CN108580227B - Rapid preparation method of super-hydrophobic paint surface - Google Patents
Rapid preparation method of super-hydrophobic paint surface Download PDFInfo
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- CN108580227B CN108580227B CN201810358218.2A CN201810358218A CN108580227B CN 108580227 B CN108580227 B CN 108580227B CN 201810358218 A CN201810358218 A CN 201810358218A CN 108580227 B CN108580227 B CN 108580227B
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- 239000003973 paint Substances 0.000 title claims abstract description 56
- 230000003075 superhydrophobic effect Effects 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000011347 resin Substances 0.000 claims abstract description 55
- 229920005989 resin Polymers 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 30
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 28
- -1 polytetrafluoroethylene Polymers 0.000 claims abstract description 26
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims abstract description 26
- 239000004810 polytetrafluoroethylene Substances 0.000 claims abstract description 26
- 238000001035 drying Methods 0.000 claims abstract description 18
- 238000000016 photochemical curing Methods 0.000 claims abstract description 18
- 239000011780 sodium chloride Substances 0.000 claims abstract description 14
- 238000002791 soaking Methods 0.000 claims abstract description 12
- 239000000243 solution Substances 0.000 claims abstract description 12
- 239000000758 substrate Substances 0.000 claims abstract description 12
- VSYDLUXFKAXBBY-UHFFFAOYSA-N C(C=1C(C(=O)O)=CC=CC1)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(COCCO)O Chemical compound C(C=1C(C(=O)O)=CC=CC1)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(COCCO)O VSYDLUXFKAXBBY-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 229910021642 ultra pure water Inorganic materials 0.000 claims abstract description 6
- 239000012498 ultrapure water Substances 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 6
- 239000002105 nanoparticle Substances 0.000 claims description 14
- FTCIOUYXOOXMBV-UHFFFAOYSA-N OC(=O)c1ccccc1C(O)=O.C=CC(=O)OCCOCCOC(=O)C=C Chemical compound OC(=O)c1ccccc1C(O)=O.C=CC(=O)OCCOCCOC(=O)C=C FTCIOUYXOOXMBV-UHFFFAOYSA-N 0.000 claims description 6
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 description 10
- 238000004140 cleaning Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000001338 self-assembly Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
- B05D5/08—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain an anti-friction or anti-adhesive surface
- B05D5/083—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain an anti-friction or anti-adhesive surface involving the use of fluoropolymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
- B05D5/02—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain a matt or rough surface
Landscapes
- Application Of Or Painting With Fluid Materials (AREA)
- Paints Or Removers (AREA)
Abstract
The invention discloses a quick preparation method of a super-hydrophobic paint surface, which comprises the following steps: step one, placing a photocuring resin film with a regular-shaped micron-scale rough surface structure in an aqueous solution of diethylene glycol diacrylate phthalate and sodium chloride for soaking for 3-20 min; step two, taking out the light-cured resin film, completely soaking the light-cured resin film into 3-10% of polytetrafluoroethylene solution in parts by weight for 5-30 min; thirdly, washing the light-cured resin film with ultrapure water, and drying for 5-20 min; and fourthly, stamping the rough surface structure of the light-cured resin film on the paint on the surface of the substrate, pressurizing and drying for 18-36h, and removing the light-cured resin film to obtain the super-hydrophobic paint surface. The invention provides a quick preparation method of a super-hydrophobic paint surface, which has the advantages of simple and convenient process, large forming area, high preparation speed, wide application range and the like, and has good engineering application prospect.
Description
Technical Field
The invention relates to the technical field of material surface treatment, in particular to a quick preparation method of a super-hydrophobic paint surface.
Background
Since the 90 s of the last century, the superhydrophobic construction of material surfaces has been a continuous hot spot problem. The super-hydrophobic surface has a self-cleaning function, which is called lotus effect by people, and is beneficial to the function, and the super-hydrophobic surface is usually used for preventing ice, snow, pollution, corrosion, self-cleaning and the like.
The hydrophobic property of the surface of the material is determined by the surface free energy and the surface microstructure of the surface material, so that the preparation of the super-hydrophobic surface is started from the aspects of reducing the surface free energy of the surface material and constructing the hydrophobic microstructure. At present, the methods for constructing the superhydrophobic surface are various, wherein the self-assembly technology for preparing the superhydrophobic surface is to assemble particles with low surface free energy on the surface of a matrix through stacking, static electricity and other methods, reduce the surface energy of a material, and construct a micro-rough structure on the surface of the material, so that the superhydrophobic surface of a component is constructed.
