CN109232969B - Preparation method and application of super-hydrophobic maleimide polyurea porous material - Google Patents
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- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
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- B01J20/28054—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/26—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a solid phase from a macromolecular composition or article, e.g. leaching out
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- C—CHEMISTRY; METALLURGY
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- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/02—Polyureas
Abstract
The invention discloses a preparation method and application of a super-hydrophobic maleimide polyurea porous material, belongs to the field of high polymers and porous materials, and is used for separating an oil-water mixture. The method comprises the following specific steps: (1) preparation of a maleimide polyurea porous material, and (2) preparation of a super-hydrophobic maleimide polyurea porous material. The product is easy to prepare, can be produced in large scale, is used for continuously separating oil-water mixtures, has high separation efficiency, greatly reduces the treatment cost of industrial oily wastewater, reduces the pollution of crude oil leakage to water bodies, 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 maleimide polyurea porous material, belonging to the fields of polymer chemistry and porous materials.
Background
Inspired by animals and plants in nature, plants such as lotus leaves and rose petals have super-hydrophobicity, and animals such as compound eye structures of mosquitoes, bee wings and moth wings are provided. Most typically, the lotus leaf is super-hydrophobic, water is converged into water drops on the lotus leaf and drops without infiltration or film formation, and the modern scholars refer to the lotus leaf effect.
Researchers find that the surface of the lotus leaf is covered with a wax layer and a micron/nanometer layered structure, so that most of water on the lotus leaf is in direct contact with air. The generation of the super-hydrophobic material is just caused by the simulation of biological structure, and the super-hydrophobic material has unique surface properties, such as: self-cleaning property, corrosion resistance, self-healing property and the like, and can be widely used in daily life, such as super-hydrophobic film of greenhouse vegetables, micro-flow non-loss liquid conveying and the like.
In the prior art, the strength and durability of the super-hydrophobic material are poor, the preparation method is complex, the process requirement is high, the batch production is difficult, and the like, and the micro-nano structure of the material can be damaged after long-term use in a severe external environment, so that the corrosion resistance is reduced, the application of the super-hydrophobic material in various fields is limited, and the research of the super-hydrophobic material draws wide attention in the scientific and industrial fields.
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 of the super-hydrophobic maleimide polyurea porous material, and the method has the advantages of low cost of raw materials, simple preparation process and industrial application prospect.
The second technical task of the invention is to provide the application of the super-hydrophobic maleimide polyurea porous material, and the super-hydrophobic maleimide polyurea porous material is used for separating oil-water mixtures 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 maleimide polyurea porous material comprises the following steps:
(1) preparation of Maleimide polyurea porous Material
Dissolving 1.0-4.0g of 4.0g N- (2, 4-diaminophenyl) maleimide in 90g of mixed solution of water and acetone with the mass ratio of 3/7, dropwise adding 6-9g of toluene diisocyanate at a constant speed under electric stirring, completing dropping for 30min, heating to 30 ℃, reacting for 2h, centrifuging, and washing with the mixed solution of water and acetone for three times to obtain the maleimide polyurea porous material, wherein the yield is 85-92%;
the maleimide polyurea porous material has the following structural formula:
the toluene diisocyanate is a mixture of 2, 4-isocyanate toluene and 2, 6-isocyanate toluene, and the mass ratio of the toluene diisocyanate to the 2, 4-isocyanate toluene is 8: 2;
(2) preparation of super-hydrophobic maleimide polyurea porous material
Dissolving 1.0-2.0g of dodecanethiol in 10ml of ethanol to prepare an ethanol solution of the dodecanethiol;
soaking 0.5-1.0g of the maleimide polyurea porous material in an ethanol solution of dodecyl mercaptan for 5h, filtering and drying at 60 ℃ to obtain the super-hydrophobic maleimide polyurea porous material;
the super-hydrophobic maleimide polyurea porous material is a super-hydrophobic porous material with a water contact angle of 150-155 degrees and an oil contact angle of 0 degrees;
the super-hydrophobic maleimide polyurea porous material has the structural formula as follows:
the R is1Is composed of
And
the mass ratio is 8: 2;
the R is2Is composed of
The R is3Is composed of
。
2. The preparation method of the N- (2, 4-diaminophenyl) maleimide in the step (1) comprises the following steps:
adding 3.68-7.36g of 2, 4-dinitroaniline into 50ml of N, N-dimethylformamide, dropwise adding a mixed solution of 2.97-5.94g of maleic anhydride and 20ml of N, N-dimethylformamide under magnetic stirring, reacting for 5 hours, adding 0.5-1.0g of concentrated sulfuric acid and 2.0-4.0g of phosphorus pentoxide, and reacting for 5 hours; adding 1.10-2.20g of iron powder and 10-20ml of saturated ammonium chloride solution, heating to 75 ℃, refluxing for 5h, filtering, performing rotary evaporation at 40 ℃, passing through a chromatographic column, wherein the eluent of the chromatographic column is a mixed solution of ethyl acetate and methanol, collecting the liquid with the deepest color, and performing rotary evaporation to obtain the N- (2, 4-diaminophenyl) maleimide with the yield of 90-94%.
