JP5831797B2 - Non-aqueous undercoat agent for plastic film with active energy ray cured film and plastic film with active energy ray cured film - Google Patents

Description

  The present invention relates to a non-aqueous undercoat agent used as an undercoat layer of a laminated film having an active energy ray curable film layer and a plastic film layer, and a plastic film with an active energy ray curable film using the undercoat agent. About.

  Plastic films made of thermoplastic resins such as polystyrene film, polycarbonate film, and polyester film are used for various industrial applications. In particular, polyester films are applied to various products because of their excellent mechanical strength and transparency.

  By the way, a plastic film may be difficult to adhere to a cured film (hereinafter referred to as an active energy ray cured film) made of a material that is cured with active energy rays such as pentaerythritol triacrylate. In order to improve adhesion, surface treatment such as corona discharge or sand blasting may be performed. However, there is a limit to the improvement in adhesion, and there is a problem that the adhesion decreases with time, and therefore an easily adhesive undercoat layer may be provided in advance on the surface of the plastic film.

  Conventional undercoat layers are mainly made of polyester resin, acrylic resin or the like, and polyisocyanate or the like as a crosslinking agent (see, for example, Patent Document 1 and Patent Document 2). However, since the main agent and the crosslinking agent are generally aqueous solutions or aqueous dispersions, it may be difficult to obtain an undercoat film in a short time. In addition, it has been pointed out that the moisture resistance of the undercoat layer is generally inferior and the adhesiveness decreases with time.

Japanese Patent Laid-Open No. 10-100349 International Publication No. WO2004 / 065120

  The present invention provides an undercoat film that is excellent in adhesion (hereinafter simply referred to as adhesion) between a cured film made of an active energy ray-curable material and a plastic film and also has good moisture resistance for a relatively short time. It is an object of the present invention to provide a non-aqueous undercoat agent that can be formed using

  As a result of intensive studies, the present inventor has found that the above problems can be solved by an undercoat agent having the following constitution.

  That is, the present invention comprises an active compound containing a branched polyester resin (A) having a hydroxyl group, an active energy ray polymerizable functional group and a compound (B) having a hydroxyl group, and a polyisocyanate (C) having at least three isocyanate groups. Non-aqueous undercoat agent for plastic film with energy ray curable film; active energy ray comprising an undercoat layer comprising the undercoat agent and an active energy ray curable film layer laminated in this order on at least one surface of the plastic film The present invention relates to a plastic film with a cured film.

  According to the undercoat agent of the present invention, an undercoat layer that adheres well to both a cured film made of an active energy ray-curable material and a plastic film (particularly a polyester film) can be obtained in a relatively short time. Further, the undercoat layer is excellent in moisture resistance and has a small decrease in adhesion over time. In addition, the undercoat agent of the present invention is cured in a short time even at a relatively low temperature and is excellent in drying properties, and is therefore suitable for a plastic film having poor heat resistance and a thin plastic film.

That is, the present invention contains a branched polyester resin having a hydroxyl group (A), an active energy ray-polymerizable functional group and a compound having a hydroxyl group (B), and a polyisocyanate having at least three isocyanate groups (C) , and The component (B) is at least one monohydroxy selected from the group consisting of trimethylolpropane di (meth) acrylate, glycerin di (meth) acrylate, dipentaerythritol penta (meth) acrylate and pentaerythritol tri (meth) acrylate. Poly (meth) acrylates (B-2) and / or at least one polyhydroxy poly (meth) acrylate selected from the group consisting of pentaerythritol di (meth) acrylate and dipentaerythritol tetra (meth) acrylate ( Characterized in that it is a -3), non-aqueous undercoating formulation for the active energy ray-curable coating with a plastic film; on at least one side of a plastic film, an undercoat layer made of the undercoating formulation, and the active energy ray-curable coating layer Relates to a plastic film with an active energy ray-cured film, which is laminated in this order.

