JP5374761B1 - Active energy ray-curable composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an active energy ray-curable composition capable of forming a cured coating film having excellent transparency, which is slippery and hardly scratched.
SOLUTION: A paraffin or polyolefin (A) having a specific molecular weight that is a liquid at 25 ° C. and a number average molecular weight of 320 or more and 1000 or less per 100 parts by mass of the active energy ray-curable component (B) An active energy ray-curable composition contained in a range of not less than 3 parts by mass and not more than 3 parts by mass.
[Selection figure] None

Description

  The present invention relates to an active energy ray-curable composition and a member having a cured coating film using the composition. More specifically, the present invention relates to an active energy ray-curable composition capable of forming a cured film having both finger slipperiness (resistance when a finger is slid), scratch resistance, and high hardness.

Active energy ray-curable coatings are rapidly spreading compared to thermosetting coatings because they are fast-curing and have good productivity, and are excellent in hardness and scratch resistance.
For example, by including a wax component having a melting point of 125 ° C. or more and a particle size of 0.1 μm or less, a technique for forming a coating film that is excellent in scratch resistance and scratch resistance and is not slippery is disclosed ( Patent Document 1).

JP 2002-121247 A

In recent years, touch screen panels have begun to spread rapidly for various displays in smart phones, portable terminals, personal computers, home appliances, and the like. Therefore, the outermost surface of these touch screen panels is required to have excellent transparency, high scratch resistance and hardness, and to have good finger slipping.
However, the conventional active energy ray-curable coating material has high scratch resistance and hardness, but the surface of the cured product has a high coefficient of friction and has a problem of being caught when a finger is slid.

  The present invention solves the above-mentioned problems of the prior art, is a cured coating film having excellent transparency, excellent in finger slipperiness (low resistance when a finger is slid), and hard to scratch It is an object of the present invention to provide an active energy ray-curable composition that can form a film.

  In the present invention, a paraffin or polyolefin (A) having a number average molecular weight of 320 or more and 1000 or less and a liquid at 25 ° C. is 0.01 to 100 parts by mass of the active energy ray-curable compound (B). The present invention relates to an active energy ray-curable composition contained in a range of not less than 3 parts by mass and not more than 3 parts by mass.

  In the present invention, at least a part of at least one member selected from plastic, metal, wood and paper is provided with a cured coating film formed from the active energy ray-curable composition according to the present invention. It relates to a member with a cured coating film.

  The active energy ray-curable composition of the present invention can form a cured coating film that is excellent in transparency, hardly scratched, and has excellent finger slipperiness (resistance when a finger is slid). .

  The paraffin or polyolefin (A) which has a number average molecular weight of 320 or more and 1000 or less and is liquid at 25 ° C. used in the present invention will be described. Since this paraffin or polyolefin (A) functions as a component that imparts good slipperiness to the cured coating film, that is, a slipperiness imparting agent, it may be referred to as a slipperiness imparting agent (A). The number average molecular weight of the slipperiness-imparting agent (A) is preferably 320 to 1000, more preferably 350 to 1000, and still more preferably 400 to 1000.

The slipperiness-imparting agent (A) is liquid at 25 ° C. and has a number average molecular weight in the above range, thereby forming a cured coating film that is excellent in transparency, hard to be scratched, and excellent in finger slipperiness. .
If the slipperiness-imparting agent is solid at 25 ° C., the finger slipping property of the cured coating film tends to be reduced.
When the number average molecular weight of the slipperiness-imparting agent is small, the compatibility with the active energy ray-curable compound (B) described later is too good, and it does not float on the surface of the cured coating film, and the finger slipperiness tends to decrease is there. On the other hand, when the number average molecular weight of the slipperiness-imparting agent is larger than the above range, the compatibility with the active energy ray-curable compound (B) described later is lowered, and a uniform coating liquid cannot be obtained by separation. The slipperiness-imparting agent floats in the form of “droplets” on the surface of the cured coating film.

