WO2018000361A1 - Procédé de préparation d'une membrane composite de nanofiltration au polysulfonamide ou d'osmose inverse par assemblage de couches moléculaires - Google Patents

Procédé de préparation d'une membrane composite de nanofiltration au polysulfonamide ou d'osmose inverse par assemblage de couches moléculaires Download PDF

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WO2018000361A1
WO2018000361A1 PCT/CN2016/087981 CN2016087981W WO2018000361A1 WO 2018000361 A1 WO2018000361 A1 WO 2018000361A1 CN 2016087981 W CN2016087981 W CN 2016087981W WO 2018000361 A1 WO2018000361 A1 WO 2018000361A1
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preparation
polysulfonamide
solution
nanofiltration
reverse osmosis
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PCT/CN2016/087981
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English (en)
Chinese (zh)
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牛青山
袁涛
胡月芳
郭鑫
李鹏
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中国石油大学(华东)
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Priority to PCT/CN2016/087981 priority Critical patent/WO2018000361A1/fr
Priority to CN201680003641.XA priority patent/CN106999870A/zh
Publication of WO2018000361A1 publication Critical patent/WO2018000361A1/fr

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    • 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
    • B01D69/12—Composite membranes; Ultra-thin membranes
    • B01D69/1214—Chemically bonded layers, e.g. cross-linking
    • 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
    • B01D69/12—Composite membranes; Ultra-thin membranes
    • 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
    • B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
    • B01D71/82—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74 characterised by the presence of specified groups, e.g. introduced by chemical after-treatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
    • B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
    • B01D61/025—Reverse osmosis; Hyperfiltration
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
    • B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
    • B01D61/027—Nanofiltration
    • 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
    • B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
    • B01D69/10—Supported membranes; Membrane supports
    • B01D69/105—Support pretreatment
    • 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
    • B01D69/12—Composite membranes; Ultra-thin membranes
    • B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
    • 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
    • B01D71/56—Polyamides, e.g. polyester-amides
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/44—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis

