WO2000066356A1 - Produit en couches contenant une couche de caoutchouc perfluore et utilisation associee - Google Patents

Produit en couches contenant une couche de caoutchouc perfluore et utilisation associee Download PDF

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Publication number
WO2000066356A1
WO2000066356A1 PCT/JP2000/002801 JP0002801W WO0066356A1 WO 2000066356 A1 WO2000066356 A1 WO 2000066356A1 JP 0002801 W JP0002801 W JP 0002801W WO 0066356 A1 WO0066356 A1 WO 0066356A1
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WO
WIPO (PCT)
Prior art keywords
layer
rubber
vulcanization
perfluoro
parts
Prior art date
Application number
PCT/JP2000/002801
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English (en)
Japanese (ja)
Inventor
Katsusada Tokuhira
Yoshihiro Shirai
Yutaka Ueta
Original Assignee
Daikin Industries, Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Daikin Industries, Ltd. filed Critical Daikin Industries, Ltd.
Publication of WO2000066356A1 publication Critical patent/WO2000066356A1/fr

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Classifications

    • 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
    • B32B25/00—Layered products comprising a layer of natural or synthetic rubber
    • B32B25/04—Layered products comprising a layer of natural or synthetic rubber comprising rubber as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B25/08—Layered products comprising a layer of natural or synthetic rubber comprising rubber as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • 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
    • B32B27/32—Layered products comprising a layer of synthetic resin comprising polyolefins
    • B32B27/322—Layered products comprising a layer of synthetic resin comprising polyolefins comprising halogenated polyolefins, e.g. PTFE
    • 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
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/50—Properties of the layers or laminate having particular mechanical properties

