WO2018179689A1 - 防曇性を有する接着剤組成物 - Google Patents
防曇性を有する接着剤組成物 Download PDFInfo
- Publication number
- WO2018179689A1 WO2018179689A1 PCT/JP2018/001127 JP2018001127W WO2018179689A1 WO 2018179689 A1 WO2018179689 A1 WO 2018179689A1 JP 2018001127 W JP2018001127 W JP 2018001127W WO 2018179689 A1 WO2018179689 A1 WO 2018179689A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyester resin
- adhesive composition
- film
- mass
- resin
- Prior art date
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/22—Plastics; Metallised plastics
- C09J7/25—Plastics; Metallised plastics based on macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/255—Polyesters
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- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
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- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
- B32B27/304—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising vinyl halide (co)polymers, e.g. PVC, PVDC, PVF, PVDF
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
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- B65D65/00—Wrappers or flexible covers; Packaging materials of special type or form
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- C—CHEMISTRY; METALLURGY
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J7/00—Adhesives in the form of films or foils
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
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- B32B2264/02—Synthetic macromolecular particles
- B32B2264/0214—Particles made of materials belonging to B32B27/00
- B32B2264/0228—Vinyl resin particles, e.g. polyvinyl acetate, polyvinyl alcohol polymers or ethylene-vinyl acetate copolymers
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- B32B2439/70—Food packaging
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- C—CHEMISTRY; METALLURGY
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- Y02A40/90—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in food processing or handling, e.g. food conservation
Definitions
- the present invention relates to an adhesive composition having both adhesiveness and antifogging properties. More specifically, the present invention relates to an adhesive composition used for bonding a thermoplastic resin film and a packaging container. In particular, the present invention relates to an adhesive composition for a lid of a food packaging container.
- polyester containers with excellent transparency and recyclability have been widely used as packaging materials for fresh foods such as vegetables and fruits.
- a perfect seal can extend the shelf life of fresh food, and is attracting attention as a candidate for the food distribution revolution.
- the anti-fogging property is calculated
- the antifogging agent is melt-kneaded into a resin and molded into a film, and after the resin is molded into a film, the contents
- a method of applying an antifogging agent to a surface in contact with an object has been proposed.
- the anti-fogging agent has the property of easily moving in a multilayer film. If the antifogging agent is transferred to a layer adjacent to the layer containing the antifogging agent, the adhesion between the layers is affected, and peeling occurs.
- Patent Document 1 a multilayer film of at least four layers formed by laminating an olefin resin and a polyester resin, and a layer for kneading an antifogging agent is selected, and the surface treatment of the multilayer film is performed. Multilayer films obtained by performing appropriately have been proposed.
- Patent Document 2 proposes a method in which an antifogging agent is applied to the surface in contact with the contents after the resin is formed into a film.
- Patent Document 1 an antifogging agent is kneaded by melt-kneading, and a film is formed by a special machine base that performs multilayer coextrusion and surface treatment, so that a thin adhesive layer can be easily formed. It is difficult.
- patent document 2 since the coating liquid containing an anti-fogging agent is apply
- the adhesive composition having specific physical properties has high adhesion without causing a decrease in antifogging property or a decrease in adhesiveness due to the movement of the antifogging agent.
- the present invention has been completed by finding that it has excellent properties and antifogging properties.
- an object of the present invention is to provide an adhesive composition excellent in high adhesiveness and antifogging property by a simple method such as co-extrusion, extrusion coating, and solvent coating with a base film.
- the glass transition temperature of the polyester resin (A) is ⁇ 30 to 30 ° C.
- the polyester resin (B) preferably contains a polyester resin (B) and satisfies the following (2), and the antifogging agent (C) is preferably a nonionic surfactant.
- the glass transition temperature of the polyester resin (B) is 40 to 90 ° C.
- the adhesive composition contains 0.1 to 50 parts by mass of the antifogging agent (C) and 10 to 150 parts by mass of the polyester resin (B) with respect to 100 parts by mass of the polyester resin (A). Is preferred.
- thermoplastic film is a polyester resin film and the thickness of the adhesive layer is in the range of 1 to 10 ⁇ m.
- a packaging material comprising the laminated film as a constituent member, and a food packaging container lid member comprising the packaging material as a constituent member.
- the adhesive composition according to the present invention and a laminated film using the same are excellent in adhesiveness with a substrate when heat sealed as a lid for a packaging container. Furthermore, since antifogging property is favorable, it can be used suitably as packaging materials, such as fresh food.
- the adhesive composition according to the present invention contains the following components (A) and (C).
- components (A) and (C) By containing the component (A) and the component (C), excellent adhesiveness and antifogging properties can be obtained. Furthermore, the outstanding blocking resistance is also obtained by containing (B) component.
- B component.
- polyester resin (A) used in the present invention has a chemical structure obtained by polycondensation of a carboxylic acid component composed of a divalent or higher polyhydric carboxylic acid compound and an alcohol component composed of a divalent or higher polyhydric alcohol compound. It is preferably a polyester or a copolymer of hydroxycarboxylic acid or lactone.
- a polyvalent carboxylic acid compound and an alcohol component composed of a divalent or higher polyhydric alcohol compound are preferably copolyester resins mainly composed of a dicarboxylic acid component and a glycol component.
- the total of the dicarboxylic acid component and the glycol component is 100 mol% or more on a molar basis with respect to the total 200 mol% of the total acid component and the total alcohol component constituting the polyester resin (A) used in the present invention. It means to occupy.
- the total of the dicarboxylic acid component and the glycol component is preferably 140 mol% or more, more preferably 170 mol% or more, further preferably 190 mol% or more, and may be 200 mol%. .
