CN111560180A - Composition, cured product and article - Google Patents
Composition, cured product and article Download PDFInfo
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- CN111560180A CN111560180A CN202010084196.2A CN202010084196A CN111560180A CN 111560180 A CN111560180 A CN 111560180A CN 202010084196 A CN202010084196 A CN 202010084196A CN 111560180 A CN111560180 A CN 111560180A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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- 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
- C08K5/17—Amines; Quaternary ammonium compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/105—Esters; Ether-esters of monocarboxylic acids with phenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
Abstract
The invention provides a composition, a cured product and an article. The present disclosure provides a composition comprising: a conductive polymer/polyanion complex (a) composed of a polythiophene (a1) and a polymer (a2) containing a sulfo-anion group, wherein the polythiophene (a1) is represented by formula (1); an amine (B) represented by formula (2); a gallic acid ester compound (C) represented by the formula (3); and an organic solvent (D).
Description
Technical Field
The present disclosure relates to a composition, a cured product, and an article.
Background
The conductive polymer/polyanion complex composed of polythiophene and a polymer containing a sulfo anion group is excellent in transparency when formed into a thin film, and is therefore used in an antistatic coating agent. In an antistatic coating agent containing the conductive polymer/polyanion complex, various additives have been studied in order to maintain antistatic properties (patent document 1).
[ Prior art documents ]
[ patent document ]
[ patent document 1] International publication No. 2014/065314
Disclosure of Invention
[ problems to be solved by the invention ]
At present, when the additive (quercetin) described in patent document 1 is used, the antistatic property is maintained under heating conditions, but the additive is oxidized to produce a colored product, which results in a problem that the appearance of the coating film is impaired.
Accordingly, an object of the present invention is to provide a composition which maintains antistatic properties even under heating conditions and does not produce a colored product.
[ means for solving problems ]
The present inventors have conducted intensive studies and, as a result, have found that the above problems can be solved by a specific composition.
Through the present disclosure, the following items are provided.
(item 1)
A composition, comprising: a conductive polymer/polyanion complex (a) composed of a polythiophene (a1) and a polymer (a2) containing a sulfo-anion group, wherein the polythiophene (a1) is represented by formula (1); an amine (B) represented by formula (2); a gallic acid ester compound (C) represented by the formula (3); and an organic solvent (D).
[ solution 1]
(in the formula (1), A represents an alkylene group.)
[ solution 2]
(in the formula (2),X1is alkyl, alkenyl or aralkyl, Y1And Y2Each independently is a polyoxyalkylene group. )
[ solution 3]
(in the formula (3), R represents an alkyl group, an alkenyl group, an aryl group or an aralkyl group.)
(item 2)
The composition according to said item, comprising a compound (E) containing a polymerizable unsaturated carbon bond.
(item 3)
A cured product of the composition according to any one of the items.
(item 4)
An article comprising a hardened object according to the item.
In the present disclosure, the one or more features may be provided in further combination, in addition to the combinations explicitly shown.
[ Effect of the invention ]
The composition of the present embodiment maintains antistatic properties even under heating conditions and does not produce a colored product. Therefore, the composition of the present embodiment can be used as an antistatic coating agent or a conductive coating agent.
Detailed Description
In the entire disclosure, the ranges of numerical values such as the physical property values and the contents may be appropriately set (for example, selected from the upper limit and the lower limit described in the following items). Specifically, as for the numerical value α, when a1, a2, A3, A4 (a 1> a2> A3> A4) and the like are exemplified as the upper limit and the lower limit of the numerical value α, the range of the numerical value α is exemplified by a1 or less, a2 or less, A3 or less, a2 or more, A3 or more, A4 or more, a1 to a2, a1 to A3, a1 to A4, a2 to A3, a2 to A4, A3 to A4 and the like.
[ description of various groups ]
Alkyl groups include straight-chain alkyl groups, branched alkyl groups, cycloalkyl groups, and the like.
Straight chain alkyl radicalFormula (II): -CnH2n+1(n is an integer of 1 or more). Examples of the straight-chain alkyl group include methyl, ethyl, propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decamethyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl (stearyl), n-nonadecyl, n-eicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl and the like.
The branched alkyl group is a group in which one or more hydrogen atoms of a linear alkyl group are substituted with an alkyl group. Examples of the branched alkyl group include isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, neopentyl group, tert-pentyl group, isohexyl group and the like.
Cycloalkyl is an alkyl group having a ring structure. Examples of the cycloalkyl group include monocyclic cycloalkyl groups, crosslinked cyclic cycloalkyl groups, fused cyclic cycloalkyl groups, and the like. In addition, one or more hydrogen atoms of the cycloalkyl group may be substituted with a straight or branched alkyl group.
In the present disclosure, a monocyclic ring refers to a cyclic structure having no bridging structure inside the structure formed by covalent bonds of carbon. The condensed ring refers to a cyclic structure in which two or more monocyclic rings share two atoms (i.e., share (condense) only one side of each ring). The crosslinked ring is a cyclic structure in which two or more monocyclic rings share three or more atoms.
Monocyclic cycloalkyl groups exemplify cyclopentyl, cyclohexyl, cycloheptyl, cyclodecyl, 3,5, 5-trimethylcyclohexyl, and the like.
Examples of the crosslinked cycloalkyl group include tricyclodecyl group, adamantyl group, norbornyl group and the like.
Fused ring cycloalkyl groups are exemplified by bicyclodecyl and the like.
The alkenyl group is exemplified by a straight-chain alkenyl group, a branched alkenyl group, a cycloalkenyl group and the like.
The linear alkenyl group is represented by the general formula: -CnH2n-1(n is an integer of 2 or more). Examples of the linear alkenyl group include vinyl, allyl and n-buteneA group such as a phenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, an nonenyl group, and an decenyl group.