Definitions

  • the present invention relates to a laminate including a perfluoro rubber layer, and more particularly, to a laminate in which a perfluoro rubber layer and a fluororesin layer are bonded by vulcanization.
  • Examples of commercially available molded articles using composite materials include hoses, diaphragms, sheets, and valves.
  • a diaphragm in which a laminate is used will be described as an example of a composite material.
  • a diaphragm coated with a fluororesin As a diaphragm having sufficient chemical resistance, a diaphragm coated with a fluororesin is commercially available. However, due to the characteristics of the fluororesin, sufficient sealing and durability cannot be provided to the diaphragm.
  • An object of the present invention is a laminate having a fluororesin layer, wherein the fluororesin layer has cracks.
  • An object of the present invention is to provide a laminate excellent in sealability and durability, which can maintain a function even when the laminate enters.
  • this object is achieved by a laminate comprising a perfluoro rubber layer, a fluororesin layer and, if necessary, an adhesive layer between these two layers.
  • the perfluoro rubber used in the present invention may be a known perfluoro rubber.
  • Preferred perfluoro rubbers are perfluoroalkylenes having 2 to 6 carbon atoms, preferably tetrafluoroethylene,
  • Rf represents a perfluoroalkyl group having 1 to 5 carbon atoms
  • X represents a fluorine atom or a trifluoromethyl group
  • n represents an integer of 0 to 4.
  • the ratio of the perfluoroalkylene, the perfluoroalkyl butyl ether (I) and the component providing the vulcanization site is arbitrary, and may be appropriately selected according to the properties required for the perfluoro rubber.
  • the ratio of PA Full O b component from 0.01 to 5 mole% giving an alkylene 35-95 mole 0/0 and Caro ⁇ position To polymerize.
  • R is a hydrocarbon group having 1 to 8 carbon atoms, a fluorohydrocarbon group or a cyclofluorohydrocarbon group, X is an integer of 0 to 2, y is an integer of 0 to 2, x + y is at least 1.
  • CF 2 CF-0 (CF 2 CFYO) a- (CF 2 CF 2 CH 2 0) b CF 2 CF 2 CH 2 Z
  • Y represents a fluorine atom or a trifluoromethyl group
  • ⁇ represents a hydrogen atom or a halogen atom
  • a represents an integer of 0 to 2
  • b represents an integer of 0 to 5.
  • X ′ is a hydrogen atom or a fluorine atom
  • Y ′ is a bromine atom or an iodine atom
  • m is an integer of 1 to 9.
  • the component providing a preferable vulcanization site is a perfluorophenoxy-substituted olefin.
  • the vulcanizing composition for perfluoro rubber contains perfluoro rubber, an organic peroxide and a polyfunctional unsaturated compound.
  • Particularly preferred perfluoro rubbers for the composition for peroxide vulcanization are copolymers of tetrafluoroethylene, perfluoroalkylbier ether (I) and the components providing the vulcanization sites exemplified above.
  • organic peroxides can be easily used in the presence of heat or a redox system. Those that generate dicals can be used.
  • Examples of preferred organic peroxides are 1,1-bis (t-butylbaroxy) -1,3,5,5-trimethylcyclohexane, 2,5-dimethinolehexane-1,2,5-dihydroperoxide, di-t-t-oxide.
  • polyfunctional unsaturated compound examples include a polyvalent vinyl compound, a polyvalent aryl compound, and a polyvalent (meth) acrylate.
  • Preferred examples include triallyl cyanurate, triallyl isocyanurate, fluorinated triallyl isocyanurate, triacryl formal, triallyl trimellitate, ethylene bismaleimide,
  • N, N'-m-phenylene bismaleimide dipropargyl terephthalate, diallyl phthalate, tetraaryl terephthalamide, tris (diallylamine) monos-triazine, triallyl phosphite, N, N-diallyl phosphite
  • Examples include acrylamide and trimethylolpropane trimethacrylate.
  • the amounts of rubber, organic peroxide and polyfunctional compound contained in the perfluoro rubber vulcanizing composition may be the same as in the conventional vulcanizing composition.
  • 0.05 to 10 parts by weight of organic peroxide preferably 0.5 to 5 parts by weight
  • 0.1 to 20 parts by weight of polyfunctional compound preferably 0.5 to 10 parts by weight
  • the vulcanization composition contains a perfluoro rubber and a polyhydroxy compound.
  • polyhydroxy compound a known polyhydroxy compound can be used.
  • preferred polyhydroxy compounds are bisphenol A, bisphenol AF or hydroquinone and their rhedium salts.
