CN112694807B - Fluorine-silicon-containing coating composition and preparation method thereof - Google Patents
Fluorine-silicon-containing coating composition 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
- C09D143/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
- C09D143/04—Homopolymers or copolymers of monomers containing silicon
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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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
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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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
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Abstract
The present invention provides a fluorosilicone coating composition, the coating composition comprising: 30-75 parts of organic fluorine-silicon resin prepolymer, 15-35 parts of fluorine-silicon surfactant and 20-50 parts of fluorinated solvent, the coating composition has excellent water repellency, oil repellency and stain resistance, high hardness, good wear resistance and excellent adhesive force, can be widely applied to waterproof, oil-proof and antifouling occasions of glass surfaces, buildings, fabrics, leather, outdoor sculptures, advertisements, road signs and the like, and can also be applied to the fields of automobiles, buildings, aerospace and the like.
Description
Technical Field
The invention relates to a fluorine-silicon-containing coating composition, which belongs to a surface functional material in a new material industry contained in strategic emerging industry key products and service guide catalogues and belongs to the technical field of novel polymer antifouling materials.
Background
The fluorinated siloxane compound can form chemical crosslinks with the substrate surface to provide adhesion by hydrolytic condensation of siloxane groups, while fluorinated organic groups have a lower critical surface tension to provide stain resistance. However, the existing fluorine-silicon antifouling product has low polymer surface hardness, poor wear resistance and durability, or insufficient film forming, the adhesion between the product and a base material cannot meet the requirement, and a coating film can fall off after being slightly rubbed.
The invention patent with application number 201810793497.5 discloses a fluorine-containing super-hydrophilic self-cleaning coating, which can be added into a water-based coating to make the coating have high hydrophilic self-cleaning property and good adhesion with a substrate, but is only suitable for the water-based coating, and the mechanical properties of the water-based coating film, such as wear resistance and impact resistance, are poor, and only oil repellency and no water repellency exist, so that the application is limited.
The invention patent application No. 201910192216.5 discloses a surface antifouling treatment agent composition comprising fluorinated polyether siloxane, an amino group-containing fluorinated polyether compound and an inert fluorine oil, wherein the treatment agent forms a surface treatment layer having a static contact angle with water of 114 DEG and a friction durability of 18000 times, but the bonding force between the surface treatment layer and a substrate is general and the antifouling property is to be improved.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a fluorinated siloxane antifouling paint composition with excellent water repellency, oil repellency, stain resistance, wear resistance and binding power.
The technical scheme of the invention provides a fluorine-silicon-containing wear-resistant self-cleaning coating composition, which comprises the following components in parts by weight: 30-75 parts of organic fluorosilicone resin prepolymer, 5-10 parts of fluorosilicone surfactant and 20-50 parts of fluorinated solvent.
Wherein the preparation process of the organic fluorine-silicon resin prepolymer comprises the following steps: preparing a flask equipped with a stirrer, a thermometer, a condenser tube and a constant-pressure dropping funnel, heating in water bath, adding a polymerization monomer, a solvent and an initiator into the reactor under the protection of inert gas, stirring the mixture for 5-10min to completely dissolve the monomer and the initiator, and then heating to 60-70 ℃ for polymerization reaction for 5-10 h. And after the reaction is finished, cooling to room temperature, transferring the reaction mixed solution into a measuring flask, and evaporating to remove the solvent to obtain the organic fluorosilicone resin prepolymer.
Wherein the polymerized monomers comprise: 15-45wt.% fluorinated alkyl acrylate, 25-55wt.% fluoroalkene ether, 20-50wt.% unsaturated siloxane compound; fluorinated alkyl acrylate is CH2=CHCOOCH2(CF(CF3)CF2O)mOCF3M is an integer of 1 to 4, and fluoroalkene ether is CH2=CHCH2CF2O(CF(CF3)CF2O)nCF3N is an integer of 1 to 4, and the unsaturated siloxane compound is CH2=CHCH2CH2OSi(OCH3)3(ii) a Preferably, the fluorine-containing monomer accounts for 60wt.% to 80 wt.%, more preferably 72wt.% of the weight of the organic fluorosilicone prepolymer.
