WO2025027993A1 - 多層容器、リサイクルポリアミド樹脂の製造方法、および、多層容器の製造方法 - Google Patents

多層容器、リサイクルポリアミド樹脂の製造方法、および、多層容器の製造方法 Download PDF

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Publication number
WO2025027993A1
WO2025027993A1 PCT/JP2024/019335 JP2024019335W WO2025027993A1 WO 2025027993 A1 WO2025027993 A1 WO 2025027993A1 JP 2024019335 W JP2024019335 W JP 2024019335W WO 2025027993 A1 WO2025027993 A1 WO 2025027993A1
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Prior art keywords
multilayer body
polyamide resin
sealant layer
multilayer
mass
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PCT/JP2024/019335
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English (en)
French (fr)
Japanese (ja)
Inventor
拓海 山田
浩介 大塚
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Mitsubishi Gas Chemical Co Inc
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Mitsubishi Gas Chemical Co Inc
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Priority to CN202480049476.6A priority Critical patent/CN121586644A/zh
Priority to JP2025537686A priority patent/JPWO2025027993A1/ja
Publication of WO2025027993A1 publication Critical patent/WO2025027993A1/ja
Anticipated expiration legal-status Critical
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    • 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
    • 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
    • B32B27/34—Layered products comprising a layer of synthetic resin comprising polyamides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D29/00—Sacks or like containers made of fabrics; Flexible containers of open-work, e.g. net-like construction
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D65/00—Wrappers or flexible covers; Packaging materials of special type or form
    • B65D65/38—Packaging materials of special type or form
    • B65D65/40—Applications of laminates for particular packaging purposes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/80—Packaging reuse or recycling, e.g. of multilayer packaging

Definitions

  • the present invention relates to a multi-layer container, a method for producing recycled polyamide resin, and a method for producing a multi-layer container.
  • the present invention relates to a multi-layer container whose main component is polyamide resin.
  • Packaging materials used to package foods and other foods are required to have a wide range of functions, such as strength, pinhole resistance, heat resistance, and visibility of the contents, in order to protect the contents from various distribution processes and processes such as heat sterilization.
  • barrier properties are also required to prevent the penetration of oxygen and moisture.
  • multilayer containers in which layers with different properties are stacked are used (Patent Document 1, Patent Document 2, etc.).
  • multi-layer containers are difficult to separate the resins that make up each layer, making them unsuitable for recycling.
  • multi-layer containers could be made of a single material or a composition close to that.
  • films using polyamide resins have excellent heat resistance, strength, and oxygen gas barrier properties, but polyamide resins tend to have poor heat sealability, and since a resin other than polyamide resin is required for the sealant layer, it is difficult to make them from a single material.
  • aromatic polyamide resins are used, the impact resistance of the film is not sufficient.
  • the present invention aims to solve these problems, and to provide a multilayer container that has excellent recyclability, heat sealability, and impact resistance, as well as a method for producing a recycled polyamide resin and a method for producing a multilayer container.
  • the present inventors have conducted research and have found that the above-mentioned problems can be solved by fusing a sealant layer containing an aromatic polyamide resin and a base layer containing an aliphatic polyamide resin to form a container, and further reducing the thickness of the sealant layer so that 95% by mass or more of the entire multilayer container is made of polyamide resin.
  • the above problems were solved by the following means.
  • a first multilayer body including a sealant layer containing a polyamide resin and a base layer containing an aliphatic polyamide resin;
  • a multi-layer container having a sealant layer containing a polyamide resin and a second multi-layer body including a base layer containing an aliphatic polyamide resin, the sealant layer of the first multilayer body and the sealant layer of the second multilayer body face each other and are partially fused to each other;
  • the thickness of the sealant layer of the first multilayer body and the thickness of the sealant layer of the second multilayer body are each independently 4 ⁇ m or more and 40% or less of the total thickness of the first multilayer body or the second multilayer body;
  • the polyamide resin contained in the sealant layer of the first multilayer body and the polyamide resin contained in the sealant layer of the second multilayer body are each independently a resin in which 30% by mass or more of all structural units excluding terminal groups are derived from an aromatic monomer, the aliphatic polyamide resin contained in the first multilayer body and the ali
  • Multi-layer container ⁇ 2> The multilayer container described in ⁇ 1>, wherein the first multilayer body and the second multilayer body each independently have a moisture content of 10,000 mass ppm or less immediately before sealing. ⁇ 3> The multilayer container according to ⁇ 1> or ⁇ 2>, wherein the sealant layer of the first multilayer body and the sealant layer of the second multilayer body each independently have a thickness of 6 ⁇ m or more.
  • ⁇ 4> The multilayer container according to any one of ⁇ 1> to ⁇ 3>, wherein the polyamide resin contained in the sealant layer of the first multilayer body and the polyamide resin contained in the sealant layer of the second multilayer body each independently contain a diamine-derived structural unit and a dicarboxylic acid-derived structural unit, and 70 mol % or more of the diamine-derived structural units contain a xylylenediamine-based polyamide resin derived from xylylenediamine.
  • ⁇ 5> The multilayer container according to ⁇ 4>, wherein 70 mol % or more of the dicarboxylic acid-derived structural units in the xylylenediamine-based polyamide resin are structural units derived from an ⁇ , ⁇ -linear aliphatic dicarboxylic acid having 4 to 20 carbon atoms.
