JP3189275B2 - Active energy ray-curable resin composition - Google Patents

Description

The present invention relates to a novel and useful active energy ray-curable resin composition, which has surface curability, surface damage, odor,
It is an object of the present invention to provide an extremely useful active energy ray-curable resin in which properties such as surface lubricity and chemical resistance are remarkably improved.

More specifically, the present invention relates to a novel active energy ray-curable resin composition comprising a compound having a specific structural unit in a molecule as an essential film-forming component.

[Conventional technology]

In recent years, this type of active energy ray-curable resin has been widely used, especially for various surface treatment agents such as for paints.

Compared with the conventional curing method, it is capable of significantly faster curability, non-heat curing and solvent-free, saving line space, and having high energy efficiency required for curing. This is because it has many advantages.

As such active energy ray-curable resin,
A resin system containing an α, β-ethylenically unsaturated double bond is used, such as polyester (meth) acrylate, unsaturated polyester, polyether (meth) acrylate, or polyurethane (meth) acrylate. Further, a photoinitiator, a photosensitizer, or the like may be added to these resin systems, and the resin system may be cured by irradiating light such as ultraviolet light.

However, the conventional active energy ray-curable resin has a disadvantage that its surface curability is poor due to polymerization inhibition particularly by oxygen in the air.

In other words, the fact is that the surface of the cured resin has poor scratching properties and the surface has a tacky feeling, which causes a problem when used.

For this purpose, a method of adding a large amount of a photoinitiator or curing under an atmosphere of an inert gas such as nitrogen has been adopted.

However, if a large amount of photoinitiator is added,
The amount of unreacted photoinitiator increases, and the molecular growth in the photoradical reaction is less likely to be performed.
The adverse effect that performance such as solvent resistance and mechanical properties of the cured coating film is deteriorated is caused.

In addition, a special apparatus is required to perform curing in an atmosphere of an inert gas such as nitrogen, and such a method itself cannot be said to be a general-purpose means.

Further, the addition of a photoinitiator or a photosensitizer to a resin has a disadvantage that an odor is generated after curing.

[Problems to be solved by the invention]

As described above, as long as the conventional technology is followed, it is found that there is no odor, the curability is excellent, the surface damage is improved, and the solvent resistance is also excellent. The fact is that they do not.

In view of the above-mentioned problems in the prior art, the present inventors have been able to significantly improve, in particular, properties such as surface curability, surface damage, odor, surface slippage, and chemical resistance. In order to find an extremely useful active energy ray-curable resin, we have started research.

Accordingly, the problem to be solved by the present invention is, on the one hand, an extremely useful activity which can remarkably improve properties such as surface curability, surface damage, odor, surface lubrication and chemical resistance. It is to provide an energy ray-curable resin.

[Means for solving the problem]

Therefore, the present inventors have made intensive studies in accordance with the standard of the problem to be solved by the invention as described above, and as a result, have found that the active energy ray-curable resin composition having many excellent features as described above. Thus, the present invention has been completed.

That is, the present invention provides, as essential components, a siloxane skeleton and the following structural formula [II], respectively. Or a compound having a group capable of generating a radical by light represented by the general formula [I
A group generating a radical by light represented by I], α,
or a compound having a β-ethylenically unsaturated double bond or a siloxane skeleton and a compound represented by the general formula [I
A) and α, β
The use of an active energy ray-curable resin composition comprising a compound having both an ethylenically unsaturated double bond and a urethane bond, that is to say, more generally, a siloxane skeleton and a general formula [II When an active energy ray-curable resin composition containing a compound having a group that generates a radical by light represented by the following formula as an essential film-forming component is used, the curing of the active energy ray causes surface curability and surface curing. The present invention has been completed by finding that properties such as scratch resistance, odor, surface activity and chemical resistance can be significantly improved.