The branched alkenyl group is a group in which one or more hydrogen atoms of a linear alkenyl group are substituted with an alkyl group. Examples of the branched alkenyl group include 1-methylvinyl group and 1-methylallyl group.
Cycloalkenyl is alkenyl having a ring structure. Examples of the cycloalkenyl group include monocyclic cycloalkenyl group, crosslinked cycloalkenyl group, and fused cyclic cycloalkenyl group. In addition, more than one hydrogen atom of the cycloalkenyl group may be substituted by a straight or branched alkyl group.
Monocyclic cycloalkenyl groups exemplify cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like.
Examples of the crosslinked cycloalkenyl group include a norbornenyl group and the like.
Examples of the fused cyclic alkenyl group include bicyclodecenyl and the like.
Aralkyl is represented by the formula-Ralkylene-RarylThe group (R) representedalkyleneRepresents an alkylene group, RarylRepresents an aryl group).
Aryl is exemplified by monocyclic aryl, fused ring aryl and the like. One or more hydrogen atoms of the aryl group may be substituted with a straight or branched alkyl group.
Monocyclic aryl is exemplified by phenyl and the like.
The condensed ring aryl group exemplifies a naphthyl group and the like.
Aralkyl is exemplified by benzyl and the like.
The alkylene group is exemplified by a linear alkylene group, a branched alkylene group, a cycloalkylene group and the like.
The linear alkylene group is represented by the general formula: - (CH)2)n- (n is an integer of 1 or more). The straight chain alkylene group exemplifies methylene, ethylene, propylene, n-butylene, n-pentylene, n-hexylene, n-heptylene, n-octylene, n-nonylene, n-decamethylene, and the like.
The branched alkylene group is a group in which one or more hydrogen atoms of a linear alkylene group are substituted with an alkyl group. Examples of the branched alkylene group include diethylpentylene, trimethylbutylene, trimethylpentylene, trimethylhexylene and the like.
As the cycloalkylene group, a monocyclic cycloalkylene group, a crosslinked cyclic cycloalkylene group, a fused cyclic cycloalkylene group and the like are exemplified. In addition, one or more hydrogen atoms of the cycloalkylene group may be substituted with a straight-chain or branched alkyl group.
Monocyclic cycloalkylene is exemplified by cyclopentylene, cyclohexylene, cycloheptylene, cyclodecylene, 3,5, 5-trimethylcyclohexylene, and the like.
The crosslinked cycloalkylene group is exemplified by tricyclodecanyl group, adamantylene group, norbornylene group and the like.
The fused ring cycloalkylene group exemplifies a bicyclodecylene group and the like.
The number of carbons of the alkyl group, alkylene group, alkenyl group, alkenylene group, aryl group, and aralkyl group is not particularly limited, and the upper limit and the lower limit thereof are exemplified by 40, 35, 30, 29, 25, 20, 15, 12, 10, 9, 8, 7, 6, 5, 4, 3, 2, 1, and the like.
The polyoxyalkylene group is represented by the formula- [ R ]alkylene-O-]n-a group (R) representedalkyleneRepresents an alkylene group, and n represents an integer of 1 or more).
Examples of the polyoxyalkylene group include an oxyethylene group, an oxypropylene group, and an oxyethylene-oxypropylene group.
[ composition ]
The present disclosure provides a composition comprising: a conductive polymer/polyanion complex (a) composed of a polythiophene (a1) and a polymer (a2) containing a sulfo-anion group, wherein the polythiophene (a1) is represented by formula (1); an amine (B) represented by formula (2); a gallic acid ester compound (C) represented by the formula (3); and an organic solvent (D).
[ solution 4]
(in the formula (1), A represents an alkylene group.)
[ solution 5]
(in the formula (2), X1Is alkyl, alkenyl or aralkyl, Y1And Y2Each independently being polyoxyAn alkylene group. )
[ solution 6]
(in the formula (3), R represents an alkyl group, an alkenyl group, an aryl group or an aralkyl group.)
< conductive polymer/polyanion complex (A): also called component (A) >
(A) The component (a) is composed of a polythiophene (a1) as a conductive polymer and a polymer (a2) containing a sulfo anion group as a dopant. (A) The components may be used singly or in combination of two or more.
(Polythiophene (a 1): also referred to as component (a 1))
(a1) The component (A) is represented by the formula (1).
[ solution 7]
(in the formula (1), A is alkylene, A is preferably C1-C12 alkylene.)
(a1) The components may be used singly or in combination of two or more.
(a1) Examples of the component (A) include poly (3, 4-ethylenedioxythiophene), poly (3, 4-propylenedioxythiophene), and poly (3, 4-butylenedioxythiophene). Among them, Poly (3, 4-ethylenedioxythiophene) (Poly (3,4-ethylene dioxythiophene)) (hereinafter referred to as PEDOT) is particularly preferable in view of electrical conductivity.
(a1) The component (B) is obtained by a known chemical oxidative polymerization method or electrolytic polymerization method. In the former case, a method of synthesizing a conductive polymer in a solution containing a precursor monomer, a dopant and an oxidizing agent is exemplified, and in the latter case, a method of immersing a support electrode in an electrolytic solution containing a precursor monomer and a dopant and forming a conductive polymer thereon is exemplified. In the polymerization, water or the component (D) which is an organic solvent described later may be used as a solvent.
Examples of the oxidizing agent include metallic salt-based oxidizing agents [ e.g., ferric chloride, ferric sulfate, ferric nitrate, cupric chloride, and aluminum chloride ], and nonmetallic salt-based oxidizing agents [ e.g., ammonium peroxodisulfate, sodium peroxodisulfate, potassium peroxodisulfate, boron trifluoride, ozone, benzoyl peroxide, and oxygen ].
