WO2017135189A1 - Composition de résine de polyamide comprenant un sel métallique de composé d'acide phénylphosphonique - Google Patents

Composition de résine de polyamide comprenant un sel métallique de composé d'acide phénylphosphonique Download PDF

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Publication number
WO2017135189A1
WO2017135189A1 PCT/JP2017/003170 JP2017003170W WO2017135189A1 WO 2017135189 A1 WO2017135189 A1 WO 2017135189A1 JP 2017003170 W JP2017003170 W JP 2017003170W WO 2017135189 A1 WO2017135189 A1 WO 2017135189A1
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WIPO (PCT)
Prior art keywords
polyamide
salt
polyamide resin
resin composition
acid compound
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Ceased
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PCT/JP2017/003170
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English (en)
Japanese (ja)
Inventor
一利 小高
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Nissan Chemical Corp
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Nissan Chemical Corp
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Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Priority to JP2017565533A priority Critical patent/JP6908892B2/ja
Publication of WO2017135189A1 publication Critical patent/WO2017135189A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers

Definitions

  • the present invention relates to a polyamide resin composition. More specifically, the present invention relates to a polyamide resin composition containing a crystal nucleating agent comprising a metal salt of a phenylphosphonic acid compound, and a polyamide resin molded product obtained from the resin composition.
  • Polyamide resins are generally used widely as engineering plastics with excellent mechanical properties, chemical resistance, oil resistance, and the like.
  • polyamide 610 classified as biomass plastics is excellent in properties such as chemical resistance, metal chloride resistance (for example, calcium chloride resistance), low water absorption, and dimensional stability.
  • metal chloride resistance for example, calcium chloride resistance
  • low water absorption for example, food containers, bearings, connectors, It is expected to be used as a molding material for automobile fuel tubes and hoses, interior materials, and casings and parts for electrical and electronic products.
  • the polyamide resin has a low crystallization speed, it has a drawback that it is softened at a temperature higher than the glass transition point (Tg) if it is not sufficiently crystallized. Also, heat treatment (annealing) at a predetermined temperature in the mold during injection molding improves the crystallization degree of the polyamide resin, but the crystallization speed is slow, so the molding cycleability is poor and productivity is a problem. There is.
  • the crystal nucleating agent becomes the primary crystal nucleus of the crystalline polymer, promotes crystal growth, and functions to refine the spherulite size and promote crystallization.
  • layered silicates Patent Document 1
  • talc Patent Document 2
  • the present invention provides a polyamide resin composition to which a crystallization nucleating agent suitable for promoting crystallization of a polyamide resin is added, a crystallization speed is higher than that of a polyamide resin, and a higher moldability can be improved. It aims at providing the polyamide resin molding obtained by crystallizing a polyamide resin composition.
  • the present inventors have promoted crystallization of polyamide resin by adding a metal salt of a specific phenylphosphonic acid compound as a crystal nucleating agent to the polyamide resin. Found that is possible.
  • this invention relates to the polyamide resin composition containing the crystal nucleus agent which consists of a polyamide resin and the metal salt of the phenylphosphonic acid compound represented by Formula [1] as a 1st viewpoint.
  • R 1 and R 2 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxycarbonyl group having 2 to 11 carbon atoms.
