CN116063713B - Preparation method of high-haze nanocellulose-based hydrophobic film with oil stain detection and oil-water separation functions - Google Patents
Preparation method of high-haze nanocellulose-based hydrophobic film with oil stain detection and oil-water separation functions Download PDFInfo
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- 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
- C02F1/40—Devices for separating or removing fatty or oily substances or similar floating material
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/12—Preparation of cellulose esters of organic acids of polybasic organic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
- C08F251/02—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof on to cellulose or derivatives thereof
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- 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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- 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
- C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- C08J2351/02—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers grafted on to polysaccharides
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A20/00—Water conservation; Efficient water supply; Efficient water use
- Y02A20/20—Controlling water pollution; Waste water treatment
- Y02A20/204—Keeping clear the surface of open water from oil spills
Abstract
The application discloses a preparation method of a nanocellulose-based hydrophobic film with oil stain detection and oil-water separation functions, which is characterized in that CNCs nano particles are modified by a DDSA (direct-flow SA) esterification and TFMA (reverse-flow Mass Spectrometry) free radical copolymerization method, and a surface modified CNCs suspension is subjected to vacuum suction filtration to prepare the film, wherein the obtained modified film has high transparency and high optical haze (89.8%) due to ordered arrangement of the CNCs nano particles. In addition, as the hydrophobic molecules are successfully grafted on the surfaces of the nano particles, the contact angle of the hydrophobic film reaches 131.6 degrees, and the separation efficiency of the oil-water emulsion reaches 94.5 percent. The surface modification of the nano CNCs provides a simple method for rapid detection and separation of pollutants, and expands the application potential of renewable cellulose resources in the fields of environmental protection, engineering control and petroleum industry.
Description
Technical Field
The application belongs to the technical field of nano film materials, and particularly relates to a method for preparing a composite film with organic pollutant removing capability.
Background
As such, oil separation has become a major concern in many areas. The production of functional materials for the detection and removal of organic contaminants based on renewable and sustainable resources is of great interest. At present, the oil-water separation method is simple and low in cost, but has the defects of poor separation performance, low separation efficiency and the like. More importantly, the increasingly severe requirements for rapid detection and separation of material decontamination cannot be met. Cellulose has received a great deal of attention as the most abundant biopolymer on earth in the application field of environmentally friendly, renewable and sustainable materials. The CNCs have the advantages of high rigidity, high specific surface area, amphipathy, colloid property, chirality and the like, and the thin film prepared from the nanocellulose crystal and having a chiral nematic structure has unique nano characteristics, so that the thin film has the optical properties of polarization property, haze, iridescence and the like in two-dimensional materials such as the thin film and the like, and has important significance in expanding the application field of the thin film. Compared with the traditional material, the material obtained by grafting modification has the characteristics of stable property, good separation effect and higher separation efficiency, and the preparation method is environment-friendly, simple and convenient to operate and wide in application prospect.
Disclosure of Invention
In order to solve the problem of increasingly focused emulsifying agents and make up the defects of the traditional surfactants, the technical problem to be solved by the application is to provide a preparation method of a high-haze nanocellulose-based hydrophobic film with the functions of oil stain detection and oil-water separation, CNCs nano particles are modified by a DDSA (direct-flow SA) esterification and TFMA (reverse flow-Mass Spectrometry) free radical copolymerization method, a film is prepared from a surface-modified CNCs suspension by vacuum suction filtration, and the obtained material has high hydrophobicity and high haze, and can be used for effectively detecting and separating organic pollutants.
In order to solve the technical problems, the application adopts the following technical scheme:
the preparation method of the high-haze nanocellulose-based hydrophobic film with the functions of oil stain detection and oil-water separation comprises the following steps:
1) Catalyzing dodecenyl succinic anhydride (DDSA) and CNCs in dimethyl sulfoxide (DMSO) to perform esterification reaction to obtain an esterified product;
2) Adding 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecetylethyl acrylate (TFMA) into an esterified product in Tetrahydrofuran (THF) under the protection of nitrogen, and carrying out copolymerization reaction to obtain a sample;
3) Homogenizing the sample, and vacuum filtering to form the membrane.
