CN112745705B - Fluoropolymer nanoparticle modified photocuring fluorocarbon coating and preparation method thereof - Google Patents
Fluoropolymer nanoparticle modified photocuring fluorocarbon coating and preparation method thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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Abstract
The invention discloses a fluorine-containing polymer nanoparticle modified photo-cured fluorocarbon coating, which relates to the technical field of material surface protection and is mainly prepared from the following raw materials in percentage by mass: 5.0 to 10.0 percent of fluorine-containing polymer nano particles; 10.0 to 20.0 percent of fluorine-containing acrylate monomer; 30.0 to 40.0 percent of reactive acrylate oligomer; 20.0 to 30.0 percent of reactive acrylate reactive diluent; 10.0 to 15.0 percent of solvent; 0.5 to 3.5 percent of auxiliary agent; 5.0 to 10.0 percent of photoinitiator. The invention also provides a preparation method of the coating. The invention has the beneficial effects that: the paint is particularly suitable for a 3C electronic equipment touch screen, and a paint film obtained after the paint is cured has the characteristics of excellent weather resistance, good scrubbing resistance and excellent wear resistance, and simultaneously has an ultraviolet-proof function.
Description
Technical Field
The invention relates to the technical field of material surface protection, in particular to a fluorine-containing polymer nanoparticle modified photocuring fluorocarbon coating and a preparation method thereof.
Background
Contamination of the surface of materials is a common phenomenon in everyday life. The magnitude of the interaction between the contaminant and the surface of the material determines the strength of the contaminant's adhesion to the surface of the material. In order to improve the antifouling property of the material surface, an inert coating surface with low surface energy is prepared by using easy-to-clean resin. The easy-to-clean resin is widely applied to antifouling functional products such as marine antifouling coatings, novel antifouling textile fabrics, antifouling building finishing paints and the like. It can enrich the daily life of human beings and can clean and beautify the world of human beings.
In the use process of the 3C electronic product, the touch panel is easily contaminated by pollutants such as grease, sweat and the like on the skin of a human body in a naked use state. Fingerprints are different from general pollutants, and the chemical composition of the fingerprints is complex. A higher anti-fouling performance of the coating surface is required. The electronic product has high use frequency in daily life, and the surface of the coating is required to have hydrophobic and oleophobic anti-fouling and anti-fingerprint performances. The surface of the coating can also withstand the long-term wiping damage of the outside, and the long-acting easy-cleaning anti-fingerprint performance is kept.
The existing fluorine-containing anti-fingerprint coating often uses a large amount of fluorine-containing solvent, adopts a hot baking mode to form a film, and does not meet the requirement of environmental protection. In addition, after exposure to ultraviolet light, the hydrophobic and oleophobic properties are attenuated rapidly, and therefore, improvement on the fluorine-containing coating is needed, for example, patent publication No. CN102120914A discloses a fluorine-containing polymer nanoparticle modified ultraviolet-curable coating and a preparation method thereof. However, the fluorine-containing anti-fingerprint coating in the prior art has poor weather resistance and influences the use effect.
Disclosure of Invention
The invention aims to solve the technical problems that the fluorine-containing anti-fingerprint coating in the prior art has poor weather resistance and influences the use effect.
The invention solves the technical problems through the following technical means:
a fluorine-containing polymer nanoparticle modified photo-curing fluorocarbon coating is mainly prepared from the following raw materials in percentage by mass:
has the advantages that: the coating is particularly suitable for a 3C electronic equipment touch screen, and ultraviolet light or electron beam radiation is adopted to enable a paint film to generate photochemical polymerization reaction within a very short time of one second so as to realize curing. The paint film of the cured paint has the characteristics of excellent weather resistance, good scrubbing resistance and excellent wear resistance, and simultaneously has the function of ultraviolet resistance.
The raw materials of the coating have synergistic effect, and when the mass percent of the fluorine-containing polymer nano particles is not in the range, the friction performance of the coating is obviously reduced. The paint of the invention adopts short fluorocarbon chains, has no toxicity in components, does not need a fluorine-containing solvent, and does not pollute the environment.