  • the amounts of the rubber and the polyhydroxy compound contained in the perfluoro rubber vulcanizing composition may be the same as in the case of the conventional vulcanizing composition.
  • 0.1 to 20 parts by weight of a polyhydroxy compound is blended per 100 parts by weight of rubber.
  • an acid acceptor such as magnesium oxide or calcium hydroxide may be used.
  • the vulcanization composition contains a perfluoro rubber and an organotin compound.
  • Particularly preferred perfluoro rubbers for triazine vulcanizing compositions are the copolymers of tetrafluoroethylene, perfluoroalkylbier ether (I) and the components providing the vulcanizing sites exemplified above.
  • a copolymer composed of tetrafluoroethylene; perfluoromethylbutyl ether; CF 2 CF—OCF 2 CF (CF 3 ) —OCF 2 CF (CF 3 ) CN is particularly preferred.
  • organic tin compound a known organic tin compound can be used.
  • preferred organotin compounds are triphenyltin, trioctyltin, dibutyltin dilaurate and the like.
  • the amounts of the rubber and the organotin compound contained in the perfluoro rubber vulcanizing composition may be the same as in the case of the conventional vulcanizing composition.
  • 0.1 to 20 parts by weight of an organotin compound is blended with respect to 100 parts by weight of rubber.
  • All of the above vulcanizing compositions may be blended with commonly used fillers, reinforcing agents, pigments, processing aids, stabilizers, and the like.
  • fillers, reinforcing agents, and pigments include carbon black, titanium oxide, silicon dioxide, talc, clay, calcium carbonate, diatomaceous earth, barium sulfate, and zinc oxide for inorganic substances, and polytetrafluoroethylene and polyvinylidenefur for organic substances.
  • fluorine-containing polymers such as ethylene, polychlorotrinoleoethylene, tetrafluoroethylene // ethylene copolymer, and tetrafluoroethylene z vinylidenefluoride copolymer.
  • the mixing means may be a commonly used method, such as an open roll or a closed type crusher.
  • the fluororesin used in the present invention includes tetrafluoroethylene (TFE), hexafluoropropylene (HFP), perfluorovinyl ether (PFVE), chlorotrinoleo ethylene (CTFE), trifleno ethylene ( At least one monomer selected from the group consisting of Tr FE), vinylidene fluoride (VDF) and vinyl fluoride (VF), or at least one monomer selected from the above group Is obtained by copolymerizing the above monomer and ethylene.
  • TFE tetrafluoroethylene
  • HFP hexafluoropropylene
  • PFVE perfluorovinyl ether
  • CTFE chlorotrinoleo ethylene
  • TFE tetrafluoroethylene
  • Tr FE hexafluoropropylene
  • PFVE perfluorovinyl ether
  • CTFE chlorotrinoleo ethylene
  • TFE tetrafluoroethylene
  • polytetrafluoroethylene PTFE
  • PCTFE polychlorinated trifluoroethylene
  • PVDF polyvinylidene fluoride
  • FEP tetrafluoroethylene-hexafluoropropylene copolymer
  • PFA Tetra-fluoro-ethylene-phenyl-fluoro-vinylene ether copolymer
  • ETFE ethylene-tetra-fluoro ethylene copolymer
  • bi-lidene fluoride-tetra-fluoro ethylene copolymer can do.
  • a perfluoro fluororesin such as PTFE, FEP, and PFA
  • PTFE fluororesin
  • FEP fluororesin
  • PFA perfluoro fluororesin
  • the surface treatment method is not particularly limited.
  • a method of performing an electric discharge treatment such as corona discharge in an inert gas atmosphere in the presence or absence of an organic compound Japanese Patent Publication No. 37-17485, Japanese Patent Publication No. JP-A-59-214620, JP-A-63-9533, JP-A-63-218336, JP-A-63-222838, etc.
  • a method of performing a flame treatment or a metal sodium treatment Japanese Patent Publication No. 63-10176
  • a method of performing a surface roughening treatment by sputtering, sand blasting or the like is known.
  • the adhesive layer formed as desired in the present invention may be one generally used as a resin or rubber adhesive layer, one containing a silane coupling agent as a main component, and one containing a curable resin such as an epoxy resin as a main component. Or those obtained by dissolving various rubbers in a solvent.
  • the surface treatment of the fluororesin and the adhesive layer may be used in combination.
  • a primer layer of an epoxy resin is formed on a modified surface, and then the epoxy resin is used as an adhesive.