- the dicarboxylic acid is preferably an aromatic dicarboxylic acid or an aliphatic dicarboxylic acid, and more preferably an aromatic dicarboxylic acid.
- the copolymerization amount of the aromatic dicarboxylic acid component is preferably 40 mol% or more, more preferably 45 mol% or more, further preferably 50 mol%, when the total amount of the carboxylic acid components is 100 mol%. It is above, Especially preferably, it is 55 mol% or more. If it is less than 40 mol%, the mechanical strength of the resulting coating film may be lowered, and in that case, it is not practical.
- the dicarboxylic acid component is preferably composed only of an aromatic dicarboxylic acid and an aliphatic dicarboxylic acid.
- aromatic dicarboxylic acid examples include, but are not limited to, terephthalic acid, isophthalic acid, orthophthalic acid, and naphthalenedicarboxylic acid.
- aliphatic dicarboxylic acid examples include, but are not limited to, succinic acid, adipic acid, azelaic acid, sebacic acid, and dodecanedicarboxylic acid. These dicarboxylic acid components can be used alone or in combination of two or more.
- polyvalent carboxylic acid components include aromatic oxycarboxylic acids such as p-oxybenzoic acid and p- (hydroxyethoxy) benzoic acid, fumaric acid, maleic acid, itaconic acid, hexahydrophthalic acid and tetrahydrophthalic acid. It is also possible to use alicyclic dicarboxylic acids such as unsaturated alicyclic dicarboxylic acids such as 1,2-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid and 1,4-cyclohexanedicarboxylic acid. Furthermore, it may contain tri- and tetracarboxylic acids such as trimellitic acid, trimesic acid and pyromellitic acid, and anhydrides thereof as necessary.
- aromatic oxycarboxylic acids such as p-oxybenzoic acid and p- (hydroxyethoxy) benzoic acid, fumaric acid, maleic acid, itaconic acid, he
- the copolymerization amount of the aliphatic glycol component is preferably 70 mol% or more, more preferably 75 mol% or more, further preferably 80 mol% or more, when the total amount of the glycol components is 100 mol%. In particular, it is preferably 90 mol% or more, and may be 100 mol%. When it is less than 70 mol%, the glass transition temperature (hereinafter also referred to as Tg) of the obtained coating film may be high, and may not be suitable for use as an adhesive.
- Tg glass transition temperature
- aliphatic glycols include ethylene glycol, propylene glycol, 1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 2-methyl-1,3-propanediol (hereinafter 2MG). 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 3-methyl-1,5-pentanediol, diethylene glycol, triethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol , Polytetramethylene glycol and the like, but are not limited thereto. These glycol components can be used alone or in combination of two or more.
- glycols include 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, tricyclodecanediol, bisphenol A ethylene oxide adduct and propylene oxide adduct, hydrogenation An ethylene oxide adduct and a propylene oxide adduct of bisphenol A can also be used.
- a small amount of triol such as trimethylolethane, trimethylolpropane, glycerin, pentaerythritol, and tetraol may be contained if necessary.
- the polyester resin (A) can be produced by a known method.
- the above dicarboxylic acid and glycol components are esterified at 150 to 250 ° C. and then polycondensed at 230 to 300 ° C. under reduced pressure. By doing so, the target polyester resin can be obtained.
- a hydrophilic polar group is introduced, it is preferable to add a monovalent inorganic salt such as sodium acetate or potassium acetate as a polymerization stabilizer.
- a hindered phenol or a hindered amine type as a heat stabilizer.
- the glass transition temperature of the polyester resin (A) is ⁇ 30 to 30 ° C., preferably ⁇ 25 to 25 ° C., and more preferably ⁇ 20 to 20 ° C. When it is less than the above value, blocking may occur when the laminated film is rolled up. If the above value is exceeded, the resin may not be flexible at the time of peeling at room temperature, and the adhesiveness may decrease.
- the polyester resin (A) is preferably an amorphous polyester resin.
- a crystalline polyester resin may be used as long as it is within the glass transition temperature.
- the melting point is preferably 200 ° C. or lower, more preferably 180 ° C. or lower, and further preferably 160 ° C. or lower. When the melting point exceeds 200 ° C., good laminating properties may not be exhibited during bonding.
- the crystalline polyester resin referred to in the present invention is a temperature difference from ⁇ 100 ° C. to 250 ° C. at 20 ° C./min using a differential scanning calorimeter (DSC), and a clear melting peak is observed in the temperature rising process.
- a non-crystalline polyester resin is heated at a rate of 20 ° C./min from ⁇ 100 ° C. to 250 ° C. using a differential scanning calorimeter (DSC). Points that do not show a peak.
- the reduced viscosity ( ⁇ sp / c) of the polyester resin (A) is preferably 0.2 to 1.5 dl / g. More preferably, it is 0.4 to 1.4 dl / g, and still more preferably 0.6 to 1.3 dl / g. If it is less than the above value, the resin cohesive force may be insufficient and the adhesiveness may decrease.
- the reduced viscosity can be arbitrarily adjusted by changing the polymerization time and temperature of the polyester and the degree of reduced pressure during polymerization (in the case of reduced pressure polymerization).
- the reduced viscosity is a value measured using an Ubbelohde viscosity tube at a sample concentration of 0.125 g / 25 ml, a measurement solvent chloroform and a measurement temperature of 25 ° C.
- the acid value of the polyester resin (A) is preferably 50 mgKOH / g or less, more preferably 40 mgKOH / g or less, and further preferably 30 mgKOH / g or less.
- the lower limit is not particularly limited, and may be 0 mgKOH / g, but is preferably 0.1 mgKOH / g or more, more preferably 0.5 mgKOH / g or more.
