Classifications

• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
  • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
  • B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
  • B29B17/02—Separating plastics from other materials
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J11/00—Recovery or working-up of waste materials
  • C08J11/04—Recovery or working-up of waste materials of polymers
  • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
  • C08J11/16—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with inorganic material
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J11/00—Recovery or working-up of waste materials
  • C08J11/04—Recovery or working-up of waste materials of polymers
  • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
  • C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
  • C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
• • 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
  • Y02W30/62—Plastics recycling; Rubber recycling

Definitions

• the present invention relates to a separation solution for separating at least one component from a mixed or composite material composed of two or more components, the mixed or composite material including at least an ester bond-containing polymer component having an ester bond in its main chain structure, and a separation method using such a separation solution.
• Patent Document 1 proposes a method for recovering polypropylene resin by dissolving the polyurethane resin in a resin composite formed from polyurethane resin and polypropylene resin using a treatment liquid containing alcohols, ketones, or ethers.
• the technology in Patent Document 1 requires the treatment liquid to be heated to a high temperature of around 145°C, which poses the problems of requiring a great deal of energy to achieve such a high temperature and the need for large-scale equipment.
• Patent Document 2 proposes a method of peeling a composite material by immersing the composite material in a stripping solution containing a stripping agent and an aqueous solvent containing water in a ratio of greater than 51% by weight to 100% by weight.
• the method in Patent Document 2 uses an aqueous solvent containing water in a ratio of greater than 51% by weight to 100% by weight, the swelling power required for penetration into the interfaces of the materials that make up the composite material is insufficient, resulting in the problem that it takes a long time to peel or separate the materials that make up the composite material.
• the object of the present invention is to provide a separation solution that can effectively separate at least one component from a mixed or composite material composed of two or more components, the mixed or composite material including at least an ester bond-containing polymer component having an ester bond in its main chain structure, under relatively mild conditions and in a relatively short time.
• a separation chemical solution for separating at least one component from a mixed material or composite material composed of two or more components, the mixed material or composite material including at least an ester bond-containing polymer component having an ester bond in its main chain structure, the separation chemical solution containing an alcohol, a basic catalyst, and a co-solvent.
• Aspect 2 of the present invention provides the separation chemical solution of aspect 1, wherein the mixed material or composite material is a laminate having a layer containing the ester bond-containing polymer component.
• Aspect 3 of the present invention there is provided a separation chemical solution according to Aspect 2, wherein the laminate is a packaging container.
• a separation chemical solution according to any one of aspects 1 to 3, wherein the co-solvent is a dialkyl ketone, a halogenated alkane, or a cyclic ether.
• Aspect 5 of the present invention provides a separation chemical solution according to any one of aspects 1 to 4, wherein the auxiliary solvent is acetone.
• Aspect 7 of the present invention provides a separation chemical solution according to any one of aspects 1 to 6, wherein the base catalyst is at least one selected from potassium carbonate, sodium hydroxide, potassium hydroxide, sodium alkoxide, and potassium alkoxide.
• a ninth aspect of the present invention provides a separation method for separating at least one component from a mixed or composite material composed of two or more components, the mixed or composite material including at least an ester bond-containing polymer component having an ester bond in its main chain structure, the separation method comprising a step of contacting the mixed or composite material with a separation chemical solution containing an alcohol, a basic catalyst, and a co-solvent.
• aspect 10 of the present invention there is provided a separation method according to aspect 9, in which the mixed material or composite material is brought into contact with the separation chemical solution at a temperature of 0 to 65°C.
• the separation solution of the present invention makes it possible to effectively separate at least one component from a mixed or composite material composed of two or more components, which contains at least an ester bond-containing polymer component having an ester bond in its main chain structure, under relatively mild conditions and in a relatively short time.
• the separation chemical solution of the present invention contains an alcohol, a basic catalyst, and a co-solvent, and is used to separate at least one component from a mixed material or composite material composed of two or more components, the mixed material or composite material including at least an ester bond-containing polymer component having an ester bond in its main chain structure.
• the separation solution of the present invention makes it possible to effectively separate at least one component from a mixed or composite material composed of two or more components, including at least an ester bond-containing polymer component having an ester bond in its main chain structure (hereinafter referred to as "ester bond-containing polymer component" as appropriate), under relatively mild conditions (preferably temperature conditions of 0 to 65°C) and in a relatively short time.