  Such a slipperiness-imparting agent (A) has a predetermined molecular weight, structure and state, and forms a cured coating film that is excellent in transparency, hard to be damaged, and excellent in finger slipperiness. If it is possible, there is no particular limitation.

Examples of the paraffin or polyolefin (A) having a number average molecular weight of 320 or more and 1000 or less and which is liquid at 25 ° C. include the following.
As such paraffin, Moresco White P-80 (manufactured by MORESCO: number average molecular weight 400), Moresco White P-120 (manufactured by MORESCO: number average molecular weight 470), Moresco white P-260 (MORESCO) Manufactured: number average molecular weight 550). Furthermore, hydrogenated isobutene such as Palm Dream 6 (manufactured by NOF Corporation: number average molecular weight 350) can also be used.
Examples of polyolefin include Versaflow LV (manufactured by Shamrock: number average molecular weight 890) which is polyethylene.
As the slipperiness imparting agent (A), a polyethylene compound is particularly preferable.

  The number average molecular weight referred to in the present invention is GPC (HLC-8220 GPC: manufactured by Tosoh Corporation), three columns (TSK-gel SuperHM-H: manufactured by Tosoh Corporation), THF as a developing solvent, 40 degrees Celsius, The molecular weight in terms of standard polystyrene was measured and calculated under the condition of a flow rate of 0.6 ml / min.

The curable composition according to the present invention comprises at least one slipperiness imparting agent (A) selected from paraffin or polyolefin and an active energy ray curable compound (B) (hereinafter simply referred to as “curable compound (B)”). Also). Hereinafter, the curable compound (B) will be described.
The curable compound (B) has two or more ethylenically unsaturated double bonds that contribute to curing so as to form a tough cured coating film that is excellent in scratch resistance and solvent resistance. It is preferable to mainly use a polyfunctional compound, particularly preferably 3 or more ethylenically unsaturated double bonds, and a monofunctional compound can also be used as an auxiliary. As the ethylenically unsaturated double bond, an acryloyl group and a methacryloyl group are preferable, and an acryloyl group is particularly preferable. The curable compound (B) may be used in combination of a plurality of compounds as exemplified below. Hereinafter, the active energy ray-curable compound (B) will be described.

Among the curable compounds (B), specific examples of polyfunctional compounds include dimethylol tricyclodecane diacrylate, (ethoxylated) bisphenol A diacrylate, (propoxylated) bisphenol A diacrylate, and cyclohexane di. Methanol diacrylate, (poly) ethylene glycol diacrylate, (ethoxylated) 1,6-hexanediol diacrylate, (propoxylated) 1,6-hexanediol diacrylate, (ethoxylated) neopentyl glycol diacrylate, (propoxy) ) Neopentyl glycol diacrylate, hydroxypivalic acid neopentyl glycol diacrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, trimethy Propanetri (meth) acrylate, ethylene oxide modified trimethylolpropane tri (meth) acrylate, propylene oxide modified trimethylolpropane tri (meth) acrylate, tris (acryloxyethyl) isocyanurate, caprolactone modified tris (acryloxyethyl) isocyanurate, Trimethylolethane tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, alkyl-modified dipentaerythritol tri (meth) acrylate, alkyl-modified di Pentaerythritol tetra (meth) acrylate, alkyl-modified dipentaerythritol penta (meth) acrylate DOO, caprolactone-modified dipentaerythritol hexa (meth) acrylate, ester compounds of polyhydric alcohols and (meth) acrylic acid such as 1,2,3-cyclohexane tetra (meth) acrylate;
Polyurethane poly (meth) acrylate, polyester poly (meth) acrylate, polyether poly (meth) acrylate, polyacryl poly (meth) acrylate, polyalkyd poly (meth) acrylate, polyepoxy poly (meth) acrylate, polyspiroacetal poly Polyfunctional poly (meth) acrylate compounds such as (meth) acrylate, polybutadiene poly (meth) acrylate, polythiol polyene poly (meth) acrylate, and polysilicon poly (meth) acrylate;
Ester compounds synthesized from polyhydric alcohols, polybasic acids and (meth) acrylic acid, for example, ester compounds synthesized from trimethylolethane / succinic acid / acrylic acid = 2/4 (molar ratio) It is done.

