TW201516065A - Curable resin composition and coating composition comprising the same - Google Patents

Abstract

The present invention can achieve, with the following curable resin composition, a cured product excellent in hardness, scratch resistance, and adhesion with poly (methyl methacrylate) (PMMA) resin. The curable resin composition contains amine ester (methyl) acrylate which can be obtained in the following manner: making (A1) a polyisocyanate which has more than two isocyanate groups in one molecule, or/and (A2) an amine ester prepolymer which has more than two isocyanate groups in one molecule, react with (B) (methyl) acrylate having one or more hydroxyl groups, and one or more alkylene oxide chains in one molecule.

Description

Curable resin composition and coating composition containing the same

The present invention relates to a curable resin composition and a coating composition containing the same.

Because of its low cost and excellent formability and light weight, plastic materials have been expanding their markets in optical films, automotive components, and building materials. However, compared with inorganic materials such as glass and metal, plastic materials have the disadvantage of poor physical strength such as hardness and scratch resistance. Therefore, in order to eliminate such disadvantages, the following method has been studied: a hard coat film is formed on the surface of a plastic substrate using an ultraviolet curable paint (Patent Document 1). However, the conventional ultraviolet curable composition containing a polyfunctional monomer and an oligomer is excellent in hardness and scratch resistance, but also has poor adhesion to a substrate and is liable to cause peeling.

[Previous Technical Literature] (Patent Literature)

Patent Document 1: Japanese Laid-Open Patent Publication No. 2012-219132

The object of the present invention is to provide an amine ester (meth) acrylate (urethane(meth)acrylate) and a resin composition containing the amine ester (meth) acrylate, the amine ester (meth) acrylate and the resin composition containing the amine ester (meth) acrylate are eliminated In the conventional UV-curable plastic substrate, the hardened material has a defect confirmed, and a cured product having excellent hardness and scratch resistance and polymethylmethacrylate (PMMA) is obtained. The adhesion of the resin is good.

In order to achieve the above object, the first object of the present invention is a curable resin composition containing an amine ester (meth) acrylate obtained by having more than 2 isocyanate groups in (A1)1 molecule. A polyisocyanate or an amine ester prepolymer having more than two isocyanate groups in (A2)1 molecule, and (B) one molecule having one or more hydroxyl groups and one or more alkylene oxide chains (methyl) The acrylate reacts. Further, it is preferable that the curable resin composition is formed into a cured product in which the glass transition temperature measured by dynamic viscoelasticity measurement is 0 ° C or more and 30 ° C or less.

According to a second aspect of the invention, there is provided a coating composition comprising the curable resin composition.

That is, the inventors have repeatedly studied hard to obtain a curable resin composition which can obtain hardness, scratch resistance, and adhesion to polymethyl methacrylate (PMMA) resin. Excellent hardened material. In the course of the present invention, the present inventors have found that the desired object can be attained by the following curable resin composition, that is, the curable resin composition contains an amine ester obtained in the following manner. (Meth) acrylate: polyisocyanate having more than 2 isocyanate groups in (A1)1 molecule An ester, or/and an amine ester prepolymer having more than two isocyanate groups in the (A2) molecule, and (B) a molecule having one or more hydroxyl groups and one or more alkylene oxide chains in one molecule. The acrylate is reacted.

Hereinafter, embodiments of the present invention will be described in detail.

The curable resin composition of the present invention contains an amine ester (meth) acrylate obtained in the following manner: a polyisocyanate having more than 2 isocyanate groups in the molecule (A1), or / and (A2) 1 molecule An amine ester prepolymer having more than two isocyanate groups is reacted with (B) a (meth) acrylate having one or more hydroxyl groups and one or more oxyalkylene chains in one molecule.

The polyisocyanate having more than two isocyanate groups in the above (A1) molecule is not particularly limited, and specific examples thereof include a dimer or a trimer of polyisocyanate (a) or a modified isocyanate such as a biuretized isocyanate. .

The polyisocyanate (a) is not particularly limited, and specific examples thereof include an aliphatic polyisocyanate, an alicyclic polyisocyanate, an aromatic polyisocyanate, and an aromatic aliphatic polyisocyanate.

