JPH10237356A - Active energy ray-hardenable coating composition and hardening of the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition capable of providing a coated membrane having high abrasion resistance without damaging recoatability and printability, and useful as a coating material for a can, especially the coating material for a beverage can by formulating polyolefin resin particles having a specific melting point to a monomer-diluting type coating material in a specified proportion. SOLUTION: The objective composition comprises (A) 1-20wt.% polyolefin resin particles having 100-300 deg.C melting point (e.g. high density or low density polyethylene or polypropylene having average particle diameter of 30-300% of the coating thickness in the dried state), (B) 10-70wt.% monomer [e.g. styrenes, vinyl ethers, vinyl compounds, monofunctional or polyfunctional (meth) acrylates or an epoxy-containing compound] and (C) 10-89wt.% other resins (e.g. an epoxy resin or an phenol resin having 30-300 deg.C glass transition temperature and 1,000-50,000 weight average molecular weight).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to an active energy ray-curable coating composition.

[0002]

2. Description of the Related Art Currently used paints can be classified into solvent type, aqueous type and monomer dilution type according to the type of solvent used. Solvent-type paints use organic solvents,
It can dissolve high molecular weight polymers and is now widely used. On the other hand, there are problems such as the necessity of treating air pollution and coating liquid as dangerous substances. The aqueous paint can be applied without using an organic solvent, but requires a large amount of heat to evaporate water as a dispersion medium.
The monomer-diluted coating does not have the above-mentioned problems because it does not use an organic solvent and water, and has rapid curing properties, and is therefore expected to be promising in the future.

However, a coating film obtained by applying a monomer-diluted type, that is, an active energy ray-curable coating material, has poor rub resistance, and is easily scratched when rubbed after curing. Provided a performance far inferior to the solvent type and the aqueous type. In particular, the above problem is very important when the coated product is carried on a belt conveyor on a production line. That is, in the case of the conventional active energy ray-curable paint, the coatings immediately after curing on the belt conveyor, or the friction between the coating and the conveyor guide, easily scratched,
It was difficult to obtain a high-quality coating film on a general production line.

[0004] In order to impart lubricity to a coating film and prevent scratches, attempts have conventionally been made to incorporate paraffin wax, vegetable oil, or the like. However, when paraffin wax or the like is added, the paraffin is localized on the surface of the coating film, so that it is known that an attempt to apply or print on the cured coating film has an adverse effect. Was. Further, as disclosed in Japanese Examined Patent Publication No. 60-17463, attempts have been made to add polyethylene resin particles to a solvent-type paint in order to prevent the coating film surface from being damaged. However, in the case of the solvent-type paint, since the coating film is cured by baking treatment, the heat dissolves the polyethylene resin particles. As a result, deterioration of the coating film performance was observed during overcoating and the like.

[0005]

DISCLOSURE OF THE INVENTION The present invention does not require a special exhaust gas treatment facility such as a solvent-type paint, and provides a quick-curing, high-productivity, and strong film. It is an object of the present invention to provide a revolutionary coating composition which has high abrasion resistance and does not impair recoatability and printability, and a method for curing the same.

[0006]

Means for Solving the Problems The present inventors have added polyolefin resin particles having a specific melting point range to a specific ratio in a monomer-diluted paint which could not be used because of a problem with the friction resistance immediately after curing. It has been found that, by blending with the above, high friction resistance can be imparted to the coating film, and the coating film does not impair the recoatability or printability, and the present invention has been accomplished. Since the monomer-diluted paint does not require heating when curing the coating film, the coating film can be cured at a temperature lower than the melting point of the polyolefin resin particles. The resin particles exist while maintaining the particle shape. The polyolefin resin particles present in the cured coating film impart high abrasion resistance to the coating film, but do not impair recoatability or printability.

That is, the present invention has a melting point of 100 to 300 ° C.
1-20% by weight of polyolefin resin particles (A), monomer
The present invention relates to an active energy ray-curable coating composition comprising (B) 10 to 70% by weight and another resin (C) 10 to 89% by weight. The present invention also relates to the active energy ray-curable coating composition, wherein the other resin (C) has a glass transition temperature of 30 to 300 ° C. Also,
The present invention relates to the above active energy ray-curable coating composition, which is used as a coating composition for cans. The present invention also relates to the above active energy ray-curable coating composition, wherein the average particle size of the polyolefin resin particles (A) is 30 to 300% of the coating thickness.

[0008] The present invention also relates to the active energy ray-curable coating composition, wherein the active energy ray is ultraviolet light. Further, the present invention relates to the active energy ray-curable coating composition, wherein the active energy ray is an electron beam. Further, the present invention provides the above-mentioned active energy ray-curable coating composition at a temperature of 0 ° C or higher and 100 ° C or higher.
And a method for curing a coating composition, characterized in that the coating composition is cured in an atmosphere of less than

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION Polyolefin resin particles (A)
It is used to achieve both the abrasion resistance of the coating film and the recoating and printability. Examples of the polyolefin resin include high-density polyethylene, low-density polyethylene, and polypropylene. Polyolefin resin particles (A)
Has a melting point in the range from 100 to 300 ° C, preferably from 110 to 200 ° C. The melting point in the present invention is the peak point of the heat of fusion measured using a differential scanning calorimeter. Polyolefin resin particles having the above melting point range do not dissolve or melt in the uncured paint, and do not dissolve or melt even when cured by active energy rays.
The coating containing the particles does not cause deterioration in performance due to dissolution or melting of the particles.

The content of the polyolefin resin particles (A) is
1 to 20% by weight, preferably 2 to 20% by weight based on the total weight of the paint
10% by weight. Even if the content of the particles (A) is smaller or larger than the above range, it is difficult to achieve both abrasion resistance and suitability for recoating and printing. Polyolefin resin particles (A)
The preferred particle size of the particles (A) depends on the coating thickness when the coating is applied, and the preferred average particle size of the particles (A) is 30 to 300%, more preferably 50 to 200%, most preferably 50 to 200% of the coating thickness when dried. Preferably it is 70% to 150%. For example, when the coating thickness during drying is
In the case of 10 microns, polyolefin resin particles (A) having an average particle size of 3.0 to 30 microns, which is 30 to 300% of that, are preferably used.