3. The application of the super-hydrophobic maleimide polyurea porous material prepared by the preparation method in the step 1 in oil-water mixture separation comprises the following steps:
dissolving 0.005g of Sudan red III in 50ml of petroleum ether to prepare petroleum ether of Sudan red III; dissolving 0.005g of methyl blue in 50ml of distilled water to prepare a methyl blue aqueous solution; mixing petroleum ether of Sudan red III with methyl blue aqueous solution to obtain oil-water mixture;
filling the super-hydrophobic maleimide polyurea porous material into a chromatographic column to prepare the super-hydrophobic maleimide polyurea porous material chromatographic column;
pouring the oil-water mixture into a super-hydrophobic maleimide polyurea porous material chromatographic column, wherein the oil solution can rapidly pass through the super-hydrophobic maleimide polyurea porous material chromatographic column, and the water solution is retained in the chromatographic column and cannot be filtered out;
and pouring the oil-water mixture sample to be separated into the chromatographic column made of the maleimide polyurea porous material, wherein the oil solution can rapidly pass through the chromatographic column made of the super-hydrophobic maleimide polyurea porous material, and the water solution is retained in the chromatographic column and cannot be filtered out.
Experimental results show that the super-hydrophobic maleimide polyurea porous material is used for separating oil-water mixtures, and can still keep a good separation effect after circulation for ten times.
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) according to the preparation method of the super-hydrophobic maleimide polyurea porous material, the maleimide polyurea porous material is prepared by condensation, precipitation and polymerization of toluene diisocyanate and N- (2, 4-diaminophenyl) maleimide, and then the maleimide polyurea porous material and dodecanethiol undergo a hetero-Michael addition reaction, so that the super-hydrophobic maleimide polyurea porous material is obtained, and the preparation method is simple in synthesis process and good in separation effect.