Therefore, how to provide a method for rapidly preparing a superhydrophobic surface by using a self-assembly technology is a technical problem to be solved by those skilled in the art.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a quick preparation method of a super-hydrophobic paint surface, and solves the difficult problems in the background art.
In order to achieve the purpose, the invention is realized by the following technical scheme: a method for quickly preparing a super-hydrophobic paint surface comprises the following steps: step one, placing a photocuring resin film with a regular-shaped micron-scale rough surface structure in an aqueous solution of diethylene glycol diacrylate phthalate and sodium chloride for soaking for 3-20 min; step two, taking out the photo-curing resin film, completely soaking the photo-curing resin film into 3-10% of polytetrafluoroethylene solution in parts by mass for 5-30min, and assembling polytetrafluoroethylene nanoparticles on the rough surface structure of the photo-curing resin film; thirdly, washing the photo-curing resin film obtained in the second step by using ultrapure water, and drying for 5-20 min; and fourthly, stamping the rough surface structure of the light-cured resin film on the paint on the surface of the substrate, pressurizing and drying for 18-36h, and removing the light-cured resin film to obtain the super-hydrophobic paint surface.
In some embodiments, in the method for rapidly preparing a superhydrophobic paint surface, the rough surface structure of the photocurable resin film is a regularly arranged pit structure.
In some embodiments, in the method for quickly preparing a superhydrophobic paint surface, the pit structure is a counter bore with a square cross section, the side length of the square is 5-15 μm, the depth value of the counter bore is 5-20 μm, and the distance between two adjacent counter bores is 10-50 μm.
In some embodiments, the first step further comprises previously subjecting the diethylene glycol phthalate diacrylate and the sodium chloride to ultrasonic vibration for 10-30 min.
In some embodiments, in the method for rapidly preparing a superhydrophobic paint surface, the mass portion of the diethylene glycol phthalate diacrylate is 0.05% to 2.05%, and the concentration of the sodium chloride is 0.05 mmol/L.
In some embodiments, in the method for rapidly preparing a superhydrophobic paint surface, between the first step and the second step, the ultrasonic stirring of the polytetrafluoroethylene solution is performed in advance for 30-60 min.
In some embodiments, in the method for rapidly preparing a superhydrophobic paint surface, the particle size of the polytetrafluoroethylene nanoparticles is 100-300 nm.
In some embodiments, in the method for rapidly preparing a superhydrophobic painted surface, the paint on the surface of the substrate is fluorocarbon resin paint, and the thickness of the fluorocarbon resin paint is 40-150 μm.
In some embodiments, in the method for rapidly preparing a superhydrophobic paint surface, the pressure drying in the fourth step is performed under a pressure value of 0.1-15g/mm2And drying at room temperature.
In some embodiments, in the second step of the method for rapidly preparing a superhydrophobic paint surface, the polytetrafluoroethylene nanoparticles form a columnar protruding structure on the photocurable resin film, the height value of the columnar protruding structure is 5-20 μm, the cross section of the columnar protruding structure is a square with a side length of 5-15 μm, and the distance between two adjacent columnar protruding structures is 10-50 μm.
Advantageous effects
The invention provides a quick preparation method of a super-hydrophobic paint surface, which has the advantages of simple and convenient process, large forming area, high preparation speed, wide application range and the like, and has good engineering application prospect.
Drawings
FIG. 1 is a first preparation flow diagram of a method for rapidly preparing a superhydrophobic paint surface according to one embodiment of the present invention;
FIG. 2 is a second flow chart of the method for rapidly preparing a superhydrophobic paint surface according to one embodiment of the present invention;
FIG. 3 is a schematic view showing a regular arrangement of pits formed in a photocurable resin film according to the present invention;
FIG. 4 is a schematic diagram of the formation of a columnar convex structure on the paint surface of the substrate by using the polytetrafluoroethylene nanoparticles of the present invention.
Detailed Description
Reference will now be made in detail to various exemplary embodiments of the invention, the detailed description should not be construed as limiting the invention but as a more detailed description of certain aspects, features and embodiments of the invention.