The preparation method of the high-haze nanocellulose-based hydrophobic film with the functions of oil stain detection and oil-water separation comprises the following steps of: 0.1 to 0.8.
In the step 1), the catalyst for the esterification reaction is 4-Dimethylaminopyridine (DMAP).
In step 1), the esterification reaction was carried out at 60℃for 10 hours.
In step 2), azobisisobutyronitrile (AIBN) is added to carry out the copolymerization.
In the step 2), the stirring and catalyzing copolymerization reaction is carried out for 3 hours at 65 ℃.
The preparation method of the high-haze nanocellulose-based hydrophobic film with the functions of oil stain detection and oil-water separation comprises the following steps of: 0.5.
the preparation method of the high-haze nanocellulose-based hydrophobic film with the functions of oil stain detection and oil-water separation comprises the following steps:
1) Adding CNCs powder and DDSA into a reaction container, adding DMSO and a catalytic amount of DMAP, and treating at 60 ℃ for 10 hours; centrifuging to obtain solid, washing twice with acetone, and placing in THF for standby;
2) Under the protection of nitrogen, adding TFMA, mixing, adding AIBN, stirring at 65 ℃, and catalyzing and copolymerizing for 3 hours;
3) After the reaction is finished, obtaining solid by centrifugal separation, washing the solid twice by acetone, and re-dispersing the solid in water; performing ultrasonic treatment to homogenize the sample; finally, the nanocellulose-based film is prepared by vacuum filtration.
The high-haze nanocellulose-based hydrophobic film with the functions of oil stain detection and oil-water separation is prepared by the method. The composite film has 85% optical haze, a contact angle of 131.6 degrees and the separation efficiency of organic pollutants is more than or equal to 90% of the oil-water emulsion.
The high-haze nanocellulose-based hydrophobic film with the functions of oil stain detection and oil-water separation is applied to oil stain detection and oil-water separation.
The beneficial effects are that: compared with the prior art, the application has the advantages that:
1) The film prepared by the method has unique optical function, and has the characteristics of high transparency, optical haze (89.8%), rapid and sensitive detection of organic pollutants and the like. Meanwhile, the separation efficiency of the membrane prepared by the application on organic pollutant-water emulsion reaches 94.5%. Compared with the traditional organic pollutant remover, the material is green and environment-friendly, the natural stock is rich, no harmful substances are added, the degradation capability is strong, and the application prospect is wide.
2) At present, the preparation of a high optical haze cellulose film mainly depends on a mechanical action with larger energy consumption (a preparation method of a high light transmittance high haze cellulose film, CN 114753175A) or a petroleum-based polymer is used as a substrate to be composited with cellulose for preparation (a nano cellulose film for optical use, a preparation method and application thereof, CN111300918A; an optical nanocellulose film, a preparation method and application thereof, CN 111300918B).
Compared with the prior art, the method directly graft-modifies the nanocellulose to obtain the optical haze which is close to that of other prior art, but the method has lower energy consumption and saves cost without doping other high molecular polymers. Meanwhile, the application can prepare the cellulose base film without depending on other composite polymers, the separation efficiency is 94.5 percent, which is similar to or higher than that of the reported all-cellulose base oil water separation film (Ao et al Carbohydrate Polymers,2020, 116872; the preparation method of super-hydrophobic cellulose paper for oil-water separation, CN 113186756A).
Drawings
FIG. 1 is a graph showing the results of ultraviolet absorption spectrum test (200-800 nm) (a) and haze analysis (400-800 nm) (b) of composite films with different DDSA addition amounts;
FIG. 2 is a photograph of the contact angle of a composite film with various DDSA additions taken (a) and observing untreated (b), immersed in water (c) and immersed in benzene (d) with a polarizing microscope;
FIG. 3 is a photograph of a benzene/water emulsion separation process of a CDF-4 set of composite films (a); and separation efficiency and flux results for different membrane materials (b).