Undercoating formulation according to the present invention, branched polyester resin having a hydroxyl group (A) (hereinafter, (A) referred to as the component), a predetermined active energy ray-polymerizable compound (B) (hereafter, referred to as component (B)), And a polyisocyanate (C) having at least three isocyanate groups (hereinafter referred to as component (C)).

  The component (A) is not particularly limited as long as it is a polyester resin having a hydroxyl group in the molecule and having a branched molecular structure, and various known ones can be used. Specifically, dicarboxylic acids (a1) (hereinafter referred to as component (a1)), diols (a2) (hereinafter referred to as component (a2)), and triols (a3) (hereinafter referred to as component (a3)) A dehydration condensate consisting of is preferred.

  Specific examples of the component (a1) include aromatic dicarboxylic acids such as isophthalic acid, terephthalic acid, orthophthalic acid, diphenylmethane-4,4′-dicarboxylic acid, naphthalene acid; oxalic acid, malonic acid, succinic acid, glutaric acid, Aliphatic (unsaturated) dicarboxylic acids such as adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, maleic acid, fumaric acid, succinic acid, citraconic acid; 1 Alicyclic dicarboxylic acids such as 1,4-cyclohexanedicarboxylic acid and 1,2-cyclohexanedicarboxylic acid; monoalkyl esters or dialkyl esters thereof (both having about 1 to 3 carbon atoms in the alkyl group); anhydrides thereof, etc. Is mentioned. The component (a1) preferably contains an aromatic dicarboxylic acid from the viewpoint of adhesion and moisture resistance. As the aromatic dicarboxylic acid, terephthalic acid, dimethyl terephthalate, isophthalic acid, dimethyl isophthalate, naphthalene are particularly preferred. Particularly preferred is at least one selected from the group consisting of acid, dimethyl naphthalate and phthalic anhydride. Moreover, it is preferable that content of aromatic dicarboxylic acid in (a1) component shall be about 30-100 mol% normally from a viewpoint of adhesiveness with a polyester film.

  Specific examples of the component (a2) include ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,5 -Aliphatic diols such as pentanediol, 1,6-hexanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 2-methyl-1,3-propanediol; cyclohexanedimethanol, cyclohexanediol, Alicyclic diols such as ethylene oxide adducts of hydrogenated bisphenol A; aromatic diols such as catechol, resorcinol, xylylene glycol, bishydroxyethoxybenzene, and ethylene oxide adducts of bisphenol A; 4 Polyethylene glycol above, such as polyalkylene glycols such as polypropylene glycol.

  The component (a3) is a component used for giving a branched structure to the component (A). In the present specification, “branched structure” means “crosslinked structure”. Specific examples of the component (a3) include glycerin, trimethylolpropane, trimethylolethane, 1,2,6-hexanetriol, 1,2,4-butanetriol and the like. In addition, tetraols such as erythritol, sorbitol, pentaerythritol, and dipentaerythritol can be used in combination with the component (a3).

  Although the usage-amount of (a1) component-(a3) component is not specifically limited, Usually, when the sum total of (a1) component and (a2) component is 100 mol, (a1) component is 30-70 mol% The component (a2) is about 70 to 30 mol%. Moreover, (a3) component is about 0.5-5 mol% normally with respect to a total of 100 mol of (a1) component and (a2) component.

  The dehydration condensate comprising the components (a1) to (a3) can be obtained according to various known polyester production methods. The conditions for the dehydration condensation reaction are not particularly limited, and the reaction can be carried out under normal pressure or reduced pressure. In the esterification reaction, various known esterification catalysts such as antimony trioxide, tetrapropyl titanate, tetrabutyl titanate, tetrastearyl titanate, dibutyltin dilaurate, dibutyltin dichloride, zinc oxide, and cobalt octylate can be used. The amount used is usually about 0 to 5% by weight based on the total weight of the components (a1) to (a3).