Preferably, the method for preparing the fluoropolymer nanoparticles comprises the following steps: fluorine-containing acrylamide is taken as a raw material, trithiocarbonate-terminated polyethylene glycol, a cross-linking agent monomer, thiamine and a solvent are added, reaction is carried out for 24 hours at 42 ℃, and reactants are exposed to air to terminate the reaction, so that the fluorine-containing polymer nano particles are obtained.
Has the advantages that: the fluorine-containing polymer nano-particle uses the thiamine as a photocatalyst to generate excited-state substances which can provide or receive electrons from other substrates so as to mediate redox reaction to synthesize the polymer at high atomic efficiency at ambient temperature. The reaction condition is mild, no metal catalyst is used, the molecular weight difference is small, and the number average molecular weight is very close to a theoretical value.
The fluorine-containing polymer nano particles can realize long-acting hydrophobic and oleophobic effects and have the function of ultraviolet resistance. Compared with the patent with the publication number of CN102120914A, the fluorine-containing nano-particles with high molecular weight have high-selectivity adsorbability on fluorine-containing small molecular monomers, further improve the fluorine content of the surface of the coating, and solve the problem of reduced hydrophobic and oleophobic performances caused by the migration of the surface of short fluorocarbon chain molecules.
Preferably, the fluorine-containing acrylamide is N-perfluorohexylacrylamide.
Preferably, the crosslinker monomer is acryloyl ethylene diamine.
Preferably, the molar ratio of the fluorine-containing acrylamide to the trithiocarbonate-terminated polyethylene glycol to the crosslinker monomer to the thiamine is 1:0.1:1: 0.001.
Preferably, the preparation method of the fluorine-containing polymer nano-particles specifically comprises the following steps: 1mmol perfluorohexylacrylamide, 0.1mmol trithiocarbonate-capped polyethylene glycol, 1mmol crosslinker monomer, 0.001mmol phenothiazine and 10mL anhydrous ethanol were mixed, the mixed solution was deoxygenated and subjected to three freeze pump thawing cycles under nitrogen atmosphere, then irradiated with a white LED bulb, the temperature was maintained at 42 ℃ for 24 hours, and the reaction mixture was exposed to air to terminate the reaction.
Preferably, the fluorine-containing acrylate monomer comprises one or more of trifluoroethyl methacrylate, trifluoroethyl acrylate, hexafluorobutyl methacrylate, hexafluorobutyl acrylate, dodecafluoroheptyl methacrylate or dodecafluoroheptyl acrylate.
Preferably, the reactive acrylate reactive diluent comprises one or more of butyl acrylate, isooctyl acrylate, hydroxyethyl methacrylate, tripropylene glycol diacrylate, dipropylene glycol diacrylate, cumyl decyl acrylate, hexanediol diacrylate, pentaerythritol triacrylate, and dipentaerythritol triacrylate.
Preferably, the reactive acrylate oligomer comprises one or more of a hexa-functional urethane acrylate oligomer, a polyester acrylate oligomer and an epoxy modified acrylate oligomer.
Preferably, the solvent comprises one or more of butyl acetate, ethylene glycol methyl ether acetate, ethylene glycol butyl ether.
Preferably, the photoinitiator comprises one or more of acetophenone photoinitiator, 2-hydroxy-2-methyl-1-phenyl-1-acetone, 1-hydroxy-cyclohexyl-phenyl ketone, isopropyl thioxanthone and thiophenyl-p-oxazacycloacetone.
Preferably, the auxiliary agent includes a leveling agent, an antifoaming agent, or a wetting dispersant.
The invention also provides a preparation method of the fluorine-containing polymer nanoparticle modified photocuring fluorocarbon coating, which comprises the following steps:
(1) mixing a fluorine-containing acrylate monomer, a reactive acrylate oligomer, a reactive acrylate reactive diluent and a photoinitiator, heating to 50-60 ℃, and uniformly stirring;
(2) adding an auxiliary agent into the system in the step (1), and stirring until the auxiliary agent is dissolved;
(3) and (3) dissolving the fluorine-containing polymer nano-ions in a solvent, adding the solvent into the step (2), stirring, dispersing and filtering to obtain the fluorine-containing polymer nano-particle modified photocuring fluorocarbon coating.
Has the advantages that: the preparation method is simple, the components used in the preparation process are nontoxic, a fluorine-containing solvent is not needed, and the environment is not polluted.