- the number average molecular weight (Mn) of the polyester resin (A) is preferably 5000 to 40000. More preferably, it is 10,000-35,000, and more preferably 15,000-30000. If it is less than the above value, the resin cohesive force may be insufficient and the adhesiveness may decrease.
- the number average molecular weight can be arbitrarily adjusted by changing the polymerization time and temperature of the polyester, and the degree of reduced pressure during polymerization (in the case of reduced pressure polymerization).
- the number average molecular weight is a value measured by gel permeation chromatography (hereinafter, GPC, standard substance: polystyrene resin, mobile phase: tetrahydrofuran or chloroform).
- the content of the polyester resin (A) in the adhesive composition is preferably 40 to 99% by mass, more preferably 50 to 98% by mass, and still more preferably based on the solid content of the adhesive composition. Is from 60 to 95% by mass, particularly preferably from 70 to 90% by mass. If the above value is exceeded, blocking may occur when the laminated film is rolled up. If it is less than the above value, the resin does not have flexibility at the time of peeling at room temperature, and the adhesiveness may decrease.
- the polyester resin (A) can be used alone or in combination of two or more as long as it is a polyester resin within the glass transition temperature.
- the polyester resin (B) used in the present invention comprises a carboxylic acid component composed of a divalent or higher polyvalent carboxylic acid compound and an alcohol component composed of a divalent or higher polyhydric alcohol compound. It is preferably a polyester having a chemical structure obtained by polycondensation or a copolymer of hydroxycarboxylic acid or lactone.
- a polyvalent carboxylic acid compound and an alcohol component composed of a divalent or higher polyhydric alcohol compound are preferably copolyester resins mainly composed of a dicarboxylic acid component and a glycol component.
- the total of the dicarboxylic acid component and the glycol component is 100 mol% or more on a molar basis with respect to the total 200 mol% of the total acid component and the total alcohol component constituting the polyester resin (B) used in the present invention.
- the total of the dicarboxylic acid component and the glycol component is preferably 140 mol% or more, more preferably 170 mol% or more, preferably 190 mol% or more, and may be 200 mol%.
- the manufacturing method of a polyester resin (B) can take a well-known method similarly to the said polyester resin (A).
- the target polyester resin can be obtained by esterifying the above dicarboxylic acid and glycol components at 150 to 250 ° C., and then polycondensing at 230 to 300 ° C. under reduced pressure.
- a hydrophilic polar group is introduced, it is preferable to add a monovalent inorganic salt such as sodium acetate or potassium acetate as a polymerization stabilizer.
- the glass transition temperature of the polyester resin (B) is 40 to 90 ° C, preferably 45 to 85 ° C, more preferably 50 to 80 ° C. When it is less than the above value, blocking may occur when the laminated film is rolled up. When the above value is exceeded, melting may not occur at the heat seal temperature, and adhesiveness may be deteriorated.
- the reduced viscosity ( ⁇ sp / c) of the polyester resin (B) is preferably 0.1 to 1.0 dl / g. More preferably, it is 0.2 to 0.9 dl / g, and still more preferably 0.3 to 0.7 dl / g. If it is less than the above value, the mechanical properties may be insufficient and the blocking resistance may decrease.
- the reduced viscosity can be arbitrarily adjusted by changing the polymerization time and temperature of the polyester and the degree of reduced pressure during polymerization (in the case of reduced pressure polymerization).
- the reduced viscosity is a value measured using an Ubbelohde viscosity tube at a sample concentration of 0.125 g / 25 ml, a measurement solvent chloroform and a measurement temperature of 25 ° C.
- the acid value of the polyester resin (B) is preferably 50 mgKOH / g or less, more preferably 40 mgKOH / g or less, and further preferably 30 mgKOH / g or less.
- the lower limit is not particularly limited, and may be 0 mgKOH / g, but is preferably 0.1 mgKOH / g or more, more preferably 0.5 mgKOH / g or more.
- the number average molecular weight (Mn) of the polyester resin (B) is preferably 2000 to 35000. More preferably, it is 5000-30000, and more preferably 10,000-25000. If it is less than the above value, the mechanical properties may be insufficient and the blocking resistance may decrease.
- the number average molecular weight can be arbitrarily adjusted by changing the polymerization time and temperature of the polyester, and the degree of reduced pressure during polymerization (in the case of reduced pressure polymerization).
- the number average molecular weight is a value measured by gel permeation chromatography (hereinafter, GPC, standard substance: polystyrene resin, mobile phase: tetrahydrofuran).
- the content of the polyester resin (B) in the adhesive composition is preferably 10 to 150 parts by weight, more preferably 18 to 120 parts by weight, and still more preferably 100 parts by weight of the polyester resin (A). Is 25 to 100 parts by mass. If the above value is exceeded, blocking may occur when the laminated film is rolled up. If it is less than the above value, the resin does not have flexibility at the time of peeling at room temperature, and the adhesiveness may decrease.
- polyester resin (B) is a polyester resin within the above glass transition temperature, it can be used alone or in combination of two or more.
- antifogging agent (C) is not particularly limited as long as it imparts antifogging properties.
- an anionic surfactant, nonionic surfactant, cationic surfactant, or amphoteric A surfactant or the like can be used.
- a nonionic surfactant it is preferable to use a nonionic surfactant.
- anti-fogging property refers to the ability to prevent fogging of the inner surface of the packaging material (including the lid material) with water that evaporates when water is poured into the packaging container and sealed with the lid material.
- lids for packaging containers for fresh foods such as vegetables and fruits may become difficult to see the contents due to transpiration of moisture, and the product value may be reduced, so an excellent anti-fogging performance may be required. .