  The physical properties of the component (A) thus obtained are not particularly limited. For example, the hydroxyl value (JIS K-1557-1) is usually in the range of about 10 to 40 mgKOH / g, preferably 15 to 30 mgKOH / g. When the hydroxyl value is 10 mgKOH / g or more, the curability is improved, the crosslinking density of the undercoat layer is improved, and the moisture resistance is improved. Moreover, adhesiveness becomes favorable by a hydroxyl value being 40 mgKOH / g or less. In addition, a hydroxyl value can be adjusted with the usage-amount of said (a3) component.

  Further, from the viewpoint of adhesion and moisture resistance, the glass transition temperature of the component (A) is usually about 0 to 60 ° C., preferably about 10 to 50 ° C., and the number average molecular weight (polystyrene conversion value by gel permeation chromatography) ) Is usually about 5,000 to 22,000, preferably about 8,000 to 20,000.

As the component (B), from the viewpoint of adhesion and moisture resistance, trimethylolpropane di (meth) acrylate, glycerin di (meth) acrylate, dipentaerythritol penta (meth) acrylate and pentaerythritol tri (meth) acrylate are used. At least one monohydroxy poly (meth) acrylate (B-2) (hereinafter referred to as (B-2) component) selected from the group consisting of: and / or pentaerythritol di (meth) acrylate and dipentaerythritol tetra (meth) At least one polyhydroxy poly (meth) acrylate (B-3) selected from the group consisting of acrylates (hereinafter referred to as component (B-3)) is used . Since the component (B) has a (meth) acryloyl group in the molecule, the polymerization rate is high, and an undercoat layer can be obtained in a short time. In addition, the component (B) contributes to the adhesion between the active energy ray-cured film layer and the undercoat layer, and also has a hydroxyl group in the molecule, so that it is added to the later-described component (C) and added to the undercoat. It is considered that it is incorporated in the layer and contributes to the adhesion between the plastic film layer and the undercoat layer.

  The component (C) is a component capable of reacting with both the component (A) and the component (B), and the components (A) to (C) undergo a cross-linking reaction integrally through a reaction between a hydroxyl group and an isocyanate. As a result, it is considered that an undercoat layer having the desired effect can be obtained.

  Specific examples of the component (C) include, for example, a diisocyanate nurate (C-1) represented by the following general formula (1) (hereinafter referred to as the (C-1) component) and the following general formula (2). And diisocyanate adduct (C-2) (hereinafter referred to as (C-2) component).

(In the formula, R ¹ represents any of an aromatic diisocyanate residue, an aliphatic diisocyanate residue, and an alicyclic diisocyanate residue.)

(In the formula, R ² represents an alkyl group having 1 to 3 carbon atoms or a functional group represented by OCN—R ³ —HN—C (═O) —O—CH ₂ —. Also, in the formula and in R ²⁾ And R ³ each independently represents an aromatic diisocyanate residue, an aliphatic diisocyanate residue, or an alicyclic diisocyanate residue.)

  The “diisocyanate residue” means the remaining group excluding the isocyanate group in the aromatic diisocyanate, aliphatic diisocyanate, and alicyclic diisocyanate constituting the component (C-1) or component (C-2). means.

  Examples of the aromatic diisocyanate include tolylene diisocyanate, α, α, α ′, α′-tetramethylxylylene diisocyanate, diphenylmethane diisocyanate, naphthalene diisocyanate, xylylene diisocyanate, and the like. Examples of the aliphatic diisocyanate include hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and lysine diisocyanate. Examples of the alicyclic diisocyanate include dicyclohexylmethane diisocyanate, isophorone diisocyanate, 1,4-cyclohexane diisocyanate, hydrogenated xylene diisocyanate, and hydrogenated tolylene diisocyanate.

  Examples of commercially available products of component (C) include Coronate 2030, Coronate L, Coronate HX (all manufactured by Nippon Polyurethane Industry Co., Ltd.), Coronate HL (manufactured by Nippon Polyurethane Industry Co., Ltd.), Takenate D110N (Mitsui Chemicals). Etc.).

  Further, as the component (C) other than the components (C-1) and (C-2) (hereinafter referred to as the component (C-3)), for example, burette type polyisocyanate, lysine triisocyanate, hexafunctional polyisocyanate, and the like. Isocyanate (product name “Duranate MHG-80B”, manufactured by Asahi Kasei Chemicals Corporation) and the like can also be used.