(2) The super-hydrophobic maleimide polyurea porous material prepared by the invention can be directly used for separating an oil-water mixture, when the oil-water mixture is dripped on the material, water drops can not pass through the material, and oil drops can permeate through a film layer, so that the oil-water separation is realized. Compared with other conventional separation means, the method has no requirement on equipment, is easy to operate and high in stability, and can be used for 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 superhydrophobic maleimide polyurea porous material
(1) Preparation of Maleimide polyurea porous Material
Dissolving 1.0g of 1.0g N- (2, 4-diaminophenyl) maleimide in 90g of mixed solution of water and acetone in a mass ratio of 3/7, dropwise adding 6g of toluene diisocyanate at a constant speed under electric stirring, finishing dropping for 30min, heating to 30 ℃, reacting for 2h, centrifuging, and washing with the mixed solution of water and acetone for three times to obtain the maleimide polyurea porous material, wherein the yield is 85%;
the maleimide polyurea porous material has the following structural formula:
the toluene diisocyanate is a mixture of 2, 4-isocyanate toluene and 2, 6-isocyanate toluene, and the mass ratio of the toluene diisocyanate to the 2, 4-isocyanate toluene is 8: 2;
(2) preparation of super-hydrophobic maleimide polyurea porous material
Dissolving 1.0g of dodecanethiol in 10ml of ethanol to prepare an ethanol solution of the dodecanethiol;
soaking 0.5g of the maleimide polyurea porous material in an ethanol solution of dodecyl mercaptan for 5h, filtering and drying at 60 ℃ to obtain a super-hydrophobic maleimide polyurea porous material;
the super-hydrophobic maleimide polyurea porous material is a super-hydrophobic porous material with a water contact angle of 150-155 degrees and an oil contact angle of 0 degrees;
the super-hydrophobic maleimide polyurea porous material has the structural formula as follows:
the R is1Is composed of
And
the mass ratio is 8: 2;
the R is2Is composed of
The R is3Is composed of
。
Example 2 preparation method of superhydrophobic maleimide polyurea porous material
(1) Preparation of Maleimide polyurea porous Material
Dissolving 2.5g N- (2, 4-diaminophenyl) maleimide in 90g of mixed solution of water and acetone with the mass ratio of 3/7, dropwise adding 8.5g of toluene diisocyanate at a constant speed under electric stirring, finishing dropping for 30min, heating to 30 ℃, reacting for 2h, centrifuging, and washing with the mixed solution of water and acetone for three times to obtain the maleimide polyurea porous material, wherein the yield is 92%;
the maleimide polyurea porous material has the following structural formula:
the toluene diisocyanate is a mixture of 2, 4-isocyanate toluene and 2, 6-isocyanate toluene, and the mass ratio of the toluene diisocyanate to the 2, 4-isocyanate toluene is 8: 2;
(2) preparation of super-hydrophobic maleimide polyurea porous material
Dissolving 1.5g of dodecanethiol in 10ml of ethanol to prepare an ethanol solution of the dodecanethiol;
soaking 0.75g of the maleimide polyurea porous material in an ethanol solution of dodecyl mercaptan for 5h, filtering and drying at 60 ℃ to obtain a super-hydrophobic maleimide polyurea porous material;
the super-hydrophobic maleimide polyurea porous material is a super-hydrophobic porous material with a water contact angle of 150-155 degrees and an oil contact angle of 0 degrees;
the super-hydrophobic maleimide polyurea porous material has the structural formula as follows:
the R is1Is composed of
And
the mass ratio is 8: 2;
the R is2Is composed of
The R is3Is composed of
。
Example 3 preparation method of superhydrophobic maleimide polyurea porous material
(1) Preparation of Maleimide polyurea porous Material
Dissolving 4.0g of 4.0g N- (2, 4-diaminophenyl) maleimide in 90g of mixed solution of water and acetone in a mass ratio of 3/7, dropwise adding 9g of toluene diisocyanate at a constant speed under electric stirring, finishing dropping for 30min, heating to 30 ℃, reacting for 2h, centrifuging, and washing with the mixed solution of water and acetone for three times to obtain a maleimide polyurea porous material, wherein the yield is 89%;
the maleimide polyurea porous material has the following structural formula:
the toluene diisocyanate is a mixture of 2, 4-isocyanate toluene and 2, 6-isocyanate toluene, and the mass ratio of the toluene diisocyanate to the 2, 4-isocyanate toluene is 8: 2;
(2) preparation of super-hydrophobic maleimide polyurea porous material
Dissolving 2.0g of dodecanethiol in 10ml of ethanol to prepare an ethanol solution of the dodecanethiol;
soaking 1.0g of the maleimide polyurea porous material in an ethanol solution of dodecyl mercaptan for 5h, filtering and drying at 60 ℃ to obtain a super-hydrophobic maleimide polyurea porous material;
the super-hydrophobic maleimide polyurea porous material is a super-hydrophobic porous material with a water contact angle of 150-155 degrees and an oil contact angle of 0 degrees;
the super-hydrophobic maleimide polyurea porous material has the structural formula as follows:
the R is1Is composed of
And
the mass ratio is 8: 2;
the R is2Is composed of
The R is3Is composed of
。
EXAMPLE 4 preparation of N- (2, 4-diaminophenyl) maleimide as described in examples 1-3
Adding 3.68g of 2, 4-dinitroaniline into 50ml of N, N-dimethylformamide, dropwise adding a mixed solution of 2.97g of maleic anhydride and 20ml of N, N-dimethylformamide under magnetic stirring, reacting for 5 hours, adding 0.5g of concentrated sulfuric acid and 2.0g of phosphorus pentoxide, and reacting for 5 hours; adding 1.10g of iron powder and 10ml of saturated ammonium chloride solution, heating to 75 ℃, refluxing for 5h, filtering, performing rotary evaporation at 40 ℃, passing through a chromatographic column, collecting the liquid with the darkest color, and performing rotary evaporation to obtain the N- (2, 4-diaminophenyl) maleimide with the yield of 90%.