Examples of the aliphatic polyisocyanate include tetramethylene diisocyanate, dodecamethylene diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, and 2,4. 4-trimethylhexamethylene diisocyanate, quaternary acid diisocyanate, 2-methylpentane-1,5-diisocyanate, 3-methylpentane-1,5-diisocyanate, and the like.

Examples of the alicyclic polyisocyanate include isophorone diisocyanate. Hydrogenated dimethyl diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, 1,4-cyclohexane diisocyanate, methylcyclohexane diisocyanate, 1,3-bis(isocyanatemethyl)cyclohexane Alkane, etc.

Examples of the aromatic polyisocyanate include toluene diisocyanate, 2,2'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, and 4,4'-diphenylmethane diisocyanate (MDI). , 4,4'-dibenzyldiisocyanate, 1,5-naphthalene diisocyanate, benzenedimethyl diisocyanate, 1,3-benzene diisocyanate, 1,4-phenylene diisocyanate, and the like.

Examples of the aromatic aliphatic polyisocyanate include dialkyldiphenylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanate, and α,α,α,α-tetramethylbenzenedimethyl diisocyanate.

The polyisocyanate having more than two isocyanate groups in the above (A1) molecule is preferably a terpolymer of, for example, Hexamethylene diisocyanate (HMDI). These polyisocyanates may be used singly or in combination of two or more kinds.

The amine ester prepolymer having more than two isocyanate groups in the above (A2) molecule can be obtained by making a polyisocyanate having two or more isocyanate groups in one molecule and having more than 2 in one molecule. The hydroxyl group polyol is reacted.

Specific examples of the polyisocyanate having two or more isocyanate groups in one molecule include the above-mentioned polyisocyanates.

The polyol having more than two hydroxyl groups in one molecule is not particularly limited, and specific examples thereof include trimethylolpropane, glycerin, pentaerythritol, di-trimethylolpropane, dipentaerythritol, and oxidation of the polyols. Ethylene modification, oxidation A propylene modified product, a butylene oxide modified product, a caprolactone modified product, a polybutylene glycol modified product, or the like; these polyols may be used singly or in combination. Among them, preferred are trimethylolpropane and glycerin.

The (meth) acrylate having one or more hydroxyl groups and one or more oxyalkylene chains in the above (B) molecule can be obtained by having an alkylene oxide having one or more hydroxyl groups in one molecule ( Methyl) acrylate addition polymerization.

The structure of the (meth) acrylate having one or more hydroxyl groups in the above-mentioned one molecule is not particularly limited as long as it has a hydroxyl group in the molecule, and specific examples thereof include 2-hydroxyethyl acrylate and 2-hydroxy methacrylate. Ethyl ester, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 4-hydroxybutyl acrylate, caprolactone modification - 2-hydroxyethyl acrylate, etc.; The acrylate is used alone or in combination.

Examples of the alkylene oxide-added alkylene oxide having one or more hydroxyl groups in one molecule include ethylene oxide, propylene oxide, butylene oxide, and the like. Examples of the polymerization form include polymerization of various alkylene oxides. The random polymerization and block polymerization are carried out using two or more kinds of alkylene oxides. Among these polymerization forms, in terms of adhesion to polymethyl methacrylate (PMMA) resin, homopolymerization, random polymerization, or block polymerization of propylene oxide and butylene oxide is preferred.

The average addition molar number of the alkylene oxide is preferably 1 mol or more and 10 mol or less per mol of the (meth) acrylate having 1 or more hydroxyl groups per molecule. When the average addition mole amount is less than 1 mol, the adhesion to the polymethyl methacrylate (PMMA) resin is lowered; when it is more than 10 m, the hardness and scratch resistance of the cured product are lowered. Hey.

A well-known method can be used to add a polymeric alkylene oxide to a (meth) acrylate having a hydroxyl group in one molecule.

The amine ester (meth) acrylate of the present invention can be synthesized by a known method. For example, it can be synthesized by one-time input of (A1) or (A2) component and (B) component, in the presence of a polymerization inhibitor such as hydroquinone monomethyl ether, at 70 to 80 ° C. Warm and stir until the free isocyanate disappears. At this time, a tin-based catalyst such as dibutyltin dilaurate may be added to promote the reaction.

(A1) and (A2) may be reacted with the component (B), respectively, or both of (A1) and (A2) may be reacted with the component (B).

