer (D) [ The ratio [Ib / M] to M] is preferably 0.04 to 1.50, more preferably 0.05 to 1.45.
  • the amount is preferably 10 to 1000 parts by weight, more preferably 50 to 800 parts by weight, based on 100 parts by weight of the total of ⁇ -hydroxyalkylamide (A) and the polymer (B) containing a carboxyl group.
  • One embodiment of the resin composition may contain a pigment.
  • required for example, when using as a photosensitive composition for color filters, a resin composition can contain a pigment.
  • organic or inorganic pigments can be used alone or in admixture of two or more.
  • pigments having high color developability and high heat resistance are preferable, and organic pigments are usually used.
  • red photosensitive composition for forming the red filter segment examples include CI Pigment Red 7, 9, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, and 81: 2, 81: 3, 97, 122, 123, 146, 149, 168, 177, 178, 179, 180, 184, 185, 187, 192, 200, 202, 208, 210, 215, 216, 217, 220, Red pigments such as 223, 224, 226, 227, 228, 240, 242, 246, 254, 255, 264, 272, and 279 can be used.
  • a yellow pigment and an orange pigment can be used in combination with the red photosensitive composition.
  • yellow pigments can be used in a yellow photosensitive composition for forming a yellow filter segment, alone or in combination of two or more.
  • orange pigments such as C.I. Pigment orange 36, 43, 51, 55, 59, 61, 71, 73 can be used.
  • orange pigments can be used in an orange photosensitive composition for forming an orange filter segment alone or in combination of two or more.
  • Green pigments such as C.I. Pigment Green 7, 10, 36, 37 and 58 can be used for the green photosensitive composition for forming the green filter segment.
  • the yellow pigment described above can be used in combination with the green photosensitive composition.
  • Blue photosensitive compositions for forming blue filter segments include, for example, CI Pigment Blue 15, 15, 1: 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, Blue pigments such as 80 can be used. Purple pigments such as C.I.CPigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, and 50 can be used in combination with the blue photosensitive composition.
  • blue pigments such as CI Pigment Blue 15: 1, 15: 2, 15: 4, 15: 3, 15: 6, 16, and 80 are used. be able to.
  • magenta color photosensitive composition for forming the magenta color filter segment for example, purple pigments and red pigments such as C.I. Pigment Violet 1, 19, C.I. Pigment Red 81, 144, 146, 177, and 169 can be used.
  • a yellow pigment can be used in combination with the magenta photosensitive composition.
  • black photosensitive composition for forming the black matrix examples include carbon black, aniline black, anthraquinone black pigment, perylene black pigment, specifically, CI CI pigment black 1, 6, 7, 12, 20, 31. Etc. can be used.
  • CI CI pigment black 1, 6, 7, 12, 20, 31. Etc. CI CI pigment black 1, 6, 7, 12, 20, 31. Etc.
  • a mixture of a red pigment, a blue pigment, and a green pigment can also be used.
  • carbon black is preferable from the viewpoint of price and light shielding properties, and the carbon black may be surface-treated with a resin or the like.
  • a blue pigment and a purple pigment can be used together in a black photosensitive composition.
  • inorganic pigments include barium sulfate, zinc white, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, ultramarine, bitumen, chromium oxide green, cobalt green, amber, titanium black.
  • examples thereof include metal oxide powders such as synthetic iron black, titanium oxide, and iron tetroxide, metal sulfide powders, and metal powders.
  • Inorganic pigments are used in combination with organic pigments in order to ensure good coatability, sensitivity, developability and the like while maintaining a balance between saturation and lightness.
  • a dye in the photosensitive composition for color filter, can be contained within a range that does not reduce heat resistance for color matching.
  • the content of the pigment in the resin composition is not particularly limited.
  • a preferable concentration of the pigment component is sufficient based on the total nonvolatile components (100% by weight). From the viewpoint of obtaining color reproducibility, it is 10% by weight or more, more preferably 15% by weight or more, and most preferably 20% by weight or more. Further, since the stability of the photosensitive composition for color filters is improved, the concentration of the preferred pigment component is 90% by weight or less, more preferably 80% by weight or less, and most preferably 70% by weight or less. .
  • a phthalocyanine pigment represented by the following formula may be added as a pigment.
  • this embodiment is a photosensitive composition for a color filter comprising ⁇ -hydroxyalkylamide (A), a polymer (B) containing a carboxyl group, and a phthalocyanine pigment represented by the following formula (17). There may be.
  • the color does not change even when irradiated with light in the absence of oxygen as in a color filter.
  • ⁇ -hydroxyalkylamide (A) does not inactivate radicals generated during photocuring, and therefore does not adversely affect pattern formation. Therefore, a high quality color filter can be obtained by using such a colored composition.
  • X 1 to X 4 are each independently an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, or a substituent.
  • Y 1 to Y 4 each independently represent a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group, or an optionally substituted sulfamoyl group.
  • M represents Zn or Al-Z.
  • Z represents —OP ( ⁇ O) R 27 R 28 , wherein R 27 and R 28 each independently represent a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, or a substituent. Represents a good aryl group, an alkoxyl group which may have a substituent, or an aryloxy group which may have a substituent, and R 5 and R 6 may be bonded to each other to form a ring.
  • q 1 , q 2 , q 3 , q 4 , r 1 , r 2 , r 3 , and r 4 each independently represent an integer of 0 to 4, q 1 + r 1 , q 2 + r 2 , q 3 + R 3 and q 4 + r 4 are each 0 to 4, and may be the same or different.
  • alkyl group of the alkyl group which may have a substituent, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group,
  • alkyl group which may have a substituent, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group.
  • Examples include a linear or branched alkyl group such as an n-octyl group, a stearyl group, and a 2-ethylhexyl group.
  • alkyl group having a substituent examples include a trichloromethyl group, a trifluoromethyl group, 2, 2, 2-trifluoroethyl group, 2,2-dibromoethyl group, 2,2,3,3-tetrafluoropropyl group, 2-ethoxyethyl group, 2-butoxyethyl group, 2-nitropropyl group, benzyl group, 4 -Methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, 2,4-dichlorobenzyl group, etc. .
  • aryl group of the aryl group which may have a substituent examples include a phenyl group, a naphthyl group, and an anthryl group, and the “aryl group having a substituent” includes a p-methylphenyl group, p- Bromophenyl group, p-nitrophenyl group, p-methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-aminophenyl group, 2-methyl-4-chlorophenyl group, 4-hydroxy-1-naphthyl Group, 6-methyl-2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinonyl group, 2-aminoanthraquinonyl group and the like.
  • Examples of the “cycloalkyl group” of the cycloalkyl group which may have a substituent include a cyclopentyl group, a cyclohexyl group, an adamantyl group and the like, and examples of the “cycloalkyl group having a substituent” include 2,5 -Dimethylcyclopentyl group, 4-tert-butylcyclohexyl group and the like.
  • Examples of "" include 3-methylpyridyl group, N-methylpiperidyl group, N-methylpyrrolyl group and the like.
  • alkoxyl group of the alkoxyl group which may have a substituent, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a neopentyloxy group, 2 , 3-dimethyl-3-pentyloxy, n-hexyloxy group, n-octyloxy group, stearyloxy group, 2-ethylhexyloxy group and the like linear and branched alkoxyl groups such as “alkoxyl having a substituent”
  • the group include trichloromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 2,2,3,3-tetrafluoropropoxy group, 2,2-ditrifluoromethylpropoxy group, 2- Ethoxyethoxy group, 2-butoxyethoxy group, 2-nitropropoxy group, benz
  • Examples of the “aryloxy group” of the aryloxy group which may have a substituent include a phenoxy group, a naphthoxy group, and an anthryloxy group, and the “aryloxy group having a substituent” includes p-methyl Examples include phenoxy group, p-nitrophenoxy group, p-methoxyphenoxy group, 2,4-dichlorophenoxy group, pentafluorophenoxy group, 2-methyl-4-chlorophenoxy group.
  • alkylthio group examples include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, an octylthio group, a decylthio group, a dodecylthio group, and an octadecylthio group.
  • alkylthio group having a substituent examples include a methoxyethylthio group, an aminoethylthio group, a benzylaminoethylthio group, a methylcarbonylaminoethylthio group, a phenylcarbonylaminoethylthio group, and the like.
  • Preferred examples of the phthalocyanine pigment include C.I. I. Pigment Green 58 green pigment.
  • C.I. I. Pigment Green 58 green pigment In order to improve light resistance, it is particularly preferable to use a pigment exhibiting green, and in order to exhibit green, it is preferable that 1 to 16 halogen atoms are contained in one pigment molecule. In order to obtain better color developability, it is desirable that there are 4 to 16 halogen atoms in one pigment molecule.
  • the aluminum phthalocyanine pigment is not particularly limited as long as it has a structure in which trivalent aluminum is coordinated at the center of the phthalocyanine ring.
  • aluminum is known to have a structure such as a dimer and a trimer in addition to a monomer, because it is trivalent and has a bond in addition to a bond with phthalocyanine.
  • the phthalocyanine ring can be chemically modified and can take various structures.
  • the aluminum phthalocyanine pigment in the present embodiment may take any form such as not only a monomer but also a structure such as a dimer or a trimer, or a chemically modified phthalocyanine ring.
  • the aluminum phthalocyanine pigment those represented by the following formula (18) are preferable in terms of color characteristics and dispersibility.
  • X 1 to X 4 are each independently an alkyl group that may have a substituent, an aryl group that may have a substituent, or a cycloalkyl group that may have a substituent.
  • a heterocyclic group which may have a substituent, an alkoxyl group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent Represents an arylthio group which may have
  • Y 1 to Y 4 each independently represent a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group, or an optionally substituted sulfamoyl group.
  • Z represents a hydroxyl group, a chlorine atom, —OP ( ⁇ O) R 27 R 28 , or —O—SiR 29 R 30 R 31 .
  • R 27 to R 31 are each independently a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, or an alkoxyl group which may have a substituent. Or an aryloxy group which may have a substituent, and R 27 to R 31 may be bonded to each other to form a ring.
  • q 1 to q 4 and r 1 to r 4 each independently represent an integer of 0 to 4, and q 1 + r 1 , q 2 + r 2 , q 3 + r 3 , and q 4 + r 4 are each 0 to 4 may be the same or different.
  • X 1 to X 4 may be the same or different. Specific examples thereof include an alkyl group which may have a substituent, an aryl group which may have a substituent, and a substituent.
  • Examples thereof may include an alkylthio group which may be substituted and an arylthio group which may have a substituent.
  • the substituents may be the same or different.
  • halogen groups such as fluorine, chlorine and bromine, amino groups, hydroxyl groups and nitro groups.
  • an alkyl group, an aryl group, a cycloalkyl group, an alkoxyl group, an aryloxy group, an alkylthio group, an arylthio group, and the like can be given.
  • arylthio group examples include a phenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, a 9-anthrylthio group, and the like, and “an arylthio group having a substituent” Chlorophenylthio group, trifluoromethylphenylthio group, cyanophenylthio group, nitrophenylthio group, 2-aminophenylthio group, 2-hydroxyphenylthio group and the like.
  • One embodiment of the resin composition may contain a dye. It is also preferable to use an organic pigment in combination.
  • a color filter having high heat resistance, chemical resistance, smoothness, and optical characteristics is provided by including a polymer containing ⁇ -hydroxyalkylamide (A) and a carboxyl group. I can do it.
  • ⁇ -hydroxyalkylamide (A) does not inactivate radicals and therefore does not adversely affect pattern formation. Therefore, a high quality color filter can be obtained by using such a colored composition.
  • the dyes are, among others, triphenylmethane dyes, triphenylmethane lake pigments, diphenylmethane dyes, diphenylmethane lake pigments, quinoline dyes, quinoline pigments Thiazine dyes, thiazole dyes, xanthene dyes, xanthene lake pigments, diketopyrrolopyrrole pigments, and the like can be used.
  • xanthene dyes xanthene dyes that are xanthene lake pigments
  • quinoline dyes quinoline dyes that are quinoline pigments
  • triphenylmethane dyes triphenylmethane dyes that are triphenylmethane lake pigments
  • diketopyrrolopyrrole pigment that is a diketopyrrolopyrrole pigment.
  • the color filter having a high contrast ratio is excellent.
  • the dye that can be preferably used when it is in the form of a dye, it has any form of various dyes such as an oil-soluble dye, an acid dye, a direct dye, a basic dye, a mordant dye, and an acid mordant dye. Preferably there is.
  • examples of the pigment form include fluorescent pigments and lake pigments obtained by rake-forming the dyes.
  • the colorant is a dye
  • Oil-soluble dyes are classified as color indexes, C.I.
  • Examples of basic dyes classified as I. Solvent are the same as C.I.
  • Examples of the acid dyes that are classified into I. Basic are the same as those of C.I.
  • Examples of the dyes classified as I. Acid and direct dyes include C.I. I. It is classified as direct.
  • the direct dye has a sulfonic acid group (—SO 3 H, —SO 3 Na) in the structure, and in this embodiment, the direct dye is regarded as an acid dye.
  • Xanthene (Xanthene dyes: Xanthene dyes, lake pigments)
  • the transmittance is 90% or more in the region of 650 nm in the transmission spectrum, the transmittance is 75% or more in the region of 600 nm, the transmittance is 5% or less in the region of 500 to 550 nm, and the region of 400 nm. And a transmittance of 70% or more is preferable.
  • the transmittance is 95% or more in the region of 650 nm, the transmittance is 80% or more in the region of 600 nm, the transmittance is 10% or less in the region of 500 to 550 nm, and the transmittance is 75% in the region of 400 nm. That's it.
  • xanthene-based basic dyes and xanthene-based acid dyes have spectral characteristics having a high transmittance at 400 to 450 nm.
  • rhodamine-based dyes are excellent in color developability and resistance. This is preferable.
  • xanthene oil-soluble dyes include CI Solvent Red 35, CI Solvent Red 36, CI Solvent Red 42, CI Solvent Red 43, and CI Solvent. Red 44, CI Solvent Red 45, CI Solvent Red 46, CI Solvent Red 47, CI Solvent Red 48, CI Solvent Red 49, CI Solvent Red 72 CI Solvent Red 73, CI Solvent Red 109, CI Solvent Red 140, CI Solvent Red 141, CI Solvent Red 237, CI Solvent Red 246, C CI Solvent Violet 2, CI Solvent Violet 10 and the like.
  • CI solvent red 35, CI solvent red 36, CI solvent red 49, CI solvent red 109, CI solvent red, which are rhodamine-based oil-soluble dyes having high color development Red 237, CI Solvent Red 246, and CI Solvent Violet 2 are more preferable.
  • xanthene dyes examples include C.I. I. Acid Red 51 (erythrosin (edible red No. 3)), C.I. I. Acid Red 52 (Acid Rhodamine), C.I. I. Acid Red 87 (Eosin G (edible red No. 103)), C.I. I. Acid Red 92 (Acid Phloxin PB (edible red No. 104)), C.I. I. Acid Red 289, C.I. I. Acid Red 388, Rose Bengal B (edible red No. 5), Acid Rhodamine G, C.I. I. It is preferable to use Acid Violet 9.
  • C.I. is a xanthene acid dye in terms of heat resistance and light resistance.
  • I. Acid Red 87, C.I. I. Acid Red 92, C.I. I. Acid Red 388 or rhodamine acid dye C.I. I. Acid Red 52 (Acid Rhodamine), C.I. I. Acid Red 289, Acid Rhodamine G, C.I. I. It is more preferable to use Acid Violet 9.
  • C.I. which is a rhodamine acid dye
  • C.I. which is a rhodamine acid dye
  • xanthene basic dyes examples include C.I. I. Basic Red 1 (Rhodamine 6 GCP), 8 (Rhodamine G), C.I. I. Basic violet 10 (rhodamine B) and the like. Among these, C.I. I. Basic Red 1, C.I. I. Basic violet 10 is preferably used.
  • Xanthene dye metal lake pigments include CI Pigment Red 81, CI Pigment Red 81: 1, CI Pigment Red 81: 2, C.I. Pigment Red 81: 3, and C.I. CI Pigment Red 81: 4, CI Pigment Red 81: 5, CI Pigment Red 169, CI Pigment Violet 1, CI Pigment Violet 1: 1, CI Pigment Violet 1: 2, CI Pigment Violet 2 and the like.
  • a blue (blue) triarylmethane basic dye has spectral characteristics having a high transmittance at 400 to 440 nm.
  • Triphenylmethane basic dyes and diphenylmethane basic dyes are colored by the formation of a quinone structure by oxidation of the NH 2 or OH group located in the para position relative to the central carbon.
  • a triaminotriphenylmethane-based basic dye is preferable in terms of good blue, red and green coloring. .
  • Diaminotriphenylmethane-based basic dye b) Triaminotriphenylmethane-based basic dye c) Rosolic acid-based basic dye having an OH group Triaminotriphenylmethane-based basic dye, Diaminotriphenylmethane-based basic dye
  • the dye has a clear color tone and is preferable because it is more excellent in sunfastness than other dyes. Diphenylnaphthylmethane basic dye and / or triphenylmethane basic dye are preferred.