The preferred average particle size of the polyolefin resin particles (A) is preferably 3 to 50 microns, more preferably 4 to 30 microns in consideration of the general coating thickness of the coating. If the average particle size of the polyolefin resin particles (A) is too large or too small, the effect of improving the friction resistance is reduced. If smaller,
If the particles settle in the coating and are too large,
It becomes difficult to keep the particles on the coating.

The polyolefin resin particles (A) may contain inorganic components such as silica gel, mica and carbon black, carnauba wax in the range of 40% by weight or less for the purpose of adjusting the melting point, adjusting the specific gravity, and changing the properties of the particles. And other resin components such as polytetrafluoroethylene and polyvinylidene fluoride. Examples of the method for mixing the additives include dry mixing, melt mixing, and the like. Considering the curability and lubricity of a paint, it is most preferable to melt mix polytetrafluoroethylene.

The monomer (B) is roughly classified into a radical reaction type monomer and a cation reaction type monomer. The radical reactive monomer is not particularly limited as long as it is a compound having a reactive unsaturated double bond, and styrenes, vinyl ethers, vinyl compounds, monofunctional (meth) acrylates,
And polyfunctional (meth) acrylates. Examples of the styrenes include styrene and methylstyrene. Examples of vinyl ethers include ethyl vinyl ether, propyl vinyl ether, and hydroxyethyl vinyl ether. Examples of the vinyl compounds include triallyl isocyanurate, trialmethallyl isocyanurate, and N-vinylpyrrolidone.

The monofunctional (meth) acrylates include:
Methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, lauryl (meth)
Acrylate, polyethylene glycol (meth) acrylate, polyethylene glycol (meth) acrylate methyl ether, phenylethyl (meth) acrylate, isobornyl (meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate , Methoxytripropylene glycol (meth) acrylate, phenoxy polyethylene glycol (meth) acrylate, dimethylaminoethyl (meth) acrylate,
(Meth) acryloylmorpholine, isobornyl (meth) acrylate, (meth) acrylamide and the like can be mentioned.

The polyfunctional (meth) acrylates include:
Butanediol di (meth) acrylate, hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, nonanediol di (meth) acrylate, glycol di (meth) acrylate, diethylene di (meth) acrylate, polyethylene glycol di ( (Meth) acrylate, trisacryloyloxyethyl isocyanurate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, adipic acid epoxy (meth) acrylate, hydrogenated bisphenol ethylene oxide Di (meth) acrylate, ethylene glycol glycerol tri (meth) acrylate, trimethylolpropane tri (meth) acryle Triethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, ethylene glycolated pentaerythritol tri (meth) acrylate, Examples include propylene glycolated pentaerythritol tri (meth) acrylate and dipentaerythritol tri (meth) acrylate.

The cation-reactive monomer is not particularly limited as long as it is a compound generally having an epoxy group. For example, glycidyl (meth) acrylate, methyl glycidyl ether, ethyl glycidyl ether, butyl glycidyl ether, bisphenol A diglycidyl ether, 3,4-epoxycyclohexylmethyl-3,4, -epoxycyclohexanecarboxylate (manufactured by Union Carbide Co., Ltd.) "Siracure UVR-6110", 3,4-epoxycyclohexylethyl-3,4-epoxycyclohexanecarboxylate, vinylcyclohexene dioxide ("ELR-4206" manufactured by Union Carbide), limonene dioxide (Daicel Chemical) "Ceroxide 30" manufactured by Kogyo
00 ”), allylcyclohexene dioxide, 3,4, -epoxy-4-methylcyclohexyl-2-propylene oxide, 2- (3,4-epoxycyclohexyl-5,5-spiro-3,4
-Epoxy) cyclohexane-m-dioxane, bis (3,
4-epoxycyclohexyl) adipate (Union Carbide's “Siracure UVR-6128” etc.), bis (3,
4-epoxycyclohexylmethyl) adipate, bis (3,4-epoxycyclohexyl) ether, bis (3,4-
Epoxycyclohexylmethyl) ether, bis (3,4-
(Epoxycyclohexyl) diethylsiloxane and the like.

The content of the monomer (B) is from 10 to 70% by weight, preferably from 20 to 60% by weight, based on the total weight of the coating composition.
If the content of the monomer (B) is less than the above range, the viscosity is high and coating becomes difficult, and if it is too large, the strength of the cured coating film is reduced.
Other resins (C) are those that dissolve in the paint and have a glass transition temperature (Tg) of 30 to 300 ° C.
Resins in the range of -250 ° C are preferred. Glass-transition temperature
A resin having a (Tg) of less than 30 ° C. is difficult to obtain a strong film, and a resin having a temperature of more than 300 ° C. is not preferable because processability is deteriorated. Weight average molecular weight of resin (C) is 1,000 or more5
It is preferably not more than 0,000. When the molecular weight is low, the curability of the paint is low, and when the molecular weight is high, the viscosity of the paint becomes high and coating is difficult.

The content of the resin (C) is 10 to 89% by weight, preferably 15 to 50% by weight, based on the total weight of the coating composition. If the content is less than the above range, the curability of the cured coating film will be deteriorated, and if it is too large, the viscosity of the coating will increase, making the coating difficult. As the resin (C), for example,
Bisphenol type epoxy resin, novolak type epoxy resin, phenol resin, urethane resin, ester resin,
Resins such as ketone formaldehyde resin, cresol resin, novolak resin, xylene resin, diallyl phthalate resin, styrene resin, guanamine resin, natural rubber, synthetic rubber, acrylic resin, other polyolefin resins, and modified products thereof.

The coating composition of the present invention may contain, if necessary,
Reactive oligomers, pigments, initiators, dispersants such as surfactants, lubricants, leveling agents such as silicon, surface modifiers, and the like can be added. In addition, in consideration of viscosity, coating suitability, etc., a solvent can be added in a range of up to 5% by weight based on the total amount of the paint for fine adjustment. Reactive oligomers include radically reactive oligomers and cationically reactive oligomers. Examples of the radical reactive oligomer include ester acrylate, epoxy acrylate, and ester acrylate. Examples of the cation-reactive oligomer include general-purpose epoxy oligomers such as bisphenol type, novolak type epoxy oligomer, aliphatic epoxy oligomer, alicyclic epoxy oligomer, epoxidized animal and vegetable oils, and epoxidized polybutadiene.

