CN106268375A - A kind of preparation method of ion liquid functionalization polyphenylene sulfide porous film - Google Patents

A kind of preparation method of ion liquid functionalization polyphenylene sulfide porous film Download PDF

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CN106268375A
CN106268375A CN201610666062.5A CN201610666062A CN106268375A CN 106268375 A CN106268375 A CN 106268375A CN 201610666062 A CN201610666062 A CN 201610666062A CN 106268375 A CN106268375 A CN 106268375A
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pps
perforated membrane
ion liquid
preparation
porous film
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CN106268375B (en
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苏坤梅
王超
李振环
牛晓燕
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Taiyuan Jin Hua Heng Yuan Technology Co Ltd
Tianjin Polytechnic University
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Taiyuan Jin Hua Heng Yuan Technology Co Ltd
Tianjin Polytechnic University
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06—Organic material
    • B01D71/66—Polymers having sulfur in the main chain, with or without nitrogen, oxygen or carbon only
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
    • B01D67/0002—Organic membrane manufacture
    • B01D67/0006—Organic membrane manufacture by chemical reactions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
    • B01D67/0002—Organic membrane manufacture
    • B01D67/0009—Organic membrane manufacture by phase separation, sol-gel transition, evaporation or solvent quenching
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
    • B01D69/02—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor characterised by their properties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2323/00—Details relating to membrane preparation
    • B01D2323/38—Graft polymerization
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2325/00—Details relating to properties of membranes
    • B01D2325/02—Details relating to pores or porosity of the membranes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2325/00—Details relating to properties of membranes
    • B01D2325/22—Thermal or heat-resistance properties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2325/00—Details relating to properties of membranes
    • B01D2325/30—Chemical resistance
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2325/00—Details relating to properties of membranes
    • B01D2325/48—Antimicrobial properties

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Dispersion Chemistry (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)

Abstract

The invention discloses the preparation method of a kind of ion liquid functionalization polyphenylene sulfide porous film.PPS resin, diluent, inorganic nanoparticles and additive are first mixed to get PPS casting solution by the method；Immersion precipitation phase inversion process is then utilized to make PPS perforated membrane；Then PPS porous film surface is carried out haloalkylation reaction, then the alkyl halide of PPS porous film surface is reacted with organic amine again, obtain the PPS perforated membrane of ion liquid functionalization.The ion liquid functionalization PPS perforated membrane that the method prepares not only has excellent for PPS solvent resistant, the characteristic such as corrosion-resistant and high temperature resistant, and improve the hydrophilicity and hydrophobicity on film surface, membrane aperture is reduced, forms nanoscale aperture, and then realize the Selective Separation of solvent.

