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CN106345308B - A kind of preparation method of polyester amide composite nanofiltration membrane with strong chlorine resistance and anti-pollution - Google Patents

A kind of preparation method of polyester amide composite nanofiltration membrane with strong chlorine resistance and anti-pollution Download PDF

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CN106345308B
CN106345308B CN201610892897.2A CN201610892897A CN106345308B CN 106345308 B CN106345308 B CN 106345308B CN 201610892897 A CN201610892897 A CN 201610892897A CN 106345308 B CN106345308 B CN 106345308B
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preparation
strong
membrane
chlorine resistance
polyester amide
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CN106345308A (en
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于水利
张瑞君
时文歆
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Harbin Institute of Technology Shenzhen
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Harbin Institute of Technology Shenzhen
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    • 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
    • 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
    • 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

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

Abstract

The preparation method of strong and resistant to pollution polyesteramide composite nanometer filtering film the invention discloses a kind of chlorine resistance; the method is using serinol as aqueous phase reactions monomer; water phase is added as phase transfer catalyst and acylation catalyst in 4-dimethylaminopyridine simultaneously, new polyester amide composite nanometer filtering film is prepared by serinol and interface polymerization reaction of the polynary acyl chlorides on porous support layer.The present invention is by serinol and polynary acyl chlorides in carrying out interface polymerization reaction on porous support layer under the catalytic action of 4-dimethylaminopyridine, to obtain a kind of novel polyesteramide composite nanometer filtering film, the nanofiltration membrane has the characteristics that chlorine resistance is good, hydrophily is strong, contamination resistance is strong and solute retention ability is strong, and preparation process is easy to be mild, is suitable for industrialized production.