The pigment is not particularly limited and includes, for example, phthalocyanine, azo, quinacridone, lake, and the like.
Benzimidazolone, anthraquinone, dioxazine, indigo, thioindigo, perylene, perinone, diketopyrrolopyrrole, anthrone, isoindolinone, nitro, nitroso, anthraquinone, flavanthrone And organic pigments such as quinophthalone, pyranthrone and indanthrone, and inorganic pigments such as titanium oxide, carbon black, red iron oxide, zinc oxide, indium, ITO and barium sulfate.

The initiator is added when the coating composition of the present invention is used as a radical reaction paint or a cationic reaction paint which is cured by ultraviolet rays. In the case where the coating composition of the present invention is used as a radical reaction type coating composition cured by an electron beam, no initiator is required. Initiators are mainly classified into radical reaction initiators and cation reaction initiators. For example, examples of the radical initiator include a monocarbonyl compound, a dicarbonyl compound, an acetophenone compound, a benzoin ether compound, an acylphosphine oxide compound, and an aminocarbonyl compound.

Examples of the monocarbonyl compound include benzophenone (Kayacure BP100 manufactured by Nippon Kayaku Co., Ltd.), 4-methyl-benzophenone (Photocure 81 manufactured by Sunko) and the like.
2,4,6-trimethylbenzophenone (Fratelli Lamberti Epacure TZT / TMBZ, etc.), methyl-o-benzoylbenzoate (Shibel Hegner, Daitocure OB / Wako Pure Chemicals, PS-96, etc.), 4-phenylbenzophenone ( AKZO
4 (4-methylphenylthio) phenyl-enetanone (IBIS Quantacure BMS, etc.)
, 3,3'-dimethyl-4-methoxybenzophenone (Kayacure BMP manufactured by Nippon Kayaku Co., Ltd.), 4- (1,3-acryloyl
-1,4,7,10,13-pentaoxotridecyl) benzophenone (such as Uvecryl P36 manufactured by Union Carbide), 3,3'4,4'-
Tetra (t-butylperoxycarbonyl) benzophenone (BTTB manufactured by NOF Corporation), 4-benzoyl-NNN-trimethylbenzenemethammonium chloride (IBIS manufactured
(Quantacure BTC / Nippon Kayaku Kayacure BTC etc.)
, 2-hydroxy-3- (4-benzoyl-phenoxy) -NNN-
Trimethyl-1-propanamine hydrochloride (IBIS Quant
acure BPQ), 4-benzoyl-NN-dimethyl-N- [2- (1
-Oxo-2-propenyloxyethyl] metaammonium bromate (Kayacure ABQ manufactured by Nippon Kayaku Co., Ltd.), 2- / 4-i
so-propylthioxanthone (Nippon Kayaku Kayacure
ITX / Lamberti Esacure ITX, etc.), 2,4-diethylthioxanthone (Nippon Kayaku KayacureDETX, etc.),
2,4-dichlorothioxanthone (Kayacure manufactured by Nippon Kayaku Co., Ltd.
CTX, etc.), 1-chloro-4-propoxythioxanthone (
Kayacure CPTX manufactured by Nippon Kayaku Co., Ltd.), 2-hydroxy-3-
(3,4-Dimethyl-9-oxo-9H thioxanthone-2-yloxy) -N, N, N-trimethyl-1-propanamine hydrochloride (such as Nippon Kayaku Kayacure QTX), benzoylmethylene
-3-methylnaphtho (1,2-d) thiazoline and the like.

Examples of the dicarbonyl compound include 1,7,7-trimethyl-bicyclo [2,1,1] heptane-2,3-dione, benzyl (Seikol BZ manufactured by Seiko Chemical Co., Ltd./S123 manufactured by Shinko Giken Co., Ltd.), 2-ethylanthraquinone, 9,10-phenanthrenequinone (Hans Rohn PION, etc.), methyl
-α-oxobenzene acetate (Stauffer-AKZO Vi
cure 55 / Rahn Nuvopol PI3000 etc.), 4-phenylbenzyl (AKZO Trigonal P121 etc.) and the like.

As the acetophenone compound, 2-hydroxy-2-methyl-1-phenylpropan-1-one (Ciba Ge
igy Darocure 1173), 1- (4-isopropylphenyl) 2-hydroxy-2-methyl-1-phenylpropane
-1-on (Ciba Geigy / Merck Darocure 1116 etc.)
, 1- (4-isopropylphenyl) 2-hydroxy-di-2-
Methyl-1-phenylpropan-1-one (such as Irgacure 2959 manufactured by Ciba Geigy), 1-hydroxy-cyclohexyl-phenyl ketone (such as Irgacure184 manufactured by Ciba Geigy), 2-hydroxy-2-methyl-1-styrylpropane- 1
-On-polymer (e.g., Fraselli Lambert Esacure KIP), diethoxyacetophenone (Upjohn DEAP /
First Chemical's FIRST DEAP etc.), dibutoxyacetophenone (Upjohn's Uvatone 8301 etc.), 2,2-
Dimethoxy-1,2-diphenylethan-1-one (Ciba Geig
y Irgacure 651 / ShibelHegner Esacure KBI
2,2-diethoxy-1,2-diphenylethan-1-one (such as Uvatone 8302 manufactured by Upjohn), 2-methyl-1- [4-
(Methylthio) phenyl] -2-morpholinopropan-1-one (such as Irgacure 907 manufactured by Ciba Geigy), 2-benzyl
2-dimethylamino-1- (4-morpholino-phenyl) butan-1-one (such as Irgacure 369 manufactured by Ciba Geigy), 1-
Phenyl-1,2-propanedione-2- (o-ethoxycarbonyl) oxime (such as Quantacure PDO manufactured by IBIS), 3,6-
Bis (2-methyl-2-morpholino-propanonyl) -9-butylcarbazole (eg, Florcure A3 manufactured by Floridienne) and the like.

Examples of the benzoin ether compound include benzoin (Esacure BO manufactured by Fratelli Lamberti / BENZOIN B manufactured by Wako Pure Chemical / Seikol Z manufactured by Seiko Chemical Co., Ltd.),
Benzoin methyl ether (Shinko Giken S121, etc.), benzoin ethyl ether (Seiko Chemical Seikeol BEE / Wako Pure Chemicals PS-8A / Daito Mix Mix Daitocure EE / ShibelHegner Daitocure
EE), benzoin isopropyl ether (Sinko Giken S12 / Seiko Chemical Seikaru BIP / Wako Pure Chemicals PS-10A / AKZO Vicure 30 / ShibelHegne
r Daitocure IP, etc.), benzoin isobutyl ether (S124, manufactured by Shinko Giken Co., Ltd./ Seikol BBI, manufactured by Seiko Chemical Co., Ltd./ PS-11, manufactured by Wako Pure Chemical Co., Ltd./ Vicure, manufactured by AKZO
10 / ShitoHegner Daitocure IB / Fratelli Lam
berti Esacure EBZ), benzoin normal butyl ether (Fratelli Lamberti Esacure EB1 / EB3
/ EB4).