  • the first multilayer body and the second multilayer body each independently have a moisture content of 10,000 ppm by mass or less immediately before sealing, the sealant layer of the first multilayer body and the sealant layer of the second multilayer body each independently have a thickness of 6 ⁇ m or more;
  • the polyamide resin contained in the sealant layer of the first multilayer body and the polyamide resin contained in the sealant layer of the second multilayer body each independently contain a diamine-derived structural unit and a dicarboxylic acid-derived structural unit, and 70 mol % or more of the diamine-derived structural units comprise a xylylenediamine-based polyamide resin derived from xylylenediamine;
  • the multilayer container according to any one of ⁇ 1> to ⁇ 5>, wherein 70 mol % or more of the constitutional units derived from the dicarboxylic acid are constitutional units derived from an ⁇ , ⁇ -linear aliphatic dicarboxylic acid having 4 to 20 carbon atoms.
  • ⁇ 7> The multilayer container according to any one of ⁇ 1> to ⁇ 6>, wherein in at least one of the first multilayer body and the second multilayer body, a sealant layer and a base layer are in contact directly or via an adhesive layer, and the sealant layer is an unstretched film.
  • a method for producing a recycled polyamide resin, comprising crushing the multilayer container according to any one of ⁇ 1> to ⁇ 7>.
  • a method for producing a multilayer container comprising: a first multilayer body including a sealant layer containing a polyamide resin and a base layer containing an aliphatic polyamide resin; and a second multilayer body including a sealant layer containing a polyamide resin and a base layer containing an aliphatic polyamide resin, and partially fusing the first multilayer body and the second multilayer body including a sealant layer containing a polyamide resin and a base layer containing an aliphatic polyamide resin such that the sealant layer of the first multilayer body and the sealant layer of the second multilayer body face each other, the thickness of the sealant layer of the first multilayer body and the thickness of the sealant layer of the second multilayer body are each independently 4 ⁇ m or more and 40% or less of the total thickness of the first multilayer body or the second multilayer body; the polyamide resin contained in the sealant layer of the first multilayer body and the polyamide resin contained in the sealant layer of the second multilayer body are each independently a resin
  • the present invention makes it possible to provide a multilayer container that has excellent recyclability, excellent heat sealability, and excellent impact resistance, a method for producing recycled polyamide resin, and a method for producing a multilayer container.
  • FIG. 1 is a schematic cross-sectional view showing an example of a multilayer container of the present invention.
  • the present embodiment is an example for explaining the present invention, and the present invention is not limited to the present embodiment.
  • the word “to” is used to mean that the numerical values before and after it are included as the lower limit and upper limit.
  • various physical properties and characteristic values are those at 23° C. unless otherwise specified.
  • ppm means “mass ppm” unless otherwise specified. If the measurement methods, etc. described in the standards shown in this specification vary from year to year, they will be based on the standards as of January 1, 2023, unless otherwise specified. FIG. 1 may not correspond to the actual scale.
  • the multilayer container of the present embodiment is a multilayer container having a first multilayer body including a sealant layer containing a polyamide resin and a substrate layer containing an aliphatic polyamide resin, and a second multilayer body including a sealant layer containing a polyamide resin and a substrate layer containing an aliphatic polyamide resin, wherein the sealant layer of the first multilayer body and the sealant layer of the second multilayer body face each other and are partially fused to each other, and the thickness of the sealant layer of the first multilayer body and the thickness of the sealant layer of the second multilayer body are each independently 4 ⁇ m or more and account for 40% or less of the total thickness of the first multilayer body or the second multilayer body.
  • the polyamide resin contained in the sealant layer of the first multilayer body and the polyamide resin contained in the sealant layer of the second multilayer body are each independently a resin having 30 mass% or more of all structural units excluding terminal groups derived from aromatic monomers
  • the aliphatic polyamide resin contained in the first multilayer body and the aliphatic polyamide resin contained in the second multilayer body are each independently a resin having 80 mass% or more of all structural units excluding terminal groups derived from aliphatic monomers
  • 95 mass% or more of the resin component contained in the multilayer container is polyamide resin.
  • the multilayer container of the present embodiment has a first multilayer body 1 and a second multilayer body 2, as shown in Fig. 1(a), for example.
  • the first multilayer body 1 has a sealant layer 12 containing an aromatic polyamide resin and a substrate layer 13 containing an aliphatic polyamide resin.
  • the second multilayer body 2 has a sealant layer 22 containing an aromatic polyamide resin and a substrate layer 23 containing an aliphatic polyamide resin.
  • the sealant layer of the first multilayer body and the sealant layer of the second multilayer body face each other and are partially fused (Fig. 1(b)). By fusing in this manner, it becomes possible to use it as a packaging container.
  • the sealant layer and the base layer are in direct contact with each other, but the sealant layer and the base layer may be in contact with each other via an adhesive layer.
  • the sealant layer and the base layer are in direct contact with each other without the adhesive layer.
  • the sealant layer and the base layer can be produced as a co-extruded body by co-extrusion, so that the sealant layer and the base layer can be bonded to each other without the use of an adhesive.
  • the multilayer body in this embodiment can be produced by utilizing known methods such as coextrusion, various lamination methods, and various coating methods depending on the properties of various materials, the purpose of processing, the processing step, etc., and the production method is not particularly limited.
  • the multilayer body can be produced by a method for laminating ordinary packaging materials, such as a wet lamination method, a dry lamination method, a solventless dry lamination method, an extrusion lamination method, a T-die coextrusion molding method, a coextrusion lamination method, an inflation method, etc.
  • a pretreatment such as a corona treatment or an ozone treatment, if necessary.
  • the adhesive layer is preferably an adhesive for dry lamination.
  • the adhesive for dry lamination include a one-liquid type that uses a urethane adhesive having an isocyanate group alone, and a two-liquid type urethane adhesive that uses a mixture of a base agent having a hydroxyl group and a curing agent having an isocyanate group, and the two-liquid type urethane adhesive is particularly preferred.
  • the adhesive layer preferably contains a thermoplastic resin having adhesive properties.
