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WO2018198921A1 - Composition, produit durci et procédé de production d'un produit durci - Google Patents

Composition, produit durci et procédé de production d'un produit durci Download PDF

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Publication number
WO2018198921A1
WO2018198921A1 PCT/JP2018/016098 JP2018016098W WO2018198921A1 WO 2018198921 A1 WO2018198921 A1 WO 2018198921A1 JP 2018016098 W JP2018016098 W JP 2018016098W WO 2018198921 A1 WO2018198921 A1 WO 2018198921A1
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WO
WIPO (PCT)
Prior art keywords
compound
composition
formula
represented
cured product
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2018/016098
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English (en)
Japanese (ja)
Inventor
康孝 岡
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DIC Corp
Original Assignee
DIC Corp
Dainippon Ink and Chemicals Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by DIC Corp, Dainippon Ink and Chemicals Co Ltd filed Critical DIC Corp
Publication of WO2018198921A1 publication Critical patent/WO2018198921A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/38—Layered products comprising a layer of synthetic resin comprising epoxy resins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives

Definitions

  • the present invention relates to a composition having excellent gas barrier properties, a cured product, and a method for producing the cured product.
  • Packaging materials typically used for packaging foods and beverages protect the contents from various distributions, storage such as refrigeration and processing such as heat sterilization, so that the strength, resistance to cracking, retort resistance, heat resistance
  • functions such as properties
  • a variety of functions are required, such as excellent transparency so that the contents can be confirmed.
  • the required performance of plastic films used for packaging foods, pharmaceuticals, cosmetics, etc. includes barrier properties against various gases, transparency, retort resistance, impact resistance, flexibility, heat sealability, etc.
  • a high barrier property against oxygen and water vapor is particularly required including conditions such as high humidity and after retorting.
  • Such a gas barrier packaging material is usually constituted by laminating materials such as a flexible polymer film layer serving as a base material, a gas barrier layer, and a flexible polymer film layer serving as a sealant layer.
  • a gas barrier material for forming a gas barrier layer vinylidene chloride having high retort resistance and gas or water vapor barrier properties has been frequently used.
  • dioxin is generated at the time of disposal firing.
  • polyvinyl alcohol resin or ethylene-polyvinyl alcohol copolymer is used as a barrier coating material, the oxygen barrier property is high under low humidity, but there is a problem that the oxygen barrier property is lowered under high humidity.
  • An object of the present invention is to provide a composition that exhibits a high oxygen barrier property even under high humidity, and a cured product of the composition.
  • the present inventors have found that in order to solve the above problems, the compound A represented by the following formula (1), the compound B represented by the following formula (2), and an aromatic ring or alicyclic structure And a compound C having two or more epoxy groups, wherein the molar ratio of epoxy groups to carboxyl groups in the composition is 0.1 to 1.8 I will provide a.
  • X 1 represents an aromatic ring or alicyclic structure, and n1 and n2 each independently represents an integer of 0 to 3.
  • composition whose compound C is a structure represented by following formula (3) is provided.
  • X 2 represents an aromatic ring or alicyclic structure
  • n3 represents an integer of 2 to 6
  • R 2 independently represents a group represented by Formula (4) below.
  • Y 1 and Y 3 each independently represent a divalent hydrocarbon group or an oxygen atom
  • Y 2 represents a trivalent hydrocarbon group or a nitrogen atom
  • n4 and n6 each independently represents 0 to 3 Represents an integer, n5 is 0 or 1, n7 is 1 when n5 is 0, and n7 is 2 when n5 is 1.
  • the resin P obtained by reacting the compound A represented by the formula (1) and the compound B represented by the formula (2), an aromatic ring or alicyclic structure, and two or more epoxy groups The composition characterized by containing the compound C which has these.
  • the process 1 which makes the compound A represented by the said Formula (1), the compound B represented by the said Formula (2) react, and obtains resin P, an aromatic ring or an alicyclic structure, and two or more
  • a method for producing a cured product comprising the step 2 of reacting the compound C having an epoxy group with a resin P to obtain a cured product.
  • composition of the present invention By providing the composition of the present invention, it is possible to provide a composition that exhibits high oxygen barrier properties even under high humidity, and a cured product of the composition. Moreover, since the composition of the present invention exhibits high barrier properties even under high humidity, it can be suitably used for coating agents, adhesives, gas barrier materials, and the like.
  • the present invention relates to a compound A represented by the following formula (1), a compound B represented by the following formula (2), A composition comprising an aromatic or alicyclic structure and compound C having two or more epoxy groups, wherein the molar ratio of epoxy groups to carboxyl groups in the composition is 0.1 to 1.8.
  • the composition characterized by these is provided.
  • X 1 represents an aromatic ring or alicyclic structure, and n1 and n2 each independently represents an integer of 0 to 3.