Definitions

  • the invention relates to a preparation technology of a polymer composite membrane, in particular to a preparation method of a polysulfonamide nanofiltration or reverse osmosis composite membrane which is resistant to acid, alkali, oxidation and surface roughness.
  • Aramid interfacial polymerization technology has been widely used in the field of water treatment such as seawater desalination, reclaimed water, sewage treatment, drinking water preparation, etc. Applications.
  • the performance of membrane materials is also constantly being optimized.
  • membrane surface modification and doping of nanoparticles have become hot research directions to further improve the comprehensive performance of reverse osmosis or nanofiltration composite membrane materials (CN104028126, CN102294178 and literature). Reports Journal of Membrane Science, 320, (2008), Polymer, 48, (2007), Journal of Membrane Science, 367, (2011), Desalination 219, (2008), etc.).
  • the surface functional cortex of the mainstream roll-type nanofiltration or reverse osmosis composite membrane on the market is still based on polyamide formed by polyacid chloride (such as 1,3,5-benzenetricarboxylic acid chloride) and polyamine (such as m-phenylenediamine or piperazine).
  • a crosslinked network structure is prepared (US Pat. No. 5,693,227, US Pat. No. 4,769,148, US Pat. No. 5,152,901).
  • the above monomers are also considered to be the most effective for the preparation of nanofiltration or reverse osmosis membranes by interfacial polymerization.
  • the amide bond in the polyamide structure is hydrolyzed under low and high pH conditions, which restricts the application of the above composite film in harsh environments. Therefore, it is of great practical significance to develop new nanofiltration or reverse osmosis membrane materials and their key preparation techniques that are widely applicable to complex fluids, especially various acid-base industrial fluids.
  • the polysulfonamide structure has excellent acid and alkali resistance, thermal stability and oxidation resistance, and is used for interfacial polymerization preparation of novel nanofiltration or reverse osmosis composite membranes.
  • Patent US6783711 US6873996, US20120152839, CN102120149, etc. and literature Journal of Membrane Science, 143, 181 (1998), Journal of Applied Polymer Science, 48, 187 (1993), Journal of Applied Polymer Science, 54, 1233, (1994), Journal of Applied Polymer Science, 64 , 2381 (1997), etc. have reported the study of interfacial polymerization to prepare polysulfonamide nanofiltration or reverse osmosis membranes.
  • the commercial products of nanofiltration or reverse osmosis membranes based on polysulfonamide structure are still few, mainly due to the poor desalination performance of the composite membrane and low flux.
  • the polysulfonamide has a lower interfacial polymerization activity than the polyamide monomer.
  • the traditional interfacial polymerization technique for preparing polysulfonamide composite membranes is difficult to obtain stable and high membrane separation performance.
  • the performance improvement of polysulfonamide nanofiltration or reverse osmosis membrane materials is still by exploring the best catalyst or acid absorber, increasing the monomer concentration or increasing the heat treatment temperature.
  • the molecular layer assembly technique can effectively compensate for the problem of poor salt rejection of the selective functional layer prepared by crosslinking of the lower reactive monomer.
  • the molecular layer layer assembly preparation composite membrane technology of the invention can effectively compensate for the defects existing in the preparation of the polysulfonamide nanofiltration or reverse osmosis composite membrane by the interfacial polymerization process, so as to achieve higher desalination performance.
  • the present technology is applicable to the layered assembly preparation of composite functional layers between a plurality of low reactivity monomers. Both the reported sulfonyl chloride and polyamine monomers can be used in the preparation of polysulfonamide nanofiltration or reverse osmosis composite membranes using the techniques of the present invention.
  • the invention is directed to the deficiencies of the prior art, and proposes a new method for preparing a polysulfonamide nanofiltration or reverse osmosis composite membrane, and uses the technology to prepare a polysulfonamide having high desalination performance, a smoother membrane surface and lower roughness. Nanofiltration or reverse osmosis membrane.
  • the technical problem to be solved by the present invention is to provide a method for preparing a polysulfonamide nanofiltration or reverse osmosis composite membrane having a simple operation process, high desalination property and low surface roughness.
  • the invention relates to a method for preparing a polysulfonamide nanofiltration or reverse osmosis composite membrane, which is characterized in that the polyamine and the polysulfonyl chloride layer are assembled on the surface of the porous support membrane to form a multilayer crosslinked polysulfonamide according to the principle of molecular layer assembly.
  • the covalent structure gives a polysulfonamide selective functional layer.
  • the method for preparing a polysulfonamide nanofiltration or reverse osmosis composite membrane layer assembly comprises the steps of: molecularly layering a porous support membrane in a solution of a sulfonyl chloride and a polyamine monomer, wherein the concentration of the sulfonyl chloride solution is 0.001%- 5%, the concentration of the sulfonyl chloride in the present invention is preferentially controlled in the range of 0.001% to 1%, the concentration of the polyamine monomer is 0.001% to 15%, and the concentration preferential control range of the present invention is 0.001% to 5%; heat treatment at 40-110 ° C, Wash thoroughly after washing.
  • the molecular layer layer assembly is performed by alternately immersing the porous support film in a solution of a sulfonyl chloride and a polyamine monomer, or uniformly spraying a solution of a sulfonyl chloride and a polyamine monomer on the surface of the porous support film, or by spin coating with a uniform rubber.