Here, as the siloxane skeleton described above, for example, a general formula Therefore, in order to introduce such a siloxane skeleton into a molecule, the siloxane skeleton and a part thereof have a reactive functional group directly bonded to a silicon atom (Si). Is used.

Particularly desirable as R and R 'in the above-mentioned formula [I] are monovalent organic groups such as an alkyl group or an allyl group. Usually, a methyl group, an ethyl group or a phenyl group is suitable. is there.

Further, the reactive functional group referred to herein is, for example, a compound represented by the general formula CH _{2 m} OH, CH _{2 m} OCH _{2 n} OH, CH _{2 m} NH ₂ ,
_{2 m} NHCH _{2 n} Such reactive functional groups are pendantly bonded as terminal sites or side chains in the siloxane skeleton. (Hereinafter, these are also referred to as reactive functional group-containing siloxanes.) In order to introduce the above-mentioned group generating a radical by light into a molecule, a method described in JP-A-63-254105 is used. Although a co-reactive photopolymerization initiator can be used, among the compounds having a group that generates a radical by such light, the present invention is represented by a general formula such as `` Darocur 2959 '' manufactured by Merck, West Germany. 4- (2-hydroxyethoxy) -phenyl-2 represented by [II]
-(2-hydroxy) propyl ketone is used.

Further, by introducing a functional group having an α, β-ethylenically unsaturated double bond into the resin (A), it is possible to further improve the curability and physical properties of the coating film. is there.

Typical examples of the compound having such a functional group include α, β-ethylenically unsaturated compounds having various reactive functional groups such as a carboxyl group, a hydroxyl group, an isocyanate group, or an epoxy group at the terminal. .

Among them, as the carboxyl group-containing α, β-ethylenically unsaturated compound, (meth) acrylic acid is the best example, but (meth) acrylic acid and ε-caprolactone ring-opened product and hydroxyl group-containing (meth) Acrylates and acid anhydrides, for example, ring-opened products such as succinic anhydride, phthalic anhydride, trimellitic anhydride or pyromellitic anhydride can also be mentioned.

Hydroxyl-containing α, β-ethylenically unsaturated compound [hereinafter also referred to as hydroxyl-containing (meth) acrylate] ] Can be used, and known ones can be used. Typical examples thereof include 2-hydroxyethyl (meth) acrylate,
-Hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate , Pentaerythritol tri (meta)
Acrylate or glycidyl methacrylate- (meth) acrylic acid adduct;

Α, β-ethylenically unsaturated compound containing isocyanate group [hereinafter also referred to as (meth) acrylate containing isocyanate group. ], "Carenz MOI" [Showa Denko Co., Ltd.]
2-methacryloyloxyethyl isocyanate], or an isocyanate-containing urethane (meth) acrylate obtained by reacting a hydroxyl group-containing (meth) acrylate and a polyisocyanate compound as described above.

The reaction of glycidyl (meth) acrylate or carboxyl group-containing (meth) acrylate with a polyglycidyl compound is not particularly limited to the typical examples of the α, β-ethylenically unsaturated compound containing an epoxy group. Can be mentioned.

The compound having both a siloxane skeleton and a group that generates a radical by light can be obtained, for example, by directly or indirectly reacting a reactive functional group-containing siloxane as described above and a reactive photoinitiator. it can.

This reaction includes a reaction between a hydroxyl group and an isocyanate group,
Reaction between hydroxyl group and carboxyl group, reaction between isocyanate group and amino group, reaction between isocyanate group and carboxyl group, reaction between epoxy group and amine, reaction between epoxy group and carboxyl group, reaction between epoxy group and thiol group There are various types such as a reaction or a reaction between a hydroxyl group and a silanol group.

Similarly, a (meth) acrylate compound having a reactive functional group can also be introduced into the resin (A) by the various reactions described above.

These various types of reactions may, of course, be carried out singly or in a complex form, and are not subject to any restrictions as long as the desired compound is obtained.

