TW201321422A - Adamantane-containing polymer - Google Patents

Abstract

A polymer which contains a structure represented by formula (I).

Description

Gold steel alkyl polymer

The present invention relates to a polymer, a resin composition containing the same, and a hard coat film having a hardened layer obtained from the resin composition.

Various functional films are used in liquid crystal displays, plasma displays, organic EL displays, and the like. Among them, in recent years, devices in the form of touch panels represented by smart phones have become popular, and films that are harder and less scratch-resistant have been sought.

A method of imparting hardness to a film, and a method of hard-coating an ultraviolet curable resin is general. However, there is a problem that the film is bent due to curing shrinkage of the ultraviolet curable resin, and the productivity in the bonding step on the surface of the display is lowered, and the durability after bonding is also problematic.

In order to solve the above problem, Patent Document 1 discloses a method of providing two or more hard coat layers on at least one surface of a plastic film. However, this method has a problem that the coating step for providing two or more layers of the hard coat layer becomes complicated and the production cost becomes high.

Further, Patent Document 2 discloses that a reactive polymer which is subjected to an addition reaction using an epoxy group-containing (meth)acrylic copolymer and an unsaturated monocarboxylic acid in a hard coat layer, but hardness and bending suppression of the hard coat layer The balance is not sufficient.

[Previous Technical Literature] [Patent Document]

[Patent Document 1] Japanese Patent Laid-Open Publication No. 2005-53152

[Patent Document 2] Japanese Patent Laid-Open Publication No. 2008-69303

It is an object of the present invention to provide a polymer which can produce a hard coat film having high hardness and suppressing bending.

According to the invention, the following polymers and the like are provided.

A polymer comprising a structure represented by the following formula (I).

(wherein R ₁ , R ₄ and R ₆ are each a hydrogen atom or a methyl group. R ₂ and R ₅ are each a divalent aliphatic hydrocarbon group selected from a hydroxyl group, a halogen atom and a hetero atom, and 2 An aliphatic hydrocarbon group or a single bond. R ₃ is a hydrocarbon group, a halogen-substituted hydrocarbon group, a cyclic hydrocarbon group, a halogen-substituted cyclic hydrocarbon group, a halogen atom, a hydroxyl group, a carboxyl group, or a pendant oxy group. m is an integer of 0 to 15.

2. The polymer of the first item wherein R ₂ of the polymer represented by the above formula (I) is a single bond and m is 0.

3. An epoxy group of a copolymer obtained by copolymerizing a (meth) acrylate having an adamantyl group and a (meth) acrylate bonded with an epoxy group; a polymer obtained by reacting (meth)acrylic acid, or a carboxyl group of a copolymer obtained by copolymerizing a (meth) acrylate bonded with an adamantyl group and (meth)acrylic acid, and an epoxy group bonded thereto A polymer obtained by reacting (meth) acrylate.

4. A resin composition comprising the polymer according to any one of 1 to 3 and a photopolymerization initiator.

5. A hard coat film having a hardened layer obtained from the resin composition described in 4.

According to the present invention, it is possible to provide a polymer capable of producing a hard coat film having high hardness and suppressing bending.

[Best Practice for Carrying Out the Invention]

The polymer of the present invention contains a structure represented by the following formula (I).

(wherein R ₁ , R ₄ and R ₆ are each a hydrogen atom or a methyl group.

Each of R ₂ and R ₅ is a divalent aliphatic hydrocarbon group or a divalent aliphatic hydrocarbon group or a single bond selected from the group consisting of a hydroxyl group, a halogen atom and a hetero atom.

R ₃ is a hydrocarbon group, a halogen-substituted hydrocarbon group, a cyclic hydrocarbon group, a halogen-substituted cyclic hydrocarbon group, a halogen atom, a hydroxyl group, a carboxyl group, or a pendant oxy group (=O).

m is an integer from 0 to 15. )

The respective groups of the polymer represented by the formula (I) are as follows.