- anionic surfactants include higher alcohol sulfates, higher alkyl sulfonates, higher carboxylates, alkyl benzene sulfonates, polyoxyethylene alkyl sulfate salts, polyoxyethylene alkyl phenyl ether sulfates. Salt, vinyl sulfosuccinate.
- Nonionic surfactants include polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyethylene glycol fatty acid ester, ethylene oxide propylene oxide block copolymer, polyoxyethylene fatty acid amide, ethylene oxide-propylene oxide copolymer, etc. And a compound having a polyoxyethylene structure and a sorbitan derivative.
- Examples of the cationic surfactant include alkylamine salts, dialkylamine salts, trialkylamine salts, alkyltrimethylammonium chloride, dialkyldimethylammonium chloride, and alkylbenzalkonium chloride.
- Examples of amphoteric surfactants include lauryl betaine and lauryl dimethylamine oxide.
- nonionic surfactants include sorbitan monostearate, sorbitan distearate, sorbitan monopalmitate, sorbitan dipalmitate, sorbitan monobehenate, sorbitan dibehenate, sorbitan monolaurate, sorbitan dilaurate Sorbitan surfactants such as: glycerol monolaurate, glycerol dilaurate, diglycerol monopalmitate, diglycerol dipalmitate, glycerol monostearate, glycerol distearate, diglycerol monostearate, diglycerol distearate, Glycerin surfactants such as diglycerin monolaurate and diglycerin dilaurate; polyethylenes such as polyethylene glycol monostearate and polyethylene glycol monopalinate Lenglycol surfactants; trimethylolpropane surfactants such as trimethylolpropane monostearate; diethanolalkyl
- cationic surfactant examples include amine salts such as laurylamine acetate, triethanolamine monoformate, stearamide ethyl diethylamine acetate, lauryltrimethylammonium chloride, stearyltrimethylammonium chloride, dilauryldimethylammonium chloride. And quaternary ammonium salts such as distearyldimethylammonium chloride, lauryldimethylbenzylammonium chloride, and stearyldimethylbenzylammonium chloride. These may be used alone or in combination of two or more.
- the content ratio of the antifogging agent (C) in the adhesive composition is preferably 0.1 to 50 parts by mass, more preferably 0.5 to 38 parts by mass with respect to 100 parts by mass of the polyester resin (A). More preferably, it is 1 to 25 parts by mass, particularly preferably 2 to 20 parts by mass, and most preferably 3 to 15 parts by mass. If it is less than the above value, the influence on the surface of the adhesive layer is small and the antifogging effect may be insufficient. When the above value is exceeded, the antifogging agent may remain excessively on the surface of the adhesive layer, and the adhesiveness may be lowered.
- the adhesive composition of the present invention is a composition containing the polyester resin (A) and the antifogging agent (C) as essential components, and preferably further contains a polyester resin (B).
- the total amount of the polyester resin (A) and the polyester resin (B) is preferably 80% by mass or more, more preferably 90% by mass or more, and further preferably 95% by mass. This is the above, and it may be 100% by mass.
- the antifogging agent (C) is 0.1 to 20 parts by mass with respect to 100 parts by mass in total of the polyester resin (A) and the polyester resin (B) of the adhesive composition. More preferred is 0.5 to 15 parts by mass, and even more preferred is 1 to 10 parts by mass. If it is less than the above value, the influence on the surface of the adhesive layer is small and the antifogging effect may be insufficient. When the above value is exceeded, the antifogging agent may remain excessively on the surface of the adhesive layer, and the adhesiveness may be lowered.
- the adhesive composition of the present invention can contain an antiblocking agent (D).
- the anti-blocking agent (D) include inorganic particles, organic particles, or waxes, and the anti-blocking agent (D) can be contained to such an extent that adhesion and blocking resistance are not deteriorated.
- These antiblocking agents (D) can be used alone or in combination of two or more.
- it contains an antiblocking agent (D) it is preferable that it is 0.1 mass part or more with respect to 100 mass parts of polyester resins (A), More preferably, it is 0.2 mass part or more. If the amount is too small, the effect of blocking resistance may not be exhibited. Moreover, it is preferable that it is 5 mass parts or less, More preferably, it is 3 mass parts or less. If the amount is too large, the adhesiveness may decrease or the transparency may decrease.
- the inorganic particles include inorganic oxides including metal oxides such as magnesium, calcium, barium, zinc, zirconium, molybdenum, silicon, antimony, and titanium, hydroxides, sulfates, carbonates, or silicates. Particles. Among these inorganic particles, silica gel particles are particularly preferable.
- the shape of the particles may be any shape such as powder, granule, granule, flat plate, and needle, and is not limited.
- the organic particles include polymer particles such as polymethyl methacrylate resin, polystyrene resin, nylon resin, melamine resin, benzoguanamine resin, phenol resin, urea resin, silicon resin, methacrylate resin, or acrylate resin, or cellulose powder, nitrocellulose. Examples include powder, wood powder, waste paper powder, rice husk powder, and starch.
- the polymer particles can be obtained by a polymerization method such as emulsion polymerization, suspension polymerization, dispersion polymerization, soap-free polymerization, or microsuspension polymerization.
- the organic particles can be used as long as the effects of the present invention are not impaired.
- the shape of the particles may be any shape such as powder, granule, granule, flat plate, and needle, and is not limited.
- waxes include liquid wax, natural paraffin, micro wax, synthetic paraffin, hydrocarbon waxes such as polyethylene wax, fatty acid waxes such as stearic acid, stearic acid amide, palmitic acid amide, and methylene bisstearo.