Description

A kind of preparation method of ion liquid functionalization polyphenylene sulfide porous film
Technical field
The present invention relates to functional polymer film field of material preparation, specifically a kind of ion liquid functionalization polyphenylene sulfide is many The preparation method of pore membrane.
Background technology
Polyphenylene sulfide (being called for short PPS) is the macromolecule engineering material with good thermostability and superior resistance to chemical corrosion Material, owing to it has high temperature resistant, corrosion-resistant, radiation hardness, solvent resistant and the feature such as fire-retardant, therefore extensively applies in modern industry In aspects such as electronic apparatus, automobile, Aero-Space, petrochemical industry, machinery, chemical fibres.Along with the development of PPS material property, It is applied at aspects such as high temperature, acid-fast alkali-proof, radiation hardness and solvent resistant as a kind of novel membrane material, as with In high temperature or the directly process of corrosive waste (waste water or spent organic solvent, even waste gas).
Generally, the aperture of PPS perforated membrane is relatively large, not retains ion and solution or osmosis, for Preferably organic solution or ionic compound are separated, improve and retain efficiency, need on the basis of PPS perforated membrane, To it, modified or grafting, forms the LBL self-assembly of chemical molecular chain, indirectly changes the size of membrane aperture so that pore-size distribution The uniformity improves.Meanwhile, PPS film has certain hydrophobicity, after PPS film surface ion liquid functionalization, is conducive to improving PPS The hydrophilic of film, thus improve the resistance tocrocking of film.
Summary of the invention
For the deficiencies in the prior art, the technical problem that the present invention intends to solve is to provide a kind of ion liquid functionalization and gathers The preparation method of diphenyl sulfide perforated membrane.The method first carries out haloalkylation to PPS porous film surface, then by PPS porous film surface Alkyl halide react with organic amine again, obtain the PPS perforated membrane of ion liquid functionalization.The ionic liquid function that the method prepares Change PPS perforated membrane and not only there is excellent for PPS solvent resistant, the characteristic such as corrosion-resistant and high temperature resistant, and improve the parent on film surface Hydrophobic performance so that membrane aperture reduces, forms nanoscale aperture, and then realizes the Selective Separation of solvent.
The present invention solves the technical scheme of described technical problem and is to provide a kind of ion liquid functionalization polyphenylene sulfide porous The preparation method of film, it is characterised in that specifically include following steps:
1) preparation of PPS perforated membrane: by mass fraction be the PPS resin of 20%-40%, mass fraction be 53.9%- The diluent of 68%, mass fraction are the inorganic nanoparticles of 0.1%-2% and the additive that mass fraction is 6%-10% mixes Conjunction is warming up to 240-320 DEG C, stirs 5-30 minute, standing and defoaming, obtains PPS casting solution；Then utilize immersion precipitation inversion of phases Method makes PPS perforated membrane；
Described diluent is at least one of benzophenone, diphenyl sulphone (DPS) or caprolactam；Described additive is O-phthalic At least one of dibutyl phthalate, anhydrous Lithium chloride, dodecylbenzene sodium sulfonate or Polyethylene Glycol；Described inorganic nanoparticles is SiO2Or graphene oxide；
2) the haloalkylation reaction of PPS perforated membrane: by 1-10gPPS perforated membrane and 10-100ml alkyl halide, with 0.1-1g halogen Compound is catalyst, reacts 1-48h at a temperature of 50 DEG C-80 DEG C；Be washed out, sucking filtration, vacuum drying obtain haloalkylation PPS film；
Described halogenide is ZnCl2、ZnBr2、AlCl3、AlBr3、FeCl3、FeBr3、SnBr4Or SnCl4At least one； Described alkyl halide is dichloromethane, methylene bromide, 1,2-dichloroethanes, glycol dibromide, 1,3-dichloropropane, 1,3-dibromo Propane, 1,4-dichloroetane, 1,4-dibromobutane, 1,5-dichloropentane, pentamethylene bromide, 1,6-dichloro hexane or 1,6-bis- At least one in chlorohexane；
3) preparation of ion liquid functionalization PPS perforated membrane: by 1-10g haloalkylation PPS perforated membrane, 20-100ml halo Hydrocarbon liquid and 0.1-5g reagent A react 1-48h at 40-120 DEG C；Ion liquid functionalization PPS perforated membrane is obtained after washing；
