JP2020164554A - Coating agent, and laminate, packaging material and processed product coated therewith - Google Patents

Abstract

To provide a coating agent that is a thin film but is excellent; can be easily formed with a simple device, and can impart water vapor barrier properties, and provide a laminate, a packaging material, and a processed product obtained by using the coating agent and having excellent water vapor barrier properties.SOLUTION: The present invention provides a two-liquid type coating composition containing an acid group-containing olefin resin (A1), an isocyanate compound (B1), and an organic solvent, a laminate coated with the coating agent, a packaging material including the laminate coated with the coating agent, and a processed product.SELECTED DRAWING: None

Description

The present invention relates to a coating agent capable of imparting excellent water vapor barrier properties, and a water vapor barrier laminate, packaging material, and processed product coated with the coating agent.

Packaging containers for containing various foods, chemicals, etc. are manufactured by molding or molding a thermoplastic resin film such as polyethylene terephthalate (PET), nylon (Ny), polypropylene (PP), or paper. When packing products that dislike moisture in these packaging containers, it is necessary to apply a moisture-proof treatment.

As a moisture-proof processing method, there are a method of melting a moisture-proof material and laminating it on a base material, and a method of applying (or impregnating) a coating liquid containing the moisture-proof material, but thinning is possible and handling. The latter is more advantageous because it is easy to use. As a material having moisture resistance, those described in Patent Documents 1 to 3 are known.

JP-A-9-316252 Japanese Unexamined Patent Publication No. 2003-96689 Japanese Patent Application Laid-Open No. 10-53996

However, the inventions described in Patent Documents 1 to 3 are not sufficiently moisture-proof, and in Patent Documents 1 and 2, the resin composition must be heated to a temperature equal to or higher than the melting point for coating on the substrate. , Special coating equipment and complicated coating process were required.

The present invention has been made in view of such a situation, and relates to a coating agent capable of imparting excellent water vapor barrier properties, and a laminate, a packaging material, and a processed product coated with the coating agent.

The present invention relates to a two-component coating agent containing an acid group-containing olefin resin (A1), an isocyanate compound (B1), and an organic solvent.

According to the coating agent of the present invention, a coating layer which is a thin film but has excellent water vapor barrier properties can be easily formed by a simple device. In addition, the laminate, packaging material, and processed product coated with this coating agent have excellent water vapor barrier properties.

<Coating agent>
The coating agent of the present invention is a two-component coating agent composed of a first agent containing an acid group-containing olefin resin (A1) and a second agent containing an isocyanate compound (B1). Hereinafter, each component of the agent of the present invention will be described in detail.

(1st agent)
The first agent contains an acid group-containing olefin resin (A1) as the resin (A). Examples of the acid group contained in the acid group-containing olefin resin (A1) include a carboxyl group, an anhydrous carboxylic acid group, a sulfonic acid group, and a phosphoric acid group. The acid group-containing resin may include only one of these, or may include two or more of them.

Examples of the acid group-containing olefin resin include homopolymers or copolymers of acid group-containing monomers, copolymers of acid group-containing monomers and olefin-based monomers, and modified acid group-containing monomers of polyolefins.

As the acid group-containing monomer used for preparing the homopolymer or copolymer of the acid group-containing monomer, ethylenically unsaturated carboxylic acid or ethylenically unsaturated carboxylic acid anhydride is preferable. Specifically, acrylic acid, methacrylic acid, maleic acid, itaconic acid, citraconic acid, mesaconic acid, maleic anhydride, 4-methylcyclohexe-4-ene-1,2-dicarboxylic acid anhydride, bicyclo [2. 2.2] Oct-5-ene-2,3-dicarboxylic acid anhydride, 1,2,3,4,5,8,9,10-octahydronaphthalene-2,3-dicarboxylic acid anhydride, 2- Octa-1,3-diketospiro [4.4] non-7-ene, bicyclo [2.2.1] hept-5-ene-2,3-dicarboxylic acid anhydride, maleopimalic acid, tetrahydrophthalic acid anhydride, Methyl-bicyclo [2.2.1] Hept-5-ene-2,3-dicarboxylic acid anhydride, Methyl-norbornene-5-ene-2,3-dicarboxylic acid anhydride, Norborn-5-ene-2, Examples thereof include 3-dicarboxylic acid anhydride.

The acid group-containing monomer used for preparing the copolymer of the acid group-containing monomer and the olefin-based monomer is the same as the above-mentioned homopolymer of the acid group-containing monomer or the acid group-containing monomer used for preparing the copolymer. Can be used. It may be used alone or in combination of two or more. It is preferable to use maleic anhydride.

Examples of the olefin-based monomer used for preparing the copolymer of the acid group-containing monomer and the olefin-based monomer include olefins having 2 to 8 carbon atoms, such as ethylene, propylene, isobutylene, 1-butene, and 4-methyl-. Examples thereof include 1-pentene, hexene and vinylcyclohexane. Among these, olefins having 3 to 8 carbon atoms are preferable, propylene and 1-butene are more preferable, and propylene and 1 are particularly preferable, because they have good adhesion to a resin film and solvent resistance, which will be described later. -It is preferable to use it in combination with butene because it has excellent resistance to solvents and adhesion to the substrate.

In order to prepare the copolymer of the acid group-containing monomer and the olefin-based monomer, in addition to the acid group-containing monomer and the olefin-based monomer described above, other compounds having an ethylenically unsaturated group such as styrene, butadiene, isoprene and the like are used. It may be used together.

As the acid group-containing monomer used for preparing the modified acid group-containing monomer of polyolefin, the same as the above-mentioned homopolymer of the acid group-containing monomer or the same acid group-containing monomer used for preparing the copolymer should be used. Can be done. It may be used alone or in combination of two or more. It is preferable to use maleic anhydride.

Examples of the polyolefin used for preparing the acid group-containing monomer modified product of polyolefin include homopolymers and copolymers of olefins having 2 to 8 carbon atoms, and copolymers of olefins having 2 to 8 carbon atoms and other monomers. Examples thereof include high-density polyethylene (HDPE), low-density polyethylene (LDPE), and polyethylene such as linear low-density polyethylene resin, polypropylene, polyisobutylene, poly (1-butene), and poly (4-methyl-). 1-pentene), polyvinylcyclohexane, ethylene / propylene block copolymer, ethylene / propylene random copolymer, ethylene / 1-butene copolymer, ethylene / 4-methyl-1-pentene copolymer, ethylene / hexene Copolymers, α-olefin copolymers such as propylene / 1-butene copolymers, ethylene / vinyl acetate copolymers, ethylene / methyl methacrylate copolymers, ethylene / vinyl acetate / methyl methacrylate copolymers, ionomer resins And so on. Among these, a homopolymer of an olefin having 3 to 8 carbon atoms and two or more copolymers of an olefin having 3 to 8 carbon atoms are preferable from the viewpoint of particularly good adhesion, and propylene alone. A polymer or a propylene / 1-butene copolymer is more preferable, and a propylene / 1-butene copolymer is particularly preferable because it has excellent resistance to a solvent and excellent adhesion.