  • thermoplastic resin having adhesive properties examples include acid-modified polyolefin resins obtained by modifying polyolefin resins such as polyethylene or polypropylene with acids such as unsaturated carboxylic acids (acrylic acid, methacrylic acid, maleic acid, maleic anhydride, fumaric acid, itaconic acid, etc.), and polyester-based thermoplastic elastomers mainly composed of polyester-based block copolymers, and acid-modified polyolefin resins are preferred. More specifically, when a polypropylene-based polymer is used as the polyolefin resin, the resin contained in the adhesive layer may be an acid-modified polypropylene-based polymer.
  • the adhesive layer may also be an embodiment that does not contain a ternary copolymer of alkene-(meth)acrylic acid ester-unsaturated carboxylic acid.
  • the adhesive layer may be made of known anchor coating agents, adhesives, etc., such as isocyanate-based (urethane-based), polyethyleneimine-based, polybutadiene-based, and organic titanium-based anchor coating agents, or polyurethane-based, polyacrylic-based, polyester-based, epoxy-based, polyvinyl acetate-based, and cellulose-based lamination adhesives.
  • the adhesive layer may contain only one type of thermoplastic resin having adhesiveness, or may contain two or more types.
  • the total amount of the thermoplastic resin having adhesiveness in the adhesive layer is preferably 80% by mass or more, more preferably 90% by mass or more.
  • components other than the thermoplastic resin having adhesiveness contained in the adhesive layer include additives such as antioxidants, matting agents, weather stabilizers, ultraviolet absorbers, crystallization nucleating agents, plasticizers, flame retardants, and antistatic agents.
  • the thickness of the adhesive layer has a lower limit of preferably 2 ⁇ m or more, more preferably 3 ⁇ m or more.
  • the upper limit of the thickness is preferably 100 ⁇ m or less, more preferably 90 ⁇ m or less, even more preferably 50 ⁇ m or less, still more preferably 30 ⁇ m or less, even more preferably 10 ⁇ m or less, and may be 5 ⁇ m or less.
  • the substrate layer may be a stretched film or an unstretched film.
  • the sealant layer and the substrate layer are preferably bonded together using an adhesive.
  • the multilayer container of the present embodiment may have other layers within the scope of the present invention.
  • a design layer may be provided on the surface of the base layer.
  • the design layer is preferably also formed from a polyamide resin.
  • the thickness of the sealant layer of the first multilayer body and the thickness of the sealant layer of the second multilayer body are each independently 4 ⁇ m or more, preferably 5 ⁇ m or more, more preferably 6 ⁇ m or more, even more preferably 7 ⁇ m or more, and even more preferably 8 ⁇ m or more, and preferably 30 ⁇ m or less, more preferably 25 ⁇ m or less, even more preferably 23 ⁇ m or less, even more preferably 20 ⁇ m or less, even more preferably 19 ⁇ m or less, and even more preferably 10 ⁇ m or less.
  • the thickness equal to or greater than the lower limit, the heat seal strength tends to be improved. Also, by making the thickness equal to or less than the upper limit, the impact resistance and pinhole resistance tend to be improved.
  • the thickness ratio of the first sealant layer to the total thickness of the first multilayer body and the thickness ratio of the second sealant layer to the total thickness of the second multilayer body are each independently 40% or less. By adopting such a configuration, it is possible to compensate for the brittleness derived from the aromatic polyamide resin by the flexibility of the aliphatic polyamide substrate, and the flexibility and impact resistance of the multilayer container tend to be improved.
  • the thickness ratio of the first sealant layer to the total thickness of the first multilayer body and the thickness ratio of the second sealant layer to the total thickness of the second multilayer body are each independently preferably 35% or less, more preferably 32% or less, even more preferably 30% or less, even more preferably 28% or less, and even more preferably 27% or less.
  • the lower limit of the thickness ratio of the first sealant layer to the total thickness of the first multilayer body and the thickness ratio of the second sealant layer to the total thickness of the second multilayer body is preferably 1% or more, more preferably 2% or more, even more preferably 3% or more, even more preferably 6% or more, even more preferably 7% or more, even more preferably 9% or more, and may be 10% by mass or more.
  • the heat seal strength tends to be improved.
  • the thickness of the base layer of the first multilayer body and the thickness of the base layer of the second multilayer body are each independently 30 ⁇ m or more, more preferably 35 ⁇ m or more, even more preferably 40 ⁇ m or more, and even more preferably 45 ⁇ m or more, and preferably 180 ⁇ m or less, more preferably 140 ⁇ m or less, even more preferably 100 ⁇ m or less, even more preferably 80 ⁇ m or less, even more preferably 75 ⁇ m or less, and even more preferably 70 ⁇ m or less.
  • the thickness equal to or greater than the lower limit, the strength of the multilayer container is improved and the protection of the contents tends to be excellent. Also, by making the thickness equal to or less than the upper limit, the flexibility and impact resistance tend to be further improved.
  • the thickness of the body is preferably 20 ⁇ m or more, more preferably 30 ⁇ m or more, even more preferably 40 ⁇ m or more, even more preferably 45 ⁇ m or more, even more preferably 50 ⁇ m or more, even more preferably 55 ⁇ m or more, particularly preferably 60 ⁇ m or more, and even more particularly preferably 65 ⁇ m or more.
  • the thickness of the body is preferably 200 ⁇ m or less, more preferably 150 ⁇ m or less, even more preferably 100 ⁇ m or less, even more preferably 90 ⁇ m or less, even more preferably 85 ⁇ m or less, even more preferably 82 ⁇ m or less, and even more preferably 81 ⁇ m or less.