Wherein the initiator is AIBN or BPO; the solvent is one or more of toluene, ethyl acetate and methanol.
The organic fluorine-silicon prepolymer obtained by the preparation process has the following structural formula:
wherein a, b and c are integers of 1-3, and are the same or different; m and n are integers of 1-4, which are the same or different, and the number average molecular weight of the obtained organic fluorine-silicon resin prepolymer is 8000-50000.
The adopted fluorosilicone surfactant is perfluoroalkyl ether type silicon-containing surfactant, preferably INTECHEM-18, the fluorinated solvent is selected from hydrofluorocarbon and/or hydrofluorocarbon ether, and the hydrofluorocarbon is selected from CF3CFHCFHCF2CF3、CF3CF2CH2CH2F、C5F11H, hydrofluoro hydrocarbon ether selected from (CF)3)2CFOCH3、CH3O(CF2)4OCH3、C5F11OC2H5One or more of (a).
The invention also provides a preparation method of the fluorine-silicon-containing wear-resistant self-cleaning coating composition, which comprises the following steps: weighing the organic fluorine-silicon resin prepolymer, the fluorine-silicon surfactant and the fluorinated solvent according to the proportion, and fully and uniformly stirring in a reaction kettle to obtain the fluorine-silicon-containing wear-resistant self-cleaning coating composition. Preferably, the stirring rate is 500-.
Advantageous effects
Polymerized monomer fluorinated alkyl acrylate CH of organic fluorine-silicon prepolymer2=CHCOOCH2(CF(CF3)CF2O)mOCF3Fluoroolefin ether CH2=CHCH2CF2O(CF(CF3)CF2O)nCF3The long-chain fluoroalkyl structure is provided, and the chain length, content, stacking state and main chain composition of the side chain fluoroalkyl in the fluorine-containing group play a decisive role in the oil-proof and water-proof performance.
The organic fluorine has strong electron-withdrawing property, and the electrostatic influence is weakened, so that the coating is not easy to accumulate dirt, the dirt accumulation is slowed down, or accumulated floating dirt is easy to clean by natural wind and rain. The structure enables the coating to have extremely low surface free energy, endows the base material with good water repellency and oil repellency, and excellent performances such as weather resistance, ageing resistance, solvent resistance and chemical corrosion resistance, along with the increase of the content of the fluorine monomer, the longer the fluoroalkyl chain is, the tail ends of the fluoroalkyl chains can be directionally and regularly arranged on the surface of the base material due to intermolecular action (Van der Waals force and hydrophobic effect), the better the waterproof, oil-proof and anti-pollution performances of the fluorosilicone resin prepolymer are, but when the content of the fluorine monomer reaches a threshold value, the content of the fluorine monomer is increased, the improvement degree of the waterproof, oil-proof and anti-pollution performances of the coating is lower, and the overlong fluoroalkyl chain can cause a steric hindrance effect between the fluorosilicone resin prepolymers, is not beneficial to the directional arrangement (tail end orientation) of the fluoroalkyl chain, and the waterproof, oil-proof and anti-pollution performances of the coating can be reduced on the contrary. Through research, when m and n are determined to be between 1 and 4, preferably, the content of the fluorine-containing monomer accounts for 60wt.% to 80 wt.% of the weight of the organic fluorine-silicon prepolymer, more preferably 75 wt.%, and the number average molecular weight of the organic fluorine-silicon resin prepolymer is between 8000 and 50000, the organic fluorine-silicon prepolymer can achieve the best water repellency, oil repellency and anti-fouling performance.