Detailed Description
The application will be further illustrated with reference to specific examples.
Example 1
The preparation method of the high-haze nanocellulose-based hydrophobic film with the functions of oil stain detection and oil-water separation comprises the following specific steps:
1) 1.5g of CNCs powder and 0.22g of DDSA were added to a 100mL beaker; 40mL of DMSO and 1.02g of DMAP were added and treated at 60℃for 10 hours. The solid was obtained by centrifugation and washed twice with acetone and then placed in 60ml of hf.
2) Adding 1.8g TFMA to the system of step 1) for mixing; under the protection of nitrogen, 0.015g of AIBN is added, and the mixture is stirred at 65 ℃ to catalyze the copolymerization reaction for 3 hours.
3) After the reaction was completed, the solid was obtained by centrifugal separation, washed twice with acetone, and redispersed in water. Ultrasonic (power 100W, frequency 40 Hz) treatment was performed to homogenize the sample. Finally, the nanocellulose-based film CDF1 was prepared by vacuum filtration at room temperature.
By adopting the method, the adding amount of DDSA is respectively regulated to be 0.67g,1.11g and 1.76g, the mol ratio of the corresponding CNCs to the DDSA is respectively 1:0.3, 1:0.5 and 1:0.8, and the nanocellulose-based films CDF2, CDF3 and CDF4 are correspondingly prepared.
Example 2
The nanocellulose-based film prepared in example 1 was subjected to product performance testing, specifically: the transmittance and haze of the material were measured using an ultraviolet spectrophotometer UV-vis spectrophotometer (Perkin-Elmer, lambda 950, USA). The degree of hydrophilicity and hydrophobicity of the materials was analyzed using a contact angle meter Kino SL200KS 150 contact angle analyzer. Iridescence of the film was observed by a polarizing microscope Carl Zeiss (Axio Observer A1).
Rapid and sensitive detection of organic pollutants. Soaking the obtained nanocellulose film in water for 1s, taking out, air-drying, and observing the optical iridescence phenomenon of the film under a polaroid; the same method replaces water with toluene to observe the optical iridescence phenomenon of the film, and is used for judging the detection performance of the product on organic pollutants.
The separation experiment of the film on the organic pollutant-water emulsion adopts a gravity method to lead the benzene-water uniform emulsion with the tween-80 stability to pass through the prepared film. The separation efficiency calculation method is as follows:
wherein R is separation efficiency, C 0 And C f The concentration of benzene in the original emulsion and the upper emulsion after separation, respectively, was calculated by the volumetric method.
Ultraviolet absorption spectrum tests (200-800 nm) (fig. 1 a) and haze analyses (400-800 nm) (fig. 1 b) of the composite films with different DDSA additions showed that the films prepared had high transparency (> 85%) and high haze (94.5%).
The contact angles of the composite films with different DDSA addition amounts were photographed (fig. 2a, table 1), and the untreated (fig. 2 b), immersed for 1s (fig. 2 c), and immersed in toluene for 1s (fig. 2 d) were observed by using a polarizing microscope; indicating that the iridescence phenomenon of the film immersed by toluene disappears under the polaroid, and indicating that the film can be used for rapidly detecting organic pollutants.
Photographs of benzene/water emulsion separation process of CDF-4 group composite films (FIG. 3 a); and the separation efficiency and flux results for the different membrane materials (fig. 3 b), demonstrate that CDF-3 membranes have the highest separation efficiency, up to 94.5%. The separation efficiency of other modified films is higher than 90 percent. The retention rates are all higher than 50Lm -3 h -1 。
TABLE 1 results of product Performance test
| Sample of | Transparency of the film | Optical haze | Contact angle of water | Separation efficiency | Flow rate |
| CDF-1 | 79％ | 81.2％ | 76.8° | 94.0％ | 52.9Lm -3 h -1 |
| CDF-2 | 77％ | 85.7％ | 86.5° | 90.5％ | 54.5Lm -3 h -1 |
| CDF-3 | 89％ | 87.9％ | 131.6° | 94.5％ | 55Lm -3 h -1 |
| CDF-4 | 85％ | 89.8％ | 125.2° | 91.0％ | 53.6Lm -3 h -1 |
Table 1 shows that the films prepared according to the application have a high transparency (89%) and a high haze (89.8%). Under the condition of keeping high flux, the oil-water separation efficiency is up to 94.5%. Meanwhile, the optical haze of the prepared nanocellulose composite film increases with the increase of the DDSA dosage, and the hydrophobicity (water contact angle) of the film increases.