  • the method is carried out by spin-coating a solution of a sulfonyl chloride and a polyamine monomer on the surface of the porous support layer.
  • the heat treatment process for preparing the polysulfonamide nanofiltration or reverse osmosis membrane may be performed by immersing, spraying or spin-coating the polysulfonamide structure, or by immersing, spraying or spin coating to assemble a plurality of polysulfonamide structures. .
  • the technical solution includes a porous support membrane pretreatment step.
  • the pretreatment is to wash the porous support membrane with 30-50% aqueous solution of isopropanol or 30-50% aqueous solution of ethanol, and finally rinsed with pure water for use.
  • the technical solution layer is assembled to prepare a polysulfonamide nanofiltration or reverse osmosis composite membrane, and the number of assembled layers ranges from 1 to 50 layers.
  • the technical solution includes adding 0.0%-5% of the nanoparticles to form a polysulfonamide nanofiltration or reverse osmosis composite membrane in a polyamine monomer solution or a sulfonyl chloride monomer solution, and the nanoparticle addition range of the invention The preference is 0.0%-1%.
  • the range of nanoparticles in the technical solution includes known pores or nonporous, cyclic or acyclic Morphological inorganic or organic nanoscale particles.
  • the technical solution comprises introducing a polymer coating during the layer assembly preparation process of the polysulfonamide nanofiltration or reverse osmosis composite membrane to improve the performance of the composite membrane.
  • the polymer may be polyvinyl alcohol (PVA), polyethyleneimine (PEI), polylactic acid (PLA), polyacrylic acid (PAA), poly(2-alkyl-2-oxazoline) (POX), and Other coating materials that are not specified but can serve the same purpose.
  • PVA polyvinyl alcohol
  • PEI polyethyleneimine
  • PLA polylactic acid
  • PAA polyacrylic acid
  • POX poly(2-alkyl-2-oxazoline)
  • the introduction of the polymer coating can be carried out before the layer assembly preparation process, after the layer assembly preparation process, and during the layer assembly preparation process.
  • polysulfonamide nanofiltration or reverse osmosis composite membrane preparation method characterized in that the polysulfonamide structure is formed by a molecular layer assembly process, and the following three layer assembly methods are merely illustrative and not limiting:
  • the porous support membrane is alternately immersed in a solution of a sulfonyl chloride and a polyamine monomer, the concentration of the sulfonyl chloride is 0.001% to 1%, and the concentration of the polyamine monomer is 0.001% to 5%.
  • the alternating soak assembly step is repeated a plurality of times.
  • the sulfonyl chloride and polyamine monomer solution are uniformly sprayed on the surface of the porous support film, the concentration of the sulfonyl chloride is 0.001% to 1%, and the concentration of the polyamine monomer is 0.001% to 5%.
  • the spray assembly step is cycled multiple times. Heat treatment at 40-110 ° C for 1-20 min, the heat treatment process can be carried out in the spray assembly polysulfonamide structure, or after assembling a multi-layer polysulfonamide structure. Finally, it was washed thoroughly with an aqueous ethanol solution for 30-60 min.
  • the sulfonyl chloride and the polyamine monomer solution are respectively spin-coated on the surface of the porous support layer by a spin coating method, the concentration of the sulfonyl chloride is 0.001% to 1%, and the concentration of the polyamine monomer is 0.001% to 5%.
  • the spin coating assembly step Heat treatment at 40-110 °C for 1-20 min, the heat treatment process can be carried out in the spin-coating polysulfonamide structure or after assembling a multi-layer polysulfonamide structure. Finally, it was washed thoroughly with an aqueous ethanol solution for 30-60 min.
  • the spin-coating layer for the preparation of polysulfonamide nanofiltration or reverse osmosis membranes is suitable for the production or modification of equipment according to the principles mentioned in the patent CN 204247481 U.
  • the porous support membrane of the polysulfonamide nanofiltration or reverse osmosis composite membrane of the present invention may be characterized by an organic polymer porous membrane such as polysulfone, polyethersulfone, polyacrylonitrile or the like, or an inorganic porous membrane such as ceramic. Membrane and the like.
  • the polysulfone porous membrane is preferably used in the present invention.
  • the invention relates to a method for preparing a polysulfonamide nanofiltration or reverse osmosis composite membrane, wherein the polysulfonyl chloride is a structure containing two or more "SO2" groups and linking a fat group, a phenyl group, a biphenyl group, a naphthyl group or the like.
  • the monomer is preferably 1,3,6-naphthalenetrisulfonyl chloride in the present invention.
  • the method for preparing a polysulfonamide nanofiltration or reverse osmosis composite membrane wherein the polyamine can be ethylenediamine, triethylenetetraamine (NH2CH2CH2NHCH2CH2NHCH2CH2NH2), meta-xylylenediamine or other multifunctional group of primary amines, a secondary amine; piperazine, or 2,5-dimethylpiperazine, or N,N'-diaminopiperazine, or other reactive piperazine-containing derivative, or a mixture thereof, preferably piperazine of the invention .
  • the polyamine can be ethylenediamine, triethylenetetraamine (NH2CH2CH2NHCH2CH2NHCH2CH2NH2), meta-xylylenediamine or other multifunctional group of primary amines, a secondary amine; piperazine, or 2,5-dimethylpiperazine, or N,N'-diaminopiperazine, or other reactive piperazine-containing derivative, or a mixture
  • the solvent of the polyamine solution may be water or an organic solvent or a mixed solvent thereof, and an organic solvent such as acetone, methanol, ethanol, isopropanol or the like, the present invention Water is preferred as the polyamine solvent.
  • the solvent of the sulfonyl chloride solution may be ethyl acetate, chloroform, toluene, xylene, Isopar series, n-hexane, heptane or n-dodecane or a mixed solvent of the above.
  • the polyamine solution contains 0.0% to 5% of a catalyst or an acid absorbent.
  • the catalyst or acid absorbent of the present invention is triethylamine, or sodium hydroxide, or sodium carbonate, and the like, and triethylamine is preferred in the present invention.