  Among the curable compounds (B), from the viewpoint of toughness and scratch resistance, poly (meth) acrylates such as polyurethane poly (meth) acrylate having 6 or more functional groups and polyepoxy poly (meth) acrylate, In addition, polyfunctional acrylates having 4 or more acryloyl groups in the molecule can be preferably used.

  Polyepoxy poly (meth) acrylate is, for example, a (meth) acryloyl group introduced by reacting an epoxy group of an epoxy resin with a carboxyl group of (meth) acrylic acid, and (meth) acrylic acid of a novolac type epoxy resin. Additives can be mentioned.

  Polyurethane poly (meth) acrylate is obtained, for example, by reacting polyisocyanate with (meth) acrylate having a hydroxyl group, containing an isocyanate group obtained by reacting polyol and polyisocyanate under the condition of excess isocyanate group. Some are obtained by reacting a urethane prepolymer with (meth) acrylates having a hydroxyl group. Alternatively, a hydroxyl group-containing urethane prepolymer obtained by reacting a polyol and a polyisocyanate under hydroxyl-excess conditions can be obtained by reacting with a (meth) acrylate having an isocyanate group.

  Examples of polyols include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, butylene glycol, 1,6-hexanediol, 3-methyl-1,5-pentane glycol, neopentyl glycol, hexanetriol, trimellilol propane, polytetra Examples include methylene glycol and a condensation polymer of adipic acid and ethylene glycol.

Examples of polyisocyanates include tolylene diisocyanate, xylene diisocyanate, hydrogenated xylene diisocyanate, diphenylmethane-4,4′-diisocyanate, hydrogenated diphenylmethane-4,4′-diisocyanate, norbornane diisocyanate methyl, isophorone diisocyanate, hexamethylene diisocyanate, and the like. Can be mentioned. Moreover, the trimethylol propane adduct body of the said diisocyanate compound, the burette body which reacted with water, the trimer which has an isocyanurate ring, etc. can be used.

  Examples of (meth) acrylates having a hydroxyl group include 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, ditrimethylolpropane tetraacrylate, and the like.

  Examples of (meth) acrylates having an isocyanate group include (meth) acryloyloxyethyl isocyanate, (meth) acryloyloxypropyl isocyanate, (meth) acryloyl isocyanate, and the like.

  The curable composition concerning this invention contains the said slipperiness | lubricity imparting agent (A) in the range of 0.01-3 mass parts with respect to 100 mass parts of said curable compounds (B), and is 0.02-1. It is preferable to contain 0.5 mass part, and it is more preferable to contain 0.1-0.5 mass part. If it is less than 0.01 parts by mass, the effect of finger slipping may be insufficient, and if it exceeds 3 parts by mass, the basic performance such as scratch resistance, transparency, and adhesion as a cured coating film may be impaired. is there.

The curable composition according to the present invention is cured by irradiating active energy rays such as ultraviolet rays and electron beams. In the case of curing by ultraviolet irradiation, the curable composition contains a photopolymerization initiator.
Examples of the photopolymerization initiator used include acetophenones, benzoins, benzophenones, phosphine oxides, ketals, anthraquinones, thioxanthones, and the like. Specifically, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin butyl ether, diethoxyacetophenone, benzyldimethyl ketal, 2-hydroxy-2-methylpropiophenone, 1-hydroxycyclohexyl phenyl ketone, benzophenone, 2, 4,6-trimethylbenzoindiphenylphosphine oxide, Michler's ketone, isoamyl N, N-dimethylaminobenzoate, 2-chlorothioxanthone, 2,4-diethylthioxanthone and the like, and these photopolymerization initiators are used alone. Two or more types may be used in combination.

  These photopolymerization initiators have a total of 100 masses of the slipperiness-imparting agent (A), the active energy ray-curable compound (B), and the photopolymerization initiator from the viewpoint of ensuring appropriate crosslinking density and hard coat properties. % Is preferably contained in an amount of 0.1 to 20% by mass, more preferably 1 to 15% by mass.