Further, when an amine ester prepolymer having more than two isocyanate groups in one molecule of (A2) is used, the amine ester (meth) acrylate of the present invention can be synthesized by one-time injection into one molecule. a polyisocyanate having two or more isocyanate groups, a polyol having more than two hydroxyl groups in one molecule, and a component (B) in the presence of a polymerization inhibitor such as hydroquinone monomethyl ether at 70 to 80 ° C Warm and stir until the free isocyanate disappears. At this time, a tin-based catalyst such as dibutyltin dilaurate may be added to promote the reaction.

The curable resin composition containing the amine ester (meth) acrylate of the present invention preferably has a glass transition temperature of 0 ° C or more and 30 ° C or less as measured by dynamic viscoelasticity measurement. When the glass transition temperature is less than 0 ° C, it is sticky, and when it is more than 30 ° C, it is difficult to have recovery at normal temperature. The glass transition temperature is more preferably 0 ° C or more and 28 ° C or less, and still more preferably 0 ° C or more and 25 ° C or less.

The curable resin composition containing the amine ester (meth) acrylate of the present invention may contain an organic solvent such as ethyl acetate or methyl ethyl ketone or a monomer. More The content of the amine ester (meth) acrylate of the present invention in the curable resin composition is preferably set to 50% by weight or more.

A monomer which is conventionally used can be used as a monomer to be blended. Among them, typical examples of the monomer include 2-ethylhexyl (meth)acrylate, styrene, methyl methacrylate, and acrylonitrile. Porphyrin, tetrahydrofurfuryl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxypropyl (meth)acrylate, benzyl (meth)acrylate, poly(methyl)acrylate Phenyl phenyl ester, poly(ethoxy) ethoxyphenyl acrylate, phenyl benzyl (meth) acrylate, o-phenylphenol (meth) acrylate, o-phenylphenoxy ethoxy (meth) acrylate Ester, poly(ethylene) acrylate o-phenylphenoxy ethoxylate, isodecyl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate , dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, monohydroxyethyl methacrylate (meth) acrylate, ethylene glycol di(meth)acrylic acid Ester, propylene glycol di(meth) acrylate, polyethylene glycol di(meth) acrylate, polypropylene glycol di(meth) acrylate, polybutylene glycol di(meth) acrylate, 1,4-butyl Glycol-di Acrylate, 1,6-hexanediol-di(meth)acrylate, 1,9-nonanediol-di(meth)acrylate, EO (ethylene oxide, the same below) modified bisphenol II (Meth) acrylate, PO (oxypropylene, the same below) modified bisphenol di(meth) acrylate, dimethylol dicyclopentane di (meth) acrylate, neopentyl glycol di (a) Acrylate trimethylolpropane tri(meth)acrylate, EO modified trimethylolpropane tri(meth)acrylate, PO modified trimethylolpropane tri(meth)acrylate, pentaerythritol Tris(meth)acrylate, ((meth)acryloxyethyl)isocyanurate, pentaerythritol tetra(meth)acrylate, EO-modified pentaerythritol tetra(meth)acrylate, PO modification Pentaerythritol tetra(meth)acrylate, di-trimethylol Propane tetra(meth)acrylate, EO modified di-trimethylolpropane tetra(meth)acrylate, PO modified di-trimethylolpropane tetra(meth)acrylate, dipentaerythritol six (a) Acrylate, EO modified dipentaerythritol hexa(meth) acrylate, PO modified dipentaerythritol hexa(meth) acrylate, caprolactone modified dipentaerythritol hexa(meth) acrylate, dipentaerythritol Methyl) acrylate or the like. These monomers may be used singly or in combination of plural kinds.

A polymerization initiator using an active energy ray is added to the curable resin composition of the present invention as needed. Here, the polymerization initiator which utilizes an active energy ray includes both a photopolymerization initiator and a polymerization initiator which uses an active energy ray such as ultraviolet rays.

As the photopolymerization initiator, for example, an aromatic ketone such as diphenyl ketone; an aromatic compound such as ruthenium or α-chloromethylnaphthalene; or a sulfur compound such as diphenyl sulfide or thiourethanecarboxylate can be used.