  The component (C) is preferably in the order of the component (C-1), the component (C-2), and the component (C-3) from the viewpoints of drying property, adhesion, and moisture resistance of the undercoat layer. In addition, you may use the said aromatic diisocyanate, aliphatic diisocyanate, and alicyclic diisocyanate as a dilution component with (C) component.

  The undercoat agent of the present invention includes various known urethanization catalysts (D) (hereinafter referred to as the component (D)) for the purpose of enhancing the curability of the undercoat agent and obtaining the undercoat layer in a shorter time. Can be made. Specific examples of the component (D) include organometallic catalysts such as dibutyltin dilaurate, dioctyltin dilaurate, and bismuth octylate, and amine catalysts such as organic amines such as triethylamine and triethylenediamine, and salts thereof.

  The undercoat agent of the present invention is usually used as a solution of various known organic solvents (E) (hereinafter referred to as component (E)). Specific examples of component (E) include ketone organic solvents [acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.], ester organic solvents [methyl acetate, ethyl acetate, isopropyl acetate, butyl acetate, amyl acetate, ethyl formate. Butyl propionate, methoxypropyl acetate, methyl cellosolve acetate, cellosolve acetate, etc.], ether organic solvents (dioxane, diethyl ether, tetrahydrofuran, etc.), aprotic polar organic solvents [N-methylpyrrolidone, dimethylformamide, dimethylacetamide, etc. ], Aromatic hydrocarbon-based organic solvents [Solvesso # 100, Solvesso # 150 (all manufactured by Exxon Chemical Co., Ltd.), toluene, xylene, etc.]. Among these, the use of a ketone-based organic solvent can prolong the pot life of the undercoat agent, improve the drying properties of the undercoat layer, and provide a cured film with excellent adhesion and moisture resistance for a relatively short time. It is preferable because it can be formed.

  The content of the component (A) and the component (B) in the undercoat agent of the present invention is not particularly limited, but from the viewpoints of adhesion and moisture resistance, both components are 100 parts by weight of the component (A) (in terms of nonvolatile content) The content of the component (B) with respect to) is usually about 0.5 to 30 parts by weight, preferably 1 to 10 parts by weight.

  The content of the component (C) is such that z / (x + y) is usually 0.00 when the hydroxyl group of the component (A) is xmol, the hydroxyl group of the component (B) is ymol, and the isocyanate group of the component (C) is zmol. It is good to be in the range of about 5 to 5, especially 1.0 to 3.0. By being in this range, the curability, adhesion, moisture resistance and the like of the undercoat agent are particularly good.

  (D) Content of component is about 0.1-5 weight part normally with respect to 100 weight part (solid content conversion) of (A) component, Preferably it is 0.3-3 weight part. By being the said content, sclerosis | hardenability, adhesiveness, moisture resistance, etc. of an undercoat agent become especially favorable.

  Although the usage-amount of (E) component is not specifically limited, What is necessary is just the range from which the non-volatile matter density | concentration of an undercoat agent is about 10 to 50 weight% normally, Preferably it is 20 to 40 weight%.

  Further, in the undercoat agent of the present invention, leveling agents, anti-slip agents, antioxidants, pigments, dyes, lubricants, inorganic fillers (colloidal silica, zinc oxide, calcium carbonate, barium sulfate, titanium oxide, kaolin) , Aluminum hydroxide, etc.), light stabilizers, ultraviolet absorbers, photopolymerization initiators described later, and the like.

  The plastic film with an active energy ray cured film of the present invention (hereinafter sometimes simply referred to as a laminated film) includes an undercoat layer comprising the undercoat agent of the present invention on at least one surface of the plastic film, and an active energy ray cured film layer. Are stacked in this order.

  Examples of the plastic film include a film made of a thermoplastic resin such as a polystyrene film, a polycarbonate film, a polyester film, an ABS film, a polyvinyl chloride film, a polyolefin film, and a triacetyl cellulose film. It may be processed. Among these, a polyester film, particularly a polyethylene terephthalate (PET) film is preferable from the viewpoints of adhesion and moisture resistance.