As R ₂ and R ₅ contains at least one kind of divalent aliphatic hydrocarbon group having a hydroxyl group, a halogen atom and a hetero atom selected of, for example may be configured as the following three.

(where n is an integer greater than 0.)

Examples of the divalent aliphatic hydrocarbon group of R ₂ and R ₅ include a methylene group, an exoethyl group, and a butyl group.

The hydrocarbon group of R ₃ may, for example, be a methyl group, an ethyl group, a butyl group or a t-butyl group.

The cyclic hydrocarbon group of R ₃ may, for example, be a cyclopentyl group or a cyclohexyl group.

The halogen-substituted hydrocarbon group of R ₃ is a group in which a hydrogen atom of the above hydrocarbon group is substituted with a halogen atom. Similarly, the halogen-substituted cyclic hydrocarbon group of R ₃ is a group in which a hydrogen atom of the above cyclic hydrocarbon group is substituted with a halogen atom.

And, R ₃ of the side 2 R ₃ group is bonded to the same carbon atom of the adamantane skeleton, and the two R ₃ are both hydroxy, the hydroxyl condensation and for this and other situations.

The polymer represented by the formula (I) is preferably a polymer wherein R ₂ is a single bond (direct bond) and m is 0.

The polymer having the structure represented by the formula (I) can be copolymerized by copolymerizing a (meth) acrylate having an adamantyl group bonded thereto and an epoxy group-bonded (meth) acrylate. The epoxy group of the copolymer is reacted with (meth)acrylic acid; or the (meth) acrylate bonded with adamantyl group is copolymerized with (meth)acrylic acid to obtain a carboxyl group of the obtained copolymer It is produced by reacting with a (meth) acrylate having an epoxy group bonded thereto.

A (meth) acrylate having an adamantyl group bonded thereto, for example, a compound having the following structure.

(wherein, R ₁ , R ₂ , R ₃ and m are the same as in the formula (I).)

A (meth) acrylate having an epoxy group bonded thereto, for example, a compound having the following structure. In the following formula, R ₅ , a group bonded to the ring-opened epoxy group, corresponds to R ₅ .

(In the formula, R _{4 is the} same as the formula (I). R ₅ ^' each is a divalent aliphatic hydrocarbon group or a divalent aliphatic hydrocarbon group or a single bond which is selected from a hydroxyl group, a halogen atom and a hetero atom. )

(Meth)acrylic acid, for example, a compound having the following structure.

(wherein, R _{6 is the} same as (I).)

The above-mentioned copolymerization can be carried out, for example, by a conventional radical polymerization method, and polymerization can be carried out using a radical polymerization initiator or the like in a solvent or without a solvent.

The radical polymerization initiator may, for example, be an azo initiator such as 2,2'-azobisisobutyronitrile or 2,2'-azobis-methyl-n-butyronitrile; A peroxide initiator such as mercaptoester, methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide or the like.

Further, a chain transfer agent such as dodecyl mercaptan, lauryl mercaptan, mercapto glycolate or mercaptoethanol may be used as necessary.

The amount of the radical polymerization initiator used is a (meth) acrylate in which an adamantyl group is bonded and an epoxy group-bonded (meth) acrylate, or an adamantyl group is bonded to the copolymerization. The total amount of the (meth) acrylate and the (meth)acrylic acid is usually from 0.01 to 50 parts by mass, preferably from 0.01 to 30 parts by mass, per 100 parts by mass. Free radical polymerization initiator When the amount used is in this range, the reaction time, the yield, and the like can be made good, and the desired weight average molecular weight can be obtained.