- Fatty acid amide waxes such as amide, ethylenebisstearoamide, oleic acid amide, esylic acid amide, lower alcohol esters of fatty acids, polyhydric alcohol esters of fatty acids, fatty acid polyglycol esters, etc.
- waxes cetyl alcohol, stearyl alcohol And other natural waxes such as alcohol waxes, olefin waxes, castor waxes, carnauba waxes, and soaps derived from fatty acids having 12 to 30 carbon atoms.
- the waxes can be used as long as the effects of the present invention are not impaired.
- the laminated film of the present invention is a film in which an adhesive layer made of the adhesive composition of the present invention is laminated on at least one surface of a base film.
- the laminated film can be produced by various methods such as co-extrusion, extrusion coating, or solvent coating of a base film and an adhesive composition.
- the base film is not particularly limited as long as it can form an adhesive layer from the adhesive composition of the present invention, but a thermoplastic resin film is preferable, for example, a polyester resin film, a polypropylene resin, and the like.
- a thermoplastic resin film for example, a polyester resin film, a polypropylene resin, and the like.
- examples thereof include a film, a polyamide-based resin film, a polyvinyl alcohol-based resin film, and a polyvinylidene chloride-based resin film.
- a polyester-type resin film is more preferable.
- the thickness of the base film is preferably 5 ⁇ m or more, more preferably 10 ⁇ m or more. If it is less than the above value, the durability of the substrate film may be insufficient. Moreover, it is preferable that it is 50 micrometers or less, More preferably, it is 30 micrometers or less. If the above value is exceeded, it may become impractical as a lid for food packaging containers.
- the solvent for dissolving the adhesive composition of the present invention is not particularly limited, and can be arbitrarily selected in consideration of solubility, volatility, drying speed, leveling properties, environmental impact, etc. It is.
- the organic solvent include aromatic hydrocarbon solvents such as toluene, xylene, and solvesso, ester solvents such as ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, and isobutyl acetate, acetone, and methyl ethyl ketone (hereinafter also referred to as MEK).
- Ketone solvents such as cyclohexanone, alcohol solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl Glycol ether solvents such as ether, and milk such as glycol ether ester solvents, ethyl lactate, methyl lactate, etc., which are acetyl esterified from these. And ester-based solvents.
- the solvent can be used alone or in combination of two or more.
- a laminated film can be obtained by coating (coating) an organic solvent solution of the adhesive composition on a base film and drying.
- the thickness of the adhesive layer is preferably 1 ⁇ m or more, more preferably 2 ⁇ m or more. Adhesiveness may become inadequate that it is less than the said value. Moreover, it is preferable that it is 10 micrometers or less, More preferably, it is 5 micrometers or less. When the above value is exceeded, the heat sealability may deteriorate.
- the laminated film of the present invention is excellent in adhesiveness and antifogging property, it is suitable as a constituent component of a packaging material. Especially, it is suitable as a lid
- a food packaging container It is preferable that it is a polyester-type resin.
- Crystal melting point and glass transition temperature Using a differential scanning calorimeter (DSC) DSC-220 manufactured by Seiko Instruments Inc., 5 mg of a sample (polyester resin (A) or polyester resin (B)) is sealed in an aluminum presser lid type container. Then, the temperature was measured from ⁇ 100 ° C. to 250 ° C. at a rate of temperature increase of 20 ° C./min, and the maximum peak temperature of heat of fusion was determined as the crystalline melting point. In addition, the glass transition temperature is determined by the temperature at the intersection of the base line extension below the glass transition temperature and the tangent indicating the maximum slope from the peak rising portion to the peak apex under the same conditions as in the measurement apparatus. It was.
- DSC differential scanning calorimeter
- peel strength (adhesiveness)
- the adhesive layer surface of the laminated film for evaluation was heat-sealed for 1 second at a temperature of 130 ° C. and a pressure of 2.8 kgf / cm 2 on a 350 ⁇ m thick amorphous polyester sheet (A-PET sheet manufactured by Toyobo Co., Ltd.). Thereafter, a test piece having a width of 25 mm was cut out, and a 180 ° peel test was conducted at 25 ° C. at a tensile speed of 100 mm / min, and the peel strength was measured.
- a test sample was prepared by superimposing the adhesive layer surface of the evaluation laminated film on the untreated corona surface of a polyester film (Toyobo Co., Ltd., E5107). Then, it stored for 1 day under the pressure of 40 kg and 0.9 kgf / cm ⁇ 2 >, and the blocking resistance was confirmed with the following criteria.
- ⁇ Evaluation criteria> ⁇ : There was no tack of the test sample. (Triangle
- X The test sample had tack and was in a range causing problems in use.
- polyester resin (A) Synthesis of polyester resin (A-1) 445 parts by mass of terephthalic acid, isophthalic acid in a reaction can equipped with a stirrer, a thermometer, a heater, a cooling device, and a condenser for distillation 74 parts by mass, 270 parts by mass of sebacic acid, 277 parts by mass of ethylene glycol, 465 parts by mass of propylene glycol and 0.5 parts by mass of tetrabutyl titanate were charged, and the esterification reaction was carried out over 4 hours while raising the temperature to 230 ° C. .
- the pressure in the system was reduced to 10 torr over 60 minutes while the temperature was raised to 250 ° C., and the pressure was further reduced to 1 torr or less, and a polycondensation reaction was performed at 250 ° C. for 60 minutes. Thereafter, the polycondensation reaction was terminated by flowing nitrogen into the system and breaking the vacuum. After completion of the reaction, the polyester resin was taken out and cooled to obtain a polyester resin (A-1).