  • triarylmethane lake pigments include C.I. I. Pigment Blue 1, C.I. I. Pigment Blue 2, C.I. I. Pigment Blue 9, C.I. I. Pigment Blue 10, C.I. I. Pigment Blue 14, C.I. Pigment Blue 62, CI Pigment Violet 3, CI Pigment Violet 27, CI Pigment Violet 39, and the like.
  • quinoline dyes examples include dyes commercially available with color indexes such as Solvent Yellow 33, Solvent Yellow 98, Solvent Yellow 157, Disperse Yellow 54, Disperse Yellow 160, and Acid Yellow 3.
  • quinoline pigments examples include C.I. I. Pigment Yellow 138 (Pariotor Yellow K0961-HD manufactured by BSF).
  • thiazine dye As thiazine dyes, Lauth's Violet obtained by oxidizing P-phenylenediamine in the presence of hydrogen sulfide under FeCl 2, methylene blue, methylene green B, C.I. basic blue 9, 17, 24, 25 Solvent Blue 8, CI Basic Green 5, CI Direct Red 70 and the like.
  • thiazole dye As the thiazole dye, a dye having a thiazole ring is a thiazole dye. Specifically, CI basic yellow 1, CI basic violet 44, 46, CI basic blue 116, CI Acid Yellow 186, Direct Yellow 7, 8, 9, 14, 17, 18, 22, 28, 29, 30, 54, 59, 165, CI Direct Orange 18, CI Direct Red 11, etc. are mentioned.
  • the salt-forming compound (Z) salted with an organic acid or perchloric acid.
  • organic acid organic sulfonic acid or organic carboxylic acid is preferably used.
  • naphthalenesulfonic acid such as tobias acid and perchloric acid are preferably used in terms of resistance.
  • a quaternary ammonium salt compound In the case of acidic dyes and direct dyes, a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, a primary amine compound, and the like, and a salt formed using a resin component having these functional groups It is preferable in terms of resistance to use as the salt compound (Z), or as the salt-forming compound (Z) obtained by sulfonamidation into a sulfonic acid amide compound.
  • a salt forming compound (Z) which is a salt forming compound of an acidic dye and / or a sulfonic acid amide compound of an acidic dye is preferable because of its excellent resistance and combined use with a pigment. It is more preferable to use a salt-forming compound (Z) that is salted using a quaternary ammonium salt compound that is a counter component that works as a counter ion.
  • the acidic dye is formed by using a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, a primary amine compound, etc., and a resin component having these functional groups (hereinafter referred to as a salt-forming resin C1) to produce an acid salt. It is preferable to use a salt-forming compound of a dye or a sulfonamidation to form a salt-forming compound of a sulfonic acid amide compound because high heat resistance, light resistance, and solvent resistance can be imparted.
  • Primary amine compounds include methylamine, ethylamine, propylamine, isopropylamine, butylamine, amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine (laurylamine), tridodecylamine, tetra Examples include aliphatic unsaturated primary amines such as decylamine (myristylamine), pentadecylamine, cetylamine, stearylamine, oleylamine, cocoalkylamine, beef tallow alkylamine, cured tallow alkylamine, allylamine, aniline, and benzylamine. .
  • Secondary amine compounds include aliphatic unsaturated secondary amines such as dimethylamine, diethylamine, dipropylamine, diisopropylamine, dibutylamine, diamylamine, diallylamine, methylaniline, ethylaniline, dibenzylamine, diphenylamine, dicocoalkyl.
  • Examples of tertiary amine compounds include trimethylamine, triethylamine, tripropylamine, tributylamine, triamylamine, dimethylaniline, diethylaniline, and tribenzylamine. .
  • an acid dye which is chlorinated using a quaternary ammonium salt, or an acid dye is sulfonamidated, and these two forms will be described in detail below.
  • the dye is most preferably used as a salt-forming compound (Z) comprising the above-mentioned acidic dye and a quaternary ammonium salt compound from the viewpoints of heat resistance, light resistance and solvent resistance.
  • Quaternary ammonium salt compound A quaternary ammonium salt compound has an amino group, and its cation part becomes a counter of a xanthene acid dye.
  • colorless or white means a so-called transparent state, and is defined as a state in which the transmittance is 95% or more, preferably 98% or more in the entire wavelength region of 400 to 700 nm in the visible light region. Is. That is, it is necessary not to inhibit color development of the dye component and to cause no color change.
  • the molecular weight of the salt-forming resin (C1) of the cation moiety serving as a counter for the quaternary ammonium salt compound is preferably in the range of 190 to 900.
  • the cation moiety corresponds to the (NR 101 R 102 R 103 R 104 ) + moiety in the following formula (19).
  • the molecular weight is smaller than 190, light resistance and heat resistance are lowered, and the solubility in a solvent may be further lowered.
  • the molecular weight is larger than 900, the ratio of the coloring component in the molecule is lowered, so that the color developability is lowered and the lightness may be lowered.
  • the molecular weight of the cation moiety is more preferably in the range of 240 to 850, and particularly preferably in the range of 350 to 800.
  • the molecular weight was calculated based on the structural formula.
  • the atomic weight of C was 12, the atomic weight of H was 1, and the atomic weight of N was 14.
  • the compound represented by following formula (19) can be used as a quaternary ammonium salt compound.
  • R 101 to R 104 each independently represents an alkyl group having 1 to 20 carbon atoms or a benzyl group, and at least two of R 101 , R 102 , R 103 , or R 104 are , C is 5-20.
  • Y represents an inorganic or organic anion.
  • the Y-component constituting the anion of the quaternary ammonium salt compound may be an inorganic or organic anion, but is preferably a halogen, usually chlorine.
  • quaternary ammonium salt compounds include tetramethylammonium chloride (with a molecular weight of the cation moiety of 74), tetraethylammonium chloride (with a molecular weight of the cation moiety of 122), and monostearyltrimethylammonium chloride (with a molecular weight of the cation moiety).
  • distearyldimethylammonium chloride (cation part molecular weight 550), tristearyl monomethylammonium chloride (cation part molecular weight 788), cetyltrimethylammonium chloride (cation part molecular weight 284), trioctylmethylammonium chloride ( The molecular weight of the cation moiety is 368), dioctyldimethylammonium chloride (the molecular weight of the cation moiety is 270), monolauryltrimethyl Ammonium chloride (cation part molecular weight 228), dilauryldimethylammonium chloride (cation part molecular weight 382), trilaurylmethylammonium chloride (cation part molecular weight 536), triamylbenzylammonium chloride (cation part molecular weight 318), trihexylbenzylammonium chloride (cation part molecular weight 360), trioctylbenzylammonium chloride (cation part
  • Products include Kao's Coatamine 24P, Cotamin 86P Conch, Cotamin 60W, Cotamin 86W, Cotamin D86P, Sanizole C, Sanizole B-50, etc., Lion Corporation's Arcade 210-80E, 2C-75, 2HT-75, 2HT flakes, 2O-75I, 2HP-75, 2HP flakes, etc. are mentioned, among others, Cotamine D86P (distearyldimethylammonium chloride), or Arcard 2HT-75 (dialkyl (alkyl is C14 to C18) dimethylammonium chloride), etc. It is preferable.
  • the quaternary ammonium salt compound may be in the form of a resin having a cationic group, particularly an amino group or an ammonium group in the side chain, and capable of forming a quaternary ammonium salt structure by reacting and salting with a xanthene acid dye. .
  • the salt-forming compound of an acidic dye and a quaternary ammonium salt compound can be manufactured by a conventionally known method.
  • a specific technique is disclosed in Japanese Patent Laid-Open No. 11-72969.
  • the quaternary ammonium salt compound is added, and the chlorination treatment may be performed while stirring.
  • a salt-forming compound in which the sulfonic acid group (—SO 3 H), sodium sulfonate group (—SO 3 Na) portion in the acid dye and the ammonium group (NH 4 +) portion of the quaternary ammonium salt compound are combined. Is obtained.
  • methanol and ethanol are also solvents that can be used during chlorination.
  • the molecular weight of the dye (C) in the form of an acid dye (C.I. Acid Red 289, C. I. Acid Red 52, etc.) and the cation moiety serving as a counter is 350 to 800.
  • the solvent solubility is excellent, and when used in combination with a pigment described later, the heat resistance, light resistance, and solvent resistance are more excellent.
  • the salt formation compound (Z) that is favorable when used in combination with the pigment is due to adsorption to the pigment while being dissolved and dispersed in the solvent.
  • the primary particle diameter of the pigment is preferably 20 to 100 nm.
  • the colored composition is preferably in the form of a blue colored composition used in combination with a blue pigment, a red colored composition used in combination with a red pigment, a yellow colored composition used in combination with a yellow pigment, or a green colored composition.
  • [Sulphonic acid amide compound of acid dye] An acidic dye sulfonic acid amide compound that can be preferably used as a dye is obtained by chlorinating an acidic dye having —SO 3 H and —SO 3 Na by a conventional method to convert —SO 3 H into —SO 2 Cl. Can be prepared by reacting with an amine having a —NH 2 group.
  • C.I. I In the case of obtaining a sulfonic acid amide compound obtained by modifying Acid Red 289 with 3- (2-ethylhexyloxy) propylamine, C.I. I. Acid Red 289 was converted to a sulfonyl chloride and reacted with the theoretical equivalent of 3- (2-ethylhexyloxy) propylamine in dioxane to give C.I. I. What is necessary is just to obtain the sulfonic acid amide compound of Acid Red 289.
  • C.I. I In the case of obtaining a sulfonic acid amide compound obtained by modifying Acid Red 52 with 3- (2-ethylhexyloxy) propylamine, C.I. I. Acid Red 52 was converted to a sulfonyl chloride and reacted with the theoretical equivalent of 3- (2-ethylhexyloxy) propylamine in dioxane to give C.I. I. What is necessary is just to obtain the sulfonic acid amide compound of Acid Red 52.
  • Salt-forming compound composed of basic dye and compound of organic acid and inorganic acid Basic dyes are insufficient in light resistance and heat resistance, and their characteristics are not sufficient for use in image display devices using color filters that require high reliability. Therefore, in order to improve the defects in these dyes, it is preferable to salt the basic dye using an organic acid or an inorganic acid.
  • the organic acid it is preferable to use an organic sulfonic acid or an organic carboxylic acid, and it is particularly preferable to use naphthalenesulfonic acid. Tobias acid is particularly preferable.
  • As the inorganic acid it is particularly preferable to use perchloric acid.
  • a dispersion aid such as a resin-type pigment dispersant, a surfactant, or a pigment derivative can be appropriately contained. Since the dispersion aid is excellent in pigment dispersion and has a great effect of preventing re-aggregation of the pigment after dispersion, a resin composition obtained by dispersing the pigment in a resin and / or solvent using the dispersion aid is used. If it is, a cured product having excellent transparency can be obtained.
  • the dispersion aid is preferably 0.1 to 40 parts by weight, and more preferably 0.1 to 30 parts by weight with respect to 100 parts by weight of the pigment.
  • the resin-type dispersant has a pigment-affinity part having the property of adsorbing to the pigment and a part compatible with the dye carrier, and functions to adsorb to the pigment and stabilize the dispersion of the pigment on the dye carrier.
  • resin-type pigment dispersants include polyurethanes, polycarboxylic acid esters such as polyacrylates, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamines.
  • Salts polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl group-containing polycarboxylic acid esters, their modified products, amides formed by the reaction of poly (lower alkylene imines) with polyesters having free carboxyl groups, and the like
  • Oil-based dispersants such as salts, water-soluble such as (meth) acrylic acid-styrene copolymers, (meth) acrylic acid- (meth) acrylic ester copolymers, styrene-maleic acid copolymers, polyvinyl alcohol, polyvinylpyrrolidone Resin, water-soluble polymer, polyester Modified polyacrylate, ethylene oxide / propylene oxide addition compound, phosphate ester-based and the like are used, they can be used alone or in admixture of two or more.
  • resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, and 170 manufactured by Big Chemie Japan.
  • Surfactants include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkylnaphthalenesulfonate, sodium alkyldiphenyletherdisulfonate, lauryl sulfate monoethanolamine, lauryl Anionic surfactants such as triethanolamine sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate; polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxy Ethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, polyethylene glycol Nonionic surfactants such as nolaurate; chaotic surfactants such as alkyl quaternary ammonium salts and their ethylene
  • the pigment derivative is a compound in which a substituent is introduced into an organic pigment, and the organic pigment also includes light yellow aromatic polycyclic compounds such as naphthalene-based and anthraquinone-based compounds that are not generally called pigments.
  • the pigment derivatives are described in JP-A-63-305173, JP-B-57-15620, JP-B-59-40172, JP-B-63-17102, JP-B-5-9469, and the like. These can be used alone or in combination of two or more.
  • One embodiment of the resin composition may contain a flame retardant.
  • a flame retardant when the resin composition is used for applications requiring flame retardancy, for example, when a photosensitive solder resist ink is used, it is preferable to contain a flame retardant.
  • Examples of the flame retardant include melamine phosphate, melamine polyphosphate, guanidine phosphate, guanidine polyphosphate, ammonium phosphate, ammonium polyphosphate, ammonium amidophosphate, ammonium polyphosphate, carbamate phosphate, and carbamate polyphosphate.
  • Phosphate compounds and polyphosphate compounds red phosphorus, organophosphate compounds, phosphazene compounds, phosphonic acid compounds, aluminum diethylphosphinate, aluminum methylethylphosphinate, aluminum diphenylphosphinate, aluminum ethylbutylphosphinate, Phosphinic acid compounds such as aluminum methylbutylphosphinate and aluminum aluminum phosphinate, phosphine oxide compounds, phosphorane compounds, phosphoramidation Phosphorus-based flame retardants such things; Nitrogen flame retardants such as melamine, melam, melem, melon, melamine cyanurate and other triazine compounds, cyanuric acid compounds, isocyanuric acid compounds, triazole compounds, tetrazole compounds, diazo compounds, urea; Silicon-based flame retardants such as silicone compounds and silane compounds; Halogen flame retardants such as halogenated bisphenol A, halogenated epoxy compounds, halogen
  • non-halogen flame retardants such as phosphorus flame retardants and nitrogen flame retardants, and in particular, phosphazenes that are more effective for flame retardancy in resin compositions. It is preferable to use a compound, a phosphinic acid compound, melamine polyphosphate, ammonium polyphosphate, melamine cyanurate, or the like. These flame retardants can be used alone or in combination.
  • the content of the flame retardant is not particularly limited, for example, when the resin composition is a photosensitive solder resist ink, it is 5 to 200 parts by weight with respect to 100 parts by weight of the polymer (B) containing a carboxyl group. It is preferably 20 to 150 parts by weight.
  • the resin composition further includes a thermoplastic resin, a thermosetting resin, a curing agent used in combination, a leveling agent, an ultraviolet absorber, a light stabilizer, an antioxidant, an inorganic filler, an adhesion-imparting agent, and storage stability, if necessary.
  • Additives such as adhesion improvers such as agents, dyes, and silane coupling agents may be added. These additives can be added in any amount as long as the purpose of the resin composition is not impaired.
  • Adhesion improver When using a resin composition for the use for which the adhesiveness with a base material is calculated
  • Adhesion improvers include vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxy Propylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3-a Nopropyltri
  • a silane-based additive is preferable because adhesion to a glass substrate or ITO is improved, and 3-methacryloxypropyltrimethoxysilane is more preferable, 3-glycidoxypropyltrimethoxysilane, 3-mercapto. Propyltrimethoxysilane is particularly preferred.
  • the resin composition when used as a coating agent for a touch panel interlayer insulating film, since adhesion with a glass substrate, ITO or the like is necessary, it is preferable to contain an adhesion improver such as a silane coupling agent.
  • the adhesion improver is preferably used in an amount of 0.1 to 10 parts by weight in a total of 100 parts by weight of the solid content of the photosensitive composition. From the standpoint of adhesion, the effect of improving adhesion is good when it is 0.1 parts by weight or more, and the properties such as hardness of the resin composition are good when it is 10 parts by weight or less.
  • the photosensitive composition for a color filter it is preferable to contain an adhesion improver such as a silane coupling agent in order to improve the adhesion to the transparent substrate.
  • the silane coupling agent is preferably used in an amount of 0.01 to 10 parts by weight, more preferably 0.05 to 5 parts by weight, based on 100 parts by weight of the pigment in the photosensitive composition for color filters.
  • the resin composition When the resin composition is used for an application that requires a certain degree of hardness when cured, it preferably contains inorganic oxide fine particles.
  • the inorganic oxide fine particles are formed of at least one element selected from the group consisting of silicon, aluminum, zirconium, titanium, zinc, indium, tin, antimony, and cerium, from the viewpoint of the colorlessness of the cured film of the resulting curable composition.
  • Oxide particles are preferred. Of these, from the viewpoint of transmittance, oxide particles of silicon, zirconium, or aluminum are preferable, and silicon oxide particles are particularly preferable.
  • the inorganic oxide fine particles have an affinity with a binder component such as a polymer (B) or a photopolymerizable monomer (D) containing a carboxyl group in order to stabilize dispersion in a dispersion or coating solution.