  • the polyamine solution contains 0.0%-10% of a porogen, such as camphorsulfonic acid and its triethylamine salt or the like. The same effect of the substance and so on.
  • nanoparticles are added to the polyamine monomer solution or the sulfonyl chloride monomer solution, and the nanoparticles are characterized by pores or nonporous, cyclic or acyclic. Inorganic or organic nanoscale particles.
  • a surfactant is added to the polyamine monomer solution or the sulfonyl chloride monomer solution, and the surfactant concentration range of the present invention is preferentially selected. It is from 0.0% to 2%.
  • the invention provides a polysulfonamide nanofiltration or reverse osmosis composite membrane method, wherein the surfactant comprises an anionic surfactant such as sodium dodecyl sulfate; a cationic surfactant such as a quaternary ammonium compound; zwitterionic surface active Agents such as lecithin, amino acid type and betaine type; nonionic surfactants such as fatty acid glycerides, polysorbates, etc.; polyoxyethylene type surfactants such as long chain fatty acid esters, fatty alcohol esters, phosphate esters Wait.
  • anionic surfactant such as sodium dodecyl sulfate
  • a cationic surfactant such as a quaternary ammonium compound
  • zwitterionic surface active Agents such as lecithin, amino acid type and betaine type
  • nonionic surfactants such as fatty acid glycerides, polysorbates, etc.
  • polyoxyethylene type surfactants such as long
  • the present invention also requires a polysulfonamide nanofiltration or reverse osmosis composite membrane prepared by the molecular layer assembly method.
  • the polysulfonamide nanofiltration or reverse osmosis composite membrane prepared by the invention is characterized in that the removal rate of the salt such as magnesium sulfate, calcium chloride and sodium chloride or the organic matter having a molecular weight of less than 1000 g/moL can be up to 99% or above.
  • the salt such as magnesium sulfate, calcium chloride and sodium chloride or the organic matter having a molecular weight of less than 1000 g/moL can be up to 99% or above.
  • the invention discloses a method for assembling a polysulfonamide composite membrane molecular layer layer, which is characterized in that a polysulfonamide composite membrane having different removal rates and different water flux properties can be prepared by adjusting the number of assembled layers.
  • the method for preparing a polysulfonamide composite membrane molecular layer layer according to the invention is characterized in that the surface roughness of the prepared polysulfonamide nanofiltration or reverse osmosis membrane is much lower than the surface of the polysulfonamide nanofiltration or reverse osmosis membrane prepared by the interfacial polymerization technique. Roughness.
  • the polysulfonamide structure to which the present invention relates is applicable to the polysulfonamide or modified polysulfonamide structures mentioned in the patents US Pat. No. 6,837,996 and US Pat.
  • the molecular layer assembly technique to which the present invention relates is a reference in Science 2003, 301, 818-821, J. Mater. Chem. 2007, 17, 664-669, Macromolecules, 2010, 43, 9056-9062 and the like. It is intended that two different monomers have mutual reactive groups. When the two monomers are in contact, the layers are assembled under certain conditions to form a crosslinked structure by covalent bonding.
  • the porogen mentioned in the present invention refers to a small molecule substance which is added during the film forming process, does not chemically react with the monomer, and is easily eluted to promote pore formation on the surface of the film.
  • the molecular layer assembly involved in the present invention means that two or more reactive monomers are adsorbed on the surface of the porous support film by alternate soaking, spraying, and spin coating, and the same layer of monomers, layers and layers are generated. The process of assembly cross-linking between the reactions.
  • the spray film formation of the present invention refers to a process in which a monomer compression solution can be atomized and sprayed on a surface of a film by a gas compression machine or a vessel and subjected to a certain condition to form a crosslinked film.
  • the spin coating film of the present invention refers to the principle of centrifugal rotation of a tray, placing the porous supporting film in the center of the tray of the homogenizer, dropping the monomer solution, and immersing for a certain time to set a certain rotation speed to screw out most of the liquid.
  • a thin layer of monomer liquid layer is uniformly spread on the surface of the film.
  • a process of forming a multi-layered monomer liquid layer on the surface of the film by alternately adding a monomer, and crosslinking the film formation after a certain condition.
  • the monolayer molecular layer assembly polysulfonamide composite membrane of the invention is defined as: the surface of the porous support membrane is treated by polyamine and sulfonyl chloride respectively to form a selective polysulfonamide functional layer, which is a single layer polysulfonamide nanofiltration. Or reverse osmosis composite membrane.
  • the addition concentration of the monomer, the acid absorbent, the catalyst and the nano particle of the invention is a mass percentage concentration, and the concentration of each substance added according to the invention can be used to prepare a polysulfonamide nanofiltration or reverse osmosis composite membrane by the technique of the invention. .
  • test conditions for the desalting performance of the polysulfonamide nanofiltration or reverse osmosis composite membrane prepared by the invention are the salt solution concentration of 2000 mg/L, the test pressure is 1.5 MPa, the system control temperature is 25 ° C, the cross flow operation mode test, the raw water flow control At 6-7 LPM.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Water Supply & Treatment (AREA)
  • Nanotechnology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Environmental & Geological Engineering (AREA)
  • Organic Chemistry (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)