- Example of Polyester Resin (B) Synthesis of Polyester Resin (B-1)
- a reaction can equipped with a stirrer, thermometer, heater, cooling device, and distillation cooler, 455 parts by mass of dimethyl terephthalate, isophthalate 455 parts by weight of dimethyl acid, 291 parts by weight of ethylene glycol, 488 parts by weight of 2,2-dimethyl-1,3-propanediol and 0.5 parts by weight of tetrabutyl titanate were added over 4 hours while raising the temperature to 240 ° C. An esterification reaction was performed.
- the pressure in the system was reduced to 10 torr over 60 minutes while the temperature was raised to 250 ° C., and the pressure was further reduced to 1 torr or less under vacuum to carry out a polycondensation reaction at 250 ° C. for 60 minutes. Thereafter, the polycondensation reaction was terminated by flowing nitrogen into the system and breaking the vacuum. After completion of the reaction, the polyester resin was taken out and cooled to obtain a polyester resin (B-1).
- polyester resins (A-2) to (A-5) and (B-2) to (B-4) were synthesized from A-5).
- the measurement results of the resin physical properties are shown in Table 1.
- antifogging agent (C) As the antifogging agent (C), a nonionic surfactant [Riquemar (registered trademark) manufactured by Riken Vitamin Co., Ltd.] DO-100V, A, OL-100E was used.
- SYLOID registered trademark
- GRACE which is amorphous silica
- Example 1 80 parts by mass of a polyester resin (A-1), 20 parts by mass of a polyester resin (B-1), 5 parts by mass of an antifogging agent (C) and 1 part by mass of an antiblocking agent (D) are heated and stirred in a MEK solution. Adhesive composition 1 was produced. Table 2 shows the blending amount, peel strength, antifogging property, and blocking resistance.
- Examples 2 to 13 The polyester resin, the antifogging agent and the antiblocking agent were changed as shown in Table 2, and Examples 2 to 13 were performed in the same manner as in Example 1.
- Table 2 shows the peel strength, antifogging property, and blocking resistance.
- Comparative Examples 1 to 3 were carried out in the same manner as in Example 1, except that the polyester resin, the antifogging agent and the antiblocking agent were changed as shown in Table 3.
- Table 3 shows the peel strength, antifogging property, and blocking resistance.
- Examples 1 to 6, 9, 12, and 13 have anti-fogging properties and anti-blocking properties while having excellent adhesive properties as adhesives. Moreover, although Examples 7, 8, and 11 are inferior to blocking property, they have excellent adhesiveness and antifogging property. Further, Example 10 has excellent adhesion and blocking resistance, although the anti-fogging property decreases.
- Comparative Example 1 the glass transition temperature of the polyester resin A is high and the peel strength is low. In Comparative Example 2, since no antifogging agent is blended, the antifogging property is inferior. In Comparative Example 3, since the polyester resin A is not blended, the peel strength is low.
- the adhesive composition according to the present invention and a laminated film using the adhesive composition are excellent in adhesiveness to a base material and have blocking resistance when heat-sealed as a lid for a packaging container. Furthermore, since antifogging property is favorable, it can be used suitably as packaging materials, such as fresh food.