• ester bond-containing polymer component preferably temperature conditions of 0 to 65°C
• the separation solution of the present invention acts on the ester bonds contained in the main chain structure of the ester bond-containing polymer component contained in the mixed material or composite material, thereby depolymerizing the ester bond-containing polymer component under relatively mild conditions and in a relatively short time. This in turn makes it possible to suitably separate at least one component from the mixed material or composite material.
• a separation solution containing an alcohol, a basic catalyst, and an auxiliary solvent can promote the depolymerization of the ester bond-containing polymer component contained in the mixed material or composite material under relatively mild conditions and in a relatively short time, thereby enabling decomposition, which led to the completion of the present invention.
• the mixed or composite material to be separated using the separation chemical solution of the present invention is a mixed or composite material composed of two or more components, and as a constituent, it is sufficient if it contains at least an ester bond-containing polymer component having an ester bond in the main chain structure. It may be a mixed material made up of a mixture of two or more components, or a composite material made up of a combination of two or more components.
• the mixed material which is a mixture of two or more components, is not particularly limited, and may be a mixed material in which two or more components are uniformly mixed, or a mixed material in which at least one component is mixed in a localized distribution form (for example, a polymer blend, alloy, or composite composed of two or more components).
• the mixed material is a mixture of at least an ester bond-containing polymer component and a component other than the ester bond-containing polymer component.
• the ester bond-containing polymer component contained in the mixed material can be depolymerized and decomposed, thereby separating the components other than the ester bond-containing polymer component from the mixed material.
• the composite material comprising two or more components is not particularly limited, and examples thereof include materials in which two or more components are composited in contact with each other, and may also include materials in which two or more components simply coexist.
• suitable materials include laminates in which two or more components are layered together, and fibers in which two or more fibers are blended.
• laminates having at least a layer LE containing an ester bond-containing polymer component and a layer LO not containing an ester bond-containing polymer component are suitable.
• the ester bond-containing polymer component constituting the layer LE containing the ester bond-containing polymer component can be depolymerized and decomposed, thereby separating the layer LO not containing the ester bond-containing polymer component from the laminate.
• the layer LE containing an ester bond-containing polymer component may contain two or more types of ester bond-containing polymer components, and may also contain a component other than the ester bond-containing polymer component (for example, a filler or a polymer other than the ester bond-containing polymer component) to the extent that the layer LO not containing the ester bond-containing polymer component can be separated from the laminate.
• the layer LO not containing an ester bond-containing polymer component may be any layer constituted of a component other than the ester bond-containing polymer component, and may contain two or more types of components other than the ester bond-containing polymer component.
• the laminate as a composite material may be, for example, a laminate of three or more layers configured by bonding layers L ⁇ sub>0 ⁇ /sub> that do not contain an ester bond-containing polymer component together via a layer L ⁇ sub> 1 ⁇ /sub> that contains an ester bond-containing polymer component as an adhesive layer.
• the laminate may have a three-layer structure of "Layer L ⁇ sub>0 ⁇ /sub> 1 ⁇ /sub> that does not contain an ester bond-containing polymer component / Layer L ⁇ sub>1 ⁇ /sub> that contains an ester bond-containing polymer component / Layer L ⁇ sub>0 ⁇ /sub> 2 ⁇ /sub> that does not contain an ester bond-containing polymer component.”
• contact with the separating chemical solution of the present invention can depolymerize and decompose Layer L ⁇ sub>0 ⁇ /sub> E that contains an ester bond-containing polymer component, thereby separating Layer L ⁇ sub>0 ⁇ /sub>1 ⁇ /sub> that does not contain an ester bond-containing polymer component and Layer L ⁇ sub> 0 ⁇ /sub>2 that does not contain an ester bond-containing polymer component from the laminate.
• Such laminates are not particularly limited, but examples thereof include packaging materials such as packaging containers containing a layer LE containing an ester bond-containing polymer component, optical device component materials such as optical films, and industrial component materials such as electronic devices, batteries, capacitors, and magnetic tapes.
• packaging containers include packaging containers for retort pouches for retort pouch foods, metal cans for beverages, refill pouches for liquid detergents, packaging containers for confectioneries, and packaging containers for pharmaceuticals.
• the laminate is a packaging container, the components constituting the packaging container can be suitably separated, allowing it to be recycled.
• the laminate When the laminate is a packaging container, it may also include a layer for providing product information or a design, such as an ink layer.
• the ester bond-containing polymer component that constitutes the mixed or composite material may be any polymer having an ester bond in its main chain structure, and is not particularly limited. Examples include, but are not limited to, polyesters, polyester polyols, and polyester polyol-based polyurethanes. Polyesters include, but are not limited to, aromatic polyesters, wholly aromatic polyesters, polycarbonates, and aliphatic polyesters, with aromatic polyesters being preferred. Aromatic polyesters contain diol units and dicarboxylic acid units.
