CN109675444B - Preparation method of tannic acid modified underwater super-oleophobic oil-water separation net film - Google Patents
Preparation method of tannic acid modified underwater super-oleophobic oil-water separation net film Download PDFInfo
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Abstract
The invention discloses a preparation method of an underwater super-oleophobic oil-water separation net film based on tannic acid modification. The preparation method is characterized in that tannic acid is used for carrying out surface modification on a net membrane material, and then bionic zwitterionic compound substances are connected to the surface of the net membrane material through reaction of the tannic acid with a catechol group and a derivative group of the tannic acid, so that the super-hydrophilic/underwater super-oleophobic oil-water separation net membrane is prepared. The raw materials of the invention are easy to obtain and have wide sources. The prepared super-hydrophobic and super-oleophylic oil-water separation mesh membrane has better selective permeation on water, low treatment cost, simple and convenient operation and can be recycled for multiple times.
Description
Technical Field
The invention relates to a preparation method of an oil-water separation net film, in particular to a preparation method of an underwater super-oleophobic oil-water separation net film based on tannic acid modification.
Background
With the discharge of large amounts of oily sewage in production and life and the frequent occurrence of accidents of crude oil leakage at sea, oil pollution in water has become a significant problem to the health of human beings and to the environmental safety. In order to maintain good ecological environment and human health and protect limited water resources, effective separation of oily sewage becomes an urgent problem to be solved. At present, a plurality of methods for treating water pollution caused by toxic organic solvents or petroleum product leakage exist, and the traditional oil-water separation method comprises gravity separation, oil skimming, centrifugation, flotation and the like, has a good effect on oil-water separation, but can be limited to the problems of low separation efficiency, high energy consumption, complex process, easy secondary pollution and the like. In recent years, with the rapid development of nanotechnology and bionic science, people have systematic understanding on the relation between the microstructure of the solid surface and wettability, and functional materials based on the super-wetting property indicate a new direction and a solution for oil-water separation. The separating material based on the characteristic of super-wetting can effectively and selectively separate oil and water, and the purpose of oil-water separation is realized.
At present, an oil-water separation mesh membrane with super-hydrophilic/underwater super-oleophobic characteristics has been reported in the field of oil-water separation, and the oil-water separation mesh membrane with super-hydrophilic/underwater super-oleophobic characteristics can effectively realize the oil-water separation effect of 'water interception oil'. The bionic cell membrane-based zwitterionic material has better hydrophilic and oleophobic properties and better stain resistance under water, and is gradually paid attention to by researchers. In recent years, biomimetic mussel chemistry represented by oxidative auto-polymerization of dopamine has injected great vigor for the development of material surface interface science and technology, and is widely researched and used for material surface interface modification and functionalization. In the field of oil-water separation materials, some documents and patent reports exist for a super-hydrophilic/underwater super-oleophobic bionic functional surface based on dopamine surface modification, but the preparation process is still complicated, the cost is high, and the method is not suitable for industrial production and application.
Disclosure of Invention
The invention aims to overcome the defects and shortcomings of the prior art, further improves the surface modification of materials, and provides a method for preparing a super-hydrophilic/underwater super-oleophobic oil-water separation net film based on tannic acid modification. The preparation method comprises the steps of carrying out appropriate surface pretreatment modification on the surface of a net membrane material by adopting a natural polyphenol substance (tannic acid) and retaining the reaction activity, and further connecting bionic zwitterionic compound substances on the surface of the net membrane material by means of non-covalent action or covalent bond reaction and the like, such as hydrogen bond action, electrostatic action, reaction between catechol groups and derivative groups thereof and other groups (amino groups and the like), so that the preparation of the super-hydrophilic/underwater super-oleophobic oil-water separation net membrane is realized.