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Abstract
Description
たとえば、特許文献1では、オレフィン系樹脂とポリエステル系樹脂とを積層してなる少なくとも4層の多層フィルムであって、防曇剤の練り込みを行う層を選択すると共に、多層フィルムの表面処理を適切に行うことによって得られる多層フィルムが提案されている。
また、特許文献2では、樹脂をフィルム状に成形したのちに、内容物に接する面に防曇剤を塗布する方法が提案されている。
(1)ポリエステル樹脂(A)のガラス転移温度が-30~30℃である。
(2)ポリエステル樹脂(B)のガラス転移温度が40~90℃である。
本発明で用いるポリエステル樹脂(A)は、2価以上の多価カルボン酸化合物からなるカルボン酸成分と、2価以上の多価アルコール化合物からなるアルコール成分とが重縮合して得られる化学構造のポリエステルであることや、ヒドロキシカルボン酸やラクトンを共重合したものであることが好ましい。2価以上の多価カルボン酸化合物からなるカルボン酸成分と、2価以上の多価アルコール化合物からなるアルコール成分とが重縮合して得られる化学構造のポリエステルの場合は、多価カルボン酸化合物および多価アルコール化合物の少なくとも一方が2種類以上の成分からなる共重合ポリエステル樹脂であることが好ましい。また、多価カルボン酸化合物および多価アルコール化合物は、主としてジカルボン酸成分とグリコール成分からなる共重合ポリエステル樹脂であることが好ましい。ここで主としては、本発明に用いるポリエステル樹脂(A)を構成する全酸成分と全アルコール成分の合計200モル%に対して、ジカルボン酸成分とグリコール成分の合計がモル基準で100モル%以上を占めることを指す。ジカルボン酸成分とグリコール成分の合計は140モル%以上であることが好ましく、170モル%以上であることがより好ましく、190モル%以上であることがさらに好ましく、200モル%であっても差し支えない。
本発明の接着剤組成物にポリエステル樹脂(B)を配合することで、接着性および防曇性のみならず、優れた耐ブロッキング性を発現することができる。すなわち、接着剤組成物からなる接着剤層を基材フィルムに積層した積層フィルムをロール状にした際に優れた耐ブロッキング性を発現することができる。
防曇剤(C)としては、防曇性を付与するものであれば、とくに限定されるものではなく、例えば、アニオン性界面活性剤、ノニオン性界面活性剤、カチオン性界面活性剤、または両性界面活性剤等を使用することができる。なかでもノニオン性界面活性剤を用いることが好ましい。ここで防曇性とは、包装容器に水を入れて蓋材でシールしたときに、蒸散する水分で包装材内表面(蓋材を含む)の曇りを防止する性能をいう。特に、野菜やフルーツなどの生鮮食品の包装容器の蓋材は、水分の蒸散により内容物が見えにくくなり、商品価値が低下することがあるため、優れた防曇性能が必要となることがある。
本発明の接着剤組成物は、前記ポリエステル樹脂(A)および防曇剤(C)を必須成分として含有する組成物であり、さらにポリエステル樹脂(B)を含有することが好ましい。ポリエステル樹脂(B)を配合する場合、ポリエステル樹脂(A)とポリエステル樹脂(B)の配合比(質量比)は、ポリエステル樹脂(A)/ポリエステル樹脂(B)=90~40/10~60であることが好ましく、より好ましくは85~45/15~55であり、さらに好ましくは80~50/20~50である。ポリエステル樹脂(B)が少なすぎると積層フィルムをロール状に巻き取った際に、ブロッキングが発生する場合がある。一方、ポリエステル樹脂(B)が多すぎると、室温での剥離時に樹脂の柔軟性がなく、接着性が低下する場合がある。
本発明の接着剤組成物には、アンチブロッキング剤(D)を含有することができる。アンチブロッキング剤(D)としては無機粒子、有機粒子、またはワックス類などが挙げられ、接着性、耐ブロッキング性を落とさない程度で含有することができる。これらアンチブロッキング剤(D)は単独で、または2種以上を併用することができる。アンチブロッキング剤(D)を含有する場合は、ポリエステル樹脂(A)100質量部に対して、0.1質量部以上であることが好ましく、より好ましくは0.2質量部以上である。少なすぎると耐ブロッキング性の効果を発現しないことがある。また、5質量部以下であることが好ましく、より好ましくは3質量部以下である。多すぎると接着性が低下したり、透明性が低下することがある。
本発明の積層フィルムは、基材フィルムの少なくとも片面に、本発明の接着剤組成物からなる接着剤層を積層したフィルムである。積層フィルムは基材フィルムと接着剤組成物とを共押出、押出コート、または溶剤コートなど各種の方法で製造することができる。
以下、実施例を挙げて本発明を更に詳細に説明する。但し、本発明は実施例に限定されない。実施例中および比較例中に単に部とあるのは質量部を示す。
セイコーインスツルメンツ(株)製示差走査熱量分析計(DSC)DSC-220を用いて、アルミニウム押え蓋型容器にサンプル(ポリエステル樹脂(A)またはポリエステル樹脂(B))5mgを密封し、-100℃から250℃まで、20℃/分の昇温速度で測定し、融解熱の最大ピーク温度を結晶融点として求めた。また、ガラス転移温度は、前記測定装置、同様条件でガラス転移温度以下のベースラインの延長線とピークの立ち上がり部分からピークの頂点までの間での最大傾斜を示す接線との交点の温度で求めた。
実施例、比較例で得られた接着剤組成物を厚さ25μmのポリエステルフィルム(東洋紡株式会社製、E5107)のコロナ処理面に、乾燥後の厚みが3g/cm2となるように塗布した。次いで160℃で30秒乾燥し、評価用積層フィルムを得た。
評価用積層フィルムの接着剤層面を、厚さ350μmアモルファスポリエステルシート(東洋紡株式会社製A-PETシート)に、温度130℃、圧力2.8kgf/cm2で、1秒間ヒートシールした。その後、25mm幅の試験片を切り取り、25℃において、引張速度100mm/minで180°剥離試験を行い、剥離強度を測定した。
<評価基準>
◎:1000gf/25mm以上
○:800gf/25mm以上1000gf/25mm未満
△:500gf/25mm以上800gf/25mm未満
×:500gf/25mm未満
容量70cm3の容器に60℃の水30mlを入れて、積層フィルムの接着剤層面を容器の口部に合わせ、輪ゴムで蓋をした。その後、60℃の恒温槽で1時間保管し、目視にて以下の判定基準により防曇効果を確認した。
<評価基準>
○:フィルム表面に連続的な水膜が形成され、視認性良好であった。
△:フィルム表面に一部水滴付着したが、視認性良好であった。
×:フィルム表面に水滴付着が有った、または視認性が悪化した。
容量70cm3の容器に常温の水30mlを入れて、積層フィルムの接着剤層面を容器の口部に合わせ、輪ゴムで蓋をした。その後、5℃の恒温槽で1日保管し、目視にて以下の判定基準により防曇効果を確認した。
<評価基準>
○:フィルム表面に連続的な水膜が形成され、視認性良好であった。
△:フィルム表面に一部水滴付着したが、視認性良好であった。
×:フィルム表面に水滴付着が有った、または視認性が悪化した。