As acylphosphine oxide compounds, 2,4,6-trimethylbenzoyldiphenylphosphine oxide (such as Lucirin TPO manufactured by BASF), 4-n-propylphenyl-di (2,6-dichlorobenzoyl) phosphine oxide ( BAPO manufactured by Ciba Geigy / PO 0003 manufactured by ESPE).

As the aminocarbonyl compound, methyl
-4- (Dimethylamino) benzoate (DAITOKURE DAA / PAA, etc., manufactured by Daito Chemix), ethyl-4- (dimethylamino) benzoate (Esacure, manufactured by ShibelHegner)
EDB / Nippon Kayaku Kayacure EPA / IBIS Quantac
ure EPD / Lamberti Firstcure EDAB / Lambson Speedcure EDB, etc.), 2-n butoxyethyl-4- (dimethylamino) benzoate (IBIS Quantacure EBA
/ Lambson Speedcure BEDB etc.), Isoamyl-4
-(Dimethylamino) benzoate (Kayac manufactured by Nippon Kayaku Co., Ltd.)
ure DMBI / VanDyk Escolol 506), 2- (dimethylamino) ethyl benzoate (IBIS Quantacure
DMB / Nippon Kayaku Kayacure MCA / Octel Chemicals
Kayacure MCA etc.), 4,4'-bis-4-dimethylaminobenzophenone (Shinko Giken S111 etc.)
, 4,4'-bis-4-diethylaminobenzophenone (S112 manufactured by Shinko Giken Co., Ltd./EAB manufactured by Hodogaya Chemical Co., Ltd.),
2,5′-bis- (4-diethylaminobenzal) cyclopentanone (S113 manufactured by Shinko Giken Co., Ltd.) and the like.

Examples of the cationic initiator include diazonium salts of Lewis acids, iodonium salts of Lewis acids, sulfonium salts of Lewis acids, phosphonium salts of Lewis acids, other halides, triazine initiators, and borate initiators. And other photoacid generators.

The diazonium salts of Lewis acids include p-methoxyphenyldiazonium fluorophosphonate, N, N-
Diethylaminophenyldiazonium hexafluorophosphonate (SAN-AID SI-60L / SI-80 manufactured by Sanshin Chemical Industry Co., Ltd.)
L / SI-100L) .Examples of the Lewis acid iodonium salt include diphenyliodonium hexafluorophosphonate and diphenyliodonium hexafluoroantimonate.Examples of the Lewis acid sulfonium salt include triphenylsulfonium hexafluorophosphate. Phosphonates (such as Union Carbide's Cyracure UVI-6990)
And triphenylsulfonium hexafluoroantimonate (eg, Cyracure UVI-6974 manufactured by Union Carbide), and the phosphonium salts of Lewis acids include triphenylphosphonium hexafluoroantimonate.

Other halides include 2,2,2-trichloro- [1-4 '-(dimethylethyl) phenyl] ethanone
(E.g., Trigonal PI manufactured by AKZO), 2.2-dichloro-1-4- (phenoxyphenyl) ethanone (Sandoz 100, Sandoz 100)
0, etc.), α, α, α-tribromomethylphenylsulfone (eg, BMPS manufactured by Iron and Steel Chemical Co., Ltd.) and the like. Examples of triazine-based initiators include 2,4,6-tris (trichloromethyl) -triazine, 2,4-trichloromethyl- (4'-methoxyphenyl) -6-triazine (e.g., Triazine A manufactured by Panchim), 2, 4-trichloromethyl- (4'-methoxystyryl)-
6-triazine (Panchim Triazine PMS etc.), 2,4-triazine
Trichloromethyl- (pipronyl) -6-triazine (Panchim
Triazine PP, etc.), 2,4-trichloromethyl- (4'-
(Methoxynaphthyl) -6-triazine (Panchim Triazin
e B), 2 [2 '(5 "-methylfuryl) ethylidene] -4,6-
Bis (trichloromethyl) -s-triazine (manufactured by Sanwa Chemical Co., Ltd.), 2 (2'-furylethylidene) -4,6-bis (trichloromethyl) -s-triazine (manufactured by Sanwa Chemical Co., Ltd.), etc. Can be

Examples of the baud rate-based initiator include NK-3876 and NK-3881 manufactured by Nippon Kosaku Dye, and other photoacid generators such as 9-phenylacridine and 2,2′-bis
(o-chlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2-
Biimidazole (such as Biimidazole manufactured by Kurokin Kasei),
2,2-azobis (2-amino-propane) dihydrochloride
(Such as V50 manufactured by Wako Pure Chemical Industries, Ltd.), 2,2-azobis [2- (imidasolin-2yl) propane] dihydrochloride (such as VA044 manufactured by Wako Pure Chemical Industries, Ltd.), [eta-5-2-4- (cyclopentane Decyl) (1,2,3,4,5,6, eta)-(methylethyl) -benzene
Iron (II) hexafluorophosphonate (Ciba Geigy Irg
acure 261), bis (y5-cyclopentadienyl) bis [2,6-difluoro-3- (1H-pyrid-1-yl) phenyl]
Titanium (CGI-784 manufactured by Ciba Geigy) and the like.

In addition, azo-based initiators such as azobisisobutyronitrile and peroxide-based radical initiators such as benzoyl peroxide may be used in combination. In addition, both a radical initiator and a cationic initiator may be used in combination. One type of initiator can be used alone, or two or more types can be used in combination.

The method for producing the coating composition of the present invention is not particularly limited, and examples thereof include a shaking disperser, a sand mill,
It can be manufactured using a dispersing machine such as a ball mill, a disper, a homogenizer, a three-roll, a two-roll, and a kneader. It is also possible to adjust the particle size of the polyolefin resin particles using the above disperser. The coating composition of the present invention has a viscosity at 25 ° C of 100 to 300,00.
It is preferable to adjust to 0 cps, more preferably 200 to 5,000 cps. Paint with a viscosity at 25 ° C of less than 100 cps is difficult to form a strong film, and 300,000 cps
Coatings with more than are difficult to apply.