  • a binder component such as a polymer (B) or a photopolymerizable monomer (D) containing a carboxyl group
  • physical surface treatment such as plasma discharge treatment or corona discharge treatment, and chemical surface treatment with a surfactant or a coupling agent may be performed.
  • the average primary particle diameter of the inorganic oxide particles is preferably 1 nm to 1000 nm, more preferably 3 nm to 100 nm, and particularly preferably 5 nm to 30 nm.
  • the average primary particle diameter is 1000 nm or less, the transparency when cured is good and the surface state when coated is good.
  • Various surfactants and amines may be added to improve the dispersibility of the particles.
  • the average primary particle diameter of the inorganic oxide fine particles is measured using, for example, the BET method. Specifically, the specific surface area of the inorganic oxide fine particles obtained by the BET method is obtained, the ratio of volume to surface area is calculated using the specific gravity of the inorganic oxide, and the particles are assumed to be true spheres. There is a method of obtaining the particle diameter from these ratios to obtain the average primary particle diameter.
  • the inorganic oxide particles are preferably used as an organic solvent dispersion.
  • the dispersion medium is preferably an organic solvent from the viewpoint of compatibility with other components and dispersibility.
  • organic solvent include alcohols such as methanol, ethanol, isopropanol, butanol, and octanol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ethyl acetate, butyl acetate, ethyl lactate, and ⁇ -butyrolactone.
  • Esters such as propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate; ethers such as ethylene glycol monomethyl ether and diethylene glycol monobutyl ether; aromatic hydrocarbons such as benzene, toluene and xylene; dimethylformamide, dimethylacetamide, Examples thereof include amides such as N-methylpyrrolidone.
  • methanol, isopropanol, butanol, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, toluene and xylene are preferred.
  • Examples of commercially available silicon oxide fine particle dispersions that are preferably used include MA-ST-MS, IPA-ST, IPA-ST-MS, IPA-ST-L, and IPA manufactured by Nissan Chemical Industries, Ltd. -ST-ZL, IPA-ST-UP, EG-ST, NPC-ST-30, MEK-ST, MEK-ST-L, MIBK-ST, NBA-ST, XBA-ST, DMAC-ST, ST-UP ST-OUP, ST-20, ST-40, ST-C, ST-N, ST-O, ST-50, ST-OL, etc., and hollow silica CS60-IPA manufactured by Catalyst Kasei Kogyo Co., Ltd. Can do.
  • Examples include E220A and E220 manufactured by KK, SYLYSIA470 manufactured by Fuji Silysia KK, SG flake manufactured by Nippon Sheet Glass Co., Ltd., and the like.
  • Zirconia oxide fine particle dispersions that are preferably used include ZR-40BL, ZR-30BS, ZR-30AL, ZR-30AH, etc. manufactured by Nissan Chemical Industries, Ltd., Sumitomo Osaka Cement Co., Ltd. HXU-110JC.
  • Aluminum oxide fine particle dispersions that are preferably used include Alumina Sol-100, Alumina Sol-200, Alumina Sol-520 manufactured by Nissan Chemical Industries, Ltd., AS-150I manufactured by Sumitomo Osaka Cement Co., Ltd., and AS. -150T.
  • inorganic oxide fine particle dispersions that are preferably used are shown below.
  • Antimony oxide fine particle dispersions include Celnax CX-Z330H manufactured by Nissan Chemical Industries, Ltd., and oxide fine particle dispersions of aluminum, titanium, tin, indium, zinc, etc. include Nanotech manufactured by CI Kasei Co., Ltd. be able to.
  • the resin composition is used as a coating agent for a touch panel interlayer insulating film
  • the coating agent for the touch panel interlayer insulating film the amount is preferably 10 to 40 parts by weight, more preferably 15 to 35 parts by weight, based on 100 parts by weight of the total solid content in the coating agent.
  • the addition amount is 10 parts by weight or more, the effect of improving the hardness is sufficiently obtained, while when it is 40 parts by weight or less, the adhesion is good.
  • Storage stabilizer examples include 2,6-bis (1,1-dimethylethyl) -4-methylphenol, pentaerystyryl-tetrakis [3- (3,5-di-t-butyl-4-hydroxyphenyl).
  • Propionate 2,4-bis- (n-octylthio) -6- (4-hydroxy-3,5-di-t-butylanilino) 1,3,5-triazine, hindered phenols, tetraethylphosphine, tri Organic phosphines such as phenylphosphine and tetraphenylphosphine, phosphites such as zinc dimethyldithiophosphate, zinc dipropyldithiophosphate and molybdenum dibutyldithiophosphate, sulfurs such as dodecyl sulfide and benzothiophene, benzyltrimethyl chloride, Quaternary ammonium chloride such as diethylhydroxyamine , Lactic acid, and organic acids and their methyl ethers such as oxalic acid. Used alone or in combination.
  • the viscosity with time of the composition can be stabilized.
  • the content of the storage stabilizer is preferably 0.1 to 5 parts by weight in a total of 100 parts by weight of the coating agent when the resin composition is, for example, a coating agent for a touch panel interlayer insulating film.
  • the amount is preferably 0.01 to 20 parts by weight, more preferably 0.05 to 10 parts by weight with respect to 100 parts by weight of the pigment.
  • the temporal stability of the photosensitive coloring composition is improved.
  • a photosensitive solder resist ink When a photosensitive solder resist ink is used, it is preferably used in an amount of 0.1 to 5 parts by weight in a total of 100 parts by weight of the ink.
  • Leveling agent A leveling agent may be added to highly suppress surface defects when cured.
  • dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable.
  • dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning, BYK-330 manufactured by BYK Chemie.
  • dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by BYK Chemie.
  • Dimethylsiloxane having a polyether structure in the main chain and dimethylsiloxane having a polyester structure in the main chain can be used in combination.
  • a particularly preferred leveling agent it is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, and it has a hydrophilic group but has low solubility in water and is added to a coating agent for a touch panel interlayer insulating film. In that case, it has the characteristics of low surface tension lowering ability, and even though the surface tension lowering ability is low, it is useful to have good wettability to the glass plate, resulting in the appearance of coating film defects due to foaming. Those which can sufficiently suppress the chargeability with the added amount not used can be preferably used.
  • dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used as a leveling agent having such preferable characteristics.
  • the polyalkylene oxide unit include a polyethylene oxide unit and a polypropylene oxide unit, and dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.
  • the bonding form of the polyalkylene oxide unit with dimethylpolysiloxane includes a pendant type in which the polyalkylene oxide unit is bonded in the repeating unit of dimethylpolysiloxane, a terminal-modified type in which the end of dimethylpolysiloxane is bonded, and dimethylpolysiloxane. Any of linear block copolymer types in which they are alternately and repeatedly bonded may be used.
  • Dimethylpolysiloxanes having polyalkylene oxide units are commercially available from Toray Dow Corning Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ -2207, but is not limited thereto.
  • ⁇ Anionic, cationic, nonionic or amphoteric surfactants can be supplementarily added to the leveling agent. Two or more kinds of surfactants may be mixed and used.
  • Anionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkyl naphthalene sulfonate, alkyl diphenyl ether disulfonic acid Sodium, lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate Examples include esters.
  • Nonionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate And amphoteric surfactants such as alkyl dimethylamino acetic acid betaine and alkylimidazolines, and fluorine-based and silicone-based surfactants.
  • the resin composition when used as a coating agent for a touch panel interlayer insulating film, it is preferable to add a leveling agent in order to improve the leveling property of the composition on the transparent substrate.
  • the leveling agent is preferably used in an amount of 0.003 to 0.5 parts by weight in a total of 100 parts by weight of the resin composition.
  • the antioxidant is preferably at least one selected from the group consisting of phenolic antioxidants, phosphorus antioxidants, and sulfur antioxidants.
  • an antioxidant may be included in the resin composition. preferable.
  • the resin composition may contain a polyfunctional thiol.
  • a polyfunctional thiol is a compound having two or more thiol (SH) groups.
  • a thiyl radical that acts as a chain transfer agent in the radical polymerization process after light irradiation and is not easily inhibited by polymerization by oxygen. Since it generate
  • a polyfunctional aliphatic thiol in which an SH group is bonded to an aliphatic group such as methylene or ethylene group is preferable.
  • polyfunctional thiols can be used individually by 1 type or in mixture of 2 or more types.
  • the polyfunctional thiol content is preferably 0.05 to 100 parts by weight, more preferably 1.0 to 100 parts by weight with respect to 100 parts by weight of the pigment. 50.0 parts by weight.
  • the polyfunctional thiol By using 0.05 part by weight or more of polyfunctional thiol, better development resistance can be obtained.
  • a thiol having a plurality of thiol (SH) groups By using a thiol having a plurality of thiol (SH) groups, development resistance can be improved.
  • the resin composition may contain an ultraviolet absorber or a polymerization inhibitor.
  • the resin composition is a photosensitive composition for color filters, the shape and resolution of the pattern can be controlled by containing an ultraviolet absorber or a polymerization inhibitor.
  • Examples of the ultraviolet absorber include 2- [4-[(2-hydroxy-3- (dodecyl and tridecyl) oxypropyl) oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl). -1,3,5-triazine, 2- (2-hydroxy-4- [1-octyloxycarbonylethoxy] phenyl) -4,6-bis (4-phenylphenyl) -1,3,5-triazine, etc.
  • polymerization inhibitor used alone or in combination.
  • examples of the polymerization inhibitor include methyl hydroquinone, t-butyl hydroquinone, 2,5-di-t-butyl hydroquinone, 4-benzoquinone, 4-methoxyphenol, 4-methoxy-1-naphthol, t-butylcatechol and the like.
  • Hydroquinone derivatives and phenolic compounds such as phenothiazine, bis- (1-dimethylbenzyl) phenothiazine, 3,7-dioctylphenothiazine, copper dibutyldithiocarbamate, copper diethyldithiocarbamate, manganese diethyldithiocarbamate, manganese diphenyldithiocarbamate, etc.
  • Copper and manganese salt compounds 4-nitrosophenol, N-nitrosodiphenylamine, N-nitrosocyclohexylhydroxylamine, N-nitrosophenylhydroxyl Min such nitroso compounds and their ammonium salts or aluminum salts and the like, and used alone or in combination.
  • the contents of the ultraviolet absorber and the polymerization inhibitor are not particularly limited, but when the resin composition is, for example, a color filter photosensitive composition, 0.01 to 20 parts by weight with respect to 100 parts by weight of the pigment. Is more preferable, and 0.05 to 10 parts by weight is more preferable.
  • the resin composition may contain an amine compound.
  • the resin composition is, for example, a photosensitive composition for a color filter, it is preferable to contain an amine compound having a function of reducing dissolved oxygen.
  • amine compounds examples include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminobenzoate. Examples thereof include ethyl, 2-ethylhexyl 4-dimethylaminobenzoate, N, N-dimethylparatoluidine and the like.
  • a resin composition is obtained by mixing and stirring the compound represented by Formula (1), the polymer (B) containing a carboxyl group, an organic solvent, and other components as necessary.
  • the obtained resin composition may be used as a resin composition for electronic parts.
  • touch panel interlayer insulation film, color filter, black matrix, photosensitive solder resist, color filter protective film, photo spacer, projection for liquid crystal alignment, micro lens, optical hard coat, UV ink, photosensitive lithographic printing plate, various coatings, etc. Etc. can be used to manufacture. Further, it can also be used for reinforcing plate adhesives, interlayer adhesives, coating agents, electromagnetic wave shielding adhesives, photosensitive optical waveguides, photothermal dual-curing potting agents and the like used for flexible printed wiring boards.
  • the resin composition is a photosensitive composition
  • (1) a fine pattern can be formed by the photosensitive composition having alkali developability due to the carboxyl group, and (2) a ⁇ -hydroxyalkylamide group, a carboxyl group,
  • a uniform cross-linked structure is formed by heat curing in which a photopolymerization functional group is polymerized by a photopolymerization initiator in a uniform composition, resulting in heat resistance and chemical resistance. An excellent film and pattern are formed.
  • the photosensitive composition can also be used to form a fine pattern by solvent development or to form a film or a molded product without development.
  • the carboxyl group is utilized for the crosslinking formation in (2) above.
  • the resin composition further contains a photopolymerization initiator (C). Furthermore, it is preferable to contain a photopolymerizable monomer (D) as a constituent element as necessary.
  • a photopolymerizable monomer (D) as a constituent element as necessary.
  • these constituent elements the compound represented by the formula (1), the polymer (B) containing a carboxyl group, the photopolymerizable monomer (D)
  • at least one constituent element has a photopolymerizable functional group. included.
  • the photopolymerizable monomer (D) is further an essential constituent element.
  • constituents of the photosensitive composition include the following combinations (1) to (7).
  • photopolymerization initiator or a functional group that undergoes an addition reaction when the photopolymerizable functional group itself is excited by light irradiation.
  • a photopolymerizable functional group where radical polymerization occurs acryloyl group, methacryloyl group, styryl group, maleimide group, alkenyl group, alkynyl group, etc.
  • photopolymerizable functional group where cationic polymerization occurs epoxy group, alicyclic epoxy Groups, oxetanyl groups, vinyl ether groups, episulfide groups, ethyleneimine groups, hydroxyl groups, photopolymerizable functional groups that undergo anionic polymerization, epoxy groups, and other photopolymerizable functional groups that undergo an addition reaction, ene groups, mercapto groups ( Ene-thiol addition), styryl group, maleimide group (photodimerization), vinyl group, maleimide group (photoinit
  • an acryloyl group or a methacryloyl group in the case of radical polymerization.
  • cationic polymerization it is preferable to use an epoxy group, an oxetanyl group, or a vinyl ether group, and it is more preferable to use an epoxy group or an oxetanyl group.
  • the base material examples include glass, ceramic, polycarbonate, polyester, urethane, acrylic, polyacetate cellulose, polyamide, polyimide, polystyrene, epoxy resin, polyolefin, polycycloolefin, polyvinyl alcohol, various metals such as stainless steel, and the like. It is done.
  • active energy rays include visible light, ultraviolet rays, infrared rays, X-rays, ⁇ rays, ⁇ rays, ⁇ rays and the like, and ultraviolet rays are particularly preferable.
  • a light source such as a high pressure mercury lamp, a low pressure mercury lamp, an electrodeless lamp, a xenon lamp, a metal halide lamp, or an excimer lamp.
  • Development can be performed by immersing in a solvent or an alkaline developer, or spraying the developer with a spray or the like to remove uncured portions and form a desired fine pattern.
  • the touch panel interlayer insulating film is provided to protect the ITO electrodes that are members of the touch panel and to maintain insulation between the ITO electrodes.
  • the coating agent for touch panel interlayer insulation films contains a photosensitive composition as an essential component, and can satisfy required physical properties such as chemical resistance, heat resistance, insulation, hardness, and adhesion.
  • the coating agent for the touch panel interlayer insulating film is composed of ⁇ -hydroxyalkylamide (A), a polymer containing a carboxyl group (B), a photopolymerization initiator (C), and a photopolymerizable monomer (D) as necessary. It can be obtained by stirring and mixing an organic solvent and the like, and if necessary, inorganic oxide fine particles.
  • the coating agent for the touch panel interlayer insulation film is coarse particles of 5 ⁇ m or more, preferably coarse particles of 1 ⁇ m or more, more preferably coarse particles of 0.5 ⁇ m or more and mixed by means of centrifugation, sintered filter, membrane filter, etc. It is preferable to remove dust and foreign matters.
  • the thickness at the time of manufacturing the touch panel interlayer insulating film is preferably 0.005 to 30 ⁇ m in a dry state, more preferably 0.01 to 20 ⁇ m, and particularly preferably 0.1 to 10 ⁇ m. preferable. By setting the thickness in such a range, an appropriate mechanical strength and heat resistance can be obtained, and the light transmittance is less likely to be impaired.
  • the method for applying the coating agent for the touch panel interlayer insulating film to the glass substrate, ITO, metal film, organic film, etc. is not particularly limited.
  • dipping method, spray method, roll coating method, die coating method, rotation A coating method or the like can be used, and other coating methods such as a screen printing method, an offset printing method, and a gravure printing method can also be used. It is also possible to form a pattern by photolithography.
  • the drying method after applying the coating agent for the touch panel interlayer insulating film to the glass substrate or the like is not particularly limited, but for example, an oven or an infrared heater can be used.
  • the heating conditions can also be changed depending on the type of each component used in the photosensitive composition, the addition amount (blending amount), etc., but the temperature is usually within the range of 50 to 300 ° C.
  • Heat curing is preferably performed under a condition of ⁇ 10 hours, and more preferably, a temperature of 100 to 250 ° C. is used for 0.5 to 5.0 hours.
  • the photocuring method is not particularly limited. For example, it is possible to irradiate ultraviolet rays using a high pressure mercury lamp, a metal halide lamp or the like as a light source.
  • the irradiation conditions can also be changed depending on the type of each component used in the photosensitive composition, the addition amount (blending amount), etc., but the irradiation amount of ultraviolet rays is usually 10 to 500 mJ / cm 2. More preferably, it is 20 to 300 mJ / cm 2 .
  • the carboxyl group in the polymer (B) containing a carboxyl group can be changed depending on the kind of each component used in the photosensitive composition, the addition amount (blending amount), and the like.
