CN108752904B - Super-hydrophobic polyurethane elastomer and preparation method thereof - Google Patents

Super-hydrophobic polyurethane elastomer and preparation method thereof Download PDF

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CN108752904B
CN108752904B CN201810265775.XA CN201810265775A CN108752904B CN 108752904 B CN108752904 B CN 108752904B CN 201810265775 A CN201810265775 A CN 201810265775A CN 108752904 B CN108752904 B CN 108752904B
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polyurethane
polyurethane elastomer
super
polysiloxane
hydrophobic
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CN108752904A (en
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林殷雷
李光吉
陈东初
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Foshan University
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/61Polysiloxanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/83Chemically modified polymers
    • C08G18/837Chemically modified polymers by silicon containing compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00Polymer mixtures characterised by other features
    • C08L2205/02Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure

Abstract

The invention discloses a super-hydrophobic polyurethane elastomer and a preparation method thereof, wherein the raw material components comprise, by mass, 12-30 parts of isocyanate, 50-75 parts of polysiloxane and 13-20 parts of a silane coupling agent; when in preparation, polysiloxane and isocyanate are reacted to obtain a polyurethane prepolymer with an isocyanate group at the tail end; then reacting the silane coupling agent with the polyurethane prepolymer to obtain silane coupling agent-terminated polyurethane; then preparing polyurethane particles under the alkaline condition; and finally, reacting the polyurethane particles with the polyurethane prepolymer to obtain the super-hydrophobic polyurethane elastomer. The super-hydrophobic polyurethane elastomer has the advantages of simple synthesis process, readily available raw materials, low cost, tensile strength of more than or equal to 4MPa, elongation at break of more than or equal to 400 percent and contact angle between the surface of the super-hydrophobic polyurethane elastomer and water of 158 degrees.

Description

Super-hydrophobic polyurethane elastomer and preparation method thereof
Technical Field
The invention relates to a polyurethane elastomer, in particular to a super-hydrophobic polyurethane elastomer and a preparation method thereof.
Background
Polyurethanes are a generic name for high-molecular polymers containing recurring carbamate groups (-NHCOO-) in the molecular structure. The polyurethane elastomer has excellent performances of wear resistance, tear resistance, oil resistance, chemical corrosion resistance, high elasticity and the like, and is widely applied to a plurality of fields of automobile manufacturing, transportation, civil construction, footwear, synthetic leather, medical treatment, agriculture and the like.
However, polyurethane elastomers are susceptible to contamination from dust and other substances during use, which can seriously affect their aesthetics and performance. Therefore, the function of imparting superhydrophobicity to polyurethane elastomers is one of the most effective ways to solve this problem. The super-hydrophobic material refers to a material with a contact angle of more than 150 degrees and a rolling angle of less than 10 degrees on the surface of a water drop. The super-hydrophobic material has the characteristics of self-cleaning, corrosion prevention, ice prevention, drag reduction and the like, and has wide application prospects in daily life, industrial production and biomedicine, so that the super-hydrophobic material is greatly concerned by researchers. Because of the wide performance spectrum and strong designability of polyurethane, the polyurethane is often used for constructing super-hydrophobic materials meeting different application requirements. In a research paper "preparation and performance of a bionic super-hydrophobic silica/polyurethane composite coating (well-known, wangdong, li ruifeng, polymer science and engineering, 2014,30,136.)", an author prepares a super-hydrophobic composite coating by using nano silica and polyurethane modified by different organic silicon contents as raw materials, using ethyl acetate as a dispersing agent and adopting a simple spraying process. However, in the coating preparation process, the light nano silica is easy to migrate to the surface layer of the mixture, and the compatibility of the mixture and polyurethane is poor, so that the coating structure is easy to be uneven, and the performance difference is large. Recently, chinese patent application CN 107286318A discloses a super-hydrophobic polyurethane coating and a preparation method thereof, which is prepared from fluorine-containing isocyanate, oligomer polyol and cage-type polysilsesquioxane as main raw materials, but the fluorine-containing substance is expensive and is not suitable for industrial production. In addition, no relevant literature reports about the super-hydrophobic polyurethane elastomer.
Disclosure of Invention
The invention overcomes the defects in the prior art, provides the super-hydrophobic polyurethane elastomer, and adopts a typical sol-gel method to prepare polyurethane particles, and the particles can improve the compatibility with a polyurethane chain segment due to the action of polar carbamate in the polyurethane chain segment; the particles also contain long polysiloxane chains, so that the particles have certain elasticity; in addition, the hydrophobicity of the polysiloxane can improve the hydrophobic properties of the particle surface.