EXAMPLE 5 preparation of N- (2, 4-diaminophenyl) maleimide as described in examples 1-3
Adding 5.52g of 2, 4-dinitroaniline into 50ml of N, N-dimethylformamide, dropwise adding a mixed solution of 4.46g of maleic anhydride and 20ml of N, N-dimethylformamide under magnetic stirring, reacting for 5 hours, adding 0.75g of concentrated sulfuric acid and 3.0g of phosphorus pentoxide, and reacting for 5 hours; adding 1.65g of iron powder and 15ml of saturated ammonium chloride solution, heating to 75 ℃, refluxing for 5h, filtering, performing rotary evaporation at 40 ℃, passing through a chromatographic column, collecting the liquid with the darkest color, and performing rotary evaporation to obtain the N- (2, 4-diaminophenyl) maleimide with the yield of 94 percent, wherein the eluent of the chromatographic column is a mixed solution of ethyl acetate and methanol.
EXAMPLE 6 preparation of N- (2, 4-diaminophenyl) maleimide as described in examples 1-3
Adding 7.36g of 2, 4-dinitroaniline into 50ml of N, N-dimethylformamide, dropwise adding a mixed solution of 5.94g of maleic anhydride and 20ml of N, N-dimethylformamide under magnetic stirring, reacting for 5 hours, adding 1.0g of concentrated sulfuric acid and 4.0g of phosphorus pentoxide, and reacting for 5 hours; adding 2.20g of iron powder and 20ml of saturated ammonium chloride solution, heating to 75 ℃, refluxing for 5h, filtering, performing rotary evaporation at 40 ℃, passing through a chromatographic column, collecting the liquid with the darkest color, and performing rotary evaporation to obtain the N- (2, 4-diaminophenyl) maleimide with the yield of 91 percent, wherein the eluent of the chromatographic column is a mixed solution of ethyl acetate and methanol.
Example 6 use of the superhydrophobic maleimide-polyurea porous materials of examples 1-3 for oil-water mixture separation
Dissolving 0.005g of Sudan red III in 50ml of petroleum ether to prepare petroleum ether of Sudan red III; dissolving 0.005g of methyl blue in 50ml of distilled water to prepare a methyl blue aqueous solution; mixing petroleum ether of Sudan red III with methyl blue aqueous solution to obtain oil-water mixture;
filling the super-hydrophobic maleimide polyurea porous material into a chromatographic column to prepare the super-hydrophobic maleimide polyurea porous material chromatographic column;
pouring the oil-water mixture into a super-hydrophobic maleimide polyurea porous material chromatographic column, wherein the oil solution can rapidly pass through the super-hydrophobic maleimide polyurea porous material chromatographic column, and the water solution is retained in the chromatographic column and cannot be filtered out;
pouring an oil-water mixture sample to be separated into a maleimide polyurea porous material chromatographic column, wherein an oil solution can rapidly pass through the super-hydrophobic maleimide polyurea porous material chromatographic column, and an aqueous solution is retained in the chromatographic column and cannot be filtered out;
experimental results show that the super-hydrophobic maleimide polyurea porous material is used for separating oil-water mixtures, and after circulation for ten times, the super-hydrophobic maleimide polyurea porous material still keeps a good separation effect.
