CN111229190A - Preparation method of super-hydrophobic oil-water separation material based on plant polyphenol-amino silicone oil modification - Google Patents
Preparation method of super-hydrophobic oil-water separation material based on plant polyphenol-amino silicone oil modification Download PDFInfo
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- CN111229190A CN111229190A CN202010156515.6A CN202010156515A CN111229190A CN 111229190 A CN111229190 A CN 111229190A CN 202010156515 A CN202010156515 A CN 202010156515A CN 111229190 A CN111229190 A CN 111229190A
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- oil
- amino silicone
- water separation
- silicone oil
- water
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- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—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 form
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Abstract
The invention discloses a preparation method of a super-hydrophobic oil-water separation material based on plant polyphenol-amino silicone oil modification, which is prepared by utilizing the reaction between catechol groups of natural polyphenol substances and derivative groups thereof and groups (amino groups and the like) of amino silicone oil. The method adopts aqueous solution to carry out reaction in the whole process, and has the characteristics of low cost, no pollution, simple preparation process, wide raw material source and the like; the prepared super-hydrophobic oil-water separation material has better separation capability on oil substances, and has the advantages of low treatment cost, simple and convenient operation and cyclic use for many times.
Description
Technical Field
The invention relates to a preparation method of an oil-water separation material, in particular to a preparation method of a super-hydrophobic oil-water separation material modified based on plant polyphenol-amino silicone oil.
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 a difficult problem to be solved urgently. In recent years, with the rapid development of nano and biomimetic technologies, people have systematic research and understanding on the relation between the microstructure of the solid surface and the wettability, and functional materials based on the super-wetting property indicate a new research direction for oil-water separation application. Researchers design and develop a series of special wetting materials with oil/water wettability difference and selective permeability by skillfully regulating and controlling the microstructure and chemical composition of the material surface, such as super-hydrophobic super-oleophilic materials, super-hydrophilic and underwater super-oleophobic materials, Janus surface materials, super-amphiphilic and super-amphiphilic surface materials and the like, and promote the rapid development of an oil-water separation technology.
At present, the oil-water separation material with super-hydrophobic and super-oleophylic characteristics is greatly developed and researched in the field of oil-water separation. Researchers often introduce low surface energy substances to "low surface energy" to achieve the hydrophobic and oleophilic properties of the material surface. In the prior art, organic solvents are generally used as a medium to introduce low surface energy species and covalently graft the low surface energy species to the surface of the material by further chemical reaction. Due to the use of organic solvents, on the one hand, the base material needs to have certain solvent resistance; on the other hand, the method also brings higher production cost and greater environmental pollution problem. In the method for modifying and functionalizing the surface interface of the material, in recent years, the bionic mussel chemistry represented by oxidative self-polymerization of dopamine is injected with great vigor for the development of the science and the technology of the surface interface of the material, and is widely researched and used for modifying and functionalizing the surface interface of the material. In the field of oil-water separation materials, some documents and patent reports exist on a super-hydrophobic bionic functional surface based on dopamine surface modification, but the problems of complicated preparation process, high cost, unsuitability for industrial production and application and the like still exist. Therefore, attention and development are urgently needed to develop an oil-water separation material with low cost, no pollution, simple preparation process and wide raw material sources.
The natural polyphenol compounds are widely present in peels, roots, woods, leaves and fruits of plants, have wide sources and low cost; it is found from the chemical structure of plant polyphenols that they have catechol groups that play a key role like dopamine, and may have chemical versatility similar to dopamine. The invention combines the chemical multifunctionality, low cost and water-solubility safety environmental protection characteristics of plant polyphenol with the low surface energy, water dispersibility, low cost and the like of amino silicone oil, firstly adopts the plant polyphenol to carry out surface pretreatment modification on a substrate and reserve the reaction activity, and then utilizes an active site to carry out chemical reaction to functionally graft the amino silicone oil, and the whole process adopts an aqueous solution environment, thereby realizing the low-cost and environmental protection preparation of the novel super-hydrophobic oil-water separation material.