  • the first multilayer body and the second multilayer body in the multilayer body of this embodiment usually have one sealant layer and one substrate layer, but the sealant layer may be a multilayer body of two or more layers, and the substrate layer may be a multilayer body of two or more layers.
  • the sealant layer and/or the substrate layer is composed of two or more layers, the total thereof satisfies the above thickness and the desired composition.
  • the shape of the multi-layer container is not particularly limited, and may be, for example, a molded container such as a bottle, cup, tube, tray, or Tupperware, or a bag-like container such as a pouch, standing pouch, or zippered storage bag. In this embodiment, a pouch is preferred.
  • the capacity of the multi-layer container of this embodiment is preferably 0.01 to 2.0 L, more preferably 0.02 to 1.0 L, and even more preferably 0.03 to 0.5 L, in consideration of the preservation properties of the contents.
  • the items that can be stored in the multilayer container of this embodiment are not particularly limited, and examples include food, cosmetics, pharmaceuticals, toiletries, mechanical/electrical/electronic parts, oil, resins, etc., but it is particularly suitable for use as a container for storing food.
  • processed seafood products, processed livestock products, rice, and liquid foods can be mentioned.
  • it is suitable for preserving foods that are easily affected by oxygen.
  • JP 2011-37199 A the contents of which are incorporated herein by reference.
  • the food to be filled is not particularly limited, but specific examples include beverages such as vegetable juice, fruit juice, tea, coffee/coffee drinks, milk/dairy drinks, mineral water, ionic drinks, alcoholic drinks, lactic acid bacteria drinks, and soy milk; gel foods such as tofu, egg tofu, jellies, puddings, mizu yokan, mousse, yogurt, and almond tofu; seasonings such as sauce, soy sauce, ketchup, noodle soup, sauce, vinegar, mirin, dressing, jam, mayonnaise, miso, pickle base, and grated spices; salami, ham, sausage, yakitori, These include processed meat products such as meatballs, hamburgers, roast pork, and beef jerky; processed seafood products such as kamaboko, boiled shellfish, boiled fish, and chikuwa; processed rice products such as porridge, cooked rice, gomoku rice, and red rice; sauces such as meat sauce, mapo sauce, pasta sauce, curry, stew, and hayashi sauce; processed dairy
  • the first multilayer body and the second multilayer body in this embodiment each independently include a sealant layer containing an aromatic polyamide resin and a base layer containing an aliphatic polyamide resin.
  • the multilayer bodies each including such a sealant layer are fused (sealed) with the sealant layer portions facing each other to obtain a multilayer container.
  • the first multi-layer body and the second multi-layer body may be the same or different.
  • the sealant layers included in the first multilayer body and the second multilayer body each independently contain a polyamide resin.
  • the polyamide resin contained in the sealant layer contained in the first multilayer body and the second multilayer body is preferably a resin in which 30% by mass or more of all structural units excluding the terminal groups are derived from aromatic monomers, and preferably 40% by mass or more of all structural units excluding the terminal groups are derived from aromatic monomers, and more preferably 70% by mass or less of all structural units excluding the terminal groups are derived from aromatic monomers, and more preferably 60% by mass or less of all structural units excluding the terminal groups are derived from aromatic monomers.
  • Such a polyamide resin may be composed of only an aromatic polyamide resin, or may be a blend of an aromatic polyamide resin and an aliphatic polyamide resin.
  • 30% by mass or more of all constituent units excluding terminal groups may be constituent units derived from aromatic monomers.
  • aromatic polyamide resins examples include polyhexamethylene terephthalamide (polyamide 6T), polyhexamethylene isophthalamide (polyamide 6I), polyamide 66/6T, polyamide 9T, polyamide 9MT, polyamide 10T, polyamide 6I/6T, and xylylenediamine-based polyamide resins described below, with xylylenediamine-based polyamide resins being preferred.
  • the xylylenediamine-based polyamide resin in this embodiment is a polyamide resin that contains diamine-derived structural units and dicarboxylic acid-derived structural units, and in which 70 mol % or more of the diamine-derived structural units are derived from xylylenediamine.
  • the xylylenediamine-based polyamide resin for example, 50 mol % or more, preferably 70 mol % or more of the dicarboxylic acid-derived constitutional units are derived from an ⁇ , ⁇ -linear aliphatic dicarboxylic acid having 4 to 20 carbon atoms.
  • the strength and chemical resistance inherent to the xylylenediamine-based polyamide resin can be exhibited.
  • the diamine-derived structural units of the xylylenediamine-based polyamide resin are preferably 75 mol% or more, more preferably 80 mol% or more, even more preferably 85 mol% or more, even more preferably 90 mol% or more, even more preferably 95 mol% or more, and even more preferably 99 mol% or more derived from xylylenediamine (preferably paraxylylenediamine and/or metaxylylenediamine, more preferably metaxylylenediamine).
  • the dicarboxylic acid-derived structural units of the xylylenediamine-based polyamide resin are preferably 60 mol% or more, even more preferably 70 mol% or more, even more preferably 80 mol% or more, even more preferably 90 mol% or more, even more preferably 95 mol% or more, and even more preferably 99 mol% or more derived from an ⁇ , ⁇ -linear aliphatic dicarboxylic acid having 4 to 20 carbon atoms (preferably adipic acid).
  • the molar ratio of metaxylylenediamine and paraxylylenediamine in the xylylenediamine is preferably metaxylylenediamine/paraxylylenediamine is 00-100/100-0, more preferably 10-100/90-0, more preferably 40-100/60-0, even more preferably 60-100/40-0, even more preferably 80-100/20-0, and even more preferably 90-100/10-0.
