CN109091914B - Preparation method and application of super-hydrophobic polyurea-cellulose composite material - Google Patents
Preparation method and application of super-hydrophobic polyurea-cellulose composite material Download PDFInfo
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- CN109091914B CN109091914B CN201810979955.4A CN201810979955A CN109091914B CN 109091914 B CN109091914 B CN 109091914B CN 201810979955 A CN201810979955 A CN 201810979955A CN 109091914 B CN109091914 B CN 109091914B
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
- B01D17/02—Separation of non-miscible liquids
- B01D17/0202—Separation of non-miscible liquids by ab- or adsorption
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
- B01D17/02—Separation of non-miscible liquids
- B01D17/04—Breaking emulsions
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/09—Sulfur-containing compounds
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
- D21H17/57—Polyureas; Polyurethanes
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Abstract
The invention discloses a preparation method and application of a super-hydrophobic polyurea-cellulose composite material, belongs to the field of high polymers and porous materials, and is used for separating an oil-water mixture and a water-in-oil emulsion. The method comprises the following specific steps: (1) preparing maleimide-polyurea coated cellulose filter paper MPUFs, and (2) preparing super-hydrophobic polyurea-cellulose composite SHFs by a one-step method. The product is simple to prepare, can be produced in large scale, is used for continuously separating oil-water mixture and water-in-oil emulsion, has high separation efficiency, greatly reduces the treatment cost of industrial oily wastewater, reduces the pollution of crude oil leakage to water, and has potential application value, economic benefit and social benefit.
Description
Technical Field
The invention relates to a preparation method and application of a super-hydrophobic polyurea-cellulose composite material, belonging to the field of polymer chemistry and porous materials.
Background
Since two scholars of Barthlott and Neinhuis reported the super-hydrophobic property of the lotus leaf surface, namely the lotus leaf effect, the scholars have generated research interest on super-hydrophobic materials. Super-hydrophobicity refers to the contact angle between the surface of the material and water being more than 1500Sliding angle less than 100. Water droplets roll off very easily on the surface of the material due to their extremely low surface free energy and rough surface morphology, and are therefore also referred to as "lotus effect".
There are many common methods for preparing superhydrophobic surfaces, such as chemical etching, layer-by-layer assembly, solution immersion, electrochemical methods, templating, and vapor deposition. However, in general, the existing methods have disadvantages that the chemical etching method cannot produce a regular surface structure; the template etching method is complex in preparation and is difficult to be used for manufacturing a large-area super-hydrophobic surface; the electrochemical method and the vapor deposition method have the defects of high cost, harsh preparation conditions and the like.
Crude oil leakage and oily wastewater discharged by industry seriously damage the ecological environment, thereby causing great threat to human health, and developing high-efficiency oil-water separation technology and materials has become one of the leading topics in the world. The traditional oil-water separation method, such as combustion, air flotation, coagulation-flocculation and biological treatment, has low separation efficiency, high energy consumption, complicated process and even secondary pollution. Although the adsorption process using porous material with specific wettability surface can realize high efficiency oil-water separation, these adsorbents need to be separated and regenerated by washing, compression or distillation, which will certainly consume more manpower, material resources and energy. The appearance of the super-hydrophobic material just solves the problem, so that the research on the functionalized super-hydrophobic coating has far-reaching significance.
Disclosure of Invention
One of the technical tasks of the invention is to make up the defects of the prior art and provide a preparation method and application of a super-hydrophobic polyurea-cellulose composite material.
