CN109824814B - Vegetable oil/inorganic nanoparticle composite super-hydrophobic coating solution and preparation method and application thereof - Google Patents
Vegetable oil/inorganic nanoparticle composite super-hydrophobic coating solution and preparation method and application thereof Download PDFInfo
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Abstract
A vegetable oil/inorganic nano particle composite super-hydrophobic coating solution and a preparation method and application thereof are disclosed, wherein a polyhydroxy structure is introduced into a vegetable oil molecular structure by utilizing a thiol-ene reaction initiated by ultraviolet light, and then vegetable oil-based mercaptan is synthesized through an esterification reaction; uniformly mixing the vegetable oil-based mercaptan, the polyene unsaturated monomer, the inorganic nanoparticles and the photoinitiator, coating the mixture on a base material, and irradiating the base material by ultraviolet light to obtain the super-hydrophobic coating. The raw materials in the invention have wide sources, the cost is low, the preparation process is simple and efficient, the contact angles of the prepared composite coating are all larger than 150 degrees, the excellent super-hydrophobic property and self-cleaning property are displayed, and the composite coating can be applied to the field of oil-water separation.
Description
Technical Field
The invention belongs to the field of chemical engineering and bio-based polymer composite functional materials, relates to a super-hydrophobic coating material, and particularly relates to a vegetable oil/inorganic nanoparticle composite super-hydrophobic coating solution and a preparation method and application thereof.
Background
Wettability is an important characteristic of a solid surface, which is the ability or propensity of a liquid to spread on the solid surface, primarily influenced by the chemical composition or microstructure of the surface. Superhydrophobicity is a particular wettability phenomenon of water droplets on a solid surface. Surfaces with water contact angles greater than 150 ° and rolling angles less than 10 ° are currently referred to as superhydrophobic surfaces. The super-hydrophobic surface attracts attention of researchers due to excellent hydrophobicity, self-cleaning capability and potential application value in the fields of oil-water separation, fluid drag reduction, metal corrosion prevention and the like. According to the super-hydrophobic mechanism of lotus leaves, researchers mainly divide the preparation methods of the super-hydrophobic surface into two types, one is to modify a low-surface-energy substance on a rough solid surface; the other is to build a rough structure on the surface of the hydrophobic material. At present, the method which is applied more is to mix low surface energy polymer and inorganic nano particles together and construct a super-hydrophobic coating on the surface of a base material by spraying, infiltrating or spin coating. But the used low surface energy materials are mainly synthetic materials derived from petrochemical resources and are not renewable; or contains fluorine element, has high cost and is harmful to human body, thereby greatly limiting the practical application of the super-hydrophobic surface in industrial and agricultural production and daily life of people.
The natural vegetable oil is a biomass resource widely existing in nature, and is defined as a mixture of mixed fatty acid triglyceride, wherein each fatty chain contains 14-20 carbon atoms and is a highly hydrophobic substance; the aliphatic chain usually contains various active functional groups such as double bonds, epoxy groups, hydroxyl groups, ester groups and the like, and provides possibility for further functionalization and film-forming crosslinking of the vegetable oil. At present, research on preparation of vegetable oil-based ultraviolet curing coatings by using vegetable oil as a raw material and combining an ultraviolet curing technology with the characteristics of high efficiency, energy conservation, environmental protection and the like becomes a hotspot, and a new way is provided for green and environmental protection in the preparation process of interface materials. However, the combination of vegetable oil and ultraviolet light technology for constructing the super-hydrophobic surface has yet to be further studied. The invention is based on the following.
Disclosure of Invention
The technical problem to be solved is as follows: in order to solve the problems of complex preparation process, harsh process conditions, high raw material price and the like in the preparation of the existing super-hydrophobic material, the invention develops a vegetable oil/inorganic nano particle composite super-hydrophobic coating solution and a preparation method and application thereof by taking renewable biomass resource vegetable oil as a raw material and combining an ultraviolet curing technology, and the solution can be applied to the field of oil-water separation.