(sulfonic group-containing anionic group-containing Polymer (a 2): also referred to as component (a 2))
The sulfo anion group-containing polymer is a doping component with respect to the component (a 1). (a2) As the component (c), various known compounds such as a homopolymer of a sulfonic acid polymerizable monomer, a copolymer of a sulfonic acid polymerizable monomer and a polymerizable monomer having no sulfo anion group, and the like can be used without particular limitation. (a2) The components may be used singly or in combination of two or more.
Further, "sulfoanionic group" means a sulfo group or a monosubstituted sulfo ester group as an anionic functional group. The "monosubstituted sulfo ester group" refers to a group in which a hydrogen atom of a hydroxyl group in a sulfo ester group is substituted by an alkyl group (having about 1 to 20 carbon atoms).
Examples of the sulfonic acid-based polymerizable monomer include vinylsulfonic acid, (meth) allylsulfonic acid, styrenesulfonic acid, α -methylstyrenesulfonic acid, Methallyloxy (Methallyloxy) benzenesulfonic acid, allyloxybenzenesulfonic acid, 1, 3-butadiene-1-sulfonic acid, 1-methyl-1, 3-butadiene-2-sulfonic acid, 1-methyl-1, 3-butadiene-4-sulfonic acid, isoprenesulfonic acid, and ethylsulfonic acid (CH) of (meth) acrylic acid2＝C(CH3)-COO-(CH2)2-SO3H) (meth) acrylic acid propylsulfonic acid (CH)2＝C(CH3)-COO-(CH2)3-SO3H) (meth) acrylic acid-tert-butylsulfonic acid (CH)2＝C(CH3)-COO-C(CH3)2CH2-SO3H) N-butylsulfonic acid (CH) of (meth) acrylic acid2＝C(CH3)-COO-(CH2)4-SO3H) (meth) acrylic acid phenylene sulfonic acid (CH)2＝C(CH3)-COO-C6H4-SO3H) Naphthalene sulfonic acid (CH) of (meth) acrylic acid2＝C(CH3)-COO-C10H8-SO3H) Allyl ethyl sulfonic acid (CH)2＝CHCH2-COO-(CH2)2-SO3H) Allyl acid-tert-butyl sulfonic acid (CH)2＝CHCH2-COO-C(CH3)2CH2-SO3H) 4-pentenoic acid ethylsulfonic acid (CH)2＝CH(CH2)2-COO-(CH2)2-SO3H) 4-pentenoic acid propylsulfonic acid (CH)2＝CH(CH2)2-COO-(CH2)3-SO3H) 4-pentenoic acid-n-butylsulfonic acid (CH)2＝CH(CH2)2-COO-(CH2)4-SO3H) 4-pentenoic acid-tert-butyl sulfonic acid (CH)2＝CH(CH2)2-COO-C(CH3)2CH2-SO3H) 4-pentenoic acid phenylene sulfonic acid (CH)2＝CH(CH2)2-COO-C6H4-SO3H) 4-pentenoic acid naphthalenesulfonic acid (CH)2＝CH(CH2)2-COO-C10H8-SO3H) Acrylamide-tert-butyl sulfonic acid, 2-acrylamide-2-methylpropanesulfonic acid, cyclobutene-3-sulfonic acid, and salts thereof (such as sodium salt).
Examples of the polymerizable monomer having no sulfo anion group include aromatic monomers [ styrene, p-methylstyrene, p-ethylstyrene, p-butylstyrene, 2,4, 6-trimethylstyrene, p-methoxystyrene, α -methylstyrene, vinylphenol, 2-vinylnaphthalene, 6-methyl-2-vinylnaphthalene, etc. ], nonalicyclic dienes [1, 3-butadiene, 1-methyl-1, 3-butadiene, 2-methyl-1, 3-butadiene, 1, 4-dimethyl-1, 3-butadiene, 1, 2-dimethyl-1, 3-butadiene, 1, 3-dimethyl-1, 3-butadiene, 1-octyl-1, 3-butadiene, 1-methyl-1, 3-butadiene, etc. ], 2-octyl-1, 3-butadiene, 1-phenyl-1, 3-butadiene, 2-phenyl-1, 3-butadiene, 1-hydroxy-1, 3-butadiene, etc. ], non-alicyclic monoolefins [ 2-hydroxy-1, 3-butadiene, ethylene, propylene, 1-butene, 2-butene, 1-pentene, 2-pentene, 1-hexene, 2-hexene, etc. ], alicyclic monoolefins [ cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, 2-methylcyclohexene, etc. ], imidazole-based monomers [ 1-vinylimidazole, 2-vinylpyridine, 3-vinylpyridine, 4-vinylpyridine, N-vinyl-2-pyrrolidone, N-vinyl-1, 3-vinylpyridine, etc. ], a polymer having a high molecular weight, and a high molecular weight, N-vinylacetamide, N-vinylformamide, N-vinylimidazole, etc. ], acrylamides [ (meth) acrylamide, N-dimethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-vinylformamide, 3-acrylamidophenylboronic acid, etc. ], amine monomers [ acryloylmorpholine, vinylamine, N-dimethylvinylamine, N-diethylvinylamine, N-dibutylvinylamine, N-di-tert-butylvinylamine, N, n-diphenylvinylamine, N-vinylcarbazole, etc. ], other monomers [ vinyl acetate, acrolein, methacrolein, acrylonitrile, vinyl alcohol, vinyl chloride, vinyl fluoride, methyl vinyl ether, ethyl vinyl ether, etc. ], and the like.