Comparative example 1
Preparation of nanocellulose-based film CD-1: 1.5g of CNCs powder and 0.22g of DDSA were added to a 100mL beaker, followed by 40mL of DMSO and 1.02g of DMAP, and treated at 60℃for 10 hours. The solid was obtained by centrifugation and after washing twice with acetone, redispersed in water. Ultrasonic (power 100W, frequency 40 Hz) treatment was performed to homogenize the sample. Finally, the nanocellulose-based film CD-1 is prepared by vacuum filtration at room temperature.
Comparative example 2
Preparation of nanocellulose-based film CD-4: 1.5g of CNCs powder and 1.76g of DDSA were added to a 100mL beaker, 40mL of MSO and 1.02g of DMAP were added and treated at 60℃for 10 hours. The solid was obtained by centrifugation and after washing twice with acetone, redispersed in water. Ultrasonic (power 100W, frequency 40 Hz) treatment was performed to homogenize the sample. Finally, the nanocellulose-based film CD-4 is prepared by vacuum filtration at room temperature.
Comparative example 3
Preparation of nanocellulose-based film CF-1: 1.5g of CNCs powder and 1.8g of TFMA were added to a 100mL beaker and dispersed by addition of 60mL of HF; under the protection of nitrogen, 0.015g of AIBN is added for mixing, and the mixture is stirred at 65 ℃ to catalyze the copolymerization reaction for 3 hours. The solid was obtained by centrifugation, the sample was washed twice with acetone and redispersed in water. Ultrasonic (power 100W, frequency 40 Hz) treatment was performed to homogenize the sample. Finally, the nanocellulose-based film CF-1 is prepared by vacuum filtration at room temperature.
Comparative example 4
Preparation of nanocellulose-based film CF-2: 1.5g of CNCs powder and 3.6g of TFMA were added to a 100mL beaker and dispersed by adding 60mL of THF. After 0.015g of AIBN was added and mixed under the protection of nitrogen, the mixture was stirred at 65℃to catalyze copolymerization for 3 hours. The solid was obtained by centrifugation, the sample was washed twice with acetone and redispersed in water. Ultrasonic (power 100W, frequency 40 Hz) treatment was performed to homogenize the sample. Finally, the nanocellulose-based film CF-2 is prepared by vacuum filtration at room temperature.
The optical properties and oil-water separation effects of the products of comparative examples 1 to 4 were measured by the same method as in example 2, and the results are shown in Table 2. Compared to the film sample of example 1, the nanocellulose material prepared in table 2 failed to achieve a combination of high light transmittance, optical haze, and high oil-water separation efficiency.
TABLE 2 results of product Performance test
| Sample of | Transparency of the film | Optical haze | Separation efficiency | Flow rate |
| CD-1 | 81％ | 72.2％ | 67.0％ | 36.2Lm -3 h -1 |
| CD-4 | 74％ | 78.7％ | 76.4％ | 44.1Lm -3 h -1 |
| CF-1 | 60％ | 48.1％ | 58.0％ | 18.9Lm -3 h -1 |
| CF-2 | 7％ | —— | —— | —— |
Among them, in comparative example 4, CF-2 failed to form a light-transmitting film due to the large amount of TFMA added, and had a transparency of 7% and had no oil-water separation function (table 2).