Further, it is possible to impart mechanical properties, particularly toughness, of the cured coating film by the urethanization reaction.

The urethane-forming reaction referred to herein means a polycondensation reaction between a hydroxyl group and an isocyanate group, and includes a hydroxyl-containing siloxane compound, a hydroxyl-containing photopolymerization initiator compound and / or a hydroxyl-containing (meth) acrylate compound or an isocyanate group. By reacting the containing (meth) acrylate compound or the like with a polyisocyanate compound or another hydroxyl group-containing compound (polyol), an intended urethane bond-containing compound can be obtained.

As the polyisocyanate compound used in the present invention,
Known ones can be used, but typical examples are 2,4
-Tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,3-xylylene diisocyanate, 1,4-xylylene diisocyanate, diphenylmethane-4,4 '
Diisocyanate compounds having an aromatic ring such as diisocyanate, 3-methyl-diphenylmethane diisocyanate or 1,5-naphthalenediisocyanate; alicyclic diisocyanate compounds such as dicyclohexylmethane diisocyanate or isophorone diisocyanate; or fats such as hexamethylene diisocyanate or lysine diisocyanate Group diisocyanate compound; or an isocyanate compound obtained by hydrogenating the above-mentioned diisocyanate compound having an aromatic ring: for example, hydrogenated xylylene diisocyanate or hydrogenated diphenylmethane-4,4'-diisocyanate; each diisocyanate compound and water And a bullet-type polyisocyanate compound obtained by reacting the compound with 2-isocyanatoethyl-2,6-diyl Trifunctional isocyanate compounds such as cyanate hexanoate; or diisocyanate compound, supra, and the like multimer obtained allowed isocyanuration.

As the above-mentioned other hydroxyl group-containing compounds (polyols), known and commonly used ones can be used. Among them, ethylene glycol and 1,3-propylene glycol may be used if only typical ones are mentioned. , 1,2-propylene glycol, diethylene glycol, dipropylene glycol, neopentyl glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, 1,9-nonanediol, 1,10- Decanediol, 2,
2,4-trimethyl-1,3-pentanediol, 3-methyl-1,5-pentanediol, dichloroneopentyl glycol, dibromoneopentyl glycol, neopentyl glycol hydroxypivalate, cyclohexane dimethylol, 1,4- Cyclohexanediol,
Trimethylolethane, trimethylolpropane, glycerin, 3-methylpentane-1,3,5-triol, pentaerythritol, spiroglycol, tricyclodecanedimethylol or hydrogenated bisphenol A, or "Newcol PM-8701L, BA- E4, BA-EP or BA-PG] [Nippon Emulsifier Co., Ltd., Bisphenol A
Ethylene oxide or propylene oxide adduct] or "carbodiol" (carbonate diol manufactured by Toa Gosei Chemical Industry Co., Ltd.).

Further, there are polyester polyols obtained by an esterification reaction of these various polyols with various commonly used carboxylic acids or acid anhydrides as shown below.

Particularly representative of such carboxylic acids or their anhydrides are maleic acid, fumaric acid, itaconic acid, citraconic acid, tetrahydrophthalic acid, hetonic acid,
Hymic acid, chlorendic acid, dimer acid, adipic acid, succinic acid, alkenyl succinic acid, sebacic acid,
Azelaic acid, 2,2,4-trimethyladipic acid, terephthalic acid, 2-sodium sulfoterephthalic acid, 2-potassium sulfoterephthalic acid, isophthalic acid, 5-sodium sulfoisophthalic acid, 5-potassium sulfoisophthalic acid, 5-sodium Di-lower alkyl sulfoisophthalates (e.g., -dimethyl or -diethyl, etc.),
Orthophthalic acid, 4-sulfophthalic acid, 1,10-decamethylenedicarboxylic acid, muconic acid, oxalic acid, malonic acid, glutanic acid, trimellitic acid, hexahydrophthalic acid, tetrabromophthalic acid, methylcyclohexentricarboxylic acid or pyromellitic Acids and acid anhydrides thereof are exemplified.