The solvent used for the copolymerization may, for example, be an alkyl alcohol such as methanol, ethanol, n-propanol or isopropanol; methyl cellosolve, ethylene glycol dimethyl ether or ethylene glycol diethyl ether; a glycol ether such as propylene glycol monomethyl ether or propylene glycol monoethyl ether; an aromatic hydrocarbon such as benzene, toluene, xylene or ethylbenzene; cyclopentane, cyclohexane or methylcyclohexane; An alicyclic hydrocarbon; an ether such as tetrahydrofuran, dioxane or diisopropyl ether; a ketone such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; methyl acetate or acetic acid; Esters such as ethyl ester, n-propyl acetate, ethyl propionate, propylene glycol monoethyl ether acetate, and the like. These solvents may be used alone or in combination of two or more.

The solvent used for the copolymerization, using a copolymerization component ((meth)acrylate bonded with adamantyl group and (meth)acrylate bonded with an epoxy group, or (methyl group bonded with an adamantyl group) The total concentration of the acrylate and the (meth)acrylic acid may be, for example, 0.5% by mass or more, preferably 5% by mass or more. In this case, the copolymerization component may be in a suspended state, but it is preferably dissolved.

The reaction temperature of the copolymerization reaction is usually 0 to 200 ° C, preferably 20 to 150 ° C. When the temperature is less than 0 ° C, there is a decrease in the reaction rate. On the other hand, when the temperature exceeds 200 ° C, the coloration of the obtained polymer becomes severe.

In terms of the reaction pressure of the copolymerization reaction, the absolute pressure is usually 0.01 to 10 MPa, preferably from atmospheric pressure to 1 MPa. In the case where the pressure exceeds 10 MPa, there is a safety problem and it becomes a need for a special device.

The reaction time varies depending on the type or amount of the polymerization initiator, the reaction temperature, and the like, and is usually from 1 minute to 24 hours, preferably from 1 to 10 hours.

In the copolymerization reaction, other (meth)acrylic monomers may be added as a copolymerization component without impairing the effect of the present invention.

Examples of other (meth)acrylic monomers include methyl (meth) acrylate, ethyl (meth) acrylate, t-butyl (meth) acrylate, and cyclohexyl (meth) acrylate. Ester, dicyclopentanyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, γ-butyrolactone (Meth) acrylate, etc.

Addition reaction after copolymerization, even if a copolymer of (meth) acrylate bonded with adamantyl group and (meth) acrylate bonded with epoxy group is added with (meth)acrylic acid a reaction of adding a copolymer of a (meth) acrylate bonded to an adamantyl group to a (meth)acrylic acid with an epoxy group-bonded (meth) acrylate, such that The reaction can be carried out in a solvent.

The solvent which can be used for the addition reaction may, for example, be cyclohexane, methylcyclohexane, ethylcyclohexane, toluene, xylene, MEK (methyl ethyl ketone), MIBK (methyl isobutyl ketone). , DMF (dimethylformamide), NMP (N-methyl-2-pyrrolidone), DMAc (N,N-dimethylacetamide), DMSO (dimethyl sulfoxide), and propylene glycol monomethyl Ethyl ether acetate and the like.

A catalyst may be used in the addition reaction, and examples of the catalyst include tetramethylammonium chloride, tetramethylammonium bromide, tetraethylammonium chloride, tetraethylammonium bromide, triphenylphosphine, and pyridine. Wait.

The constituent unit ratio (mole ratio) of the adamantyl unit and the (meth)acryl-based unit of the polymer represented by the formula (I), reflecting the mixing ratio at the time of copolymerization, and the adamantyl unit is 1% ~99%, preferably 10%~90%. When the adamantyl unit is less than 10%, there is a possibility that the bending of the obtained hard coat film becomes large, and the physical properties of the hard coat film obtained by more than 90% are not greatly different.

Further, the polymerization form of the polymer represented by the formula (I) is not particularly limited, and examples thereof include a random copolymer.

The polymer having the structure represented by the formula (I) is a polymer composed only of an adamantyl unit of the formula (I) and a (meth)acryl-based unit (that is, a polymer represented by the formula (I) Or a polymer substantially composed of an adamantyl unit of the formula (I) and a (meth)acryl-based unit.