The purpose of the invention is realized by the following technical scheme:
a preparation method of an underwater super-oleophobic oil-water separation net film based on tannic acid modification comprises the following steps:
(1) cleaning the fabric net and then airing for later use;
(2) dissolving tannic acid in a solvent A, and adjusting the pH value to 7.1-9.0 to obtain a tannic acid solution; in the tannic acid solution, the mass percentage of tannic acid is 0.1-20%;
dissolving ferric chloride in a solvent A to obtain an iron ion solution; in the iron ion solution, the mass percentage of iron ions is 0.01-10%;
dissolving N, N-dimethyl-1, 3-diaminopropane in a solvent A to obtain a tertiary amine modified solution; in the tertiary amine modified solution, the mass percentage of N-dimethyl-1, 3-diaminopropane is 0.01-20%;
dissolving a quaternization reagent in a solvent A to obtain a zwitterionic modified solution; in the zwitterionic modification solution, the mass percentage of the quaternary amination reagent is 0.01-20%;
wherein the solvent A is at least one of water, ethanol, methanol, isopropanol and n-butanol; the quaternization reagent is at least one of 1, 3-propane sultone, 1, 4-butane sultone, beta-propane lactone, gamma-butyrolactone and acrylic acid;
(3) soaking the dried fabric net in a tannic acid solution for 1 second to 24 hours, and taking out and drying the fabric net; then soaking the iron ions in an iron ion solution for 1 second to 1 hour, and taking out and airing; this process was repeated at least 1 time; taking out and drying in a drying oven at 50-100 ℃ for 0.5-12 hours to obtain the tannin modified fabric net;
(4) and (3) soaking the tannic acid modified fabric net obtained in the step (3) in a tertiary amine modified solution, reacting for 1-48 hours at the temperature of 30-80 ℃, taking out, and drying in a drying oven at the temperature of 50-100 ℃ for 0.5-6 hours to obtain the oil-water separation net membrane with the surface subjected to tertiary amination modification.
(5) And (3) soaking the oil-water separation net membrane with the surface subjected to tertiary amination modification in the step (4) in an amphoteric ionization modification solution, reacting for 1-24 hours at 20-60 ℃, taking out, and drying in a drying oven at 40-90 ℃ for 0.5-12 hours to obtain the tannin-modified underwater super-oleophobic oil-water separation net membrane.
Further, the fabric net is a metal fabric net or a non-woven fabric net; the metal fabric net is at least one of a stainless steel net, a copper net, an iron net and an aluminum alloy net; the non-woven fabric net is at least one of a PET non-woven fabric net, a PP non-woven fabric net and a nylon non-woven fabric net;
furthermore, the mesh number of the fabric net is 30-400 meshes;
further, the tannic acid modified underwater super-oleophobic oil-water separation mesh membrane is applied to oil-water separation.
Compared with the prior art, the invention has the following advantages and beneficial effects:
1. according to the invention, tannic acid is used for surface modification of the net membrane material, and then a bionic zwitterionic compound substance is connected to the surface of the net membrane material through reaction with a catechol group of tannic acid and a derivative group of the tannic acid, so that the preparation of the super-hydrophilic/underwater super-oleophobic oil-water separation net membrane is realized.
2. The raw materials of the invention are easy to obtain and have wide sources.
3. The prepared super-hydrophobic and super-oleophylic oil-water separation mesh membrane has better selective permeation on water, low treatment cost, simple and convenient operation and can be recycled for multiple times.
Drawings
FIG. 1 is a schematic illustration of the process for making the oil-water separation omentum of example 1.
Fig. 2 is a photograph of the water contact angle of the oil-water separation mesh film prepared in example 1.
FIG. 3 is a SEM image of the oil-water separation mesh film prepared in example 1.
FIG. 4 is a schematic view showing the effect of oil-water separation of the oil-water separation mesh membrane in example 1.
Detailed Description
The following describes in detail embodiments of the present invention with reference to the drawings and examples, but the embodiments of the present invention are not limited thereto.
Example 1
(1) And cleaning the stainless steel mesh with 400 meshes, and airing for later use.
(2) Dissolving tannic acid in water, and adjusting the pH to 8.3 to obtain a tannic acid solution with the tannic acid content of 3% by mass; dissolving ferric chloride in water to obtain an iron ion solution with the mass percentage of iron ions being 1%; dissolving N, N-dimethyl-1, 3-diaminopropane in water to obtain a tertiary amine modified solution with the mass percentage of the N-dimethyl-1, 3-diaminopropane of 5%; dissolving 1, 3-propane sultone in methanol to obtain a zwitterionic modified solution with the mass percentage of 1, 3-propane sultone of 2%.