  • the coating agent for the touch panel interlayer insulating film may be used for any of insulating film use, protective film use, and flat film use.
  • the photosensitive composition for color filters finely disperses pigments and dyes in a pigment carrier such as a resin and / or a solvent using various dispersing means such as a three-roll mill, a two-roll mill, a sand mill, a kneader, and an attritor.
  • a pigment carrier such as a resin and / or a solvent
  • various dispersing means such as a three-roll mill, a two-roll mill, a sand mill, a kneader, and an attritor.
  • each pigment dispersion is separately mixed in a finely dispersed form in a dye carrier and / or a solvent, and ⁇ -hydroxyalkylamide (A), A polymer (B) containing a carboxyl group, a photopolymerization initiator (C), and if necessary, a photopolymerizable monomer (D), an organic solvent and the like can be mixed and stirred.
  • the polymer (B) containing a carboxyl group may be used as a dye carrier when producing a pigment dispersion.
  • the photosensitive composition for a color filter can be prepared in the form of a solvent development type or alkali development type colored resist material.
  • the colored resist material includes ⁇ -hydroxyalkylamide (A), a polymer (B) containing a carboxyl group, a photopolymerization initiator (C), and a photopolymerizable monomer (D) as necessary.
  • a pigment is dispersed in a composition containing an organic solvent.
  • the photosensitive coloring composition is obtained by means of centrifugal separation, sintering filter, membrane filter or the like, coarse particles of 5 ⁇ m or more, preferably coarse particles of 1 ⁇ m or more, more preferably coarse particles of 0.5 ⁇ m or more and mixed dust. Is preferably removed.
  • the color filter includes a filter segment or a black matrix formed from a photosensitive composition for a color filter on a transparent substrate, and a general color filter includes at least one red filter segment and at least one green filter.
  • glass plates such as soda lime glass, low alkali borosilicate glass and non-alkali aluminoborosilicate glass, and resin plates such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate are used.
  • resin plates such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate are used.
  • a transparent electrode made of indium oxide, tin oxide, or the like may be formed on the surface of the glass plate or the resin plate in order to drive the liquid crystal after forming the panel.
  • the dry film thickness of the filter segment and the black matrix is preferably 0.2 to 10 ⁇ m, more preferably 0.2 to 5 ⁇ m.
  • a vacuum dryer, a convection oven, an IR oven, a hot plate, or the like may be used.
  • the temperature is usually within the range of 50 to 300 ° C.
  • Heat curing is preferably performed under a condition of ⁇ 10 hours, and more preferably, a temperature of 100 to 250 ° C. is used for 0.5 to 5.0 hours.
  • each color filter segment and black matrix by photolithography is performed by the following method. That is, the photosensitive film composition for color filters prepared as a solvent development type or alkali development type colored resist material has a dry film thickness on a transparent substrate by a coating method such as spray coating, spin coating, slit coating or roll coating. Apply to 0.2 to 10 ⁇ m. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film.
  • a coating method such as spray coating, spin coating, slit coating or roll coating.
  • the filter segment and the black matrix can be formed by immersing in a solvent or an alkali developer, or spraying the developer with a spray or the like to remove an uncured portion to form a desired pattern. Furthermore, in order to accelerate the polymerization of the filter segment and the black matrix formed by development, heating can be performed as necessary. According to the photolithography method, it is possible to form a filter segment and a black matrix with higher accuracy than printing methods such as a screen printing method, an offset printing method, and a gravure printing method.
  • an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used.
  • an antifoamer and surfactant can also be added to a developing solution.
  • a shower development method As the development processing method, a shower development method, a spray development method, a dip (immersion) development method, a paddle (liquid accumulation) development method, or the like can be applied.
  • a water-soluble or alkali-soluble resin such as polyvinyl alcohol or water-soluble acrylic resin is applied and dried to prevent polymerization inhibition due to oxygen.
  • Ultraviolet exposure can also be performed after forming a film.
  • the photosensitive solder resist ink is unnecessary in the soldering process performed when protecting the wiring (circuit) pattern formed on the substrate from the external environment or mounting the electronic component on the printed wiring board. It is provided in order to protect the solder from adhering to the portion.
  • the resin composition can be made into a photosensitive solder resist ink, and it has photosensitivity to active energy rays, developability to dilute alkaline aqueous solution, flexibility of a cured coating film obtained through a post-curing (post-cure) process, and insulating properties. It can satisfy required properties such as adhesion, solder heat resistance, coating film resistance, and flame retardancy.
  • the photosensitive solder resist ink is finely divided by using various dispersing means such as a three roll mill, a two roll mill, a sand mill, a kneader, and an attritor in a polymer (B) solution containing a carboxyl group.
  • a dispersion is produced by dispersion, and ⁇ -hydroxyalkylamide (A), a photopolymerization initiator (C), a resin not containing a carboxyl group if necessary, a photopolymerizable monomer (D)
  • an organic solvent and in some cases, a sensitizer, a polymerization inhibitor, a storage stabilizer, and other components can be mixed and stirred.
  • the photosensitive solder resist ink removes coarse particles of 5 ⁇ m or more, preferably coarse particles of 1 ⁇ m or more, and mixed dust and foreign matters by means of centrifugation, sintered filter, membrane filter or the like.
  • the required characteristics such as high photosensitivity requested
  • the photosensitive solder resist ink having the composition as described above is used by adjusting the solution to a viscosity suitable for each coating method as required and applying it to a printed wiring board formed with a circuit.
  • Examples of the coating method include dipping, spraying, spin coater, roll coater, curtain coater, and screen printing.
  • the dry film type photosensitive solder resist can be prepared by coating the above-mentioned photosensitive solder resist ink on a separate film and then drying the solvent.
  • the coating method on the separate film is not particularly limited, and examples thereof include dipping method, spray, spin coater, roll coater, curtain coater, or screen printing, and the solution is adjusted to a viscosity suitable for the coating method. It is applied to a printed wiring board on which a circuit is formed.
  • the dry film prepared on the separate film is bonded to a copper circuit or the like formed on the polyimide, and thereafter, bubbles and the like are removed and adhered to the circuit by lamination or vacuum lamination.
  • this pasting step there may be a case where the radiation curing is performed through a separate film, or a case where the development pattern is brought into contact after the separation film is peeled to perform the radiation curing.
  • the development pattern When radiation curing is performed by bringing the development pattern into contact, if the dry film has tack, the development pattern may be contaminated. Therefore, a dry film type photosensitive solder resist that requires less dry film tack is required. Is done.
  • a known radiation curing method can be used.
  • an electron beam, ultraviolet rays, or visible light of 400 to 500 nm can be used.
  • a thermionic emission gun, a field emission gun, or the like can be used as the electron beam source to be irradiated.
  • a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a metal halide lamp, a gallium lamp, a xenon lamp, a carbon arc lamp, or the like can be used as a source (light source) of ultraviolet light and visible light of 400 to 500 nm.
  • an ultra-high pressure mercury lamp, a xenon mercury lamp, or a metal halide lamp is often used because of the point light source and the stability of luminance.
  • the irradiation dose of active energy can be set in a timely range of 5 to 2000 mJ / cm 2 , but is preferably in the range of 50 to 1000 mJ / cm 2 that is easy to manage in the process. Further, these active energy rays can be used in combination with heat by infrared rays, far infrared rays, hot air, high-frequency heating or the like.
  • the dry film type photosensitive solder resist forms a pattern by developing after radiation curing, and forms a film having excellent resistance by heat curing as post-cure.
  • Post curing is preferably performed at 100 ° C. to 200 ° C. for 30 minutes to 2 hours.
  • radiation irradiation can be performed as necessary even after the post cure. By performing radiation irradiation after post cure, solder heat resistance and the like can be further improved.
  • the molecular weight of the resin is a polystyrene-equivalent weight average molecular weight measured by GPC (gel permeation chromatography).
  • the number average molecular weight (Mn) and the weight average molecular weight (Mw) are values in terms of polystyrene measured by GPC-8020 manufactured by Tosoh Corporation.
  • reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean Stark tube, a reflux condenser, and a gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C.
  • the slurry-like product produced in the container was taken out and dried in vacuum. 260 parts of this product was placed in the reaction vessel again and melted by heating to 150 ° C. with stirring. In this, 89 parts of phenyl isocyanate was dripped from the dripping apparatus over 1 hour. After dropping, the mixture was stirred at 150 ° C. for 1 hour, and 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. The temperature was lowered to 60 ° C. and methyl ethyl ketone was added to adjust the NV to 80%. The obtained uniform yellowish brown transparent solution was taken out.
  • the slurry-like product produced in the container was taken out and dried in vacuum. 414 parts of this product was again placed in the reaction vessel and melted by heating to 150 ° C. with stirring. In this, 284 parts of isostearic acid was dripped from the dripping apparatus over 1 hour. After dropping, the mixture was stirred at 150 ° C. for 1 hour, and 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. The temperature was lowered to 60 ° C. and methyl ethyl ketone was added to adjust the NV to 80%. The obtained uniform yellowish brown transparent solution was taken out.
  • a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube was charged with 203 parts of terephthalic acid dichloride, 316 parts of pyridine, and 1459 parts of dichloromethane and stirred on ice. 210 parts of diethanolamine was added dropwise from the dropping device over 2 hours. Then, it stirred at 25 degreeC for 5 hours, and reaction was completed.
  • the dichloromethane solution was washed with 2000 parts of 10% hydrochloric acid, 2000 parts of a saturated aqueous sodium hydrogen carbonate solution and 2000 parts of saturated brine, and then dried over anhydrous magnesium sulfate.
  • the dichloromethane of the solvent was removed with a rotary evaporator, and the product was recovered. 340 parts of this product was again placed in the reaction vessel and melted by heating to 150 ° C. with stirring. In this, 284 parts of stearic acid was added over 1 hour. After stirring at 150 ° C. for 1 hour, 1H-NMR measurement was performed, and it was confirmed that the target product was produced. Further, the structure was confirmed by IR. The temperature was lowered to 60 ° C. and methyl ethyl ketone was added to adjust the NV to 80%. The obtained uniform yellowish brown transparent solution was taken out.
  • the slurry-like product produced in the container was taken out and dried in vacuum. 401 parts of this product was placed in the reaction vessel again and melted by heating to 150 ° C. with stirring. In this, 282 parts of oleic acid was dripped from the dripping apparatus over 1 hour. After dropping, the mixture was stirred at 150 ° C. for 1 hour, and 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. The temperature was lowered to 60 ° C. and methyl ethyl ketone was added to adjust the NV to 80%. The obtained uniform yellowish brown transparent solution was taken out.
  • the slurry-like product produced in the container was taken out and dried in vacuum. 346 parts of this product was placed in the reaction vessel again and melted by heating to 150 ° C. with stirring. In this, 280 parts of linoleic acid was dripped from the dripping apparatus over 1 hour. After dropping, the mixture was stirred at 150 ° C. for 1 hour, and 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. The temperature was lowered to 60 ° C. and methyl ethyl ketone was added to adjust the NV to 80%. The obtained uniform yellowish brown transparent solution was taken out.
  • a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube was charged with 400 parts of diisopropanolamine, 10 parts of potassium hydroxide, and 176 parts of tricarballylic acid, and the temperature was raised to 120 ° C. After heating and heating for 4 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water formed by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • the slurry-like product produced in the container was taken out and dried in vacuum. 791 parts of this product was placed in the reaction vessel again and melted by heating to 150 ° C. with stirring. To this, 513 parts of cyclohexanecarboxylic acid was added over 1 hour. After dropping, the mixture was stirred at 150 ° C. for 1 hour, and 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. The temperature was lowered to 60 ° C. and methyl ethyl ketone was added to adjust the NV to 80%. The obtained uniform yellowish brown transparent solution was taken out.
  • a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube was charged with 210 parts of diethanolamine, 10 parts of potassium hydroxide, and 561 parts of dimer acid, and the temperature was raised to 120 ° C. After heating for 100 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water formed by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum. 735 parts of this product was again placed in the reaction vessel and melted by heating to 150 ° C. with stirring.
  • a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube was charged with 315 parts of diethanolamine, 10 parts of potassium hydroxide, and 192 parts of citric acid, and the temperature was raised to 120 ° C. 4 After heating for 100 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water formed by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • the slurry-like product produced in the container was taken out and dried in vacuum. 707 parts of this product, 152 parts of N-methylolacrylamide, 2 parts of ammonium p-toluenesulfonate, and 2 parts of p-methoxyphenol were added and stirred at 100 ° C. for 6 hours, followed by 1H-NMR measurement to obtain the desired product. Was confirmed to be generated. Further, the structure was confirmed by IR. The temperature was lowered to 60 ° C. and methyl ethyl ketone was added to adjust the NV to 80%. The obtained uniform yellowish brown transparent solution was taken out.
  • reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean Stark tube, a reflux condenser, and a gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried.
  • reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, 210 parts of diethanolamine and 10 parts of sodium methoxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 230 parts of dimethyl sebacates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C.
  • Resin synthesis example 1 (A) Synthesis of resin having carboxylic acid 500 parts of methyl ethyl ketone was put into a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a reflux condenser, and a gas introduction tube, and nitrogen was blown at 70 ° C. for 1 hour. Stir with heating. Thereafter, a solution in which 374.4 parts of butyl acrylate, 25.6 parts of acrylic acid, 11.4 parts of 2,2′-azobis (2,4-dimethylvaleronitrile) and 100 parts of methyl ethyl ketone were mixed from a dropping device over 2 hours. And dripped. The mixture was further reacted at 70 ° C.
  • Resin Synthesis Example 2 (A) Synthesis of Resin Having Carboxylic Acid 500 parts of butyl carbitol was placed in a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a reflux condenser, and a gas introduction tube, and nitrogen was blown at 70 ° C. Stir with heating for 1 hour. Thereafter, a solution in which 374.4 parts of butyl acrylate, 25.6 parts of acrylic acid, 11.4 parts of 2,2′-azobis (2,4-dimethylvaleronitrile) and 100 parts of butyl carbitol were mixed was added from a dropping device. It was added dropwise over time. The mixture was further reacted at 70 ° C.
  • Resin synthesis example 3 Reference synthesis example: synthesis of resin having hydroxyl group 500 parts of methyl ethyl ketone was put into a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a reflux condenser, and a gas introduction tube at 70 ° C. while blowing nitrogen. Stir with heating for 1 hour. Thereafter, a solution in which 358.8 parts of butyl acrylate, 41.2 parts of 2-hydroxyethyl acrylate, 11.4 parts of 2,2′-azobis (2,4-dimethylvaleronitrile) and 100 parts of methyl ethyl ketone were mixed from a dropping device. It was dripped over 2 hours. The mixture was further reacted at 70 ° C.
  • Example 26 The solubility test, curing test, and storage stability test of (B) the modified ⁇ -hydroxyalkylamide of Example 1 were conducted.
  • the solubility test was performed as follows.
  • the curing test (1) was performed as follows.
  • the resin solution was prepared by blending so that the molar ratio of the resin to the carboxy group was 1: 1. 1 g of this solution was placed in an aluminum container. This container was placed in an oven at 150 ° C. for 1 hour to cure the resin. The cured film was washed with methyl ethyl ketone. The film remaining at the time of washing was marked with ⁇ , and the washed film was marked with x.
  • the curing test (2) was performed as follows. (B) Modified ⁇ -hydroxyalkylamide of Synthesis Example 1 and (A) Resin having carboxylic acid of Synthesis Example 2 (B) Hydroxyl group of modified ⁇ -hydroxyalkylamide and (A) Carboxylic acid
  • the resin solution was prepared by blending so that the molar ratio of the resin to the carboxy group was 1: 1. 1 g of this solution was placed in an aluminum container. This container was placed in an oven at 150 ° C. for 1 hour to cure the resin. The cured film was washed with methyl ethyl ketone. The film remaining at the time of washing was marked with ⁇ , and the washed film was marked with x.
  • the storage stability test was conducted as follows. The viscosity of the resin solution used in the curing test was measured. Thereafter, it was stored at 40 ° C. for 1 week, and the viscosity after 1 week was measured. When the viscosity change was within 5% compared to the viscosity before the test, the case where the viscosity was 5% or more was rated as x.
  • Example 27-50 The test was conducted in the same manner as in Example 26 except that (B) modified ⁇ -hydroxyalkylamide of Examples 2 to 25 was used instead of (B) modified ⁇ -hydroxyalkylamide of Example 1.
  • Example 1 The test was performed in the same manner as in Example 26 except that Duranate TPA-100 (isocyanate manufactured by Asahi Kasei Co., Ltd.) was used instead of (B) the modified ⁇ -hydroxyalkylamide of Example 1.
  • Duranate TPA-100 isocyanate manufactured by Asahi Kasei Co., Ltd.
  • Example 2 The test was performed in the same manner as in Example 26 except that Duranate TPA-B80E (block isocyanate manufactured by Asahi Kasei Co., Ltd.) was used instead of (B) the modified ⁇ -hydroxyalkylamide of Example 1.
  • Duranate TPA-B80E block isocyanate manufactured by Asahi Kasei Co., Ltd.