The term "substantially constituted" means a total of adamantyl unit and (meth)acryl-based unit of the formula (I) in the polymer, for example, 90 mol% or more, 95 mol% or more, 98 mol% or more, Or 99% or more, and not The effect range of the present invention is impaired, and further includes an unreacted epoxy group terminal, an unreacted (meth) acrylate terminal or the like.

The weight average molecular weight of the polymer represented by the formula (I) is not particularly limited, but is preferably from 1,000 to 100,000. When the molecular weight is less than 1,000, the curvature of the obtained hard coat film becomes large. On the other hand, when the molecular weight exceeds 100,000, the viscosity of the resin solution becomes high and the workability becomes difficult.

The composition of the present invention contains the above-described polymer of the present invention and a photopolymerization initiator.

[Photopolymerization initiator]

As the photopolymerization initiator, a conventional photopolymerization initiator such as 2,2-dimethoxy-1,2-diphenylethane-1-one or 1-hydroxy-cyclohexyl-phenyl-one can be used. 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propane 1-ketone, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propenyl)-benzyl]phenyl}-2-methyl-propan-1-one, 2,4,6-trimethylbenzimidyl-diphenyl-phosphine oxide, bis(2,4,6-trimethylbenzylidene)-phenylphosphine oxide, and the like.

These may be used alone or in combination of two or more.

Among the above photopolymerization initiators, ethyl N,N-dimethylaminobenzoate, isoamyl N,N-dimethylaminobenzoate, pentyl-4-dimethylamine may be added. A photoinitiator such as a tertiary amine such as a benzoic acid ester, triethylamine or triethanolamine. Further, a titanocene compound or the like of CGI-784 or the like (manufactured by Ciba Specialty Chemicals Inc.) having absorption in the visible light region may be added in order to promote photoreaction.

Further, the photopolymerization initiator is a compound which absorbs light in the ultraviolet light or visible light region and radically polymerizes a photosensitive unsaturated double bond, and is not limited to a photopolymerization initiator or a photoinitiator. use.

The content of the photopolymerization initiator in the composition is, for example, 0.1 to 20% by mass, preferably 1 to 10% by mass. When the content of the photopolymerization initiator is less than 0.1% by mass, the photocurability is lowered. On the other hand, when the content is more than 20% by mass, the crystal of the photopolymerization initiator is precipitated or the bottom of the coating film is caused. Poor hardening.

The composition of the present invention may contain a polymer represented by the formula (I) and a photopolymerization initiator, and these components may be substantially or only composed of such components.

The term “substantially” means a content in the composition of the components, for example, 90% by mass or more, 95% by mass or more, 97% by mass or more, 98% by mass or more, or 99% by mass or more.

[solvent]

The composition of the present invention may be dissolved in a solvent as necessary.

The solvent may, for example, be an alkyl alcohol such as methanol, ethanol, n-propanol or isopropanol; methyl cellosolve, ethylene glycol dimethyl ether, ethylene glycol diethyl ether or propylene glycol monomethyl a glycol ether such as ether or propylene glycol monoethyl ether; an aromatic hydrocarbon such as benzene, toluene, xylene or ethylbenzene; an alicyclic hydrocarbon such as cyclopentane, cyclohexane or methylcyclohexane Ethers such as tetrahydrofuran, dioxane, diisopropyl ether; ketones such as acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone (MIRK), cyclohexanone, etc.; Acetic acid Esters such as ethyl ester, n-propyl acetate, ethyl propionate, propylene glycol monoethyl ether acetate, and the like. These may be used alone or in combination of two or more.

The content of the solvent is, for example, 5 mass% to 90 mass%, and preferably 10 mass% to 50 mass% from the viewpoint of drying.

[other ingredients]

The composition of the present invention may further contain other (meth)acrylic compounds, inorganic fine particles, a coating agent, and the like insofar as the effects of the present invention are not impaired and the balance of performance is not impaired.