The component (a2) is preferably selected from the group consisting of polystyrenesulfonic acid, polyvinylsulfonic acid, polyallylsulfonic acid, polyethylethylsulfonic acid, polybutylenesulfonic acid, poly-2-acrylamido-2-methylpropanesulfonic acid, and polyisoprenesulfonic acid, from the viewpoint of satisfactory doping performance and contributing to the stability of an organic solvent dispersion of the component (A) described later, at least one member selected from the group consisting of polyvinyl carboxylic acid, polystyrene carboxylic acid, polyallyl carboxylic acid, polyacrylic carboxylic acid, polymethacrylic carboxylic acid, poly-2-acrylamide-2-methylpropane carboxylic acid, polyisoprene carboxylic acid, polyacrylic acid, and salts thereof, and polystyrene sulfonic acid (polystyrene sulfonate) and/or salts thereof (particularly sodium salt) thereof are particularly preferable (hereinafter, sometimes collectively referred to as PSS).
The method of doping the component (a1) with the component (a2) is not particularly limited, and examples thereof include a method of adding the component (a2) to the component (a1) and stirring and mixing the mixture by various known methods, and a method of allowing the component (a2) to coexist in the reaction system during the production of the component (a1) (during the polymerization of the precursor monomer).
When the component (A) is prepared as an aqueous solution or an aqueous dispersion, an organic solvent dispersion can be prepared by various known methods (for example, Japanese patent laid-open Nos. 2008-045116, 2008-156452, 2008-222850, and 2011-208016). Specifically, for example, when an aqueous solution or an aqueous dispersion of PEDOT/PSS is used as the component (a), a blue solid of PEDOT/PSS can be obtained by drying the same by various known drying means (such as a spray dryer), and can be used as the component (a).
The component (a) is particularly preferably a complex of PEDOT and PSS (hereinafter referred to as PEDOT/PSS) in terms of chemical stability as a conductive polymer/dopant complex, conductivity, hue of a coating film made of the conductive composition of the present invention, transparency, and the like. Commercially available products of PEDOT/PSS include "Clevios (Clevios) P" (trade name: manufactured by Heraeus, Inc.), "Okaikang (Orgacon)" (trade name: manufactured by Agfa-Gevaert, Inc.).
The upper limit and the lower limit of the content of the component (a) in 100% by mass of the composition are exemplified by 5% by mass, 4.5% by mass, 4% by mass, 3.5% by mass, 3% by mass, 2.5% by mass, 2% by mass, 1.5% by mass, 1% by mass, 0.9% by mass, 0.5% by mass, 0.1% by mass, 0.09% by mass, 0.05% by mass, 0.04% by mass, 0.01% by mass, 0.005% by mass, 0.002% by mass and the like. In one embodiment, the content of the component (a) in 100% by mass of the composition is preferably 0.002% by mass to 5% by mass.
< amine (B): also referred to as component (B) >
(B) The component (C) is represented by the formula (2).
[ solution 8]
[ in the formula (2), X1Is alkyl (such as C1-C40 alkyl), alkenyl (such as C2-C40 alkenyl) or aralkyl (such as C7-C40 aralkyl), Y1And Y2Each independently is a polyoxyalkylene group.]
(B) The components may be used singly or in combination of two or more.
(B) The component (A) is exemplified by N, N-poly (oxyethylene) -hexylamine, N-poly (oxypropylene) -hexylamine, N-poly (oxyethylene-oxypropylene) -hexylamine, N-poly (oxyethylene) -decylamine, N-poly (oxypropylene) -decylamine, N-poly (oxyethylene-oxypropylene) -decylamine, N-poly (oxyethylene) -pentadecylamine, N-poly (oxypropylene) -pentadecylamine, N-poly (oxyethylene-oxypropylene) -pentadecylamine, N-poly (oxyethylene) -eicosylamine, N-poly (oxypropylene) -eicosylamine, N-poly (oxyethylene-oxypropylene) -eicosylamine, N, N-poly (oxyethylene) -hexacosanylamine, N-poly (oxypropylene) -hexacosanylamine, N-poly (oxyethylene-oxypropylene) -hexacosanylamine, N-poly (oxyethylene) -triacontosanylamine, N-poly (oxypropylene) -triacontosanylamine, N-poly (oxyethylene-oxypropylene) -triacontosanylamine, and the like.
The upper limit and the lower limit of the content of the component (B) in 100% by mass of the composition are exemplified by 10% by mass, 9.5% by mass, 9% by mass, 8.5% by mass, 8% by mass, 7.5% by mass, 7% by mass, 6.5% by mass, 6% by mass, 5.5% by mass, 5% by mass, 4.5% by mass, 4% by mass, 3.5% by mass, 3% by mass, 2.5% by mass, 2% by mass, 1.5% by mass, 1% by mass, 0.9% by mass, 0.5% by mass, 0.1% by mass, 0.09% by mass, 0.05% by mass, 0.04% by mass, 0.01% by mass, 0.005% by mass. In one embodiment, the content of the component (B) in 100% by mass of the composition is preferably 0.001% by mass to 10% by mass.
< gallate compound (C): also referred to as component (C) >
(C) The component (C) is represented by the formula (3).
[ solution 9]
(in the formula (3), R represents an alkyl group, an alkenyl group, an aryl group or an aralkyl group)
(C) The components may be used singly or in combination of two or more.
(C) Examples of the component (A) include alkyl gallate, alkenyl gallate, aryl gallate and aralkyl gallate.
Examples of the alkyl gallate include a linear alkyl gallate, a branched alkyl gallate, and a cycloalkyl gallate.
