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Composition curable with actinic energy ray and use thereof

Composition curable with actinic energy ray and use thereof description/claims

The present invention relates to an actinic energy ray-curable composition useful as paints or coating agents for products where scratch resistance is required.

In Japanese Laid-Open Patent Publication No. 2001-2744, the present inventors have proposed an ultraviolet curable composition containing an ultraviolet curable urethane (meth)acrylate oligomer and a photoinitiator. The oligomer is obtained by reacting an isocyanate prepolymer compound having three or more isocyanate groups in one molecule with a polycaprolactone-modified hydroxyethyl(meth)acrylate.

In a cured product of the ultraviolet curable composition, scratches generated on the surface of the product can be repaired by self-repairing ability. Therefore, the cured product has scratch resistance. Accordingly, the ultraviolet curable composition is useful as paints or coating agents for products where scratch resistance is required.

However, the scratch resistance of the cured product is not necessarily satisfied in some applications. This limits the applications for the ultraviolet curable composition.

An object of the present invention is to provide an actinic energy ray-curable composition capable of forming a cured product having excellent scratch resistance.

In order to achieve the above-described object, in one embodiment of the present invention, the following actinic energy ray-curable composition is provided. In a cured product having a thickness of 60 μm obtained from the composition, when a scratch mark is made at a vertical load of 235 mN using a diamond indenter with a tip diameter of 15 μm, the scratch mark is repaired by self-repairing ability under an atmosphere at 25° C. and at a relative humidity of 50%.

In another embodiment of the present invention, the following actinic energy ray-curable composition is provided.

The composition contains a urethane(meth)acrylate obtained by reacting an organic isocyanate having a plurality of isocyanate groups in one molecule with a polycaprolactone-modified alkyl(meth)acrylate. The urethane(meth)acrylate contains two or more kinds of urethane(meth)acrylates different from one another in a number of repetitions of a caprolactone unit per one residue of the polycaprolactone-modified alkyl(meth)acrylate.

In further another embodiment of the present invention, the following actinic energy ray-curable composition is provided. The composition contains a urethane(meth)acrylate obtained by reacting an organic isocyanate having a plurality of isocyanate groups in one molecule with two or more kinds of polycaprolactone-modified alkyl(meth)acrylates different from one another in a number of repetitions of a caprolactone unit per one molecule.

In a further another embodiment of the present invention, the following actinic energy ray-curable composition is provided. The composition contains a urethane(meth)acrylate obtained by reacting an organic isocyanate having a plurality of isocyanate groups in one molecule with a polycaprolactone-modified alkyl(meth)acrylate, and a urethane(meth)acrylate obtained by reacting an organic isocyanate having a plurality of isocyanate groups in one molecule with a hydroxyalkyl (meth)acrylate.

In further another embodiment of the present invention, the following actinic energy ray-curable composition is provided. The composition contains a urethane(meth)acrylate obtained by reacting an organic isocyanate having a plurality of isocyanate groups in one molecule with a polycaprolactone-modified alkyl(meth)acrylate and a hydroxyalkyl (meth)acrylate.

First, an actinic energy ray-curable composition according to a first embodiment of the present invention is described.

The actinic energy ray-curable composition according to the first embodiment contains two or more kinds of urethane (meth)acrylates different from one another in the number of repetitions of a caprolactone unit per one residue of a polycaprolactone-modified alkyl(meth)acrylate.

The average number of repetitions per one molecule of the urethane(meth)acrylate relative to the number of repetitions of the caprolactone unit per one residue of the polycaprolactone-modified alkyl(meth)acrylate is preferably in the range of from 1 to 5, more preferably in the range of from 1 to 2.5. The maximum difference in the number of repetitions of the caprolactone unit per one residue of the polycaprolactone-modified alkyl(meth)acrylate between two kinds of the urethane(meth)acrylates is preferably 9 or less, more preferably in the range of from 4 to 9.

Each of the urethane(meth)acrylates is synthesized by reacting an organic isocyanate with a polycaprolactone-modified alkyl(meth)acrylate. By mixing these urethane (meth)acrylates, the actinic energy ray-curable composition is prepared.

When reacting the organic isocyanate with the polycaprolactone-modified alkyl(meth)acrylate, the reaction temperature is preferably from an ordinary temperature to 100° C. and the reaction time is preferably from 1 to 10 hours.

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