  • the metal salt of the phenylphosphonic acid compound is lithium salt, sodium salt, potassium salt, magnesium salt, calcium salt, barium salt, manganese salt, iron salt, cobalt salt, nickel salt, copper salt, zinc salt.
  • the present invention relates to a polyamide resin composition according to the first aspect, which is at least one metal salt selected from the group consisting of silver salts, aluminum salts, and tin salts.
  • the polyamide resin composition according to the second aspect wherein the metal salt of the phenylphosphonic acid compound is at least one metal salt selected from the group consisting of calcium salts, manganese salts, zinc salts and tin salts.
  • the present invention relates to the polyamide resin composition according to the third aspect, wherein the metal salt of the phenylphosphonic acid compound is a manganese salt.
  • the polyamide according to any one of the first to fourth aspects wherein the content of the crystal nucleating agent is 0.001 to 10 parts by mass with respect to 100 parts by mass of the polyamide resin.
  • the present invention relates to a resin composition.
  • the polyamide resin is polyamide 6, polyamide 11, polyamide 12, polyamide 46, polyamide 66, polyamide 610, polyamide 612, polyamide 1010, polyamide 1212, polyamide 4T, polyamide M5T, polyamide 6T, polyamide 6I, polyamide It is related with the polyamide resin composition as described in any one of the 1st viewpoint thru
  • the present invention relates to the polyamide resin composition according to the sixth aspect, in which the polyamide resin contains at least polyamide 610.
  • the use of a metal salt of a specific phenylphosphonic acid compound as a crystal nucleating agent improves the crystallization accelerating effect of the polyamide resin.
  • a resin composition and a polyamide resin molded body obtained by crystallizing the polyamide resin composition can be provided.
  • the polyamide (hereinafter also referred to as PA) resin composition of the present invention comprises a PA resin and a crystal nucleating agent comprising a metal salt of a phenylphosphonic acid compound.
  • PA resin examples of the PA resin used in the present invention include those made of a polymer of diamine and dibasic acid, a polymer of lactam or aminocarboxylic acid, or a copolymer of two or more of these. It is done.
  • diamine examples include aliphatic diamines such as tetramethylene diamine, hexamethylene diamine, octamethylene diamine, nonamethyle diamine, undecamethylene diamine, and dodecamethylene diamine; and aromatic / cyclic structures such as metaxylylene diamine. Examples include diamines.
  • dicarboxylic acid examples include aliphatic dicarboxylic acids such as adipic acid, heptanedicarboxylic acid, octanedicarboxylic acid, nonanedicarboxylic acid, undecanedicarboxylic acid, and dodecanedicarboxylic acid; and aromatic / cyclic structures such as terephthalic acid and isophthalic acid.
  • aliphatic dicarboxylic acids such as adipic acid, heptanedicarboxylic acid, octanedicarboxylic acid, nonanedicarboxylic acid, undecanedicarboxylic acid, and dodecanedicarboxylic acid
  • aromatic / cyclic structures such as terephthalic acid and isophthalic acid.
  • lactam examples include lactams having 6 to 12 carbon atoms such as ⁇ -butyrolactam, ⁇ -caprolactam, ⁇ -heptalactam, and ⁇ -laurolactam.
  • aminocarboxylic acid examples include aminocarboxylic acids having 6 to 12 carbon atoms such as ⁇ -aminocaproic acid, 7-aminoheptanoic acid, 11-aminoundecanoic acid, and 12-aminododecanoic acid.
  • PA resins include polyamide 6, polyamide 11, polyamide 12, polyamide 46, polyamide 66, polyamide 610, polyamide 612, polyamide 1010, polyamide 1212, polyamide 4T, polyamide M5T, polyamide 6T, polyamide 6I, Homopolymers such as polyamide 9T, polyamide 10T, and polyamide MXD6; and copolymers such as polyamide 6/66, polyamide 6/12, and polyamide 11/12.
  • polyamide 610 is preferable.
  • These PA resins may be used alone or in combination of two or more.
  • PA resins those commercially available can be suitably used.
  • the PA resin used in the present invention may be a blend polymer with other resins mainly composed of PA homopolymer or PA copolymer.