• Diol compounds that form diol units include ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, diethylene glycol, 1,6-hexylene glycol, cyclohexanedimethanol, and ethylene oxide adducts of bisphenol A, with ethylene glycol being preferred.
• Dicarboxylic acid compounds that form dicarboxylic acid units include aromatic dicarboxylic acids and their derivatives, such as terephthalic acid, isophthalic acid, phthalic acid, naphthalenedicarboxylic acid, and furandicarboxylic acid, with terephthalic acid being preferred.
• polyesters include polyethylene terephthalate, polytrimethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, and polyethylene furanoate. Of these, polyethylene terephthalate, a copolymer of ethylene glycol and terephthalic acid, is preferred.
• the above polyesters are not limited to those derived from petroleum-derived raw materials; they may also be polyesters derived from plant-derived raw materials, or polyesters made by recycling these petroleum- or plant-derived polyesters. The above polyesters may be used alone or in combination.
• Polyethylene terephthalate may contain, among all monomer units, units of dicarboxylic acids other than ethylene glycol that are copolymerizable with ethylene glycol and terephthalic acid.
• dicarboxylic acids other than terephthalic acid include malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, sebacic acid, dodecanedioic acid, eicosanedioic acid, pimelic acid, azelaic acid, methylmalonic acid, ethylmalonic acid, adamantanedicarboxylic acid, norbornenedicarboxylic acid, cyclohexanedicarboxylic acid, decalindicarboxylic acid, isophthalic acid, phthalic acid, 1,4-naphthalenedicarboxylic acid, 1,5-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 1,8-naphthalenedicar
• Polyethylene terephthalate may contain, among all monomer units, units of diols other than ethylene glycol that are copolymerizable with ethylene glycol and terephthalic acid.
• diols other than ethylene glycol include 1,2-propanediol, 1,3-propanediol, butanediol, 2-methyl-1,3-propanediol, hexanediol, neopentyl glycol, cyclohexanedimethanol, cyclohexanediethanol, decahydronaphthalenedimethanol, decahydronaphthalenediethanol, norbornanedimethanol, norbornanediethanol, tricyclodecanedimethanol, tricyclodecanediethanol, tetracyclododecanedimethanol, tetracyclododecanediethanol, decalindimethanol, decalindiethanol, 5-methylol-5-ethyl
• components other than the ester bond-containing polymer component constituting the mixed material or composite material are not particularly limited, and examples thereof include polymer components that do not have ester bonds in their main chain structure, low-molecular-weight organic components, inorganic components, etc.
• polystyrene resins such as polyethylene and polypropylene
• polyamide resins such as nylon
• acrylic resins such as polymethyl methacrylate
• fluororesins such as ABS resin and polytetrafluoroethylene
• polyvinyl alcohol-based resins such as polyvinyl alcohol and ethylene-vinyl alcohol copolymers
• polystyrene, polycarbonate and polyvinyl chloride
• rubber materials such as acrylonitrile butadiene rubber, styrene butadiene rubber, butadiene rubber, isoprene rubber, acrylic rubber, ethylene propylene rubber, urethane rubber, fluororubber, and silicone rubber
• cellulose-based materials such as natural fibers such as cotton and hemp and rayon
• polyurethanes composed of components other than the ester bond-containing polymer component, such as polyether polyol-based
• the separation chemical solution of the present invention is used to separate the above-mentioned mixed or composite materials, and contains an alcohol, a basic catalyst, and a co-solvent.
• the alcohol may be any compound having an alcoholic hydroxyl group, and is not particularly limited.
• examples include monoalcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, and amyl alcohol; and dialcohols such as ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, and 2,3-butanediol.
• monoalcohols are preferred from the viewpoint of facilitating the depolymerization of the ester bond-containing polymer component, with methanol or ethanol being more preferred, and methanol being particularly preferred.
• the base catalyst may be any catalyst that promotes the decomposition reaction of the ester bond via alcohol, and is not particularly limited.
• Examples include carbonates such as potassium carbonate, calcium carbonate, sodium carbonate, barium carbonate, magnesium carbonate, lithium carbonate, ammonium carbonate, copper(II) carbonate, iron(II) carbonate, and silver(I) carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal alkoxides such as lithium methoxide, lithium ethoxide, lithium tert-butoxide, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium methoxide, potassium ethoxide, and potassium tert-butoxide; and alkaline earth metal alkoxides such as calcium dimethoxide, calcium diethoxide, calcium di-tert-butoxide, magnesium dime
• base catalysts may be used alone or in combination of two or more.