It is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. Further, for numerical ranges in this disclosure, it is understood that each intervening value, between the upper and lower limit of that range, is also specifically disclosed. Every smaller range between any stated value or intervening value in a stated range and any other stated or intervening value in a stated range is encompassed within the invention. The upper and lower limits of these smaller ranges may independently be included or excluded in the range.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although only preferred methods and materials are described herein, any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention. All documents mentioned in this specification are incorporated by reference herein for the purpose of disclosing and describing the methods and/or materials associated with the documents. In case of conflict with any incorporated document, the present specification will control.
It will be apparent to those skilled in the art that various modifications and variations can be made in the specific embodiments of the present disclosure without departing from the scope or spirit of the disclosure. Other embodiments will be apparent to those skilled in the art from consideration of the specification. The specification and examples are exemplary only.
As used herein, the terms "comprising," "including," "having," "containing," and the like are open-ended terms that mean including, but not limited to.
The "parts" referred to in the present invention are by mass unless otherwise specified.
The invention relates to a quick preparation method of a super-hydrophobic paint surface, which comprises the following steps:
step one, placing a photocuring resin film with a regular-shaped micron-scale rough surface structure in an aqueous solution of diethylene glycol diacrylate phthalate and sodium chloride for soaking for 3-20 min; positive charges are adsorbed on the photocurable resin film to improve the anti-sticking performance and the anti-sticking performance
Step two, taking out the photo-curing resin film, completely soaking the photo-curing resin film into 3-10% of polytetrafluoroethylene solution in parts by mass for 5-30min, and assembling polytetrafluoroethylene nanoparticles on the rough surface structure of the photo-curing resin film; preferably, the mass fraction of the polytetrafluoroethylene solution is 4% to 8%, more preferably 5% to 8%, for example 5%, 6%, 7% or 8%.
Thirdly, washing the photo-curing resin film obtained in the second step by using ultrapure water, and drying for 5-20 min;
and fourthly, stamping the rough surface structure of the light-cured resin film on the paint on the surface of the substrate, pressurizing and drying for 18-36h, and removing the light-cured resin film to obtain the super-hydrophobic paint surface.
In the above scheme, the rough surface structure of the photocurable resin film is a pit structure regularly arranged. The pit structure is a counter bore with a square cross section, the side length a of the square is 5-15 mu m, the depth value h of the counter bore is 5-20 mu m, and the distance value w between two adjacent counter bores is 10-50 mu m. Preferably, the sides a of the square are 7-15 μm, more preferably 9-12 μm, for example 9, 10, 11 or 12 μm; preferably, the depth value h of the counter bore is 7-18 μm, more preferably, the depth value h of the counter bore is 9-15 μm, for example, the depth value h of the counter bore is 9 μm, 10 μm, 11 μm, 12 μm, 13 μm, 14 μm or 15 μm; preferably, the pitch value w of two adjacent counter bores is 10-40 μm, more preferably 10-30 μm, for example, 10 μm, 12 μm, 14 μm, 16 μm, 17 μm, 18 μm, 19 μm, 20 μm, 23 μm, 25 μm, 27 μm, 28 μm, 29 μm or 30 μm.
In the above scheme, before the first step, the ultrasonic vibration is performed on the diethylene glycol diacrylate phthalate and the sodium chloride in advance for 10-30 min.
In the scheme, the mass part of the diethylene glycol diacrylate phthalate is 0.05-2.05%, and the concentration of the sodium chloride is 0.05 mmol/L. Preferably, the mass fraction of the phthalic acid diethylene glycol diacrylate is 0.05% to 1.85%, more preferably, the mass fraction of the phthalic acid diethylene glycol diacrylate is 0.05% to 1.05%, for example, the mass fraction of the phthalic acid diethylene glycol diacrylate is 0.05%, 0.07%, 0.08%, 0.1%, 0.15%, 0.2%, 0.3%, 0.4%, 0.55%, 0.65%, 0.7%, 0.85%, 0.9%, 1%, or 1.05%.
In the scheme, the step one and the step two also comprise the step of carrying out ultrasonic stirring on the polytetrafluoroethylene solution in advance for 30-60 min.
In the above scheme, the particle size of the polytetrafluoroethylene nanoparticle is 100-300 nm.
In the scheme, the paint on the surface of the substrate is fluorocarbon resin paint, and the thickness of the fluorocarbon resin paint is 40-150 μm.