The invention has the advantages that: the paint film of the cured paint has the characteristics of excellent weather resistance, good scrubbing resistance and excellent wear resistance, and simultaneously has the function of ultraviolet resistance.
The raw materials of the coating have synergistic effect, and when the mass percent of the fluorine-containing polymer nano particles is not in the range, the friction performance of the coating is obviously reduced. The paint of the invention adopts short fluorocarbon chains, has no toxicity in components, does not need a fluorine-containing solvent, and does not pollute the environment.
The preparation method is simple, the components used in the preparation process are nontoxic, a fluorine-containing solvent is not needed, and the environment is not polluted.
The fluorine-containing polymer nano-particle uses the thiamine as a photocatalyst to generate excited-state substances which can provide or receive electrons from other substrates so as to mediate redox reaction to synthesize the polymer at high atomic efficiency at ambient temperature. The reaction condition is mild, no metal catalyst is used, the molecular weight difference is small, and the number average molecular weight is very close to a theoretical value.
The fluorine-containing polymer nano particles can realize long-acting hydrophobic and oleophobic effects and have the function of ultraviolet resistance. The fluorine-containing nanoparticles have high-selectivity adsorbability on fluorine-containing micromolecule monomers, further improve the fluorine content of the coating surface, and solve the problem of reduced hydrophobic and oleophobic properties caused by the migration of the short fluorocarbon chain molecule surface.
Drawings
FIG. 1 is a hydrogen spectrum of fluoropolymer nanoparticles of example 1 of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Test materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
The specific techniques or conditions not specified in the examples can be performed according to the techniques or conditions described in the literature in the field or according to the product specification.
Example 1
The method for synthesizing the fluorine-containing polymer nano particles specifically comprises the following steps:
a50 mL flask equipped with a magnetic stir bar was charged with N-perfluorohexylacrylamide (1mmol), trithiocarbonate-capped polyethylene glycol (650mg, 0.1mmol), crosslinker monomer acryloyl ethylene diamine (1mmol), catalyst thiophene oxazine (0.6mg,0.001mmol) and 10mL absolute ethanol (EtOH). The solution was deoxygenated and subjected to three freeze pump thaw cycles under nitrogen and then irradiated with a white LED bulb, which was maintained at 42 ℃. After 24 hours, the reaction mixture was exposed to air to terminate the reaction. The nuclear magnetic resonance hydrogen spectrogram of the prepared fluorine-containing polymer nano particle is shown in figure 1.
The preparation principle is as follows: under the irradiation of visible light, phenothiazine substances are used as a photocatalyst to generate excited-state substances, and the excited-state substances can provide or accept electrons from other substrates so as to mediate redox reaction to synthesize polymers at high atomic efficiency at ambient temperature. The reaction condition is mild, no metal catalyst is used, the molecular weight difference is small, and the number average molecular weight is very close to a theoretical value.
Example 2
By using the photo-curable fluorocarbon coating modified by the fluoropolymer nanoparticles in example 1, the coating formulation components were in the proportions shown in table 1. The hexafunctional urethane acrylate oligomer in this example was purchased from Changxing corporation under the designation DRU 317.
Table 1 shows the raw material ratios in example 1
| Components | Ratio (%) |
| Fluoropolymer nanoparticles | 7.0％ |
| Trifluoroethyl methacrylate | 15.0％ |
| Hexafunctionality urethane acrylate oligomers | 35.0％ |
| Acrylic acid butyl ester | 25.0％ |
| Acetic acid butyl ester | 10.0％ |
| Leveling agent BYK345 | 3.0％ |
| 2-hydroxy-2-methyl-1-phenyl-1-propanone | 5.0％ |
The method specifically comprises the following steps:
(1) the components were weighed out in the proportions given in table 1.
(2) Mixing trifluoroethyl methacrylate, a hexa-functionality polyurethane acrylate oligomer, butyl acrylate and 2-hydroxy-2-methyl-1-phenyl-1-acetone, heating to 50 ℃, and uniformly stirring;
(3) adding a leveling agent BYK345 into the system in the step (2), and stirring until the leveling agent BYK345 is dissolved;
(4) and (3) dissolving the fluorine-containing polymer nano-ions in butyl acetate, adding the solution into the step (3), stirring, dispersing and filtering to obtain the fluorine-containing polymer nano-particle modified photocuring fluorocarbon coating.