Examples of the polymerization initiator which utilizes an active energy ray such as ultraviolet light other than visible light include acetophenone, acetophenone benzyl ketal, 1-hydroxycyclohexyl phenyl ketone, and 2,2-dimethoxy group. 1,2-diphenylethane-1-one, xanthone, anthrone, benzaldehyde, anthraquinone, anthracene, triphenylamine, carbazole, 3-methylacetophenone, 4-chlorodi Phenyl ketone, 4,4'-dimethoxydiphenyl ketone, 4,4'-diaminodiphenyl ketone, benzoin propyl ether, benzoin ethyl ether, benzoin dimethyl ketal, 1-( 4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, thioxanthone, two Ethylthioxanthone, 2-isopropylthioxanthone, 2-chlorothioxanthone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinyl-propane-1 -ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinylphenyl)-butanone-1,4-(2-hydroxyethoxy)phenyl-(2-hydroxyl -2-propyl)ketone, 2,4,6- Trimethyl benzhydryl diphenyl phosphine oxide, bis(2,6-dimethoxybenzylidene)-2,4,4-trimethylpentyl phosphine oxide, oligomeric (2-hydroxy- 2-methyl-1-(4-(1-methylvinyl)phenyl)propanone) or the like.

As a commercial product using a polymerization initiator of an active energy ray, for example, a product name: Irgacure 184, Irgacure 369, Irgacure 651, Irgacure 500, manufactured by Ciba Specialty Chemicals Co., Ltd., may be mentioned. Irgacure 819, Irgacure 907, Irgacure 784, Irgacure 2959, Irgacure 1000, Irgacure 1300, Irgacure 1700, Irgacure 1800, Irgacure 1850, Darocur 1116, Darocur 1173; trade name manufactured by BASF: Lucirin TPO; UCB) trade name: Uvecryl P36; trade name manufactured by Fratelli Lamberti: Esacure KIP150, Esacure KIP100F, Esacure KT37, Esacure KT55, Esacure KTO46, Esacure TZT, Esacure KIP75LT; Nippon Kayaku Co., Trade name manufactured by Ltd.): Kayacure DETX, etc.

Further, a radical polymerization initiator may be used in combination with an active energy ray initiator as needed. As the radical polymerization initiator, for example, benzamidine peroxide, methylcyclohexanone peroxide, cumene hydroperoxide, dicumyl peroxide, di-tert-butyl peroxide, and Organic peroxides such as butyl benzoate benzoate, diisopropyl peroxycarbonate, and butyl butyl sulphate; 2,2'- even bisbisisobutyronitrile (AIBN), etc. Azo compound.

The content of the polymerization initiators varies depending on the kind and the like, and the standard is: the polymerization initiator is 1 based on 100 parts by weight of the amine ester acrylate. ~8 parts by weight. When the content of the polymerization initiator is too small, the activity energy ray sensitivity is insufficient, and if it is too large, there is a tendency that the active energy ray does not sufficiently reach the depth of the coating film, and the hardenability in the depth of the coating film is lowered. In addition, the energy source source for curing the curable resin composition of the present invention is not particularly limited, and examples thereof include a high pressure mercury lamp, an electron beam, a gamma ray, a carbon arc lamp, a xenon lamp, and a metal halide lamp.

In addition to the above-mentioned curable resin composition, various additives which are usually included in a coating material, a coating agent and the like may be added to the coating composition of the present invention as needed. Examples of the additives include a light stabilizer, a UV absorber, a catalyst, a leveling agent, an antifoaming agent, a polymerization accelerator, an antioxidant, a flame retardant, an infrared absorber, an antistatic agent, a slip agent, and the like. The coating composition of the present invention can be used as a coating material, a coating agent or the like. The object to be coated or coated (the object to be coated) can be exemplified by electrical and electronic equipment such as a mobile phone, a watch, a compact disc, an audio-visual equipment, an office automation equipment (OA equipment), a touch panel, and a Braun tube. Electronic components such as anti-reflection plates; household appliances such as refrigerators, vacuum cleaners, microwave ovens; automotive interiors such as meter panels and instrument panels; pre-coated steel plates; automobile bodies, bumpers, spoilers, door handles, handles, Headlights, fuel tanks for locomotives, aluminum foils, door mirrors, etc. that have been electroplated, vapor-deposited or sputtered; garage roofs, lighting roofs, protective layers for optical disc recording media, sunglasses or corrective lenses, etc. Protective layers for various optical lenses; woodwork products such as stairs, floors, tables, chairs, wardrobes, and other furniture; cloth, paper, etc.