Description

A kind of chlorine resistance is strong and the preparation method of resistant to pollution polyesteramide composite nanometer filtering film
Technical field
The invention belongs to technical field of membrane separation, and it is compound to be related to the polyesteramide that a kind of chlorine resistance is strong, contamination resistance is strong The preparation method of nanofiltration membrane.
Background technique
With the development of economy, the aggravation of the increase of population and water pollution, the world is multinational to be faced with shortage of water resources Problem.Therefore, in the case where extra clean water resource can not supplement, carrying out purified treatment to existing water resource is reply water The important measure of crisis of resource.Nanofiltration membrane (NF) is a kind of special membrane material between ultrafiltration membrane and reverse osmosis membrane, its energy Small organic molecule is enough retained, there is partially desalted ability, while having the characteristics that flux is high, low energy consumption, has been applied at present In the softening of water, bitter desalination, advanced treatment of wastewater, drug and the various fields such as biology purification and food processing.
The polyamide composite nanofiltration membrane prepared on supporting layer by interface polymerization reaction by polyamine and polynary acyl chlorides Leading position has been occupied in the market share of nanofiltration membrane at present.However, more serious membrane pollution problem and chlorine resistance Difference is to limit the major obstacle of its further genralrlization application.Therefore, exploitation has contamination resistance and the strong Performances of Novel Nano-Porous of chlorine resistance Filter membrane is the focus of numerous researchers.It is existing studies have shown that the polyamide prepared by polyamine and polynary acyl chlorides is compound Nanofiltration membrane contaminant removal capacity usually with higher and desalting ability, but its contamination resistance and chlorine resistance are poor；And by Crosslinked hyperbranched polyalcohol composite nano filter membrance prepared by polyphenol or polyalcohol and polynary acyl chlorides or polyacid usually has stronger contamination resistance And chlorine resistance, but its fenestra is larger, and pollutant interception capacity and salt rejection rate are lower.How by polyamide nanofiltration membrane and polyester nanofiltration The advantages of film, combines, to prepare the composite nanometer filter that a kind of contamination resistance is strong, chlorine resistance is strong and contaminant removal capacity is strong Film is our goal in research.
Summary of the invention
The preparation of strong and resistant to pollution polyesteramide composite nanometer filtering film the object of the present invention is to provide a kind of novel chlorine resistance Method combines the advantages of polyamide nanofiltration membrane and polyester nanofiltration membrane, solves that existing commercial nanofiltration membrane is easy to pollute, chlorine resistance The problem of difference.
The purpose of the present invention is what is be achieved through the following technical solutions:
A kind of chlorine resistance is strong and the preparation method of resistant to pollution polyesteramide composite nanometer filtering film, using serinol as aqueous phase reactions Monomer, at the same using 4-dimethylaminopyridine be added water phase be used as phase transfer catalyst and acylation catalyst, by serinol with it is more Interface polymerization reaction of first acyl chlorides on porous support layer prepares new polyester amide composite nanometer filtering film, the specific steps are as follows:
One, prepare aqueous phase solution: into pure water be added 0.5 ~ 5%(w/v) serinol, while be added 0.05 ~ 0.5%(w/ V) 4-dimethylaminopyridine uses triethylamine by the pH of solution as phase transfer and acylation catalyst after being sufficiently stirred and dissolving Value is adjusted to 11.3 ~ 12.0；
Two, it prepares organic phase solution: with one of n-hexane, hexamethylene, toluene, normal heptane or normal octane or a variety of being Organic solvent, into organic solvent be added 0.01 ~ 0.5%(w/v) polynary acyl chlorides；
Three, using polysulfones, polyether sulfone, sulfonated polyether sulfone or the porous ultrafiltration membrane of polypropylene as supporting course, first by aqueous phase solution It swings to support layer surface and impregnates 1 ~ 10 minute, then outwell aqueous phase solution and remove film surface excessive moisture, then by organic phase Solution swings to film surface, and reacts 10 ~ 120 seconds, and organic solvent is used sufficiently rinse to remove not to film surface after reaction Reaction monomers；
Four, film of the organic solvent after flushed is placed at 20 ~ 80 DEG C and is heat-treated 5 ~ 20 minutes；
Five, finally film is sufficiently cleaned with pure water, thus to obtain polyesteramide composite nanometer filtering film.
The present invention is by serinol and polynary acyl chlorides on porous support layer under the catalytic action of 4-dimethylaminopyridine Interface polymerization reaction is carried out, to obtain a kind of novel polyesteramide composite nanometer filtering film, which has chlorine resistance good, close Aqueous feature strong, contamination resistance is strong and solute retention ability is strong, and preparation process is easy to be mild, is suitable for industrialized production.
Detailed description of the invention
Fig. 1 is serinol molecular structural formula；
Fig. 2 is new polyester amide composite nanometer filtering film atomic force microscope pattern；
Fig. 3 is new polyester amide composite nanometer filtering film scanning electron microscope pattern；
Fig. 4 is new polyester amide composite nanometer filtering film infrared spectroscopy.
Specific embodiment
Further description of the technical solution of the present invention with reference to the accompanying drawing, and however, it is not limited to this, all to this Inventive technique scheme is modified or replaced equivalently, and without departing from the spirit and scope of the technical solution of the present invention, should all be covered Within the protection scope of the present invention.
Specific embodiment 1: the strong and resistant to pollution polyesteramide composite nanometer filter present embodiments provide for a kind of chlorine resistance The preparation method of film, the specific steps are as follows:
One, prepare aqueous phase solution: 2%(w/v is added into pure water) serinol (its structural formula is as shown in Figure 1), simultaneously plus Enter 0.2%(w/v) 4-dimethylaminopyridine as phase transfer and acylation catalyst, after being sufficiently stirred and dissolving use triethylamine The pH value of solution is adjusted to 11.5；
Two, prepare organic phase solution: using n-hexane as organic solvent, 0.1%(w/v is added into organic solvent) it is polynary Acyl chlorides；
Three, using the porous ultrafiltration membrane of polyether sulfone as supporting course, aqueous phase solution is swung into support layer surface first and impregnates 2 points Then clock outwells aqueous phase solution and removes film surface excessive moisture, organic phase solution is then swung to film surface, and reaction 60 seconds, instead Organic solvent is used sufficiently rinse to remove unreacted monomer to film surface after answering；
Four, film of the organic solvent after flushed is placed at 50 DEG C and is heat-treated 10 minutes；
Five, finally film is sufficiently cleaned with pure water, thus to obtain polyesteramide composite nanometer filtering film.
Fig. 2A gives the porous support layers atomic force microscope shape appearance figure not reacted, and it is poly- that Fig. 2 B then gives interface Obtained polyesteramide composite nanometer filtering film shape appearance figure after the completion of closing, as shown in Figure 2, by the above reaction step, successfully compared with To form concavo-convex polyesteramide active layer on smooth supporting course.
Fig. 3 A and B are respectively the scanning electron microscope shape appearance figure of porous support layers and polyesteramide composite nanometer filtering film, and two The comparison of person equally confirms the generation of polyesteramide active layer.It is received in addition, Fig. 3 B also clearly illustrates that the polyesteramide is compound Filter membrane surface has the shape characteristic similar to particle packing, this is significantly different with traditional polyamide composite nanofiltration membrane.
Fig. 4 then confirms the generation of ester bond and amido bond after reaction using the angle of infrared spectroscopy chemically key, thus into One step confirms the generation of polyesteramide active layer.
Specific embodiment 2: the strong and resistant to pollution polyesteramide composite nanometer filter present embodiments provide for a kind of chlorine resistance The preparation method of film, the specific steps are as follows:
One, prepare aqueous phase solution: 1%(w/v is added into pure water) serinol (its structural formula is as shown in Figure 1), simultaneously plus Enter 0.2%(w/v) 4-dimethylaminopyridine as phase transfer and acylation catalyst, after being sufficiently stirred and dissolving use triethylamine The pH value of solution is adjusted to 11.5；
Two, prepare organic phase solution: using normal octane as organic solvent, 0.05%(w/v is added into organic solvent) it is polynary Acyl chlorides；
Three, using polysulfone porous ultrafiltration membrane as supporting course, aqueous phase solution is swung into support layer surface first and is impregnated 2 minutes, Then it outwells aqueous phase solution and removes film surface excessive moisture, organic phase solution is then swung into film surface, and react 50 seconds, reaction knot Organic solvent is used sufficiently rinse to remove unreacted monomer to film surface after beam；
Four, film of the organic solvent after flushed is placed at 60 DEG C and is heat-treated 15 minutes；
Five, finally film is sufficiently cleaned with pure water, thus to obtain polyesteramide composite nanometer filtering film.
Specific embodiment 3: the strong and resistant to pollution polyesteramide composite nanometer filter present embodiments provide for a kind of chlorine resistance The preparation method of film, the specific steps are as follows:
One, prepare aqueous phase solution: 0.5%(w/v is added into pure water) serinol (its structural formula is as shown in Figure 1), simultaneously 0.05%(w/v is added) 4-dimethylaminopyridine as phase transfer and acylation catalyst, using three second after being sufficiently stirred and dissolving The pH value of solution is adjusted to 11.5 by amine；
Two, prepare organic phase solution: using toluene and hexamethylene as organic solvent, the two volume ratio is 1:1, to organic solvent Middle addition 0.05%(w/v) polynary acyl chlorides；
Three, using the porous ultrafiltration membrane of polypropylene as supporting course, aqueous phase solution is swung into support layer surface first and impregnates 4 points Then clock outwells aqueous phase solution and removes film surface excessive moisture, organic phase solution is then swung to film surface, and reaction 70 seconds, instead Organic solvent is used sufficiently rinse to remove unreacted monomer to film surface after answering；
Four, film of the organic solvent after flushed is placed at 70 DEG C and is heat-treated 15 minutes；
Five, finally film is sufficiently cleaned with pure water, thus to obtain polyesteramide composite nanometer filtering film.
Specific embodiment 4: the strong and resistant to pollution polyesteramide composite nanometer filter present embodiments provide for a kind of chlorine resistance The preparation method of film, the specific steps are as follows:
One, prepare aqueous phase solution: 1.5%(w/v is added into pure water) serinol (its structural formula is as shown in Figure 1), simultaneously 0.15%(w/v is added) 4-dimethylaminopyridine as phase transfer and acylation catalyst, using three second after being sufficiently stirred and dissolving The pH value of solution is adjusted to 11.5 by amine；
Two, prepare organic phase solution: using normal octane as organic solvent, 0.07%(w/v is added into organic solvent) it is polynary Acyl chlorides；
Three, using the porous ultrafiltration membrane of sulfonated polyether sulfone as supporting course, aqueous phase solution is swung into support layer surface first and impregnates 3 Minute, it then outwells aqueous phase solution and removes film surface excessive moisture, organic phase solution is then swung into film surface, and react 60 seconds, Organic solvent is used sufficiently rinse to remove unreacted monomer to film surface after reaction；
Four, film of the organic solvent after flushed is placed at 80 DEG C and is heat-treated 15 minutes；
Five, finally film is sufficiently cleaned with pure water, thus to obtain polyesteramide composite nanometer filtering film.