  • other resins include general-purpose thermoplastic resins / thermoplastic engineering plastics and biodegradable resins described later.
  • the content of the other resin in the blend polymer with the other resin is preferably 50% by mass or less.
  • thermoplastic resin / thermoplastic engineering plastic examples include polyethylene (PE), polyethylene copolymer, polypropylene (PP), polypropylene copolymer, ethylene-propylene copolymer, polybutylene (PB), and ethylene-vinyl alcohol copolymer.
  • PE polyethylene
  • PP polypropylene
  • PB polybutylene
  • ethylene-vinyl alcohol copolymer examples include polyethylene (PE), polyethylene copolymer, polypropylene (PP), polypropylene copolymer, ethylene-propylene copolymer, polybutylene (PB), and ethylene-vinyl alcohol copolymer.
  • Polyolefin resins such as polymer (EVOH), ethylene-vinyl acetate copolymer (EVA), ethylene-ethyl acrylate copolymer (EEA), poly (4-methyl-1-pentene); polystyrene (PS), high impact Polystyrene resins such as water-soluble polystyrene (HIPS), acrylonitrile-styrene copolymer (AS), acrylonitrile-butadiene-styrene copolymer (ABS), methyl methacrylate-styrene copolymer (MS); polymethyl methacrylate (Meth) acrylic resin such as PMMA); polyvinyl chloride resin; polyvinylidene chloride resin; polyurethane resin; polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polyethylene naphthalate (PEN), polybutylene naphthalate (PBN) Polyester resin; Polycarbonate resin; Polypheny
  • biodegradable resin examples include polyglycolic acid (PGA), polylactic acid (PLA), poly (3-hydroxybutyric acid) (PHB), and a copolymer of 3-hydroxybutyric acid and 3-hydroxyhexanoic acid (Polhydroxyalkanoic acids such as PHBH); polyester resins such as polycaprolactone, polybutylene succinate, polybutylene succinate / adipate, polybutylene succinate / carbonate, polyethylene succinate, polyethylene succinate / adipate; Polyvinyl alcohol; modified starch; cellulose acetate; chitin; chitosan; lignin and the like.
  • PGA polyglycolic acid
  • PLA polylactic acid
  • PHB poly (3-hydroxybutyric acid)
  • a copolymer of 3-hydroxybutyric acid and 3-hydroxyhexanoic acid Polyhydroxyalkanoic acids such as PHBH
  • polyester resins such as polycaprolactone, polybutylene succinate, polybuty
  • the crystal nucleating agent used in the present invention comprises a metal salt of a phenylphosphonic acid compound represented by the formula [1].
  • R 1 and R 2 in the formula are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or 2 to 11 carbon atoms.
  • the alkoxycarbonyl group having 2 to 11 carbon atoms refers to an alkoxycarbonyl group having 1 to 10 carbon atoms in the alkoxy group.
  • Examples of the alkyl group having 1 to 10 carbon atoms in R 1 and R 2 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a tert-butyl group.
  • Examples of the alkoxycarbonyl group having 2 to 11 carbon atoms include a methoxycarbonyl group and an ethoxycarbonyl group.
  • phenylphosphonic acid compound represented by the above formula [1] examples include phenylphosphonic acid, 4-methylphenylphosphonic acid, 4-ethylphenylphosphonic acid, 4-n-propylphenylphosphonic acid, 4-isopropylphenyl. Phosphonic acid, 4-n-butylphenylphosphonic acid, 4-isobutylphenylphosphonic acid, 4-tert-butylphenylphosphonic acid, 3,5-dimethoxycarbonylphenylphosphonic acid, 3,5-diethoxycarbonylphenylphosphonic acid, 2 , 5-dimethoxycarbonylphenylphosphonic acid, 2,5-diethoxycarbonylphenylphosphonic acid and the like. As these compounds, commercially available products can be preferably used as they are.
  • metal that forms the metal salt of the phenylphosphonic acid compound monovalent, divalent, and trivalent metals can be used. Two or more metals can be mixed and used. Specific examples of the metal forming the metal salt include lithium, sodium, potassium, magnesium, calcium, barium, manganese, iron, cobalt, nickel, copper, zinc, silver, aluminum, tin and the like. Among metal salts formed from these metals, calcium salts, manganese salts, zinc salts, and tin salts are preferable. Among these, a manganese salt is most preferable because it can increase the crystallization speed of the PA resin and obtain a PA resin composition excellent in molding processability.