When the photocuring fluorocarbon coating is applied, a photocuring light source is ultraviolet light or visible light, and the coating mode is spraying, roller coating, curtain coating or brush coating. The coating disclosed by the invention is simple in curing operation and convenient to construct, and can be effectively formed into a film by methods such as brushing, spraying and curtain coating. In the embodiment, ultraviolet light is adopted for curing, the coating mode is spraying, and the coating is atomized and uniformly sprayed on the surface of the base material by using high pressure. The thickness of the coating is 15-25 um.
Comparative example 1
The comparative example is different from example 2 in the weight percentage of each raw material, and is specifically shown in table 2.
Table 2 shows the proportions of the respective raw materials in comparative example 1
| Components | Ratio (%) |
| Fluoropolymer nanoparticles | 3.0％ |
| Hexafluorobutyl methacrylate | 15.0％ |
| Hexafunctionality urethane acrylate oligomers | 37.0％ |
| Acrylic acid butyl ester | 27.0％ |
| Acetic acid butyl ester | 10.0％ |
| Leveling agent BYK345 | 3.0％ |
| 2-hydroxy-2-methyl-1-phenyl-1-propanone | 5.0％ |
In the coating in the comparative example 1, ultraviolet light curing is adopted, the coating mode is spraying, and the spraying method is the same as that of the example 2.
The cured coatings of example 2 and comparative example 1 were tested for their performance, which is the prior art, and the results are shown in table 3.
Table 3 is a table of the results of the coating property tests of example 2 and comparative example 1
As can be seen from table 3, when the mass percentage of the fluoropolymer nanoparticles is less than 5%, the frictional properties of the coating are significantly reduced, the coating in example 2 is rubbed 5000 times under a load of 1kg, the initial hydrophobic angle is still above 105 °, the thickness loss is within 0.15mm, which indicates that the coating has an excellent fingerprint resistance function, the hydrophobic properties are not attenuated after 1000h of ultraviolet irradiation, while the coating in comparative example 1 is rubbed only 2000 times under a load of 1 kg.
Example 3
By using the photo-curable fluorocarbon coating modified by the fluoropolymer nanoparticles in example 1, the coating formulation was composed of the components in the proportions shown in table 4.
Table 4 shows the raw material ratios in example 3
The method specifically comprises the following steps:
(1) the components were weighed out in the proportions given in Table 4.
(2) Mixing dodecafluoroheptyl methacrylate, hexafunctionality polyurethane acrylate oligomer, ethylene glycol monobutyl ether and 2-hydroxy-2-methyl-1-phenyl-1-acetone, heating to 50 ℃, and uniformly stirring;
(3) adding a leveling agent BYK345 into the system in the step (2), and stirring until the leveling agent BYK345 is dissolved;
(4) and (3) dissolving the fluorine-containing polymer nano-ions in ethylene glycol monobutyl ether, adding into the step (3), stirring, dispersing and filtering to obtain the fluorine-containing polymer nano-particle modified photocuring fluorocarbon coating.
Comparative example 2
The comparative example is different from example 2 in the weight percentage of each raw material, and is specifically shown in table 5.
Table 5 shows the proportions of the respective raw materials in comparative example 2
In the coating in the comparative example 2, ultraviolet light curing is adopted in the example, the coating mode is spraying, and the spraying method is the same as that of the example 1.
The cured coatings of example 2 and comparative example 2 were tested for their performance, which is the prior art, and the results are shown in table 6.
Table 6 is a table of the results of the coating property tests of example 2 and comparative example 2
As can be seen from table 6, when the mass percentage of the fluoropolymer nanoparticles is greater than 10%, the frictional performance of the coating is significantly reduced, and the light transmittance is significantly reduced, and the thickness loss of the coating in example 2 is within 0.15mm after the coating is rubbed 5000 times under the load of 1kg, which indicates that the coating has an excellent fingerprint-resistant function, and the hydrophobic performance is not attenuated after the coating is subjected to ultraviolet irradiation for 1000h, whereas the coating in comparative example 1 is rubbed only 2000 times under the load of 1kg, and the transmittance is only 75%.
The above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.