  • Examples 26 to 50 were satisfactory in all of the solubility test, the curing test (1), the curing test (2), and the storage stability test.
  • Reference examples 1 and 2 were the results of not curing in the curing test (2).
  • the boiling point is high (boiling point: 230.6 ° C.)
  • butyl carbitol having a hydroxyl group is used as a solvent, and the solvent does not volatilize sufficiently at the curing temperature (150 ° C.). This is probably because the isocyanate or blocked isocyanate and butyl carbitol reacted first and did not react with the carboxyl group of the resin.
  • isocyanate or blocked isocyanate cannot be used. Since ⁇ -hydroxyalkylamide does not react with a hydroxyl group but selectively reacts with a carboxyl group, a solvent having a hydroxyl group can be used.
  • Reference Examples 3 and 4 are examples using a crosslinking agent having an epoxy group.
  • Reference Example 3 was cured without a catalyst, but was not cured under the test conditions of this time. Although it was confirmed that the catalyst was sufficiently cured by adding a catalyst, on the other hand, it was a result of thickening in a storage stability test. Epoxy groups cannot be suppressed during storage by adding a catalyst, but ⁇ -hydroxyalkylamides do not react during storage and can be sufficiently reacted under curing conditions.
  • Reference Example 5 is an example in which an unmodified ⁇ -hydroxyalkylamide was used, but the unmodified product was poor in solubility in a solvent and was not evaluated.
  • the functional group of the resin is a hydroxyl group, but the hydroxyl group and ⁇ -hydroxyalkylamide do not react at 150 ° C. and cannot be cured.
  • the (B) modified ⁇ -hydroxyalkylamide of this embodiment has high solvent solubility, and the resin composition containing the (B) modified ⁇ -hydroxyalkylamide of this embodiment is curable and storage stable. It was found to be excellent in performance.
  • Embodiment II >> Example 1 Synthesis of Compound 1
  • Example 5 Synthesis of Compound 5
  • Example 6 Synthesis of Compound 6
  • Example 9 Synthesis of Compound 9
  • Reference example 1 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, 315 parts of trimellitic anhydride chloride, 79 parts of pyridine, and 300 parts of toluene were added and maintained at 40 ° C. 267 parts of N-ethylethanolamine was added dropwise from the dropping device over 2 hours. After completion of the dropping, the Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water generated by azeotropy.
  • Resin Synthesis Example 1 Synthesis of Resin Having Carboxylic Acid 500 parts of methyl ethyl ketone was put into a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a reflux condenser, and a gas introduction tube, and heated and stirred at 70 ° C. for 1 hour while blowing nitrogen. . Thereafter, a solution in which 374.4 parts of butyl acrylate, 25.6 parts of acrylic acid, 11.4 parts of 2,2′-azobis (2,4-dimethylvaleronitrile) and 100 parts of methyl ethyl ketone were mixed from a dropping device over 2 hours. And dripped. The mixture was further reacted at 70 ° C.
  • Resin Synthesis Example 2 Synthesis of Resin Having Carboxylic Acid
  • a reaction vessel equipped with a stirrer, thermometer, reflux condenser, and gas introduction tube was charged with 1002 of Kuraray polyol P-1010 (Kuraray Co., Ltd. hydroxyl value 112 mgKOH / g).
  • 1002 of Kuraray polyol P-1010 Kerat Co., Ltd. hydroxyl value 112 mgKOH / g.
  • 237 parts of dimethylol butanoic acid, 576 parts of isophorone diisocyanate, and 1815 parts of methyl ethyl ketone were heated to 80 ° C. under a nitrogen stream. Thereafter, 0.1 part of dibutyltin dilaurate was added.
  • Example 12 A solubility test, a curing test, and a storage stability test of the compound of Example 1 were performed.
  • the curing test (1) was performed as follows. A resin solution containing the compound 1 of Example 1 and the resin having the carboxylic acid of Synthetic Example 1 so that the molar ratio of the hydroxyl group of the compound 1 to the carboxyl group of the resin having the carboxylic acid is 1: 1. Was made. 1 g of this solution was placed in an aluminum container. The container was placed in an oven at 120 ° C., 150 ° C., and 180 ° C. for 1 hour to cure the resin. The cured film was covered with a metal mesh and immersed in methyl ethyl ketone for 24 hours. Thereafter, the aluminum container was dried at 60 ° C. for 3 hours, and the residual rate of the cured film in the aluminum container was measured. The film with a remaining rate of 0 to 20% was rated as x, the film with 21 to 40% as ⁇ , the film as 41 to 80% as ⁇ , and the film as 81 to 100% as ⁇ .
  • the storage stability test was conducted as follows. The viscosity of the resin solution used in the curing test was measured. Thereafter, it was stored at 40 ° C. for 1 week, and the viscosity after 1 week was measured. When the viscosity change was within 5% compared to the viscosity before the test, the case where the viscosity was 5% or more was rated as x.
  • Examples 13-22 A solubility test, a curing test, and a storage stability test were conducted in the same manner as in Example 12 except that the compounds of Examples 2 to 10 were used instead of the compound 1 synthesized in Example 1.
  • Reference Example 3 is an example in which a commercially available adipic acid derivative substituted with ⁇ -hydroxyalkylamide was used. However, from the results of Reference Example 2, the solubility in a solvent was poor and the evaluation was not achieved.
  • any of the crosslinkable compositions using a compound in which X in the formula (1) has a linear aliphatic hydrocarbon group having 6 or more carbon atoms exhibits curing characteristics at a relatively low temperature such as 120 ° C. It became clear.
  • Example 23 A curing test and a storage stability test of Compound 1 of Example 1 were performed.
  • the curing test (2) was performed as follows. Resin solution containing compound 1 of Example 1 and resin having carboxylic acid of resin synthesis example 2 so that the molar ratio of the hydroxyl group of compound 1 to the carboxyl group of the resin having carboxylic acid is 1: 1. Was made. 1 g of this solution was placed in an aluminum container. The container was placed in an oven at 120 ° C., 150 ° C., and 180 ° C. for 1 hour to cure the resin. The cured film was covered with a metal mesh and immersed in methyl ethyl ketone for 24 hours. Thereafter, the aluminum container was dried at 60 ° C. for 3 hours, and the residual rate of the cured film in the aluminum container was measured. The film with a remaining rate of 0 to 20% was rated as x, the film with 21 to 40% as ⁇ , the film as 41 to 80% as ⁇ , and the film as 81 to 100% as ⁇ .
  • the storage stability test was conducted as follows. The viscosity of the resin solution used in the curing test was measured. Thereafter, it was stored at 40 ° C. for 1 week, and the viscosity after 1 week was measured. When the viscosity change was within 5% compared to the viscosity before the test, the case where the viscosity was 5% or more was rated as x.
  • Examples 24-33 A solubility test, a curing test, and a storage stability test were conducted in the same manner as in Example 23 except that the compounds of Examples 2 to 10 were used instead of the compound 1 synthesized in Example 1.
  • Examples 23 to 33 were good in all of the curing test (2) and the storage stability test.
  • Reference Example 5 is an example in which a derivative obtained by substituting a commercially available adipic acid with ⁇ -hydroxyalkylamide was used, but the solubility in a solvent was poor and the evaluation was not achieved.
  • any crosslinkable composition using a compound in which X in formula (1) has an aliphatic hydrocarbon group having 6 or more carbon atoms exhibits curing characteristics at a relatively low temperature such as 120 ° C. Became.
  • a resin composition containing a resin having a carboxylic acid and the compound of this embodiment is excellent in solvent solubility, curability, and storage stability.
  • Resin synthesis example 1 (A) Synthesis of resin having carboxylic acid 500 parts of methyl ethyl ketone was put into a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a reflux condenser, and a gas introduction tube, and nitrogen was blown at 70 ° C. for 1 hour. Stir with heating. Thereafter, a solution in which 374.4 parts of butyl acrylate, 25.6 parts of acrylic acid, 11.4 parts of 2,2′-azobis (2,4-dimethylvaleronitrile) and 100 parts of methyl ethyl ketone were mixed from a dropping device over 2 hours. And dripped. The mixture was further reacted at 70 ° C.
  • Resin Synthesis Example 2 (A) Synthesis of Resin Having Carboxylic Acid 500 parts of butyl carbitol was placed in a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a reflux condenser, and a gas introduction tube, and nitrogen was blown at 70 ° C. Stir with heating for 1 hour. Thereafter, a solution in which 374.4 parts of butyl acrylate, 25.6 parts of acrylic acid, 11.4 parts of 2,2′-azobis (2,4-dimethylvaleronitrile) and 100 parts of butyl carbitol were mixed was added from a dropping device. It was added dropwise over time. The mixture was further reacted at 70 ° C.
  • Resin synthesis example 3 Reference synthesis example: synthesis of resin having hydroxyl group 500 parts of methyl ethyl ketone was put into a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a reflux condenser, and a gas introduction tube at 70 ° C. while blowing nitrogen. Stir with heating for 1 hour. Thereafter, a solution in which 358.8 parts of butyl acrylate, 41.2 parts of 2-hydroxyethyl acrylate, 11.4 parts of 2,2′-azobis (2,4-dimethylvaleronitrile) and 100 parts of methyl ethyl ketone were mixed from a dropping device. It was dripped over 2 hours. The mixture was further reacted at 70 ° C.
  • Example 20 The solubility test, curing test, and storage stability test of (B) ⁇ -hydroxyalkylamide of Example 1 were conducted.
  • the curing test (1) was performed as follows. (B) ⁇ -hydroxyalkylamide of Example 1 and (A) a resin having a carboxylic acid of Synthesis Example 1 are used as (B) a resin having a hydroxyl group of ⁇ -hydroxyalkylamide and (A) a carboxylic acid.
  • a resin solution was prepared by blending such that the molar ratio with the carboxyl group was 1: 1. 1 g of this solution was placed in an aluminum container. This container was placed in an oven at 150 ° C. for 1 hour to cure the resin. The cured film was washed with methyl ethyl ketone. The film remaining at the time of washing was marked with ⁇ , and the washed film was marked with x.
  • the curing test (2) was performed as follows. Resin having (B) ⁇ -hydroxyalkylamide of Example 1 and (A) carboxylic acid of Synthetic Example 2 is used as (B) hydroxyl group of ⁇ -hydroxyalkylamide and (A) resin having carboxylic acid.
  • a resin solution was prepared by blending such that the molar ratio with the carboxyl group was 1: 1. 1 g of this solution was placed in an aluminum container. This container was placed in an oven at 150 ° C. for 1 hour to cure the resin. The cured film was washed with methyl ethyl ketone. The film remaining at the time of washing was marked with ⁇ , and the washed film was marked with x.
  • the storage stability test was conducted as follows. The viscosity of the resin solution used in the curing test was measured. Thereafter, it was stored at 40 ° C. for 1 week, and the viscosity after 1 week was measured. When the viscosity change was within 5% compared to the viscosity before the test, the case where the viscosity was 5% or more was rated as x.
  • Examples 21-38 A solubility test and a curing test were performed in the same manner as in Example 20 except that (B) ⁇ -hydroxyalkylamide of Examples 2 to 19 was used instead of (B) ⁇ -hydroxyalkylamide synthesized in Example 1. A storage stability test was conducted.
  • Example 1 The test was performed in the same manner as in Example 7 except that Duranate TPA-100 (isocyanate manufactured by Asahi Kasei Co., Ltd.) was used instead of (B) ⁇ -hydroxyalkylamide in Example 1.
  • Duranate TPA-100 isocyanate manufactured by Asahi Kasei Co., Ltd.
  • Example 2 The test was conducted in the same manner as in Example 7 except that Duranate TPA-B80E (block isocyanate manufactured by Asahi Kasei Co., Ltd.) was used instead of (B) ⁇ -hydroxyalkylamide in Example 1.
  • Duranate TPA-B80E block isocyanate manufactured by Asahi Kasei Co., Ltd.
  • Example 3 The test was performed in the same manner as in Example 7 except that EOCN-1020 (epoxy resin manufactured by Nippon Kayaku Co., Ltd.) was used instead of (B) ⁇ -hydroxyalkylamide in Example 1.
  • EOCN-1020 epoxy resin manufactured by Nippon Kayaku Co., Ltd.
  • Examples 20 to 38 were good in all of the solubility test, the curing test (1), the curing test (2), and the storage stability test.
  • Reference examples 1 and 2 were the results of not curing in the curing test (2).
  • the boiling point is high (boiling point: 230.6 ° C.)
  • butyl carbitol having a hydroxyl group is used as a solvent, and the solvent does not volatilize sufficiently at the curing temperature (150 ° C.). This is probably because the isocyanate or blocked isocyanate and butyl carbitol reacted first and did not react with the carboxyl group of the resin.
  • isocyanate or blocked isocyanate cannot be used. Since ⁇ -hydroxyalkylamide does not react with a hydroxyl group but selectively reacts with a carboxyl group, a solvent having a hydroxyl group can be used.
  • Reference Examples 3 and 4 are examples using a crosslinking agent having an epoxy group.
  • Reference Example 3 was cured without a catalyst, but was not cured under the test conditions of this time. Although it was confirmed that the catalyst was sufficiently cured by adding a catalyst, on the other hand, it was a result of thickening in a storage stability test. Epoxy groups cannot be suppressed during storage by adding a catalyst, but ⁇ -hydroxyalkylamides do not react during storage and can be sufficiently reacted under curing conditions.
  • Reference Example 5 was an example in which a commercially available ⁇ -hydroxyalkylamide was used, but the solubility in a solvent was poor and the evaluation was not achieved.
  • the functional group of the resin is a hydroxyl group, but the hydroxyl group and ⁇ -hydroxyalkylamide do not react at 150 ° C. and cannot be cured.
  • the resin composition containing (A) a carboxylic acid-containing resin and (B) ⁇ -hydroxyalkylamide of this embodiment is excellent in solvent solubility, curability, and storage stability. I understood.
  • Synthesis example 2 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, N, N, N ′, N′-tetrakis (hydroxyethyl) adipamide (Primid XL-552 manufactured by Emschemy) ) 320 parts were added and heated to 150 ° C. with stirring to melt. In this, 144 parts of 2-ethylhexanoic acid was added dropwise from a dropping device over 1 hour. After dropping, the mixture was stirred at 150 ° C.
  • Synthesis example 3 The procedure was the same as in Synthesis Example 1 except that 144 parts of 2-ethylhexanoic acid was changed to 216 parts, until the process of removing all toluene. 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. Thereafter, the temperature was lowered to 60 ° C., and cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A3 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis example 4 The procedure was the same as in Synthesis Example 1 except that 144 parts of 2-ethylhexanoic acid was changed to 288 parts, until the process of removing all toluene. 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. Thereafter, the temperature was lowered to 60 ° C., and cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A4 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis example 5 Except for changing 144 parts of 2-ethylhexanoic acid to 72 parts, the same procedure as in Synthesis Example 1 was followed until all toluene was distilled off. 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. Thereafter, the temperature was lowered to 60 ° C., and cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A5 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 6 Under the same conditions as in Synthesis Example 1, the slurry-like product produced in the container was taken out and vacuum dried. A mixture of 320 parts of this product and 83 parts of isophthalic acid was again placed in the reaction vessel and melted by heating to 150 ° C. with stirring. After dropping, the mixture was stirred at 150 ° C. for 1 hour, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, all the toluene was distilled off. 1H-NMR measurement was performed to confirm that the target product was produced.
  • Synthesis example 7 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 266 parts of diisopropanolamine, 10 parts of potassium hydroxide and 202 parts of sebacic acid were placed at 120 ° C. for 4 hours. Heated. 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water formed by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • Synthesis example 8 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, 210 parts of diethanolamine and 10 parts of sodium methoxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 230 parts of dimethyl sebacates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C.
  • Synthesis Example 9 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 266 parts of diisopropanolamine, 10 parts of potassium hydroxide and 202 parts of sebacic acid were placed at 120 ° C. for 4 hours. Heated. 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water formed by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • Synthesis Example 10 Place 210 parts of 2-amino-2-methyl-1,3-propanediol and 10 parts of potassium hydroxide in a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube. After heating to 60 ° C., 100 parts of succinic anhydride was added little by little over 1 hour. After heating to 120 ° C. and heating for 4 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel.
  • the slurry-like product produced in the container was taken out and dried in vacuum. 260 parts of this product was placed in the reaction vessel again and melted by heating to 150 ° C. with stirring. In this, 89 parts of phenyl isocyanate was dripped from the dripping apparatus over 1 hour. After dropping, the mixture was stirred at 150 ° C. for 1 hour, and 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. Thereafter, the temperature was lowered to 60 ° C., and cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A10 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 11 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 242 parts of tris (hydroxymethyl) aminomethane, 10 parts of potassium hydroxide, 2,4-diethylglutaric acid 188 A portion was added and heated at 120 ° C. for 4 hours. 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water formed by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • Synthesis Example 12 In a reaction vessel equipped with a stirrer, thermometer, dripping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 334 parts of 2-amino-1-phenyl-1,3-propanediol and 10 parts of potassium hydroxide are placed. After heating to 60 ° C., 98 parts of maleic anhydride was added little by little over 1 hour. After heating to 120 ° C. and heating for 4 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel.