  • R 1 represents a hydrogen atom, a hydrocarbon group having 1 to 3 carbon atoms or a carbonyl group, and m1 to m3 each independently represents an integer of 0 to 3)
  • Compound A of the present invention is a compound having an isocyanate group represented by the formula (1).
  • X 1 represents an aromatic ring or alicyclic structure. By having an aromatic ring or alicyclic structure, a high barrier property can be exhibited.
  • the aromatic ring structure is preferably an aromatic ring having 6 to 18 carbon atoms, and examples thereof include a benzene ring, a naphthalene ring, a phenanthrene ring, and an anthracene ring.
  • the aromatic ring may be substituted with at least one fluorine atom, and examples of the aromatic ring substituted with at least one fluorine atom include a perfluorophenyl group.
  • the alicyclic structure is preferably an alicyclic ring having 3 to 20 carbon atoms, and may be a single ring or a condensed ring.
  • cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, cycloundecane, cyclododecane, and the like.
  • Monocyclic cycloalkenes include cyclopropene, cyclobutene, cyclopropene, cyclohexene, cycloheptene, cyclooctene and the like.
  • the condensed ring include bicycloundecane, decahydronaphthalene, norbornene, and norbornadiene.
  • polycyclic compounds include cubane, basketan, and house. Moreover, you may be the ring structure which combined the aromatic ring and the alicyclic ring.
  • X 1 is preferably a benzene ring or a naphthalene ring. Further, n1 and n2 are preferably each independently 0 to 1.
  • the more preferable structure of compound A includes the following structures.
  • Compound B of the present invention is a diol compound having a carboxyl group represented by the formula (2). By having a carboxyl group, it reacts with the compound C described later to form a crosslinked structure, and can exhibit high oxygen barrier properties under high humidity.
  • Compound B is preferably a compound in which m3 is 0, and more preferably, R1 is a hydrocarbon group having 1 to 3 carbon atoms.
  • Compound B More preferred structures of Compound B include dimethylolpropionic acid and dimethylolbutanoic acid.
  • the compound C of the present invention is a compound having an aromatic ring or alicyclic structure and two or more epoxy groups.
  • Compound C of the present invention can exhibit high barrier properties due to the aromatic ring or alicyclic structure.
  • a crosslinked structure is formed by the reaction of the epoxy group and the carboxyl group of compound B, and a high oxygen barrier property under high humidity can be exhibited.
  • Preferred structures of the compound C of the present invention include an alicyclic epoxy compound or a structure represented by the following formula (3).
  • X 2 represents an aromatic ring or alicyclic structure
  • n 3 represents an integer of 2 to 6
  • R 2 independently represents a group represented by Formula (4) below
  • Y 1 and Y 3 each independently represent a divalent hydrocarbon group or an oxygen atom
  • Y 2 represents a trivalent hydrocarbon group or a nitrogen atom
  • n4 and n6 each independently represents 0 to 3 Represents an integer, n5 is 0 or 1, n7 is 1 when n5 is 0, and n7 is 2 when n5 is 1.
  • examples of the aromatic ring or alicyclic structure in X 2 include the same structures as the aromatic ring or alicyclic structure in compound A. Of these, a benzene ring, a naphthalene ring or a cycloalkane is preferred.
  • Y 1 is an oxygen atom.
  • particularly preferable structures include the following structures.
  • the alicyclic epoxy group is preferably a cyclopentene oxide group or a cyclohexene oxide group.
  • Particularly preferable structures include the following structures.
  • the composition of the present invention is a composition containing Compound A, Compound B and Compound C, wherein the molar ratio of the epoxy group to the carboxyl group in the composition is 0.1 to 1.8. To do. When the molar ratio of the epoxy group to the carboxyl group is less than 0.1, the curability is poor and the moldability is deteriorated. When it is more than 1.8, the oxygen barrier property under high humidity becomes insufficient.
  • the molar ratio of the epoxy group to the carboxyl group is preferably 0.1 to 1.5.
  • the composition of the present invention comprises a resin P obtained by reacting compound A and compound B, and a compound C having an aromatic or alicyclic structure and two or more epoxy groups. It may be a thing. At this time, the molar ratio of the epoxy group to the carboxyl group in the composition is preferably 0.1 to 1.8.
  • the composition of the present invention may contain a filler.
  • a filler There is no limitation in particular as a filler, An inorganic filler and an organic filler are mentioned.
  • the shape is not particularly limited, and may be various shapes such as a spherical shape, a granular shape, a rod shape, a needle shape, a fiber shape, a plate shape, and a woven / nonwoven shape.
  • the aspect ratio can be high or low.
  • fillers that improve barrier properties may be blended.
  • it is a layered inorganic compound or a compound having an oxygen supplementing function.
  • layered inorganic compounds include hydrous silicates (phyllosilicate minerals, etc.), kaolinite group clay minerals (halloysite, kaolinite, enderite, dickite, nacrite, etc.), and antigolite group clay minerals (antigolite). , Chrysotile, etc.), smectite group clay minerals (montmorillonite, beidellite, nontronite, saponite, hectorite, soconite, stevensite, etc.), vermiculite group clay minerals (vermiculite, etc.), mica or mica group clay minerals (muscovite, gold) Mica such as mica, margarite, tetrasilic mica, and teniolite). These minerals may be natural clay minerals or synthetic clay minerals.