The coating method may be carried out according to a usual method, and examples thereof include air. Spray method, electrostatic coating method, roll coating method, flow coating method, spin coating method, and the like. The thickness of the film obtained by coating or coating is preferably about 1 to 100 μm. When the thickness of the film is less than 1 μm, it is difficult to exhibit the function as a film. When the film thickness is more than 100 μm, the thickness of the film is too thick, and the physical properties of the object to be coated are hard to be exhibited.

The curable resin composition of the present invention can obtain a cured product which is excellent in hardness, scratch resistance, and adhesion to a polymethyl methacrylate (PMMA) resin.

[Examples]

Next, the examples are explained together with the comparative examples. However, the invention is not limited to the embodiments.

[Synthesis of Amine Ester Acrylate]

(Synthesis Example 1)

An isocyanurate adduct of hexamethylene diisocyanate (HMDI) (manufactured by Nippon Polyurethane Industry Co., Ltd., Coronate HX) 593 g (1 mol), p-benzene Diphenol monomethyl ether 0.9 g, polypropylene glycol monoacrylate (manufactured by NOF Corporation, AP-400) 1089 g (2.6 mol), hydroxypropyl acrylate 91 g (0.7 m), at 70-80 ° C The reaction was carried out until the amount of the free isocyanate became 0.1% or less to obtain the amine ester acrylate A.

(Synthesis Example 2)

Into the flask, 134 g (1 mol) of trimethylolpropane, 336 g of hexamethylene diisocyanate (2.0 mol), 1.5 g of hydroquinone monomethyl ether, and polypropylene glycol monoacrylate (manufactured by Nippon Oil, AP) were charged. -800) 2599g at 70~80°C The reaction was carried out until the amount of free isocyanate became 0.1% or less to obtain an amine ester acrylate B.

(Synthesis Example 3)

To the flask, an isocyanurate adduct of hexamethylene diisocyanate (HMDI) (manufactured by Nippon Polyurethane Co., Ltd., Coronate HX) 593 g (1 mol), hydroquinone monomethyl ether 0.9 g, polybutylene A diol monoacrylate (molecular weight 432) of 1123 g (2.6 mol) and a -4-hydroxybutyl acrylate 101 g (0.7 mol) were reacted at 70 to 80 ° C until the amount of free isocyanate became 0.1% or less to obtain an amine. Ester acrylate C.

(Synthesis Example 4)

To the flask were charged 134 g (1 mol) of trimethylolpropane, 336 g (2.0 mol) of hexamethylene diisocyanate, 1.5 g of hydroquinone monomethyl ether and polytetramethylene glycol monoacrylate (molecular weight 792). 2495 g, the reaction was carried out at 70 to 80 ° C until the amount of free isocyanate became 0.1% or less to obtain an amine ester acrylate D.

(Synthesis Example 5)

A biuret body of hexamethylene diisocyanate (HMDI) (manufactured by Asahi Kasei Chemicals Corporation, 24A-100), 536 g (1 mol), and hydroquinone monomethyl ether 0.9 g were placed in a flask. , polypropylene glycol monoacrylate (manufactured by NOF Corporation, AP-400) 1089g (2.6 moles), hydroxypropyl acrylate 91g (0.7 moles), reacted at 70-80 ° C until the amount of free isocyanate becomes 0.1% or less Thus, the amine ester acrylate E was obtained.

(Synthesis Example 6)

Adding bisphenol A propylene oxide adduct to the flask (Adeka) Corporation), BPX55) 800g (1 mole), hexamethylene diisocyanate 336g (2.0 moles), hydroquinone monomethyl ether 0.7g and 2-hydroxyethyl acrylate 243.6g (2.1 moles) The reaction was carried out at 70 to 80 ° C until the amount of free isocyanate became 0.1% or less to obtain an amine ester acrylate F.

(Synthesis Example 7)

A biuret body of hexamethylene diisocyanate (NCO content 23.5%, average trifunctional) 536 g (1 mol), hydroquinone monomethyl ether 0.8 g, and 2-hydroxyethyl acrylate were added to the flask. The caprolactone 2 molar addition (molecular weight 344) was 1083.6 g (3.15 mol), and the reaction was carried out at 70 to 80 ° C until the amount of free isocyanate became 0.1% or less to obtain an amine ester acrylate G.