  • the slurry-like product produced in the container was taken out and dried in vacuum. 414 parts of this product was again placed in the reaction vessel and melted by heating to 150 ° C. with stirring. In this, 284 parts of isostearic acid was dripped from the dripping apparatus over 1 hour. After dropping, the mixture was stirred at 150 ° C. for 1 hour, and 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. The temperature was lowered to 60 ° C., and cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A12 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 13 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide are placed, heated to 60 ° C., and then 148 parts of phthalic anhydride. Was added in portions over 1 hour. After heating to 120 ° C. and heating for 4 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel.
  • the slurry-like product produced in the container was taken out and dried in vacuum. 340 parts of this product was again placed in the reaction vessel and melted by heating to 150 ° C. with stirring. In this, 88 parts of butyric acid was dripped from the dripping apparatus over 1 hour. After dropping, the mixture was stirred at 150 ° C. for 1 hour, and 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. The temperature was lowered to 60 ° C., and cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A13 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 14 266 parts of diisopropanolamine, 10 parts of potassium hydroxide, and 166 parts of isophthalic acid are placed in a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube at 120 ° C. for 4 hours. Heated. 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water formed by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • Synthesis Example 15 A reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube was charged with 203 parts of terephthalic acid dichloride, 316 parts of pyridine, and 1459 parts of dichloromethane and stirred on ice. 210 parts of diethanolamine was added dropwise from the dropping device over 2 hours. Then, it stirred at 25 degreeC for 5 hours, and reaction was completed. The dichloromethane solution was washed with 2000 parts of 10% hydrochloric acid, 2000 parts of saturated aqueous sodium hydrogen carbonate solution and 2000 parts of saturated brine, and then dried over anhydrous magnesium sulfate.
  • the dichloromethane of the solvent was removed with a rotary evaporator, and the product was recovered. 340 parts of this product was again placed in the reaction vessel and melted by heating to 150 ° C. with stirring. In this, 284 parts of stearic acid was added over 1 hour. After stirring at 150 ° C. for 1 hour, 1H-NMR measurement was performed, and it was confirmed that the target product was produced. Further, the structure was confirmed by IR. The temperature was lowered to 60 ° C., and cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A15 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 16 Into a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 363 parts of tris (hydroxymethyl) aminomethane and 10 parts of potassium hydroxide were placed and heated to 60 ° C. 192 parts of trimellitic anhydride were added in portions over 1 hour. After heating to 120 ° C. and heating for 4 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • Synthesis Example 17 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 469 parts of N-butylethanolamine, 10 parts of potassium hydroxide, 1,2,3,4-butanetetra After charging 234 parts of carboxylic acid and heating to 120 ° C. and heating for 4 hours, 100 parts of toluene was added, and the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • Synthesis Example 18 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 357 parts of N-ethylethanolamine and 10 parts of potassium hydroxide are placed, heated to 60 ° C. and then anhydrous 218 parts of pyromellitic acid was added in portions over 1 hour. After heating to 120 ° C. and heating for 4 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel.
  • Synthesis Example 19 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 533 parts of diisopropanolamine and 10 parts of potassium hydroxide are placed, heated to 60 ° C., and then 3 or 3 294 parts of ', 4,4'-biphenyltetracarboxylic anhydride was added in portions over 1 hour. After heating to 120 ° C. and heating for 4 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel.
  • Synthesis Example 20 A reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube was charged with 315 parts of diethanolamine, 10 parts of potassium hydroxide, and 192 parts of citric acid, and the temperature was raised to 120 ° C. 4 After heating for 100 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water formed by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • Synthesis Example 21 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 703 parts of 2-amino-4-methyl-1-pentanol, 10 parts of potassium hydroxide, cyclohexane-1 , 2,3,4,5,6-hexacarboxylic acid 348 parts, heated to 120 ° C. and heated for 4 hours, 500 parts of toluene was added, the Dean-Stark tube was filled with toluene, and azeotroped with toluene The generated water was removed. The refluxed toluene was returned to the reaction vessel.
  • the slurry-like product produced in the container was taken out and dried in vacuum. 943 parts of this product, 373 parts of 2-ethylhexyl glycidyl ether, and 20 parts of zinc tetrafluoroborate were added and reacted at 100 ° C. for 6 hours. 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. Thereafter, the temperature was lowered to 60 ° C., and cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A21 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 22 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried.
  • Synthesis Example 23 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, N, N, N ′, N′-tetrakis (hydroxyethyl) adipamide (Primid XL-552 manufactured by Emschemy) 320 parts were added and heated to 150 ° C. with stirring to melt.
  • Synthesis Example 24 Under the same conditions as in Synthesis Example 22, the slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C. While blowing dry air, 119 parts of 3,5,5-methylhexanoic acid (Kyowa Noic-N manufactured by Kyowa Hakko Chemical Co., Ltd.), 2-acryloyloxyethyl succinic acid (HO-MS manufactured by Kyoeisha Chemical Co., Ltd.) A mixture of 173 parts and methoquinone 0.3 part was added dropwise from a dropping device over 1 hour. After dropping, the mixture was stirred at 150 ° C.
  • 3,5,5-methylhexanoic acid Korean Noic-N manufactured by Kyowa Hakko Chemical Co., Ltd.
  • 2-acryloyloxyethyl succinic acid HO-MS manufactured by Kyoeisha Chemical Co., Ltd.
  • Synthesis Example 25 Under the same conditions as in Synthesis Example 22, the slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C. While blowing dry air, 133 parts of Jamaicacid DDSA (manufactured by Shin Nippon Chemical Co., Ltd.) was dropped into the reactor over 1 hour. After the dropwise addition, a mixture of 78 parts of 2-methacryloyloxyethyl isocyanate (Karenz MOI manufactured by Showa Denko KK) and 0.3 part of methoquinone was added dropwise from the dropping device over 1 hour. After dropping, the mixture was stirred at 150 ° C. for 1 hour.
  • Synthesis Example 26 Under the same conditions as in Synthesis Example 22, the slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C. Into this, 361 parts of n-octanoic acid was dropped from a dropping device over 1 hour. After dropping, the mixture was stirred at 150 ° C. for 1 hour, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, all the toluene was distilled off.
  • Synthesis Example 27 Under the same conditions as in Synthesis Example 22, the slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C. In this, 144 parts of 2-ethylhexanoic acid was added dropwise from a dropping device over 1 hour. After dropping, the mixture was stirred at 150 ° C. for 1 hour, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, all the toluene was distilled off.
  • Synthesis Example 29 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 266 parts of diisopropanolamine and 10 parts of potassium hydroxide were placed, heated to 60 ° C., and then 4-cyclohexene 152 parts of -1,2-dicarboxylic anhydride were added in portions over 1 hour. After heating to 120 ° C. and heating for 4 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel.
  • the slurry-like product produced in the container was taken out and dried in vacuum. 401 parts of this product was placed in the reaction vessel again and melted by heating to 150 ° C. with stirring. In this, 282 parts of oleic acid was dripped from the dripping apparatus over 1 hour. After dropping, the mixture was stirred at 150 ° C. for 1 hour, and 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. The temperature was lowered to 60 ° C., and cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A29 containing a uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 30 In a reaction vessel equipped with a stirrer, thermometer, dripping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed, heated to 60 ° C., and then cyclohexane-1,2 -154 parts of dicarboxylic anhydride were added in portions over 1 hour. After heating to 120 ° C. and heating for 4 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel.
  • the slurry-like product produced in the container was taken out and dried in vacuum. 346 parts of this product was placed in the reaction vessel again and melted by heating to 150 ° C. with stirring. In this, 280 parts of linoleic acid was dripped from the dripping apparatus over 1 hour. After dropping, the mixture was stirred at 150 ° C. for 1 hour, and 1H-NMR measurement was performed to confirm that the target product was produced. Further, the structure was confirmed by IR. The temperature was lowered to 60 ° C., and cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A30 containing a uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 31 A reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube was charged with 400 parts of diisopropanolamine, 10 parts of potassium hydroxide, and 176 parts of tricarballylic acid, and the temperature was raised to 120 ° C. After heating and heating for 4 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water formed by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • Synthesis Example 32 A reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube was charged with 210 parts of diethanolamine, 10 parts of potassium hydroxide, and 561 parts of dimer acid, and the temperature was raised to 120 ° C. After heating for 100 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water formed by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum. 735 parts of this product was again placed in the reaction vessel and melted by heating to 150 ° C.
  • Synthesis Example 33 After putting 421 parts of 2-amino-1-butanol and 10 parts of potassium hydroxide in a reaction vessel equipped with a stirrer, thermometer, dripping device, Dean-Stark tube, reflux condenser, and gas introduction tube, and heating to 60 ° C. 3,3 ′, 4,4′-benzophenonetetracarboxylic anhydride 322 parts was added in portions over 1 hour. After heating to 120 ° C. and heating for 4 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel.
  • the slurry-like product produced in the container was taken out and dried in vacuum. 707 parts of this product, 152 parts of N-methylolacrylamide, 2 parts of ammonium p-toluenesulfonate, and 2 parts of p-methoxyphenol were added and stirred at 100 ° C. for 6 hours, followed by 1H-NMR measurement to obtain the desired product. Was confirmed to be generated. Further, the structure was confirmed by IR. The temperature was lowered to 60 ° C., and cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A33 containing a uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 34 225 parts of dimethyl suberate, 234 parts of diethanolamine, 10 parts of potassium hydroxide, and 300 parts of toluene are placed in a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube. The tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A34 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 35 The process was the same as in Synthesis Example 34 except that 225 parts of dimethyl suberate was changed to 256 parts of dimethyl sebacate. 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A35 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 36 The process was the same as in Synthesis Example 34 except that 225 parts of dimethyl suberate was changed to 287 parts of dimethyl dodecanedioate. 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A36 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 37 The process was the same as in Synthesis Example 34 except that 225 parts of dimethyl suberate was changed to 319 parts of dimethyl tetradecandioate. 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A37 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 38 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 572 parts of hexadecanoic acid, 532 parts of diisopropanolamine, 5 parts of sulfuric acid, and 300 parts of toluene are added. The tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A38 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 39 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 100 parts of dimethyl 1,4-cyclohexanedicarboxylate, 117 parts of 2- (butylamino) ethanol, potassium hydroxide Ten parts of toluene and 300 parts of toluene were added, and the Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A39 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 40 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 319 parts of dimethyl dodecanedioate, 151 parts of 2-aminoethanol, 10 parts of potassium hydroxide and 300 parts of toluene The Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A40 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 42 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 319 parts of dimethyl hexadecanoate, 278 parts of N-phenylethanolamine, 10 parts of potassium hydroxide, 300 parts of toluene The Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A42 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 43 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, gas introduction tube, 319 parts 1,3,5-cyclohexanetricarboxylic acid, 607 parts N-phenylethanolamine, 10 potassium hydroxide And 300 parts of toluene were added, and the Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A43 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 44 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, gas introduction tube, 319 parts of 1,2,3,4,5,6-cyclohexanehexacarboxylic acid monohydrate, isopropanol 412 parts of amine, 5 parts of sulfuric acid, and 300 parts of toluene were charged, and the Dean-Stark tube was filled with toluene, heated and refluxed while blowing nitrogen, and water generated by azeotropy was removed. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A44 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis example 45 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 188 parts of 2,4-diethylglutaric acid, 234 parts of N-butylethanolamine, 10 parts of potassium hydroxide, 300 parts of toluene was added, the Dean-Stark tube was filled with toluene, heated to reflux while blowing nitrogen, and water produced by azeotropy was removed. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A45 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 46 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, 268 parts of dodecyl succinic anhydride, 5 parts of sulfuric acid, and 300 parts of toluene were added and maintained at 40 ° C. 234 parts of 2-amino-4-methyl-1-pentanol was added dropwise from a dropping device over 2 hours. After completion of the dropping, the Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water generated by azeotropy.
  • Synthesis Example 47 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 230.3 parts 2-butyloctanedioic acid, 210 parts diisopropanolamine, 5 parts sulfuric acid, 300 parts toluene The Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A47 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 48 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 160 parts of 3-methyladipic acid, 302 parts of N-benzylethanolamine, 5 parts of sulfuric acid and 300 parts of toluene were added.
  • the Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%.
  • the obtained ⁇ -hydroxyalkylamide solution A48 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 49 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 204 parts of 4-tert-butyl phthalic anhydride, 5 parts of sulfuric acid, and 300 parts of toluene were placed at 40 ° C. While maintaining, 234 parts of 2-amino-3-methyl-1-pentanol was dropped from a dropping device over 2 hours. After completion of the dropping, the Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water generated by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A49 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis example 50 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, 204 parts of trimellitic anhydride chloride, 79 parts of pyridine, and 300 parts of toluene were kept at 40 ° C. 267 parts of N-ethylethanolamine was added dropwise from the dropping device over 2 hours. After completion of the dropping, the Dean-Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water generated by azeotropy.
  • Synthesis Example 51 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, gas introduction tube, 246 parts of cyclopentane-1,2,3,4-tetracarboxylic acid, 300 parts of N-methylaminoethanol Then, 5 parts of sulfuric acid and 300 parts of toluene were added, and the Dean-Stark tube was filled with toluene, heated and refluxed while blowing nitrogen, and water produced by azeotropy was removed. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A51 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 52 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, gas introduction tube, 345 parts tris (2-carboxyethyl) isocyanurate, 352 parts 2-butylaminoethanol, 5 parts sulfuric acid, 300 parts of toluene was added, the Dean-Stark tube was filled with toluene, heated to reflux while blowing nitrogen, and water produced by azeotropy was removed. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A52 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 53 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 561 parts of dimer acid, 266 parts of diisopropanolamine, 5 parts of sulfuric acid, and 300 parts of toluene were added, and Dean-Stark tube Was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A53 containing a uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 54 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 226 parts of 2-dodecenyl succinic anhydride, 210 parts of diethanolamine, 5 parts of sulfuric acid, and 300 parts of toluene are added.
  • the Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%.
  • the obtained ⁇ -hydroxyalkylamide solution A54 containing a uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 55 The process was repeated until all toluene was removed under the same conditions as in Synthesis Example 54, except that 226 parts of 2-dodecenyl succinic anhydride was changed to 226 parts of tetrapropenyl succinic anhydride. 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A55 containing a uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 56 The process was the same as in Synthesis Example 54 except that 226 parts of 2-dodecenyl succinic anhydride was changed to 210 parts of 2-octenyl succinic anhydride. 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A56 containing a uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 57 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 192 parts of citric acid, 352 parts of 2-butylaminoethanol, 5 parts of sulfuric acid, and 300 parts of toluene were added.
  • the Stark tube was filled with toluene and heated to reflux while blowing nitrogen to remove water produced by azeotropy. After 4 hours, all the toluene was removed, and 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%.
  • the obtained ⁇ -hydroxyalkylamide solution A57 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 58 All toluene was removed under the same conditions as in Synthesis Example 54 except that 226 parts of 2-dodecenyl succinic anhydride was changed to 166 parts of exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride. It went to the process to do. 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A58 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 59 The same procedure as in Synthesis Example 54 was followed until all toluene was removed, except that 226 parts of 2-dodecenyl succinic anhydride was changed to 290 parts of octafluoroadipic acid. 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A59 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 60 The process was repeated until all toluene was removed under the same conditions as in Synthesis Example 54, except that 226 parts of 2-dodecenyl succinic anhydride was changed to 370 parts of het acid anhydride. 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A60 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 61 The process was the same as in Synthesis Example 54 except that 226 parts of 2-dodecenyl succinic anhydride was changed to 464 parts of tetrabromophthalic anhydride until the process of removing all toluene. 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A61 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 62 The process was the same as in Synthesis Example 54 except that 226 parts of 2-dodecenyl succinic anhydride was changed to 172 parts of 2,5-thiophenedicarboxylic acid until the process of removing all toluene. 1H-NMR measurement and IR measurement were performed to confirm that the target product was produced. After cooling to 50 ° C., cyclohexanone was added to adjust the solid content to 20%. The obtained ⁇ -hydroxyalkylamide solution A62 containing no uniform yellowish brown transparent photopolymerizable functional group was taken out.
  • Synthesis Example 64 Put 100 parts of cyclohexanone into a reaction vessel equipped with a stirrer, thermometer, dropping device, reflux condenser, gas introduction tube, heat to 80 ° C. while injecting nitrogen gas into the vessel, and 25 parts of methacrylic acid at the same temperature, A mixture of 20 parts of 2-hydroxyethyl methacrylate, 30 parts of methyl methacrylate, 25 parts of styrene and 4 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour to carry out the polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C.
  • Synthesis Example 65 Put 100 parts of cyclohexanone into a reaction vessel equipped with a stirrer, thermometer, dropping device, reflux condenser, gas introduction tube, heat to 80 ° C. while injecting nitrogen gas into the vessel, and 40 parts of methacrylic acid at the same temperature, A mixture of 25 parts of methyl methacrylate, 12.5 parts of styrene, 17.5 parts of n-butyl methacrylate, 5 parts of 2-methoxyethyl acrylate, and 4 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour. The polymerization reaction was carried out. After completion of the dropwise addition, the mixture was further reacted at 80 ° C.