  • a layered inorganic compound is used individually or in combination of 2 or more types.
  • a preferred blending amount is 5-60% by mass of the layered clay mineral in the composition. More preferably, it is 5-50 mass%.
  • Examples of the compound having an oxygen scavenging function include low molecular organic compounds that react with oxygen such as hindered phenols, vitamin C, vitamin E, organic phosphorus compounds, gallic acid, pyrogallol, cobalt, manganese, nickel, iron, Examples include transition metal compounds such as copper.
  • the composition may contain a solvent depending on the intended use.
  • the solvent include organic solvents such as methyl ethyl ketone, acetone, ethyl acetate, butyl acetate, toluene, dimethylformamide, acetonitrile, methyl isobutyl ketone, methanol, ethanol, methoxypropanol, cyclohexanone, methyl cellosolve, ethyl diglycol acetate, propylene glycol.
  • examples thereof include monomethyl ether acetate. What is necessary is just to select the kind and usage-amount of a solvent suitably according to a use application.
  • the composition may contain various additives as long as the effects of the present invention are not impaired.
  • additives include various resins, reactive compounds, catalysts, polymerization initiators, stabilizers (antioxidants, heat stabilizers, ultraviolet absorbers, etc.), plasticizers, waxes, surfactants, stabilizers, fluids
  • regulators antistatic agents, lubricants, antiblocking agents, colorants, crystal nucleating agents, coupling agents, dyes, leveling agents, rheology control agents, ultraviolet absorbers, compounds having an oxygen scavenging function, tackifiers, etc. it can.
  • the composition of the present invention may contain a curing agent.
  • a curing agent For example, when a compound having an epoxy group is blended, an amine curing agent, an amide curing agent, an acid anhydride curing agent.
  • Various curing agents such as a phenolic curing agent, an active ester curing agent, a carboxyl group-containing curing agent and a thiol curing agent may be used in combination.
  • the amine curing agents include diaminodiphenylmethane, diaminodiphenylethane, diaminodiphenyl ether, diaminodiphenylsulfone, orthophenylenediamine, metaphenylenediamine, paraphenylenediamine, metaxylenediamine, paraxylenediamine, diethyltoluenediamine, diethylenetriamine. , Triethylenetetramine, isophoronediamine, imidazole, BF3-amine complex, guanidine derivative, guanamine derivative and the like.
  • amide-based curing agent examples include polyamide resins synthesized from dicyandiamide and a dimer of linolenic acid and ethylenediamine.
  • acid anhydride curing agents include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methyl nadic anhydride, hexahydrophthalic anhydride, methylhexa And hydrophthalic anhydride.
  • phenolic curing agents include bisphenol A, bisphenol F, bisphenol S, resorcin, catechol, hydroquinone, fluorene bisphenol, 4,4'-biphenol, 4,4 ', 4 "-trihydroxytriphenylmethane, naphthalenediol, 1 , 1,2,2-tetrakis (4-hydroxyphenyl) ethane, calixarene, phenol novolac resin, cresol novolac resin, aromatic hydrocarbon formaldehyde resin-modified phenol resin, dicyclopentadiene phenol addition type resin, phenol aralkyl resin (Xylok) Resin), polyhydric phenol novolak resin synthesized from formaldehyde and polyhydric hydroxy compound represented by resorcinol novolak resin, naphthol aralkyl resin, trimethylo Rumethane resin, tetraphenylolethane resin, naphthol novolak resin, naphthol-phenol co-
  • a curing accelerator can be used.
  • Various compounds that promote the curing reaction of the epoxy resin can be used as the curing accelerator, and examples thereof include phosphorus compounds, tertiary amine compounds, imidazole compounds, organic acid metal salts, Lewis acids, and amine complex salts.
  • the use of an imidazole compound, a phosphorus compound, and a tertiary amine compound is preferable, and particularly when used as a semiconductor sealing material, it is excellent in curability, heat resistance, electrical characteristics, moisture resistance reliability, and the like.
  • Triphenylphosphine is preferable for phosphorus compounds, and 1,8-diazabicyclo- [5.4.0] -undecene (DBU) is preferable for tertiary amines.
  • the composition of the present invention can be cured.
  • a hardening method What is necessary is just to use a well-known and usual method.
  • thermal curing, thermal radical curing, etc. are mentioned.
  • the composition containing Compound A, Compound B, and Compound C may be cured directly, or after creating a resin P obtained by reacting Compound A and Compound B, You may make it harden
  • cure you may use together the hardening
  • the molding method is arbitrary and may be selected as appropriate depending on the application. There is no restriction
  • the composition is molded using, for example, an extrusion molding method, a plane press, a modified extrusion molding method, a blow molding method, a compression molding method, a vacuum molding method, an injection molding method, or the like.
  • a method is mentioned.
  • melt extrusion method, solution casting method, inflation film molding, cast molding, extrusion lamination molding, calendar molding, sheet molding, fiber molding, blow molding, injection molding, rotational molding examples include coating molding.
  • the composition is cured with heat or active energy rays, the composition may be molded using various curing methods using heat or active energy rays.
  • composition is liquid, it may be formed by coating.
  • Coating methods include spray method, spin coating method, dipping method, roll coating method, blade coating method, doctor roll method, doctor blade method, curtain coating method, slit coating method, screen printing method, ink jet method, dispensing method, etc. Is mentioned.