The active energy ray-curable resin composition of the present invention contains the above compound as an essential component in an amount of 5 to 80% by weight. If the content of this compound is less than 5% by weight, the number of radical-generating groups in the system will be small, and curing will be slow. If it exceeds 80% by weight, there is a disadvantage that the cured coating film becomes brittle because the cohesive force of the siloxane bond is small.

In the present invention, even more workability, storage stability, for the purpose of modifying the appearance of the cured product and various physical properties,
The addition of other ingredients is not subject to any restrictions.

Other components in this form include reactive diluents, reactive oligomers and polymers, solvents, photo (polymerization) initiators, polymers, polymerization inhibitors, antioxidants, dispersants, surfactants, inorganic fillers, An inorganic pigment, an organic pigment, or the like can be added.

As the above-mentioned reactive diluents, reactive oligomers and polymers, monofunctional ones to polyfunctional ones are widely used. Among them, only typical ones are exemplified. For example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, N-vinylpyrrolidone, 1-vinylimidazole,
Isobornyl (meth) acrylate, tetrahydrofurphyryl (meth) acrylate, carbitol (meth)
Acrylate, phenoxyethyl (meth) acrylate, dicyclopentadiene (meth) acrylate, 1,3
-Butane di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, polyethylene glycol di (meth) acrylate, hydroxypivalic acid ester neopentyl glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate pentaerythritol Tri (meth) acrylate, pentaerythritol tetra (meth) acrylate or dipentaerythritol hexa (meth) acrylate; and further, urethane (meth) acrylate, epoxy (meth) acrylate, polyester (meth) acrylate, polyether ( (Meth) acrylate and the like can be used without being restricted by the molecular weight or the number of (meth) acrylate functional groups.

In addition, if only typical solvents are exemplified, aromatic hydrocarbons such as toluene or xylene; ketones such as methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; methyl acetate, ethyl acetate or butyl acetate Esters such as;
Alcohols such as methanol, ethanol, propanol or butanol; aliphatic hydrocarbons such as hexane or heptane, cellosolve acetate, carbitol acetate, dimethylformamide,
Or tetrahydrofuran.

Furthermore, a photo (polymerization) initiator may be used in combination within the range not accompanied by improvement of unpleasant odor, which is one of the objects of the present invention, when curing an organic material using ultraviolet rays as active energy rays. .

Known and commonly used photo (polymerization) initiators include:
Any of them can be used, and among them, particularly representative ones are acetophenones, benzophenone, Michler's ketone, benzyl and benzoin.
Benzoate, benzoin, benzoin methyl ethers, benzyl dimethyl ketal, α-acyloxime esters, thioxanthones, anthraquinones, and various derivatives thereof.

Furthermore, known and commonly used (photo) sensitizers can be used in combination, but particularly typical examples of such (photo) sensitizers include amines, ureas, sulfur-containing compounds, phosphorus-containing compounds, Examples include chlorine-containing compounds or nitriles or other nitrogen-containing compounds.

As the polymer, a saturated or unsaturated polymer can be used. Among them, acrylic resin, polyester resin, polyamide resin, epoxy resin, polyurethane resin and vinyl chloride-vinyl acetate are particularly typical. Polymerized tree, polyvinyl butyral resin, cellulose resin, chlorinated polypropylene and the like can be mentioned.