Described halogenated hydrocarbons liquid is CCl4, chloroform, dichloromethane, 1-chloromethanes, 1,2-dichloroethanes, four chloroethenes Alkane, hexachlorethane, CBr4, bromoform, methylene bromide, 1-bromomethane, glycol dibromide or tetrabromoethane at least one； Described reagent A is at least one in alkyl imidazole, tertiary ammonia, pyridine or pyridine derivate；Described alkyl imidazole be Methylimidazole., Ethyl imidazol(e), propyl imidazole or 1-Butyl-1H-imidazole；Described tertiary ammonia is trimethylamine, triethylamine, tripropyl amine (TPA) or tri-n-butylamine；Described pyridine spreads out Biology is 2-picoline, 3-picoline, 2-ethylpyridine, 3-ethylpyridine, 2-butyl-pyridinium or 3-butyl-pyridinium.
Compared with prior art, the present invention has the beneficial effects that: this method is by PPS fenestra road outer surface grafting halo Alkane, and then prepare ion liquid functionalization PPS film with alkyl imidazole, tertiary ammonia or pyridine and its derivatives reaction.This ionic liquid Functionalization polyphenylene sulfide porous film pore distribution is narrow, mainly based on nano-micro level duct, water contact angle between 30-70 °, and The ion liquid type compound of surface graft has excellent antibacterial ability so that PPS film has good contamination resistance, has Effect achieves the Selective Separation of organic micromolecule compound or inorganic salt.
Detailed description of the invention
The specific embodiment of the present invention is given below.Specific embodiment is only used for further describing the present invention, does not limits The application scope of the claims processed.
The invention provides the preparation method of a kind of ion liquid functionalization polyphenylene sulfide porous film, it is characterised in that concrete Comprise the following steps:
(1) preparation of PPS perforated membrane: by mass fraction be the PPS resin of 20%-40%, mass fraction be 53.9%- The diluent of 68%, mass fraction are the inorganic nanoparticles of 0.1%-2% and the additive that mass fraction is 6%-10% mixes Conjunction is warming up to 240-320 DEG C, stirs 5-30 minute, standing and defoaming, obtains PPS casting solution；Then utilize immersion precipitation inversion of phases Method makes PPS perforated membrane；
Described diluent is at least one of benzophenone, diphenyl sulphone (DPS) or caprolactam；Described additive is O-phthalic At least one of dibutyl phthalate, anhydrous Lithium chloride, dodecylbenzene sodium sulfonate or Polyethylene Glycol；Described inorganic nanoparticles is SiO2Or graphene oxide (GO)；
(2) the haloalkylation reaction of PPS perforated membrane: by 1-10g PPS perforated membrane and 10-100ml alkyl halide, with 0.1-1g Halogenide is catalyst, reacts 1-48h at a temperature of 50 DEG C-80 DEG C；Then soak with dilute hydrochloric acid and remove PPS porous film surface On residual organic solvent, go out the organic solvent of residual after deionized water wash with ethanolic extraction, scrubbed, sucking filtration, vacuum are dry Dry obtain haloalkylation PPS film；
Described alkyl halide be dichloromethane, methylene bromide, 1,2-dichloroethanes, glycol dibromide, 1,3-dichloropropane, 1,3-dibromopropane, 1,4-dichloroetane, 1,4-dibromobutane, 1,5-dichloropentane, pentamethylene bromide, 1,6-dichloro hexane Or at least one in 1,6-dichloro hexane；Described halogenide is ZnCl2、ZnBr2、AlCl3、AlBr3、FeCl3、FeBr3、 SnBr4Or SnCl4At least one；
(3) preparation of ion liquid functionalization PPS perforated membrane: by 1-10g haloalkylation PPS perforated membrane, 20-100ml halogen At 40-120 DEG C, 1-48h is reacted for hydrocarbon liquid and 0.1-5g reagent A；Then with little molecular polarity compound such as ethanol, methanol Wash to neutral with deionized water etc., obtain ion liquid functionalization PPS perforated membrane；
Described halogenated hydrocarbons liquid is CCl4, chloroform, dichloromethane, 1-chloromethanes, 1,2-dichloroethanes, four chloroethenes Alkane, hexachlorethane, CBr4, bromoform, methylene bromide, 1-bromomethane, glycol dibromide or tetrabromoethane at least one； Described reagent A is at least one in alkyl imidazole, tertiary ammonia, pyridine or pyridine derivate；Described alkyl imidazole be Methylimidazole., Ethyl imidazol(e), propyl imidazole or 1-Butyl-1H-imidazole；Described tertiary ammonia is trimethylamine, triethylamine, tripropyl amine (TPA) or tri-n-butylamine；Described pyridine spreads out Biology is 2-picoline, 3-picoline, 2-ethylpyridine, 3-ethylpyridine, 2-butyl-pyridinium or 3-butyl-pyridinium.
Embodiment 1