In the scheme, the pressure drying condition in the fourth step is that the pressure value is 0.1-15g/mm2And drying at room temperature.
In the above scheme, in the fourth step, after the photocurable resin is removed, the polytetrafluoroethylene nanoparticles form a columnar protruding structure on the paint surface of the substrate, the height value H of the columnar protruding structure is preferably 5-20 μm, the cross section of the columnar protruding structure is a square with the side length a of 5-15 μm, and the distance value W between two adjacent columnar protruding structures is 10-50 μm. Preferably, the sides A of the square are 7-15 μm, more preferably, the sides A of the square are 9-12 μm, e.g., the sides A of the square are 9, 10, 11, or 12 μm; preferably, the depth value H of the counter bore is 7-18 μm, more preferably, the depth value H of the counter bore is 9-15 μm, for example, the depth value H of the counter bore is 9 μm, 10 μm, 11 μm, 12 μm, 13 μm, 14 μm or 15 μm; preferably, the pitch value W of two adjacent counter bores is 10-40 μm, more preferably 10-30 μm, for example, 10 μm, 12 μm, 14 μm, 16 μm, 17 μm, 18 μm, 19 μm, 20 μm, 23 μm, 25 μm, 27 μm, 28 μm, 29 μm or 30 μm.
Examples
Example 1
A method for quickly preparing a super-hydrophobic paint surface comprises the following steps:
firstly, carrying out ultrasonic vibration on the diethylene glycol diacrylate phthalate and the sodium chloride in advance for 20 min;
step two, placing the light-cured resin film with the pit structures in regular arrangement in 0.08 percent of phthalic acid diethylene glycol diacrylate aqueous solution and 0.05mmol/L sodium chloride aqueous solution for soaking for 5 min; the side length a of a square of the pit structure is 12 micrometers, the distance w is 11 micrometers, and the depth h is 9 micrometers;
step three, carrying out ultrasonic stirring on the polytetrafluoroethylene solution for 40 min;
taking out the light-cured resin film, completely soaking the light-cured resin film into 5% of polytetrafluoroethylene solution in parts by mass for 10min, and assembling polytetrafluoroethylene nanoparticles on the rough surface structure of the light-cured resin film; wherein the particle size of the polytetrafluoroethylene nano particles is 200nm
Washing the photo-curing resin film obtained in the step two by using ultrapure water, and drying for 5min in vacuum at 60 ℃;
sixthly, stamping the rough surface structure of the light-cured resin film on paint on the surface of a substrate, wherein the thickness of a paint film of the paint is 60 mu m, and the pressing is 1.2g/mm2And standing and drying for 24h, and removing the light-cured resin film to obtain the super-hydrophobic paint surface with the columnar convex structure. The side length A of the columnar protruding structures is 10 micrometers, the distance W is 10 micrometers, and the depth H is 8 micrometers. Contacting the surface with water at room temperatureThe angle is 152.3.
Example 2
A method for quickly preparing a super-hydrophobic paint surface comprises the following steps:
firstly, carrying out ultrasonic vibration on the diethylene glycol diacrylate phthalate and the sodium chloride in advance for 20 min;
step two, placing the light-cured resin film with the pit structures in regular arrangement in 0.08 percent of phthalic acid diethylene glycol diacrylate aqueous solution and 0.05mmol/L sodium chloride aqueous solution for soaking for 5 min; wherein the side length a of the square of the pit structure is 11 μm, the distance w is 12 μm, and the depth h is 12 μm;
step three, carrying out ultrasonic stirring on the polytetrafluoroethylene solution for 40 min;
taking out the light-cured resin film, completely soaking the light-cured resin film into 5% of polytetrafluoroethylene solution in parts by mass for 10min, and assembling polytetrafluoroethylene nanoparticles on the rough surface structure of the light-cured resin film; wherein the particle size of the polytetrafluoroethylene nano particles is 200 nm;
washing the photo-curing resin film obtained in the step two by using ultrapure water, and drying for 5min in vacuum at 60 ℃;
sixthly, stamping the rough surface structure of the light-cured resin film on paint on the surface of a substrate, wherein the thickness of a paint film of the paint is 60 mu m, and the pressing is 1.2g/mm2And standing and drying for 24h, and removing the light-cured resin film to obtain the super-hydrophobic paint surface with the columnar convex structure. The side length A of the columnar protruding structures is 10 micrometers, the distance W is 11 micrometers, and the depth H is 10.5 micrometers. The contact angle of the surface with water was 156.1 ° at room temperature.