The second technical task of the invention is to provide the application of the super-hydrophobic polyurea-cellulose composite material, namely the super-hydrophobic polyurea-cellulose composite material is used for separating oil-water mixture and water-in-oil emulsion, and has good separation activity and stability.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
1. a preparation method of a super-hydrophobic polyurea-cellulose composite material comprises the following steps:
(1) preparation of Maleimide-polyurea coated cellulose Filter papers MPUFs
Dissolving 2-6g of toluene diisocyanate and 2-6g N- (2, 4-diaminophenyl) maleimide in 200mL of acetonitrile, soaking the filter paper in the solution for 20-40min, circulating for 2-4 times, and air-drying at room temperature to obtain the maleimide-polyurea coated cellulose filter paper MPUFs;
the maleimide-polyurea coated cellulose filter paper MPUFs have the following structural formula:
(2) preparation of super-hydrophobic polyurea-cellulose composite SHFs
Dissolving 2-6g of n-dodecyl mercaptan and 1-3g of triethylamine in 200mL of ethanol, and soaking the cellulose filter paper MPUFs coated with the maleimide-polyurea in the solution for 5-15min to obtain super-hydrophobic polyurea-cellulose composite SHFs;
the diameter of the super-hydrophobic polyurea-cellulose composite material SHFs is 18 cm;
the super-hydrophobic polyurea-cellulose composite material SHFs is super-hydrophobic filter paper with a water contact angle of 150-152.3 degrees and an oil contact angle of 0 degree;
the super-hydrophobic polyurea-cellulose composite material SHFs has the structural formula as follows:
the toluene diisocyanate is a mixture of 2, 4-diisocyanate toluene and 2, 6-diisocyanate toluene, and the mass ratio of the toluene diisocyanate to the 2, 4-diisocyanate toluene is 8:2;
r1 is
And
the mass ratio is 8:2;
r2 is
。
2. The application of the super-hydrophobic polyurea-cellulose composite SHFs prepared by the preparation method in the step 1 in oil-water mixture separation comprises the following steps:
fixing the SHFs in a funnel to prepare a super-hydrophobic funnel;
dissolving 0.005g of Sudan red III in 50mL of petroleum ether to prepare a petroleum ether solution of Sudan red III; dissolving 0.005g of methyl blue in 50mL of distilled water to prepare a methyl blue aqueous solution; mixing the petroleum ether solution of Sudan red III with the methyl blue aqueous solution to prepare an oil-water mixture;
pouring the oil-water mixture into a super-hydrophobic funnel, wherein the oil solution can rapidly pass through the super-hydrophobic funnel, and the water solution is retained in the funnel and cannot be filtered out;
pouring an oil-water mixture sample to be separated into a super-hydrophobic funnel, wherein an oil solution can rapidly pass through the super-hydrophobic funnel, and an aqueous solution is reserved in the funnel and cannot be filtered out;
experimental results show that the super-hydrophobic polyurea-cellulose composite SHFs is used for separating oil-water mixtures, and after circulation is carried out for ten times, a good separation effect is still kept.
3. The application of the super-hydrophobic polyurea-cellulose composite SHFs prepared by the preparation method in the step 1 in water-in-oil emulsion separation comprises the following steps:
fixing the SHFs in a funnel to prepare a super-hydrophobic funnel;
dissolving 1mL of distilled water and 0.1 g of Span 80 in 50mL of 1, 2-dibromoethane, and carrying out ultrasonic treatment for half an hour to prepare a water-in-oil emulsion;
pouring the water-in-oil emulsion into a super-hydrophobic funnel, wherein the oil solution can rapidly pass through the super-hydrophobic funnel, and the water solution is retained in the funnel and cannot be filtered out;
pouring a water-in-oil emulsion sample to be separated into a super-hydrophobic funnel, wherein an oil solution can rapidly pass through the super-hydrophobic funnel, and an aqueous solution is reserved in the funnel and cannot be filtered out;
the ultrasonic treatment has the power of 2 kW;
the water-in-oil emulsion is a milky white solution;
experimental results show that the super-hydrophobic polyurea-cellulose composite SHFs is used for separating water-in-oil emulsion, and after circulation is carried out for ten times, the good separation effect is still kept.
The above required raw materials are all purchased in the local chemical industry market.
The beneficial technical effects of the invention are as follows:
(1) the preparation method of the super-hydrophobic polyurea-cellulose composite material SHFs comprises the steps of firstly preparing a polyurea porous Material (MPPU) containing a maleimide group by condensation precipitation polymerization of toluene diisocyanate and N- (2, 4-diaminophenyl) maleimide (NAPMI), and then carrying out hetero-Michael addition reaction with N-dodecyl mercaptan (DAT) to obtain the super-hydrophobic polyurea-cellulose composite material SHFs; the method has the advantages of simple operation, 25-55min reaction time, 150-152.3 degrees of water contact angle, 0 degree of oil contact angle and good separation effect.