Examples of the linear alkyl esters of gallic acid include methyl gallate, ethyl gallate, propyl gallate, n-butyl gallate, n-pentyl gallate, n-hexyl gallate, n-heptyl gallate, n-octyl gallate, n-nonyl gallate, n-decyl gallate, n-undecyl gallate, n-dodecyl gallate, n-tridecyl gallate, n-tetradecyl gallate, n-pentadecyl gallate, n-hexadecyl gallate, n-heptadecyl gallate, n-octadecyl gallate (stearyl gallate), n-nonadecyl gallate, n-eicosyl gallate, n-heneicosyl gallate, n-docosyl gallate, n-tricosyl gallate, n-tetradecyl gallate, n-octyl gallate, n-dodecyl gallate, n-eicosyl gallate, n-docosyl gallate, n-tetradecyl gallate, n, N-pentacosyl gallate, n-hexacosyl gallate, n-heptacosyl gallate, n-dioctadecyl gallate, n-nonacosyl gallate, n-triacontyl gallate, and the like.
Examples of branched alkyl gallate include isopropyl gallate, isobutyl gallate, sec-butyl gallate, tert-butyl gallate, isoamyl gallate, neopentyl gallate, tert-amyl gallate, isohexyl gallate and the like.
Examples of the cycloalkyl gallate include cyclopentyl gallate, cyclohexyl gallate, cycloheptyl gallate, cyclodecyl gallate, 3,5, 5-trimethylcyclohexyl gallate, tricyclodecyl gallate, adamantyl gallate, norbornyl gallate, and bicyclodecyl gallate.
Examples of the gallic acid alkenyl ester include gallic acid vinyl ester, gallic acid allyl ester, and the like.
As aryl gallate, phenyl gallate and the like are exemplified.
Examples of the aralkyl gallate include benzyl gallate and the like.
The upper limit and the lower limit of the content of the component (C) in 100% by mass of the composition are exemplified by 5% by mass, 4.5% by mass, 4% by mass, 3.5% by mass, 3% by mass, 2.5% by mass, 2% by mass, 1.5% by mass, 1% by mass, 0.9% by mass, 0.5% by mass, 0.1% by mass, 0.09% by mass, 0.05% by mass, 0.04% by mass, 0.01% by mass, 0.005% by mass, 0.002% by mass, 0.001% by mass, and the like. In one embodiment, the content of the component (C) in 100% by mass of the composition is preferably 0.001% by mass to 5% by mass.
The upper and lower limits of the content of component (C) are 5000 mass%, 4000 mass%, 2500 mass%, 1000 mass%, 900 mass%, 750 mass%, 500 mass%, 400 mass%, 300 mass%, 250 mass%, 100 mass%, 90 mass%, 75 mass%, 73 mass%, 50 mass%, 30 mass%, 25 mass%, 10 mass%, 5 mass%, 2 mass%, 1 mass%, 0.1 mass%, 0.01 mass%, 0.002 mass%, and the like, with respect to 100 mass% of component (a). In one embodiment, the content of the component (C) is preferably 0.002 to 5000 mass% with respect to 100 mass% of the component (a).
< organic solvent (D): also referred to as component (D) >
(D) The components may be used singly or in combination of two or more. (D) The component (A) is exemplified by non-ether mono-alcohol solvents, non-ether glycol solvents, ether solvents, ketone solvents, alicyclic hydrocarbon solvents, ester solvents, nitrile solvents, nitrogen-containing compound solvents, sulfur-containing compound solvents, and the like.
Examples of the non-ether mono-alcohol solvent include methanol, ethanol, propanol, butanol, and isopropanol.
Examples of the non-ether glycol solvent include ethylene glycol, neopentyl glycol, propylene glycol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, diethylene glycol, and dipropylene glycol.
Examples of the ether solvent include dioxane, diethyl ether, ethylene glycol dialkyl ether, propylene glycol monomethyl ether, polyethylene glycol dialkyl ether, and polypropylene glycol dialkyl ether.
Examples of the ketone solvent include acetone, methyl ethyl ketone, and methyl isobutyl ketone.
The aromatic hydrocarbon solvent is exemplified by benzene, toluene, xylene, etc.
Examples of the alicyclic hydrocarbon solvent include cyclohexane and methylcyclohexane.
Examples of the ester solvent include ethyl formate and ethyl acetate.
Examples of the nitrile solvent include acetonitrile, glutaronitrile (glutaminic acid), methoxyacetonitrile, propionitrile, and benzonitrile.
Examples of the nitrogen-containing compound solvent include N-methyl-2-pyrrolidone, 3-methyl-2-oxazolidinone, N-dimethylformamide, N-dimethylacetamide, and the like.
Examples of the sulfur-containing compound solvent include dimethyl sulfoxide and the like.
The upper limit and the lower limit of the content of the component (D) in 100% by mass of the composition are 99.996% by mass, 99.9% by mass, 99% by mass, 95% by mass, 90% by mass, 85% by mass, 80% by mass, 75% by mass, 70% by mass, 65% by mass, 60% by mass, 55% by mass, 50% by mass, 45% by mass, 40% by mass, 35% by mass, 30% by mass, 25% by mass, 20% by mass, and the like. In one embodiment, the content of the component (D) in 100% by mass of the composition is preferably 20% by mass to 99.996% by mass.
< Compound (E) having a polymerizable unsaturated carbon bond: also known as component (E) >
In one embodiment, the composition may include a compound (E) containing a polymerizable unsaturated carbon bond. (E) The components may be used singly or in combination of two or more.
(E) The component (A) is exemplified by polymer poly (meth) acrylate, oligomer poly (meth) acrylate, and the like.
In the present disclosure, "(meth) acrylic acid" means "at least one selected from the group consisting of acrylic acid and methacrylic acid". Likewise, "(meth) acrylate" means "at least one selected from the group consisting of acrylate and methacrylate". Further, "(meth) acryloyl group" means "at least one selected from the group consisting of acryloyl groups and methacryloyl groups".
(Polymer Poly (meth) acrylate)
In the present disclosure, the "polymer poly (meth) acrylate" refers to a polymer having two or more (meth) acryloyl groups.