(1) by 28wt%PPS, 54wt% benzophenone, 12wt% dibutyl phthalate, 4wt% anhydrous Lithium chloride (LiCl), 0.5wt% dodecylbenzene sodium sulfonate, 1wt% Polyethylene Glycol (PEG), 0.5wt% silicon dioxide (SiO2) mixing liter Temperature, to 260 DEG C, stirs 10 minutes, standing and defoaming, obtains PPS casting solution；Then immersion precipitation phase inversion process is utilized to make PPS many Pore membrane；
(2) by 5gPPS perforated membrane, 20ml dichloromethane and 0.5g catalyst SnCl4After reacting 4h at a temperature of 60 DEG C； Be washed out, sucking filtration, vacuum drying obtain haloalkylation PPS perforated membrane；
(3) by 5g haloalkylation PPS perforated membrane, 50mlCCl4At 50 DEG C, 12h is reacted, after washing with 1gN-Methylimidazole. Obtain ion liquid functionalization PPS perforated membrane.
It is 15-30nm that mercury injection method records film average pore size, porosity 64-72%, and pure water flux is 280L/m2·h。
Embodiment 2
(1) by 28wt%PPS, 54wt% diphenyl sulphone (DPS), 12wt% dibutyl phthalate, 4wt% anhydrous Lithium chloride (LiCl), 0.5wt% dodecylbenzene sodium sulfonate, 1wt% Polyethylene Glycol (PEG), the mixing of 0.5wt% graphene oxide are warming up to 260 DEG C, stir 10 minutes, standing and defoaming, obtain PPS casting solution；Immersion precipitation phase inversion process is then utilized to make PPS porous Film；
(2) by 5gPPS perforated membrane, 20ml1,2-dichloroethanes and 0.5g catalyst Z nCl2React at a temperature of 70 DEG C After 5h；Be washed out, sucking filtration, vacuum drying obtain haloalkylation PPS perforated membrane；
(3) by 5g haloalkylation PPS perforated membrane, 50mlCCl4At 50 DEG C, react 12h with 1.5g pyridine, obtain after washing Ion liquid functionalization PPS perforated membrane.
It is 20-35nm that mercury injection method records film average pore size, porosity 68-80%, and pure water flux is 255L/m2·h。
Embodiment 3
(1) by 28wt%PPS, 54wt% caprolactam, 12wt% dibutyl phthalate, 4wt% anhydrous Lithium chloride (LiCl), 0.5wt% dodecylbenzene sodium sulfonate, 1wt% Polyethylene Glycol (PEG), the mixing of 0.5wt% graphene oxide are warming up to 270 DEG C, stir 10 minutes, standing and defoaming, obtain PPS casting solution；Immersion precipitation phase inversion process is then utilized to make PPS porous Film；
(2) by 5gPPS perforated membrane, 20ml1,5-dichloropentane and 1g catalyst Z nCl25h is reacted at a temperature of 80 DEG C After；Be washed out, sucking filtration, vacuum drying obtain haloalkylation PPS perforated membrane；
(3) by 5g haloalkylation PPS perforated membrane, 50mlCCl4At 50 DEG C, react 12h with 1g triethylamine, obtain after washing Ion liquid functionalization PPS perforated membrane.
It is 33-50nm that mercury injection method records film average pore size, porosity 72-85%, and pure water flux is 290L/m2·h。
Embodiment 4
(1) by 28wt%PPS, 54wt% benzophenone, 12wt% dibutyl phthalate, 4wt% anhydrous Lithium chloride, The mixing of 0.5wt% dodecylbenzene sodium sulfonate, 1wt% Polyethylene Glycol (PEG), 0.5wt% silicon dioxide is warming up to 280 DEG C, stirs Mix 10 minutes, standing and defoaming, obtain PPS casting solution；Immersion precipitation phase inversion process is then utilized to make PPS perforated membrane；
(2) by 5gPPS perforated membrane, 20ml methylene bromide and 1g catalyst SnBr4After reacting 4h at a temperature of 80 DEG C；So Rear washing, sucking filtration, vacuum drying obtain haloalkylation PPS perforated membrane；
(3) by 5g haloalkylation PPS perforated membrane, 50mlCBr4At 50 DEG C, react 12h with 1.5g N-Methylimidazole., wash Ion liquid functionalization PPS perforated membrane is obtained after washing.
It is 12-28nm that mercury injection method records film average pore size, porosity 60-70%, and pure water flux is 220L/m2·h。
Embodiment 5
(1) by 28wt%PPS, 54wt% benzophenone, 12wt% dibutyl phthalate, 4wt% anhydrous Lithium chloride, The mixing of 0.5wt% dodecylbenzene sodium sulfonate, 1wt% Polyethylene Glycol, 0.5wt% silicon dioxide is warming up to 260 DEG C, stirs 10 points Clock, standing and defoaming, obtain PPS casting solution；Immersion precipitation phase inversion process is then utilized to make PPS perforated membrane；
(2) by 5gPPS perforated membrane, 20ml1,4-dichloroetane and 1g catalyst Fe Cl34h is reacted at a temperature of 80 DEG C After；Be washed out, sucking filtration, vacuum drying obtain haloalkylation PPS perforated membrane；
(3) 5g haloalkylation PPS perforated membrane, 50ml chloroform and 1.5g triethylamine are reacted 12h at 50 DEG C, after washing To ion liquid functionalization PPS perforated membrane.
It is 10-25nm that mercury injection method records film average pore size, porosity 58-65%, and pure water flux is 240L/m2·h。
The present invention does not addresses part and is applicable to prior art.