The technical scheme is as follows: the preparation method of the vegetable oil/inorganic nano particle composite super-hydrophobic coating solution comprises the following steps: 1) uniformly mixing a bifunctional compound with sulfydryl and hydroxyl, vegetable oil and a photoinitiator, wherein the molar ratio of sulfydryl to unsaturated double bonds in the vegetable oil is (1-10): 1, the mass of the photoinitiator accounts for 1-5% of the mass of the vegetable oil, carrying out sulfydryl-alkene reaction under the irradiation of ultraviolet light, and obtaining vegetable oil polyol after 2-10 hours; uniformly mixing vegetable oil polyalcohol and a bifunctional compound containing sulfydryl and carboxyl, wherein the molar ratio of the carboxyl in the bifunctional compound to the hydroxyl in the vegetable oil polyalcohol is (1-1.5): 1, and carrying out esterification reaction to obtain vegetable oil-based mercaptan; 2) uniformly mixing plant oil-based mercaptan and a polyene unsaturated monomer to prepare reaction resin, wherein the molar ratio of sulfydryl in the plant oil-based mercaptan to double bonds in the polyene unsaturated monomer is 1 (1-1.5); and then adding a photoinitiator accounting for 0.05-3% of the mass fraction of the reaction resin and 1-40% of inorganic nanoparticles, uniformly dispersing, and finally adding tetrahydrofuran for dilution to form a coating solution, wherein the mass ratio of the reaction resin to the tetrahydrofuran is 1: 1-20.
Preferably, the vegetable oil in step 1) is one of soybean oil, castor oil, tung oil, linseed oil, cottonseed oil, sunflower seed oil, rapeseed oil, tea oil, corn oil and olive oil.
Preferably, the bifunctional compound having a thiol group and a hydroxyl group in step 1) is one of 2-mercaptoethanol, 3-thiol-1-propanol, 4-thiol-1-butanol, and 2-thiol-3-butanol.
Preferably, the bifunctional compound having a mercapto group and a carboxyl group in step 2) is one of thioglycolic acid, mercaptopropionic acid, mercaptoundecanoic acid, mercapto-succinic acid, mercaptododecanoic acid, 16-mercapto-hexadecanoic acid, 2-mercapto-4-methyl-5-thiazoleacetic acid, 2, 3, 5, 6-tetrafluoro-4-mercaptobenzoic acid, 3-mercaptoisobutyric acid, and thiosalicylic acid.
Preferably, the polyenylunsaturated monomer in step 2) is at least one or two of trivinyl POSS, octavinyl POSS, 2,4,6, 8-tetramethyl-2, 4,6, 8-tetravinylcyclotetrasiloxane, triallyl isocyanurate, triallyl (methyl) silane, triallyl (phenyl) silane, myrcene, triallyl isocyanurate and vinyl-terminated polydimethylsiloxane.
Preferably, the photoinitiator in the step 2) is one of 2-hydroxy-2-methyl-1-phenyl acetone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-acetone and 2-dimethylamino-2-benzyl-1- [4- (4-morpholinyl) phenyl ] -1-butanone.
Preferably, the inorganic nanoparticles in the step 2) are at least one of silicon dioxide, ferroferric oxide, titanium dioxide, aluminum oxide, calcium carbonate, gold and silver with the particle size of 1-500 nm.
The vegetable oil/inorganic nano particle composite super-hydrophobic coating solution obtained by the method.
The application of the coating solution is to coat the coating solution on a base material in a dipping, spin coating or spraying mode, and then place the base material under ultraviolet light for irradiating for 5-30 seconds to obtain the super-hydrophobic coating.
The super-hydrophobic coating is applied to oil-water separation.
Has the advantages that: the super-hydrophobic coating is constructed by renewable vegetable oil and inorganic nano particles, has the advantages of wide raw material source, low cost, no need of using harmful fluorine-containing substances and the like, and has stable super-hydrophobic performance. According to the invention, through sulfhydrylation modification of the vegetable oil, the vegetable oil can be crosslinked with the polyenylunsaturated monomer to form a film through sulfhydrylation-alkene click reaction initiated by ultraviolet light, and the preparation method has the characteristics of high reaction speed, simplicity and easiness in scale production, truly realizes double greenness of raw materials and curing technology in the preparation process of the super-hydrophobic material, and is beneficial to promotion of popularization and application of the super-hydrophobic coating in actual life.
Drawings
FIG. 1 is a process diagram of separating oil and water mixture of cotton cloth modified by the super-hydrophobic coating prepared in example 4. The oil-water mixture was a mixture of chloroform and water, poured red liquid dyed chloroform, and super-hydrophobic cotton cloth soaked in blue dyed deionized water. As can be seen from the figure, the red chloroform can smoothly pass through the super-hydrophobic cotton cloth, water is trapped on the surface of the cotton cloth, and the oil-water separation efficiency reaches 99.99%.
