CN108636135A - A kind of modified cellulose filter membrane and preparation method thereof - Google Patents
A kind of modified cellulose filter membrane and preparation method thereof Download PDFInfo
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- CN108636135A CN108636135A CN201810337225.4A CN201810337225A CN108636135A CN 108636135 A CN108636135 A CN 108636135A CN 201810337225 A CN201810337225 A CN 201810337225A CN 108636135 A CN108636135 A CN 108636135A
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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
- B01D71/08—Polysaccharides
- B01D71/10—Cellulose; Modified cellulose
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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
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- 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
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/286—Treatment of water, waste water, or sewage by sorption using natural organic sorbents or derivatives thereof
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
- C08J7/16—Chemical modification with polymerisable compounds
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
- C02F2101/20—Heavy metals or heavy metal compounds
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/16—Nature of the water, waste water, sewage or sludge to be treated from metallurgical processes, i.e. from the production, refining or treatment of metals, e.g. galvanic wastes
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/26—Nature of the water, waste water, sewage or sludge to be treated from the processing of plants or parts thereof
- C02F2103/28—Nature of the water, waste water, sewage or sludge to be treated from the processing of plants or parts thereof from the paper or cellulose industry
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
- C08J2301/02—Cellulose; Modified cellulose
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Abstract
The present invention provides a kind of modified cellulose filter membranes and preparation method thereof, are reacted with cellophane with 2 bromine isobutyl acylbromides, obtain cellulose base macromole evocating agent；By cellulose base macromole evocating agent in cuprous bromide and N, N, N', N, ' under the effect of N " five methyl diethylentriamines, carry out ATRP polymerization with anionic monomer, obtain modified cellulose filter membrane.Modified cellulose filter membrane has adsorption filtration heavy metal ion performance, has extremely strong stability, can Reusability, can be used for being electroplated, metallurgy, papermaking, the Industrial Waste Water Treatments such as printing and dyeing.
Description
【Technical field】
Present invention relates particularly to a kind of modified cellulose filter membranes and preparation method thereof.
【Background technology】
With the production-scale expansion of domestic and international all trades and professions, water consumption and wastewater flow rate increase, and effect on environment is very big, dirty
Water process becomes the problem of all multiple enterprises.The especially factories such as plating, metallurgy, dyeing and finishing, production waste water be discharged contain very much
Heavy metal contaminants bring prodigious influence to environment and human health.It administers the cumbersome of effluent containing heavy metal ions, take
With high, and the method for conventionally employed flocculation sediment is ineffective, and be easy to cause secondary pollution.Therefore, developing can weigh
What is utilized again has the film of absorption heavy metal ion performance, has important practical significance.
Cellulose has as natural macromolecular material the abundantest in nature and derives from a wealth of sources, is cheap, is raw
The advantages that object compatibility is good, mechanical property is good.Therefore functional modification can be carried out by chemically or physically method appropriate, prepared
Go out cellulose base functional material.(Y.Habibi.Chem.Soc.Rev.2014,43,1519-1542)
2- acrylamide-2-methyl propane sulfonics (AMPS) are a kind of widely used water-soluble sulfonic acids type anion lists
Body, tool there are one unsaturated double-bond, can homopolymerization or copolymerization form anionic polymer, have with cationic substance relatively strong
Electrostatic interaction, to effectively adsorb heavy metal ion substance.(Matthew G.Kellum.；Adam E.Smith.；
Stacey Kirkland York.et al.Macromoleculars.2010,43,7033-7040) simultaneously, with negative electricity
The advantages that density value of lotus is big, efficient and safety, relative molecular mass are easy to control.But its is soluble easily in water, easily with water
It is lost in, causes not reusing.
【Invention content】
One of the technical problem to be solved in the present invention is to provide a kind of preparation method of modified cellulose filter membrane.