Examples of the method for modifying polyolefin with an acid group-containing monomer include graft modification and copolymerization. To react an acid group-containing monomer with a polyolefin by graft modification, specifically, a method of melting the polyolefin and adding an acid group-containing monomer (graft monomer) to the polyolefin for a graft reaction, or dissolving the polyolefin in a solvent. A method of making a solution by adding a graft monomer to the graft reaction, mixing the polyolefin dissolved in an organic solvent and the graft monomer, heating at a temperature higher than the softening temperature of the polyolefin or the melting point, and radical polymerization in a molten state. And a method of simultaneously performing the hydrogen abstraction reaction and the like.

In either case, in order to efficiently carry out the graft copolymerization of the graft monomer, it is preferable to carry out the graft reaction in the presence of a radical initiator. The graft reaction is usually carried out under the condition of 60 to 350 ° C. The ratio of the radical initiator used is usually in the range of 0.001 to 1 part by weight with respect to 100 parts by weight of the polyolefin before modification.

The weight average molecular weight of the acid group-containing olefin resin is preferably 40,000 or more in order to improve the adhesion. Further, in order to ensure appropriate fluidity, the weight average molecular weight of the acid group-containing olefin resin is preferably 150,000 or less.

In the present invention, the weight average molecular weight (Mw) and the number average molecular weight (Mn) are values measured by gel permeation chromatography (GPC) under the following conditions.

Measuring device; HLC-8320GPC manufactured by Tosoh Corporation
Column; TSKgel 4000HXL, TSKgel 3000HXL, TSKgel 2000HXL, TSKgel 1000HXL manufactured by Tosoh Corporation
Detector; RI (Differential Refractometer)
Data processing; Multi-station GPC-8020modelII manufactured by Tosoh Corporation
Measurement conditions; column temperature 40 ° C
Solvent tetrahydrofuran
Flow velocity 0.35 ml / min Standard; Monodisperse polystyrene sample; 0.2 mass% tetrahydrofuran solution in terms of resin solid content filtered through a microfilter (100 μl)

The acid group-containing olefin resin is preferably crystalline. The melting point of the acid group-containing olefin resin is preferably 50 ° C. or higher, more preferably 60 ° C. or higher, and even more preferably 65 ° C. or higher. The melting point of the acid group-containing olefin resin is preferably 120 ° C. or lower, more preferably 100 ° C. or lower, and even more preferably 90 ° C. or lower.

The melting point of the acid group-containing olefin resin is measured by DSC (Differential Scanning Calorimetry). Specifically, after raising the temperature from the temperature at which the temperature falls to the temperature at which the temperature rises at 10 ° C / min, the temperature is cooled to the temperature at which the temperature falls at 10 ° C./min to remove the heat history, and then the temperature rises again at 10 ° C. The temperature rises to the point. The melting point is the peak temperature when the temperature is raised for the second time. Further, the temperature at which the temperature falls is set to a temperature 50 ° C. or higher lower than the crystallization temperature, and the temperature at which the temperature rises is reached is set to a temperature about 30 ° C. or higher higher than the melting point temperature. The temperature at which the temperature falls and the temperature at which the temperature rises rise are determined by trial measurement.

Specific examples of such an acid group-containing olefin resin include maleic anhydride-modified polypropylene, ethylene- (meth) acrylic acid copolymer, ethylene- (meth) acrylate-maleic anhydride ternary copolymer and the like. .. Commercially available acid group-containing olefin resins include "Modic" series manufactured by Mitsubishi Chemicals, Inc., "Admer" series, "Unistor" series, and "Toyo Tuck" series manufactured by Toyobo Co., Ltd. "Umex" series manufactured by Sanyo Kasei Co., Ltd., "Lexpearl EAA" series manufactured by Nippon Polyethylene Co., Ltd., "Lexpearl ET" series, "Primacol" series manufactured by Dow Chemicals Co., Ltd., Mitsui Dupont Polychemical Co., Ltd. Examples include the "Nucrel" series and the "Bondain" series made by Alchema.

As the acid group-containing olefin resin (A1), those other than those described above can be used, and examples thereof include Tough Tech M series manufactured by Asahi Kasei Corporation and Kraton FG series manufactured by Kraton Polymer Japan Co., Ltd.

The first agent may contain, as the resin (A), a resin (A2) having no reactive functional group in addition to the acid group-containing olefin resin (A1). The resin (A2) is preferably a crystalline olefin resin. When the resin (A2) is a crystalline olefin resin, the solvent resistance of the coating agent is improved.

Examples of the resin (A2) include homopolymers and copolymers of olefins having 2 to 8 carbon atoms, such as ethylene, propylene, isobutylene, 1-butene, 4-methyl-1-pentene, hexene, and vinylcyclohexane. Examples thereof include copolymers of olefins having 2 to 8 carbon atoms and other monomers. Specific examples thereof include high-density polyethylene (HDPE), low-density polyethylene (LDPE), and linear low-density polyethylene resin. Polyethylene, polypropylene, polyisobutylene, poly (1-butene), poly (4-methyl-1-pentene), polyvinylcyclohexane, ethylene / propylene block copolymer, ethylene / propylene random copolymer, ethylene / 1-butene Copolymers, α-olefin copolymers such as ethylene / 4-methyl-1-pentene copolymers, ethylene / hexene copolymers, ethylene / methyl methacrylate copolymers, propylene / 1-butene copolymers, etc. Can be mentioned. Among these, a homopolymer of an olefin having 3 to 8 carbon atoms and a copolymer of two or more kinds of olefins having 3 to 8 carbon atoms are preferable from the viewpoint of particularly good solvent resistance, and propylene is preferable. A homopolymer or copolymer is more preferable, and a propylene homopolymer is more preferable.

The resin (A2) is highly soluble in a solvent and has improved coatability. Therefore, the weight average molecular weight is preferably 2000 to 200,000. The weight average molecular weight of the resin (A2) is more preferably 20,000 to 180,000, and even more preferably 40,000 to 160,000.