The substrate on which the coating composition of the present invention can be applied is not particularly limited, and examples thereof include aluminum, steel plate, tin-free steel (TFS) plate, tinplate,
Metal plate such as polyethylene terephthalate (PET) film laminated steel plate, resin plate and film such as polyethylene, polypropylene, acrylic, PET, polycarbonate, polyamide, polyimide, etc., polyethylene coated paper,
Papers such as coated paper such as PET-coated paper and uncoated paper are exemplified.

The coating of the coating composition of the present invention can be performed by, for example, an offset printing machine, a gravure printing machine, a screen printing machine,
The printing is performed using a printing machine such as a flexographic printing machine or a coating machine such as a roll coater, a curtain coater, a knife coater, or a spray. The use of the coating composition of the present invention is not particularly limited,
It is suitably used as a material requiring friction resistance after coating and curing, for example, a paint for food containers such as beverage cans, food cans, beverage and food paper packs, a paint for precoated steel sheet, and a paint for processed paper. Above all, it is suitably used as a paint for cans such as beverage cans, food cans, and cosmetic cans that require high friction resistance, and particularly a paint for beverage cans.

The coating site can be used for an outer surface base coat, a top clear coat, an inner surface coat, a can lid coat and the like. In particular, in view of abrasion resistance, recoatability and printability, the outer surface base coat can be used. Also, it is suitably used for a top clear coat due to its friction resistance.

The material of the can includes aluminum can, steel can, tin can, resin film laminated can and the like, and is not particularly limited. When applied to a resin film laminated can, particularly a polyethylene terephthalate resin film laminated can, The high friction resistance, which is a characteristic of the coating composition of the present invention, can be maximized. There are no particular restrictions on the type of cans, including two-piece cans and three-piece cans. Particularly, in the case of two-piece cans, they are applied after being processed into a cylindrical shape and immediately after the curing process of the paint. Since it flows over, the effect of the present invention can be maximized.

For curing the coating composition of the present invention, an active energy ray is used. Examples of the active energy ray include ultraviolet rays, visible light rays, electron beams, electromagnetic waves, and radiation.In particular, since ultraviolet rays and electron rays can be cured in a short time without raising the temperature in the atmosphere, and at low cost, particularly, preferable. As a curing mechanism of the coating composition of the present invention,
There are a radical reaction type, a cation reaction type, and a type having both of the reaction types, but the coating composition of the present invention shows good characteristics in any of the curing mechanisms.

The ultraviolet light is not particularly limited, but has a wavelength of 150 to
Ultraviolet light in the range of 600 nm is preferably used. When cured by ultraviolet light in the above wavelength range, the effects of the present invention can be maximized, and a coating film having high friction resistance can be obtained. The electron beam is not particularly limited, but the accelerating voltage is 30 to 500 KV.
Particularly, an electron beam of 30 to 100 KV is preferably used. When cured by an electron beam having an acceleration voltage of 30 to 100 KV, the effects of the present invention can be maximized, and a coating film having high friction resistance can be obtained. The preferred dose of the electron beam is about 5 KGy to 200 KGy, more preferably 10 KGy to 100 KGy. If the irradiation dose is too low, curing is insufficient, and if it is too high, the abrasion resistance of the coating film is impaired.

The temperature for curing the coating composition of the present invention is preferably from 0 ° C. to less than 100 ° C., more preferably from room temperature to 80 ° C. In the present invention, the curing temperature indicates the ambient temperature in the curing device. Curing temperature is 0 ℃
In order to make it less than, a cooling device must be installed,
Not practical. On the other hand, if the curing temperature exceeds 100 ° C,
Since the polyolefin resin particles are melted by heat, the effect of improving the friction resistance of the coating film is reduced.

[0041]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to the examples. The viscosity was measured using a rheometer (“RFS-II” manufactured by Rheometrics) at 25 ° C. and a steady flow viscosity at 100 S-1. As for the melting point (mp), the peak of heat of fusion was measured using a differential scanning calorimeter (DSC, "DSC 2000" manufactured by TA Instruments).

The abbreviations in the examples are shown below. S363 SHAMROCK PP / PE particles (mp = 142 ° C, particle size 5 microns) S232 SHAMROCK PE particles (mp = 113 ° C, particle size 5 microns) S394N1 SHAMROCK PE particles (mp = 113 ° C, particle size 5 microns) S399N2 SHAMROCK PE particles (mp = 124 ° C, 7 micron particle size) FS511 SHAMROCK PE / PTFE particles (mp = 126 ° C, 6 micron particle size, containing 7% by weight of PTFE) FS421 SHAMROCK PE / PTFE particles (mp = 126 ° C, 6 micron particle size, 13% by weight PTFE, FS722 SHAMROCK PE / PTFE particles (mp = 115 ° C, 5 micron particle size, 14% by weight PTFE) NS5521 SHAMROCK, PP particles (mp = 155 ° C, 6 micron particle size) S390C SHAMROCK PE particles (mp = 95 ° C, 6 micron particle size) FS231 SHAMROCK PE / PTFE particles (mp = 68 ° C, 6 micron particle size, PTFE13 weight%) S490 SHAMROCK PE particles (mp = 87 ° C particle) (5 micron diameter)

M9050 Ester acrylate (reactive oligomer) manufactured by Toagosei Co., Ltd. AER6004 Epoxy resin manufactured by Asahi Ciba Geigy (Tg 95 ° C., MW = 3,000) UVR-6110 Epoxy monomer manufactured by Union Carbide COX3000 Epoxy monomer manufactured by Daicel Chemical Industries Body Celoxide 3000 UVR-6990 Union Carbide Cationic Initiator Irgacure 184 Ciba Geigy Radical Initiator AER6004 Asahi Ciba Geigy Epoxy Resin (Tg 95 ° C, MW = 3,000) S-101 Mitsubishi Gas Chemical Xylene Resin ( Tg 110 ° C, MW = 4,000) CP50S Acrylic / styrene copolymer resin manufactured by NOF Corporation (Tg 120 ° C, MW = 8,000) BGR Benzoguanamine resin manufactured by Nippon Shokubai Co., Ltd. (Tg 70 ° C, MW = 3,000) HP30 manufactured by Mitsubishi Gas Chemical Company Novolak resin (Tg 150 ° C, MW = 7,000 GRL Phenolic resin manufactured by Mitsubishi Gas Chemical Company (Tg 200 ° C, MW = 4,000) 110H Ketone formaldehyde resin manufactured by Honshu Chemical Company (Tg 8 5 ℃, MW = 2,000) EP1004 Yuka Shell Epoxy epoxy resin (Tg 100 ℃, MW = 3,000) IBXAHP Isobornyl acrylate homopolymer (Tg 95 ℃, MW = 8,000) LR-155 Mitsubishi Rayon acrylic resin (Tg -20 ° C, MW = 7,000) EHA hydroxyethyl acrylate