The invention also provides a preparation method of the super-hydrophobic polyurethane elastomer, which is easy to realize, has easily obtained raw materials, no fluorine-containing substances, low cost and stronger controllability of material composition and structure and is suitable for industrial production.
In order to solve the technical problems, the invention is realized by the following technical scheme:
a super-hydrophobic polyurethane elastomer comprises the following raw materials in parts by weight:
12-30 parts of isocyanate
50-75 parts of polysiloxane
13-20 parts of a silane coupling agent.
Further, the isocyanate is one or more of isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, toluene diisocyanate, diphenylmethane-4, 4' -diisocyanate, xylylene diisocyanate, methylcyclohexyl diisocyanate, tetramethylxylylene diisocyanate, HDI trimer, IPDI trimer, TDI trimer and MDI trimer.
Further, the polysiloxane is one or more of hydroxyl-terminated polysiloxane, amino-terminated polysiloxane and hydroxyl-terminated polyether polysiloxane; the molecular weight of the polysiloxane is 1000-6000 g/mol.
Further, the silane coupling agent is any one or a mixture of more of 3-aminopropyltrimethoxysilane, N-aminoethyl-3-aminopropyltriethoxysilane, N-aminoethyl-gamma-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, (3-mercaptopropyl) triethoxysilane, gamma-glycidoxypropyltrimethoxysilane and 3-glycidoxypropyltriethoxysilane.
A preparation method of a super-hydrophobic polyurethane elastomer is characterized by comprising the following steps:
(1) preparation of polyurethane particles: mixing and stirring polysiloxane and isocyanate uniformly, and reacting for 2-10 hours at 60-100 ℃ to obtain a polyurethane prepolymer with an isocyanate group at the tail end; adding a silane coupling agent into a reaction system, and reacting for 2-5 hours at 60-90 ℃ to obtain polyurethane terminated by the silane coupling agent; dispersing the polyurethane particles in a first solvent, dropwise adding ammonia water to enable the pH value of a reaction system to be 10-13, reacting at 25-60 ℃ for 10-24 hours, washing for 2-4 times by using the first solvent after the reaction is finished, and drying in vacuum to obtain polyurethane particles;
(2) preparation of the super-hydrophobic polyurethane elastomer: dispersing polyurethane particles in a second solvent, adding the polyurethane prepolymer in the step (1), uniformly stirring, pouring into a polytetrafluoroethylene mold, drying and curing to obtain the super-hydrophobic polyurethane elastomer.
Further, the first solvent is any one or a mixture of ethanol, methanol, ethyl acetate and propanol; the first solvent is 10 times the fraction of polysiloxane.
Further, the second solvent is any one or a mixture of ethanol, propanol, ethyl acetate, methanol, toluene, n-butanol, acetone and tetrahydrofuran; the second solvent is 5 times of the polyurethane particle portion.
Further, the mass fraction of the ammonia water is 30%.
Further, the temperature of the vacuum drying in the step (1) is 50 ℃, and the time of the vacuum drying is 10-24 hours.
Further, the drying temperature in the step (2) is 90-120 ℃, and the curing time is 3-5 hours
Compared with the prior art, the invention has the beneficial effects that:
1) the super-hydrophobic polyurethane elastomer has tensile strength of more than or equal to 4MPa, elongation at break of more than or equal to 400 percent and a contact angle between the surface of the super-hydrophobic polyurethane elastomer and water of 150-158 degrees.
2) The raw materials used in the invention are cheap and easily available, no fluorine-containing substance is contained, no special condition and equipment are needed in the synthesis process, and the synthesis process is easy to realize and regulate.
3) The super-hydrophobic polyurethane elastomer is easy to realize in process, and the structure and the performance of a product can be easily regulated and controlled in a large range by regulating the reaction amount of polysiloxane, a silane coupling agent and isocyanate.
4) The polyurethane raw materials, the polysiloxane and the silane coupling agent required by the preparation method are all commercial industrial products, and the process for synthesizing the polyurethane is mature. Therefore, the preparation process is simple and easy to implement and has low cost.
Drawings
The accompanying drawings are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, with the understanding that the present disclosure is to be considered as an exemplification of the invention and is not intended to limit the invention to the embodiments illustrated in the drawings, in which:
FIG. 1 is an IR spectrum of a polyurethane prepolymer prepared in example 1.