The undercoat layer is obtained by applying the undercoat agent of the present invention to the plastic film and drying it. Examples of the coating means include a roll coater, a reverse roll coater, a gravure coater, a knife coater, and a bar coater. The coating amount is usually about 0.01 to 10 g / m ² as a dry nonvolatile content. The film thickness is not particularly limited, but is usually about 0.1 to 10 μm. The drying temperature is usually from room temperature to 150 ° C., specifically from room temperature to 120 ° C., and the drying time is usually from about 10 seconds to 3 minutes.

  The active energy ray-cured coating layer is obtained by applying various known active energy ray-curable materials on the undercoat layer by the above means and irradiating the active energy rays. The film thickness of the cured film layer is not particularly limited, but is usually about 1 to 75 μm.

  The active energy ray curable material may be any of a monomer type, an oligomer type, and a polymer type. Specifically, the component (B); the component (b2); 2-ethylhexyl (meth) acrylate, isodecyl (meth) acrylate, isooctyl (meth) acrylate, benzyl (meth) acrylate, cyclopentanyl (meth) acrylate , Mono (meth) acrylates such as cyclohexyl (meth) acrylate, dicyclopentenyl (meth) acrylate, and isobornyl (meth) acrylate; 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) ) Diacrylates such as acrylate, 1,6-hexanediol di (meth) acrylate, diethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate; trimethylolpropane tri (meth) acrylate, Tylene oxide modified trimethylolpropane tri (meth) acrylate, propylene oxide modified trimethylolpropane tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, glycerol tri (meth) acrylate, etc. , Compounds having at least three (meth) acryloyl groups; oligomers such as polyurethane poly (meth) acrylate and polyester poly (meth) acrylate, and the like may be used in combination of two or more.

  The active energy ray-curable material may contain various known photopolymerization initiators. Specifically, benzophenone-based polymerization initiators such as benzophenone, benzoylbenzoic acid, p-dimethylaminobenzoic acid ester, methyl benzoylbenzoate, phenylbenzophenone, trimethylbenzophenone, hydroxybenzophenone; phenoxydichloroacetophenone, butyldichloroacetophenone, diethoxy Acetophenone polymerization initiators such as acetophenone, hydroxymethylphenylpropanone, isopropylphenylhydroxymethylpropanone, hydroxycyclohexylphenylketone; thioxanthone such as thioxanthone, chlorothioxanthone, methylthioxanthone, isopropylthioxanthone, dichlorothioxanthone, diethylthioxanthone, diisopropylthioxanthone Polymerization initiators Gerare, it may be used in combination of two or more thereof.

  In addition, the said active energy ray hardening-type material may mix | blend the said (E) component and additive.

Examples of the active energy rays include ultraviolet rays and electron beams. Examples of the ultraviolet light source include a high-pressure mercury lamp and a metal halide lamp, and the irradiation amount is usually about 100 to 2,000 mJ / cm ² . Examples of the electron beam supply method include scanning electron beam irradiation and curtain electron beam irradiation methods, and the irradiation energy is usually about 10 to 200 kGy.

  EXAMPLES Hereinafter, although an Example and a comparative example are given and this invention is demonstrated in detail, this invention is not limited to these. In each example, parts and% are based on weight unless otherwise specified.