Example 1 and Comparative Example 1 (Radical Reaction Type White Paint for Laminating Can) The polyolefin resin (PO) particles shown in Table 1 were used in the amounts shown in Table 1 in the reactive oligomer (M905).
0) 10 g, phenylethyl acrylate 20 g, titanium oxide 2
0 g and 10 g of an epoxy resin (AER6004) were blended and kneaded to obtain an outer base paint for a PET laminated can. The viscosity of the obtained paint was measured. In addition, the obtained paint is applied to PET laminated steel sheet for beverage cans using a bar coater,
It was cured with an electron beam irradiation of 80 KV / 50 KGy. The internal atmosphere temperature of the conveyor section in the curing device was 30 ° C. After curing, the average film thickness was measured by an eddy current type film thickness meter, and the pencil hardness of the coating film was measured according to JIS K5400, paragraph 6.14.

In addition, as a friction resistance test, two cured coating plates were wound around a 350 ml can within one minute after curing, held in both hands, shifted at an angle of 90 degrees, and pressed with approximately 5 kg of force. Pressed and rubbed 10 times. The degree of damage at that time was evaluated according to the following criteria. 1: All of the coating film on the friction surface was peeled off. 2: 50% or more and less than 100% of the coating film on the friction surface was peeled off. 3: 1% or more and less than 50% of the coating on the friction surface peeled off. (Practical limit level) 4: Streaky scratches were observed on the coating film on the friction surface. 5: No change in the coating on the friction surface. In addition, as a recoating test, apply an oil-based clear paint on the cured coating plate and dry in an oven at 180 ° C for 80 seconds.
Pencil hardness was measured by the above method. Table 1 shows the results.

Table 1 PO particle addition amount Viscosity Hardness Scratch Film thickness Top hardness Example 1-1 S363 3.0g 1020cps 2H 4.3 5μ 2H Example 1-2 S232 3.0g 980cps H 4.0 5μ 3H Example 1-3 S394N1 3.0g 870cps 2H 4.0 5μ 3H Example 1-4 S399N2 3.0g 780cps 2H 4.3 5μ 3H Example 1-5 FS511 3.0g 940cps 3H 4.7 5μ 3H Example 1-6 FS421 3.0g 910cps 3H 5.0 5μ 3H Example 1-7 FS722 3.0g 1230cps 2H 5.0 5μ 3H Example 1-8 NS5521 2.5g 1160cps H 4.7 5μ 3H Example 1-9 FS421 3.0g 910cps H 3.3 1.5μ F Example 1-10 FS421 3.0g 910cps 4H 3.7 2μ 3H Example 1 -11 FS421 3.0g 910cps 3H 4.3 3.5μ 3H Example 1-12 FS421 3.0g 910cps 3H 5.0 7μ 3H Example 1-13 FS421 3.0g 910cps 2H 4.3 11μ 3H Example 1-14 FS421 3.0g 910cps 2H 3.7 15μ 3H Example 1-15 FS421 3.0g 910cps HB 3.0 20μH Example 1-16 FS421 1.0g 730cps H 3.7 5μ 3H Example 1-17 FS421 2.0g 780cps 2H 4.3 5μ 3H Example 1-18 FS421 5.0g 1160cps 3H 5.0 5μ 3H Example 1-19 FS421 9.0g 1310cps H 5.0 5μ 3H Example 1-20 FS421 13g 2200cps H 4.3 5μ 3H Comparative Example 1-1 --- 0g 610cps HB 1.0 5μ 2H Comparative Example 1-2 S390C 3.0g 770cps H 2.7 5μ B Comparative Example 1-3 FS231 3.0g 730cps H 3.7 5μ 5B Comparative Example 1-4 S490 3.0g 680cps H 2.7 5μ 3B

Example 2 and Comparative Example 2 (Cation-Reactive White Paint for Laminating Can) The polyolefin resin (PO) particles shown in Table 2 were used in the amount shown in Table 2 and the epoxy monomer (UVR-611) was used.
0) 20g, epoxy monomer (COX3000) 10g, titanium oxide 1
5 g, initiator (UVI-6990) 5 g, and epoxy resin (AER600
4) 10 g was blended and kneaded to obtain an outer base paint for PET laminated cans. The viscosity of the obtained paint was measured. The obtained paint was applied to a PET laminated steel sheet for beverage cans using a bar coater. Using a conveyor-type ultraviolet irradiation apparatus equipped with an ultra-high pressure mercury lamp having an intensity of 120 W / cm 2, curing was performed by irradiation with ultraviolet light at a conveyor speed of 120 m / min. The internal atmosphere temperature of the conveyor section in the curing device is
40-60 ° C. After curing, the average film thickness was measured with an eddy current type film thickness meter, and the pencil hardness of the coating film was further measured according to JIS K5400.
Measured according to 6.14. Further, a friction resistance test was performed in the same manner as in Example 1. Furthermore, as a recoating test,
An aqueous clear paint was applied on the cured coated plate, dried in an oven at 200 ° C. for 100 seconds, and the pencil hardness was measured by the above method. Table 2 shows the results.