(3) Soaking the dried stainless steel mesh in a tannic acid solution for 10 seconds, and taking out and drying; then soaking in iron ion solution for 5 seconds, taking out and airing; this process was repeated 6 times; taking out and drying in a drying oven at 80 ℃ for 6 hours to obtain the tannin modified fabric net;
(4) and (4) soaking the tannic acid modified fabric net obtained in the step (3) in a tertiary amine modified solution, reacting for 8 hours at the temperature of 60 ℃, taking out, and drying for 06 hours in a drying oven at the temperature of 80 ℃ to obtain the oil-water separation net film with the surface subjected to tertiary amination modification.
(5) And (3) soaking the oil-water separation mesh membrane with the surface subjected to tertiary amination modification in the step (4) in an amphoteric ionization modification solution, reacting for 24 hours at 40 ℃, taking out, and drying for 5 hours in a drying oven at 50 ℃ to obtain the tannin-modified underwater super-oleophobic oil-water separation mesh membrane.
FIG. 1 is a schematic diagram of the process for preparing the oil-water separation mesh membrane of this example. Fig. 2 is a photograph of an underwater oil drop (n-hexane) contact angle of the oil-water separation mesh membrane prepared in this embodiment, and it can be seen from the photograph that the prepared oil-water separation mesh membrane has a better underwater super-oleophobic property. Fig. 3 is a SEM image of the oil-water separation mesh film prepared in this example. FIG. 4 is a schematic diagram of oil-water separation effect of the oil-water separation mesh membrane in this embodiment, and in the embodiment, an oil-water separation experiment is performed by using an oil-water mixture of n-hexane and water, and it can be seen from the diagram that water can selectively pass through, and n-hexane is trapped on the oil-water separation mesh membrane, so that a better oil-water separation effect is shown; after the oil-water separation experiment is repeated for 50 times, the oil-water separation net film still keeps excellent oil-water separation effect.
Example 2
(1) And cleaning the stainless steel mesh with 300 meshes, and airing for later use.
(2) Dissolving tannic acid in water, and adjusting the pH to 8 to obtain a tannic acid solution with the tannic acid content of 4% by mass; dissolving ferric chloride in water to obtain an iron ion solution with the mass percentage of iron ions of 0.5%; dissolving N, N-dimethyl-1, 3-diaminopropane in ethanol to obtain a tertiary amine modified solution with the mass percentage of 2% of N-dimethyl-1, 3-diaminopropane; dissolving 1, 3-propane sultone in ethanol to obtain a zwitterionic modified solution with the mass percentage of 1, 3-propane sultone of 2%.
(3) Soaking the dried stainless steel mesh in a tannic acid solution for 1 hour, and taking out and drying; then soaking in iron ion solution for 20 seconds, taking out and airing; this process was repeated 4 times; taking out and drying in a drying oven at 60 ℃ for 6 hours to obtain the tannin modified fabric net;
(4) and (4) soaking the tannic acid modified fabric net obtained in the step (3) in a tertiary amine modified solution, reacting for 38 hours at the temperature of 60 ℃, taking out, and drying for 6 hours in a drying oven at the temperature of 50 ℃ to obtain the oil-water separation net film with the surface subjected to tertiary amination modification.
(5) And (3) soaking the oil-water separation mesh membrane with the surface subjected to tertiary amination modification in the step (4) in an amphoteric ionization modification solution, reacting for 24 hours at the temperature of 60 ℃, taking out, and drying in a drying oven at the temperature of 40 ℃ for 6 hours to obtain the tannin-modified underwater super-oleophobic oil-water separation mesh membrane.
Example 3
(1) And cleaning a 100-mesh copper net, and then airing for later use.
(2) Dissolving tannic acid in ethanol, and adjusting pH to 9.0 to obtain a tannic acid solution with tannic acid content of 0.1 wt%; dissolving ferric chloride in ethanol to obtain an iron ion solution with the mass percentage of iron ions of 0.01 percent; dissolving N, N-dimethyl-1, 3-diaminopropane in ethanol to obtain a tertiary amine modified solution with the mass percentage of N-dimethyl-1, 3-diaminopropane of 0.01%; dissolving gamma-butyrolactone in ethanol to obtain an amphoteric ionized modified solution with the gamma-butyrolactone content of 0.01% by mass.