The polymer poly (meth) acrylate can be produced by a known method. The method for producing the polymer poly (meth) acrylate is exemplified by a method of reacting an epoxy group-containing (meth) acrylic acid copolymer with an α, β -unsaturated carboxylic acid, and the like. The epoxy group-containing (meth) acrylic copolymer can be produced by a known method using an epoxy group-containing (meth) acrylate.
The α, β -unsaturated carboxylic acid is exemplified by (meth) acrylic acid and the like.
Examples of the epoxy group-containing (meth) acrylate include glycidyl (meth) acrylate.
Examples of monomers usable for the production of other polymers poly (meth) acrylate include alkyl (meth) acrylate having no hydroxyl group, alkyl (meth) acrylate having a hydroxyl group, and the like.
Examples of the alkyl (meth) acrylate having no hydroxyl group include a straight-chain alkyl (meth) acrylate having no hydroxyl group, a branched alkyl (meth) acrylate having no hydroxyl group, a cycloalkyl (meth) acrylate having no hydroxyl group, and the like.
Examples of the linear alkyl (meth) acrylate having no hydroxyl group include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, n-butyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, hexadecyl (meth) acrylate, dodecyl (meth) acrylate, octadecyl (meth) acrylate, eicosyl (meth) acrylate, and docosyl (meth) acrylate.
Examples of the branched alkyl (meth) acrylate having no hydroxyl group include isopropyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, and the like.
Examples of the cycloalkyl (meth) acrylate having no hydroxyl group include cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, cyclopentyl (meth) acrylate, isobornyl (meth) acrylate, and the like.
Examples of the hydroxyl group-containing alkyl (meth) acrylate include hydroxyl group-containing linear alkyl (meth) acrylate, hydroxyl group-containing branched alkyl (meth) acrylate, hydroxyl group-containing cycloalkyl (meth) acrylate, and the like. From the viewpoint of pot life of the primer, etc., a compound having a hydroxyalkyl group with about 1 to 4 carbon atoms is preferable.
Examples of the hydroxyl group-containing linear alkyl (meth) acrylate include hydroxymethyl (meth) acrylate, hydroxyethyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
Examples of the branched alkyl (meth) acrylate containing a hydroxyl group include 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 3-hydroxybutyl (meth) acrylate.
Examples of the hydroxyl group-containing cycloalkyl (meth) acrylate include hydroxycyclohexyl (meth) acrylate, 4- (hydroxymethyl) cyclohexylmethyl (meth) acrylate and the like.
(oligomer poly (meth) acrylate)
Examples of the oligomer poly (meth) acrylate include (poly) pentaerythritol poly (meth) acrylate, (poly) trimethylolpropane poly (meth) acrylate, and hydroxyl-containing glycerol di (meth) acrylate.
((poly) pentaerythritol poly (meth) acrylate)
The (poly) pentaerythritol poly (meth) acrylate is a compound represented by the structural formula (E1).
[ solution 10]
(wherein m is an integer of 0 or more, Rp1～Rp6Each independently is a hydrogen atom or a (meth) acryloyl group, Rp1～Rp6Is a (meth) acryloyl group. Further, Rp3And Rp5There may be different groups for each structural unit. )
In the present disclosure, "(poly) pentaerythritol poly (meth) acrylate" means "at least one selected from the group consisting of pentaerythritol poly (meth) acrylate and polypentaerythritol poly (meth) acrylate".
Further, the phrase "groups which may be different for each structural unit" means that, for example, in the structural formula (E1), when m is 2,
[ solution 11]
Rp3AAnd Rp3BMay be different radicals Rp5AAnd Rp5BMay be different groups (the same applies hereinafter).
Pentaerythritol poly (meth) acrylate includes pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, and the like.
Examples of the polypentaerythritol poly (meth) acrylate include dipentaerythritol di (meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol di (meth) acrylate, tripentaerythritol tri (meth) acrylate, tripentaerythritol tetra (meth) acrylate, tripentaerythritol penta (meth) acrylate, tripentaerythritol hexa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tripentaerythritol octa (meth) acrylate, and the like.
((Poly) trimethylolpropane poly (meth) acrylate)
(Poly) trimethylolpropane poly (meth) acrylate is a compound represented by the structural formula (E2).
[ solution 12]
(wherein p is an integer of 0 or more, Rp7～Rp10Is a hydrogen atom or a (meth) acryloyl group, Rp7～Rp10Is a (meth) acryloyl group. Further, Rp9There may be different groups for each structural unit. )
In the present disclosure, "(poly) trimethylolpropane poly (meth) acrylate" means "at least one selected from the group consisting of trimethylolpropane poly (meth) acrylate and polytrimethylolpropane poly (meth) acrylate".
Examples of the trimethylolpropane poly (meth) acrylate include trimethylolpropane di (meth) acrylate and trimethylolpropane tri (meth) acrylate.
Examples of the poly (trimethylol poly (meth) acrylate include di-trimethylol di (meth) acrylate, di-trimethylol tri (meth) acrylate, and di-trimethylol tetra (meth) acrylate.
(Glycerol (poly) (meth) acrylate)
The glycerin (poly) (meth) acrylate is a compound represented by structural formula (E3).
[ solution 13]
(in the formula, Rp11～Rp13Is a (meth) acryloyl group or a hydrogen atom, Rp11～Rp13Is a (meth) acryloyl group. )
In the present disclosure, "glycerin (poly) (meth) acrylate" means "at least one selected from the group consisting of glycerin poly (meth) acrylate and glycerin (meth) acrylate".
Examples of the glycerin poly (meth) acrylate include glycerin di (meth) acrylate and glycerin tri (meth) acrylate.