Table 2 PO particle addition amount Viscosity Hardness Scratch Film thickness Top hardness Example 2-1 S363 3.0g 960cps 2H 4.0 5μ 2H Example 2-2 S232 3.0g 940cps H 4.0 5μ 3H Example 2-3 S394N1 3.0g 880cps 2H 3.7 5μ 3H Example 2-4 S399N2 3.0g 790cps 2H 4.0 5μ 3H Example 2-5 FS511 3.0g 980cps 3H 4.3 5μ 3H Example 2-6 FS421 3.0g 950cps 3H 4.7 5μ 3H Example 2-7 FS722 3.0g 1180cps 2H 4.7 5μ 3H Example 2-8 NS5521 2.5g 1050cps H 4.3 5μ 3H Example 2-9 FS421 3.0g 910cps H 3.0 1.5μ F Example 2-10 FS421 3.0g 980cps 4H 3.3 2μ 3H Example 2 -11 FS421 3.0g 980cps 3H 4.3 3.5μ 3H Example 2-12 FS421 3.0g 980cps 3H 5.0 7μ 3H Example 2-13 FS421 3.0g 980cps 2H 4.0 11μ 3H Example 2-14 FS421 3.0g 980cps 2H 3.3 15μ 3H Example 2-15 FS421 3.0g 910cps HB 3.0 20μH Example 2-16 FS421 1.0g 690cps H 3.7 5μ 3H Example 2-17 FS421 2.0g 680cps 2H 4.3 5μ 3H Example 2-18 FS421 5.0g 1060cps 3H 5.0 5μ 3H Example 2-19 FS421 9.0g 1180cps H 4.7 5μ 3H Example 2-20 FS421 13g 2300cps H 4.3 5μ 3H Comparative Example 2-1 --- 0g 580cps HB 1.0 5μ 2H Comparative Example 2-2 S390C 3.0g 750cps H 1.7 5μ B Comparative Example 2-3 FS231 3.0g 770cps H 2.7 5μ 5B Comparative Example 2-4 S490 3.0g 690cps H 2.7 5μ 3B

Example 3 and Comparative Example 3 (Radical Reaction Type White Paint for Laminating Can) The amount of the polyolefin resin (PO) particles shown in Table 3 shown in Table 3 in the reactive oligomer (M905)
0) 10 g, phenylethyl acrylate 20 g, titanium oxide 20 g, epoxy resin (AER6004) 10 g, and initiator (Irgacure 184) 3 g were blended and kneaded to obtain an outer base paint for PET laminated cans. The viscosity of the obtained paint was measured. The obtained paint was applied to a PET laminated steel sheet for beverage cans using a bar coater. In addition, 120W / cm
Using a conveyor-type ultraviolet irradiation device equipped with an ultra-high pressure mercury lamp having a high strength, ultraviolet irradiation was performed at a conveyor speed of 120 m / min. The internal atmosphere temperature of the conveyor section in the curing device was 40 to 60 ° C. After curing, the average film thickness was measured by an eddy current type film thickness meter, and the pencil hardness of the coating film was measured according to JIS K5400, paragraph 6.14. Further, a friction resistance test was performed in the same manner as in Example 1. Further, a recoating test was performed in the same manner as in Example 2. Table 3 shows the results
Shown in

Table 3 PO particle addition amount Viscosity Hardness Scratch Film thickness Top hardness Example 3-1 S363 3.0g 1030cps 2H 4.3 5μ 2H Example 3-2 S232 3.0g 990cps H 4.0 5μ 3H Example 3-3 S394N1 3.0g 890cps 2H 4.0 5μ 3H Example 3-4 S399N2 3.0g 800cps 2H 4.3 5μ 3H Example 3-5 FS511 3.0g 960cps 3H 4.7 5μ 3H Example 3-6 FS421 3.0g 940cps 2H 4.7 5μ 3H Example 3-7 FS722 3.0g 1250cps H 5.0 5μ 3H Example 3-8 NS5521 2.5g 1210cps H 4.7 5μ 3H Example 3-9 FS421 3.0g 930cps H 3.3 1.5μ H Example 3-10 FS421 3.0g 930cps 3H 3.7 2μ 3H Example 3 -11 FS421 3.0g 930cps 3H 4.0 3.5μ 3H Example 3-12 FS421 3.0g 930cps 2H 5.0 7μ 3H Example 3-13 FS421 3.0g 930cps 2H 4.3 11μ 3H Example 3-14 FS421 3.0g 930cps 2H 3.3 15μ 3H Comparative Example 3-15 FS421 3.0g 930cps HB 3.0 20μH Example 3-16 FS421 1.0g 750cps H 3.3 5μ 3H Example 3-17 FS421 2.0g 750cps 2H 4.3 5μ 3H Example 3-18 FS421 5.0g 1180cps 2H 5.0 5μ 3H Example 3-19 FS421 9.0g 1320cps H 5.0 5μ 3H Example 3-20 FS421 13g 2230cps H 4.3 5μ 3H Comparative Example 3-1 --- 0g 640cps HB 1.0 5μ 2H Comparative Example 3-2 S390C 3.0g 780cps H 2.7 5μ B Comparative Example 3-3 FS231 3.0g 750cps H 3.7 5μ 5B Comparative Example 3-4 S490 3.0g 640cps H 2.7 5μ 3B

Example 4 and Comparative Example 4 (Radical reaction type white paint for aluminum can) The polyolefin particle resin (PO) shown in Table 4 was used in the amount shown in Table 4 in a reactive oligomer (M9050) 10.
g, EHA20g, titanium oxide 20g, and epoxy resin (AER
6004) 10 g were blended and kneaded to obtain an outer base paint for aluminum cans. The viscosity of the obtained paint was measured. Further, the obtained paint was applied to an aluminum plate for a beverage can using a bar coater, and was cured at an electron beam irradiation amount of 80 KV / 50 KGy. The internal atmosphere temperature of the conveyor section in the curing device was 30 ° C.
After curing, measure the average film thickness with an eddy current type film thickness measuring device,
Further, the pencil hardness of the coating film was measured according to JIS K5400, paragraph 6.14. Further, a friction resistance test and a recoating test were performed in the same manner as in Example 1. Table 4 shows the results.