Production Example 1
<Manufacture of (A) component>
In a reaction vessel equipped with a stirrer, a cooler, a thermometer and a nitrogen gas introduction tube, 479 parts of terephthalic acid, 402 parts of isophthalic acid, 87 parts of azelaic acid, 256 parts of ethylene glycol, 221 parts of 1,6-hexanediol, neo 148 parts of pentyl glycol and 7 parts of trimethylolpropane were charged, and the reaction system was heated under stirring to melt them. Next, while removing water produced by the dehydration condensation reaction, the reaction system was gradually heated from 160 ° C. to 200 ° C. over 3 hours, and further kept at 200 ° C. for 1 hour. Next, 0.16 part of antimony trioxide was added. Next, a vacuum decompression apparatus was connected to the reaction vessel, and a reduced pressure polycondensation reaction was performed at 235 ° C. and 2.8 kPa for 1 hour. Next, 512 parts of methyl isobutyl ketone and 768 parts of methyl ethyl ketone were added and dissolved uniformly. Thus, the non-volatile content is 50%, the hydroxyl value is 21 mgKOH / g, and the measured value is based on the glass transition temperature (product name “DSC6200” manufactured by Seiko Instruments Inc.). The same applies hereinafter. ) Is a polyester resin having a number average molecular weight of 31 ° C. and a number average molecular weight (gel permeation chromatography apparatus (product name “HLC-8220GPC”: manufactured by Tosoh Corporation) converted to polystyrene. The same applies hereinafter.) A solution of A-1) was obtained.

Production Examples 2 to 11, Comparative Production Example 1
Each of the branched polyester resins (A-2) to (A-11) is the same as in Production Example 1 except that the types and amounts used of the components (a1) to (a3) are changed to those shown in Table 1. A solution and a solution of unbranched polyester resin (A-12) were obtained. In addition, the unit of the usage-amount of each component in Table 1 is a part.

In Table 1, each symbol has the following meaning.
TPA: terephthalic acid IPA: isophthalic acid AZE: azelaic acid SEB: sebacic acid HHPA: hexahydrophthalic anhydride CHDA: 1,4-cyclohexanedicarboxylic acid EG: ethylene glycol 1,6HD: 1,6 hexanediol NPG: neopentyl glycol PG : Propylene glycol 2MPD: 2-methyl 1,3-propanediol 1,4BD: 1,4-butanediol DEG: Diethylene glycol CHDM: 1,4-cyclohexanedimethanol BisAEO adduct: Ethylene oxide adduct of bisphenol A GLY: Glycerin TMP : Trimethylolpropane OHV: Hydroxyl value (mgKOH / g)
Tg: Glass transition temperature (° C)
Mn: Number average molecular weight

<Preparation of undercoat agent>
Example 1
To 100 parts of the solution of the branched polyester resin (A-1) obtained in Production Example 1, pentaerythritol triacrylate (trade name “Biscoat # 300”: Osaka Organic Chemical Industry Co., Ltd.) is added as a component (B). 5 parts were added and mixed. Next, 8.9 parts of “coronate HX” (hexamethylene diisocyanate nurate (trade name: Nippon Polyurethane Industry Co., Ltd.) as component (C) and dioctyltin dilaurate (trade name “ Neostan U-810 ": Nitto Kasei Co., Ltd.) was added in an amount of 0.25 part, and diluted with 131 parts of methyl ethyl ketone as component (E) to obtain an undercoat agent having a nonvolatile content of 25%.

Examples 2 to 26, Comparative Examples 1 to 5
An undercoat agent was obtained in the same manner as in Example 1 except that the raw material type and amount used shown in Table 2 were changed (the non-volatile content of any undercoat agent was 25%).

<Preparation of active energy ray-curable resin composition>
100 parts of tripropylene glycol diacrylate (trade name “TPGDA”: manufactured by Daicel Cytec Co., Ltd.) and 5 parts of photoinitiator (trade name “Irgacure 184”: manufactured by Ciba Japan Co., Ltd.) are mixed well, and ultraviolet rays are mixed. A curable resin composition was prepared.

<Production of laminated film>
The undercoat agent of Example 1 was applied to a commercially available PET film (trade name “Lumirror T60”, 75 μm thickness, manufactured by Toray Industries, Inc.) with a bar coater so that the dry film thickness was 1 μm, and at 120 ° C. for 30 seconds. After drying, the UV curable resin composition was immediately applied to the undercoat surface with a bar coater so that the film thickness after curing was 10 μm. Next, a laminated film was produced by passing the coated film three times under high pressure mercury lamp (80 W, mercury lamp height 10 cm, transport speed 10 m / min) in the atmosphere. A laminated film was prepared in the same manner for the undercoat agents of other examples and comparative examples.