  • Diamines other than metaxylylenediamine and paraxylylenediamine that can be used as raw diamine components for xylylenediamine-based polyamide resins include aliphatic diamines such as tetramethylenediamine, pentamethylenediamine, 2-methylpentanediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, dodecamethylenediamine, 2,2,4-trimethylhexamethylenediamine, and 2,4,4-trimethylhexamethylenediamine, and 1,3-bis Examples of such diamines include alicyclic diamines such as (aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 1,3-diaminocyclohexane, 1,4-diaminocyclohexane, bis(4-aminocyclohexyl
  • 50 mol % or more of the dicarboxylic acid-derived constitutional units are preferably derived from an ⁇ , ⁇ -straight-chain aliphatic dicarboxylic acid having 4 to 20 carbon atoms.
  • the number of carbon atoms in the ⁇ , ⁇ -straight-chain aliphatic dicarboxylic acid having 4 to 20 carbon atoms is preferably 6 or more, and is preferably 18 or less, more preferably 16 or less, even more preferably 14 or less, even more preferably 13 or less, even more preferably 12 or less, even more preferably 10 or less, and particularly preferably 8 or less.
  • Examples of ⁇ , ⁇ -linear aliphatic dicarboxylic acids having 4 to 20 carbon atoms that are preferably used as the raw dicarboxylic acid component of the xylylenediamine-based polyamide resin include aliphatic dicarboxylic acids such as succinic acid, glutaric acid, pimelic acid, suberic acid, azelaic acid, adipic acid, sebacic acid, undecanedioic acid, and dodecanedioic acid, and these can be used alone or in combination of two or more.
  • a preferred embodiment of the xylylenediamine-based polyamide resin in this embodiment is one in which 50 mol % or more (preferably 70 mol % or more, more preferably 90 mol % or more) of the constitutional units derived from dicarboxylic acid are derived from adipic acid.
  • Dicarboxylic acid components other than the above-mentioned ⁇ , ⁇ -linear aliphatic dicarboxylic acids having 4 to 20 carbon atoms include phthalic acid compounds such as isophthalic acid, terephthalic acid, and orthophthalic acid, and isomers of naphthalenedicarboxylic acid such as 1,2-naphthalenedicarboxylic acid, 1,3-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 1,5-naphthalenedicarboxylic acid, 1,6-naphthalenedicarboxylic acid, 1,7-naphthalenedicarboxylic acid, 1,8-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, and 2,7-naphthalenedicarboxylic acid, and can be used alone or in combination of two or more kinds.
  • phthalic acid compounds such as isophthalic acid,
  • the xylylenediamine-based polyamide resin contains diamine-derived structural units and dicarboxylic acid-derived structural units as the main components, but does not completely exclude other structural units.
  • the resin may contain lactams such as ⁇ -caprolactam and laurolactam, and structural units derived from aliphatic aminocarboxylic acids such as aminocaproic acid and aminoundecanoic acid.
  • the main component means that, among the structural units constituting the xylylenediamine-based polyamide resin, the total number of diamine-derived structural units and dicarboxylic acid-derived structural units is the largest among all structural units.
  • the total of the diamine-derived structural units and dicarboxylic acid-derived structural units in the xylylenediamine-based polyamide resin preferably accounts for 90% by mass or more of the total structural units, more preferably accounts for 95% by mass or more, even more preferably accounts for 97% by mass or more, and even more preferably accounts for 99% by mass or more.
  • the content of aromatic polyamide resin (preferably xylylenediamine-based polyamide resin) in the sealant layer contained in the first multilayer body and the second multilayer body is preferably 50% by mass or more, more preferably 60% by mass or more, and even more preferably 70% by mass or more, based on 100% by mass of the sealant layer. By making it equal to or more than the lower limit, the heat seal strength tends to be further improved.
  • the content of aromatic polyamide resin in the sealant layer contained in the first multilayer body and the second multilayer body of this embodiment is 100% by mass or less, based on 100% by mass of the sealant layer.
  • the sealant layer of the present embodiment may contain only one type of aromatic polyamide resin, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.
  • examples of aliphatic polyamide resins that can be contained in the sealant layer include polyamide 4, polyamide 46, polyamide 410, polyamide 6, polyamide 66, polyamide 666, polyamide 610, polyamide 11, polyamide 116, polyamide 12, polyamide 612, etc., more preferably polyamide 6, polyamide 66, polyamide 666, and even more preferably polyamide 6.
  • the sealant layer of the present embodiment may contain no aliphatic polyamide resin, may contain only one type, or may contain two or more types.
  • an aromatic polyamide resin produced using recycled resin or biomass raw material.
  • biomass thermoplastic resin By using a biomass thermoplastic resin, it is possible to reduce the environmental load.
  • bio-adipic acid can be used as a biomass raw material.
  • Mass balance certified (ISCC PLUS) adipic acid can also be used. Mass balance certification means that the amount of renewable raw materials or bio-raw materials used in each factory or production facility and the amount of products produced or shipped are quantified and guaranteed together with the quality.
  • the glass transition temperature of the polyamide resin contained in the sealant layer is preferably 50°C or higher, more preferably 60°C or higher, and is preferably 160°C or lower, more preferably 120°C or lower.
  • the glass transition temperature of the aromatic polyamide resin is the glass transition temperature of the resin with the largest content.
  • the melting point of the polyamide resin contained in the sealant layer is preferably 150°C or higher, more preferably 180°C or higher, even more preferably 200°C or higher, and even more preferably 205°C or higher.
  • the melting point of the polyamide resin contained in the sealant layer is preferably 350°C or lower, more preferably 330°C or lower, even more preferably 300°C or lower, even more preferably 280°C or lower, even more preferably 260°C or lower, and even more preferably 250°C or lower.
  • the melting point of the aromatic polyamide resin is the melting point of the resin with the largest content.