Claims (10)
1. A fluorine-containing polymer nanoparticle modified photo-curing fluorocarbon coating is characterized in that: the material is mainly prepared from the following raw materials in percentage by mass:
the preparation method of the fluorine-containing polymer nano-particles comprises the following steps: the fluorine-containing acrylamide is used as a raw material, trithiocarbonate-terminated polyethylene glycol, a cross-linking agent monomer, phenothiazine and a solvent are added, and after reaction, reactants are exposed to the air to terminate the reaction, so that the fluorine-containing polymer nano particles are obtained.
2. The fluoropolymer nanoparticle-modified photocurable fluorocarbon coating according to claim 1, characterized in that: the preparation method of the fluorine-containing polymer nano-particles comprises the following steps: fluorine-containing acrylamide is taken as a raw material, trithiocarbonate-terminated polyethylene glycol, a cross-linking agent monomer, thiamine and a solvent are added, reaction is carried out for 24 hours at 42 ℃, and reactants are exposed to air to terminate the reaction, so that the fluorine-containing polymer nano particles are obtained.
3. The fluoropolymer nanoparticle-modified photocurable fluorocarbon coating according to claim 1, characterized in that: the fluorine-containing acrylamide is N-perfluorohexyl acrylamide.
4. The fluoropolymer nanoparticle-modified photocurable fluorocarbon coating according to claim 1, characterized in that: the cross-linking agent monomer is acryloyl ethylene diamine.
5. The fluoropolymer nanoparticle-modified photocurable fluorocarbon coating according to claim 1, characterized in that: the molar ratio of the fluorine-containing acrylamide to the trithiocarbonate-terminated polyethylene glycol to the cross-linking agent monomer to the thiamine is 1:0.1:1: 0.001.
6. The fluoropolymer nanoparticle-modified photocurable fluorocarbon coating according to claim 1, characterized in that: the preparation method of the fluorine-containing polymer nano-particle specifically comprises the following steps: 1mmol perfluorohexylacrylamide, 0.1mmol trithiocarbonate-capped polyethylene glycol, 1mmol crosslinker monomer, 0.001mmol phenothiazine and 10mL anhydrous ethanol were mixed, the mixed solution was deoxygenated and subjected to three freeze pump thawing cycles under nitrogen atmosphere, then irradiated with a white LED bulb, the temperature was maintained at 42 ℃ for 24 hours, and the reaction mixture was exposed to air to terminate the reaction.
7. The fluoropolymer nanoparticle-modified photocurable fluorocarbon coating according to claim 1, characterized in that: the fluorine-containing acrylate monomer comprises one or more of trifluoroethyl methacrylate, trifluoroethyl acrylate, hexafluorobutyl methacrylate, hexafluorobutyl acrylate, dodecafluoroheptyl methacrylate or dodecafluoroheptyl acrylate.
8. The fluoropolymer nanoparticle-modified photocurable fluorocarbon coating according to claim 1, characterized in that: the reactive acrylate reactive diluent comprises one or more of butyl acrylate, isooctyl acrylate, hydroxyethyl methacrylate, tripropylene glycol diacrylate, dipropylene glycol diacrylate, isopropyl methacrylate, hexanediol diacrylate, pentaerythritol triacrylate and dipentaerythritol triacrylate.
9. The fluoropolymer nanoparticle-modified photocurable fluorocarbon coating according to claim 1, characterized in that: the reactive acrylate oligomer comprises one or more of hexa-functionality polyurethane acrylate oligomer, polyester acrylate oligomer and epoxy modified acrylate oligomer.
10. A method for preparing the fluoropolymer nanoparticle-modified photocurable fluorocarbon coating of any one of claims 1-9, characterized by: the method comprises the following steps:
(1) mixing a fluorine-containing acrylate monomer, a reactive acrylate oligomer, a reactive acrylate reactive diluent and a photoinitiator, heating to 50-60 ℃, and uniformly stirring;
(2) adding an auxiliary agent into the system in the step (1), and stirring until the auxiliary agent is dissolved;
(3) and (3) dissolving the fluorine-containing polymer nano-ions in a solvent, adding the solvent into the step (2), stirring, dispersing and filtering to obtain the fluorine-containing polymer nano-particle modified photocuring fluorocarbon coating.
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