The fluorine-containing acrylate has excellent performance, but the price is high, and the application range of the copolymer is influenced by using a large amount of the fluorine-containing acrylate. Relatively low-priced organosilicon, unsaturated siloxane monomer CH2=CHCH2CH2OSi(OCH3)3The organic silicon monomer has lower surface energy, the provided organic silicon monomer has outstanding water repellent effect, the introduction of the organic silicon monomer can also reduce the dosage of the fluorine-containing monomer, the unsaturated siloxane monomer can also be used as a self-crosslinking agent and is introduced into a fluorine-containing acrylate main chain structure in a copolymerization way, when the obtained fluorine-containing silicon copolymer coating composition acts on the surface of a substrate, the fluorine-containing silicon copolymer coating composition is connected with the substrate through a silicon-oxygen covalent bond, the outermost layer is a fluorine-containing group, a new surface layer of fluorine atoms or atomic groups is formed on the surface of the substrate, and oil and water can not wet the new surface layer by virtue of the chemical force of the fluorine atoms or atomic groups of the new surface layer, so that the water repellent property and the adhesive force of a coating film are further improved.
The fluorosilicone surfactant adopted by the invention is a perfluoroalkyl ether silicon-containing surfactant which has excellent interface wetting, spreading and dispersing properties, preferably INTECHEM-18 with ultra-low surface tension and can be decomposed into coupling groups and hydrophobic and oleophobic groups of fluorine chains, and the surfactant and the organic fluorosilicone prepolymer have synergistic effect, so that the adhesive effect between the resin prepolymer and the surface of the base material can be improved, the waterproof and oil-proof effects of the coating can be further improved, and a good effect can be achieved at low consumption.
Compared with other organic solvents, the hydrofluorocarbon/hydrofluorocarbon ether has lower surface tension and viscosity, has weaker requirements on the properties of the base material, can obtain a continuous, uniform and pore-free coating even if the surface shape of the base material is complex, does not degrade resin and has poorer water solubility compared with the common ketone and ester solvents, and can prevent the coating composition from generating gel due to the hydrolysis of silane monomer units in the copolymer, so the obtained coating composition has higher storage stability. Hydrofluorocarbons, preferably CF3CFHCFHCF2CF3、CF3CF2CH2CH2F、C5F11One or more of H, hydrofluoro hydrocarbon ether is preferably (CF)3)2CFOCH3、CH3O(CF2)4OCH3、C5F11OC2H5One or more of (a).
The fluorinated siloxane antifouling paint composition provided by the invention is widely applied and is suitable for waterproof, oil-proof and antifouling occasions of glass surfaces, buildings, fabrics, leather, outdoor sculptures, advertisements, road signs and the like.
Drawings
FIG. 1 shows the states of the droplets of distilled water (a), corn oil (b) and red wine (c) on the glass surface coated with paint a;
FIG. 2 shows the state of droplets of distilled water (a), corn oil (b) and red wine (c) on the surface of glass coated with a commercially available coating;
FIG. 3 shows the states of the droplets of distilled water (a), corn oil (b) and red wine (c) on the glass surface without coating.
Detailed Description
The invention is further described below with reference to the drawings and specific preferred embodiments of the description, without thereby limiting the scope of protection of the invention.
Example 1
One kind containsThe fluorine-silicon coating composition comprises the following raw materials in parts by weight: 35 parts of organic fluorine-silicon resin prepolymer, INTECHEM-1815 parts, CF3CFHCFHCF2CF3 And 25 parts. The organic fluorine-silicon prepolymer has the following structural formula:
wherein a, b and c are all 1, m is 1, n is 2, and the number average molecular weight is 10000.
Example 2
The fluorine-containing silicon coating composition comprises the following raw materials in parts by weight: 50 parts of organic fluorine silicone resin prepolymer, INTECHEM-1820 parts, CF3CFHCFHCF2CF3 30 parts of. The organic fluorine-silicon prepolymer has the following structural formula:
wherein a is 1, b is 2, c is 1, m is 4, n is 3, and the number average molecular weight is 20000.