The invention is realized in this way：A kind of preparation method of modified cellulose filter membrane, includes the following steps：
(1) cellophane is immersed in dichloromethane, chloroform, toluene or dimethylbenzene, pyridine is added dropwise and 2- bromines are different
Cellulose base macromole evocating agent is obtained by the reaction in butyryl bromide；Wherein, the amount of substance compares pyridine：2- bromine isobutyl acylbromides：Cellulose is thin
Film=0.3-3：0.3-3：1；
(2) cellulose base macromole evocating agent is placed in aqueous solution, catalyst cuprous bromide, ligand N, N, N' is added,
N, ' N "-five methyl diethylentriamine and anionic monomer, deoxygenation operation is carried out, is then reacted at 50 DEG C for 24 hours, cleaning is dry
After dry, modified cellulose filter membrane is obtained；Wherein, the amount ratio of the substance of cuprous bromide and cellophane is 0.05-1：1；N,N,
N', N, ' the amount ratio 0.8-2 of the substance of N "-five methyl diethylentriamine and cuprous bromide：1.
Preferably, in described (2), the amount ratio of the substance of anionic monomer and cellophane is 0.5-10：1.
Preferably, the amount ratio of the substance of the anionic monomer and cellophane is 2.0-8：1.
Preferably, the anionic monomer is 2- acrylamide-2-methyl propane sulfonics.
Preferably, the thickness of the modified cellulose filter membrane is 0.1-1000 μm.
The second technical problem to be solved by the present invention is to provide a kind of modified cellulose filter membrane.
The invention is realized in this way：A kind of modified cellulose filter membrane, molecular structural formula is such as：
Wherein, n=5~40.
Preferably, the thickness of the modified cellulose filter membrane is 0.1-1000 μm.
The advantage of the invention is that：Using cellophane as matrix, interface is carried out using anionic monomer and is connect
Branch is modified, assigns the performance that cellophane has adsorption filtration heavy metal ion, can be used for being electroplated, metallurgy, papermaking, printing and dyeing etc.
Industrial Waste Water Treatments.
【Description of the drawings】
Fig. 1 is the synthetic route schematic diagram of modified cellulose filter membrane in the present invention.
Fig. 2 is the IR spectrograms of modified cellulose filter membrane in the present invention.
Fig. 3 is the regeneration times of modified cellulose filter membrane in the present invention to Cu2+The relational graph of removal rate.
【Specific implementation mode】
Below in conjunction with specific implementation mode, the present invention is further illustrated.
Embodiment 1
(1) by weight be 82mg cellophane (Hangzhou Special Paper Industry Co., Ltd., content of cellulose are
0.5mmol), be placed in fill 15mL dichloromethane from container.By 1.5mmol pyridines, 1.5mmol 2- bromine isobutyl acylbromides
It instills dropwise wherein.After reacting for 24 hours at normal temperatures, washing, obtaining surface grafting has macromole evocating agent point cellophane, i.e.,
Cellulose base macromole evocating agent.
(2) cellulose base macromole evocating agent is added in 15mL deionized waters, 5.0mmol 2- acrylamides-is added
2- methyl propane sulfonic acids (sodium) monomer (is reacted with sodium hydroxide by 2- acrylamide-2-methyl propane sulfonics and is made), 1.0mmol N,
N, N', N, ' N "-five methyl diethylentriamine, 0.5mmol cuprous bromides.After being reacted 1 day at 50 DEG C, wash, it is dry, it obtains
Adsorb the modified cellulose filter membrane of heavy metal ion.
Embodiment 2
(1) by by weight be 82mg cellophane (Hangzhou Special Paper Industry Co., Ltd., content of cellulose are
0.5mmol), be placed in fill 15mL dimethylbenzene from container.By 0.15mmol pyridines, 0.15mmol 2- bromine isobutyl acylbromides
It instills dropwise wherein.After reacting for 24 hours at normal temperatures, washing, cellulose base macromole evocating agent.
(2) cellulose base macromole evocating agent is added in 15mL deionized waters, 0.25mmol 2- acryloyls is added
Amine -2- methyl propane sulfonic acids (sodium) monomer (is reacted with sodium hydroxide by 2- acrylamide-2-methyl propane sulfonics and is made), 0.02mmol
N, N, N', N, ' N "-five methyl diethylentriamine, 0.025mmol cuprous bromides.After being reacted 1 day at 50 DEG C, wash, it is dry,
Obtain the modified cellulose filter membrane of absorption heavy metal ion.
Embodiment 3
(1) by weight be 82mg cellophane (Hangzhou Special Paper Industry Co., Ltd., content of cellulose are
0.5mmol), be placed in fill 15mL chloroforms from container, by 0.5mmol pyridines, 0.5mmol 2- bromine isobutyl acylbromides
It instills dropwise wherein, after reacting for 24 hours at normal temperatures, washing obtains cellulose base macromole evocating agent.