FIG. 2 is an infrared spectrum of the silane coupling agent-terminated polyurethane obtained in example 1.
FIG. 3 is an IR spectrum of polyurethane particles obtained in example 1.
Fig. 4(a) is a photograph of a water droplet on the surface of a general polyurethane elastomer, and 4(b) is a photograph of a water droplet on the surface of a superhydrophobic polyurethane elastomer prepared in example 1.
Fig. 5 is an SEM photograph of the surface of the superhydrophobic polyurethane elastomer prepared in example 1.
Detailed Description
The preferred embodiments of the present invention will be described in conjunction with the accompanying drawings, and it will be understood that they are described herein for the purpose of illustration and explanation and not limitation.
Example 1
Preparation of polyurethane particles: mixing 75 parts of hydroxyl-terminated polysiloxane and 12 parts of 1, 6-hexamethylene diisocyanate, uniformly stirring, and reacting at 100 ℃ for 2 hours to obtain a polyurethane prepolymer with an isocyanate group at the tail end; adding 13 parts of 3-aminopropyltrimethoxysilane into the reaction system, and reacting for 2 hours at 90 ℃ to obtain polyurethane terminated by a silane coupling agent; then dispersing the polyurethane particles in ethanol, dropwise adding ammonia water to enable the pH value of a reaction system to be 10, reacting for 24 hours at 25 ℃, cleaning for 2 times by using ethanol after the reaction is finished, and drying for 10 hours in vacuum at 50 ℃ to obtain polyurethane particles;
preparation of the super-hydrophobic polyurethane elastomer: dispersing 10 parts of polyurethane particles in acetone, adding 10 parts of polyurethane prepolymer, uniformly stirring, pouring into a polytetrafluoroethylene mold, and drying and curing at 90 ℃ for 5 hours to obtain the super-hydrophobic polyurethane elastomer.
The polyurethane prepolymer prepared in the embodiment is crosslinked to obtain a common polyurethane elastomer, and relevant performances of the common polyurethane elastomer are tested and compared with performances of the super-hydrophobic polyurethane elastomer prepared in the embodiment.
FIG. 1 is an IR spectrum of a polyurethane prepolymer prepared in this example. As can be seen, at 2271cm-1The asymmetric stretching vibration peak of-N ═ C ═ O appears at 1705cm-1A stretching vibration absorption peak of-C ═ O in the urethane appears at 1527cm-1Where an absorption peak of amide II in polyurethane appeared, 3337cm-1Is the N-H stretching vibration peak in carbamate at 1260cm-1The absorption peak of Si-C appears at 1093cm-1Is the stretching vibration absorption peak of Si-O-Si, 800cm-1The bending vibration peak of the methyl group on the Si atom. The infrared analysis shows that the designed polyurethane prepolymer is indeed synthesized.
FIG. 2 is an infrared spectrum of the polyurethane blocked with silane coupling agent prepared in this example. As can be seen, at 2271cm-1The asymmetric stretching vibration peak of-N ═ C ═ O disappears at 1571cm-1Where an absorption peak of amide II in polyurethane, 3331cm, appears-1Is the N-H stretching vibration peak in carbamate, 1704cm-1The peak of the C ═ O absorption of stretching vibration is 1258cm-1The absorption peak of Si-C is 1076cm-1789cm, which is the stretching vibration absorption peak of Si-O-Si-1The bending vibration peak of the methyl group on the Si atom. The infrared analysis shows that the designed silane coupling agent-terminated polyurethane is indeed synthesized.
FIG. 3 shows the polyurethane particles obtained in this exampleAnd (4) an infrared spectrum. As can be seen in the figure, at 1576cm-1Where an absorption peak of amide II in the polyurethane appeared, 3332cm-1Is the N-H stretching vibration peak in carbamate, 1704cm-1The absorption peak of C ═ O in stretching vibration is 1090cm-1To 1260cm-1The absorption peak of (2) becomes broad. This infrared analysis indicates that the designed polyurethane particles were indeed synthesized.
Fig. 4(a) is a photograph of a conventional polyurethane elastomer obtained by forming a water drop in this example, and fig. 4(b) is a photograph of a superhydrophobic polyurethane elastomer obtained by forming a water drop in this example, wherein the water drop is semicircular on the surface of the conventional polyurethane elastomer and circular on the surface of the superhydrophobic polyurethane elastomer.