Abstract

L'invention concerne un procédé de préparation d'une membrane composite de nanofiltration au polysulfonamide ou d'osmose inverse, comprenant les étapes suivantes : une membrane de support poreuse est soumise à un assemblage de couche moléculaire dans une solution monomère de chlorure de sulfonyle et de polyamine, suivi d'un traitement thermique à une température comprise entre 40 °C et 110 °C, et enfin, par lavage complet avec une solution aqueuse d'éthanol. La membrane composite de polysulfonamide ainsi préparée est particulièrement appropriée pour le traitement de fluides acides ou alcalins.
PCT/CN2016/087981 2016-06-30 2016-06-30 Procédé de préparation d'une membrane composite de nanofiltration au polysulfonamide ou d'osmose inverse par assemblage de couches moléculaires WO2018000361A1 (fr)

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PCT/CN2016/087981 WO2018000361A1 (fr) 2016-06-30 2016-06-30 Procédé de préparation d'une membrane composite de nanofiltration au polysulfonamide ou d'osmose inverse par assemblage de couches moléculaires
CN201680003641.XA CN106999870A (zh) 2016-06-30 2016-06-30 聚磺酰胺纳滤或反渗透复合膜的分子层层组装制备方法

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CN113680210A (zh) * 2021-08-17 2021-11-23 安徽智泓净化科技股份有限公司 低价离子分离用纳滤膜及其制备方法
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CN109126463B (zh) * 2018-08-02 2021-08-06 中国石油大学(华东) 一种含微孔中间层高通量纳滤膜的制备方法
CN109364759A (zh) * 2018-12-21 2019-02-22 滁州学院 一种木质素磺酸钙耐溶剂复合纳滤膜及其制备方法
CN109833778A (zh) * 2018-12-26 2019-06-04 天津膜天膜科技股份有限公司 提高连续化生产外压型中空纤维纳滤膜截留率的方法
CN110052170B (zh) * 2019-05-09 2021-10-22 万华化学集团股份有限公司 一种耐酸碱清洗的反渗透膜及其制备方法和应用
CN112316752B (zh) * 2020-11-04 2022-04-12 天津工业大学 一种磺胺类小分子表面改性聚酰胺复合膜及其制备方法
CN112717712B (zh) * 2020-12-15 2022-02-25 中国科学院过程工程研究所 一种耐酸型纳滤膜及其制备方法和应用
CN114642972B (zh) * 2020-12-18 2023-06-13 沃顿科技股份有限公司 脱硼反渗透膜及其制备方法

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