  • the glass transition temperature (Tg) and melting point (Tm) are values measured according to differential scanning calorimetry (DSC) in accordance with ISO 11357.
  • DSC differential scanning calorimetry
  • a resin is placed in the measurement pan of the differential scanning calorimeter, heated to a temperature exceeding the melting point at a heating rate of 10°C/min under a nitrogen atmosphere, and then quenched for pretreatment before measurement.
  • the measurement conditions are a heating rate of 10°C/min, held at 280°C for 5 minutes, and then a cooling rate of -5°C/min down to 100°C to determine the glass transition temperature (Tg) and melting point (Tm).
  • a "DSC-60" manufactured by Shimadzu Corporation is used.
  • the number average molecular weight (Mn) of the polyamide resin contained in the sealant layer is preferably 6,000 or more, more preferably 8,000 or more, and even more preferably 10,000 or more, and is preferably 100,000 or less, and more preferably 50,000 or less.
  • the number average molecular weight is the number average molecular weight of the mixture.
  • the number average molecular weight (Mn) of aromatic polyamide resin is measured using gel permeation chromatography (GPC) and calculated using standard polymethyl methacrylate (PMMA) equivalent values.
  • GPC gel permeation chromatography
  • PMMA polymethyl methacrylate
  • Two columns packed with styrene polymers are used as the packing material, and hexafluoroisopropanol (HFIP) with a sodium trifluoroacetate concentration of 2 mmol/L is used as the solvent.
  • the resin concentration is 0.02 mass%
  • the column temperature is 40°C
  • the flow rate is 0.3 mL/min
  • measurements are made using a refractive index detector (RI).
  • RI refractive index detector
  • the sealant layer used in this embodiment may or may not contain a thermoplastic resin other than polyamide resin, as long as it does not impair the purpose and effect of the present invention.
  • the total of the polyamide resins preferably accounts for 90% or more by mass of the sealant layer, more preferably 95% or more by mass, even more preferably 97% or more by mass, even more preferably 98% or more by mass, may account for 99% or more by mass, and is preferably 100% or less by mass.
  • the sealant layer used in this embodiment preferably does not substantially contain any thermoplastic resin other than polyamide resin.
  • the content of thermoplastic resin other than polyamide resin contained in the sealant layer in this embodiment is preferably less than 1 mass % in 100 mass % of the sealant layer, and more preferably less than 0.1 mass %.
  • the sealant layer used in this embodiment may contain resin additives such as antioxidants, stabilizers such as heat stabilizers, hydrolysis resistance improvers, weathering stabilizers, matting agents, UV absorbers, nucleating agents, plasticizers, dispersants, flame retardants, antistatic agents, coloring inhibitors, antigelling agents, colorants, and release agents.
  • resin additives such as antioxidants, stabilizers such as heat stabilizers, hydrolysis resistance improvers, weathering stabilizers, matting agents, UV absorbers, nucleating agents, plasticizers, dispersants, flame retardants, antistatic agents, coloring inhibitors, antigelling agents, colorants, and release agents.
  • the total content of the resin additives in the sealant layer used in this embodiment is preferably 0 to 5 mass %, and more preferably 0 to 3 mass %, of the sealant layer.
  • the total amount of the polyamide resins including the aromatic polyamide resin and the aliphatic polyamide resin is preferably 95% by mass or more, more preferably 97% by mass or more, and may be 99% by mass or more, and is preferably 100% by mass or less, of the resin components contained in the multilayer container.
  • the resin component means polyamide resin, other thermoplastic resins and resin additives, and usually means all components other than the filler and solvent contained in the multi-layer container.
  • the total amount of components other than the polyamide resin contained in the resin component is preferably 0 to 3 mass %, more preferably 0 to 1 mass %.
  • the sealant layers in the multi-layer container of this embodiment may be the same or different.
  • the sealant layer contained in the first multilayer body and the sealant layer contained in the second multilayer body preferably have a common composition of 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more. By adopting such a configuration, the fusion strength between the multilayer bodies can be increased.
  • the substrate layers included in the first multilayer body and the second multilayer body each independently contain an aliphatic polyamide resin.
  • the aliphatic polyamide resin is preferably a resin in which 80% by mass or more of all structural units excluding the terminal groups are derived from aliphatic monomers, and 85% by mass or more of all structural units excluding the terminal groups are derived from aliphatic monomers, more preferably a resin in which 90% by mass or more of all structural units excluding the terminal groups are derived from aliphatic monomers, even more preferably a resin in which 95% by mass or more of all structural units excluding the terminal groups are derived from aliphatic monomers, and even more preferably a resin in which 97% by mass or more of all structural units excluding the terminal groups are derived from aliphatic monomers.
  • the upper limit of the proportion of structural units derived from aliphatic monomers in the aliphatic polyamide resin is 100% by mass of all structural units excluding the terminal groups.
  • aliphatic polyamide resins examples include polyamide 4, polyamide 46, polyamide 410, polyamide 6, polyamide 66, polyamide 666, polyamide 610, polyamide 11, polyamide 116, polyamide 12, polyamide 612, etc., with polyamide 6, polyamide 66, and polyamide 666 being more preferred, and polyamide 6 being even more preferred.
  • aliphatic polyamide resin it is also preferable to use an aliphatic polyamide resin (biomass thermoplastic resin) produced using recycled resin or biomass raw materials.
  • biomass thermoplastic resin By using a biomass thermoplastic resin, it is possible to reduce the environmental burden.
  • the content ratio of the aliphatic polyamide resin in the base layer contained in the first multilayer body and the second multilayer body is preferably 93% by mass or more, more preferably 95% by mass or more, even more preferably 96% by mass or more, even more preferably 97% by mass or more, even more preferably 98% by mass or more, and even more preferably 99% by mass or more, based on 100% by mass of the base layer.
