WO2010134554A1 - Composition de résine pour articles moulés en mousse, articles moulés en mousse configurés à partir de la composition de résine, et obturateur de conteneur configuré à partir de ceux-ci - Google Patents

Composition de résine pour articles moulés en mousse, articles moulés en mousse configurés à partir de la composition de résine, et obturateur de conteneur configuré à partir de ceux-ci Download PDF

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Publication number
WO2010134554A1
WO2010134554A1 PCT/JP2010/058468 JP2010058468W WO2010134554A1 WO 2010134554 A1 WO2010134554 A1 WO 2010134554A1 JP 2010058468 W JP2010058468 W JP 2010058468W WO 2010134554 A1 WO2010134554 A1 WO 2010134554A1
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mass
resin composition
foam
block copolymer
thermoplastic elastomer
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PCT/JP2010/058468
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English (en)
Japanese (ja)
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啓光 佐々木
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株式会社クラレ
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Priority to JP2011514439A priority Critical patent/JPWO2010134554A1/ja
Publication of WO2010134554A1 publication Critical patent/WO2010134554A1/fr

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    • 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
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/0061—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof characterized by the use of several polymeric components
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
    • 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
    • C08J2353/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
    • C08J2353/02—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers of vinyl aromatic monomers and conjugated dienes
    • 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
    • C08J2423/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/14—Applications used for foams