(3) Soaking the dried copper mesh in a tannic acid solution for 30 seconds, and taking out and drying; then soaking in iron ion solution for 30 seconds, taking out and airing; this process was repeated 15 times; taking out and drying in a drying oven at 50 ℃ for 0.5 hour to obtain the tannin modified fabric net;
(4) and (4) soaking the tannic acid modified fabric net obtained in the step (3) in a tertiary amine modified solution, reacting for 1 hour at the temperature of 30 ℃, taking out, and drying for 0.5 hour in a drying oven at the temperature of 50 ℃ to obtain the oil-water separation net film with the surface subjected to tertiary amination modification.
Example 4
(1) And cleaning the 200-mesh PET non-woven fabric net, and then airing for later use.
(2) Dissolving tannic acid in water, and adjusting the pH to 9.0 to obtain a tannic acid solution with the tannic acid content of 20% by mass; dissolving ferric chloride in water to obtain an iron ion solution with the mass percentage of iron ions of 10%; dissolving N, N-dimethyl-1, 3-diaminopropane in ethanol to obtain a tertiary amine modified solution with the mass percentage of the N-dimethyl-1, 3-diaminopropane of 20%; dissolving acrylic acid in methanol to obtain the amphoteric ionized modified solution with the mass percentage of acrylic acid of 20%.
(3) Soaking the dried PET non-woven fabric net in a tannic acid solution for 1 second, and taking out and drying; then soaking in iron ion solution for 1 second, taking out and drying; this process was repeated 1 time; taking out and drying in a drying oven at 50 ℃ for 0.5 hour to obtain the tannin modified fabric net;
(4) and (4) soaking the tannic acid modified fabric net obtained in the step (3) in a tertiary amine modified solution, reacting for 1 hour at the temperature of 30 ℃, taking out, and drying for 0.5 hour in a drying oven at the temperature of 50 ℃ to obtain the oil-water separation net film with the surface subjected to tertiary amination modification.
(5) And (3) soaking the oil-water separation mesh membrane with the surface subjected to tertiary amination modification in the step (4) in an amphoteric ionization modification solution, reacting for 1 hour at 20 ℃, taking out, and drying in a drying oven at 40 ℃ for 0.5 hour to obtain the tannin-modified underwater super-oleophobic oil-water separation mesh membrane.
Example 5
(1) And cleaning the PP non-woven fabric net with 30-400 meshes, and airing for later use.
(2) Dissolving tannic acid in water, and adjusting pH to 7.1 to obtain tannic acid solution with tannic acid content of 0.1 wt%; dissolving ferric chloride in water to obtain an iron ion solution with the mass percentage of iron ions of 0.01 percent; dissolving N, N-dimethyl-1, 3-diaminopropane in methanol to obtain a tertiary amine modified solution with the mass percentage of the N-dimethyl-1, 3-diaminopropane of 0.01%; dissolving 1, 3-propane sultone in isopropanol to obtain 0.01 mass percent of 1, 3-propane sultone-containing zwitterionic modified solution.
(3) Soaking the dried PP non-woven fabric net in a tannic acid solution for 1 second, and taking out and drying; then soaking in iron ion solution for 1 second, taking out and drying; this process was repeated 20 times; taking out and drying in a drying oven at 100 ℃ for 12 hours to obtain the tannin modified fabric net;
(4) and (4) soaking the tannic acid modified fabric net obtained in the step (3) in a tertiary amine modified solution, reacting for 48 hours at the temperature of 80 ℃, taking out, and drying for 6 hours in a drying oven at the temperature of 100 ℃ to obtain the oil-water separation net film with the surface subjected to tertiary amination modification.
(5) And (3) soaking the oil-water separation mesh membrane with the surface subjected to tertiary amination modification in the step (4) in an amphoteric ionization modification solution, reacting for 24 hours at the temperature of 60 ℃, taking out, and drying in a drying oven at the temperature of 90 ℃ for 12 hours to obtain the tannin-modified underwater super-oleophobic oil-water separation mesh membrane.
Example 6
(1) And cleaning the 30-mesh stainless steel net and then airing for later use.
(2) Dissolving tannic acid in ethanol, and adjusting the pH to 8.0 to obtain a tannic acid solution with the tannic acid content of 2% by mass; dissolving ferric chloride in methanol to obtain an iron ion solution with the mass percentage of iron ions of 1%; dissolving N, N-dimethyl-1, 3-diaminopropane in water to obtain a tertiary amine modified solution with the mass percentage of 2% of N-dimethyl-1, 3-diaminopropane; dissolving 1, 3-propane sultone in n-butyl alcohol to obtain an amphoteric ionized modified solution with the mass percentage of 1, 3-propane sultone of 2%.