The melting point of the resin (A2) is preferably 50 ° C to 100 ° C. When the melting point is 50 ° C. or higher, the electrolytic resistance can be improved more reliably, and when the melting point is 100 ° C. or lower, the coatability can be kept good. The melting point of the resin (A2) is more preferably 60 to 95 ° C, more preferably 70 to 90 ° C.

The solid content acid value of the first agent is preferably 1 mgKOH / g or more, more preferably 5 mgKOH / g or more, preferably 200 mgKOH / g or less, and more preferably 165 mgKOH / g or less. preferable. If it is 200 mgKOH / g or less, the flexibility is excellent, and if it is 1 mgKOH / g or more, the heat resistance is good.

The acid value of the first agent is a coefficient (f) obtained from a calibration curve prepared by using FT-IR (FT-IR4200 manufactured by JASCO Corporation) and a chloroform solution of maleic anhydride, and a maleic anhydride-modified polyolefin. It can be calculated by the following formula using the absorbance (I) of the expansion and contraction peak (1780 cm ^-1 ) of the anhydrous ring of maleic anhydride and the absorbance (II) of the expansion and contraction peak (1720 cm ^-1 ) of the carbonyl group of maleic anhydride in the solution. it can. In the following formula, maleic anhydride has a molecular weight of 98.06 and potassium hydroxide has a molecular weight of 56.11.

(Second agent)
The second agent contains an isocyanate compound (B1) as a so-called curing agent (B) having reactivity with the acid group-containing olefin resin (A1). The isocyanate compound (B1) is not particularly limited as long as it has a plurality of isocyanate groups in one molecule, and conventionally known compounds can be used. Specific examples include butane-1,4-diisocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethyl hexamethylene diisocyanate, and 2,4,4-trimethyl. Hexamethylene diisocyanate, 1,3,6-hexamethylene triisocyanate, octamethylene diisocyanate, 1,8-diisocyanate-4-isocyanate methyloctane, 1,6,11-undecantryisocyanate, xylylene diisocyanate, m-tetramethylxyli Aliphatic diisocyanates such as range isocyanate, lysine diisocyanate, lysine ester triisocyanate

Cyclohexane-1,4-diisocyanate, isophorone diisocyanate, dicyclohexylmethane-4,4'-diisocyanate, 1,3-bis (isocyanatemethyl) cyclohexane, methylcyclohexanediisocyanate, isopropyridene dicyclohexyl-4,4'-diisocyanate, norbornane diisocyanate, etc. Alicyclic diisocyanate,

1,5-naphthylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-diphenyldimethylmethane diisocyanate, 4,4'-dibenzyl diisocyanate, dialkyldiphenylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanate, 1,3-phenylenediocyanate , 1,4-phenylenediocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate and other aromatic diisocyanates.

Compounds derived from these, that is, isocyanurates, adducts, biuret types, uretdiones, allophanates, prepolymers having isocyanate residues (low polymers obtained from diisocyanates and polyols), or these. A complex or the like can also be used.

A compound obtained by reacting a part of the isocyanate groups of the above-mentioned polyfunctional isocyanate compound with a compound having reactivity with the isocyanate groups may be used as the curing agent (B). Compounds that have reactivity with isocyanate groups include amino group-containing compounds such as butylamine, hexylamine, octylamine, 2-ethylhexylamine, dibutylamine, ethylenediamine, benzylamine, and aniline: methanol, ethanol, propanol, and isopropanol. , Butanol, Hexanol, Octanol, 2-ethylhexyl alcohol, dodecyl alcohol, ethylene glycol, propylene glycol, benzyl alcohol, phenol and other compounds containing hydroxyl groups: allyl glycidyl ether, 2-ethylhexyl glycidyl ether, phenyl glycidyl ether, neopentyl Compounds having epoxy groups such as glycol diglycidyl ether, 1,6-hexanediol glycidyl ether, cyclohexanedimethanol diglycidyl ether: acetic acid, butanoic acid, hexanoic acid, octanoic acid, succinic acid, adipic acid, sebacic acid, phthal Examples thereof include compounds containing carboxylic acids such as acids.

Among them, it is preferable to use a compound derived from an aliphatic isocyanate such as isophorone diisocyanate or hexamethylene diisocyanate or an aliphatic isocyanate because it is excellent in storage stability and adhesion to a base material. It is preferable that 90% or more of the isocyanate compound (B1) is an aliphatic isocyanate or a compound derived from an aliphatic isocyanate. The total amount of the isocyanate compound (B1) may be an aliphatic isocyanate compound or a compound derived from the aliphatic isocyanate compound.

The second agent may contain a compound (B2) having reactivity with the acid group-containing olefin resin (A1) described later in addition to the isocyanate compound (B1), but even in that case, the isocyanate compound occupying the curing agent (B). The ratio of (B1) is preferably 40% or more. The ratio of the isocyanate compound (B1) to the curing agent (B) is more preferably 50% or more, and more preferably 80% or more. The total amount of the curing agent (B) may be the isocyanate compound (B1).

As the second agent, a compound (B2) having reactivity with the acid group-containing olefin resin (A1) other than the isocyanate compound (B1) may be used in combination. Examples of the other compound (B2) that can be used in combination with the isocyanate compound (B1) include an epoxy compound, an aziridine group-containing compound, a carbodiimide, an oxazoline, and an amino resin.

As the epoxy compound, polypolypoly of an aliphatic polyol such as ethylene glycol, propylene glycol, hexanediol, neopentyl glycol, trimethylolethane, trimethylolpropane, pentaerythritol, glycerin, diglycerin, sorbitol, spiroglycol or hydrogenated bisphenol A. Glyceridyl ether type epoxy resin;
Bisphenol type epoxy resin such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AD type epoxy resin;
Aromatic epoxy resins such as phenol novolac resin and novolac type epoxy resin which is glycidyl ale of cresol novolak resin;
Ethylene oxide of aromatic polyhydroxy compounds such as bisphenol A, bisphenol F, bisphenol S, bisphenol AD, or polyglycidyl ether of polyol which is an adduct of propylene oxide;
Polyglycidyl ether type epoxy resin of polyether polyol such as polyethylene glycol, polypropylene glycol or polytetramethylene glycol; bis (3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxycyclohexylmethyl-3', 4'-epoxy Cyclic aliphatic polyepoxy resin such as cyclohexylcarboxylate;
Polyglycidyl ester type epoxy resin of polycarboxylic acid such as propanetricarboxylic acid, butanetetracarboxylic acid, adipic acid, phthalic acid, terephthalic acid or trimellitic acid;
Hydrocarbon diene bisepoxy resins such as butadiene, hexadiene, octadiene, dodecadien, cyclooctadiene, α-pinene or vinylcyclohexene;
Diene polymer epoxy resin such as polybutadiene or polyisoprene;
Glycidylamine type epoxy resins such as tetraglycidyldiaminodiphenylmethane, triglycidylparaaminophenol, tetraglycidylbisaminomethylcyclohexane, diglycidylaniline, and tetraglycidylmethoxylylenediamine;
Epoxy resins containing a heterocycle such as triazine and hydantoin can be mentioned.
These epoxy resins may be used alone or in combination of two or more.