• carbonates, alkali metal hydroxides, and alkali metal alkoxides are preferred as base catalysts.
• carbonates potassium carbonate is more preferred.
• alkali metal hydroxides sodium hydroxide and potassium hydroxide are more preferred.
• alkali metal alkoxides sodium methoxide and potassium methoxide are more preferred.
• Alkali metal hydroxides are even more preferred, and among alkali metal hydroxides, sodium hydroxide and potassium hydroxide are more preferred.
• the auxiliary solvent is an organic solvent without an alcoholic hydroxyl group that enhances the impregnation of the separation solution of the present invention into the ester bond-containing polymer component, thereby facilitating the depolymerization of the ester bond-containing polymer component.
• the auxiliary solvent can be any good solvent for the ester bond-containing polymer component, without any particular limitations.
• suitable auxiliary solvents include dialkyl ketones such as acetone, methyl ethyl ketone, and diethyl ketone; nitriles such as acetonitrile; halogenated alkanes such as dichloromethane and chloroform; and cyclic ethers such as tetrahydrofuran.
• a single auxiliary solvent may be used, or two or more may be used in combination.
• dialkyl ketones, halogenated alkanes, and cyclic ethers are preferred, with acetone, dichloromethane, and tetrahydrofuran being more preferred. From the perspective of ease of distillation (ease of solvent removal from the solution after depolymerization is complete), acetone is even more preferred.
• the alcohol and co-solvent content in the separation solution of the present invention is preferably in the range of 10/90 to 90/10, more preferably 20/80 to 90/10, even more preferably 25/75 to 85/15, even more preferably 30/70 to 80/20, and particularly preferably 40/60 to 80/20.
• the total amount of alcohol and co-solvent in the separation solution of the present invention is preferably 80 to 99.9 wt.%, more preferably 85 to 99.7 wt.%, even more preferably 90 to 99.7 wt.%, and particularly preferably 95 to 99.7 wt.%, based on the total weight of the separation solution.
• the amount of base catalyst in the separation solution of the present invention is preferably 0.1 to 20% by weight, more preferably 0.3 to 15% by weight, even more preferably 0.3 to 10% by weight, and particularly preferably 0.3 to 5% by weight, based on the total weight of the separation solution.
• the separation chemical solution of the present invention is a combination of an alcohol, a co-solvent, and a base catalyst, Monoalcohols, dialkyl ketones, and alkali metal hydroxides, dialcohols, dialkyl ketones, and alkali metal hydroxides, monoalcohols, halogenated alkanes, and alkali metal hydroxides, dialcohols, halogenated alkanes, and alkali metal hydroxides, monoalcohols, cyclic ethers, and alkali metal hydroxides, dialcohols, cyclic ethers, and alkali metal hydroxides, monoalcohols, nitriles, and alkali metal hydroxides, dialcohols, nitriles, and alkali metal hydroxides, Monoalcohols, dialkyl ketones, and carbonates, dialcohols, dialkyl ketones, and carbonates, monoalcohols, halogenated alkanes, and carbonates, dialcohol
• the separation liquid of the present invention may contain other components in addition to the alcohol, basic catalyst, and auxiliary solvent.
• Such other components include water, adsorbents, compatibilizers, antifoaming agents, viscosity modifiers, etc.
• water if water is contained as another component, the impregnation ability of the separation liquid with the ester bond-containing polymer component tends to decrease. Therefore, it is preferable to keep the water content in the separation liquid to 10% by weight or less, more preferably 5% by weight or less, and even more preferably 1% by weight or less.
• the separation liquid it is particularly preferable for the separation liquid to contain essentially no water. In other words, it is preferable that water is not intentionally added, and the content of water as an unavoidable component is kept to 5,000 ppm by weight or less.
• the separation method of the present invention is a separation method for separating at least one component from a mixed material or composite material composed of two or more components, the mixed material or composite material including at least an ester bond-containing polymer component having an ester bond in its main chain structure,
• the method includes a step of contacting the mixed material or composite material with the above-described separation chemical solution of the present invention.
• the method for contacting the mixed material or composite material with the separation chemical is not particularly limited, but a method in which the mixed material or composite material is immersed in the separation chemical is preferred, and stirring or shaking may be performed as necessary.
• the temperature at which the mixed or composite material is brought into contact with the separation chemical is not particularly limited, but is preferably a temperature below the boiling point of the methanol and auxiliary solvent contained in the mixed solvent. Specifically, the temperature at which the mixed or composite material is brought into contact with the separation chemical is preferably 0 to 65°C, more preferably 20 to 60°C, and even more preferably 35 to 55°C, from the viewpoint of eliminating the need for heating and cooling and thus saving energy.