Disclosure of Invention
The invention aims to overcome the defects and shortcomings of the prior art and provides a preparation method of a plant polyphenol-amino silicone oil modified super-hydrophobic oil-water separation material. The invention adopts natural polyphenol substances to carry out appropriate surface pretreatment modification on the surface of a base material and retain the reaction activity, and then realizes the preparation of the super-hydrophobic oil-water separation material with the characteristics of low cost, no pollution, simple preparation process, wide raw material source and the like by a covalent bond reaction mode, namely, the reaction between the catechol group and the derivative group of the natural polyphenol substances and the group (amino group and the like) of amino silicone oil.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method of a plant polyphenol-amino silicone oil modified super-hydrophobic oil-water separation material comprises the following steps:
(1) cleaning and drying the base material for later use;
(2) dissolving plant polyphenol in water, and adding an alkaline substance to adjust the pH value to 7.1-13 to obtain a plant polyphenol solution with the mass concentration of 0.001-30%;
(3) dissolving ferric chloride in water to obtain an iron ion solution with the mass concentration of 0-15%;
(4) dispersing amino silicone oil in water to obtain an amino silicone oil aqueous dispersion liquid with the mass concentration of 0.01-50%;
(5) soaking the dried substrate in a plant polyphenol solution for 1 second to 12 hours, taking out and drying, then soaking in an iron ion solution for 1 second to 0.5 hours, taking out and drying; repeating the process for at least 1 time, and then drying in a drying oven at 25-120 ℃ for 0.1-12 hours to obtain the plant polyphenol modified base material;
(6) and (3) soaking the plant polyphenol modified base material obtained in the step (5) in amino silicone oil aqueous dispersion, 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 the super-hydrophobic oil-water separation material modified by the plant polyphenol-amino silicone oil.
The base material in the step (1) is a fabric net or a sponge;
the fabric net is at least one of a stainless steel net, a copper net, an iron net, an aluminum alloy net, a PET non-woven fabric net, a PP non-woven fabric net and a nylon non-woven fabric net;
the sponge is at least one of natural sponge, wood cellulose fiber sponge and synthetic sponge; the synthetic sponge is at least one of polyurethane sponge, melamine sponge, polyvinyl alcohol sponge, polyether sponge and polyester sponge.
The plant polyphenol in the step (2) is at least one of procyanidine, gallic acid, catechin, anthocyanin, quercetin, tannic acid and ellagic acid;
the alkaline substance is at least one of inorganic alkali and organic alkali; specifically, the inorganic base is at least one of sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide, aluminum hydroxide, lithium hydroxide, magnesium hydroxide, zinc hydroxide, copper hydroxide, iron hydroxide, lead hydroxide, cobalt hydroxide, chromium hydroxide, zirconium hydroxide, nickel hydroxide, ammonium hydroxide, soda ash, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate and sodium peroxycarbonate; the organic alkali is at least one of trihydroxymethyl aminomethane, trimethylamine, sodium methoxide, sodium ethoxide and quaternary ammonium hydroxide.
The amino silicone oil in the step (4) has an average molecular weight of 1000-1000000 and an ammonia value of 0.1-1.5.
The super-hydrophobic oil-water separation material based on plant polyphenol-amino silicone oil modification prepared by the method can be applied to oil-water separation.
In the invention, the amino silicone oil has water dispersibility, because the amino silicone oil contains a certain content of hydrophilic amino groups in the molecule, when the content of amino groups is higher, microemulsion can be spontaneously formed in water, and when the content of amino groups is lower, stable emulsion can be easily emulsified by a proper surfactant.
The catechol or the phenolic hydroxyl in the catechol structure in the molecular structure of the plant polyphenol compound is easily oxidized into quinone structure, and the quinone structure can react with amino groups in amino silicone oil through Michael addition, Schiff base and other reactions (the reaction formula is shown in the specification), so that the amino silicone oil is stably fixed on surface chemical bonds, and the low surface energy hydrophobic modification of the base material is realized.
Compared with the prior art, the invention has the following advantages and effects:
1. the chemical reaction between the plant polyphenol compound and the amino silicone oil is utilized, so that the whole process adopts aqueous solution for reaction, and the low-cost and environment-friendly preparation of the super-hydrophobic oil-water separation material is realized;
2. the invention has the advantages of easily obtained raw materials, wide sources and simple preparation process.