Examples of the other (meth)acrylic compound include methyl (meth) acrylate, ethyl (meth) acrylate, t-butyl (meth) acrylate, and cyclohexyl (meth) acrylate. Dicyclopentanyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, γ-butyrolactone (A Acrylate, ethylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, tricyclic Decane dimethanol di(meth)acrylate, adamantanediol di(meth)acrylate, adamantane dimethanol di(meth)acrylate, pentaerythritol tri(meth)acrylate, adamantane triol (Meth) acrylate, adamantane trimethyl alcohol tri(meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy group (meth) acrylate or the like.

Inorganic microparticles, which can be used in the range of nm to 10 μm depending on the application. For example, conventional inorganic fine particles such as glass powder, cerium oxide powder, titanium oxide, zinc oxide, zirconium oxide, and aluminum oxide.

The coating agent may, for example, be an anthrone or a fluorine-based coating agent.

The composition of the present invention is preferably used as a hard coat resin composition (hard coater) for forming a hard coat layer. According to the adamantane skeleton of the polymer of the present invention, the hard coat layer has a high hardness and the bending of the hard coat layer is suppressed, and since the (meth) acrylate becomes a crosslinking unit, the hard coat can be made to have a higher hardness.

The hard coat layer obtained by curing the resin composition of the present invention is excellent in adhesion to a polyester film, and when a hard coat layer is formed, it can be directly applied to the surface of the polyester film without performing surface treatment such as corona treatment. The composition is applied and cured to form a hard coat film.

Further, in general, the polyester film is precipitated by heating, and the film is clouded and the haze value is increased. However, the hard coat layer obtained by curing the composition of the present invention is laminated on both surfaces of the polyester film. A hard coat film which does not become cloudy or can reduce whitening even if heated.

The hard coating agent is mainly a material for improving chemical resistance and damage resistance such as polycarbonate resin, acrylic resin, and polyethylene terephthalate resin. For example, by coating a hard coating resin composition and curing by a coating method such as spin coating, spray coating, shower coating, or immersion, a hard coat layer having a thickness of 2 to 10 μm is formed on the substrate to impart resistance to the substrate. Scratch.

The curing method of the composition of the present invention is not particularly limited, and a curing method using a heat curing method or ultraviolet irradiation can be usually used.

The heat curing method has a curing temperature of usually about 50 to 200 ° C, preferably 100 to 180 ° C. No hardening failure occurs at 50 ° C or higher. Below 200 ° C does not cause coloring and the like.

The hardening time varies depending on the components contained in the composition, and is usually 0.5 to 6 hours.

In the curing method by ultraviolet irradiation, the amount of ultraviolet light is usually about 50 to 5000 mJ/cm ² , preferably 100 to 4000 mJ/cm ² . After the ultraviolet irradiation, post-heating may be performed, and it is preferably carried out at 70 to 200 ° C for 0.5 to 12 hours.

[Examples] Example 1

In a 1000 mL round bottom flask equipped with a reflux cooling tube, a stirrer, a thermometer, and a nitrogen introduction tube, 88.1 g of 1-adamantyl methacrylate, 56.9 g of epoxy propyl methacrylate, and methyl isobutyl group were added. The ketone was 300 g and nitrogen was blown for 30 minutes. Thereafter, 8.2 g of azobisisobutyronitrile was further added, and the mixture was heated to 80 ° C and then reacted for 3 hours. Thereafter, the reaction solution was cooled to room temperature, and a nitrogen introduction tube was replaced with an air introduction tube, and 29.4 g of acrylic acid, 2.3 g of triphenylphosphine, and 35 mg of MQ-F were added, and the mixture was heated to 110 ° C while air-gasing to make an acid. The reaction was carried out for 12 hours until the valence became 5 mg-KOH/g or less.

The obtained polymer solution was cooled to room temperature, and MIBK was added in such a manner that the solid content concentration became 35% by weight to obtain a reactive polymer A solution.