(2) The super-hydrophobic polyurea-cellulose composite material SHFs prepared by the invention can be directly used for separating oil-water mixture and water-in-oil emulsion, when the oil-water mixture and the water-in-oil emulsion are dropped on the material, oil drops can permeate through a film layer, and the water drops can not permeate, thereby realizing oil-water separation. Compared with other conventional separation means, the method has the advantages of no requirement on equipment, easy operation, high stability and capability of continuous separation.
Detailed Description
The present invention is further described with reference to the following examples, but the scope of the present invention is not limited to the examples, and modifications made by those skilled in the art to the technical solutions of the present invention should fall within the scope of the present invention.
Example 1 preparation method of super-hydrophobic polyurea-cellulose composite material
(1) Preparation of Maleimide-polyurea coated cellulose Filter papers MPUFs
Dissolving 2g of toluene diisocyanate and 2g N- (2, 4-diaminophenyl) maleimide in 200mL of acetonitrile, soaking the filter paper in the solution for 20min, circulating for 2 times, and air-drying at room temperature to obtain maleimide-polyurea coated cellulose filter paper MPUFs;
the maleimide-polyurea coated cellulose filter paper MPUFs have the following structural formula:
(2) preparation of super-hydrophobic polyurea-cellulose composite SHFs
Dissolving 2g of n-dodecyl mercaptan and 1g of triethylamine in 200mL of ethanol, and soaking the cellulose filter paper MPUFs coated with the maleimide-polyurea in the solution for 5min to obtain super-hydrophobic polyurea-cellulose composite SHFs;
the diameter of the super-hydrophobic polyurea-cellulose composite material SHFs is 18 cm;
the super-hydrophobic polyurea-cellulose composite material SHFs is super-hydrophobic filter paper with a water contact angle of 150-152.3 degrees and an oil contact angle of 0 degree;
the super-hydrophobic polyurea-cellulose composite material SHFs has the structural formula as follows:
the toluene diisocyanate is a mixture of 2, 4-diisocyanate toluene and 2, 6-diisocyanate toluene, and the mass ratio of the toluene diisocyanate to the 2, 4-diisocyanate toluene is 8:2;
r1 is
And
the mass ratio is 8:2;
r2 is
。
Example 2 preparation method of super-hydrophobic polyurea-cellulose composite material
(1) Preparation of Maleimide-polyurea coated cellulose Filter papers MPUFs
Dissolving 4g of toluene diisocyanate and 4g N- (2, 4-diaminophenyl) maleimide in 200mL of acetonitrile, soaking the filter paper in the solution for 30min, circulating for 3 times, and air-drying at room temperature to obtain maleimide-polyurea coated cellulose filter paper MPUFs;
the maleimide-polyurea coated cellulose filter paper MPUFs have the following structural formula:
(2) preparation of super-hydrophobic polyurea-cellulose composite SHFs
Dissolving 4g of n-dodecyl mercaptan and 2g of triethylamine in 200mL of ethanol, and soaking the cellulose filter paper MPUFs coated with the maleimide-polyurea in the solution for 10min to obtain super-hydrophobic polyurea-cellulose composite SHFs;
the diameter of the super-hydrophobic polyurea-cellulose composite material SHFs is 18 cm;
the super-hydrophobic polyurea-cellulose composite material SHFs is super-hydrophobic filter paper with a water contact angle of 150-152.3 degrees and an oil contact angle of 0 degree;
the super-hydrophobic polyurea-cellulose composite material SHFs has the structural formula as follows:
the toluene diisocyanate is a mixture of 2, 4-diisocyanate toluene and 2, 6-diisocyanate toluene, and the mass ratio of the toluene diisocyanate to the 2, 4-diisocyanate toluene is 8:2;
r1 is
And
the mass ratio is 8:2;
r2 is
。