  • the content ratio of the aliphatic polyamide resin in the base layer contained in the first multilayer body and the second multilayer body of this embodiment is 100% by mass or less, based on 100% by mass of the base layer.
  • the base layer of the present embodiment may contain only one type of aliphatic polyamide resin, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.
  • the base layer used in the present embodiment may or may not contain a polyamide resin other than an aliphatic polyamide resin or a thermoplastic resin other than a polyamide resin, as long as the object and effect of the present invention are not impaired.
  • the base layer used in the present embodiment preferably does not substantially contain any thermoplastic resin other than the polyamide resin.
  • the content of the thermoplastic resin other than the polyamide resin contained in the base layer in the present embodiment is preferably less than 1 mass %, more preferably less than 0.1 mass %, in 100 mass % of the base layer.
  • the base layer used in this embodiment preferably does not substantially contain any polyamide resin other than the aliphatic polyamide resin.
  • the content of the polyamide resin other than the aliphatic polyamide resin contained in the base layer in this embodiment is preferably less than 10% by mass, more preferably less than 5% by mass, even more preferably less than 3% by mass, even more preferably less than 1% by mass, and even more preferably less than 0.1% by mass, based on 100% by mass of the base layer.
  • the base layer used in this embodiment may contain resin additives such as stabilizers such as antioxidants and heat stabilizers, hydrolysis resistance improvers, weathering stabilizers, matting agents, UV absorbers, nucleating agents, plasticizers, dispersants, flame retardants, antistatic agents, coloring inhibitors, gelling inhibitors, colorants, and release agents.
  • resin additives such as stabilizers such as antioxidants and heat stabilizers, hydrolysis resistance improvers, weathering stabilizers, matting agents, UV absorbers, nucleating agents, plasticizers, dispersants, flame retardants, antistatic agents, coloring inhibitors, gelling inhibitors, colorants, and release agents.
  • the total content of the resin additives in the substrate layer used in this embodiment is preferably 0 to 5 mass % of the substrate layer, and more preferably 0 to 3 mass %.
  • the substrate layers may be the same or different.
  • the base layer contained in the first multilayer body and the base layer contained in the second multilayer body preferably have at least 80% by mass of their composition in common, more preferably at least 90% by mass of their composition in common, and even more preferably at least 95% by mass of their composition in common.
  • the method for producing the multilayer container of the present embodiment is not particularly specified, and it can be produced by a known method. Usually, it is preferable to produce the first multilayer body and the second multilayer body by fusing a part of them so that the sealant layer of the first multilayer body and the sealant layer of the second multilayer body face each other.
  • the first multilayer body and the second multilayer body are the same as those described in the above-mentioned multilayer container section, and the preferred ranges are also the same.
  • the moisture content of the first multilayer body and the second multilayer body at the time of fusing is 10,000 mass ppm or less, respectively, just before sealing (fusing).
  • the moisture content is 10,000 mass ppm or less, respectively, just before sealing (fusing).
  • the moisture content is more preferably 9000 ppm by mass or less, even more preferably 7000 ppm by mass or less, even more preferably 5000 ppm by mass or less, and even more preferably 4500 ppm by mass or less, and may be 3500 ppm by mass or less, 3000 ppm by mass or less, or 2500 ppm by mass or less depending on the application.
  • the lower limit of the moisture content is 0 ppm by mass or more.
  • the manufactured first multilayer body and second multilayer body under conditions that make them less likely to absorb moisture until immediately before sealing.
  • the temperature during the fusion is preferably equal to or higher than the glass transition temperature (Tg) of the polyamide resin, more preferably equal to or higher than Tg+20°C, even more preferably equal to or higher than Tg+30°C, even more preferably equal to or higher than Tg+35°C, and even more preferably equal to or higher than Tg+45°C.
  • Tg glass transition temperature
  • the upper limit of the temperature during the fusion is preferably equal to or lower than Tg+140°C, more preferably equal to or lower than Tg+130°C, even more preferably equal to or lower than Tg+120°C, even more preferably equal to or lower than Tg+110°C, and even more preferably equal to or lower than Tg+100°C, based on the glass transition temperature (Tg) of the polyamide resin.
  • Tg glass transition temperature
  • the temperature during heat fusion is preferably 200° C. or lower, more preferably 180° C. or lower, even more preferably 160° C. or lower, and even more preferably 140° C. or lower depending on the application, etc.; it is preferably 80° C. or higher, more preferably 100° C. or higher, even more preferably 110° C. or higher, and even more preferably 130° C. or higher depending on the application, etc.
  • the temperature during heat fusion may be constant, or may be gradually increased and/or decreased. In this case, it is preferable that the highest heat fusion temperature is within the above range.
  • the fusion time is not particularly limited, but is, for example, 1 second or more and 1 minute or less.
  • the pressure during fusion is not particularly limited, but is, for example, 0.2 MPa or more and 0.5 MPa or less.
  • a method for producing recycled polyamide resin which includes crushing the multilayer container. That is, since the multilayer container of the present embodiment is mostly composed of polyamide resin, it is close to a single material and can be crushed to produce recycled polyamide resin. Furthermore, it is also preferable to form the base layer of the multilayer container of this embodiment using the recycled polyamide resin obtained by the method for producing a recycled polyamide resin of this embodiment.