Typical inorganic fillers include barium sulfate,
Pigments such as calcium carbonate, talc, mica, clay, barium carbonate, gypsum, alumina white, silica, calcium silicate, magnesium carbonate, silica powder, colloidal silica, asbestos powder, aluminum hydroxide, zinc stearate; graphite, zinc Chromates such as chromate or molybdate orange, ferrocyanides such as navy blue, titanium oxide, zinc oxide, red iron oxide, metal oxides such as chromium carbide green, metal sulfides such as cadmium yellow, cadmium red or mercury sulfide. Or sulfates such as selenide or lead sulfate, silicates such as ultramarine, or carbonates,
Phosphates such as bio red or manganese purple; or metal powders such as aluminum powder, zinc powder, brass powder, magnesium powder, iron powder, copper powder or nickel powder;
Inorganic pigments such as carbon black; or azo pigments;
Organic pigments such as copper phthalocyanine pigments such as phthalocyanine blue and phthalocyanine green or quinacridone pigments.

The energy ray referred to in the present invention is an electron beam, an α ray,
β-rays, γ-rays, X-rays, neutron rays, or ultraviolet rays,
It is a generic term for ionizing radiation and light.

In the present invention, when curing the resin composition using ultraviolet rays as energy rays, the wavelength is 1,000 to 8,000
Angstrom ultraviolet rays can be irradiated in the air or nitrogen using low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, xenon lamps, gallium lamps, metal halide lamps, carbon arc lamps, or sunlight. Good.

The thus obtained energy ray-curable resin composition of the present invention can be used, for example, as a binder component for paints, adhesives, printing inks, magnetic recording media, and the like.

〔Example〕

Next, the present invention by reference examples, examples and comparative examples,
Although described more specifically, the present invention is not limited to only these examples.

In the following, all parts and percentages are by weight unless otherwise specified.

Reference Example 1 In a flask, 55 g of "Varnock DN-901S" (produced by Dainippon Ink and Chemicals, Inc., isocyanurated hexamethylene diisocyanate) and a hydroxyl value of 112 KOHmg /
g of bis (2-hydroxyethoxypropyl) polydimethylsiloxane was reacted at 80 ° C. for 4 hours with stirring, and further reacted with 4- (2-hydroxyethoxy) phenyl-2- (2-hydroxy ) 90 g of a 50% solution of propyl ketone in methyl ethyl ketone was added and reacted at 80 ° C. for 4 hours with stirring.

After that, by infrared spectrum analysis (IR analysis)
After confirming that the characteristic absorption of the isocyanate group disappeared, the intended compound (1) containing a siloxane skeleton and a group capable of generating a radical by light was obtained.

Reference Example 2 In a flask, 55 g of “Varnock DN-901S” and 50 g of bis (2-hydroxyethoxypropyl) polydimethylsiloxane having a hydroxyl value of 112 KOH mg / g were reacted at 80 ° C. for 4 hours with stirring. From 4- (2-
(Hydroxyethoxy) phenyl-2- (2-hydroxy) propyl ketone in 50% methyl ethyl ketone
g and 13 g of 2-hydroxypropyl acrylate were added and reacted at 80 ° C. for 4 hours with stirring.

After that, by IR analysis, it was confirmed that the characteristic absorption of the isocyanate group was lost, and the intended compound (2) containing a siloxane skeleton, a group generating a radical by light, and an acryloyl group was obtained. Was.

Reference Example 3 In a flask, 52.4 g of 4,4'-dicyclohexylmethane diisocyanate and 224 g of 2-dimethylolbutoxypropylmethylpolydimethylsiloxane having a hydroxyl value of 50 KOHmg / g were stirred at 80 ° C for 4 hours. Then, 45 g of a 50% solution of 4- (2-hydroxyethoxy) phenyl-2- (2-hydroxy) propyl ketone in methyl ethyl ketone and 30 g of pentaerythritol triacrylate are added, and the mixture is stirred at 80 ° C. For 4 hours.

After that, by IR analysis, it was confirmed that the characteristic absorption of the isocyanate group was lost, and the intended compound (3) containing a siloxane skeleton, a group generating a radical by light, and an acryloyl group was obtained. Was.

Reference Example 4 In a flask, a bis [3-epoxy having an epoxy equivalent of 490 g / mol was added.
(Oxylanylmethoxy) propyl] 98 g of polydimethylsiloxane and 15 g of acrylic acid were charged and reacted at 100 ° C. for 10 hours.