Example 3 preparation method of super-hydrophobic polyurea-cellulose composite material
(1) Preparation of Maleimide-polyurea coated cellulose Filter papers MPUFs
Dissolving 6g of toluene diisocyanate and 6g N- (2, 4-diaminophenyl) maleimide in 200mL of acetonitrile, soaking the filter paper in the solution for 40min, circulating for 4 times, and air-drying at room temperature to obtain maleimide-polyurea coated cellulose filter paper MPUFs;
the maleimide-polyurea coated cellulose filter paper MPUFs have the following structural formula:
(2) preparation of super-hydrophobic polyurea-cellulose composite SHFs
Dissolving 6g of n-dodecyl mercaptan and 3g of triethylamine in 200mL of ethanol, and soaking the cellulose filter paper MPUFs coated with the maleimide-polyurea in the solution for 15min to obtain super-hydrophobic polyurea-cellulose composite SHFs;
the diameter of the super-hydrophobic polyurea-cellulose composite material SHFs is 18 cm;
the super-hydrophobic polyurea-cellulose composite material SHFs is super-hydrophobic filter paper with a water contact angle of 150-152.3 degrees and an oil contact angle of 0 degree;
the super-hydrophobic polyurea-cellulose composite material SHFs has the structural formula as follows:
the toluene diisocyanate is a mixture of 2, 4-diisocyanate toluene and 2, 6-diisocyanate toluene, and the mass ratio of the toluene diisocyanate to the 2, 4-diisocyanate toluene is 8:2;
r1 is
And
the mass ratio is 8:2;
r2 is
。
Example 4 use of the SHFs of the super-hydrophobic polyurea-cellulose composite materials described in examples 1 to 3 for oil-water mixture separation
Fixing the SHFs in a funnel to prepare a super-hydrophobic funnel;
dissolving 0.005g of Sudan red III in 50mL of petroleum ether to prepare a petroleum ether solution of Sudan red III; dissolving 0.005g of methyl blue in 50mL of distilled water to prepare a methyl blue aqueous solution; mixing the petroleum ether solution of Sudan red III with the methyl blue aqueous solution to prepare an oil-water mixture;
pouring the oil-water mixture into a super-hydrophobic funnel, wherein the oil solution can rapidly pass through the super-hydrophobic funnel, and the water solution is retained in the funnel and cannot be filtered out;
pouring an oil-water mixture sample to be separated into a super-hydrophobic funnel, wherein an oil solution can rapidly pass through the super-hydrophobic funnel, and an aqueous solution is reserved in the funnel and cannot be filtered out;
experimental results show that the super-hydrophobic polyurea-cellulose composite SHFs is used for separating oil-water mixtures, and after circulation is carried out for ten times, a good separation effect is still kept.
Example 5 use of the SHFs of the superhydrophobic polyurea-cellulose composites described in examples 1-3 for the separation of water-in-oil emulsions
Fixing the SHFs in a funnel to prepare a super-hydrophobic funnel;
dissolving 1mL of distilled water and 0.1 g of Span 80 in 50mL of 1, 2-dibromoethane, and carrying out ultrasonic treatment for half an hour to prepare a water-in-oil emulsion;
pouring the water-in-oil emulsion into a super-hydrophobic funnel, wherein the oil solution can rapidly pass through the super-hydrophobic funnel, and the water solution is retained in the funnel and cannot be filtered out;
pouring a water-in-oil emulsion sample to be separated into a super-hydrophobic funnel, wherein an oil solution can rapidly pass through the super-hydrophobic funnel, and an aqueous solution is reserved in the funnel and cannot be filtered out;
the ultrasonic treatment has the power of 2 kW;
the water-in-oil emulsion is a milky white solution;
experimental results show that the super-hydrophobic polyurea-cellulose composite SHFs is used for separating water-in-oil emulsion, and after circulation is carried out for ten times, the good separation effect is still kept.