3. The plant polyphenol used in the invention has strong adhesive force on the surface of a matrix and a plurality of reactive sites, and can perform a plurality of reactions with a plurality of substances.
4. The super-hydrophobic oil-water separation material prepared by the invention has better separation capability on oil substances, and has the advantages of low treatment cost, simple and convenient operation and cyclic use for many times.
Drawings
FIG. 1 is a photograph showing the water contact angle of the oil-water separating material prepared in example 1.
FIG. 2 is an SEM photograph of the oil-water separation material prepared in example 1.
FIG. 3 is a graph showing the effect of oil-water separation using the oil-water separating material prepared in example 1.
FIG. 4 is a graph showing the effect of oil-water separation on various oil-water mixtures using the oil-water separation material prepared in example 1.
FIG. 5 is a graph showing separation efficiency data of a repeated separation experiment of a carbon tetrachloride/water mixture using the oil-water separation material prepared in example 1.
FIG. 6 is a photograph showing the water contact angle of the oil-water separating material prepared in example 2.
FIG. 7 is an SEM photograph of the oil-water separation material prepared in example 2.
FIG. 8 is a graph showing the effect of oil-water separation using the oil-water separating material prepared in example 2.
FIG. 9 is a graph showing the effect of oil-water separation on various oil-water mixtures using the oil-water separation material prepared in example 2.
FIG. 10 is a graph showing separation efficiency data of an experiment in which the oil-water separation material prepared in example 2 was used to repeatedly separate an n-heptane/water mixture.
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) Cleaning and drying the 300-mesh stainless steel mesh substrate for later use;
(2) dissolving tannic acid in water, adding sodium hydroxide to adjust pH to 8.5 to obtain tannic acid solution with tannic acid mass concentration of 2%; dissolving ferric chloride in water to obtain an iron ion solution with the mass concentration of iron ions being 1%; dispersing amino silicone oil (with average molecular weight of 100000 and ammonia value of 0.6) in water to obtain 3% amino silicone oil aqueous dispersion liquid;
(3) soaking the dried stainless steel mesh substrate in a tannic acid solution for 5 minutes, and taking out and drying; then soaking in iron ion solution for 1 minute, taking out and airing; repeating the process for 5 times, and drying in a drying oven at 60 ℃ for 12 hours to obtain a tannin modified substrate;
(4) and (3) soaking the tannic acid modified base material obtained in the step (3) in amino silicone oil aqueous dispersion, reacting for 24 hours at the temperature of 60 ℃, taking out, and drying for 6 hours in a drying oven at the temperature of 60 ℃ to obtain the tannic acid-amino silicone oil modified super-hydrophobic oil-water separation material.
FIG. 1 is a photograph showing the water contact angle of the oil-water separating material prepared in this example. As can be seen from the figure, the prepared oil-water separation material has better super-hydrophobic property, and the contact angle is larger than 150 degrees.
Fig. 2 is an SEM image of the oil-water separation mesh membrane prepared in this example. It can be seen from the figure that the prepared oil-water separation material has a rough structure on the surface.
Fig. 3 is a graph showing the effect of oil-water separation using the oil-water separation mesh membrane prepared in this example. As can be seen from the figure, the separation membrane is arranged in the separation device, so that the oil-water mixture can be effectively separated.
FIG. 4 is a graph showing the comparison of the oil-water separation effect of the oil-water separation material of this embodiment on different oil-water mixtures (using dichloroethane, carbon tetrachloride, chloroform, dichloromethane, and paraffin oil as oil components). The results show that the separation material has higher separation efficiency (all more than 95%) for different oils.
FIG. 5 is a graph showing the separation efficiency data of the repeated separation experiment of carbon tetrachloride/water mixture using the oil-water separation material of this example. The result shows that the separation material can still maintain high oil-water separation efficiency after 10 times of repeated separation.