(2) cellulose base macromole evocating agent is added in 15mL deionized waters, 4.0mmol 2- acrylamides-is added
2- methyl propane sulfonic acids (sodium) monomer (is reacted with sodium hydroxide by 2- acrylamide-2-methyl propane sulfonics and is made), 0.15mmol N,
N, N', N, ' N "-five methyl diethylentriamine, 0.1mmol cuprous bromides.After being reacted 1 day at 50 DEG C, wash, it is dry, it obtains
Adsorb the modified cellulose filter membrane of heavy metal ion.
Embodiment 4
This part difference from Example 3 is：
(2) 1.0mmol 2- acrylamide-2-methyl propane sulfonics (sodium) monomer is added (by 2- acrylamide -2- methyl-props
Sulfonic acid is reacted with sodium hydroxide to be made)
Modified cellulose filter membrane produced by the present invention has adsorption filtration heavy metal ion performance, and ATRP method building-up process is such as
Shown in Fig. 1, IR Characterization is carried out to the structure of the film, as shown in Fig. 2, as shown in Figure 2, anionic monomer is with chemical bond form
Graft copolymerization is tested adsorption filtration heavy metal ion performance and its repeat performance on cellulose surface,
As shown in Figure 3.
The modified cellulose filter membrane of any absorption heavy metal ion obtained in 1-4 of the embodiment of the present invention adsorbed
Heavy metal ion test is filtered, test solution is attached most importance to Metal Ions Cd2+Solution.
It takes 1 modified cellulose filter membrane to be placed in self-control filter device, 1mg/L Cd is added2+Solution carries out natural filtration；
Filtrate is collected, and dense to heavy metal ion in filtrate using atomic absorption spectrophotometry (GB7475-87) (HJ485-2009)
Degree is tested.Meanwhile 1 unmodified cellulose film being taken to be parallel contrast experiment.After modified cellulose filter membrane filtering,
Heavy metal ion Cd in filtrate2+Concentration reduces, and illustrates that film has good adsorption filtration heavy metal ion performance.And through not changing
Property cellophane filtering, heavy metal ion Cd2+Solution passes through film, film counterweight Metal Ions Cd2+Solution absorbs and filter
Performance is extremely low.
Meanwhile the repeat performance of modified cellulose filter membrane is tested, by modified cellulose filter membrane NaCl
After solution regeneration, modified cellulose filter membrane is after 10 times or more repeat, counterweight Metal Ions Cd2+The removal rate of solution still exists
90% or more.
Any modified cellulose filter membrane obtained in 1-4 of the embodiment of the present invention is carried out adsorption filtration heavy metal ion to survey
Examination.Test solution is heavy metal ion Cu2+Solution.
It takes the modified cellulose filter membrane of 1 absorption heavy metal ion to be placed in self-control filter device, 10mg/L Cu is added2+
Solution carries out natural filtration.Filtrate is collected, and dense to heavy metal ion in filtrate using spectrophotometry (HJ485-2009)
Degree is tested.Meanwhile 1 unmodified cellulose film being taken to be parallel contrast experiment.After modified cellulose filter membrane filtering,
Heavy metal ion Cu in filtrate2+Concentration reduces.This illustrates that film has good adsorption filtration heavy metal ion performance.And through not
Modified cellophane filtering, heavy metal ion Cu2+Solution is by film, and film is to heavy metal ion Cu2+Solution adsorbed
It is extremely low to filter performance.
After the modified cellulose filter membrane for adsorbing heavy metal ion is regenerated with NaCl solution, its repeat performance is investigated,
Modified cellulose filter membrane is after 10 times or more repeat, to heavy metal ion Cu2+The removal rate of solution is still 90% or more, such as
Shown in Fig. 3.
In summary, the present invention carries out graft modification, obtained modified fibre using anionic monomer to cellophane
Plain filter membrane has adsorption filtration heavy metal ion performance, can heavy metal ion be carried out effectively catching.The present invention uses ATRP method
By anionic monomer, graft copolymerization makes cellulose base filter membrane have extremely strong stabilization on cellulose side chain in the form of covalent bond
Property, can Reusability, at the trade effluents such as modified cellulose filter membrane of the invention can be used for being electroplated, metallurgy, papermaking, printing and dyeing
Reason.