Definitions

  • the inventors of the present invention contain a tackifying resin in a specific ratio with respect to the styrenic block copolymer or its hydrogenated product, and have a specific expansion ratio.
  • the present inventors have found that the above-mentioned problems can be solved by using a resin composition for foamed molded articles, and have completed the present invention based on these findings.
  • the present invention provides the following (1) to (6).
  • thermoplastic elastomer composition having excellent gas barrier properties (oxygen barrier properties)
  • foam molded article comprising the same
  • container stopper a thermoplastic elastomer composition having excellent gas barrier properties (oxygen barrier properties)
  • thermoplastic elastomer composition used in the resin composition for foamed molded products of the present invention is a block copolymer and its hydrogenated product (I) (hereinafter abbreviated as “(hydrogenated) block copolymer (I)”). And tackifying resin (II) as essential components.
  • (Hydrogenated) Block Copolymer (I) The (hydrogenated) block copolymer (I) used in the present invention is a block copolymer having an aromatic vinyl compound polymer block (A) and a conjugated diene polymer block (B), and a hydrogenated product thereof. .
  • the polymer block (A) is mainly composed of a structural unit (aromatic vinyl compound unit) derived from an aromatic vinyl compound.
  • aromatic vinyl compound unit is preferably 90% by mass or more, more preferably 95% by mass or more, and still more preferably 100% by mass based on the mass of the polymer block (A).
  • aromatic vinyl compound constituting the polymer block (A) include styrene, ⁇ -methylstyrene, ⁇ -methylstyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, and t-butylstyrene.
  • the polymer block (A) may contain only a structural unit derived from one kind of the above-described aromatic vinyl compound, or may contain a structural unit derived from two or more kinds. Among them, the polymer block (A) is preferably mainly composed of structural units derived from styrene.
  • polybutadiene block 70 to 20 mol%, particularly 65 to 40 mol% of the unit derived from the butadiene is a 2-butene-1,4-diyl group [—CH 2 —CH ⁇ CH—CH 2 — 1,4-bonded butadiene units], and 30 to 80 mol%, particularly 35 to 60 mol% is a vinylethylene group [—CH (CH ⁇ CH) —CH 2 —; 1,2-bonded butadiene units].
  • the content of 1,4-bonded butadiene units (1,4-bond amount) in the polybutadiene block is within the above-described range, the rubber elasticity of the resulting thermoplastic elastomer composition is improved.
  • the molar ratio of isoprene unit: butadiene unit is preferably 1: 9 to 9: 1, more preferably 2: 8 to 8: 2, from the viewpoint of rubber properties.
  • the ratio is more preferably 3: 7 to 7: 3.
  • the polymer block (B) may have a small amount of a structural unit derived from another copolymerizable monomer together with a structural unit derived from a conjugated diene as long as the object of the present invention is not impaired.
  • the proportion of the structural unit derived from the other copolymerizable monomer is preferably less than 30% by mass based on the mass of the polymer block (B), and more preferably less than 10% by mass. Preferably, it is less than 5% by mass.
  • copolymerizable monomers can be used alone or in combination of two or more.
  • a structural unit derived from a conjugated diene and a structural unit derived from another copolymerizable monomer such as an aromatic vinyl compound are copolymerized, their bonding form may be random, block, or tapered.
  • the block copolymer used in the present invention has a part of the unsaturated double bond (carbon-carbon double bond) in the polymer block (B) from the viewpoint of good heat resistance and weather resistance, or All are preferably hydrogenated.
  • the hydrogenation rate of the polymer block (B) is preferably 50 mol% or more, more preferably 60 mol% or more, and further preferably 70 to 100 mol%.
  • the hydrogenation rate of the unsaturated double bond in the polymer block (B) is determined based on the content of the unsaturated double bond in the polymer block (B) by the iodine value measurement, infrared spectroscopy before and after the hydrogenation. It can be obtained from the measured value by measuring with a photometer (IR), nuclear magnetic resonance (NMR) or the like.
  • (Hydrogenated) block copolymer (I) may have a carboxyl group, a hydroxyl group, an acid anhydride group, an amino group, an epoxy group in the molecular chain and / or at the molecular end, as long as the gist of the present invention is not impaired. It may have one or more functional groups such as
  • the production method of the (hydrogenated) block copolymer (I) is not limited at all, and for example, a known polymerization method such as an ionic polymerization method such as anionic polymerization or cationic polymerization, a single site polymerization method, or a radical polymerization method is performed. Can be manufactured by.
  • a known polymerization method such as an ionic polymerization method such as anionic polymerization or cationic polymerization, a single site polymerization method, or a radical polymerization method is performed.
  • an aromatic vinyl compound and a conjugated diene are sequentially polymerized in an inert organic solvent such as n-hexane or cyclohexane using an alkyllithium compound as a polymerization initiator to obtain a desired molecule.
  • the thermoplastic elastomer composition used in the present invention may further contain a rubber softener for the purpose of imparting flexibility.
  • rubber softeners (III) include paraffinic, naphthenic, and aromatic process oils; phthalic acid derivatives such as dioctyl phthalate and dibutyl phthalate; white oil; mineral oil; a liquid form of ethylene and ⁇ -olefin Co-oligomer; liquid paraffin; polybutene; low molecular weight polybutadiene; low molecular weight polyisoprene.