Claims (5)

1.一种耐氯性强且抗污染的聚酯酰胺复合纳滤膜的制备方法，其特征在于所述方法步骤如下：1. a kind of preparation method of the polyester amide composite nanofiltration membrane that chlorine resistance is strong and anti-pollution, it is characterized in that described method steps are as follows: 一、配制水相溶液：向纯水中加入0.5~5%（w/v）的丝氨醇，同时加入0.05~0.5%（w/v）的4-二甲氨基吡啶，充分搅拌并溶解后将溶液的pH值调至11.3~12.0；1. Preparation of aqueous solution: add 0.5~5% (w/v) serinol to pure water, and at the same time add 0.05~0.5% (w/v) 4-dimethylaminopyridine, stir well and dissolve Adjust the pH of the solution to 11.3~12.0; 二、配制有机相溶液：向有机溶剂中加入0.01~0.5%（w/v）的多元酰氯；2. Preparation of organic phase solution: add 0.01~0.5% (w/v) polybasic acid chloride to the organic solvent; 三、首先将水相溶液倒向支撑层表面并浸泡1~10 分钟，然后倒掉水相溶液并除去膜面多余水分，接着将有机相溶液倒向膜面，并反应10~120 秒，反应结束后采用有机溶剂对膜面进行充分冲洗；3. First pour the aqueous phase solution onto the surface of the support layer and soak for 1~10 minutes, then pour the aqueous phase solution and remove excess water on the membrane surface, then pour the organic phase solution onto the membrane surface, and react for 10~120 seconds, the reaction After the end, use organic solvent to fully rinse the membrane surface; 四、将有机溶剂冲洗过后的膜进行热处理；4. Heat treatment of the membrane after rinsing with the organic solvent; 五、最后用纯水对热处理过的膜进行充分清洗，由此获得聚酯酰胺复合纳滤膜。5. Finally, fully wash the heat-treated membrane with pure water, thereby obtaining a polyester amide composite nanofiltration membrane. 2.根据权利要求1所述的耐氯性强且抗污染的聚酯酰胺复合纳滤膜的制备方法，其特征在于所述步骤一中采用三乙胺将溶液的pH值调至11.3~12.0。2. the preparation method of the polyester amide composite nanofiltration membrane with strong chlorine resistance and anti-pollution according to claim 1, is characterized in that in described step 1, adopts triethylamine to adjust the pH value of solution to 11.3～12.0 . 3.根据权利要求1所述的耐氯性强且抗污染的聚酯酰胺复合纳滤膜的制备方法，其特征在于所述有机溶剂为正己烷、环己烷、甲苯、正庚烷或正辛烷中的一种或多种。3. The preparation method of the polyester amide composite nanofiltration membrane with strong chlorine resistance and anti-pollution according to claim 1, wherein the organic solvent is n-hexane, cyclohexane, toluene, n-heptane or n-heptane one or more of octane. 4.根据权利要求1所述的耐氯性强且抗污染的聚酯酰胺复合纳滤膜的制备方法，其特征在于所述支撑 层为聚砜、聚醚砜、磺化聚醚砜或聚丙烯多孔超滤膜。4. The preparation method of polyester amide composite nanofiltration membrane with strong chlorine resistance and anti-pollution according to claim 1, characterized in that the support layer is polysulfone, polyethersulfone, sulfonated polyethersulfone or polyethersulfone Propylene porous ultrafiltration membrane. 5.根据权利要求1所述的耐氯性强且抗污染的聚酯酰胺复合纳滤膜的制备方法，其特征在于所述热处理温度为20~80℃，时间为5~20分钟。5. The preparation method of the polyester amide composite nanofiltration membrane with strong chlorine resistance and anti-pollution according to claim 1, characterized in that the heat treatment temperature is 20-80°C, and the time is 5-20 minutes.
CN201610892897.2A 2016-10-13 2016-10-13 A kind of preparation method of polyester amide composite nanofiltration membrane with strong chlorine resistance and anti-pollution Active CN106345308B (en)

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CN115869784B (en) * 2022-12-21 2024-09-24 中国科学院过程工程研究所 Composite nanofiltration membrane based on primary layer solvent rearrangement and catalytic activation and preparation method and application thereof

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CN102500244A (en) * 2011-11-30 2012-06-20 杭州水处理技术研究开发中心有限公司 Preparation method of reverse osmosis composite membrane for sea water desalinization
CN102698620A (en) * 2012-06-12 2012-10-03 浙江大学 Method for preparing reverse osmosis composite membrane by taking hyperbranched polymer as monomer
WO2013176524A1 (en) * 2012-05-24 2013-11-28 주식회사 엘지화학 Reverse osmosis membrane
CN103477227A (en) * 2011-03-28 2013-12-25 3M创新有限公司 Ligand functional substrates
CN104667759A (en) * 2013-11-29 2015-06-03 贵阳时代沃顿科技有限公司 Preparation method of high-throughput anti-pollution composite nanofiltration membrane
CN105983348A (en) * 2015-03-06 2016-10-05 南京理工大学 Preparation method for polyesteramide composite nanofiltration membrane

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103477227A (en) * 2011-03-28 2013-12-25 3M创新有限公司 Ligand functional substrates
CN102500244A (en) * 2011-11-30 2012-06-20 杭州水处理技术研究开发中心有限公司 Preparation method of reverse osmosis composite membrane for sea water desalinization
WO2013176524A1 (en) * 2012-05-24 2013-11-28 주식회사 엘지화학 Reverse osmosis membrane
CN102698620A (en) * 2012-06-12 2012-10-03 浙江大学 Method for preparing reverse osmosis composite membrane by taking hyperbranched polymer as monomer
CN104667759A (en) * 2013-11-29 2015-06-03 贵阳时代沃顿科技有限公司 Preparation method of high-throughput anti-pollution composite nanofiltration membrane
CN105983348A (en) * 2015-03-06 2016-10-05 南京理工大学 Preparation method for polyesteramide composite nanofiltration membrane

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