The upper limit and the lower limit of the content of the component (E) in 100% by mass of the composition are exemplified by 75% by mass, 70% by mass, 65% by mass, 60% by mass, 55% by mass, 50% by mass, 45% by mass, 40% by mass, 35% by mass, 30% by mass, 25% by mass, 20% by mass, 15% by mass, 10% by mass, 9% by mass, 5% by mass, 3% by mass, 1% by mass, 0.5% by mass, 0.1% by mass, 0% by mass and the like. In one embodiment, the content of the component (E) in 100% by mass of the composition is preferably 0% by mass to 75% by mass.
< photopolymerization initiator (F): also known as component (F) >
In one embodiment, the active energy ray-curable resin composition contains a photopolymerization initiator. Two or more kinds of photopolymerization initiators may be used in combination. Examples of the photopolymerization initiator include 1-hydroxy-cyclohexyl-phenyl ketone, 2-dimethoxy-1, 2-diphenylethan-1-one, 1-cyclohexyl-phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propan-1-one, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropan-1-one, 2,4, 6-trimethylbenzoyl-diphenyl-phosphine oxide, 4-methylbenzophenone, and the like. The photopolymerization initiator is used when ultraviolet curing is performed, but is not necessarily required when electron beam curing is performed.
The upper limit and the lower limit of the content of the component (F) in 100% by mass of the composition are exemplified by 10% by mass, 9% by mass, 5% by mass, 3% by mass, 1% by mass, 0.5% by mass, 0.1% by mass, 0% by mass, and the like. In one embodiment, the content of the component (F) in 100% by mass of the composition is preferably 0% by mass to 10% by mass.
< additives >
The composition may contain, as an additive, an agent that does not correspond to any of the components (a) to (F).
Examples of the additive include a conductive polymer other than the component (A), an amine surfactant other than the component (B), and a non-amine nonionic surfactant, such as a polythiophene vinylene based, a polypyrrole based, a polyfuran based, and a polyaniline based.
In one embodiment, the content of the additive is exemplified by less than 1 part by mass, less than 0.1 part by mass, less than 0.01 part by mass, 0 part by mass, and the like, with respect to 100 parts by mass of the solid content of the composition. Examples thereof include less than 1 part by mass, less than 0.1 part by mass, less than 0.01 part by mass, and 0 part by mass, relative to 100 parts by mass of any of the components (a) to (F).
The composition can be produced by dispersing and mixing the components (a) to (D) and, if necessary, the components (E) to (F) and additives by various known means. The order of addition of the components is not particularly limited. Various known apparatuses (such as an emulsion dispersing machine and an ultrasonic dispersing apparatus) can be used as the dispersing/mixing mechanism.
In one embodiment, the composition is an active energy ray-curable composition. In addition, in one embodiment, the composition may be used as a coating agent, an antistatic coating agent, a conductive coating agent.
[ cured product ]
The present disclosure provides a hardened substance of the composition. In one embodiment, the hardened substance can be obtained by irradiating the composition with active energy rays such as ultraviolet rays, electron beams, and radioactive rays.
The active energy ray for the hardening reaction exemplifies ultraviolet rays or electron beams. As the light source of the ultraviolet ray, an ultraviolet irradiation device having a xenon lamp, a high-pressure mercury lamp, or a metal halide lamp can be used. The amount of light, the arrangement of the light sources, the conveyance speed, and the like may be adjusted as needed, and for example, when a high-pressure mercury lamp is used, it is preferable that the lamp be cured at a conveyance speed of about 5 m/min to 50 m/min with respect to the lamp 1 having a lamp output of about 80W/cm to 160W/cm. On the other hand, in the case of an electron beam, it is preferable to cure the material at a transport speed of about 5 m/min to 50 m/min by an electron beam accelerator having an acceleration voltage of about 10kV to 300 kV.
[ article ]
The present disclosure provides an article including the hardened object.
The article may be manufactured using various known methods. Examples of the method for producing an article include a method in which the composition is applied to at least one surface of a base film (substrate), dried as necessary, and then irradiated with active energy rays. Alternatively, a laminated article may be produced by applying the composition of the present embodiment to the uncoated surface of the obtained base film, laminating another base film thereon, and then irradiating with an active energy ray.
As the base film (substrate), various known base films can be used. Examples of the base film include a polycarbonate film, an acrylic film (e.g., a polymethyl methacrylate film), a polystyrene film, a polyester film, a polyolefin film, an epoxy resin film, a melamine resin film, a triacetyl cellulose film, an acrylonitrile-butadiene-styrene (ABS) film, an acrylonitrile-styrene (AS) film, a norbornene resin film, a cyclic olefin film, and a polyvinyl alcohol film. The thickness of the base film is not particularly limited, but is preferably about 15 μm to 100 μm.
Examples of the coating method include bar coater coating, wire bar coating, meyer bar coating, air knife coating, gravure coating, reverse gravure coating, offset printing, flexographic printing, screen printing, and the like.
The coating amount is not particularly limited, but is preferably 0.1g/m in mass after drying2～30g/m2About, more preferably 1g/m2～20g/m2。
[ examples ]
The present invention will be specifically described below with reference to examples and comparative examples. However, the description of the preferred embodiments and the following examples are provided for illustrative purposes only and are not intended to limit the present invention. Therefore, the scope of the present invention is not limited to the embodiments specifically described in the present specification, nor to the examples, but is limited only by the claims. In each of examples and comparative examples, unless otherwise specified, parts,% and the like are based on mass.
< preparation of component (A) >
Preparation example 1
1000g of a commercially available aqueous dispersion of PEDOT/PSS (trade name, "Ookadan (Orgacon)", having a solid content concentration of 1.2% by weight, was treated with a spray dryer (trade name, "GA-32", manufactured by Daihe scientific Co., Ltd.) (spray pressure 0.6MPa, drying temperature (inlet) 150 ℃ C.) to obtain 9.0g of a blue solid. In addition, the same operation was repeated to prepare a blue solid in an amount necessary for the preparation of the conductive composition.