<Initial adhesion>
In accordance with JIS 5600, a 1 mm square was formed on the laminated film of Example 1 in a grid pattern, and then an adhesive tape was applied and rapidly peeled off in the vertical direction. Next, the initial adhesion was evaluated according to the following criteria based on the remaining amount of the cured film. The laminated films of other examples and comparative examples were similarly evaluated. These results are shown in Table 2.
6:90 mass or more remained.
5: 80 squares or more and less than 90 squares remained.
4: 70 squares or more and less than 80 squares remained.
3: More than 60 squares and less than 70 squares remained.
2: More than 50 cells and less than 60 cells remained.
Less than 1:50 mass remained.

<Moisture resistance>
After the laminated film according to Example 1 was left in a constant temperature and humidity chamber (60 ° C., 95% RH) for 4 days, the adhesiveness of the cured film was evaluated by the same method and standard as the initial adhesiveness evaluation.
These results are shown in Table 2.

In Table 2, each symbol has the following meaning.
M400: Dipentaerythritol pentaacrylate and hexaacrylate (trade name “Aronix M-400” manufactured by Toagosei Co., Ltd.)
V295: Trimethylolpropane triacrylate (trade name “Biscoat # 295” manufactured by Osaka Organic Chemical Industry Co., Ltd.)
D110N: Commercially available isocyanate-based crosslinking agent (trimethylolpropane xylene diisocyanate): trade name “Takenate D110N”: manufactured by Mitsui Chemicals, Inc.
U600: Bismuth octylate (trade name “Neostan U-600” manufactured by Nitto Kasei Co., Ltd.)
In Table 2, (* 1) and (* 2) are comparative examples not corresponding to the component (A) and the component (B) of the present invention, respectively.

Claims (11)

Branched polyester resin having a hydroxyl group (A), it contains a compound having an active energy ray polymerizable functional group and a hydroxyl group (B) and an isocyanate group at least three with polyisocyanate (C), and component (B) At least one monohydroxy poly (meth) acrylate selected from the group consisting of trimethylolpropane di (meth) acrylate, glycerin di (meth) acrylate, dipentaerythritol penta (meth) acrylate and pentaerythritol tri (meth) acrylate (B-2) and / or at least one polyhydroxy poly (meth) acrylate (B-3) selected from the group consisting of pentaerythritol di (meth) acrylate and dipentaerythritol tetra (meth) acrylate. DOO characterized nonaqueous undercoating formulation for plastic film with an active energy ray-curable coating. The undercoat agent according to claim 1, wherein the component (A) is a dehydration condensate composed of dicarboxylic acids (a1), diols (a2), and triols (a3). The undercoat agent according to claim 1 or 2, wherein the component (a1) contains an aromatic dicarboxylic acid. (A) The undercoat agent in any one of Claims 1-3 whose hydroxyl value of a component is 10-40 mgKOH / g. (A) The undercoat agent in any one of Claims 1-4 whose glass transition temperature of a component is 0-60 degreeC. The number average molecular weight of (A) component is 5,000-22,000, The undercoat agent in any one of Claims 1-5. Furthermore, the undercoat agent in any one of Claims 1-6 containing a urethanization catalyst (D). (1) z / (x + y) is 0.5 to 5 when the hydroxyl group of component (A) is xmol, the hydroxyl group of component (B) is ymol, and the isocyanate group of component (C) is zmol. 7. Any undercoat agent according to 7 . The undercoat agent of Claim 7 or 8 whose content of (D) component is 0.1-5 weight part with respect to 100 weight part (nonvolatile matter conversion) of (A) component. A plastic film with an active energy ray-cured film, wherein the undercoat layer comprising the undercoat agent according to any one of claims 1 to 9 and the active energy ray-cured film layer are laminated in this order on at least one surface of the plastic film. Plastic film is a polyester film, a plastic film with an active energy ray-curable coating of claim 1 0.