The curable composition concerning this invention can contain a solvent in view of the convenience of coating. That is, the solvent is used to adjust the viscosity and leveling properties of the curable composition (also referred to as a coating solution or a coating composition), or the drying property at the time of coating, and the coating method of the curable composition. If necessary, an appropriate amount may be blended. Therefore, the solid content of the curable composition is not particularly limited, but may be, for example, 20% by mass to 100% by mass.
Specific examples of the solvent include the following. These can be used alone or in combination of two or more.

  Examples of the ether solvent include dibutyl ether, dimethoxyethane, diethoxyethane, propylene oxide, 1,4-dioxane, 1,3-dioxolane, 1,3,5-trioxane, tetrahydrofuran, anisole, and phenetole.

  Examples of ketone solvents include acetone, methyl ethyl ketone, diethyl ketone, dipropyl ketone, diisobutyl ketone, methyl isobutyl ketone, 2-octanone, 2-pentanone, 2-hexanone, cyclopentanone, cyclohexanone, methylcyclohexanone, acetylacetone, 1,2 -Diacetoxyacetone and the like.

  Examples of the ester solvents include ethyl formate, propyl formate, pentyl formate, methyl acetate, ethyl acetate, propyl acetate, methyl propionate, ethyl propionate, γ-ptyrolactone, methyl 2-methoxyacetate, methyl 2-ethoxyacetate, 2- Examples include ethyl ethoxy acetate, ethyl 2-ethoxypropionate, isobutyl acetate, methyl acetoacetate, ethyl acetoacetate and the like.

  Examples of alcohol solvents include methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, cyclohexyl alcohol, 2-methoxyethanol, 2-propoxyethanol, 2-butoxyethanol, diacetone alcohol, etc. Is mentioned.

Examples of the saturated hydrocarbon solvent include hexane, heptane, octane, cyclohexane, methylcyclohexane, and ethylcyclohexane.
Examples of the aromatic solvent include benzene, toluene, xylene and the like.
Examples of glycol solvents include ethylene glycol ethyl ether, ethylene glycol isopropyl ether, ethylene glycol butyl ether, propylene glycol methyl ether, ethyl carbitol, and butyl carbitol.

  The curable composition further includes a photosensitizer, a light stabilizer, an ultraviolet absorber, a catalyst, a colorant, a leveling agent, an antifoaming agent, a polymerization accelerator, an antioxidant, a flame retardant, if necessary. One or more of an infrared absorber, a surfactant, a surface modifier, a thixotropic agent and the like can be appropriately added within a range that does not impair the effects of the present invention.

When the curable composition according to the present invention is applied to various members and contains an organic solvent, it is dried and then irradiated with active energy rays to form a cured coating film.
The thickness of the cured coating film is preferably 3 to 20 μm from the viewpoint of ensuring pencil hardness and wear resistance, and avoiding the deterioration of adhesion to members or the generation of cracks in the cured coating film. It is more preferably ˜15 μm, and further preferably 4 to 10 μm.

The member for providing the cured coating film can be appropriately selected from the group consisting of plastic, metal, wood and paper. Furthermore, a composite member composed of a plurality of members can also be selected. These members may have a flat shape such as a film or paper, or may have a three-dimensional shape.
The plastic film is preferably transparent.

Examples of the plastic material include transparent polymers such as polyester polymers, cellulose polymers, polycarbonate polymers, and acrylic polymers.
Examples of the polyester polymer include polyethylene terephthalate (PET) and polyethylene naphthalate. Examples of the cellulose polymer include diacetyl cellulose and triacetyl cellulose (TAC). Examples of the acrylic polymer include polymethyl methacrylate.

Examples of the plastic material include transparent polymers such as a styrene polymer, an olefin polymer, a vinyl chloride polymer, and an amide polymer.
Examples of the styrene polymer include polystyrene and acrylonitrile / styrene copolymer. Examples of the olefin polymer include polyethylene, polypropylene, polyolefin having a cyclic or norbornene structure, and an ethylene / propylene copolymer. Examples of the amide polymer include nylon and aromatic polyamide.