  • ⁇ -olefin examples include 1-butene, 1-pentene, 3-methyl-1-butene, 1-hexene, 3-methyl-1-pentene, 4-methyl-1-pentene, 1-heptene, 1 - ⁇ -olefins having 20 or less carbon atoms such as octene, 1-nonene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene, etc., one or two of these More than seeds can be used.
  • the polyolefin resins (IV) from the viewpoint of gas barrier properties, a propylene homopolymer or HDPE (high density polyethylene) is preferable, and HDPE (high density polyethylene) is more preferable.
  • the content ratio is preferably 5 to 150 parts by mass with respect to 100 parts by mass of the (hydrogenated) block copolymer (I), and 10 to 120 parts by mass. More preferred is 20 to 100 parts by mass.
  • the content of the polyolefin resin (IV) is less than 5 parts by mass, the mechanical strength of the obtained foamed molded product may be reduced.
  • the content exceeds 150 parts by mass, the hardness of the obtained foamed molded product is increased and rubber elasticity is increased. Therefore, the packing performance as a container stopper may be inferior.
  • thermoplastic elastomer composition used in the present invention can contain various additives as required.
  • additives include lubricants, antioxidants, heat stabilizers, light stabilizers such as HALS, weathering agents, metal deactivators, ultraviolet absorbers, light stabilizers, copper damage inhibitors, and the like.
  • thermoplastic resins such as coalescence and ABS resin.
  • the lubricant has an effect of improving the fluidity of the thermoplastic elastomer composition and suppressing the thermal deterioration of the polymer.
  • the lubricant used in the present invention is not particularly limited as long as it has an effect on improving the fluidity of the thermoplastic elastomer composition.
  • hydrocarbon lubricants such as paraffin wax, microwax and polyethylene wax;
  • ester lubricants such as butyl acid, stearic acid monoglyceride, pentaerythritol tetrastearate and stearyl stearate, and silicon oil.
  • each component is directly supplied to the kneader as it is, and before kneading, pre-mixing is performed using a mixer such as a Henschel mixer, a high speed mixer, a V blender, a ribbon blender, a tumbler blender, or a conical blender.
  • a mixer such as a Henschel mixer, a high speed mixer, a V blender, a ribbon blender, a tumbler blender, or a conical blender.
  • thermoplastic elastomer composition used in the present invention is particularly excellent in gas barrier properties (oxygen barrier properties).
  • OTR oxygen transmission coefficient
  • a film-shaped test piece having a thickness of 300 ⁇ m was prepared, and the oxygen transmission coefficient (OTR) when measured according to JIS K 7126-1 (differential pressure method) by the method described in the examples below, It is preferably less than 25000 cc ⁇ 20 ⁇ m / m 2 ⁇ day ⁇ atm, more preferably less than 23000 cc ⁇ 20 ⁇ m / m 2 ⁇ day ⁇ atm, and even more preferably less than 20000 cc ⁇ 20 ⁇ m / m 2 ⁇ day ⁇ atm.
  • the oxygen permeability coefficient measured under such conditions is within the above range, the obtained foamed molded product and the container stopper using the same are excellent in gas barrier properties (oxygen barrier properties).
  • the resin composition for foam molded articles of the present invention contains the thermoplastic elastomer composition. Moreover, it can be set as the resin composition which added the said various additives and the foaming agent as needed. Although it does not restrict
  • organic foaming agent examples include N-nitroso compounds such as N, N′-dinitrosopentamethylenetetramine and N, N′-dimethyl-N, N′-dinitrosotephthalamide; azobisisobutyro Azo compounds such as nitrile, azodicarbonamide, barium azodicarboxylate; fluorinated alkanes such as trichloromonofluoromethane, dichloromonofluoromethane; paratoluenesulfonyl hydrazide, diphenylsulfone-3,3′-disulfonylhydrazide, 4 Sulfonylhydrazine compounds such as 4,4'-oxybis (benzenesulfonylhydrazide) and allylbis (sulfonylhydrazide); sulfonylsemicarbyl such as p-toluylenesulfonyl semicarbazide
  • heat-expandable fine particles examples include heat-expandable fine particles in which a heat-expandable compound such as isobutane or pentane is encapsulated in a microcapsule made of a thermoplastic resin such as vinylidene chloride, acrylonitrile, acrylic acid ester or methacrylic acid ester. be able to.
  • thermally expandable fine particles include “Microsphere” (trade name, epoxy resin-encapsulated microcapsule) manufactured by Matsumoto Yushi Seiyaku Co., Ltd., “Philite” (trade name, inorganic type) manufactured by Nippon Philite Co., Ltd.
  • Microballoon “EXPANCEL” (trade name, organic microballoon) manufactured by AKZO NOBEL, and the like.
  • foaming agents an inorganic foaming agent, an azo compound, or a sulfonyl hydrazide compound is preferable from the viewpoint of safety to the human body. These may be used alone or in combination of two or more.
  • the blending ratio is preferably 0.1 to 3% by mass, more preferably 0.3 to 2.9% by mass, based on the total mass of the thermoplastic elastomer composition. More preferably, the content is 0.4 to 2.8% by mass.
  • the blending ratio of the foaming agent is less than 0.1% by mass, the foaming ratio of the obtained foamed molded product may be insufficient, resulting in poor rubber elasticity.
  • the blending ratio exceeds 3% by mass, the foamed cells are enlarged. Since a molded article having ideal closed-cell foam cannot be obtained, flavor retention and gas barrier properties may be inferior.
  • nucleating agent a nucleating agent can be used as needed.
  • examples of the nucleating agent include talc, silica, alumina, mica, titania, zinc oxide, zeolite, calcium carbonate, magnesium carbonate, barium sulfate, aluminum hydroxide and other oxides, composite oxides, metal carbonates, metals Sulfates and metal hydroxides can be used.