Claims (8)
1. A preparation method of a super-hydrophobic polyurea-cellulose composite material is characterized by comprising the following steps:
(1) preparation of Maleimide-polyurea coated cellulose Filter papers MPUFs
Dissolving 2-6g of toluene diisocyanate and 2-6g N- (2, 4-diaminophenyl) maleimide in 200mL of acetonitrile, soaking the filter paper in the solution for 20-40min, circulating for 2-4 times, and air-drying at room temperature to obtain the maleimide-polyurea coated cellulose filter paper MPUFs;
the maleimide-polyurea coated cellulose filter paper MPUFs have the following structural formula:
(2) preparation of super-hydrophobic polyurea-cellulose composite SHFs
Dissolving 2-6g of n-dodecyl mercaptan and 1-3g of triethylamine in 200mL of ethanol, and soaking the cellulose filter paper MPUFs coated with the maleimide-polyurea in the solution for 5-15min to obtain super-hydrophobic polyurea-cellulose composite SHFs;
the diameter of the super-hydrophobic polyurea-cellulose composite material SHFs is 18 cm;
the super-hydrophobic polyurea-cellulose composite material SHFs is super-hydrophobic filter paper with a water contact angle of 150-152.3 degrees and an oil contact angle of 0 degree;
the super-hydrophobic polyurea-cellulose composite material SHFs has the structural formula as follows:
2. the method of claim 1, wherein the toluene diisocyanate is a mixture of 2, 4-diisocyanate toluene and 2, 6-diisocyanate toluene at a mass ratio of 8: 2.
3. The method of claim 1The preparation method of the super-hydrophobic polyurea-cellulose composite material is characterized in that R1 is
And
the mass ratio is 8: 2.
4. The method for preparing the superhydrophobic polyurea-cellulose composite material of claim 1, wherein R2 is
。
5. The application of the SHFs prepared by the preparation method according to claim 1 in the separation of oil-water mixture.
6. Use of the SHFs prepared by the preparation method according to claim 1 for water-in-oil emulsion separation.
7. Use according to claim 5 for the separation of oil and water mixtures, characterized by the following steps:
fixing the SHFs in a funnel to prepare a super-hydrophobic funnel;
dissolving 0.005g of Sudan red III in 50mL of petroleum ether to prepare a petroleum ether solution of Sudan red III; dissolving 0.005g of methyl blue in 50mL of distilled water to prepare a methyl blue aqueous solution; mixing the petroleum ether solution of Sudan red III with the methyl blue aqueous solution to prepare an oil-water mixture;
pouring the oil-water mixture into a super-hydrophobic funnel, wherein the oil solution can rapidly pass through the super-hydrophobic funnel, and the water solution is retained in the funnel and cannot be filtered out;
and pouring the oil-water mixture sample to be separated into the super-hydrophobic funnel, wherein the oil solution can rapidly pass through the super-hydrophobic funnel, and the water solution is retained in the funnel and cannot be filtered out.
8. Use according to claim 6 for the separation of a water-in-oil emulsion, comprising the steps of:
fixing the SHFs in a funnel to prepare a super-hydrophobic funnel;
dissolving 1mL of distilled water and 0.1 g of Span 80 in 50mL of 1, 2-dibromoethane, and carrying out ultrasonic treatment for half an hour to prepare a water-in-oil emulsion;
pouring the water-in-oil emulsion into a super-hydrophobic funnel, wherein the oil solution can rapidly pass through the super-hydrophobic funnel, and the water solution is retained in the funnel and cannot be filtered out;
pouring a water-in-oil emulsion sample to be separated into a super-hydrophobic funnel, wherein an oil solution can rapidly pass through the super-hydrophobic funnel, and an aqueous solution is reserved in the funnel and cannot be filtered out;
the ultrasonic treatment has the power of 2 kW;
the water-in-oil emulsion is a milky white solution.
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| CN101518695A (en) * | 2008-02-27 | 2009-09-02 | 中国科学院化学研究所 | Super-hydrophobic and super-oleophilic oil-water separation mesh membrane and preparation method thereof |
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Effective date of registration: 20210930 Address after: 261312 Changyi Binhai (Xiaying) Economic Development Zone, Changyi City, Weifang City, Shandong Province Patentee after: SHANDONG JINCHANGSHU NEW MATERIAL TECHNOLOGY Co.,Ltd. Address before: 250022 No. 336, South Xin Zhuang West Road, Shizhong District, Ji'nan, Shandong Patentee before: University of Jinan |