  Furthermore, imide polymer, sulfone polymer, polyether sulfone polymer, polyether ketone polymer, polyphenyl sulfide polymer, vinyl alcohol polymer, vinylidene chloride polymer, vinyl butyral polymer, arylate polymer, polyoxymethylene Examples thereof include transparent polymers such as polymer-based polymers, epoxy-based polymers, and blends of the aforementioned polymers. In particular, those having a low birefringence are preferably used.

  When a plastic film is used as a member, the surface on which a cured coating film is formed is selected from the group of acrylic resins, copolymer polyester resins, polyurethane resins, styrene-maleic acid graft polyester resins, acrylic graft polyester resins, and the like. A so-called easy adhesion type film provided with a resin layer can also be used.

  Among the members, the thickness of the flat member can be determined as appropriate, but in the case of a plastic film, it is generally about 10 to 500 μm from the viewpoints of workability such as strength and handling, and thin layer properties. It is preferable. 20-300 micrometers is especially preferable, and 30-200 micrometers is more preferable. When the member has a three-dimensional shape, the thickness is not limited.

  The curable composition may be applied by a conventional method, for example, a bar coating method, a knife coating method, a roll coating method, a blade coating method, a die coating method, or a gravure coating method. When a solvent is included, it is preferable to dry the coating film at about 50 to 150 ° C. after applying the curable composition.

As described above, the curable composition after application can be cured by irradiation with active energy rays. Examples of active energy rays include ultraviolet rays and electron beams. When ultraviolet rays are used, a light source such as a high-pressure mercury lamp, an electrodeless lamp, or a xenon lamp is used, and the ultraviolet irradiation amount is preferably about 100 to 2000 mJ / cm ² , for example. The obtained cured coating film is excellent in bending resistance.

  Hereinafter, the present invention will be specifically described by way of examples. In the examples, “parts” and “%” mean “parts by mass” and “% by mass”, respectively.

Example 1
100 parts of pentaerythritol triacrylate (trade name: “Aronix M305”, manufactured by Toa Gosei Co., Ltd.) as the compound (B), hydrogenated isobutene having a number average molecular weight of 350 as a paraffin (trade name “Pearl Reme 6”: NOF Corporation) 0.5 parts, Irgacure 184 (manufactured by Ciba Specialty Chemicals) as a photopolymerization initiator, and 101.5 parts of ethyl acetate were mixed to prepare a curable composition (coating composition or coating) having a nonvolatile content of 50%. Also called liquid.
This composition was applied to the surface of an easily adhesive-treated polyethylene terephthalate film (trade name: “Cosmo Shine A4100” manufactured by Toyobo Co., Ltd.) having a thickness of about 100 μm using a bar coater, and the solvent was removed with a hot air oven. After that, ultraviolet rays were irradiated with a high-pressure mercury lamp with an output of 80 w / cm to polymerize and cure the coating film to obtain a substrate with a cured coating film having a coating layer having a dry film thickness of about 6 μm.

(Examples 2-3)
1.5 parts (Example 2), 3 parts (Example 3) of hydrogenated isobutene having a number average molecular weight of 350 used in Example 1 (trade name “Pearl Ream 6” manufactured by NOF Corporation) A curable composition was obtained in the same manner as in Example 1 except that it was used, and a member with a cured film was obtained in the same manner.

(Examples 4 to 6)
Instead of hydrogenated isobutene having a number average molecular weight of 350 (trade name “Pearl Ream 6”: manufactured by NOF Corporation), polyethylene having a number average molecular weight of 890 which is a polyolefin (trade name: “Versaflow LV”, manufactured by Shamrock) Was used in the same manner as in Example 1 except that 0.02 part (Example 4), 0.1 part (Example 5), and 0.2 part (Example 6) were used. .