  • ethylene-ethyl acrylate- A hot-melt adhesive such as maleic anhydride terpolymer and Z or ethylene-glycidyl methacrylate-butyl acetate terpolymer is used, and the method described in Japanese Patent Publication No. 63-110176 In this method, an adhesive containing an unsaturated polyester resin and an isocyanate compound is used.
  • Japanese Patent Application Laid-Open No. 63-9533 discloses a method of forming a primer layer of an epoxy resin on a modified surface, and laminating the primer layer with a thermoplastic polyester or a polyamide as an adhesive. Is described.
  • the laminate of the present invention can be used for oil-resistant, chemical-resistant, steam- or weather-resistant packing, O-rings, hoses, other sealing materials, diaphragms, valves, etc. in transportation such as automobiles, ships, and aircraft.
  • the laminated body of the present invention can be used for manufacturing devices such as a semiconductor, a liquid crystal panel, a plasma display panel, a plasma address liquid crystal panel, a field emission display panel, and a solar cell substrate, such as a CVD device, an etching device, and the like.
  • a CVD device such as a CVD device, an etching device, and the like.
  • O-rings sealing materials, hoses, tubes, diaphragms, and rolls for parts requiring chemical resistance, such as wet etchers, cleaning equipment, chemical liquid piping, and gas piping.
  • these devices can be used as non-dust, O-rings, seals, hoses, tubes, diaphragms, and rolls where metal-free is required.
  • parts requiring chemical resistance include O-rings, sealing materials, hoses, and tubes for resist developing solutions, stripping solutions, and cleaning solutions for wafers in manufacturing equipment such as semiconductors, liquid crystal valves, and plasma display panels. , A pump diaphragm, a roll for transporting a wafer, and the like.
  • the central part in the case of an O-ring or a square ring, can be formed of perfluoro rubber, and the entire circumference can be laminated so as to be surrounded by a fluororesin.
  • a fluororesin perfluoro rubber
  • the portion of the O-ring or the square ring that requires the fluororesin for example, only the portion that comes into contact with the corrosive fluid can be formed of the fluororesin layer.
  • the radially inner or outer surface of the ring may be formed of a fluororesin layer, and the other portions may be formed of a perfluoro rubber layer.
  • a perfluoro rubber is wrapped around a cored bar, and a fluororesin is further wrapped around the perforated rubber to form a rubber mouth.
  • one of the inner layer and the outer layer is a fluororesin layer, and the other is a perfluoro rubber layer.
  • at least one layer can be a fluororesin layer and the remaining layers can be a perfluoro rubber layer.
  • the innermost layer and the outermost layer which are in contact with the fluid flowing through the hose and the external atmosphere, respectively, are formed of fluorine resin, and the intermediate layer is formed of perfluoro rubber. Is preferred.
  • one layer is formed from fluorine resin and the other layer is formed from perfluoro rubber.
  • at least one layer can be a fluororesin layer and the remaining layers can be a perfluoro rubber layer.
  • the two outermost layers are formed of fluorine resin and the intermediate layer is formed of perfluoro rubber.
  • a reinforcing member such as cloth can be sandwiched between the rubber layers.
  • a medicine stopper it is preferable that a portion that comes into contact with the medicine is formed of a fluororesin layer.
  • the laminate of the present invention can be manufactured by various methods.
  • At least one surface of the fluororesin layer is subjected to a surface treatment, and an adhesive layer is further provided.
  • the two layers are overlapped so that the adhesive layer is in contact with the perfluoro rubber layer, and then the perfluoro rubber layer is vulcanized and bonded.
  • primary vulcanization can be performed to improve the dimensional accuracy of the laminate from which the perfluoro rubber layer can be obtained, or to improve moldability.
  • Vulcanization conditions can be selected according to the type of fluororesin and perfluoro rubber used, the type of vulcanizing system and vulcanizing agent used, and the type of molded product. Usually, the primary vulcanization is performed at a temperature of 100 to 230 ° C for 1 to 60 minutes, and the secondary vulcanization is performed at a temperature of 100 to 300 ° C for 0 to 48 hours.