Detailed Description
Example 1
1) Preparation of tung oil-based mercaptan: uniformly mixing 7.8g of 2-mercaptoethanol and 11g of tung oil, adding 0.22g of initiator 2-hydroxy-2-methyl-1-phenyl acetone, uniformly mixing, and reacting for 6 hours under the irradiation of ultraviolet light to obtain tung oil polyol; dispersing 10.5g of tung oil polyalcohol and 6.3g of mercaptopropionic acid in 100 mL of toluene, uniformly stirring, reacting for 6h at 110 ℃ under the action of 0.34 g of p-toluenesulfonic acid, finally dispersing the product in 100 mL of ethyl acetate, and removing the solvent through water washing and rotary evaporation to obtain tung oil-based mercaptan;
2) uniformly mixing 1g of tung oil-based mercaptan and 0.5g of octavinyl POSS, adding 3 mg of 2-hydroxy-2-methyl-1-phenyl acetone, uniformly dispersing, and finally adding 15mL of tetrahydrofuran for dilution to form a coating solution;
3) the coating solution was applied by spraying onto glass slides, cotton cloth, metal mesh, filter paper and wood, followed by exposure to ultraviolet light for 5min to give hydrophobic coatings with contact angles of 135 °, 145 °, 152 °, 148 ° and 150 °.
4) The cotton cloth modified by the coating is used for carrying out an oil-water separation test, chloroform/water mixed liquor (V/V =1: 1) is separated, the hydrophobic cotton cloth can effectively intercept water and allow an oil phase to pass through, so that the effect of oil-water separation is achieved, and the separation efficiency is 98.8%.
Example 2
1) Preparation of tung oil-based mercaptan: uniformly mixing 7.8g of 2-mercaptoethanol and 11g of tung oil, adding 0.22g of initiator 2-hydroxy-2-methyl-1-phenyl acetone, uniformly mixing, and reacting for 6 hours under the irradiation of ultraviolet light to obtain tung oil polyol; dispersing 10.5g of tung oil polyalcohol and 6.3g of mercaptopropionic acid in 100 mL of toluene, uniformly stirring, reacting for 6h at 110 ℃ under the action of 0.34 g of p-toluenesulfonic acid, finally dispersing the product in 100 mL of ethyl acetate, and removing the solvent through water washing and rotary evaporation to obtain tung oil-based mercaptan;
2) 1g of tung oil based mercaptan and 0.5g of octavinyl POSS were mixed well and 3 mg of 2-hydroxy-2-methyl-1-phenylpropanone and 0.15g of SiO2Dispersing nano particles uniformly, and finally adding 15mL of tetrahydrofuran for dilution to form a coating solution;
3) the coating solution was applied by spraying onto glass slides, cotton cloth, metal mesh, filter paper and wood, followed by exposure to ultraviolet light for 5min to give hydrophobic coatings with contact angles of 148 °, 160 °, 162 °, 164 ° and 161 °.
4) The cotton cloth coated with the coating is used for oil-water separation test, chloroform/water mixed liquor (V/V =1: 1) is separated, the super-hydrophobic cotton cloth can effectively intercept water and allow oil phase to pass through, so that the oil-water separation effect is achieved, and the separation efficiency is 99.99%.
Example 3
1) Preparation of tung oil-based mercaptan: uniformly mixing 7.8g of 2-mercaptoethanol and 11g of tung oil, adding 0.22g of initiator 2-hydroxy-2-methyl-1-phenyl acetone, uniformly mixing, and reacting for 6 hours under the irradiation of ultraviolet light to obtain tung oil polyol; dispersing 10.5g of tung oil polyalcohol and 6.3g of mercaptopropionic acid in 100 mL of toluene, uniformly stirring, reacting for 6h at 110 ℃ under the action of 0.34 g of p-toluenesulfonic acid, finally dispersing the product in 100 mL of ethyl acetate, and removing the solvent through water washing and rotary evaporation to obtain tung oil-based mercaptan;
2) 1g of tung oil based mercaptan and 0.5g of octavinyl POSS were mixed well and 3 mg of 2-hydroxy-2-methyl-1-phenylpropanone and 0.3 g of SiO2Dispersing nano particles uniformly, and finally adding 15mL of tetrahydrofuran for dilution to form a coating solution;
3) the coating solution was applied by spraying onto glass slides, cotton cloth, metal mesh, filter paper and wood, followed by exposure to ultraviolet light for 5min to give hydrophobic coatings with contact angles of 155 °, 164 °, 165 °, 165 ° and 163 °.