It will be apparent to those skilled in the art that various modifications and variations can be made in the specific embodiments of the present disclosure without departing from the scope or spirit of the disclosure. Other embodiments will be apparent to those skilled in the art from consideration of the specification. The specification and examples are exemplary only.
Claims (9)
1. A method for quickly preparing a super-hydrophobic paint surface is characterized by comprising the following steps:
step one, placing a photocuring resin film with a regular-shaped micron-scale rough surface structure in an aqueous solution of diethylene glycol diacrylate phthalate and sodium chloride for soaking for 3-20 min;
step two, taking out the photo-curing resin film, completely soaking the photo-curing resin film into 3-10% of polytetrafluoroethylene solution in parts by mass for 5-30min, and assembling polytetrafluoroethylene nanoparticles on the rough surface structure of the photo-curing resin film;
thirdly, washing the photo-curing resin film obtained in the second step by using ultrapure water, and drying for 5-20 min;
fourthly, stamping the rough surface structure of the light-cured resin film on the paint on the surface of the substrate, drying for 18-36h under pressure, and removing the light-cured resin film to obtain the super-hydrophobic paint surface; after the light-cured resin film is removed, the polytetrafluoroethylene nanoparticles form columnar protruding structures on the paint surface of the substrate, the height value of each columnar protruding structure is 5-20 micrometers, the cross section of each columnar protruding structure is a square with the side length of 5-15 micrometers, and the distance value between every two adjacent columnar protruding structures is 10-50 micrometers.
2. The method for rapidly preparing the superhydrophobic paint surface according to claim 1, wherein the rough surface structure of the photocurable resin film is a pit structure regularly arranged.
3. The method for rapidly preparing the superhydrophobic paint surface according to claim 2, wherein the pit structure is a counter bore with a square cross section, the side length of the square is 5-15 μm, the depth value of the counter bore is 5-20 μm, and the distance value between two adjacent counter bores is 10-50 μm.
4. The method for rapidly preparing a superhydrophobic paint surface according to claim 1, wherein the first step further comprises the step of subjecting the diethylene glycol diacrylate phthalate and the sodium chloride to ultrasonic vibration for 10-30 min.
5. The method for rapidly preparing the superhydrophobic paint surface according to claim 1, wherein the mass portion of the phthalic acid diethylene glycol diacrylate is 0.05% -2.05%, and the concentration of the sodium chloride is 0.05 mmol/L.
6. The method for rapidly preparing the superhydrophobic paint surface according to claim 1, further comprising, between the first step and the second step, previously performing ultrasonic stirring on the polytetrafluoroethylene solution for 30-60 min.
7. The method for rapidly preparing the superhydrophobic paint surface according to claim 1, wherein the particle size of the polytetrafluoroethylene nanoparticles is 100-300 nm.
8. The method for rapidly preparing the superhydrophobic paint surface according to claim 1, wherein the paint on the surface of the substrate is fluorocarbon resin paint, and the thickness of the fluorocarbon resin paint is 40-150 μm.
9. The method for the rapid preparation of a superhydrophobic painted surface according to claim 1, wherein the pressure drying in the fourth step is performed under a pressure of 0.1-15g/mm2And drying at room temperature.
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CN111634881A (en) * | 2020-06-04 | 2020-09-08 | 清华大学 | Method for preparing underwater novel spanwise groove microstructure drag reduction surface |
CN111559396A (en) * | 2020-06-04 | 2020-08-21 | 清华大学 | Novel drag-reduction noise-reduction microstructure surface and preparation method thereof |
CN111633882A (en) * | 2020-06-04 | 2020-09-08 | 清华大学 | Method for constructing grid-shaped microstructure on surface of FEVE fluorocarbon resin |
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GB0922308D0 (en) * | 2009-12-22 | 2010-02-03 | Rolls Royce Plc | Hydrophobic surface |
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CN1775380A (en) * | 2005-11-18 | 2006-05-24 | 清华大学 | Method for forming superhydrophobic surface of solid material |
CN101479662A (en) * | 2006-06-30 | 2009-07-08 | E.I.内穆尔杜邦公司 | Printing form precursor and process for preparing a stamp from the precursor |
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