Next, 45 g of isophorone diisocyanate was added, and the reaction was carried out at 80 ° C. for 6 hours.

Thereafter, 95 g of a 50% methyl ethyl ketone solution of 4- (2-hydroxyethoxy) phenyl-2- (2-hydroxy) propyl ketone was added, and the mixture was stirred with 80 g of 80%.
The reaction was performed at 4 ° C. for 4 hours.

After that, by IR analysis, it was confirmed that the characteristic absorption of the isocyanate group was lost, and the compound (4) containing the objective siloxane skeleton, a group derived from radical I by light, and an acryloyl group was obtained. I got

Reference Example 5 In a flask, a bis [3-
(Oxiranylmethoxy) propyl] 98 g of polydimethylsiloxane and 4- (2-hydroxycarbonylmethoxy) phenyl 2-hydroxy-2-propyl ketone
47.6 g, and reacted at 100 ° C. for 10 hours.After confirming that the acid value was 0.5 KOH mg / g or less, the objective siloxane skeleton and a group that generates a radical by light were added. Compound (5) was obtained.

Reference Example 6 (Preparation Example of Urethane Acrylate) In a flask, 100 g of a polycaprolactone polyol having a hydroxyl value of 168 KOHmg / g, which is a ring-opened polymer of trimethylolpropane and epsilon caprolactone, synthesized by a conventional method, and isophorone 67g of diisocyanate
Is reacted at 80 ° C. for 4 hours with stirring, and then
35 g of hydroxyethyl acrylate was added and reacted at 80 ° C. for 4 hours with stirring.

After that, it was confirmed by IR analysis that the characteristic absorption of the isocyanate group had disappeared, and the intended urethane acrylate compound (1) was obtained.

Example 1 50 parts of the compound (1) obtained in Reference Example 1 and Reference Example 6
Was mixed with 50 parts of the compound (1) obtained in the above, and applied on a glass plate to a thickness of about 100 μm using an applicator.

Next, this was dried in a dryer at 100 ° C. for 15 minutes.

Thereafter, after the coated material was at room temperature, it was cured by irradiating it with an ultraviolet ray using a high-pressure mercury lamp of 80 W so that the irradiation amount was 1000 mj / cm2.

The cured product was subjected to an odor, a coefficient of kinetic friction, a scratch test with a diamond needle, and a measurement of solvent resistance. The results are summarized in Table 1.

Example 2 50 parts of the compound (1) obtained in Reference Example 2 and Reference Example 6
Was mixed with 50 parts of the compound (1) obtained in the above, and applied on a glass plate to a thickness of about 100 μm using an applicator.

Next, this was dried in a dryer at 100 ° C. for 15 minutes.

Thereafter, after the coated material was at room temperature, it was cured by irradiating it with an ultraviolet ray using a high-pressure mercury lamp of 80 W so that the irradiation amount was 1000 mj / cm2.

The cured product was subjected to an odor, a coefficient of kinetic friction, a scratch test with a diamond needle, and a measurement of solvent resistance. The results are shown in Table C1.

Example 3 50 parts of the compound (3) obtained in Reference Example 3 and Reference Example 6
Was mixed with 50 parts of the compound (1) obtained in the above, and applied on a glass plate to a thickness of about 100 μm using an applicator. Next, this was dried in a dryer at 100 ° C. for 15 minutes.

Thereafter, after the coating material was cooled to room temperature, the coating material was cured by irradiating ultraviolet rays with a high-pressure mercury lamp of 80 W so that the irradiation amount became 1000 mj / cm2.

The cured product was subjected to an odor, a coefficient of kinetic friction, a scratch test with a diamond needle, and a measurement of solvent resistance. The results are summarized in Table 1.