  • the laminate of the present invention is provided with a cured product layer obtained by curing the above-described composition on a substrate.
  • the laminate may have a two-layer structure or a three-layer structure or more.
  • the material of the base material is not particularly limited and may be appropriately selected depending on the application. Examples thereof include wood, metal, plastic, paper, silicon, modified silicon, and the like, which are obtained by joining different materials. There may be. There is no restriction
  • the laminated body can be obtained by laminating the above-described molded body on the base material.
  • the molded body laminated on the base material may be formed by direct coating or direct molding on the base material, or a molded body of the composition may be laminated.
  • the coating method is not particularly limited, spray method, spin coating method, dip method, roll coating method, blade coating method, doctor roll method, doctor blade method, curtain coating method, slit coating method, A screen printing method, an inkjet method, etc. are mentioned.
  • direct molding in-mold molding, insert molding, vacuum molding, extrusion lamination molding, press molding and the like can be mentioned.
  • laminating a molded product of the composition an uncured or semi-cured composition layer may be laminated on the substrate and then cured, or a cured product layer obtained by completely curing the composition is laminated on the substrate. May be.
  • the laminate may be obtained by applying a substrate precursor to the cured layer of the composition and curing it, and the substrate precursor or composition is in an uncured or semi-cured state. It may be obtained by curing after bonding.
  • a substrate precursor to the cured layer of the composition and curing it
  • the substrate precursor or composition is in an uncured or semi-cured state. It may be obtained by curing after bonding.
  • a precursor of a base material Various curable compositions etc. are mentioned.
  • you may create a laminated body by using the composition which concerns on embodiment as an adhesive agent.
  • composition of the present invention can be suitably used as a coating material or an adhesive. That is, the coating material or adhesive of the embodiment only needs to include the above-described composition.
  • the composition of the present invention can be applied as a two-component type or a one-component type.
  • the coating method for the coating material is not particularly limited, and examples of specific methods include various coating methods such as roll coating and gravure coating. Also, the coating apparatus is not particularly limited.
  • the composition is excellent in adhesiveness, it can be suitably used as an adhesive.
  • the form of the adhesive is not particularly limited, and may be a liquid or paste adhesive, or a solid adhesive. Since the composition has high gas barrier properties, this adhesive can be suitably used as a gas barrier adhesive.
  • a liquid or paste-like adhesive it may be a one-component adhesive, or a two-component adhesive separately from a curing agent.
  • the method of use is not particularly limited, but after application to one adhesive surface, the other adhesive surface may be bonded and bonded, or after injection at the interface of the adhesive surface Can be glued.
  • an adhesive formed into a powder, chip, or sheet may be installed at the interface of the adhesive surface, and thermally bonded to be cured and cured.
  • Example 1 10 parts by mass of polyurethane solution 1 prepared in Synthesis Example 1 and 1.6 parts by mass of resorcinol diglycidyl ether (trade name: Denacol EX201, manufactured by Nagase ChemteX Corporation) with respect to the carboxyl group of “DMPA / XDI” 1 equivalent group), 0.07 parts by mass of triphenylphosphine as a curing catalyst (1% by mass with respect to the total weight of the urethane resin and the epoxy resin), and 7.4 parts by mass of methanol, and a non-volatile content of 35% by mass A coating solution was prepared.
  • PET polyethylene terephthalate
  • E-5100 manufactured by Toyobo Co., Ltd.
  • bar coater # 4 was applied to a 12 ⁇ m thick polyethylene terephthalate (PET) film (“E-5100” manufactured by Toyobo Co., Ltd.) with a bar coater # 4 and dried at 80 ° C. for 30 seconds to form a 2 ⁇ m film on the PET film. Further, curing was performed by heating in an oven at 80 ° C. for 24 hours, and the oxygen transmission rate of the obtained coating film 1 was measured. The results are shown in Table 1.
  • Example 2 to [Example 5] Coating films 2 to 5 were obtained in the same manner as in Example 1 except that the formulations shown in Table 1 were changed. The blending amount and oxygen transmission rate are shown in Table 1.
  • Comparative Example 3 A comparative coating film 3 was obtained in the same manner as in Comparative Example 2 except that the formulation shown in Table 1 was changed. The formulation and oxygen transmission rate are shown in Table 1.
  • Denacol EX-201 Nagase ChemteX Corporation, resorcinol diglycidyl ether Celoxide 2021P: Daicel Corporation 3 ′, 4′-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate
  • TETRAD-X Mitsubishi Gas Chemical Co., Ltd., N, N, N ′, N′-tetraglycidyl-m-xylylenediamine / Denacol EX-810: manufactured by Nagase ChemteX Corporation, ethylene glycol diglycidyl ether
  • composition of the present invention By providing the composition of the present invention, it is possible to provide a composition that exhibits high oxygen barrier properties even under high humidity, and a cured product of the composition. Moreover, since the composition of the present invention exhibits high barrier properties even under high humidity, it can be suitably used for coating agents, adhesives, gas barrier materials, and the like.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Epoxy Resins (AREA)