[Preparation and evaluation of curable resin composition]

The photopolymerization initiator (Irgacure 184 manufactured by Ciba Specialty Chemicals Co., Ltd.) was separately dispensed and dissolved in 100 parts of each of the amine ester acrylates A to D obtained in the above-mentioned synthesis examples. The obtained solution was applied onto a polymethyl methacrylate (PMMA) substrate (manufactured by Mitsubishi Rayon Co., Ltd., Acrylite) to have a film thickness of about 20 μm, using a high-pressure mercury lamp. 80 W/cm was irradiated with a cumulative illuminance of 200 mJ/cm ² in a nitrogen atmosphere to be hardened. The glass transition temperature, pencil hardness, and adhesion of each of the obtained cured products were examined by the following methods. The results are shown in Table 1 below.

(glass transition temperature)

Regarding the glass transition temperature, a dynamic viscous elastic measuring device (UBM Co., Ltd., model: Rheogel-E4000) was used to measure the loss tangent (tan δ) under the conditions of a tensile sine wave, a frequency of 1 Hz, and a temperature rising rate of 3 ° C/min. The maximum value comes as the glass transfer temperature.

(pencil hardness)

According to Japanese JIS K5400, a pencil scratch tester was used, and a load of 750 g was applied to perform scratching to obtain the hardest pencil hardness without scratches.

(adhesiveness)

According to Japanese JIS K5600-5-6:1999 "Cross-cut method", 100 mesh-shaped slits of 1 mm × 1 mm were cut out on the surface of the coating film, and a peeling test was performed using a tape. The evaluation criteria are also evaluated based on the same criteria.

○: Among the 100 slits, the area that has not been peeled off is 80 or more.

×: In the 100 incisions, the area without unpeeling is less than 80

According to Table 1, it was found that the curable resin composition containing the amine ester (meth) acrylate of the present invention forms a cured product having a pencil hardness of 2H and excellent in polymethyl methacrylate. Adhesion of the ester (PMMA) substrate. According to Comparative Example 1, it was confirmed that a cured product of an amine ester methacrylate having a functional group number of 2 or less was used, and the hardness of the cured product was inferior; according to Comparative Example 2, it was confirmed that the molecule contained no oxyalkylene chain and the molecule was The cured product of the amine ester (meth) acrylate having a hydroxyl group (meth) acrylate component is inferior in adhesion to a polymethyl methacrylate (PMMA) substrate.

Further, it was confirmed that many other than the polyols described in Examples 1 to 5 were used. The amine ester (meth) acrylate of the present invention having a monohydric alcohol, a polyisocyanate, and a (meth) acrylate having one or more hydroxyl groups and one or more oxyalkylene chains in the molecule also has the same pencil hardness as in the examples. , adhesion, and glass transfer temperature.

[Industrial availability]

The curable resin composition containing the amine ester (meth) acrylate of the present invention can obtain a cured product having moderate hardness and excellent adhesion to a polymethyl methacrylate (PMMA) substrate. It is suitable for use as a coating or coating agent in the field where hardness is required. Specifically, it can be applied to the following objects: mobile phones, watches, optical discs, audio-visual equipment, OA equipment and other electrical and electronic equipment; electronic components such as touch panels; home appliances such as refrigerators, vacuum cleaners, microwave ovens, flat-panel televisions; , car panels and other automotive interiors; automotive parts.

The present invention has been described in detail above with reference to the specific embodiments thereof. It will be understood by those of ordinary skill in the art that various changes or modifications can be made without departing from the spirit and scope of the invention.

The present application is based on Japanese Patent Application No. 2013-198149, filed on Sep. 25, 2013, the content of which is hereby incorporated by reference.

Claims (3)

A curable resin composition characterized by containing an amine ester (meth) acrylate obtained by a polyisocyanate having more than 2 isocyanate groups in (A1)1 molecule, or / and (A2)1 An amine ester prepolymer having more than two isocyanate groups in the molecule is reacted with (B) a (meth) acrylate having one or more hydroxyl groups and one or more oxyalkylene chains in one molecule. The curable resin composition according to claim 1, wherein the curable resin composition forms a cured product having a glass transition temperature of 0 ° C or more and 30 ° C or less as measured by dynamic viscoelasticity measurement. . A coating composition comprising the curable resin composition according to claim 1 or 2.