  • the method for producing the metal salt of the phenylphosphonic acid compound is not particularly limited, but in general, the phenylphosphonic acid compound, the metal chloride, sulfate or nitrate, and an alkali such as sodium hydroxide are mixed in water. Thus, the metal salt of the phenylphosphonic acid compound is precipitated, filtered, and dried to obtain a crystalline powder. In addition, the phenylphosphonic acid compound and the metal oxide, hydroxide, carbonate, or organic acid salt are mixed and reacted in water or an organic solvent, and then the solvent is filtered or distilled and dried. Can also be obtained.
  • the form of the obtained powder is usually a granular crystal, a plate-like crystal, a rod-like crystal, a needle-like crystal, etc., and these crystals may be laminated.
  • these compounds (crystalline powder) are commercially available, commercially available products can be used.
  • the stoichiometric ratio of the phenylphosphonic acid compound to the metal is not particularly limited. Generally, the phenylphosphonic acid compound / metal stoichiometric ratio is 1/2 to 2 / It is preferable to use in the range of 1.
  • the metal salt of the phenylphosphonic acid compound preferably contains no free phenylphosphonic acid compound or metal that does not form a salt.
  • the average particle size of the metal salt of the phenylphosphonic acid compound is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less.
  • the average particle diameter ( ⁇ m) is a 50% volume diameter (median diameter) obtained by measurement by a laser diffraction / scattering method based on the Mie theory.
  • the crystalline powder obtained by the above method may be sheared by a homomixer, a Henschel mixer, a Ladige mixer or the like, if necessary.
  • a dry pulverizer such as a mixer having a particle diameter, a ball mill, a pin disc mill, a pulverizer, an inomizer, or a counter jet mill.
  • a wet pulverizer such as a ball mill, a bead mill, a sand grinder, or an attritor using water, an organic solvent that can be mixed with water, and a mixed solution thereof.
  • the addition amount of the metal salt of the phenylphosphonic acid compound is 0.001 to 10 parts by mass, preferably 0.01 to 5 parts by mass, more preferably 0.1 to 2 parts by mass with respect to 100 parts by mass of the PA resin. It is. By making the addition amount 0.001 part by mass or more, a sufficient crystallization rate can be obtained. Moreover, even if it exceeds 10 parts by mass, the crystallization rate does not increase further, so that it is economically advantageous to use it at 10 parts by mass or less.
  • the PA resin composition of the present invention can be blended with a known inorganic filler as long as the effects of the present invention are not impaired.
  • the inorganic filler include glass fiber, carbon fiber, talc, mica, silica, kaolin, clay, wollastonite, glass beads, glass flake, potassium titanate, calcium carbonate, magnesium sulfate, titanium oxide and the like.
  • the shape of these inorganic fillers may be any of fiber, granule, plate, needle, sphere, and powder. These inorganic fillers can be used within 300 parts by mass with respect to 100 parts by mass of the PA resin.
  • the PA resin composition of the present invention can be blended with a known flame retardant as long as the effects of the present invention are not impaired.
  • the flame retardant include halogen flame retardants such as bromine and chlorine; antimony flame retardants such as antimony trioxide and antimony pentoxide; inorganic flame retardants such as aluminum hydroxide, magnesium hydroxide and silicone compounds.
  • Phosphorus flame retardants such as red phosphorus, phosphate esters, ammonium polyphosphate, phosphazene, etc .; melamine, melam, melem, melon, melamine cyanurate, melamine phosphate, melamine pyrophosphate, melamine polyphosphate, melamine / melam polyphosphate
  • Melamine flame retardants such as melem double salt, melamine alkylphosphonate, melamine phenylphosphonate, melamine sulfate and melam methanesulfonate; fluororesins such as PTFE. These flame retardants can be used within 200 parts by mass with respect to 100 parts by mass of the PA resin.