Claims (3)
1. The preparation method of the super-hydrophobic maleimide polyurea porous material is characterized by comprising the following preparation steps:
(1) preparation of Maleimide polyurea porous Material
Dissolving 1.0-4.0g of 4.0g N- (2, 4-diaminophenyl) maleimide in 90g of mixed solution of water and acetone with the mass ratio of 3/7, dropwise adding 6-9g of toluene diisocyanate at a constant speed under electric stirring, completing dropping for 30min, heating to 30 ℃, reacting for 2h, centrifuging, and washing with the mixed solution of water and acetone for three times to obtain the maleimide polyurea porous material, wherein the yield is 85-92%;
the maleimide polyurea porous material has the following structural formula:
(2) preparation of super-hydrophobic maleimide polyurea porous material
Dissolving 1.0-2.0g of dodecanethiol in 10ml of ethanol to prepare an ethanol solution of the dodecanethiol;
soaking 0.5-1.0g of the maleimide polyurea porous material in an ethanol solution of dodecyl mercaptan for 5h, filtering and drying at 60 ℃ to obtain the super-hydrophobic maleimide polyurea porous material;
the super-hydrophobic maleimide polyurea porous material is a super-hydrophobic porous material with a water contact angle of 150-155 degrees and an oil contact angle of 0 degrees;
the super-hydrophobic maleimide polyurea porous material 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;
the R is1Is composed of
And
the mass ratio is 8: 2;
the R is2Is composed of
；
The R is3Is composed of
；
The preparation method of the N- (2, 4-diaminophenyl) maleimide comprises the following steps:
adding 3.68-7.36g of 2, 4-dinitroaniline into 50ml of N, N-dimethylformamide, dropwise adding a mixed solution of 2.97-5.94g of maleic anhydride and 20ml of N, N-dimethylformamide under magnetic stirring, reacting for 5 hours, adding 0.5-1.0g of concentrated sulfuric acid and 2.0-4.0g of phosphorus pentoxide, and reacting for 5 hours; adding 1.10-2.20g of iron powder and 10-20ml of saturated ammonium chloride solution, heating to 75 ℃, refluxing for 5h, filtering, performing rotary evaporation at 40 ℃, passing through a chromatographic column, wherein the eluent of the chromatographic column is a mixed solution of ethyl acetate and methanol, collecting the liquid with the deepest color, and performing rotary evaporation to obtain the N- (2, 4-diaminophenyl) maleimide with the yield of 90-94%.
2. The use of the superhydrophobic maleimide polyurea porous material prepared by the preparation method according to claim 1 for oil-water mixture separation.
3. The use of the superhydrophobic maleimide polyurea porous material according to claim 2 for oil-water mixture separation, comprising the steps of:
dissolving 0.005g of Sudan red III in 50ml of petroleum ether to prepare petroleum ether of Sudan red III; dissolving 0.005g of methyl blue in 50ml of distilled water to prepare a methyl blue aqueous solution; mixing petroleum ether of Sudan red III with methyl blue aqueous solution to obtain oil-water mixture;
filling the super-hydrophobic maleimide polyurea porous material into a chromatographic column to prepare the super-hydrophobic maleimide polyurea porous material chromatographic column;
and pouring the oil-water mixture into the super-hydrophobic maleimide polyurea porous material chromatographic column, wherein the oil solution can rapidly pass through the super-hydrophobic maleimide polyurea porous material chromatographic column, and the water solution is retained in the chromatographic column and cannot be filtered out.
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| Diels-Alder-Based Crosslinked Self-Healing Polyurethane/Urea from Polymeric Methylene Diphenyl;Pengfei Du et al.;《JOURNAL OF APPLIED POLYMER SCIENCE》;20140505;第131卷(第9期);第40234（1-7）页 * |
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| 一步法制备聚脲多孔材料及其吸附性能;李树生;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20140615(第6期);第B014-83页 * |
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