Example 2

In addition to 112.2 g of 1-adamantyl methacrylate, 33.5 g of epoxy propyl methacrylate, 7.5 g of azobisiso-n-butyronitrile, 17.3 g of acrylic acid, and 1.4 g of triphenylphosphine, In the same manner as in Example 1, a reactive polymer B solution was obtained.

Example 3

In addition to 52.9 g of 1-adamantyl methacrylate, 79.6 g of epoxy propyl methacrylate, 8.8 g of azobisiso-n-butyronitrile, 41.2 g of acrylic acid, 3.3 g of triphenylphosphine, and examples In the same manner, a reactive polymer C solution was obtained.

Example 4

In a 1000 mL round bottom flask equipped with a reflux cooling tube, a stirrer, a thermometer, and a nitrogen introduction tube, 88.1 g of 1-adamantyl methacrylate, 34.4 g of methacrylic acid, and 300 g of methyl isobutyl ketone were added, and 30 was carried out. A few minutes of nitrogen pumping. Thereafter, 8.2 g of azobisisobutyronitrile was further added, and the mixture was heated to 80 ° C, and then reacted for 3 hours. Thereafter, the reaction liquid was cooled to room temperature, and a nitrogen introduction tube was replaced with an air introduction tube, and 56.9 g of epoxypropyl methacrylate, 2.7 g of triphenylphosphine, and 35 mg of MQ-F were added. Air blowing was performed, and the temperature was raised to 110 ° C, and the reaction was carried out for 12 hours at an acid value of 5 mg-KOH/g or less.

The obtained polymer solution was cooled to room temperature, and MIBK was added in such a manner that the solid content concentration became 35 wt% to obtain a reactive polymer D solution.

Example 5

A reactive polymer E solution was obtained in the same manner as in Example 1 except that 1-adamantyl methacrylate was used instead of 94.5 g of 3-hydroxy-1-adamantyl methacrylate.

Example 6

In addition to the substitution of 1-adamantyl methacrylate, it is 117.6 g of perfluoro-1-adamantyl methacrylate, 79.6 g of epoxy propyl methacrylate, 8.8 g of azobisiso-n-butyronitrile, A A reactive polymer F solution was obtained in the same manner as in Example 1 except that 400 g of isobutyl ketone, 41.2 g of acrylic acid, and 3.3 g of triphenylphosphine were used.

Example 7

In addition to the substitution of 1-adamantyl methacrylate, 55.1 g of methyl methacrylate, 78.2 g of epoxy propyl methacrylate, 12.3 g of azobisiso-n-butyronitrile, 40.4 g of acrylic acid and triphenyl group were used. A reactive polymer G solution was obtained in the same manner as in Example 1 except that 3.2 g of phosphine was used.

[Modulation of composition and evaluation of hard coat layer] Example 8

To 200 g of the reactive polymer A solution prepared in Example 1, 2.1 g of 1-hydroxy-cyclohexyl-phenyl-ketone (product name: IRGACURE 184) as a polymerization initiator was added to prepare a hard coating resin solution.

PET film with a thickness of 100 μm (made by Toray Co., Ltd.) On Lumirror T60), the prepared hard coat resin solution was applied using a bar coater, and dried at 90 ° C for 2 minutes. Thereafter, the coating layer was irradiated with a high pressure mercury lamp at 500 mJ/min to form a hard coat layer having a thickness of 5 μm.

The hard coat film of the obtained PET film and the hard coat layer laminate was evaluated by the following items. The results are shown in Table 2.

[pencil hardness]

The pencil hardness of the hard coat film was measured in accordance with JIS K5600 using a 750 g load pencil scraping tester.

[scratch resistance]

After applying a load of 200 gf to the steel wool # 0000, the surface of the hard coating film was rubbed back and forth 10 times, and the surface scratching condition was visually observed and evaluated by the following criteria.