Claims (7)
1. a kind of preparation method of modified cellulose filter membrane, it is characterised in that：Include the following steps：
(1) cellophane is immersed in dichloromethane, chloroform, toluene or dimethylbenzene, pyridine and 2- bromine isobutyryls is added dropwise
Cellulose base macromole evocating agent is obtained by the reaction in bromine；Wherein, the amount of substance compares pyridine：2- bromine isobutyl acylbromides：Cellophane=
0.3-3：0.3-3：1；
(2) cellulose base macromole evocating agent is placed in aqueous solution, catalyst cuprous bromide, ligand N, N, N', N is added, '
N "-five methyl diethylentriamines and anionic monomer carry out deoxygenation operation, then react for 24 hours, are cleaned and dried at 50 DEG C
Afterwards, modified cellulose filter membrane is obtained；Wherein, the amount ratio of the substance of cuprous bromide and cellophane is 0.05-1：1；N,N,N',
N, ' the amount ratio 0.8-2 of the substance of N "-five methyl diethylentriamines and cuprous bromide：1.
2. a kind of preparation method of modified cellulose filter membrane as described in claim 1, it is characterised in that：In (2), it is cloudy from
The amount ratio of the substance of sub- monomer and cellophane is 0.5-10：1.
3. a kind of preparation method of modified cellulose filter membrane as claimed in claim 2, it is characterised in that：The anionic monomer
Amount ratio with the substance of cellophane is 2.0-8：1.
4. a kind of preparation method of modified cellulose filter membrane as described in claim 1, it is characterised in that：The anionic monomer
For 2- acrylamide-2-methyl propane sulfonics.
5. a kind of preparation method of modified cellulose filter membrane as described in claim 1, it is characterised in that：The modified cellulose
The thickness of filter membrane is 0.1-1000 μm.
6. a kind of modified cellulose filter membrane, it is characterised in that：Its molecular structural formula is such as：
Wherein, n=5~40.
7. a kind of modified cellulose filter membrane as claimed in claim 6, it is characterised in that：The thickness of the modified cellulose filter membrane
It is 0.1-1000 μm.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117599624A (en) * | 2023-11-21 | 2024-02-27 | 舟山市食品药品检验检测研究院 | Nano plastic detection method |
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| CN102188956A (en) * | 2011-04-13 | 2011-09-21 | 南京大学 | Heavy metal adsorption copolymer with sulfonic acid group and preparation method thereof, and application of heavy metal adsorption copolymer to water treatment |
| US20130048563A1 (en) * | 2011-08-30 | 2013-02-28 | General Electric Company | Tannin polymers as aids for reducing fouling of ceramic membranes |
| CN103193938A (en) * | 2013-05-03 | 2013-07-10 | 云南烟草科学研究院 | Preparation method of modified cellulose acetate |
| CN106237875A (en) * | 2016-08-18 | 2016-12-21 | 福建农林大学 | A kind of preparation method of cellulose base cation selective filter membrane and products thereof |
| CN106750480A (en) * | 2016-12-20 | 2017-05-31 | 福建农林大学 | The preparation method of cellulose base water-oil separating film |
-
2018
- 2018-04-16 CN CN201810337225.4A patent/CN108636135A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102188956A (en) * | 2011-04-13 | 2011-09-21 | 南京大学 | Heavy metal adsorption copolymer with sulfonic acid group and preparation method thereof, and application of heavy metal adsorption copolymer to water treatment |
| US20130048563A1 (en) * | 2011-08-30 | 2013-02-28 | General Electric Company | Tannin polymers as aids for reducing fouling of ceramic membranes |
| CN103193938A (en) * | 2013-05-03 | 2013-07-10 | 云南烟草科学研究院 | Preparation method of modified cellulose acetate |
| CN106237875A (en) * | 2016-08-18 | 2016-12-21 | 福建农林大学 | A kind of preparation method of cellulose base cation selective filter membrane and products thereof |
| CN106750480A (en) * | 2016-12-20 | 2017-05-31 | 福建农林大学 | The preparation method of cellulose base water-oil separating film |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117599624A (en) * | 2023-11-21 | 2024-02-27 | 舟山市食品药品检验检测研究院 | Nano plastic detection method |
| CN117599624B (en) * | 2023-11-21 | 2024-05-10 | 舟山市食品药品检验检测研究院 | Nano plastic detection method |
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