The epoxy compound (B1) is preferably an epoxy compound having two or more epoxy groups and one or more hydroxyl groups in one molecule and having a weight average molecular weight of 3000 or less.

Examples of the aziridine group-containing compound include N, N'-hexamethylene-1,6-bis (1-aziridinecarboxyamide) and N, N'-diphenylmethane-4,4'-bis (1-aziridinecarboxyamide). , Trimethylolpropan-tri-β-aziridinyl propionate), N, N'-toluene-2,4-bis (1-aziridinecarboxyamide), triethylenemelamine, trimethylalopropan-tri-β (2) -Methylaziridine) propionate, bisisophthaloyl-2-methylaziridine, tri-1-aziridinylphosphine oxide, tris-1--2-methylaziridinephosphine oxide and the like can be mentioned.

Examples of carbodiimides include N, N'-di-o-toluyl carbodiimide, N, N'-diphenylcarbodiimide, N, N'-di-2,6-dimethylphenylcarbodiimide, and N, N'-bis (2,6-bis). Diisopropylphenyl) carbodiimide, N, N'-dioctyldecylcarbodiimide, N-triyl-N'-cyclohexylcarbodiimide, N, N'-di-2,2-tert. -Butylphenylcarbodiimide, N-triyl-N'-phenylcarbodiimide, N, N'-di-p-aminophenylcarbodiimide, N, N'-di-p-hydroxyphenylcarbodiimide, N, N'-di-cyclohexylcarbodiimide , N, N'-di-p-toluyl carbodiimide and the like.

Examples of the oxazoline include monooxazoline compounds such as 2-oxazoline, 2-methyl-2-oxazoline, 2-phenyl-2-oxazoline, 2,5-dimethyl-2-oxazoline and 2,4-diphenyl-2-oxazoline, 2. , 2'-(1,3-phenylene) -bis (2-oxazoline), 2,2'-(1,2-ethylene) -bis (2-oxazoline), 2,2'-(1,4 butylene) -Bis (2-oxazoline), 2,2'-(1,4-phenylene) -bis (2-oxazoline) and the like can be mentioned.

Examples of the amino resin include melamine resin, benzoguanamine resin, urea resin and the like.

When the second agent contains a compound (B2) that is reactive with the acid group-containing olefin resin (A1), the blending amount thereof is preferably 60% or less of the curing agent (B), and is preferably 50% or less. Is preferable, and 20% or less is more preferable.

The blending amount of the curing agent (B) is adjusted within a range in which the solid content mass of the curing agent (B) / the solid content mass of the resin (A) contained in the first agent is 1/1 to 1/10. Is preferable.

The amount of the curing agent (B) to be blended is an equivalent ratio of the acid group (A) contained in the first agent to the functional group (B) having reactivity with the acid group contained in the curing agent (functional group (B). ) / Acid group (A)) is preferably adjusted in the range of 1 to 10. When the acid group (A) is an acid anhydride group, it is converted as 2 equivalents.

(Organic solvent)
The coating agent of the present invention can secure fluidity and exhibit appropriate coatability by further blending an organic solvent in addition to the above components. The organic solvent may be contained in only one of the first agent and the second agent, or both may be contained. It may be added when the first agent and the second agent are mixed. Such an organic solvent is not particularly limited as long as it can be volatilized and removed by overheating in the drying step at the time of coating the coating agent. For example, an aromatic organic solvent such as toluene or xylene; n-hexane, etc. Alicyclic organic solvents such as n-heptane; alicyclic organic solvents such as cyclohexane and methylcyclohexane; halogen-based organic solvents such as trichloroethylene, dichloroethylene, chlorobenzene and chloroform; ketone solvents such as methylethylketone, methylisobutylketone and cyclohexanone. Ester solvents such as ethyl acetate and butyl acetate; alcohol solvents such as ethanol, methanol, n-propanol, 2-propanol (isopropyl alcohol), butanol and hexanol; diisopropyl ether, butyl cellosolve, tetrahydrofuran, dioxane, butyl carbitol and the like Ether-based solvent; glycol ether-based solvent such as diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, propylene glycol monomethyl ether; glycol ester-based solvent such as ethylene glycol monomethyl ether acetate, proprene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate Solvents and the like may be mentioned, and these may be used alone or in combination of two or more.

Since the acid group-containing olefin resin (A1) is excellent in solubility, it is preferable to use a mixed solvent of an alicyclic organic solvent and an ester solvent, particularly a mixed solvent of methylcyclohexane and ethyl acetate. Further, in order to improve the solubility of the acid group-containing olefin resin (A1), a mixed solvent of an alicyclic organic solvent, an ester solvent and an alcohol solvent may be used. At this time, the alcohol solvent is preferably isopropyl alcohol, 2-butanol or the like.

Further, in order to improve the solubility of the isocyanate compound (B1), an aromatic organic solvent or a ketone solvent may be further used in combination with the mixed solvent of the alicyclic organic solvent and the ester solvent. At this time, toluene is preferably mentioned as the aromatic organic solvent, and methyl ethyl ketone is preferably mentioned as the ketone solvent.

The amount of the organic solvent used is preferably such that the ratio of the resin (A) to the total mass of the resin (A) and the organic solvent is 5 to 30% by mass. This makes it possible to obtain a coating agent having excellent coatability and wettability to a film.

(Other compounds)
The coating agent of the present invention includes acid anhydrides, curing accelerators, other resins (other than resin (A)), plasticizers, lubricants, blocking inhibitors, matting agents, thermoplastic elastomers, reactive elastomers, as required. Various additives such as a phosphoric acid compound and a silane coupling agent can be used. The content of these additives may be appropriately adjusted within a range that does not impair the function of the coating agent of the present invention.