○: no scratches

△: The scratch is not up to 10

×: more than 10 scratches

〔bending〕

The hard coat film was cut out to 10 cm × 10 cm, and the bending height of the film 4 corner was measured, and the average value was used as a curve.

[adhesion]

The peeling test was carried out on a hard-coated cut-in checkerboard grid (1 mm × 1 mm, 100) in accordance with JIS K5600, and the residual number of the hard coat layer after the peeling test was evaluated as the adhesion. For example, in the case where there is no peeling, the number of remaining is 100, and the total number of peelings is 0.

[total light transmittance]

The total light transmittance (unit: %) of the hard coat film was measured by using HGM-2DP (manufactured by Siegel Test Co., Ltd.) in accordance with JIS K7105.

Examples 9-14 and Comparative Examples 1-2

The hard coat resin solution was prepared in the same manner as in Example 8 in the same manner as in Example 8, and a hard coat film was produced and evaluated in the same manner as in Example 8 except that the prepared hard coat resin solution was used. The results are shown in Table 2.

Example 15

The hard coat liquid prepared in Example 12 was applied using a PET film (Lumirror T60, manufactured by Toray Industries, Inc.) having a thickness of 100 μm, and dried at 90 ° C for 2 minutes. Thereafter, the coating layer was irradiated with a high pressure mercury lamp at 500 mJ/min to form a hard coat layer having a thickness of 3 μm. This operation was also carried out on the opposite side of the film to obtain a PET film having a hard coat layer formed on both sides.

The obtained hard coat film was heated at 150 ° C for 1 hour, and the total light transmittance and the haze value before and after the heating were measured. The haze value was measured by a haze meter in accordance with JIS K7136. The results are shown in Table 3.

Comparative example 3

A hard coat film in which a hard coat layer was formed on both surfaces of a PET film was produced and evaluated in the same manner as in Example 15 except that the hard coat liquid prepared in Comparative Example 2 was used. The results are shown in Table 3.

Comparative example 4

The PET film (Lumirror T60, manufactured by Toray Industries, Inc.) was evaluated in the same manner as in Example 15. The results are shown in Table 3.

[industrial use]

A hard coat film having a hard coat layer obtained from the composition containing the polymer of the present invention has high hardness and can suppress bending, and can be used as a film for a display, particularly a film for a touch panel.

Although the embodiments and/or the embodiments of the present invention have been described in detail above, the present invention may be embodied in various embodiments and/or embodiments without departing from the spirit and scope of the invention. change. Accordingly, such various modifications are intended to be included within the scope of the present invention.

The contents of the Japanese Patent Application Serial No.

Claims (5)

A polymer characterized by the structure represented by the following formula (I), (wherein, each of R ₁ , R ₄ and R ₆ is a hydrogen atom or a methyl group, and each of R ₂ and R ₅ is a divalent aliphatic hydrocarbon group selected from the group consisting of a hydroxyl group, a halogen atom and a hetero atom; The aliphatic hydrocarbon group or single bond of a valence, and R ₃ is a hydrocarbon group, a halogen-substituted hydrocarbon group, a cyclic hydrocarbon group, a halogen-substituted cyclic hydrocarbon group, a halogen atom, a hydroxyl group, a carboxyl group, or a pendant oxy group, and m is an integer of 0 to 15). The polymer of claim 1, wherein R ₂ of the polymer represented by the above formula (I) is a single bond, and m is 0. A polymer characterized by copolymerizing an epoxy group of a copolymer obtained by copolymerizing a (meth) acrylate having an adamantyl group bonded to an epoxy group-bonded (meth) acrylate. The carboxyl group of the copolymer obtained by the reaction of acrylic acid or the copolymerization of (meth) acrylate bonded with adamantyl group and (meth)acrylic acid is bonded with an epoxy group (A) Base acrylate reaction. A resin composition containing the polymer according to any one of claims 1 to 3 and a photopolymerization initiator. A hard coat film characterized by having a hardened layer obtained from the resin composition described in claim 4.