Example 2
(1) Cleaning and drying the melamine sponge base material for later use;
(2) dissolving procyanidine in water, adding trihydroxymethyl aminomethane to adjust pH to 9 to obtain procyanidine solution with procyanidine mass concentration of 5%; dissolving ferric chloride in water to obtain an iron ion solution with the mass concentration of iron ions being 2%; dispersing amino silicone oil (with average molecular weight of 50000 and ammonia value of 0.3) in water to obtain amino silicone oil aqueous dispersion liquid with mass concentration of 5%;
(3) soaking the dried melamine sponge base material in a procyanidine solution for 1 hour, and taking out and drying; then soaking the mixture in an iron ion solution for 0.5 hour, taking out and airing; repeating the process for 3 times, and drying in a drying oven at 80 deg.C for 6 hr to obtain procyanidin modified base material;
(4) and (3) soaking the procyanidine modified base material obtained in the step (3) in amino silicone oil aqueous dispersion, reacting for 12 hours at 70 ℃, taking out, and drying for 3 hours in a drying oven at 90 ℃ to obtain the superhydrophobic oil-water separation material based on procyanidine-amino silicone oil modification.
FIG. 6 is a photograph showing the water contact angle of the oil-water separating material prepared in this example. As can be seen from the figure, the prepared oil-water separation material has better super-hydrophobic property, and the contact angle is larger than 150 degrees.
Fig. 7 is an SEM image of the oil-water separation mesh membrane prepared in this example. It can be seen from the figure that the prepared oil-water separation material has a rough structure on the surface.
FIG. 8 is a graph showing the effect of oil-water separation using the oil-water separation mesh membrane prepared in this example. As can be seen from the figure, the oil-water separation net film prepared by the embodiment can quickly adsorb oil drops in water, and effectively perform oil-water separation.
FIG. 9 is a comparison graph of the oil-water separation effect of the oil-water separation material of this embodiment on different oil-water mixtures (with n-hexane, carbon tetrachloride, n-heptane, peanut oil and toluene as oil). The result shows that the separation material has higher oil absorption multiplying power for different oils.
FIG. 10 is a graph showing separation efficiency data of an experiment in which a water-oil separator was repeatedly used to separate an n-heptane/water mixture. The result shows that the separation material can still maintain high oil-water separation efficiency after 10 times of repeated separation.
Example 3
(1) Cleaning a 300-mesh copper mesh base material, and drying for later use;
(2) dissolving catechin in water, adding potassium hydroxide to adjust pH to 8.8 to obtain catechin solution with catechin mass concentration of 6%; dissolving ferric chloride in water to obtain an iron ion solution with the mass concentration of iron ions being 3%; dispersing amino silicone oil (with average molecular weight of 500000 and ammonia value of 0.6) in water to obtain 1% amino silicone oil aqueous dispersion liquid;
(3) soaking the dried copper mesh substrate in catechin solution for 2 minutes, taking out and drying in the air; then soaking the mixture in an iron ion solution for 5 minutes, taking out and airing; repeating the process for 8 times, and drying in a drying oven at 100 deg.C for 2 hr to obtain catechin modified base material;
(4) and (3) soaking the catechin modified base material obtained in the step (3) in amino silicone oil aqueous dispersion, reacting for 32 hours at 75 ℃, taking out, and drying for 4 hours in a drying oven at 80 ℃ to obtain the catechin-amino silicone oil modified super-hydrophobic oil-water separation material.
Through detection, the water contact angle of the oil-water separation material prepared by the embodiment is larger than 150 degrees, which indicates that the prepared oil-water separation material has better super-hydrophobic property; and the excellent oil-water separation effect can be still kept after 20 times of oil-water separation repeated experiments.
Example 4
(1) Cleaning and drying the polyurethane sponge base material for later use;
(2) dissolving quercetin in water, adding trimethylamine to adjust pH to 10 to obtain a quercetin solution with the mass concentration of quercetin of 4%; dispersing amino silicone oil (with average molecular weight of 50000 and ammonia value of 0.5) in water to obtain amino silicone oil aqueous dispersion liquid with mass concentration of 50%;
(3) soaking the dried polyurethane sponge base material in a quercetin solution for 5 hours, and taking out and drying the polyurethane sponge base material; repeating the process for 6 times, and drying in a drying oven at 100 ℃ for 6 hours to obtain a quercetin modified substrate;
(4) and (3) soaking the quercetin modified base material obtained in the step (3) in amino silicone oil aqueous dispersion, reacting for 22 hours at the temperature of 60 ℃, taking out, and drying for 6 hours in a drying oven at the temperature of 60 ℃ to obtain the quercetin-amino silicone oil modified super-hydrophobic oil-water separation material.