(3) Soaking the dried stainless steel mesh in a tannic acid solution for 90 seconds, and taking out and drying; then soaking in iron ion solution for 5 seconds, taking out and airing; this process was repeated 5 times; taking out and drying in a drying oven at 80 ℃ for 5 hours to obtain the tannin modified fabric net;
(4) and (4) soaking the tannic acid modified fabric net obtained in the step (3) in a tertiary amine modified solution, reacting for 4 hours at the temperature of 60 ℃, taking out, and drying for 5 hours in a drying oven at the temperature of 60 ℃ to obtain the oil-water separation net film with the surface subjected to tertiary amination modification.
(5) And (3) soaking the oil-water separation mesh membrane with the surface subjected to tertiary amination modification in the step (4) in an amphoteric ionization modification solution, reacting for 24 hours at 4 ℃, taking out, and drying for 4 hours in a drying oven at 60 ℃ to obtain the tannin-modified underwater super-oleophobic oil-water separation mesh membrane.
Claims (3)
1. A preparation method of an underwater super-oleophobic oil-water separation net film based on tannic acid modification is characterized by comprising the following steps:
(1) cleaning the fabric net and then airing for later use;
(2) dissolving tannic acid in a solvent A, and adjusting the pH value to 7.1-9.0 to obtain a tannic acid solution; in the tannic acid solution, the mass percentage of tannic acid is 0.1-20%;
dissolving ferric chloride in a solvent A to obtain an iron ion solution; in the iron ion solution, the mass percentage of iron ions is 0.01-10%;
dissolving N, N-dimethyl-1, 3-diaminopropane in a solvent A to obtain a tertiary amine modified solution; in the tertiary amine modified solution, the mass percentage of N, N-dimethyl-1, 3-diaminopropane is 0.01-20%;
dissolving a quaternization reagent in a solvent A to obtain a zwitterionic modified solution; in the zwitterionic modification solution, the mass percentage of the quaternary amination reagent is 0.01-20%;
wherein the solvent A is at least one of water, ethanol, methanol, isopropanol and n-butanol; the quaternization reagent is at least one of 1, 3-propane sultone, 1, 4-butane sultone, beta-propane lactone, gamma-butyrolactone and acrylic acid;
(3) soaking the dried fabric net in a tannic acid solution for 1 second to 24 hours, and taking out and drying the fabric net; then soaking the mixture in iron ion solution for 1 second to 1 hour, and taking out and drying the mixture; this process was repeated at least 1 time; taking out and drying in a drying oven at 50-100 ℃ for 0.5-12 hours to obtain the tannin modified fabric net;
(4) soaking the tannic acid modified fabric net obtained in the step (3) in a tertiary amine modified solution, reacting for 1-48 hours at 30-80 ℃, taking out, and drying in a drying oven at 50-100 ℃ for 0.5-6 hours to obtain an oil-water separation net membrane with the surface subjected to tertiary amination modification;
(5) and (3) soaking the oil-water separation net membrane with the surface subjected to tertiary amination modification in the step (4) in an amphoteric ionization modification solution, reacting for 1-24 hours at 20-60 ℃, taking out, and drying in a drying oven at 40-90 ℃ for 0.5-12 hours to obtain the tannin-modified underwater super-oleophobic oil-water separation net membrane.
2. The method of claim 1, wherein:
the fabric net is a metal fabric net or a non-woven fabric net; the metal fabric net is at least one of a stainless steel net, a copper net, an iron net and an aluminum alloy net; the non-woven fabric net is at least one of a PET non-woven fabric net, a PP non-woven fabric net and a nylon non-woven fabric net;
the mesh number of the fabric net is 30-400 meshes.
3. The application of the oil-water separation membrane prepared by the preparation method of the tannic acid modified underwater super-oleophobic oil-water separation mesh membrane in oil-water separation is disclosed in claim 1 or 2.
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| CN113019145B (en) * | 2021-04-03 | 2022-03-22 | 浙江海洋大学 | Preparation method of super-wetting oil-water separation membrane |
| CN115445246B (en) * | 2022-08-24 | 2023-10-20 | 电子科技大学 | High-performance surface-modified oil-water separation membrane and preparation method and application thereof |
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