  • the sample used for the test was prepared by the following method.
  • Tetrafluoroethylene // perfluoromethylbutyl ether copolymer containing 0.4 wt% of iodine as a perfluoroelastomer (molar ratio 60: 40.
  • Twenty-one viscosity 50) 100 parts by weight, MT carbon (Carbon black manufactured by CAN CARB) 20 parts by weight, triallyl isocyanurate (T AIC) 4 parts by weight, perhexa 25 B (2,5-dimethyl-2,5-di- (t-butylcarboxy) hexane; manufactured by NOF Corporation) 1.
  • a composition consisting of 5 parts by weight is converted to 10 OmmX. It was pre-grown into a sheet of 10 OmmX 2 mm.
  • Fluoro rubber (Daikin Industries, Ltd., Daiel G-751) 100 parts, MT force —20 parts of Bon Black (manufactured by CAN CAR B), 3 parts of magnesium oxide (highly active), 6 parts of calcium hydroxide
  • PTFE polytetrafluoroethylene
  • the obtained sheet was immersed in a commercially available treating agent (Tetra-etch: manufactured by Junye Co., Ltd.) for 5 seconds, and then washed with alcohol and then with water to obtain a fluororesin film whose surface was etched.
  • a commercially available treating agent Tetra-etch: manufactured by Junye Co., Ltd.
  • the surface-treated surface of the fluororesin 1 and the perfluoro rubber composition are superimposed, subjected to primary force vulcanization at 160 ° C for 10 minutes, and further subjected to secondary vulcanization at 180 ° C for 4 hours to measure the adhesive strength. Sample 1 was created.
  • a silane coupling agent (A-172, manufactured by Nippon Tunica Co., Ltd.) is applied to the surface-treated surface of the fluororesin 1 and dried, and then the perfluoro rubber composition is overlaid on the silane coupling agent-coated surface, Primary vulcanization was performed at 160 ° C for 10 minutes, and secondary vulcanization was performed at 180 ° C for 4 hours to prepare Sample 2 for measuring adhesive strength.
  • the surface-treated surface of the fluororesin 2 and the perfluoro rubber composition were superimposed, primary vulcanized at 160 ° C for 10 minutes, and secondary vulcanized at 180 ° C for 4 hours to prepare a sample 3 for measuring adhesive strength. .
  • a silane coupling agent (A-172, manufactured by Nippon Tunica Co., Ltd.) is applied to the surface-treated surface of the fluororesin 2 and dried, and then the perfluoro rubber composition is overlaid on the silane coupling agent-applied surface, and then heated at 160 ° C.
  • the sample was subjected to primary vulcanization at 1 ° C for 1 minute and then to secondary vulcanization at 180 ° C for 4 hours to prepare Sample 4 for measuring adhesive strength.
  • the adhesive strength after primary vulcanization and after secondary vulcanization is shown in Table 1 below.
  • a vulcanized rubber sheet of 10 OmmX 10 OmmX2 mmt was prepared according to the above-mentioned compounding and vulcanization conditions, immersed in each solvent at a predetermined temperature and time, and the volume increase rate was measured. The results are shown in Table 2 below.
  • perfluoro rubber has better resistance to toluene and acetone, which have greatly different polarities, than other rubber materials.
  • perfluoro rubber shows lower permanent deformation than fluororesin material and shows good durability.
  • the bending life was measured using a standard MIT bending tester described in ASTM D-2176-63T. The measurement was performed on a water-quenched film with a thickness of about 0.20 to 0.23 in the case of fluororesin. In the case of rubber, vulcanized rubber sheets of about 0.50 mm were used. A test piece of about 90 mm in length and about 12.7 mm in width was fastened to the jaw of the bending tester and positioned under a load of 1.25 kg. Using a MIT bending tester, bend the specimen to the left and right at an angle of 135 ° at a rate of about 175 cycles / minute. Record the number of cycles to failure in the counter attached to the tester.
  • the measurement was performed twice for each sample, and the average value was adopted as the MIT bending life of the sample. If the measurements differed by more than 25%, a third measurement of the MIT bending life was obtained and the average of all three measurements was taken as the bending life of the sample.
  • the perfluoro rubber showed a better MIT flex life than the fluororesin except PTFE. On the other hand, PTFE caused a creep phenomenon.