4) The cotton cloth coated with the coating is used for oil-water separation test, chloroform/water mixed liquor (V/V =1: 1) is separated, the super-hydrophobic cotton cloth can effectively intercept water and allow oil phase to pass through, so that the oil-water separation effect is achieved, and the separation efficiency is 99.99%.
Example 4
1) Preparation of tung oil-based mercaptan: uniformly mixing 7.8g of 2-mercaptoethanol and 11g of tung oil, adding 0.22g of initiator 2-hydroxy-2-methyl-1-phenyl acetone, uniformly mixing, and reacting for 6 hours under the irradiation of ultraviolet light to obtain tung oil polyol; dispersing 10.5g of tung oil polyalcohol and 6.3g of mercaptopropionic acid in 100 mL of toluene, uniformly stirring, reacting for 6h at 110 ℃ under the action of 0.34 g of p-toluenesulfonic acid, finally dispersing the product in 100 mL of ethyl acetate, and removing the solvent through water washing and rotary evaporation to obtain tung oil-based mercaptan;
2) 1g of tung oil based mercaptan and 0.5g of octavinyl POSS were mixed well and 3 mg of 2-hydroxy-2-methyl-1-phenylpropanone and 0.45g of SiO2Dispersing nano particles uniformly, and finally adding 15mL of tetrahydrofuran for dilution to form a coating solution;
3) the coating solution was applied by spraying onto glass slides, cotton cloth, metal mesh, filter paper and wood, followed by exposure to uv light for 5min to give hydrophobic coatings with contact angles of 158 °, 170 °, 172 °, 172 ° and 173 °.
4) The cotton cloth coated with the coating is used for oil-water separation test, chloroform/water mixed liquor (V/V =1: 1) is separated, the super-hydrophobic cotton cloth can effectively intercept water and allow oil phase to pass through, so that the oil-water separation effect is achieved, and the separation efficiency is 99.99%.
Example 5
1) Preparation of castor oil based mercaptan: uniformly mixing 7.8g of 2-mercaptoethanol and 9.3g of castor oil, adding 0.22g of initiator 2-hydroxy-2-methyl-1-phenyl acetone, uniformly mixing, and reacting for 6 hours under the irradiation of ultraviolet light to obtain castor oil polyol; dispersing 9g of castor oil polyol and 5.4g of mercaptopropionic acid in 100 mL of toluene, uniformly stirring, reacting for 6h at 110 ℃ under the action of 0.29 g of p-toluenesulfonic acid, finally dispersing the product in 100 mL of ethyl acetate, and removing the solvent through water washing and rotary evaporation to obtain castor oil-based mercaptan;
2) 1g castor oil based thiol and 0.3 g octavinyl POSS were mixed well and 2.6 mg of 2-hydroxy-2-methyl-1-phenyl acetone and 0.39g of SiO2Dispersing nano particles uniformly, and finally adding 15mL of tetrahydrofuran for dilution to form a coating solution;
3) the coating solution was applied by spraying onto glass slides, cotton cloth, metal mesh, filter paper and wood, followed by exposure to ultraviolet light for 5min to give a hydrophobic coating with contact angles of 158 °, 165 °, 166 °, 163 ° and 161 °.
4) The cotton cloth coated with the coating is used for oil-water separation test, chloroform/water mixed liquor (V/V =1: 1) is separated, the super-hydrophobic cotton cloth can effectively intercept water and allow oil phase to pass through, so that the oil-water separation effect is achieved, and the separation efficiency is 99.95%.
Example 6
1) Preparation of soybean oil-based mercaptan: mixing 7.8g of 2-mercaptoethanol and 9.3g of soybean oil uniformly, adding 0.22g of initiator 2-hydroxy-2-methyl-1-phenyl acetone, mixing uniformly, and reacting for 6 hours under the irradiation of ultraviolet light to obtain soybean oil polyol; dispersing 9g of soybean oil polyol and 4.5g of mercaptopropionic acid in 100 mL of toluene, uniformly stirring, reacting for 6h at 110 ℃ under the action of 0.27 g of p-toluenesulfonic acid, finally dispersing the product in 100 mL of ethyl acetate, and removing the solvent through water washing and rotary evaporation to obtain soybean oil-based mercaptan;
2) 1g of soybean oil based thiol and 0.28 g of octavinyl POSS were mixed well and 2.5 mg of 2-hydroxy-2-methyl-1-phenylpropanone and 0.384g of SiO2Dispersing nano particles uniformly, and finally adding 15mL of tetrahydrofuran for dilution to form a coating solution;
3) the coating solution was applied by spraying onto glass slides, cotton cloth, metal mesh, filter paper and wood, followed by exposure to ultraviolet light for 5min to give hydrophobic coatings with contact angles of 159 °, 164 °, 164 °, 162 ° and 162 °.