  • additives that are generally added as necessary, for example, end-capping agents, hydrolysis inhibitors, thermal stabilizers, unless the effects of the present invention are impaired.
  • Light stabilizers, heat ray absorbers, UV absorbers, antioxidants, impact modifiers, plasticizers, compatibilizers, silane-based, titanium-based, aluminum-based coupling agents, foaming agents, antistatic agents, release agents Molding agents, lubricants, antibacterial and antifungal agents, pigments, dyes, fragrances, other various fillers, other crystal nucleating agents, other thermoplastic resins, and the like may be appropriately blended.
  • the PA resin composition of the present invention can be produced by mixing the PA resin and a crystal nucleating agent comprising a metal salt of the phenylphosphonic acid compound.
  • the method for mixing the crystal nucleating agent is not particularly limited, for example, a method of mixing the crystal nucleating agent with a composition containing PA resin or PA resin and other additives before molding, PA resin or PA resin at the time of molding. And a method of mixing a crystal nucleating agent with a composition containing the other additives (for example, side feed).
  • the PA resin composition of the present invention preferably has a cooling crystallization temperature (temperature at which the resin crystallizes in the process of cooling the molten resin composition) Tcc of 188 ° C. or higher, and 191 ° C. or higher. Some are more preferred.
  • the PA resin molded article of the present invention comprises a crystal nucleating agent comprising the crystallized PA resin and a metal salt of the phenylphosphonic acid compound.
  • a spherulite diameter of the PA resin molding of this invention 30 micrometers or less are preferable and 20 micrometers or less are more preferable.
  • a PA resin molded body having a smoother surface can be obtained.
  • Such a PA resin molded body can be obtained, for example, by using the PA resin composition of the present invention and crystallizing the PA resin contained therein.
  • the method for crystallizing the PA resin is not particularly limited.
  • the PA resin composition in the process of forming the PA resin composition into a predetermined shape, may be heated to the crystallization temperature or higher and then cooled. Further, in the above process, the PA resin composition is heated to a temperature equal to or higher than the crystallization temperature, and then rapidly cooled to form an amorphous body, which can be crystallized by heating.
  • the PA resin molded product of the present invention has excellent mechanical strength and heat resistance.
  • various molded products can be easily produced by using a conventional molding method such as general injection molding, blow molding, vacuum molding, compression molding or the like.
  • DSC Differential scanning calorimetry
  • PA610 Polyamide 610 [Daicel Evonik Co., Ltd. Bestamid (registered trademark) Terra HS16 Natural]
  • PPA Phenylphosphonic acid [manufactured by Nissan Chemical Industries, Ltd.]
  • PPA-Zn zinc phenylphosphonate [Eco Promote (registered trademark) manufactured by Nissan Chemical Industries, Ltd.]
  • HFIPA 1,1,1,3,3,3-hexafluoro-2-propanol
  • Example 1 To 100 parts by mass of PA610, 0.5 parts by mass of the compound shown in Table 1 and 900 parts by mass of HFIPA are added as crystal nucleating agents, and 30 minutes at room temperature (approximately 23 ° C.) using an ultrasonic cleaner (output 150 W). A polyamide resin composition was obtained by ultrasonic irradiation. This resin composition was dropped on a hot plate at 60 ° C. to evaporate the solvent, whereby an amorphous (amorphous) state polyamide resin film-shaped molded article containing a crystal nucleating agent was obtained. About the obtained amorphous film-like molded object, the temperature-falling crystallization temperature (Tcc) and the half crystallization time (t1 / 2 ) were measured in accordance with the following procedures. The results are also shown in Table 1.
  • Tcc Cold crystallization temperature