Claims (4)

1. the preparation method of an ion liquid functionalization polyphenylene sulfide porous film, it is characterised in that comprise the following steps:
1) preparation of PPS perforated membrane: by mass fraction be the PPS resin of 20%-40%, mass fraction be 53.9%-68%'s Diluent, mass fraction are the inorganic nanoparticles of 0.1%-2% and the mixing of additive that mass fraction is 6%-10% heats up To 240-320 DEG C, stir 5-30 minute, standing and defoaming, obtain PPS casting solution；Immersion precipitation phase inversion process is then utilized to make PPS perforated membrane；
Described diluent is at least one of benzophenone, diphenyl sulphone (DPS) or caprolactam；Described additive is phthalic acid two At least one of butyl ester, anhydrous Lithium chloride, dodecylbenzene sodium sulfonate or Polyethylene Glycol；Described inorganic nanoparticles is SiO2Or Graphene oxide；
2) the haloalkylation reaction of PPS perforated membrane: by 1-10gPPS perforated membrane and 10-100ml alkyl halide, with 0.1-1g halogenide For catalyst, at a temperature of 50 DEG C-80 DEG C, react 1-48h；Be washed out, sucking filtration, vacuum drying obtain haloalkylation PPS Film；
3) preparation of ion liquid functionalization PPS perforated membrane: by 1-10g haloalkylation PPS perforated membrane, 20-100ml halogenated hydrocarbons liquid Body and 0.1-5g reagent A react 1-48h at 40-120 DEG C；Ion liquid functionalization PPS perforated membrane is obtained after washing；
Described reagent A is at least one of alkyl imidazole, tertiary ammonia, pyridine or pyridine derivate；Described alkyl imidazole is methyl miaow Azoles, ethyl imidazol(e), propyl imidazole or 1-Butyl-1H-imidazole；Described tertiary ammonia is trimethylamine, triethylamine, tripropyl amine (TPA) or tri-n-butylamine；Described pyrrole Piperidine derivatives is 2-picoline, 3-picoline, 2-ethylpyridine, 3-ethylpyridine, 2-butyl-pyridinium or 3-butyl-pyridinium.
The preparation method of ion liquid functionalization polyphenylene sulfide porous film the most according to claim 1, it is characterised in that step Rapid 2) halogenide described in is ZnCl2、ZnBr2、AlCl3、AlBr3、FeCl3、FeBr3、SnBr4Or SnCl4At least one.
The preparation method of ion liquid functionalization polyphenylene sulfide porous film the most according to claim 1, it is characterised in that step Rapid 2) alkyl halide described in be dichloromethane, methylene bromide, 1,2-dichloroethanes, glycol dibromide, 1,3-dichloropropane, 1, 3-dibromopropane, 1,4-dichloroetane, 1,4-dibromobutane, 1,5-dichloropentane, pentamethylene bromide, 1,6-dichloro hexane or At least one of 1,6-dichloro hexane.
The preparation method of ion liquid functionalization polyphenylene sulfide porous film the most according to claim 1, it is characterised in that step Rapid 3) halogenated hydrocarbons liquid described in is CCl4, chloroform, dichloromethane, 1-chloromethanes, 1,2-dichloroethanes, sym-tetrachloroethane, Hexachlorethane, CBr4, bromoform, methylene bromide, 1-bromomethane, glycol dibromide or tetrabromoethane at least one.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110404424A (en) * 2019-06-17 2019-11-05 沈阳工业大学 Mixed substrate membrane containing nano-grade molecular sieve and preparation method and applications
CN113948818A (en) * 2021-11-17 2022-01-18 北京胜能能源科技有限公司 Polyphenylene sulfide composite diaphragm and preparation method and application thereof
CN114744368A (en) * 2022-06-13 2022-07-12 四川新能源汽车创新中心有限公司 Lithium battery diaphragm with compact structure and preparation method thereof