Fig. 5 is an SEM image of the surface of the superhydrophobic polyurethane elastomer prepared in this example, from which it can be clearly seen that the surface of the polyurethane elastomer has roughness of various sizes, and this surface roughness structure increases the hydrophobicity of the surface.
The water contact angle WCA of the surface of the material in the air is measured by using a DSA100 contact angle measuring instrument of KRUSS company in Germany, contact angle pictures are collected, and the experimental result is the average value of five tests of different positions of the surface of the sample. The contact angle of the surface of the superhydrophobic polyurethane elastomer prepared in this example with water was measured to be 158 ° and the contact angle of the conventional polyurethane elastomer was measured to be 110 °.
The breaking elongation of the super-hydrophobic polyurethane elastomer prepared by the embodiment is 450% and the tensile strength is 4.2MPa measured according to the national standard GB/T528-2009; the elongation at break of a conventional polyurethane elastomer is 260% and the tensile strength is 3.0 MPa.
Example 2
Preparation of polyurethane particles: mixing and stirring 50 parts of amino-terminated polysiloxane and 30 parts of diphenylmethane-4, 4' -diisocyanate uniformly, and reacting at 60 ℃ for 10 hours to obtain a polyurethane prepolymer with an isocyanate group at the tail end; then adding 20 parts of N-aminoethyl-gamma-aminopropyltrimethoxysilane into the reaction system, and reacting for 5 hours at 60 ℃ to obtain polyurethane terminated by a silane coupling agent; then dispersing the polyurethane particles in methanol, dropwise adding ammonia water to enable the pH value of a reaction system to be 13, reacting for 10 hours at 60 ℃, cleaning for 4 times by using ethanol after the reaction is finished, and drying for 24 hours in vacuum at 50 ℃ to obtain polyurethane particles;
preparation of the super-hydrophobic polyurethane elastomer: dispersing 10 parts of polyurethane particles in ethyl acetate, adding 10 parts of polyurethane prepolymer, uniformly stirring, pouring into a polytetrafluoroethylene mold, and drying and curing at 120 ℃ for 3 hours to obtain the super-hydrophobic polyurethane elastomer.
The contact angle of the surface of the superhydrophobic polyurethane elastomer prepared in this example with water was measured to be 150 °. The super-hydrophobic polyurethane elastomer prepared in the embodiment has the breaking elongation of 420% and the tensile strength of 4.6MPa measured according to the national standard GB/T528-2009.
Example 3
Preparation of polyurethane particles: mixing and stirring 60 parts of amino-terminated polysiloxane and 25 parts of isophorone diisocyanate uniformly, and reacting for 4.5 hours at 75 ℃ to obtain a polyurethane prepolymer with an isocyanate group at the tail end; adding 15 parts of 3-glycidyl ether oxypropyltriethoxysilane into a reaction system, and reacting for 3 hours at 75 ℃ to obtain silane coupling agent terminated polyurethane; then dispersing the polyurethane particles in ethanol, dropwise adding ammonia water to enable the pH value of a reaction system to be 12, reacting for 18 hours at 40 ℃, cleaning for 3 times by using ethanol after the reaction is finished, and drying for 20 hours in vacuum at 50 ℃ to obtain polyurethane particles;
preparation of the super-hydrophobic polyurethane elastomer: dispersing 10 parts of polyurethane particles in toluene, adding 10 parts of polyurethane prepolymer, uniformly stirring, pouring into a polytetrafluoroethylene mold, and drying and curing at 110 ℃ for 4 hours to obtain the super-hydrophobic polyurethane elastomer.
The contact angle of the surface of the superhydrophobic polyurethane elastomer prepared in this example with water was measured to be 152 °. The super-hydrophobic polyurethane elastomer prepared in the embodiment has the breaking elongation of 400% and the tensile strength of 4.8MPa measured according to the national standard GB/T528-2009.