Claims (8)
1. The preparation method of the high-haze nanocellulose-based hydrophobic film with the functions of oil stain detection and oil-water separation is characterized by comprising the following steps of:
1) In dimethyl sulfoxide, catalyzing dodecenyl succinic anhydride and cellulose nanocrystals to perform esterification reaction to obtain an esterified product; the molar ratio of cellulose nanocrystals to dodecenyl succinic anhydride was 1:0.1 to 0.8;
2) Under the protection of nitrogen, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecetfluoroethyl acrylate is added into the esterified product to carry out copolymerization reaction in tetrahydrofuran to obtain a sample; adding azodiisobutyronitrile to carry out copolymerization reaction;
3) Homogenizing the sample, and vacuum filtering to form the membrane.
2. The method for preparing a high-haze nanocellulose-based hydrophobic film with oil stain detection and oil-water separation functions according to claim 1, wherein in step 1), the catalyst for the esterification reaction is 4-dimethylaminopyridine.
3. The method for preparing a high-haze nanocellulose-based hydrophobic film with both oil stain detection and oil-water separation functions according to claim 1, wherein in step 1), the esterification reaction is carried out at 60 ℃ for 10 hours.
4. The method for preparing the high-haze nanocellulose-based hydrophobic film with the functions of oil stain detection and oil-water separation according to claim 1, wherein in the step 2), the stirring catalytic copolymerization is carried out for 3 hours at 65 ℃.
5. The method for preparing the high-haze nanocellulose-based hydrophobic film with the functions of oil stain detection and oil-water separation according to claim 1, wherein the molar ratio of cellulose nanocrystals to 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecetfluoroethyl acrylate is 1:0.5.
6. the method for preparing the high-haze nanocellulose-based hydrophobic film with the functions of oil stain detection and oil-water separation according to any one of claims 1 to 5, which is characterized by comprising the following steps:
1) Adding cellulose nanocrystal powder and dodecenyl succinic anhydride into a reaction container, adding dimethyl sulfoxide and a catalytic amount of 4-dimethylaminopyridine, and treating at 60 ℃ for 10 hours; centrifuging to obtain solid, washing twice with acetone, and placing in tetrahydrofuran for standby;
2) Under the protection of nitrogen, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoroethyl acrylate is added for mixing, azodiisobutyronitrile is added, and stirring is carried out at 65 ℃ for catalytic copolymerization for 3 hours;
3) After the reaction is finished, obtaining solid by centrifugal separation, washing the solid twice by acetone, and re-dispersing the solid in water; performing ultrasonic treatment to homogenize the sample; finally, the nanocellulose-based film is prepared by vacuum filtration.
7. The high-haze nanocellulose-based hydrophobic film with the functions of oil stain detection and oil-water separation, which is prepared by the method of any one of claims 1-6.
8. The application of the high-haze nanocellulose-based hydrophobic film with the oil stain detection and oil-water separation functions in oil stain detection and oil-water separation of claim 7.
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| CN101716471A (en) * | 2010-01-21 | 2010-06-02 | 天津大学 | Fluorizated cellulose acetate film and preparation method |
| CN108264613A (en) * | 2018-03-09 | 2018-07-10 | 天津科技大学 | A kind of nanofibrils cellulose surface hydrophobically modified method |
| CN113186756A (en) * | 2021-05-13 | 2021-07-30 | 淮阴工学院 | Preparation method of super-hydrophobic cellulose paper for oil-water separation |
| CN114478924A (en) * | 2022-01-12 | 2022-05-13 | 华南师范大学 | Organic dielectric material, composite film, preparation method and application thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101716471A (en) * | 2010-01-21 | 2010-06-02 | 天津大学 | Fluorizated cellulose acetate film and preparation method |
| CN108264613A (en) * | 2018-03-09 | 2018-07-10 | 天津科技大学 | A kind of nanofibrils cellulose surface hydrophobically modified method |
| CN113186756A (en) * | 2021-05-13 | 2021-07-30 | 淮阴工学院 | Preparation method of super-hydrophobic cellulose paper for oil-water separation |
| CN114478924A (en) * | 2022-01-12 | 2022-05-13 | 华南师范大学 | Organic dielectric material, composite film, preparation method and application thereof |
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