  • Synthesis Example 66 Put 100 parts of cyclohexanone into a reaction vessel equipped with a stirrer, thermometer, dropping device, reflux condenser, and gas introduction tube, heat to 80 ° C. while injecting nitrogen gas into the vessel, and 74 parts of glycidyl methacrylate at the same temperature, A mixture of 11 parts of methyl methacrylate, 7.5 parts of n-butyl methacrylate, 7.5 parts of benzyl methacrylate and 4 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour to carry out the polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C.
  • the solution was diluted with cyclohexanone to obtain a polymer solution P-4 containing a photopolymerizable functional group having a solid content of 20% and a carboxyl group.
  • the weight average molecular weight was 44,000.
  • Synthesis Example 68 A 4-necked flask equipped with a stirrer, reflux condenser, nitrogen inlet tube, inlet tube, thermometer, 40.08 parts of PEG # 250 (manufactured by NOF Corporation, ethylene glycol), Ricacid TH (Nippon Nippon Chemical Co., Ltd.) Made of tetrahydrophthalic anhydride), 1.66 parts of triphenylphosphine, 1.66 parts of N, N-dimethylbenzylamine as a catalyst, and 100 parts of cyclohexanone as a solvent. The temperature was raised to ° C. and reacted for 4 hours.
  • the mixture was cooled to room temperature.
  • the nitrogen from the nitrogen introduction tube was stopped in this flask and switched to introduction of dry air, while stirring, 27.05 parts of Bremmer G (manufactured by NOF Corporation, glycidyl methacrylate), and hydroquinone as a polymerization inhibitor in an amount of 0. 13 parts were added and reacted at 80 ° C. for 8 hours.
  • it was diluted with cyclohexanone to obtain a polymer solution P-6 containing an addition-type ester resin containing a photopolymerizable functional group having a solid content of 20% and a carboxyl group.
  • the weight average molecular weight was 14500.
  • Synthesis Example 69 In a four-necked flask equipped with a stirrer, reflux condenser, nitrogen inlet tube, inlet tube, and thermometer, 64.8 parts of bisphenol A, 57.1 parts of YD8125 (manufactured by Nippon Steel Chemical Co., Ltd., bisphenol A type epoxy compound) EX861 (manufactured by Nagase ChemteX Corporation: polyethylene glycol diglycidyl ether) 128.1 parts, 1.25 parts triphenylphosphine as catalyst, 1.25 parts N, N-dimethylbenzylamine, 250 parts cyclohexanone as solvent The mixture was heated to 110 ° C.
  • Reference synthesis example 1 Put 100 parts of cyclohexanone into a reaction vessel equipped with a stirrer, thermometer, dripping device, reflux condenser, and gas introduction tube, heat to 80 ° C. while injecting nitrogen gas into the vessel, and at the same temperature 2-hydroxyethyl methacrylate A mixture of 55.5 parts, 10 parts of methyl methacrylate, 19.5 parts of n-butyl methacrylate, 15 parts of benzyl methacrylate, and 4 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour to carry out the polymerization reaction. went. After completion of the dropwise addition, the mixture was further reacted at 80 ° C.
  • Photopolymerizable monomer (D) V # 802: Biscoat # 802 (Osaka Organic Chemical Co., Ltd.) Mixture of tripentaerythritol octaacrylate and tripentaerythritol heptaacrylate M402: Aronix M-402 (manufactured by Toa Gosei Co., Ltd.) Dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate Photopolymerization initiator (C): Irgacure OXE-01 (manufactured by Ciba Japan) 1,2-octadion-1- [4- (phenylthio)-, 2- (o-benzoyloxime)] Silane coupling agent: KBM-803 (manufactured by Shin-Etsu Chemical Co., Ltd.) 3-mercaptopropyltrimethoxysilane filler: PMA-ST (manufactured by Nissan Chemical
  • ⁇ Transmittance 97% or more: Good level ⁇ ; Transmittance 95% or more and less than 97%: Inferior to ⁇ , but practical level ⁇ ; Transmittance less than 95%: Unsuitable for practical use [chemical resistance evaluation ]
  • the thickness of the substrate obtained by the same method as that prepared for measuring transmittance was measured.
  • the film thickness was measured with a stylus type film thickness meter DEKTAK-3 manufactured by ULVAC.
  • the rank of evaluation is as follows.
  • ⁇ Appearance and color are not changed, and the absolute value of the film thickness change rate is less than 5%.
  • Good Good level.
  • ⁇ 4H or higher: Good level ⁇ ; 3H: Minimum practical hardness x; 2H or lower: Level not suitable for practical use [Measurement of adhesion to glass]
  • the adhesion of the coating film was evaluated by an adhesion (cross-cut method) test according to JIS K5600-5-6. The number of peeled pieces was counted.
  • ⁇ Number of cross-cuts peeled less than 2: Good level ⁇ ; Number of cross-cuts peeled 2 or more and 10 or less: Level inferior to ⁇ but practical level ⁇ ; Number of cross-cuts peeled over 10: Level not suitable for practical use [Insulation evaluation] About the board
  • this substrate was spray-developed using a sodium carbonate aqueous solution at 23 ° C., washed with ion-exchanged water, air-dried, and heated at 150 ° C. for 30 minutes in a clean oven.
  • the spray development was performed in the shortest time during which a pattern can be formed without any development remaining on the coating film of each photosensitive composition, and this was set as an appropriate development time.
  • the film thickness of the coating film was determined using Dektak 3030 (manufactured by Nippon Vacuum Technology Co., Ltd.).
  • the pattern film thickness at the formed 100 ⁇ m photomask portion was measured, and the minimum exposure amount at which the film thickness after coating was 90% or more was evaluated. The smaller the minimum exposure amount, the higher the sensitivity and the better the photosensitive composition.
  • the rank of evaluation is as follows.
  • Viscosity increase rate is less than 5%, good: Good level ⁇ : Viscosity increase rate is 5% or more, less than 10% Above: Level not suitable for practical use
  • the photosensitive compositions of Examples 1 to 20 contained the photopolymerizable monomer (D), the sensitivity during patterning was more excellent.
  • Reference Example 1 did not contain a photopolymerizable functional group and Reference Example 2 did not contain a photopolymerization initiator (C), patterning could not be performed. Moreover, since photocuring did not occur, the results were inferior in heat resistance and chemical resistance.
  • Diketopyrrolopyrrole pigment (CI Pigment Red 254) 6.82 parts ("Irga Four Red B-CF” manufactured by Ciba Japan) 1.08 parts of anthraquinone pigment (CI Pigment Red 177) (“Chromoval Red A2B” manufactured by Ciba Japan) Nickel azo complex pigment (CI Pigment Yellow 150) 0.88 parts (“E4GN” manufactured by LANXESS) Resin-type pigment dispersant (“Solsperse 20000” manufactured by Nippon Lubrizol) 1.74 parts Diketopyrrolopyrrole pigment derivative 2.05 parts
  • Halogenated copper phthalocyanine pigment (CI Pigment Green 36) 8.93 parts ("Rionol Green 6YK” manufactured by Toyo Ink Co., Ltd.) Monoazo pigment (CI Pigment Yellow 150) 2.74 parts (“E4GN” manufactured by LANXESS) Resin-type pigment dispersant (“Solsperse 20000” manufactured by Nippon Lubrizol Co., Ltd.) 2.80 parts Polymer solution P-1 5.53 parts Cyclohexanone 80.00 parts [Preparation of blue pigment dispersion] A blue pigment dispersion PB was prepared in the same manner as the red pigment dispersion using a mixture having the following composition.
  • a black pigment dispersion PK was prepared in the same manner as the red pigment dispersion, using a mixture having the following composition.
  • Dicyclopentanyl skeleton-containing novolak type epoxy resin Amine catalyst: Dimethylbenzylamine
  • Organic solvent Cyclohexanone and others 1: “PRIMID XL-552” (manufactured by Emschemy) N, N, N ′, N′-tetrakis (hydroxyethyl) adipamide and others 2: “XD-1000” manufactured by Nippon Kayaku Co., Ltd.
  • the obtained photosensitive composition for a color filter was evaluated for transparency, chemical resistance, hardness, adhesion, insulation, patterning suitability, and storage stability over time by the following methods. The results are shown in Tables 7 and 8.
  • ⁇ Haze value less than 0.5%: Good level ⁇ ; Haze value: 0.5% or more and less than 1.5%: Practical level that is inferior to ⁇ , but haze value: 1.5% or more: Practical use Is not suitable [chemical resistance evaluation]
  • the chromaticity of the substrate obtained by the same method as that prepared for measuring haze was measured. The substrate was immersed in an N-methylpyrrolidone solution at room temperature for 30 minutes, then washed with ion exchange water and air dried. Thereafter, the chromaticity of the substrate was measured, and the color difference ⁇ E was calculated. The chromaticity was measured with a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.) using a C light source. The rank of evaluation is as follows.
  • ⁇ Number of cross-cuts peeled less than 2: Good level ⁇ ; Number of cross-cuts peeled 2 or more and 10 or less: Inferior to ⁇ but practical level ⁇ ; Level not suitable for practical use [sensitivity during patterning] Using the color filter photosensitive compositions of Examples 25 to 91 and Reference Examples 9 to 16, the sensitivity was evaluated in the same manner as the coating agent for the touch panel interlayer insulating film.
  • the color filter photosensitive compositions of Examples 25 to 91 all have transparency, chemical resistance, heat resistance, adhesion, patterning sensitivity, pattern peeling, and storage stability. It was good.
  • the photosensitive compositions of Examples 25 to 56, 60 to 72, and 74 to 90 contain the photopolymerizable monomer (D), the sensitivity at the time of patterning was more excellent. Further, in Examples 26, 40, 46, 67, and 81, the peeling of the pattern is suppressed by the addition of the epoxy resin, and it may be used as long as the storage stability is not hindered.
  • Reference Example 9 did not contain a photopolymerizable functional group and Reference Example 10 did not contain a photopolymerization initiator (C), patterning could not be performed. Moreover, since photocuring did not occur, the results were inferior in heat resistance and chemical resistance.
  • ⁇ Photosensitive solder resist ink> [Examples 92 to 119, Reference Examples 17 to 24]
  • ⁇ -hydroxyalkylamide (A) and a polymer (B) containing a carboxyl group were blended, and Epicoat 1031S (manufactured by Mitsubishi Chemical Corporation, polyfunctional glycidyl ether) Type epoxy resin) 5 parts, BL3175 (manufactured by Sumika Bayer Urethane Co., Ltd., isocyanurate type block isocyanate), Irgacure 907 (manufactured by Ciba Specialty Chemicals Co., Ltd., 2-methyl-1- [4- (methylthio) ) Phenyl] -2-morpholino-1-propane) 2.5 parts, DETX-S (Nippon Kayaku Co., Ltd., 2,4-diethylthioxanthone) 0.25 parts, Aronix M-310 (Toagosei Co.,
  • XL-552 PRIMID XL-552 (manufactured by Ems Chemie) N, N, N ′, N′-tetrakis (hydroxyethyl) adipamide (evaluation method and results)
  • the resulting photosensitive composition was used as a photosensitive solder resist ink to evaluate developability, resolution, solder heat resistance, flexibility, and flame retardancy by the following methods.
  • an ultraviolet exposure device EXM-1201F manufactured by ORC Manufacturing Co., Ltd., short-circuited
  • the coating film is partially swollen or peeled off.
  • the whole coating film has swelling or peeling.
  • Sample B was folded 180 degrees and the same part was folded 180 degrees on the opposite side.
  • the state of the coating film at that time was judged according to the following criteria.
  • Sample C was evaluated for flame retardancy according to the UL Subject 94V method, and the results were judged according to the following criteria.
  • the photosensitive compositions of Examples 92 to 119 all have good developability, resolution, solder heat resistance, flexibility, and flame retardancy, and are flexible printed wiring boards. It has been shown that it is excellent as a flexible insulating protective film used for such as.
  • Embodiment V Average primary particle size measurement method
  • Propylene glycol monomethyl ether acetate was added to the pigment powder, a small amount of dispersant Disperbyk-161 (BIC Chemie's dispersant) was added, and the sample for measurement was prepared by ultrasonic treatment for 1 minute.
  • TEM transmission
  • three photographs (for 3 fields of view) in which primary particles of 100 or more pigments could be confirmed were prepared, and the size of 100 primary particles was measured sequentially from the upper left. Specifically, the minor axis diameter and major axis diameter of the primary particles of each pigment are measured in nm units, the average is the primary particle diameter of the pigment particles, and a total of 300 distributions are created in increments of 5 nm.
  • the median value in increments of 5 nm (for example, 8 nm in the case of 6 nm or more and 10 nm or less) was approximated as the particle diameter of those particles, and the number average particle diameter was calculated by calculating based on each particle diameter and the number thereof.
  • Synthesis example 2 In a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a Dean-Stark tube, a reflux condenser, and a gas introduction tube, N, N, N ′, N′-tetrakis (hydroxyethyl) adipamide (Primid XL-552 manufactured by Emschemy) ) 320 parts were added and heated to 150 ° C. with stirring to melt.
  • Synthesis example 3 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C.
  • Synthesis example 4 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C.
  • Synthesis example 5 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C.
  • Synthesis Example 6 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C.
  • Synthesis example 7 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C.
  • Synthesis example 8 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. A mixture of 320 parts of this product and 83 parts of isophthalic acid was again placed in the reaction vessel and melted by heating to 150 ° C. with stirring.
  • Synthesis Example 9 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 266 parts of diisopropanolamine, 10 parts of potassium hydroxide and 202 parts of sebacic acid were placed at 120 ° C. for 4 hours. Heated. 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water formed by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • Synthesis Example 10 After placing 178 parts of 1-amino-2-butanol and 10 parts of potassium hydroxide in a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, heating to 60 ° C. 100 parts of succinic anhydride was added little by little over 1 hour. After heating to 120 ° C. and heating for 4 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • Synthesis Example 11 Put 100 parts of cyclohexanone into a reaction vessel equipped with a stirrer, thermometer, dropping device, reflux condenser, gas introduction tube, heat to 80 ° C. while injecting nitrogen gas into the vessel, and 25 parts of methacrylic acid at the same temperature, A mixture of 20 parts of 2-hydroxyethyl methacrylate, 30 parts of methyl methacrylate, 25 parts of styrene and 4 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour to carry out the polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C.
  • the solution was diluted with cyclohexanone to obtain a polymer solution B2 containing a photopolymerizable functional group having a solid content of 20% and a carboxyl group.
  • the weight average molecular weight was 42,000.
  • Synthesis Example 12 Put 100 parts of cyclohexanone into a reaction vessel equipped with a stirrer, thermometer, dropping device, reflux condenser, gas introduction tube, heat to 80 ° C. while injecting nitrogen gas into the vessel, and 40 parts of methacrylic acid at the same temperature, A mixture of 25 parts of methyl methacrylate, 12.5 parts of styrene, 17.5 parts of n-butyl methacrylate, 5 parts of 2-methoxyethyl acrylate, and 4 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour. The polymerization reaction was carried out. After completion of the dropwise addition, the mixture was further reacted at 80 ° C.
  • Synthesis Example 13 Put 100 parts of cyclohexanone into a reaction vessel equipped with a stirrer, thermometer, dripping device, reflux condenser, gas introduction tube, heat to 80 ° C. while injecting nitrogen gas into the vessel, and at the same temperature, 68 parts of glycidyl methacrylate, A mixture of 17 parts of methyl methacrylate, 7.5 parts of n-butyl methacrylate, 7.5 parts of benzyl methacrylate and 4 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour to carry out the polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C.
  • a polymer solution B4 containing a photopolymerizable functional group having a solid content of 20% and a carboxyl group After cooling to room temperature, it was diluted with cyclohexanone to obtain a polymer solution B4 containing a photopolymerizable functional group having a solid content of 20% and a carboxyl group.
  • the weight average molecular weight was 44,000.
  • the mixture was further reacted at 80 ° C. for 3 hours, then 1 part of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour to obtain an acrylic resin solution.
  • the polymer solution b5 containing a hydroxyl group with a solid content of 20% was obtained by diluting with cyclohexanone.
  • the weight average molecular weight was 38000.
  • Pigment 1 11.0 parts Polymer solution (B1): 40 parts Propylene glycol monomethyl ether acetate (PGMAC): 48.0 parts Resin type dispersant (EFKA4300): 1.0 parts
  • V-1 hydroxyaluminum phthalocyanine pigment represented by the following formula (V-1)
  • 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70 ° C. for 6 hours. did.
  • the kneaded product is poured into 3000 parts of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. for a whole day and night. 2 was obtained.
  • the average primary particle size was 30.4 nm.
  • Pigment 2 11.0 parts Polymer solution (B1): 40 parts Propylene glycol monomethyl ether acetate (PGMAC): 48.0 parts Resin type dispersant (EFKA4300): 1.0 parts [Adjustment Example 3]
  • 100 parts of methanol and 100 parts of an aluminum phthalocyanine pigment represented by the formula (V-1) and 49.5 parts of diphenyl phosphate were added and heated to 40 ° C. and reacted for 8 hours. After cooling to room temperature, the product was filtered, washed with methanol, and dried to obtain 114 parts of a pigment represented by the following formula (V-2).