Example 1
1.20g of the solid component (A) (hereinafter, abbreviated as P/P) obtained in preparation example 1 and 96.4g of ethanol were added to a beaker, and 2.40g of an amine alkylene oxide adduct (trade name: Liponol C/18-18, manufactured by lion specialty-Chemicals) (product name: Cleimer (Clearmix) and M technology (MTechnique) (product name: manufactured by Shiraji corporation)) as a component (B) was added, and then, the mixture was treated at 18000rpm for 10 minutes by using an ultrasonic disperser (19.6kHz, manufactured by silver fountain (Ginsen) (product name: manufactured by Shiraji)) and then, the mixture was treated at an output of 400W for 10 minutes by using the same ultrasonic disperser, thereby obtaining a composition having a solid content of 3.6 wt%. Then, 0.87g of Stearyl Gallate (Stearyl Gallate) as the component (C), 123.89g of ethanol and 40.59g of ethylene glycol as the component (D), and 160.95g of a mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate (product name "Aronix (Aronix) M-400", manufactured by tokyo corporation), and a photopolymerization initiator (product name "Omira (OMNIRAD) 2959", manufactured by IGM Resins b.v. (manufactured by IGM Resins b.v.)) were added to the composition, and the composition was obtained by thoroughly stirring (solid content concentration: about 40 wt%).
Examples and comparative examples other than example 1 were carried out in the same manner as in example 1, except that the components were changed as shown in table 1.
(preparation of film)
Each active energy ray-curable resin composition was applied to a PET film (Lumirror 100U483 manufactured by dongli (stock)) having a film thickness of 100 μm by a bar coater (model No.24, manufactured by first physico-chemical (stock)) so that the film thickness of the cured coating film was 3 μm, and dried for 1 minute by a dryer at 80 ℃. Next, the obtained film was subjected to high pressure mercury vapor deposition using a high pressure mercury lamp 300mJ/cm manufactured by using an ultraviolet ray curing apparatus (product name: UBT-080-7A/BM, MUQIPLY (MULTIPLE)2) A film having a hardened coating film was obtained. The following evaluation results of the produced film are shown in table 1.
< antistatic test >
The surface resistance of the film immediately after the production was measured at an applied voltage of 500V using a commercially available resistivity meter (product name "Hiresta (Hiresta) MCP-HT-450" manufactured by Mitsubishi Chemical analysis technology (Mitsubishi Chemical Analtech) and according to Japanese Industrial Standard (JIS) K6911.
1×1013Ω/sq≧···○
1×1013Ω/sq<···×
< Heat resistance test >
The resulting film was heated with a 170 ℃ dryer for 30 minutes. The surface resistance of the film after the test was measured in the same manner as described above. The film after the test was measured by a transmission method using a colorimeter (trade name: manufactured by ZE 6000 japan electrochromic industries, ltd.), and when the yellow index (YI value) after heating was less than 4, the film was classified as "o", and when the yellow index (YI value) was 4 or more, the film was classified as "x".
[ Table 1]
BHT: 2, 6-di-tert-butyl-p-cresol
Adekastab (Adekastab) AO-60: pentaerythritol tetrakis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ]
Lyte Ester (Light Ester) P-1M: phosphate acrylates
Claims (4)
1. A composition, comprising: a conductive polymer/polyanion complex (a) composed of a polythiophene (a1) and a polymer (a2) containing a sulfo-anion group, wherein the polythiophene (a1) is represented by formula (1); an amine (B) represented by formula (2); a gallic acid ester compound (C) represented by the formula (3); and an organic solvent (D);
in the formula (1), A is alkylene;
in the formula (2), X1Is alkyl, alkenyl orAralkyl radical, Y1And Y2Each independently is a polyoxyalkylene group;
in the formula (3), R represents an alkyl group, an alkenyl group, an aryl group or an aralkyl group.
2. The composition according to claim 1, comprising a compound (E) containing a polymerizable unsaturated carbon bond.
3. A cured product of the composition according to claim 1 or 2.
4. An article comprising the cured product according to claim 3.
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| JP5283818B2 (en) | 2004-10-08 | 2013-09-04 | 信越ポリマー株式会社 | Conductive composition and method for producing the same |
| JP5402777B2 (en) | 2009-03-31 | 2014-01-29 | 荒川化学工業株式会社 | Conductive polymer / dopant dispersion, conductive composition, and conductive film |
| TWI482812B (en) * | 2009-03-31 | 2015-05-01 | Arakawa Chem Ind | Conductive polymer / dopant dispersion, conductive composition, and conductive film |
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| TWI636092B (en) * | 2012-10-23 | 2018-09-21 | 日商荒川化學工業股份有限公司 | Organic solvent dispersion of conductive polymer/polyanion complex, conductive composition including the same and conductive film obtained from the conductive composition |
| JP6614927B2 (en) | 2015-11-06 | 2019-12-04 | 信越ポリマー株式会社 | Capacitor and manufacturing method thereof |
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| CN101035860A (en) * | 2004-10-08 | 2007-09-12 | 信越聚合物株式会社 | Conductive composition and process for producing the same, antistatic paint, antistatic coating and antistatic film, optical filter, optical information recording medium, and capacitor and process for |
| JP2008045116A (en) * | 2006-07-18 | 2008-02-28 | Arakawa Chem Ind Co Ltd | Electroconductive polymer/dopant complex organic solvent dispersion, manufacturing method thereof, and composition containing the electroconductive polymer/dopant complex organic solvent dispersion |
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