Abstract

L'invention concerne une composition qui comprend un composé A qui présente une structure spécifique contenant un groupe isocyanate, un composé B qui présente une structure spécifique contenant un groupe hydroxyle et un groupe carboxyle et un composé C qui présente une structure cyclique aromatique ou alicyclique et qui contient deux groupes époxy ou plus, la composition étant caractérisée en ce que le rapport molaire des groupes époxy au groupe carboxyle dans la composition est de 0,1 à 1,8. L'invention concerne également une composition caractérisée en ce qu'elle comprend un composé A, une résine P qui est obtenue par réaction avec un composé B et un composé C qui présente une structure cyclique aromatique ou alicyclique et deux groupes époxy ou plus.
PCT/JP2018/016098 2017-04-28 2018-04-19 Composition, produit durci et procédé de production d'un produit durci Ceased WO2018198921A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2017089776 2017-04-28
JP2017-089776 2017-04-28
JP2017-137040 2017-07-13
JP2017137040 2017-07-13

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WO2018198921A1 true WO2018198921A1 (fr) 2018-11-01

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007297604A (ja) * 2006-04-03 2007-11-15 Showa Denko Kk 熱硬化性樹脂組成物
JP2008045032A (ja) * 2006-08-16 2008-02-28 Showa Denko Kk 熱硬化性樹脂組成物、オーバーコート剤および、保護膜
WO2009011304A1 (fr) * 2007-07-18 2009-01-22 Showa Denko K. K. Composition de résine thermodurcissable
JP2009280686A (ja) * 2008-05-21 2009-12-03 Hitachi Chem Co Ltd 熱硬化性樹脂組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007297604A (ja) * 2006-04-03 2007-11-15 Showa Denko Kk 熱硬化性樹脂組成物
JP2008045032A (ja) * 2006-08-16 2008-02-28 Showa Denko Kk 熱硬化性樹脂組成物、オーバーコート剤および、保護膜
WO2009011304A1 (fr) * 2007-07-18 2009-01-22 Showa Denko K. K. Composition de résine thermodurcissable
JP2009280686A (ja) * 2008-05-21 2009-12-03 Hitachi Chem Co Ltd 熱硬化性樹脂組成物

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