評価用積層フィルムの接着剤層面をポリエステルフィルム(東洋紡株式会社製、E5107)のコロナ未処理面に重ね合わせ試験サンプルを作製した。その後、40℃、0.9kgf/cm2の圧力下で1日保管し、以下の判定基準により耐ブロッキング性を確認した。
<評価基準>
○:試験サンプルのタックが全く無かった。
△:試験サンプルにわずかにタックがあるものの、使用上問題にならない範囲であった。
×:試験サンプルにタックがあり、使用上問題となる範囲であった。
ポリエステル樹脂(A-1)の合成
撹拌機、温度計、加熱ヒーター、冷却装置、溜出用冷却器を装備した反応缶内に、テレフタル酸445質量部、イソフタル酸74質量部、セバシン酸270質量部、エチレングリコール277質量部、プロピレングリコール465質量部およびテトラブチルチタネート0.5質量部を仕込み、230℃まで昇温しつつ4時間かけてエステル化反応を行った。エステル交換反応終了後、系内を250℃まで昇温しながら60分かけて10torrまで減圧し、さらに1torr以下の真空下まで減圧して250℃で60分間重縮合反応を行った。その後、系内に窒素を流し、真空破壊することで重縮合反応を終了させた。反応終了後、ポリエステル樹脂を取り出し、冷却することによりポリエステル樹脂(A-1)を得た。
ポリエステル樹脂(B-1)の合成
撹拌機、温度計、加熱ヒーター、冷却装置、溜出用冷却器を装備した反応缶内に、テレフタル酸ジメチル455質量部、イソフタル酸ジメチル455質量部、エチレングリコール291質量部、2,2-ジメチル-1,3-プロパンジオール488質量部およびテトラブチルチタネート0.5質量部を仕込み、240℃まで昇温しつつ4時間かけてエステル化反応を行った。エステル化反応終了後、系内を250℃まで昇温しながら60分かけて10torrまで減圧し、さらに1torr以下の真空下まで減圧して250℃で60分間重縮合反応を行った。その後、系内に窒素を流し、真空破壊することで重縮合反応を終了させた。反応終了後、ポリエステル樹脂を取り出し、冷却することによりポリエステル樹脂(B-1)を得た。
ポリエステル樹脂(A-1)の合成例と同様に、ポリエステル樹脂(A-2)~(A-5)を、ポリエステル樹脂(B-1)の合成例と同様に、ポリエステル樹脂(B-2)~(B-4)を合成した。樹脂物性の測定結果を表1に示す。
ポリエステル樹脂(A-1)80質量部とポリエステル樹脂(B-1)20質量部と防曇剤(C)5質量部とアンチブロッキング剤(D)1質量部をMEK溶液中で加熱撹拌し、接着剤組成物1を作製した。配合量、剥離強度、防曇性、耐ブロッキング性を表2に示す。
ポリエステル樹脂および防曇剤、アンチブロッキング剤を表2に示すとおりに変更し、実施例1と同様な方法で実施例2~13を行った。剥離強度、防曇性、耐ブロッキング性を表2に示す。
ポリエステル樹脂および防曇剤、アンチブロッキング剤を表3に示すとおりに変更し、実施例1と同様な方法で比較例1~3を行った。剥離強度、防曇性、耐ブロッキング性を表3に示す。
Claims (11)
- ポリエステル樹脂(A)および防曇剤(C)を含有し、かつ下記(1)を満足する接着剤組成物。
(1)ポリエステル樹脂(A)のガラス転移温度が-30~30℃である。 - さらにポリエステル樹脂(B)を含有し、かつ下記(2)を満足する請求項1に記載の接着剤組成物。
(2)ポリエステル樹脂(B)のガラス転移温度が40~90℃である。 - 防曇剤(C)がノニオン性界面活性剤である請求項1または2に記載の接着剤組成物。
- ポリエステル樹脂(A)100質量部に対して、防曇剤(C)を0.1~50質量部含有する請求項1~3のいずれかに記載の接着剤組成物。
- ポリエステル樹脂(A)100質量部に対して、ポリエステル樹脂(B)を10~150質量部含有する請求項2~4のいずれかに記載の接着剤組成物。
- 請求項1~5のいずれかに記載の接着剤組成物からなる接着剤層と熱可塑性樹脂フィルムとを積層してなることを特徴とする積層フィルム。
- 請求項6に記載の熱可塑性フィルムがポリエステル系樹脂フィルムであることを特徴とする積層フィルム。
- 接着剤層の厚みが1~10μmの範囲である請求項6または7に記載の積層フィルム。
- 請求項8に記載の積層フィルムを構成部材とすることを特徴とする包装材。
- 請求項9に記載の包装材を構成部材とする食品包装容器の蓋材。
- 請求項10に記載の蓋材とポリエステル系樹脂を積層してなることを特徴とする食品包装容器。
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US16/466,679 US11459492B2 (en) | 2017-03-29 | 2018-01-17 | Adhesive composition having anti-fogging property |
CN201880020840.0A CN110461983B (zh) | 2017-03-29 | 2018-01-17 | 具有防雾性的粘合剂组合物 |
KR1020197022311A KR102404967B1 (ko) | 2017-03-29 | 2018-01-17 | 방담성을 갖는 접착제 조성물 |
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WO2021166882A1 (ja) * | 2020-02-17 | 2021-08-26 | 東洋紡株式会社 | 結晶性ポリエステル樹脂及びそれを用いた接着剤組成物 |
WO2023063091A1 (ja) * | 2021-10-14 | 2023-04-20 | Dic株式会社 | 防曇性多層フィルム、これを用いる積層体、及び包装材 |
WO2023127593A1 (ja) * | 2021-12-28 | 2023-07-06 | 東洋紡株式会社 | 積層フィルム、食品包装容器用蓋材および食品包装容器 |
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WO2021166882A1 (ja) * | 2020-02-17 | 2021-08-26 | 東洋紡株式会社 | 結晶性ポリエステル樹脂及びそれを用いた接着剤組成物 |
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US11459492B2 (en) | 2022-10-04 |
EP3561019B1 (en) | 2022-01-05 |
KR20190127675A (ko) | 2019-11-13 |
CN110461983A (zh) | 2019-11-15 |
JP7067547B2 (ja) | 2022-05-16 |
EP3561019A4 (en) | 2020-06-24 |
TWI782957B (zh) | 2022-11-11 |
ES2904943T3 (es) | 2022-04-06 |
US20200063006A1 (en) | 2020-02-27 |
JPWO2018179689A1 (ja) | 2020-02-06 |
CN110461983B (zh) | 2022-03-18 |
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EP3561019A1 (en) | 2019-10-30 |
TW201840795A (zh) | 2018-11-16 |
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