(Examples 7 to 8)
Instead of hydrogenated isobutene having a number average molecular weight of 350 (trade name “Pearl Reme 6” manufactured by NOF Corporation), paraffin having a number average molecular weight of 400 (trade name “MORESCO White P-80” manufactured by MORESCO) Were used in the same manner as in Example 1 except that 0.02 part (Example 7) and 0.3 part (Example 8) were used, and a member with a cured film was obtained in the same manner.

(Examples 9 to 10)
Instead of hydrogenated isobutene having a number average molecular weight of 350 (trade name “Pearl Reme 6” manufactured by NOF Corporation), paraffin having a number average molecular weight of 550 (trade name “MORESCO White P-260” manufactured by MORESCO) Was used in the same manner as in Example 1 except that 0.02 part (Example 9) and 0.3 part (Example 10) were used, and a member with a cured film was obtained in the same manner. .

(Comparative Example 1)
A member with a cured coating film was obtained in the same manner as in Example 1 except that the paraffin used in Example 1 was not used.

(Comparative Example 2)
The hydrogenated isobutene having a number average molecular weight of 350 (trade name “Pearl Ream 6” manufactured by NOF Corporation) was changed to a hydrogenated isobutene having a number average molecular weight of 280 (trade name “PEARL REAM 4” manufactured by NOF Corporation). In the same manner as in Example 2, a substrate with a cured film was obtained.

(Comparative Example 3)
Except for changing the hydrogenated isobutene having a number average molecular weight of 350 (trade name “Pearl Reme 6” manufactured by NOF Corporation) to the hydrogenated isobutene having a number average molecular weight of 1200 (trade name “PEARL REME 18” manufactured by NOF Corporation). In the same manner as in Example 2, a substrate with a cured film was obtained.

(Comparative Example 4)
Instead of polyethylene having a number average molecular weight of 890 (trade name: “Versaflow LV”, manufactured by Shamrock) used in Example 5, polyethylene having a number average molecular weight of 2150 (trade name: “Versaflow EV”, Shamrock) (Product made) Except having used 0.1 part, it carried out similarly to Example 5, and obtained the curable composition, and obtained the member with a cured film similarly.

(Comparative Example 5)
Instead of polyethylene having a number average molecular weight of 890 (trade name: “Versaflow LV”, manufactured by Shamrock) used in Example 5, polyethylene having a number average molecular weight of 3200 (trade name: “Versaflow HV”, manufactured by Shamrock) (Product made) Except having used 0.1 part, it carried out similarly to Example 3, and obtained the curable composition, and obtained the member with a cured film similarly.

(Comparative Example 6)
In place of polyethylene having a number average molecular weight of 890 (trade name: “Versaflow LV”, manufactured by Shamrock) used in Example 5, polyethylene having a number average molecular weight of 2500 (trade name: “Versaflow BASE”, Shamrock) (Manufactured) An attempt was made to obtain a coating agent using 0.1 part, but the solution was not uniform and a member with a cured film could not be obtained.

(Comparative Example 7)
Instead of the polyethylene having a number average molecular weight of 890 (trade name: “Versaflow LV”, manufactured by Shamrock) used in Example 5, a solid polyethylene compound having a number average molecular weight of 900 and a melting point of 118 ° C. (trade name: “High Wax” A curable composition was obtained in the same manner as in Example 5 except that 0.1 part of “100P HP10A” (manufactured by Mitsui Chemicals) was used, and a member with a cured film was obtained in the same manner.

(Comparative Example 8)
A curable composition was obtained in the same manner as in Example 1 except that 5 parts of hydrogenated isobutene having a number average molecular weight of 350 used in Example 1 (trade name “Pearl Reme 6” manufactured by NOF Corporation) was used. Similarly, a member with a cured film was obtained.

(Comparative Example 9)
A curable composition was obtained in the same manner as in Example 2 except that 5 parts of polyethylene having a number average molecular weight of 890 used in Example 2 (trade name: “Versaflow LV”, manufactured by Shamrock) was used. Thus, a member with a cured film was obtained.

  About the member with a cured coating film of Examples 1-10 and Comparative Examples 1-10, the following physical-property evaluation was performed and the result was put together in Table 1.