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  • Laminated Bodies (AREA)

Abstract

Ce produit en couches comprend une couche de caoutchouc perfluoré ainsi qu'une couche de résine fluorée, et, le cas échéant, une couche adhésive placée entre ces deux couches. Ce produit en couches peut conserver ses fonctions même après craquement de la couche de résine fluorée et il possède d'excellentes propriétés de scellement et de longévité et est conçu pour être utilisé dans la production, par exemple, d'un diaphragme.
PCT/JP2000/002801 1999-04-28 2000-04-28 Produit en couches contenant une couche de caoutchouc perfluore et utilisation associee WO2000066356A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11121733A JP2000313089A (ja) 1999-04-28 1999-04-28 パーフルオロゴム層の積層体およびその用途
JP11/121733 1999-04-28

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Publication Number Publication Date
WO2000066356A1 true WO2000066356A1 (fr) 2000-11-09

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3135485A4 (fr) * 2014-04-24 2017-11-29 Daikin Industries, Ltd. Stratifié
CN116814022A (zh) * 2023-07-05 2023-09-29 惠州市中茂科技有限公司 一种耐曲挠耐药液隔膜泵膜片及其制备方法

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5208512B2 (ja) 2004-11-30 2013-06-12 アーケマ・インコーポレイテッド 流体輸送用物体に有用なアロイ組成物
JP4945142B2 (ja) * 2006-02-06 2012-06-06 東海ゴム工業株式会社 液体封入型防振装置
JP2008296549A (ja) * 2007-06-04 2008-12-11 Daikin Ind Ltd パーフルオロエラストマー塗膜を有するフッ素樹脂成形品
JP5401954B2 (ja) * 2008-07-03 2014-01-29 ダイキン工業株式会社 ゴム層とフッ素樹脂層からなる積層体および加硫用ゴム組成物
EP2325252B1 (fr) 2008-09-09 2014-11-12 Daikin Industries, Ltd. Procédé de production de corps moulé réticulé en caoutchouc fluoré
DE102009003696A1 (de) * 2009-03-30 2010-10-07 Contitech Elastomer-Beschichtungen Gmbh Membran, insbesondere Gasspeichermembran
CN102471497B (zh) 2009-07-03 2014-10-22 大金工业株式会社 交联性氟橡胶组合物、氟橡胶成型品及其制法
WO2011123339A1 (fr) * 2010-03-29 2011-10-06 Greene, Tweed Of Delaware, Inc Compositions d'élastomère fluoré à caractéristiques autocollantes et leurs procédés de fabrication
ES2622005T3 (es) 2011-01-05 2017-07-05 Daikin Industries, Ltd. Artículo moldeado de caucho fluorado

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US4133927A (en) * 1975-10-23 1979-01-09 Kaikin Kogyo Co., Ltd. Composite material made of rubber elastomer and polytetrafluoroethylene resin
US4707387A (en) * 1985-10-17 1987-11-17 I.S.T. Corporation Composite rubber material and process for making same
US4931511A (en) * 1987-09-17 1990-06-05 Daikin Industries, Ltd. Cross-linkable coating composition
US5743170A (en) * 1996-03-27 1998-04-28 Wilden Pump & Engineering Co. Diaphragm mechanism for an air driven diaphragm pump

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4133927A (en) * 1975-10-23 1979-01-09 Kaikin Kogyo Co., Ltd. Composite material made of rubber elastomer and polytetrafluoroethylene resin
US4707387A (en) * 1985-10-17 1987-11-17 I.S.T. Corporation Composite rubber material and process for making same
US4931511A (en) * 1987-09-17 1990-06-05 Daikin Industries, Ltd. Cross-linkable coating composition
US5743170A (en) * 1996-03-27 1998-04-28 Wilden Pump & Engineering Co. Diaphragm mechanism for an air driven diaphragm pump

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3135485A4 (fr) * 2014-04-24 2017-11-29 Daikin Industries, Ltd. Stratifié
CN116814022A (zh) * 2023-07-05 2023-09-29 惠州市中茂科技有限公司 一种耐曲挠耐药液隔膜泵膜片及其制备方法
CN116814022B (zh) * 2023-07-05 2024-06-07 惠州市中茂科技有限公司 一种耐曲挠耐药液隔膜泵膜片及其制备方法

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