4) The cotton cloth coated with the coating is used for oil-water separation test, chloroform/water mixed liquor (V/V =1: 1) is separated, the super-hydrophobic cotton cloth can effectively intercept water and allow oil phase to pass through, so that the oil-water separation effect is achieved, and the separation efficiency is 99.98%.
Claims (7)
1. The preparation method of the vegetable oil/inorganic nanoparticle composite super-hydrophobic coating solution is characterized by comprising the following steps of: 1) uniformly mixing a bifunctional compound with sulfydryl and hydroxyl, vegetable oil and a photoinitiator, wherein the vegetable oil is soybean oil, castor oil or tung oil, the molar ratio of sulfydryl to unsaturated double bonds in the vegetable oil is (1-10) to 1, the mass of the photoinitiator accounts for 1-5% of the mass of the vegetable oil, carrying out sulfydryl-alkene reaction under the irradiation of ultraviolet light, and obtaining vegetable oil polyol after 2-10 hours; uniformly mixing vegetable oil polyalcohol and a bifunctional compound containing sulfydryl and carboxyl, wherein the molar ratio of the carboxyl in the bifunctional compound to the hydroxyl in the vegetable oil polyalcohol is (1-1.5): 1, and carrying out esterification reaction to obtain vegetable oil-based mercaptan; 2) uniformly mixing plant oil-based mercaptan and octavinyl POSS to prepare reaction resin, wherein the molar ratio of sulfydryl in the plant oil-based mercaptan to double bonds in the octavinyl POSS is 1 (1-1.5); and then adding a photoinitiator accounting for 0.05-3% of the mass fraction of the reaction resin and 1-40% of silicon dioxide, uniformly dispersing, and finally adding tetrahydrofuran for dilution to form a coating solution, wherein the mass ratio of the reaction resin to the tetrahydrofuran is 1: 1-20.
2. The method for preparing the vegetable oil/inorganic nanoparticle composite superhydrophobic coating solution according to claim 1, wherein the bifunctional compound having thiol and hydroxyl groups in step 1) is one of 2-mercaptoethanol, 3-thiol-1-propanol, 4-thiol-1-butanol, and 2-thiol-3-butanol.
3. The method for preparing the vegetable oil/inorganic nanoparticle composite superhydrophobic coating solution according to claim 1, wherein the bifunctional compound having a thiol group and a carboxyl group in the step 2) is one of thioglycolic acid, mercaptopropionic acid, mercaptoundecanoic acid, mercapto-succinic acid, mercaptododecanoic acid, 16-mercapto-hexadecanoic acid, 2-mercapto-4-methyl-5-thiazoleacetic acid, 2, 3, 5, 6-tetrafluoro-4-mercaptobenzoic acid, 3-mercaptoisobutyric acid, and thiosalicylic acid.
4. The method for preparing the vegetable oil/inorganic nanoparticle composite superhydrophobic coating solution according to claim 1, wherein the photoinitiator in the step 2) is one of 2-hydroxy-2-methyl-1-phenyl acetone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-propanone, and 2-dimethylamino-2-benzyl-1- [4- (4-morpholinyl) phenyl ] -1-butanone.
5. The vegetable oil/inorganic nano particle composite super-hydrophobic coating solution obtained by the method of any one of claims 1 to 4.
6. The application of the coating solution according to claim 5, wherein the coating solution is coated on a substrate by dipping, spin coating or spray coating, and then the substrate is irradiated under ultraviolet light for 5-30 seconds to obtain the super-hydrophobic coating.
7. Use of the superhydrophobic coating of claim 6 in oil-water separation.
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| CN115928501B (en) * | 2022-12-08 | 2023-09-15 | 黄山金仕特种包装材料有限公司 | Antibacterial packaging paper and preparation method thereof |
| CN116693802B (en) * | 2023-08-04 | 2023-10-13 | 张家港市顾乐仕生活家居科技有限公司 | Bio-based polyurethane buffer material |
| CN117903394B (en) * | 2024-03-20 | 2024-06-18 | 江苏瑞洋安泰新材料科技有限公司 | Bio-based isocyanate crosslinking agent and preparation process thereof |
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