(Pencil hardness)
Based on JISK5400, it measured with the load of 750g with respect to the cured coating film surface of a member with a cured coating film using the Clemens type scratch hardness tester (model | form: product made from HA-301 tester industry company).

(Abrasion resistance)
Place a square pad of square centimeter equipped with # 0000 steel wool on the cured coating surface of a member with a cured coating film, reciprocate 10 times with a load of 500 g, evaluate the appearance visually, and measure the number of scratches did.

(Haze value / total light transmittance)
The haze value (Hz) and the total light transmittance (T.t.) of the member with a cured coating film were measured using a Haze Meter (model: NDH2000, manufactured by Nippon Denshoku).

(Measurement of dynamic friction coefficient)
With respect to the cured coating film surface of the member with the cured coating film, the load is 200 g, the pulling speed is 500 mm / min, the measurement time is 60 seconds, the measurement temperature is 25 degrees, and the measurement frequency is 5 times. The simple average value of the measured values of the dynamic friction coefficient of the coating surface was 5 times.

(Slipperiness of fingers)
The slipperiness was evaluated by placing the index finger lightly on the cured coating surface of the member with the cured coating film and rubbing it 10 times.
○: There is little resistance to the finger and it can be easily slid.
×: Resistant to fingers and difficult to slide

  From the results shown in Table 1, it was found that the members with cured coating films using the curable compositions of Examples 1 to 10 were excellent in transparency, scratch resistance, pencil hardness, slipperiness, and the like. Therefore, these members with a cured coating film can be suitably used for applications requiring hard coat properties, transparency, and slipperiness, such as displays, touch panels, and building materials.

On the other hand, in Comparative Example 1 containing no slipperiness-imparting agent (A), the hard coating properties such as scratch resistance and pencil hardness of the cured coating film are good, but the friction coefficient is high and the finger slipping property is insufficient. Was.
In Comparative Example 2 containing a hydrogenated polyisobutene having a number average molecular weight of 280, the hard coating properties such as scratch resistance and pencil hardness of the cured coating film were good, but the friction coefficient was high and the finger slipperiness was insufficient. .

In Comparative Example 3 containing hydrogenated polyisobutene having a number average molecular weight of 1200, droplets were confirmed on the surface of the member with the cured coating film, and evaluation could not be performed.
Comparative Examples 4 and 5 containing polyethylenes having number average molecular weights of 2100 and 2500 were the same as Comparative Example 3, and droplets were confirmed on the surface of the member with the cured coating film, and evaluation could not be performed.
In the case of Comparative Example 6 containing polyethylene having a number average molecular weight of 3200, the curable composition was separated, and a member with a cured coating film could not be created.

  Comparative Example 7 containing a solid polyethylene compound having a number average molecular weight of 900 has good hard coat properties such as scratch resistance and pencil hardness of the cured coating film, but has a high haze value and is opaque and has a high friction coefficient. The slipperiness was also insufficient.

  Comparative Example 8 containing 5 parts of hydrogenated polyisobutene and Comparative Example 9 containing 5 parts of polyethylene were both the same as Comparative Example 3, and droplets were confirmed on the surface of the member with the cured coating film, and evaluation could not be performed. .

  The active energy ray-curable composition according to the present invention can be suitably used for imparting slipperiness to an optical film member, as well as various plastic molded products, lenses on the outermost surface of a camera, lenses for spectacles, and architecture. It can also be used to impart the same function to the surfaces of window glass of various objects and vehicles and various printed materials. Or it can also be used in order to give slipperiness to the surface of a wooden member.

Claims (2)

  With respect to 100 parts by mass of the active energy ray-curable compound (B), the number average molecular weight is 320 or more and 1000 or less, and the paraffin or polyolefin (A) that is liquid at 25 ° C. is 0.01 part by mass or more and 3 An active energy ray-curable composition that is contained in a range of at most parts by mass.   A cured coating film formed from the active energy ray-curable composition according to claim 1 is provided on at least a part of at least one member selected from glass, plastic, metal, a wooden member, and paper. A member with a cured coating.