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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)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

[Problème] Fournir une composition de résine de polyamide à laquelle est ajouté un agent de nucléation de cristaux permettant de favoriser la cristallisation d'une résine de polyamide, ladite composition permettant d'élever le taux de cristallisation et d'améliorer encore les propriétés de processus de moulage supérieures par rapport aux résines de polyamide. [Solution] Une composition de résine de polyamide contenant une résine de polyamide et un agent de nucléation de cristaux qui comprend un sel métallique d'un composé acide phénylphosphonique représenté par la formule [1]. Dans la formule, R1 et R2 représentent chacun indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C10 ou un groupe alcoxycarbonyle C2-11.)
PCT/JP2017/003170 2016-02-01 2017-01-30 Composition de résine de polyamide comprenant un sel métallique de composé d'acide phénylphosphonique Ceased WO2017135189A1 (fr)

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JP2017565533A JP6908892B2 (ja) 2016-02-01 2017-01-30 フェニルホスホン酸化合物の金属塩を含むポリアミド樹脂組成物

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018009115A (ja) * 2016-07-14 2018-01-18 日産化学工業株式会社 ホスホン酸金属塩を含む芳香族ポリエーテルケトン樹脂組成物
CN109666294A (zh) * 2018-12-27 2019-04-23 会通新材料(上海)有限公司 一种结晶速率提升的聚酰胺56组合物及其应用

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114085519B (zh) * 2021-11-26 2023-12-19 上海金发科技发展有限公司 一种聚酰胺组合物及其制备方法和应用

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JPS6390560A (ja) * 1986-10-03 1988-04-21 Asahi Chem Ind Co Ltd ポリアミド樹脂組成物
WO2010131678A1 (fr) * 2009-05-12 2010-11-18 日産化学工業株式会社 Procédé pour la production de fines particules de sel métallique de l'acide phosphonique
WO2011030822A1 (fr) * 2009-09-09 2011-03-17 日産化学工業株式会社 Procédé de production de sel métallique d'acide phosphonique et composition de résine thermoplastique contenant du sel métallique d'acide phosphonique
WO2013047766A1 (fr) * 2011-09-30 2013-04-04 日産化学工業株式会社 Composition de résine de poly(3-hydroxyalcanoate)
WO2015064566A1 (fr) * 2013-10-30 2015-05-07 日産化学工業株式会社 Composition de résine de poly(acide lactique) ayant une excellente résistance a l'hydrolyse

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BE789440A (fr) * 1971-09-30 1973-03-29 Ciba Geigy Sels de manganese (ii) d'hemi-esters phosphoniques utilisables comme stabilisants des polyamides

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Publication number Priority date Publication date Assignee Title
JPS6390560A (ja) * 1986-10-03 1988-04-21 Asahi Chem Ind Co Ltd ポリアミド樹脂組成物
WO2010131678A1 (fr) * 2009-05-12 2010-11-18 日産化学工業株式会社 Procédé pour la production de fines particules de sel métallique de l'acide phosphonique
WO2011030822A1 (fr) * 2009-09-09 2011-03-17 日産化学工業株式会社 Procédé de production de sel métallique d'acide phosphonique et composition de résine thermoplastique contenant du sel métallique d'acide phosphonique
WO2013047766A1 (fr) * 2011-09-30 2013-04-04 日産化学工業株式会社 Composition de résine de poly(3-hydroxyalcanoate)
WO2015064566A1 (fr) * 2013-10-30 2015-05-07 日産化学工業株式会社 Composition de résine de poly(acide lactique) ayant une excellente résistance a l'hydrolyse

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018009115A (ja) * 2016-07-14 2018-01-18 日産化学工業株式会社 ホスホン酸金属塩を含む芳香族ポリエーテルケトン樹脂組成物
CN109666294A (zh) * 2018-12-27 2019-04-23 会通新材料(上海)有限公司 一种结晶速率提升的聚酰胺56组合物及其应用
CN109666294B (zh) * 2018-12-27 2021-08-20 会通新材料(上海)有限公司 一种结晶速率提升的聚酰胺56组合物及其应用

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TW201741393A (zh) 2017-12-01
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