Through detection, the water contact angle of the oil-water separation material prepared by the embodiment is larger than 150 degrees, which indicates that the prepared oil-water separation material has better super-hydrophobic property; and the excellent oil-water separation effect can be still kept after 10 times of oil-water separation repeated experiments.
Example 5
(1) Cleaning and drying the PET non-woven fabric net base material for later use;
(2) dissolving ellagic acid in water, adding sodium hydroxide to adjust pH to 10, and obtaining an ellagic acid solution with ellagic acid mass concentration of 10%; dispersing amino silicone oil (with average molecular weight of 100000 and ammonia value of 0.8) in water to obtain 0.01% amino silicone oil aqueous dispersion liquid;
(3) soaking the dried PET non-woven fabric net base material in an ellagic acid solution for 1 hour, taking out and drying; repeating the process for 5 times, and drying in a drying oven at 70 ℃ for 5 hours to obtain the ellagic acid modified base material;
(4) and (3) soaking the ellagic acid modified base material obtained in the step (3) in amino silicone oil aqueous dispersion, reacting for 12 hours at 80 ℃, taking out, and drying for 4 hours in a drying oven at 60 ℃ to obtain the ellagic acid-amino silicone oil modified super-hydrophobic oil-water separation material.
Through detection, the water contact angle of the oil-water separation material prepared by the embodiment is larger than 150 degrees, which indicates that the prepared oil-water separation material has better super-hydrophobic property; and the excellent oil-water separation effect can be still kept after 20 times of oil-water separation repeated experiments.
Example 6
(1) Cleaning and drying the 200-mesh stainless steel mesh substrate for later use;
(2) dissolving procyanidin in water, adding trihydroxymethyl aminomethane to adjust pH to 13 to obtain procyanidin solution with procyanidin mass concentration of 0.001%; dissolving ferric chloride in water to obtain an iron ion solution with the mass concentration of iron ions being 15%; dispersing amino silicone oil (with average molecular weight of 1000 and ammonia value of 1.5) in water to obtain amino silicone oil aqueous dispersion liquid with mass concentration of 3%;
(3) soaking the dried 200-mesh stainless steel mesh substrate in a procyanidine solution for 1 second, and taking out and drying; then soaking the mixture in an iron ion solution for 0.5 hour, taking out and airing; repeating the process for 5 times, and drying in a drying oven at 25 deg.C for 12 hr to obtain procyanidin modified base material;
(4) and (3) soaking the procyanidine modified base material obtained in the step (3) in amino silicone oil aqueous dispersion, reacting for 48 hours at 80 ℃, taking out, and drying in a drying oven at 100 ℃ for 0.5 hour to obtain the super-hydrophobic oil-water separation material modified based on procyanidine-amino silicone oil.
Through detection, the water contact angle of the oil-water separation material prepared by the embodiment is larger than 150 degrees, which indicates that the prepared oil-water separation material has better super-hydrophobic property; and the excellent oil-water separation effect can be still kept after 20 times of oil-water separation repeated experiments.
Example 7
(1) Cleaning and drying the 200-mesh stainless steel mesh substrate for later use;
(2) dissolving tannic acid in water, adding sodium hydroxide to adjust pH to 7.1 to obtain tannic acid solution with tannic acid mass concentration of 30%; dissolving ferric chloride in water to obtain an iron ion solution with the mass concentration of iron ions being 1%; dispersing amino silicone oil (with average molecular weight of 1000000 and ammonia value of 0.5) in water to obtain amino silicone oil aqueous dispersion liquid with mass concentration of 4%;
(3) soaking the dried stainless steel mesh substrate in a tannic acid solution for 12 hours, and taking out and drying; then soaking in iron ion solution for 1 second, taking out and airing; repeating the process for 1 time, and drying in a drying oven at 120 ℃ for 0.1 hour to obtain the tannin modified substrate;
(4) and (3) soaking the tannic acid modified base material obtained in the step (3) in amino silicone oil aqueous dispersion, reacting for 1 hour at the temperature of 30 ℃, taking out, and drying for 6 hours in a drying oven at the temperature of 50 ℃ to obtain the tannic acid-amino silicone oil modified super-hydrophobic oil-water separation material.