Examples of the acid anhydride include cyclic aliphatic acid anhydride, aromatic acid anhydride, unsaturated carboxylic acid anhydride and the like, and one type or a combination of two or more types can be used. More specifically, for example, phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic acid anhydride, dodecenyl succinic anhydride, polyazipic acid anhydride, polyazereic acid anhydride, polysevacinic acid. Anhydrous, poly (ethyloctadecanedioic acid) anhydride, poly (phenylhexadecanedioic acid) anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, hexahydrophthalic anhydride , Methyl hymic acid anhydride, trialkyltetrahydrophthalic acid anhydride, methylcyclohexene dicarboxylic acid anhydride, methylcyclohexene tetracarboxylic acid anhydride, ethylene glycol bistrimericate dianhydride, het acid anhydride, nadic acid anhydride, Methylnadic acid anhydride, 5- (2,5-dioxotetrahydro-3-furanyl) -3-methyl-3-cyclohexane-1,2-dicarboxylic acid anhydride, 3,4-dicarboxy-1,2, Examples thereof include 3,4-tetrahydro-1-naphthalene succinic anhydride, 1-methyl-dicarboxy-1,2,3,4-tetrahydro-1-naphthalene succinic anhydride and the like.

Moreover, you may use the above-mentioned compound modified with glycol as an acid anhydride. Examples of glycols that can be used for modification include alkylene glycols such as ethylene glycol, propylene glycol and neopentyl glycol; and polyether glycols such as polyethylene glycol, polypropylene glycol and potitetramethylene ether glycol. Furthermore, copolymerized polyether glycols of two or more kinds of these glycols and / or polyether glycols can also be used.

The blending amount of the acid anhydride is preferably 0.01 part by mass or more, and more preferably 0.8 part by mass or more with respect to 100 parts by mass of the resin (A). The blending amount of the acid anhydride is preferably 10 parts by mass or less, more preferably 8 parts by mass or less, and 1.5 parts by mass or less with respect to 100 parts by mass of the resin (A). Is more preferable.

Examples of the curing accelerator include organic phosphine compounds such as tributylphosphine, methyldiphenylphosphine, triphenylphosphine, tris (4-methylphenyl) phosphine, tris (4-butylphenyl) phosphine, diphenylphosphine, and phenylphosphine, and 2-methylimidazole. , 1,2-Dimethylimidazole, 2-phenyl-4-methylimidazole, 2-ethyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole and other imidazoles. Compounds, triethylamine, triethylenediamine, N'-methyl-N- (2-dimethylaminoethyl) piperazin, 1,8-diazabicyclo [5.4.0] undecene (DBU), 1,5-diazabicyclo [4.3. 0] -Nonene, 6-dibutylamino-1,8-diazabicyclo [5.4.0] Undecene and other tertiary amines and these tertiary amines with phenol, octylic acid, quaternized tetraphenylborate salt, etc. Examples thereof include compounds converted into amine salts, cationic catalysts such as triallylsulfonium hexafluoroantimonate and diallyliodonium hexafluoroantimonate. These may be used alone or in combination of two or more. It is preferable to use at least one selected from the group consisting of organic phosphine compounds and imidazole compounds.

The amount of the curing accelerator to be blended is preferably 0.01 parts by mass or more and 5 parts by mass or less with respect to 100 parts by mass of the resin (A) of the first agent.

Examples of other resins include rosin-based or rosin ester-based resins, terpene-based or terpene phenol-based resins, saturated hydrocarbon resins, kumaron-based resins, kumaron inden-based resins, styrene-based resins, xylene-based resins, and phenol-based resins. , Petroleum-based resin and the like. Each of these may be used alone, or two or more types may be used in combination. Of these, it is preferable to use styrene resin.

The styrene resin is a homopolymer of a styrene-based monomer such as a homopolymer of styrene or a homopolymer of α-methylstyrene; a copolymer of styrene and α-methylstyrene; a styrene-based polymer such as styrene and α-methylstyrene. A copolymer of a monomer and a polymerizable aliphatic monomer; a copolymer of a styrene-based monomer such as styrene and α-methylstyrene and a polymerizable aromatic monomer, and the like can be mentioned.

The styrene resin preferably has a melting point in the range of 80 to 140 ° C., and preferably has a weight average molecular weight in the range of 800 to 3,000.
The blending amount of the styrene resin is preferably 0.01 to 1.5 parts by mass with respect to 100 parts by mass of the resin (A).

Examples of the plasticizer include polyisoprene, polybutene, procel oil and the like, and examples of the thermoplastic elastomer include a styrene-butadiene copolymer (SBS), a hydrogenated product of a styrene-butadiene copolymer (SEBS), SBBS, and a styrene-isoprene. Examples of the copolymerized hydrogen additive (SEPS), styrene block copolymer (TPS), olefin elastomer (TPO) and the like are examples of the reactive elastomer obtained by acid-modifying these elastomers.

Lubricants include fatty acid amide waxes such as oleate amide, erucate amide, stearate amide, behenic acid amide, ethylene bisoleic acid amide, ethylene bis erucate amide, rice wax, carnauba wax, candelilla wax, and lanolin wax. , Beeswax, whale oil, animal and vegetable oil-based wax such as beef fat, vaseline, paraffin wax, microcrystallin wax, polyethylene wax, polypropylene wax, ethylene wax, petroleum-based wax such as linear higher alcohol, dimethylpolysiloxane, dimethylpolysiloxane Examples thereof include silicones such as modified silicones in which at least one of the methyl groups in the side chain is substituted with an organic group other than the methyl group (carbinol group, polyether group, alkyl group having 2 or more carbon atoms, etc.).

Examples of the blocking inhibitor include inorganic particles such as silica, alumina, calcium oxide, calcium carbonate, calcium sulfate, calcium silicate, magnesium carbonate, precipitated barium sulfate, clay, and carbon black, acrylic resin, urethane resin, styrene resin, and epoxy resin. , Amid resins, or organic particles such as crosslinked products thereof. These may be used alone or in combination of two or more.

The blocking inhibitor preferably has an average particle size of 0.5 μm to 10 μm, and more preferably 0.5 μm to 5 μm.

In addition, the blocking inhibitor suppresses the gloss of the cured coating film of the coating agent and creates a calm appearance, so to speak, it is also effective as a matting agent.

The blending amount of the blocking inhibitor is preferably 50% by mass or less with respect to the total amount of the resin (A) and the blocking inhibitor.