  • pigment 3 was obtained by the same salt milling method as pigment 2.
  • the average primary particle size was 31.2 nm.
  • Pigment 3 11.0 parts Polymer solution (B1): 40 parts Propylene glycol monomethyl ether acetate (PGMAC): 48.0 parts Resin type dispersant (EFKA4300): 1.0 parts [Adjustment Example 4]
  • PGMAC Propylene glycol monomethyl ether acetate
  • Resin type dispersant EFKA4300
  • V-3 a pigment represented by the following formula (V-3).
  • pigment 4 was obtained by the same salt milling method as pigment 2.
  • the average primary particle size was 29.5 nm.
  • Pigment 4 11.0 parts Polymer solution (B1): 40 parts Propylene glycol monomethyl ether acetate (PGMAC): 48.0 parts Resin type dispersant (EFKA4300): 1.0 parts [Preparation Example 5]
  • B1 40 parts Propylene glycol monomethyl ether acetate (PGMAC): 48.0 parts
  • Resin type dispersant (EFKA4300) 1.0 parts
  • C. I. 200 parts of Pigment Green 36, 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80 ° C. for 6 hours. Next, the kneaded product is put into 8 liters of warm water, stirred for 2 hours while heating to 80 ° C.
  • pigment dispersion (C-5) The mixture having the composition shown below was uniformly stirred and mixed, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 3 hours using zirconia beads having a diameter of 0.5 mm. Filtration through a filter gave a green pigment dispersion (C-5).
  • Pigment 5 11.0 parts Polymer solution (b5): 40 parts Propylene glycol monomethyl ether acetate (PGMAC): 48.0 parts Resin type dispersant (EFKA4300): 1.0 part [Preparation of photosensitive composition for color filter] ] [Examples 1 to 16 and Reference Examples 1 to 4] Each material was mixed and stirred at a formulation ratio shown in Table 1, and filtered through a 1 ⁇ m filter to obtain each colored composition.
  • PGMAC Propylene glycol monomethyl ether acetate
  • Resin type dispersant EFKA4300
  • Organic solvent Propylene glycol monomethyl ether acetate The resulting colored composition was evaluated by the following method.
  • ⁇ E * ab is less than 3.0 ⁇ : ⁇ E * ab is 3.0 or more and less than 5.0 ⁇ : The result of ⁇ E * ab is 5.0 or more is shown in Table 2.
  • Example 1 to 16 it comprises at least ⁇ -hydroxyalkylamide (A), a polymer (B) containing a carboxyl group, and a pigment represented by formula (17).
  • the color filter coloring composition had good light resistance, but did not contain any of ⁇ -hydroxyalkylamide (A) and carboxyl group-containing polymer (B) as in Reference Examples 1 to 3.
  • the sample formed from the composition had poor light resistance. Further, the coloring compositions of Examples 1 to 16 all had good sensitivity.
  • a coloring composition for a color filter comprising at least ⁇ -hydroxyalkylamide (A), a polymer (B) containing a carboxyl group, and a pigment represented by formula (17) in the coloring composition.
  • the coloring composition for a color filter comprising at least ⁇ -hydroxyalkylamide (A), a polymer (B) containing a carboxyl group, and a pigment represented by formula (17) in the coloring composition is light resistant. It is clear that the color filter can also provide a high quality and excellent sensitivity.
  • Synthesis example 2 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C.
  • Synthesis example 3 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C.
  • Synthesis example 4 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C.
  • Synthesis example 5 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C.
  • Synthesis Example 6 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. 320 parts of this product was again put into the reaction vessel and melted by heating and stirring at 150 ° C.
  • Synthesis example 7 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 210 parts of diethanolamine and 10 parts of potassium hydroxide were placed and heated to 100 ° C. while blowing nitrogen. In this, 174 parts of dimethyl adipates were dripped over 4 hours from the dripping apparatus. After completion of the dropwise addition, the reaction vessel was heated while being depressurized to 205 mmHg to remove the generated methanol. The slurry-like product produced in the container was taken out and vacuum dried. A mixture of 320 parts of this product and 83 parts of isophthalic acid was again placed in the reaction vessel and melted by heating to 150 ° C. with stirring.
  • Synthesis example 8 In a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, 266 parts of diisopropanolamine, 10 parts of potassium hydroxide and 202 parts of sebacic acid were placed at 120 ° C. for 4 hours. Heated. 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water formed by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • Synthesis Example 9 After placing 178 parts of 1-amino-2-butanol and 10 parts of potassium hydroxide in a reaction vessel equipped with a stirrer, thermometer, dropping device, Dean-Stark tube, reflux condenser, and gas introduction tube, heating to 60 ° C. 100 parts of succinic anhydride was added little by little over 1 hour. After heating to 120 ° C. and heating for 4 hours, 100 parts of toluene was added, the Dean-Stark tube was filled with toluene, and water produced by azeotroping with toluene was removed. The refluxed toluene was returned to the reaction vessel. After sufficiently removing water, the slurry-like product produced in the container was taken out and dried in vacuum.
  • Synthesis Example 11 Put 100 parts of cyclohexanone into a reaction vessel equipped with a stirrer, thermometer, dropping device, reflux condenser, gas introduction tube, heat to 80 ° C. while injecting nitrogen gas into the vessel, and 25 parts of methacrylic acid at the same temperature, A mixture of 20 parts of 2-hydroxyethyl methacrylate, 30 parts of methyl methacrylate, 25 parts of styrene and 4 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour to carry out the polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C.
  • the solution was diluted with cyclohexanone to obtain a polymer solution B-2 containing a photopolymerizable functional group having a solid content of 20% and a carboxyl group.
  • the weight average molecular weight was 42,000.
  • Synthesis Example 12 Put 100 parts of cyclohexanone into a reaction vessel equipped with a stirrer, thermometer, dropping device, reflux condenser, gas introduction tube, heat to 80 ° C. while injecting nitrogen gas into the vessel, and 40 parts of methacrylic acid at the same temperature, A mixture of 25 parts of methyl methacrylate, 12.5 parts of styrene, 17.5 parts of n-butyl methacrylate, 5 parts of 2-methoxyethyl acrylate, and 4 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour. The polymerization reaction was carried out. After completion of the dropwise addition, the mixture was further reacted at 80 ° C.
  • Synthesis Example 13 Put 100 parts of cyclohexanone into a reaction vessel equipped with a stirrer, thermometer, dripping device, reflux condenser, gas introduction tube, heat to 80 ° C. while injecting nitrogen gas into the vessel, and at the same temperature, 68 parts of glycidyl methacrylate, A mixture of 17 parts of methyl methacrylate, 7.5 parts of n-butyl methacrylate, 7.5 parts of benzyl methacrylate and 4 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour to carry out the polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C.
  • the solution was diluted with cyclohexanone to obtain a polymer solution B-4 containing a photopolymerizable functional group having a solid content of 20% and a carboxyl group.
  • the weight average molecular weight was 44,000.
  • Reference synthesis example 1 Put 100 parts of cyclohexanone into a reaction vessel equipped with a stirrer, thermometer, dripping device, reflux condenser, and gas introduction tube, heat to 80 ° C. while injecting nitrogen gas into the vessel, and at the same temperature 2-hydroxyethyl methacrylate A mixture of 55.5 parts, 10 parts of methyl methacrylate, 19.5 parts of n-butyl methacrylate, 15 parts of benzyl methacrylate, and 4 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour to carry out the polymerization reaction. went. After completion of the dropwise addition, the mixture was further reacted at 80 ° C.
  • Red fine pigment (F-2) Diketopyrrolopyrrole red pigment C.I. I. 120 parts of Pigment Red 254 (“IRGAZIN RED 2030” manufactured by Ciba Japan Co., Ltd.), 1000 parts of crushed salt and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. The mixture was added to 2000 parts of warm water, heated to about 80 ° C. and stirred with a high speed mixer for about 1 hour to form a slurry, filtered and washed repeatedly to remove salt and solvent, and then at 80 ° C. for 24 hours. It was dried to obtain 115 parts of a red fine pigment (F-2). The average primary particle diameter of the obtained pigment was 24.8 nm.
  • Nickel complex yellow pigment C.I. 100 parts of Pigment Yellow 150 (“E-4GN” manufactured by LANXESS), 700 parts of sodium chloride, and 180 parts of diethylene glycol were charged into a stainless gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80 ° C. for 6 hours. The mixture was added to 2000 parts of warm water, heated to about 80 ° C. and stirred with a high speed mixer for about 1 hour to form a slurry, filtered and washed repeatedly to remove salt and solvent, and then at 80 ° C. for 24 hours. It was dried to obtain 95 parts of yellow fine pigment (F-3). The average primary particle diameter of the obtained pigment was 39.2 nm.
  • Green refined pigment (F-4) Phthalocyanine green pigment C.I. I. 120 parts of Pigment Green 36 (“Lionol Green 6YK” manufactured by Toyo Ink Manufacturing Co., Ltd.), 1600 parts of sodium chloride, and 270 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70 ° C. for 12 hours. . The mixture was poured into 5000 parts of warm water, stirred at a high speed mixer for about 1 hour while being heated to about 70 ° C. to form a slurry, filtered and washed repeatedly to remove salt and solvent, and then at 80 ° C. for 24 hours. It dried and obtained 117 parts of green refined pigment (F-4). The average primary particle diameter of the obtained pigment was 32.6 nm.
  • Method for producing salt-forming resin (C1)> [Method for producing salt-forming resin (C1-1)] Into a four-necked separable flask equipped with a thermometer, a stirrer, a distillation tube, and a condenser, 67.3 parts of methyl ethyl ketone was charged and heated to 75 ° C. under a nitrogen stream.
  • salt-forming resin (C1-1) to 51 parts of side chain in 2000 parts of water, stir and mix thoroughly, and then heat to 60 ° C.
  • An aqueous solution in which Acid Red 289 is dissolved is prepared and added dropwise to the resin solution. After dropping, the mixture is stirred at 60 ° C. for 120 minutes to sufficiently react. In order to confirm the end point of the reaction, it was judged that a salt-forming compound was obtained with the reaction solution dropped onto the filter paper and the point where the bleeding disappeared as the end point.
  • a salt-forming resin (C1-2) is added to 2000 parts of a 10% aqueous methanol solution, and after sufficient stirring and mixing, the mixture is heated to 60 ° C.
  • 10 parts of C.I. in 90 parts of water 10 parts of C.I. in 90 parts of water.
  • An aqueous solution in which Acid Red 289 is dissolved is prepared and added dropwise little by little to the resin solution. After dropping, the mixture is stirred at 60 ° C. for 120 minutes to sufficiently react. In order to confirm the end point of the reaction, it was judged that a salt-forming compound was obtained with the reaction solution dropped onto the filter paper and the point where the bleeding disappeared as the end point.
  • a salt-forming resin (C1-3) 46.7 parts is added to 2000 parts of a 10% N, N-dimethylformamide aqueous solution, sufficiently stirred and mixed, and then heated to 70 ° C.
  • An aqueous solution in which acid red candy 289 is dissolved is prepared and added dropwise to the salt-forming resin (C1-3) solution. After dropping, the mixture is stirred at 70 ° C. for 120 minutes to sufficiently react. In order to confirm the end point of the reaction, the reaction solution was dropped onto the filter paper, and it was judged that the salt-forming compound was obtained with the point where the bleeding disappeared as the end point.
  • a solution in which 20.0 parts of the salt-forming resin (C1-4) is dissolved in 1000 parts of water is prepared, sufficiently stirred and mixed, and then heated to 70 ° C.
  • 10 parts of C.I. in 90 parts of water 10 parts of C.I. in 90 parts of water.
  • An aqueous solution in which Acid Red 289 is dissolved is prepared and added dropwise to the resin solution. After dropping, the mixture is stirred at 60 ° C. for 120 minutes to sufficiently react. In order to confirm the end point of the reaction, it was judged that a salt-forming compound was obtained with the reaction solution dropped onto the filter paper and the point where the bleeding disappeared as the end point.
  • C.I. I A salt-forming compound (Z-4) of Acid Red 289 and a salt-forming resin (C1-4) was obtained. At this time, C.I. I. The content of the effective pigment component derived from Acid Red 289 was 53% by weight.
  • a salt-forming resin (C1-1) is added to 2000 parts of a 10% aqueous methanol solution, and after sufficient stirring and mixing, the mixture is heated to 60 ° C.
  • 10 parts of C.I. in 90 parts of water 10 parts of C.I. in 90 parts of water.
  • An aqueous solution in which Acid Blue 112 is dissolved is prepared and added dropwise little by little to the previous resin solution. After dropping, the mixture is stirred at 60 ° C. for 120 minutes to sufficiently react. In order to confirm the end point of the reaction, it was judged that a salt-forming compound was obtained with the reaction solution dropped onto the filter paper and the point where the bleeding disappeared as the end point.
  • salt-forming resin C1-1
  • C.I. 10 parts of C.I. in 90 parts of water.
  • An aqueous solution in which Acid Blue 93 is dissolved is prepared and added dropwise little by little to the previous resin solution. After dropping, the mixture is stirred at 70 ° C. for 120 minutes to sufficiently react. In order to confirm the end point of the reaction, it was judged that a salt-forming compound was obtained with the reaction solution dropped onto the filter paper and the point where the bleeding disappeared as the end point.

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Abstract

La présente invention concerne un composé de formule (1), où X représente un groupement n-valent composé de C, H, N, O, S ou d'un atome d'halogène; n représente un entier compris entre 1 et 6; chacun des radicaux R1 et R2 représente H, un groupement représenté par la formule (2) ou la formule (3), ou un groupement hydrocarbure aliphatique, alicyclique ou aromatique; parmi une ou plusieurs entités R1 et R2 liées à un ou plusieurs atomes N, au moins une entité est un groupement représenté par la formule (2) et au moins une entité est un groupement représenté par la formule (3); chacun des radicaux R3 à R6 représente H ou un groupement hydrocarbure aliphatique; et R7 représente un résidu d'un composé qui comporte un groupement fonctionnel réactif avec OH.
PCT/JP2012/055480 2011-03-04 2012-03-02 β-HYDROXYALKYLAMIDE ET COMPOSITION DE RÉSINE WO2012121179A1 (fr)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104423170A (zh) * 2013-09-10 2015-03-18 奇美实业股份有限公司 感光性聚硅氧烷组合物、保护膜及具有保护膜的组件
CN104516198A (zh) * 2013-10-04 2015-04-15 达兴材料股份有限公司 感光树脂组合物及其形成的间隙物
KR20160081922A (ko) * 2013-11-15 2016-07-08 닛산 가가쿠 고교 가부시키 가이샤 액정 배향제 및 그것을 사용한 액정 표시 소자
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US9393252B2 (en) 2013-03-12 2016-07-19 Ecolab Usa Inc. Aromatic carboxylic acids in combination with aromatic hydroxyamides for inactivating non-enveloped viruses
US11298329B2 (en) 2013-03-12 2022-04-12 Ecolab Usa Inc. Antiviral compositions and methods for inactivating non-enveloped viruses using alkyl 2-hydroxycarboxylic acids
US10736860B2 (en) 2013-03-12 2020-08-11 Ecolab Usa Inc. Antiviral compositions and methods for inactivating non-enveloped viruses using alkyl 2-hydroxycarboxylic acids
CN104423170A (zh) * 2013-09-10 2015-03-18 奇美实业股份有限公司 感光性聚硅氧烷组合物、保护膜及具有保护膜的组件
CN104516198A (zh) * 2013-10-04 2015-04-15 达兴材料股份有限公司 感光树脂组合物及其形成的间隙物
KR20160081922A (ko) * 2013-11-15 2016-07-08 닛산 가가쿠 고교 가부시키 가이샤 액정 배향제 및 그것을 사용한 액정 표시 소자
KR102391044B1 (ko) * 2013-11-15 2022-04-26 닛산 가가쿠 가부시키가이샤 액정 배향제 및 그것을 사용한 액정 표시 소자
WO2016158863A1 (fr) * 2015-04-01 2016-10-06 東レ株式会社 Composition de résine colorée photosensible
US10613439B2 (en) 2015-04-01 2020-04-07 Toray Industries, Inc. Photosensitive colored resin composition
JP2017115039A (ja) * 2015-12-24 2017-06-29 株式会社フロロテクノロジー プリント配線板用保護コーティング剤
US20210061976A1 (en) * 2018-12-21 2021-03-04 Lg Chem, Ltd. Crosslinking agent compound, photosensitive composition comprising the same, and photosensitive material using the same
JP2021512179A (ja) * 2018-12-21 2021-05-13 エルジー・ケム・リミテッド 架橋剤化合物、これを含む感光性組成物、およびこれを利用した感光材料
JP7124871B2 (ja) 2018-12-21 2022-08-24 エルジー・ケム・リミテッド 架橋剤化合物、これを含む感光性組成物、およびこれを利用した感光材料
US11754921B2 (en) 2018-12-21 2023-09-12 Lg Chem, Ltd. Crosslinking agent compound, photosensitive composition comprising the same, and photosensitive material using the same

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