• the contact time when the mixed material or composite material is brought into contact with the separation solution should be such that separation of each component from the mixed material or composite material is complete. While not particularly limited, the contact time is preferably 0.5 to 24 hours, and more preferably 1 to 8 hours. As described above, the separation solution of the present invention makes it possible to effectively separate at least one component from a mixed material or composite material in a relatively short time, even under relatively mild conditions (relatively low temperature conditions).
• Isolation methods are not particularly limited, but include solid-liquid separation such as sieving, filter press, and centrifugal filtration, crystallization, purification by distillation, magnetic separation, and gravity separation.
• Example 1 Preparation of separation chemical solution
• a mixed solvent was prepared by mixing methanol as an alcohol and acetone as a co-solvent at a weight ratio of 30/70. Then, 0.13 mmol of potassium carbonate (K 2 CO 3 ) as a base catalyst was added to 2.5 mL of the resulting mixed solvent to prepare a separation solution (amount of base catalyst in the separation solution: 0.90 wt %). The resulting separation solution was substantially free of water (water content: 5000 ppm by weight or less).
• the separating solution prepared above was heated to 50°C, and two 1 cm square test laminates 1 were immersed in the separating solution maintained at 50°C.
• the temperature of the separating solution was maintained at 50°C using an aluminum block temperature controller (Tosoh, DF-8321H), and the laminate was shaken at 100 rpm to perform an immersion separation test.
• the test laminate 1 used was a laminate having a six-layer configuration of PET layer/ink layer/polyester polyol urethane layer (adhesive layer)/nylon layer/polyester polyol urethane layer (adhesive layer)/polypropylene layer.
• Figure 1(A) is a photograph of the test laminate 1 before the immersion separation test
• Figure 1(B) is a photograph of the polypropylene layer separated by the immersion separation test
• Figure 1(C) is a photograph of the nylon layer separated by the immersion separation test.
• Example 2 The immersion separation test was carried out in the same manner as in Example 1, except that the temperature of the separation solution was changed to 23° C. As a result of the immersion separation test, the polypropylene layer and the nylon layer separated after 24 hours, confirming that the polypropylene layer and the nylon layer could be suitably recycled.
• Example 3 Preparation of separation chemical solution
• a separation solution was prepared in the same manner as in Example 1, except that the mixing ratio of methanol as the alcohol and acetone as the co-solvent was 50/50 (methanol/acetone weight ratio) (amount of base catalyst in the separation solution: 0.90 wt %).
• the resulting separation solution was substantially free of water (water content: 5000 wt ppm or less).
• Example 4 Preparation of separation chemical solution
• a separation solution was prepared in the same manner as in Example 1, except that the mixing ratio of methanol as the alcohol and acetone as the co-solvent was 80/20 (methanol/acetone weight ratio) (amount of base catalyst in the separation solution: 0.90 wt %).
• the obtained separation solution was substantially free of water (water content: 5000 wt ppm or less).
• Example 5 Preparation of separation chemical solution
• the obtained separation solution was substantially free of water (water content: 5000 wt ppm or less).
• Example 6 Preparation of separation chemical solution
• the obtained separation solution was substantially free of water (water content: 5000 wt ppm or less).
• Example 19 An immersion separation test was carried out in the same manner as in Example 1, using a separation solution obtained in the same manner as in Example 1, except that a test metal laminate 1 of 0.5 cm square was used instead of the test laminate 1.
• the test metal laminate 1 used was a metal laminate (aluminum can for soft drinks) having a five-layer structure of, from the outer surface side, a finishing varnish layer/ink layer/PET resin layer/aluminum can body metal layer/PET resin layer.
• Example 20 An immersion separation test was carried out in the same manner as in Example 1, using a separation solution obtained in the same manner as in Example 1, except that a test metal laminate 2 measuring 0.5 cm square was used instead of the test laminate 1.
• a test metal laminate 2 As the test metal laminate 2, a metal laminate (steel can for soft drinks) having a five-layer structure of, from the outer surface side, a finishing varnish layer/an ink layer/a PET resin layer/a metal steel can body layer/a PET resin layer was used.
• Example 21 A separation solution was prepared in the same manner as in Example 19, except that potassium hydroxide was used instead of potassium carbonate as the base catalyst, and an immersion separation test was carried out using the test metal laminate 1 in the same manner as in Example 19.

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