Examples of the phosphoric acid compound include phosphoric acids such as hypophosphoric acid, phosphoric acid, orthophosphoric acid and hypophosphoric acid, and condensed phosphoric acids such as metaphosphoric acid, pyrophosphoric acid, tripolyphosphoric acid, polyphosphoric acid and ultraphosphoric acid, for example. Monomethyl orthophosphate, monoethyl orthophosphate, monopropyl orthophosphate, monobutyl orthophosphate, mono-2-ethylhexyl orthophosphate, monophenyl orthophosphate, monomethyl phosphite, monoethyl phosphite, monopropyl phosphite, monobutyl phosphite , Mono-2-ethylhexyl phosphite, monophenyl phosphite, di-2-ethylhexyl orthophosphate, dimethyl diphenyl phosphite, diethyl phosphite, dipropyl phosphite, dibutyl phosphite, phosphite Monos such as di-2-ethylhexyl and diphenyl phosphite, diesterates, monos from condensed phosphoric acid and alcohols, diesterates, for example, the above phosphoric acids are added with epoxy compounds such as ethylene oxide and propylene oxide. Examples thereof include epoxy phosphoric acid esters obtained by adding the above-mentioned phosphoric acids to an aliphatic or aromatic diglycidyl ether.

Examples of the silane coupling agent include γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-β (aminoethyl) -γ-aminopropyltrimethoxysilane, and N-β (aminoethyl) -γ-. Aminosilanes such as aminopropyltrimethyldimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane; β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycid Epoxysilanes such as xypropyltriethoxysilane; vinylsilanes such as vinyltris (β-methoxyethoxy) silane, vinyltriethoxysilane, vinyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane; hexamethyldisilazane, γ-mercaptopropyl Examples thereof include trimethoxysilane.

These components may be pre-blended in the first agent or the second agent, or may be added when the first agent and the second agent are mixed.

The coating agent of the present invention can be prepared by mixing each of the above-mentioned components. At this time, each component may be mixed at the same time to form a coating agent, but components other than the curing agent (B) (second agent) may be mixed in advance to adjust the mixture so that the curing agent is used when the coating agent is used. It is preferable to use a two-component coating agent in which (B) is mixed because the coating agent is excellent in stability and workability.

The coating agent of the present invention can easily form a coating layer which is a thin film but has excellent water vapor barrier properties by a simple device.

<Laminated body>
The laminate of the present invention is obtained by applying the coating agent of the present invention to a base material. The coating agent of the present invention has excellent coatability on various base materials, and can be applied to paper, synthetic paper, thermoplastic resin film, steel plate, aluminum foil, wood, woven fabric, knitted fabric, non-woven fabric, gypsum board, wood board, etc. It can be used for coating or impregnation, and a coating layer can be formed by removing the solvent. Above all, it is preferably used for paper, synthetic paper, and thermoplastic resin film.

Examples of the thermoplastic resin film include polyethylene terephthalate (PET) film, polystyrene film, polyamide film, polyacrylonitrile film, polyethylene film (LLDPE: low density polyethylene film, HDPE: high density polyethylene film), which are widely used for food applications. Examples thereof include polyolefin films such as polypropylene films (CPP: unstretched polypropylene films, OPP: biaxially stretched polypropylene films), polyvinyl alcohol films, ethylene-vinyl alcohol copolymer films and the like. These may be stretched. As a stretching treatment method, it is common to melt-extrude the resin by an extrusion film forming method or the like to form a sheet, and then perform simultaneous biaxial stretching or sequential biaxial stretching. Further, in the case of sequential biaxial stretching, it is common to first perform longitudinal stretching treatment and then lateral stretching. Specifically, a method of combining longitudinal stretching using the speed difference between rolls and transverse stretching using a tenter is often used. Further, a film obtained by laminating a vapor-deposited layer of a metal such as aluminum or stainless steel or a metal oxide such as silica or alumina may be used on the film for laminating.

In addition, polycarbonate, polyethylene terephthalate, polymethylmethacrylate, polystyrene, polyester, polyolefin, epoxy resin, melamine resin, triacetyl cellulose resin, polyvinyl alcohol, ABS resin, norbornene resin, cyclic olefin resin, and polyimide, which are widely used for industrial purposes. Examples thereof include a film made of a resin, a polyvinyl fluoride resin, a vinylidene fluoride resin, an ethylene-vinyl acetate copolymer and the like.
Further, the thickness of the base film is not particularly limited, but usually it may be in the range of 1 to 500 μm.

Further, the coating agent of the present invention may be applied to a laminate obtained by laminating two or more of these base materials using an adhesive. Since the coating agent of the present invention is excellent in water vapor barrier property and solvent resistance, for example, it is possible to prevent water vapor and solvent from infiltrating into the adhesive layer for bonding the base materials, and maintain the adhesive strength of the laminate for a long period of time. You can also do it.

As a more specific structure of the laminated body,
(1) Base film 1 / Adhesive layer 1 / Sealant film (2) Base film 1 / Adhesive layer 1 / Metal vapor deposition unstretched film (3) Base film 1 / Adhesive layer 1 / Metal vapor deposition stretched film (4) Transparent vapor-deposited stretched film / adhesive layer 1 / sealant film (5) Base film 1 / adhesive layer 1 / base film 2 / adhesive layer 2 / sealant film (6) Base film 1 / adhesive layer 1 / metal vapor-deposited stretched film / Adhesive layer 2 / Sealant film (7) Base film 1 / Adhesive layer 1 / Transparent vapor deposition stretched film / Adhesive layer 2 / Sealant film (8) Base film 1 / Adhesive layer 1 / Metal layer / Adhesive layer 2 / Sealant Film (9) Base film 1 / Adhesive layer 1 / Base film 2 / Adhesive layer 2 / Metal layer / Adhesive layer 3 / Sealant film (10) Base film 1 / Adhesive layer 1 / Metal layer / Adhesive layer 2 / Base film 2 / Adhesive layer 3 / Sealant film (11) Base film 1 / Adhesive layer 1 / Base film 2
Etc., but are not limited to this.

Examples of the base film 1 used in the configuration (1) include an OPP film, a PET film, and a nylon film. Further, the base film 1 may be coated with a gas barrier property and an ink acceptability when a printing layer described later is provided. Examples of commercially available products of the coated base film 1 include K-OPP film and K-PET film. Examples of the sealant film include a CPP film and an LLDPE film. A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side (when a coated film is used as the base film 1, the surface of the coating layer on the adhesive layer 1 side). The printing layer is formed by various printing inks such as gravure ink, flexo ink, offset ink, stencil ink, and inkjet ink by a general printing method conventionally used for printing on a polymer film.