  • PA-1 polyamide resin (MXD6) synthesized from metaxylylenediamine and adipic acid, manufactured by Mitsubishi Gas Chemical Company, Inc., S6007, melting point: 237°C, glass transition temperature: 85°C
  • PA-2 Polyamide resin (MXD6) synthesized from metaxylylenediamine, adipic acid, and isophthalic acid, manufactured by Mitsubishi Gas Chemical Company, Inc., S7007, melting point: 229°C, glass transition temperature: 92°C
  • PA6 Polyamide 6, manufactured by UBE, product number 1022B
  • PA666 Polyamide 666, manufactured by UBE, product number 5023B
  • PA6I/6T Polyamide 6I/6T, manufactured by EMS Co., Ltd., G21,
  • Examples 1 to 19 and Comparative Examples 1 to 5 ⁇ Production of multilayer body> Using a multilayer sheet manufacturing apparatus equipped with two extruders, a feed block, a T-die, a cooling roll, a winder, etc., PA6 was extruded from the first extruder at 240°C, and the sealant layer resin described in the Examples was extruded from the second extruder at 260°C, and a multilayer body having a two-type, two-layer structure of PA6/sealant layer was produced via the feed block. The resulting multilayer body was stored sealed in a moisture-proof film until each test was performed.
  • the moisture content was measured using a Karl Fischer moisture meter in accordance with the method of ISO 15512. The unit is ppm.
  • the Karl Fischer moisture meter used was a coulometric titration type trace moisture measuring device CA-200 manufactured by Nitto Seiko Analytech (formerly Mitsubishi Chemical Analytech).
  • the multilayer body obtained above was subjected to a film impact test as follows.
  • the obtained stretched film was cut into a 10 cm square, and the film impact value was measured using a film impact tester in accordance with ASTM D3420.
  • the film impact tester used was an FT-60 manufactured by Orientec Co., Ltd.
  • the unit was kgfcm.
  • the pinhole resistance was evaluated by the Gelboflex test as follows.
  • the obtained stretched film was cut into 25 cm squares and attached to a pinhole resistance tester.
  • the film was subjected to a 440° twisting motion and a 65 mm linear motion at a rate of 40 times/min, and the film was bent 1000 times.
  • the number of pinholes in the film after bending was measured using a pinhole inspection machine, and the number of pinholes per 100 cm2 of film was calculated.
  • the number of pinholes per 100 cm2 of film is calculated as follows.
  • Number of pinholes (pieces/100 cm 2 ) total number of pinholes (pieces)/effective test area (cm 2 ) ⁇ 100
  • a Gelbo Flex Tester manufactured by Rigaku Corporation was used as the pinhole resistance tester, and a POROSCOPE DC manufactured by Fischer was used as the pinhole inspection machine.
  • the Gelbo flex test was performed 20 times, 50 times, 200 times, and 400 times, and the number of pinholes formed was measured.
  • the multilayer container of this embodiment had high impact resistance and strong sealant strength. Furthermore, it also had excellent pinhole resistance. In addition, because it was made only from polyamide resin, recyclability was improved.
  • First multilayer body 12 Sealant layer included in first multilayer body 13 Base layer included in first multilayer body 2 Second multilayer body 22 Sealant layer included in second multilayer body 23 Base layer included in second multilayer body 10 Multilayer container

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  • Engineering & Computer Science (AREA)
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PCT/JP2024/019335 2023-07-31 2024-05-27 多層容器、リサイクルポリアミド樹脂の製造方法、および、多層容器の製造方法 Pending WO2025027993A1 (ja)

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS52875A (en) * 1975-06-24 1977-01-06 Toyobo Co Ltd Composite film for packaging
JP2011037199A (ja) 2009-08-17 2011-02-24 Mitsubishi Gas Chemical Co Inc 多層容器
JP2011057237A (ja) 2009-09-07 2011-03-24 Mitsubishi Gas Chemical Co Inc シール性及びフレーバー保持性に優れる容器及び多層成形体
JP2012041076A (ja) * 2010-08-20 2012-03-01 Kuraray Co Ltd ヒートシール用フィルム及び包装袋
JP4894982B1 (ja) 2011-04-12 2012-03-14 三菱瓦斯化学株式会社 ポリアミド樹脂系複合材およびその製造方法
WO2017141969A1 (ja) 2016-02-16 2017-08-24 三菱瓦斯化学株式会社 多層容器およびその応用
WO2021241471A1 (ja) 2020-05-29 2021-12-02 三菱瓦斯化学株式会社 ポリアミド樹脂、ポリアミド樹脂組成物および成形品
JP2023068909A (ja) 2021-11-04 2023-05-18 三菱瓦斯化学株式会社 多層容器、容器を製造する方法および再生ポリエステル樹脂の製造方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS52875A (en) * 1975-06-24 1977-01-06 Toyobo Co Ltd Composite film for packaging
JP2011037199A (ja) 2009-08-17 2011-02-24 Mitsubishi Gas Chemical Co Inc 多層容器
JP2011057237A (ja) 2009-09-07 2011-03-24 Mitsubishi Gas Chemical Co Inc シール性及びフレーバー保持性に優れる容器及び多層成形体
JP2012041076A (ja) * 2010-08-20 2012-03-01 Kuraray Co Ltd ヒートシール用フィルム及び包装袋
JP4894982B1 (ja) 2011-04-12 2012-03-14 三菱瓦斯化学株式会社 ポリアミド樹脂系複合材およびその製造方法
WO2017141969A1 (ja) 2016-02-16 2017-08-24 三菱瓦斯化学株式会社 多層容器およびその応用
WO2021241471A1 (ja) 2020-05-29 2021-12-02 三菱瓦斯化学株式会社 ポリアミド樹脂、ポリアミド樹脂組成物および成形品
JP2023068909A (ja) 2021-11-04 2023-05-18 三菱瓦斯化学株式会社 多層容器、容器を製造する方法および再生ポリエステル樹脂の製造方法

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