  • the cell diameter can be easily adjusted, and a foamed molded article having appropriate flexibility can be obtained.
  • the foam molded article of the present invention can be obtained by foam molding the above resin composition for foam molded article.
  • a chemical method for foaming by decomposition or reaction of the foaming agent a physical method such as supercritical foaming or water foaming, and the like may be employed, and these methods may be used in combination.
  • a physical method such as supercritical foaming or water foaming, and the like
  • foaming method a chemical method for foaming by decomposition or reaction of the foaming agent
  • a physical method such as supercritical foaming or water foaming, and the like
  • these methods may be used in combination.
  • limiting in particular about the method of manufacturing a foaming molding The method normally used for foam molding, such as injection foam molding and extrusion foam molding, is employable.
  • the kneading temperature is preferably not higher than the decomposition temperature of the foaming agent.
  • injection foam molding or extrusion foam molding is preferable from the viewpoint of productivity, and injection foam molding is particularly preferable from the viewpoint of gas barrier properties (oxygen barrier properties).
  • the expansion ratio exceeds 2.5 times, the expanded cells are united, the expanded cell size becomes large and non-uniform, and the resulting expanded molded article is inferior in gas barrier properties.
  • the method described in detail in the items of the following examples is adopted.
  • Oxygen transmission coefficient (OTR) With respect to the thermoplastic elastomer composition before foam molding, the oxygen transmission coefficient (cc ⁇ 20 ⁇ m / m 2 ⁇ day ⁇ atm) was measured by a differential pressure type gas chromatographic method in accordance with JIS K7126-1 (differential pressure method).
  • the pellets of the thermoplastic elastomer composition produced in the following examples and comparative examples were compression-molded under heating with a compression molding machine to produce a film-shaped test piece having a thickness of 300 ⁇ m, and measurement was performed using the test piece. It was.
  • Equipment Gas permeability measuring device “GTR-10” manufactured by Yanagimoto Seisakusho, oxygen pressure: 0.25 MPa, measurement temperature: 35 ° C., measurement humidity: 0% RH
  • Unplugging force is 20-30kgf
  • X Unplugging force is less than 20 kgf or more than 30 kgf.
  • Reference Example 1 (Production of hydrogenated block copolymer (I) -1) A pressure-resistant container substituted with dry nitrogen was charged with 1.71 kg of styrene and 55.8 kg of cyclohexane as a solvent. To this solution, 157 ml of sec-butyllithium (10% by mass, cyclohexane solution) was added as an initiator and polymerized at 60 ° C. for 1 hour.
  • hydrogenated block copolymer (I) -1).
  • the resulting hydrogenated block copolymer (I) -1 had a hydrogenation rate of 98.2%, and in the state before hydrogenation, the content of the polymer block (A) was 30% by mass.
  • the number average molecular weight of A) was 9,500, and the number average molecular weight of the block copolymer was 98,000.
  • Reference Example 2 (Production of hydrogenated block copolymer (I) -2)
  • 64.0 kg of cyclohexane as a solvent 192 ml of sec-butyllithium (10% by mass, cyclohexane solution) as an initiator were charged, tetrahydrofuran was not added, 1.97 kg of styrene as a monomer to be polymerized, and isoprene and butadiene.
  • a mixture [isoprene / butadiene 60/40 (weight ratio)] 9.17 kg and 1.97 kg of styrene were successively added and polymerized to carry out a polymerization reaction and a hydrogenation reaction in the same manner as in Reference Example 1, and polystyrene.
  • a poly (isoprene / butadiene) -polystyrene triblock copolymer was obtained (hereinafter referred to as hydrogenated block copolymer (I) -2).
  • the hydrogenated block copolymer (I) -2 obtained had a hydrogenation rate of 98.9%, and in the state before hydrogenation, the content of the polymer block (A) was 30% by mass.
  • the number average molecular weight of A) was 9,400, and the number average molecular weight of the block copolymer was 93,000.
  • -Tackifying resin (II) -1 Terpene-based hydrogenated resin, Clearon P-115 manufactured by Yasuhara Chemical Co., Ltd.
  • Rubber softener (III) hydrogenated paraffinic oil, Diana Process Oil PW-90 manufactured by Idemitsu Kosan Co., Ltd.
  • Foaming agent-1 Sodium hydrogen carbonate, SELBON SC-P manufactured by Eiwa Chemical Industry Co., Ltd.
  • the foamed molded products obtained in Examples 1 to 9 are all excellent in gas barrier properties (oxygen barrier properties) and the foamed molded products have a uniform cell size. You can see that From this, it is sufficiently expected that the foamed molded products obtained in Examples 1 to 9 are excellent in gas barrier properties.
  • the molded bodies obtained in Comparative Examples 1 and 2 are not foamed because they do not contain a foaming agent. Moreover, it is inferior to the plug-out property.
  • the foamed molded article obtained in Comparative Example 3 has a large oxygen permeability coefficient and poor gas barrier properties because the thermoplastic elastomer composition used does not contain the tackifier resin (II).
  • the foam molding resin composition of the present invention, the foam molded article comprising the foam molding, and the container stopper are excellent in gas barrier properties (oxygen barrier properties), and therefore are particularly suitable as stoppers for food containers or beverage containers, particularly for glass bottles such as wine bottles. It can be suitably used as a stopper.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Closures For Containers (AREA)