Through detection, the water contact angle of the oil-water separation material prepared by the embodiment is larger than 150 degrees, which indicates that the prepared oil-water separation material has better super-hydrophobic property; and the excellent oil-water separation effect can be still kept after 20 times of oil-water separation repeated experiments.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (5)
1. A preparation method of a plant polyphenol-amino silicone oil modified super-hydrophobic oil-water separation material is characterized by comprising the following steps:
(1) cleaning and drying the base material for later use;
(2) dissolving plant polyphenol in water, and adding an alkaline substance to adjust the pH value to 7.1-13 to obtain a plant polyphenol solution with the mass concentration of 0.001-30%;
(3) dissolving ferric chloride in water to obtain an iron ion solution with the mass concentration of 0-15%;
(4) dispersing amino silicone oil in water to obtain an amino silicone oil aqueous dispersion liquid with the mass concentration of 0.01-50%;
(5) soaking the dried substrate in a plant polyphenol solution for 1 second to 12 hours, taking out and drying, then soaking in an iron ion solution for 1 second to 0.5 hours, taking out and drying; repeating the process for at least 1 time, and then drying in a drying oven at 25-120 ℃ for 0.1-12 hours to obtain the plant polyphenol modified base material;
(6) and (3) soaking the plant polyphenol modified base material obtained in the step (5) in amino silicone oil aqueous dispersion, 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 the super-hydrophobic oil-water separation material modified by the plant polyphenol-amino silicone oil.
2. The method of claim 1, wherein: the base material in the step (1) is a fabric net or a sponge;
the fabric net is at least one of a stainless steel net, a copper net, an iron net, an aluminum alloy net, a PET non-woven fabric net, a PP non-woven fabric net and a nylon non-woven fabric net;
the sponge is at least one of natural sponge, wood cellulose fiber sponge and synthetic sponge; the synthetic sponge is at least one of polyurethane sponge, melamine sponge, polyvinyl alcohol sponge, polyether sponge and polyester sponge.
3. The method of claim 1, wherein: the plant polyphenol in the step (2) is at least one of procyanidine, gallic acid, catechin, anthocyanin, quercetin, tannic acid and ellagic acid;
the alkaline substance is at least one of inorganic alkali and organic alkali.
4. The method of claim 1, wherein: the amino silicone oil in the step (4) has an average molecular weight of 1000-1000000 and an ammonia value of 0.1-1.5.
5. The application of the plant polyphenol-amino silicone oil modified-based super-hydrophobic oil-water separation material prepared by the method of any one of claims 1 to 4 in oil-water separation.
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| CN111663330A (en) * | 2020-06-19 | 2020-09-15 | 中国林业科学研究院林产化学工业研究所 | Plant tannin mediated super-hydrophobic cellulose material and preparation method and application thereof |
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| CN112144288A (en) * | 2020-09-11 | 2020-12-29 | 中国林业科学研究院林产化学工业研究所 | Cardanol-based super-hydrophobic cotton fabric and preparation method and application thereof |
| CN112144288B (en) * | 2020-09-11 | 2023-04-07 | 中国林业科学研究院林产化学工业研究所 | Cardanol-based super-hydrophobic cotton fabric and preparation method and application thereof |
| CN114425508A (en) * | 2020-10-13 | 2022-05-03 | 中国石油化工股份有限公司 | Metal material with super-hydrophobic surface, preparation method and application thereof, and oil-water separation method |
| CN112813683A (en) * | 2021-02-05 | 2021-05-18 | 武汉理工大学 | Super-amphiphobic fabric and preparation method thereof |
| CN112813683B (en) * | 2021-02-05 | 2023-09-22 | 武汉理工大学 | Super-amphiphobic fabric and preparation method thereof |
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