Examples of the base film 1 used in the configurations (2) and (3) include an OPP film and a PET film. As the metal-deposited unstretched film, a VM-CPP film in which a metal such as aluminum is vapor-deposited on a CPP film is used, and as a metal-deposited stretched film, a VM-OPP film in which a metal such as aluminum is vapor-deposited on an OPP film is used. Can be done. A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side in the same manner as in the configuration (1).

Examples of the transparent vapor-deposited stretched film used in the configuration (4) include a film obtained by subjecting silica or alumina vapor deposition to an OPP film, PET film, nylon film or the like. A film coated on the vapor-deposited layer may be used for the purpose of protecting the inorganic vapor-deposited layer of silica or alumina. Examples of the sealant film are the same as those in the configuration (1). A printing layer may be provided on the surface of the transparent thin-film deposition stretched film on the adhesive layer 1 side (in the case where a coating is applied on the inorganic thin-film film, the surface on the adhesive layer 1 side of the coating layer). The method of forming the print layer is the same as that of the configuration (1).

Examples of the base film 1 used in the configuration (5) include a PET film and the like. Examples of the base film 2 include a nylon film and the like. Examples of the sealant film are the same as those in the configuration (1). A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side in the same manner as in the configuration (1).

Examples of the base film 1 of the configuration (6) include those similar to the configurations (2) and (3). Examples of the metal-deposited stretched film include a VM-OPP film and a VM-PET film in which a metal such as aluminum is vapor-deposited on an OPP film or a PET film. Examples of the sealant film are the same as those in the configuration (1). A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side in the same manner as in the configuration (1).

Examples of the base film 1 of the configuration (7) include a PET film and the like. Examples of the transparent vapor-deposited stretched film include those having the same structure as (4). Examples of the sealant film are the same as those in the configuration (1). A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side in the same manner as in the configuration (1).

Examples of the base film 1 of the configuration (8) include a PET film and a nylon film. Examples of the metal layer include aluminum foil. Examples of the sealant film are the same as those in the configuration (1). A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side in the same manner as in the configuration (1).

Examples of the base film 1 having the configurations (9) and (10) include a PET film and the like. Examples of the base film 2 include a nylon film and the like. Examples of the metal layer include aluminum foil. Examples of the sealant film are the same as those in the configuration (1). A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side in the same manner as in the configuration (1).

Examples of the base film 1 of the configuration (11) include a PET film and the like. Examples of the base film 2 include a PET film and a polyvinylidene fluoride film.

In these configurations, the coating agent of the present invention is applied, for example, to the outside of the base film 1 (the surface opposite to the side where the sealant film of the base film 1 is arranged), but the coating layer is applied at other positions. May be arranged.

Further, the coating agent of the present invention may be applied to the unstretched film and the coated film may be stretched, so-called in-line coating.

Further, it is preferable that the thermoplastic resin film is subjected to a corona discharge treatment. Silica, alumina, etc. may be vapor-deposited, or a gas barrier coat layer such as an oxygen gas barrier layer may be laminated.

When paper is used as the base material, it can be a moisture-proof paper. Examples of the base paper include kraft paper, liner paper, art paper, coated paper, carton paper and the like.

When synthetic paper is used as the base material, it can be a moisture-proof synthetic paper. The structure of the synthetic paper is not particularly limited. Therefore, it may have a single-layer structure or a multi-layer structure. As the multilayer structure, for example, there are a two-layer structure of a base material layer and a surface layer, a three-layer structure in which the base material layer and the front and back surfaces are present, and another resin film layer between the base material layer and the surface layer. A multi-layer structure can be exemplified. In addition, each layer may or may not contain an inorganic or organic filler. Further, a microporous synthetic paper having a large number of fine voids can also be used.

The method of applying the coating agent of the present invention to the substrate is not particularly limited, but gravure roll coating, reverse roll coating, wire bar coating, lip coating, air knife coating, curtain flow coating, spray coating, and immersion coating. , Brush coating method, etc. can be adopted. The amount of the coating agent applied may be appropriately determined depending on the base material. When the base material is a thermoplastic resin film, the thickness of the coating layer in the present invention is preferably at least 0.1 μm or more in order to sufficiently enhance the water vapor barrier property. From the viewpoint of water vapor barrier property, the thickness of the coating layer should be thick, but the feature of the present invention is that the water vapor barrier property is exhibited even if the thickness of the coating layer is thin. Therefore, if the coating agent of the present invention is used, , The water vapor barrier property can be enhanced while taking advantage of the characteristics of the base material. Therefore, the thickness of the coating layer of the present invention is preferably 0.1 μm and 10 μm, more preferably 0.2 μm to 8 μm, and particularly preferably 0.3 μm to 7 μm.

Further, when the base material is such that a coating agent such as paper, woven fabric, knitted fabric, or non-woven fabric soaks in, it is difficult to evaluate the coating amount by the film thickness, so the evaluation is performed by the coating mass after drying. The coating mass after drying may be in the range of 1 to 200 g / m ² .

After applying the coating agent of the present invention to the substrate, the drying temperature at which the solvent is dried is preferably 40 ° C. to 150 ° C., more preferably 40 to 130 ° C., and even more preferably 40 to 120 ° C. After drying, it is preferable to further provide an aging step. The aging conditions may be appropriately adjusted from 25 ° C. to 100 ° C. for 12 hours to 240 hours.

Further, another base material may be laminated on the coating layer of the laminate treated with the coating agent of the present invention. As the base material that can be combined, in addition to the above-mentioned base materials such as thermoplastic resin film, paper, synthetic paper, wood, woven cloth, knitted cloth, and non-woven fabric, metal foil such as aluminum is appropriately selected and used. It can be the same or different. Further, the laminated bodies of the present invention may be combined with each other.

As a method of laminating another base material, the coating layer and another base material may be bonded to each other via an adhesive, or the other base material may be laminated on the coating layer by extrusion lamination or the like.

<Packaging materials, processed products>
Since the laminate of the present invention has excellent water vapor barrier properties, for example, it is used for paper cups, moisture-proof cardboard, moisture-proof paper, water vapor barrier film, packaging of things that dislike water droplets and moisture, and internal moisture such as wet tissue diffuses to the outside. It can be used for various purposes such as packaging for items that need to be prevented from being damaged, and applications that need to prevent deterioration of the base material due to moisture because it is used for a long period of time such as front seats and back sheets of solar cells.