Table 4 PO particle addition amount Viscosity Hardness Scratch Film thickness Top hardness Example 4-1 S363 3.0g 960cps 3H 4.3 5μ 2H Example 4-2 S232 3.0g 940cps 2H 4.0 5μ 3H Example 4-3 S394N1 3.0g 880cps 2H 3.7 5μ 3H Example 4-4 S399N2 3.0g 790cps 3H 4.3 5μ 3H Example 4-5 FS511 3.0g 980cps 4H 4.3 5μ 3H Example 4-6 FS421 3.0g 950cps 4H 4.7 5μ 3H Example 4-7 FS722 3.0g 1180cps 2H 4.7 5μ 3H Example 4-8 NS5521 2.5g 1050cps H 4.3 5μ 3H Example 4-9 FS421 3.0g 910cps F 3.0 1.5μ H Example 4-10 FS421 3.0g 980cps 4H 3.3 2μ 3H Example 4 -11 FS421 3.0g 980cps 3H 4.3 3.5μ 3H Example 4-12 FS421 3.0g 980cps 3H 5.0 7μ 3H Example 4-13 FS421 3.0g 980cps 2H 4.0 11μ 3H Example 4-14 FS421 3.0g 980cps 2H 3.3 15μ 3H Example 4-15 FS421 3.0g 910cps HB 3.0 20μH Example 4-16 FS421 1.0g 690cps H 3.7 5μ 3H Example 4-17 FS421 2.0g 680cps 2H 4.3 5μ 3H Example 4-18 FS421 5.0g 1060cps 3H 5.0 5μ 3H Example 4-19 FS421 9.0g 1180cps H 4.7 5μ 3H Example 4-20 FS421 13g 2300cps H 4.3 5μ 3H Comparative Example 4-1 --- 0g 580cps HB 1.0 5μ 2H Comparative Example 4-2 S390C 3.0g 750cps H 1.7 5μ B Comparative Example 4-3 FS231 3.0g 770cps H 2.7 5μ 5B Comparative Example 4-4 S490 3.0g 690cps F 2.7 5μ 3B

Example 5 (Consideration of Resin Contained) 3 g of polyolefin resin particles (FS421), reactive oligomer (M9050)
10g, phenylethyl acrylate 20g, titanium oxide 20
g and the resins shown in Table 5 were mixed and kneaded in the amounts shown in Table 5 to obtain a paint for a laminated can. The viscosity of the obtained paint was measured. The obtained paint was applied to a PET laminated steel sheet for beverage cans using a bar coater so that the film thickness when dried was 5 microns. Thereafter, the coating was cured with an electron beam irradiation of 50 KV / 50 KGy, and the coating film was measured for pencil hardness and subjected to a friction resistance test in the same manner as in Example 1. Table 5 shows the results.

Table 5 Resin compounding amount Viscosity Hardness Scratched Example 5-1 AER6004 5g 820cps 2H 5.0 Example 5-2 AER6004 10g 1600cps 3H 4.7 Example 5-3 AER6004 20g 4800cps HB 5.0 Example 5-4 AER6004 30g 10500cps HB 5.0 Example 5-5 S-101 10g 730cps H 4.3 Example 5-6 CP50S 10g 2100cps F 5.0 Example 5-7 BGR 10g 8600cps H 4.3 Example 5-8 HP30 10g 2500cps 2H 5.0 Example 5-9 GRL 15g 2800cps 2H 4.7 Example 5-10 110H 10g 3300cps 2H 5.0 Example 5-11 EP1004 10g 3800cps 2H 5.0 Example 5-12 EP1004 15g 9700cps 2H 4.7 Example 5-13 IBXAHP 15g 6700cps 2H 4.7 Example 5-14 LR- 155 20g 2500cps 3B 3.0

Example 6 (Difference in cured coating film due to electron beam accelerating voltage) The same paint as in Examples 1-1 to 1-8 was dried in the same manner as in Example 1 to obtain a film thickness of 5 After coating to a micron size, the coating was cured with an electron beam irradiation of 200 KV / 50 kgy, and the same evaluation as in Example 1 was performed. Table 6 shows the results. Table 6 Addition amount of PO particles Hardness Scratch Top hardness Example 6-1 S363 3.0g H4.0 2H Example 6-2 S232 3.0g H4.0 3H Example 6-3 S394N1 3.0g 2H 4.0 3H Example 6-4 S399N2 3.0 g 2H 4.3 3H Example 6-5 FS511 3.0g 2H 4.7 3H Example 6-6 FS421 3.0g 3H 4.7 3H Example 6-7 FS722 3.0g 2H 5.0 3H Example 6-8 NS5521 2.5g H 4.3 3H

Comparative Example 7 (Difference in Cured Coating Film Due to Thermosetting) To the same coating material as in Examples 1-1 to 1-8, 5 g of benzoyl peroxide was added to prepare a thermosetting coating material. The obtained coating material was applied in the same manner as in Example 1 so that the film thickness when dried became 5 μm, and then cured with an infrared curing device at a curing temperature of 200 ° C. for 120 seconds. Was evaluated. Table 7 shows the results.

Table 7 PO particle addition amount Hardness Scratch Top hardness Comparative Example 7-1 S363 3.0g H 4.0 4B Comparative Example 7-2 S232 3.0g H 3.7 3B Comparative Example 7-3 S394N1 3.0g 2H 3.3 5B Comparative Example 7- 4 S399N2 3.0g 2H 3.3 4B Comparative Example 7-5 FS511 3.0g 2H 2.7 2B Comparative Example 7-6 FS421 3.0g 3H 2.3 5B Comparative Example 7-7 FS722 3.0g 2H 2.0 3B Comparative Example 7-8 NS5521 2.5g H 4.3 3B

[0058]

According to the present invention, it is possible to provide a paint having high friction resistance immediately after curing, while being a monomer-diluted type which is substantially solvent-free. The coating composition of the present invention is cured by an active energy ray having a curing temperature of less than 100 ° C., and when used as a coating composition for cans, the effect of improving the friction resistance can be maximized.

 ────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Masahiro Ihara 2-3-13-1 Kyobashi, Chuo-ku, Tokyo Toyo Ink Manufacturing Co., Ltd.

Claims (7)

[Claims] (1) 1-20% by weight of polyolefin resin particles (A) having a melting point of 100-300 ° C., 10-70% by weight of monomer (B), and 10-89% by weight of other resin (C). An active energy ray-curable coating composition characterized by comprising: 2. The glass transition temperature of the other resin (C) is from 30 to 30.
The active energy ray-curable coating composition according to claim 1, wherein the temperature is 300 ° C. 3. The active energy ray-curable coating composition according to claim 1, which is used as a coating for cans. 4. The active energy ray-curable coating composition according to claim 1, wherein the average particle size of the polyolefin resin particles (A) is 30 to 300% of the coating thickness. Stuff. 5. The active energy ray-curable coating composition according to claim 1, wherein the active energy ray is an ultraviolet ray. 6. The active energy ray-curable coating composition according to claim 1, wherein the active energy ray is an electron beam. 7. A method for curing a coating composition, comprising curing the active energy ray-curable coating composition according to any one of claims 1 to 6 in an atmosphere of 0 ° C. or more and less than 100 ° C. .