Abstract

La présente invention concerne : une composition de résine pour articles moulés en mousse contenant une composition d'élastomère thermoplastique ayant d'excellentes propriétés barrières contre les gaz (propriétés barrières contre l'oxygène) ; des articles moulés en mousse configurés à partir de la composition de résine ; et un obturateur de conteneur configuré à partir de ceux-ci. La composition de résine pour articles moulés en mousse présente un rapport d'expansion de 1,1 à 2,5, contient une composition élastomère thermoplastique comprenant (I) 100 parties en poids d'un copolymère séquencé comprenant (A) un polymère séquencé vinyle aromatique et (B) un polymère séquencé diène conjugué ou un produit d'hydrogénation du copolymère séquencé et (II) 10 à 150 parties en poids d'une résine donnant du collant et présentant une constante de perméabilité à l'oxygène inférieure à 25 000 cc∙20 μm/m2∙jour∙atm tel que déterminé en utilisant un spécimen de la forme d'un film d'une épaisseur de 300 μm, et selon la norme JIS K 7126-1 (procédé de pression différentielle) ; l'invention concerne également des articles moulés en mousse configurés à partir de la composition de résine ; et un obturateur de conteneur configuré à partir de ceux-ci.
PCT/JP2010/058468 2009-05-20 2010-05-19 Composition de résine pour articles moulés en mousse, articles moulés en mousse configurés à partir de la composition de résine, et obturateur de conteneur configuré à partir de ceux-ci WO2010134554A1 (fr)

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KR20150036493A (ko) * 2012-07-12 2015-04-07 쓰리엠 이노베이티브 프로퍼티즈 캄파니 발포가능한 물품
JP2015529483A (ja) * 2012-07-12 2015-10-08 スリーエム イノベイティブ プロパティズ カンパニー 耳栓の作製方法
JP2020128523A (ja) * 2018-12-06 2020-08-27 ティエスアールシー・コーポレイションＴＳＲＣ Ｃｏｒｐｏｒａｔｉｏｎ ポリマー組成物、発泡体およびその方法

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JP2007169608A (ja) * 2005-11-22 2007-07-05 Mitsubishi Pencil Co Ltd 液体収容容器用の樹脂組成物およびそれよりなる液体収容容器

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JPH05295172A (ja) * 1992-04-17 1993-11-09 Japan Synthetic Rubber Co Ltd ゴム組成物
JP2004107519A (ja) * 2002-09-19 2004-04-08 Kuraray Co Ltd 発泡体およびその用途
JP2004149553A (ja) * 2002-10-28 2004-05-27 Kuraray Co Ltd 熱可塑性発泡体用組成物および発泡体
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JP2005320358A (ja) * 2004-05-06 2005-11-17 Asahi Kasei Life & Living Corp 合成樹脂発泡体
JP2007169608A (ja) * 2005-11-22 2007-07-05 Mitsubishi Pencil Co Ltd 液体収容容器用の樹脂組成物およびそれよりなる液体収容容器

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150036493A (ko) * 2012-07-12 2015-04-07 쓰리엠 이노베이티브 프로퍼티즈 캄파니 발포가능한 물품
JP2015529484A (ja) * 2012-07-12 2015-10-08 スリーエム イノベイティブ プロパティズ カンパニー 発泡性物品
JP2015529483A (ja) * 2012-07-12 2015-10-08 スリーエム イノベイティブ プロパティズ カンパニー 耳栓の作製方法
US10065344B2 (en) 2012-07-12 2018-09-04 3M Innovative Properties Company Method of making a personal protective article
KR102070642B1 (ko) * 2012-07-12 2020-01-29 쓰리엠 이노베이티브 프로퍼티즈 캄파니 발포가능한 물품
US11123902B2 (en) 2012-07-12 2021-09-21 3M Innovative Properties Company Method of making a personal protective article
JP2020128523A (ja) * 2018-12-06 2020-08-27 ティエスアールシー・コーポレイションＴＳＲＣ Ｃｏｒｐｏｒａｔｉｏｎ ポリマー組成物、発泡体およびその方法
TWI750548B (zh) * 2018-12-06 2021-12-21 台橡股份有限公司 高分子組成及其發泡體與方法
JP7042248B2 (ja) 2018-12-06 2022-03-25 ティエスアールシー・コーポレイション ポリマー組成物、発泡体およびその方法
US11746226B2 (en) 2018-12-06 2023-09-05 Tsrc Corporation Polymer composition, foam and method thereof

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