Example 4 50 parts of the compound (4) obtained in Example 4 and Reference Example 6
50 parts of the compound (1) obtained in the above was mixed and applied on a glass plate to a thickness of about 100 μm using an applicator. Next, this was dried in a dryer at 100 ° C. for 15 minutes.

After that, after the coating material is at room temperature, with an 80 W high-pressure mercury lamp, the irradiation amount becomes 1000 mj / cm2.
Curing was performed by irradiating ultraviolet rays.

The cured product was subjected to an odor, a coefficient of kinetic friction, a scratch test with a diamond needle, and a measurement of solvent resistance. The results are summarized in Table 1.

Example 5 50 parts of the compound (5) obtained in Reference Example 5 and Reference Example 6
Was mixed with 50 parts of the compound (1) obtained in the above, and applied on a glass plate to a thickness of about 100 μm using an applicator. Next, this was dried in a dryer at 100 ° C. for 15 minutes.

Thereafter, after the coated material was at room temperature, it was cured by irradiating it with an ultraviolet ray using a high-pressure mercury lamp of 80 W so that the irradiation amount was 1000 mj / cm2.

This cured product was subjected to an odor, a coefficient of kinetic friction, a scratch test with a diamond needle, and a measurement of solvent resistance. The results are shown in Table 1.

Comparative Example 1 100 parts of the compound (1) obtained in Reference Example 6 and 3 parts of benzyldimethyl ketal were mixed and applied to a thickness of about 100 μm on a glass plate using an applicator. . Next, this was dried in a dryer at 100 ° C. for 15 minutes.

Thereafter, after the coated material was at room temperature, it was cured by irradiating it with an ultraviolet ray using a high-pressure mercury lamp of 80 W so that the irradiation amount was 1000 mj / cm2.

The cured product was subjected to an odor, a coefficient of kinetic friction, a scratch test with a diamond needle, and a measurement of solvent resistance. The results are summarized in Table 1.

In addition, the point of the evaluation method about each hardened | cured material obtained by each Example and the comparative example is shown below.

Odor: The smell of the cured sample was smelled, and judgment was made with or without odor.

Dynamic friction coefficient: Measured with a diamond stylus under the conditions of Osaka Diamond No. 1, load 10 g, 100 mm / sec.

Scratch test: A scratch test was performed with a diamond needle under the conditions of Osaka Diamond No. 1, load 20 g, 100 mm / sec.

 Judgment was made with or without scratches after scratching.

Solvent resistance: 5 to 5 methyl ethyl ketone on the sample surface
One drop of 20 μm was dropped, covered with a watch glass to prevent evaporation, and allowed to stand for 1 hour. The surface was wiped off, and the appearance was visually judged.

[Effects of the Invention] As described above, the active energy ray-curable resin composition of the present invention has no odor and is not only on the surface curability, but also on the surface scratch resistance and the surface lubricity, In terms of chemical properties, they are all improved.

──────────────────────────────────────────────────の Continuation of the front page (51) Int.Cl. ⁷ identification code FI C09D 183/06 C09D 183/06 (58) Field surveyed (Int.Cl. ⁷ , DB name) C08G 77/38 C08L 83/06 C09D 183/06

Claims (3)

(57) [Claims] 1. A compound of the formula [I] And a siloxane skeleton represented by the general formula (II) An active energy ray-curable resin composition, characterized by containing a compound having a group generating a radical by light represented by the following formula in a weight ratio of 5 to 80%. 2. Formula (I) And a siloxane skeleton represented by the general formula (II) A group that generates a radical by light represented by
An active energy ray-curable resin composition comprising a compound having both an ethylenically unsaturated double bond and a weight ratio of 5 to 80%. 3. A compound of the general formula [I] And a siloxane skeleton represented by the general formula (II) A group that generates a radical by light represented by
An active energy ray-curable resin composition comprising a compound having both an ethylenically unsaturated double bond and a urethane bond in a weight ratio of 5 to 80%.