Further, since the laminate of the present invention is also excellent in solvent resistance, it can be preferably used as a packaging material such as shampoo and conditioner. Such contents may deteriorate the adhesive layer and cause a decrease in adhesive strength. However, if a coating layer using the coating agent of the present invention is provided between the adhesive layer and the contents, the adhesive layer Deterioration can be suppressed.

Further, the laminate of the present invention is molded and processed into various uses such as press-through packages and strip packages for accommodating foods, medical products, and daily necessities, packaging materials for battery exterior materials, and packaging materials for capacitor exterior materials. Can be preferably used.

Hereinafter, the present invention will be described with reference to Examples and Comparative Examples, but the present invention is not limited thereto. The composition and other values are based on mass unless otherwise specified.

<Adjustment of resin solution>
Preparation of (Resin Solution A-1) A crystalline maleic anhydride olefin resin is dissolved in a mixed solvent of methylcyclohexane: ethyl acetate: isopropanol = 71: 8: 1, and a resin solution A-1 having a solid content of 20% is prepared. It was adjusted. The acid value of the resin solution A-1 was 3.6 mgKOH / g.

Preparation of (Resin Solution A-2) Acrylic polyol was dissolved in a mixed solvent of toluene: ethyl acetate = 71: 29 to prepare a resin solution A-2 having a solid content of 50%. The hydroxyl value of the resin solution A-2 was 11 mgKOH / g.

Preparation of (Resin Solution A-3) The polyamide resin was dissolved in a mixed solvent of methylcyclohexane: methanol: ethanol = 61: 18: 21 to prepare a resin solution A-3 having a solid content of 38%. The polyamide resin used to prepare the resin solution A-3 does not have a functional group capable of reacting with the isocyanate compound.

Preparation of (Resin Solution A-4) A polyester polyol was dissolved in ethyl acetate = to prepare a resin solution A-4 having a solid content of 62%. The hydroxyl value of the resin solution A-4 was 11 mgKOH / g.

Preparation of (Resin Solution A-5) Nitrocellulose was dissolved in a mixed solvent of isopropanol: ethyl acetate = 55: 45 to prepare a resin solution A-5 having a solid content of 11.2%.

<Adjustment of coating agent>
(Example 1)
Resin solution A-1: 99.9 parts by mass, aliphatic amide (using a mixed solution of solid content 25% by mass, methylcyclohexane: ethyl acetate = 1: 1): 1.6 parts by mass, styrene resin (styrene-based monomer) Homopolymer, weight average molecular weight 1500): 0.2 parts by mass, triphenylphosphine: 0.01 parts by mass, 100% non-volatile content nurate-type hexamethylene diisocyanate: 6.7 parts by mass, ethyl acetate: 27 parts by mass. Was well stirred to prepare the coating agent of Example 1.

(Example 2), (Example 3)
The coating agents of Examples 2 and 3 were prepared in the same manner as in Example 1 except that the components used and the blending amounts thereof were changed as shown in Table 1.

(Comparative Example 1)-(Comparative Example 3)
The coating agent of Comparative Example 1-3 was adjusted in the same manner as in Example 1 except that the components used and the blending amount thereof were changed as shown in Table 1.

The details of the compounds described in Table 1 which are not described above are as follows.
(Anti-blocking agent)
Wet silica with an average particle size of 1.7 μm (epoxy compound 1)
Trimethylolpropane polyglycidyl ether (epoxy equivalent: 130 g / eq)
(Epoxy compound 2)
A solution of bisphenol A type epoxy resin (epoxy equivalent: 475 g / eq) xylene: ethylbenzene = 52: 48, solid content 70%
(Mixed solvent)
Methylcyclohexane: ethyl acetate: isopropanol = 58:12:30
(Carbonate)
Ethyl carbonate: Ethyl methyl carbonate: Dimethyl carbonate = 1: 1: 1

<Laminated body>
(Example 1)
The coating agent of Example 1 was applied to the corona-treated surface of the PET film (film thickness: 12 μm) with a bar coater at a coating amount of 3.0 g / m ² (dry), dried at 80 ° C. for 1 minute, and then 40. After curing (aging) at ° C. for 3 days, the laminate of Example 1 was obtained.

(Example 2), (Example 3)
Laminates of Examples 2 and 3 were obtained in the same manner as in Example 1 except that the base material was changed to a nylon film (film thickness: 25 μm).

(Comparative Example 1)-(Comparative Example 3)
A laminate of Comparative Example 1-3 was obtained in the same manner as in Example 2.

<Evaluation>
The laminates of Example 1-3 and Comparative Example 1-3 were evaluated as follows, and the results are summarized in Table 1.
(Adhesion to base material)
Cellophane tape (TF-12 manufactured by Nichiban Co., Ltd.) was pressure-bonded to the coating layer, and the degree of peeling when the tape was peeled off at once was visually judged and evaluated on a three-point scale.
〇: No peeling △: Partially peeled ×: All peeled

(Heat-resistant)
A heat sealer was pressed on the coating layer at a sealing pressure of 0.1 MPa and a temperature of 190 ° C. for 1 second, and the surface condition after pressing was visually evaluated in two stages.
〇: No change ×: There is deposit on the heat seal bar

(Solvent resistance)
A few drops of various solvents were added dropwise to the coating layer, and the mixture was allowed to stand at room temperature for 2 hours and then the surface was wiped off. The state of the coating layer after wiping was visually evaluated in three stages.
〇: No change △: Droplet edge was visible ×: The coating layer was dissolved

(Water vapor barrier property)
The measurement was carried out in an atmosphere of 40 ° C. and 90% RH according to the conductivity method "ISO-15106-3" using a water vapor transmittance measuring device 7002 manufactured by Illinois. The unit is cc / m ² / day / atm.

As is clear from Table 1, the coating agent of the present invention has excellent water vapor barrier properties and the like.

Claims (10)

A two-component coating agent containing an acid group-containing olefin resin (A1), an isocyanate compound (B1), and an organic solvent. The two-component coating agent according to claim 1, wherein the isocyanate compound contains an aliphatic isocyanate. The two-component coating agent according to any one of claims 1 or 2, further comprising an acid anhydride. The two-component coating agent according to any one of claims 1 to 3, further comprising a curing accelerator. The two-component coating agent according to any one of claims 1 to 4, further comprising a lubricant. The two-component coating agent according to any one of claims 1 to 5, further comprising an antiblocking agent. The two-component coating agent according to any one of claims 1 to 6, further comprising a tackifier. A laminate having a cured coating film of the two-component coating agent according to any one of claims 1 to 7 on a base material. The packaging material made of the laminate according to claim 8. A packaging material obtained by molding the laminate according to claim 8.