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CN104151599A (en) * 2014-07-18 2014-11-19 复旦大学 Ionic liquid functionalized temperature-responsive composite film and preparation method thereof
CN104437119A (en) * 2014-11-05 2015-03-25 福州大学 Polymer microporous membrane based on polyvinyl chloride ion liquid and preparation method of polymer microporous membrane
CN104817714A (en) * 2015-03-25 2015-08-05 沈阳化工大学 Adamantane structure-containing polyarylether anion-exchange membrane and preparation method thereof
CN105148750A (en) * 2015-08-21 2015-12-16 浙江大学 Method for modifying surface of polyamide composite film

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JPS62258711A (en) * 1986-05-01 1987-11-11 Asahi Chem Ind Co Ltd Production of grafted membrane
CN104151599A (en) * 2014-07-18 2014-11-19 复旦大学 Ionic liquid functionalized temperature-responsive composite film and preparation method thereof
CN104437119A (en) * 2014-11-05 2015-03-25 福州大学 Polymer microporous membrane based on polyvinyl chloride ion liquid and preparation method of polymer microporous membrane
CN104817714A (en) * 2015-03-25 2015-08-05 沈阳化工大学 Adamantane structure-containing polyarylether anion-exchange membrane and preparation method thereof
CN105148750A (en) * 2015-08-21 2015-12-16 浙江大学 Method for modifying surface of polyamide composite film

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110404424A (en) * 2019-06-17 2019-11-05 沈阳工业大学 Mixed substrate membrane containing nano-grade molecular sieve and preparation method and applications
CN110404424B (en) * 2019-06-17 2021-12-14 沈阳工业大学 Mixed matrix membrane and preparation method and application thereof
CN113948818A (en) * 2021-11-17 2022-01-18 北京胜能能源科技有限公司 Polyphenylene sulfide composite diaphragm and preparation method and application thereof
CN114744368A (en) * 2022-06-13 2022-07-12 四川新能源汽车创新中心有限公司 Lithium battery diaphragm with compact structure and preparation method thereof
CN114744368B (en) * 2022-06-13 2022-08-30 四川新能源汽车创新中心有限公司 Lithium battery diaphragm with compact structure and preparation method thereof

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