Example 4
Preparation of polyurethane particles: mixing 65 parts of hydroxyl-terminated polysiloxane and 26 parts of isophorone diisocyanate, uniformly stirring, and reacting at 85 ℃ for 3 hours to obtain a polyurethane prepolymer with an isocyanate group at the tail end; adding 17 parts of N-aminoethyl-3-aminopropyltriethoxysilane into a reaction system, and reacting for 4 hours at 80 ℃ to obtain silane coupling agent terminated polyurethane; then dispersing the polyurethane particles in ethanol, dropwise adding ammonia water to enable the pH value of a reaction system to be 11, reacting for 15 hours at 50 ℃, cleaning for 3 times by using ethanol after the reaction is finished, and drying for 24 hours in vacuum at 50 ℃ to obtain polyurethane particles;
preparation of the super-hydrophobic polyurethane elastomer: dispersing 10 parts of polyurethane particles in toluene, adding 10 parts of polyurethane prepolymer, uniformly stirring, pouring into a polytetrafluoroethylene mold, drying and curing at 100 ℃ for 4.5 hours to obtain the super-hydrophobic polyurethane elastomer.
The contact angle of the surface of the superhydrophobic polyurethane elastomer prepared in this example with water was measured to be 152 °. The super-hydrophobic polyurethane elastomer prepared in the embodiment has the breaking elongation of 430% and the tensile strength of 4.3MPa measured according to the national standard GB/T528-2009.
Finally, it should be noted that: although the present invention has been described in detail with reference to the embodiments, it will be apparent to those skilled in the art that modifications may be made to the embodiments or portions thereof without departing from the spirit and scope of the invention.

Claims (9)

1. The super-hydrophobic polyurethane elastomer is characterized by comprising the following raw materials in parts by mass:
12-30 parts of isocyanate
50-75 parts of polysiloxane
13-20 parts of a silane coupling agent;
the preparation method comprises the following steps:
(1) preparation of polyurethane particles: mixing and stirring polysiloxane and isocyanate uniformly, and reacting for 2-10 hours at 60-100 ℃ to obtain a polyurethane prepolymer with an isocyanate group at the tail end; adding a silane coupling agent into a reaction system, and reacting for 2-5 hours at 60-90 ℃ to obtain polyurethane terminated by the silane coupling agent; dispersing the polyurethane particles in a first solvent, dropwise adding ammonia water to enable the pH value of a reaction system to be 10-13, reacting at 25-60 ℃ for 10-24 hours, washing for 2-4 times by using the first solvent after the reaction is finished, and drying in vacuum to obtain polyurethane particles;
(2) preparation of the super-hydrophobic polyurethane elastomer: dispersing polyurethane particles in a second solvent, adding the polyurethane prepolymer in the step (1), uniformly stirring, pouring into a polytetrafluoroethylene mold, drying and curing to obtain the super-hydrophobic polyurethane elastomer.
2. The superhydrophobic polyurethane elastomer of claim 1, wherein the isocyanate is one or more of isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, toluene diisocyanate, diphenylmethane-4, 4' -diisocyanate, xylylene diisocyanate, methylcyclohexyl diisocyanate, tetramethylxylylene diisocyanate, HDI trimer, IPDI trimer, TDI trimer, and MDI trimer.
3. The super-hydrophobic polyurethane elastomer according to claim 1, wherein the polysiloxane is one or more of hydroxyl terminated polysiloxane, amino terminated polysiloxane and hydroxyl terminated polyether polysiloxane; the molecular weight of the polysiloxane is 1000-6000 g/mol.
4. The superhydrophobic polyurethane elastomer according to claim 1, wherein the silane coupling agent is any one or more of 3-aminopropyltrimethoxysilane, N-aminoethyl-3-aminopropyltriethoxysilane, N-aminoethyl- γ -aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, (3-mercaptopropyl) triethoxysilane, γ -glycidoxypropyltrimethoxysilane, and 3-glycidoxypropyltriethoxysilane.
5. The super-hydrophobic polyurethane elastomer as claimed in claim 1, wherein the first solvent is a mixture of any one or more of ethanol, methanol, ethyl acetate, propanol; the first solvent is 10 times the fraction of polysiloxane.
6. The super-hydrophobic polyurethane elastomer as claimed in claim 1, wherein the second solvent is a mixture of one or more selected from ethanol, propanol, ethyl acetate, methanol, toluene, n-butanol, acetone, tetrahydrofuran; the second solvent is 5 times of the polyurethane particle portion.
7. The superhydrophobic polyurethane elastomer of claim 1, wherein the ammonia water is 30% by mass.
8. The superhydrophobic polyurethane elastomer according to claim 1, wherein the temperature of the vacuum drying in the step (1) is 50 ℃ and the time of the vacuum drying is 10-24 hours.
9. The superhydrophobic polyurethane elastomer according to claim 1, wherein the drying temperature in step (2) is 90-120 ℃ and the curing time is 3-5 hours.
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