Example 3
The fluorine-containing silicon coating composition comprises the following raw materials in parts by weight: 65 parts of organic fluorine-silicon resin prepolymer, 1830 parts of INTECHEM-1830 parts of CF3CFHCFHCF2CF3 50 parts of the raw materials. The organic fluorine-silicon prepolymer has the following structural formula:
wherein a is 3, b is 1, c is 2, m is 2, n is 1, and the number average molecular weight is 35000.
Comparative example 1
The composition of the starting material was the same as that of example 1 except that the starting material of the resin prepolymer contained no fluorinated alkyl acrylate CH2=CHCOOCH2(CF(CF3)CF2O)mOCF3。
Comparative example 2
The composition of the raw material was the same as that of example 1 except that the raw material of the resin prepolymer did not contain the fluorine-containing olefin ether CH2=CHCH2CF2O(CF(CF3)CF2O)nCF3。
Comparative example 3
The same composition as that of the raw material in example 1 was used except that the unsaturated siloxane compound CH was not contained in the raw material of the resin prepolymer2=CHCH2CH2OSi(OCH3)3。
Comparative example 4
The organic fluorosilicone prepolymer in example 1 was replaced with a commercially available SiFast SF-335 fluorosilicone polymer, and the remaining raw materials and amount of the composition were unchanged.
Comparative example 5
The surface of the glass substrate without paint spray was blank.
The preparation method of the fluorine-containing silicon coating composition comprises the following steps: the organic fluorosilicone resin prepolymer, the fluorosilicone surfactant and the fluorinated solvent are weighed according to the mixture ratio of the examples 1 to 3 and the comparative examples 1 to 4, and are fully and uniformly stirred in a reaction kettle to obtain the fluorosilicone coating composition (named as coating a, coating b, coating c, coating d, coating e, coating f and coating g respectively), wherein the stirring speed is about 600rpm, and the stirring time is about 30 minutes.
Cleaning the surface of the toughened glass, then uniformly spraying the coating composition on the pretreated glass surface through a spraying device, standing for 24-48 hours at room temperature, and curing to form a fluorine-containing silicon coating, wherein the thickness of the coating is controlled to be 0.1-10 mu m.
And (3) testing the waterproof, oil-proof and antifouling performances: the contact angle was measured by dropping 10. mu.L droplets (distilled water, corn oil and red wine) onto the surface of the substrate, and taking 5 different points for each sample, and averaging to obtain the contact angle. The results are shown in FIGS. 1-3 and Table 1.
And (3) wear resistance test: steel wool (contact area 1 mm. times.1 mm) was placed on the surface of the glass substrate, a load of 1Kgf was applied thereto, and then the steel wool was subjected to a rubbing treatment at a wiping speed of 50 cycles/min. The results are shown in Table 1.
And (3) testing the adhesive force: the lines are drawn at a distance of 1mm and 10 multiplied by 10 squares, and are adhered by an adhesive tape without falling off, which is referred to the standard GB/T9286. The results are shown in Table 1.
And (3) hardness testing: the maximum hardness was measured using a 750g pencil hardness tester, Mitsubishi pencil, reference standard GB/T6739, and the results are given in Table 1.
Table 1 shows the results of the tests for the formation of the coatings of the examples and comparative examples.
From the above characterization results, it can be seen that the fluorosilicone coating compositions (examples 1-3) provided by the present invention have better water repellency, oil repellency and stain resistance than coating compositions lacking the necessary fluorine/silicone monomer resin prepolymer (comparative examples 1-3), and compared with commercially available fluorosilicone coating compositions (comparative example 4) and uncoated substrate surfaces (comparative example 5), and have high hardness, better abrasion resistance and excellent adhesion, and can be widely applied to various occasions.
The above is only a specific embodiment of the present invention, but the technical features of the present invention are not limited thereto. Any simple changes, equivalent substitutions or modifications made on the basis of the present invention to solve the substantially same technical problems and achieve the substantially same technical effects are within the scope of the present invention.
Claims (11)
1. A fluorosilicone coating composition, comprising in parts by weight:
(1) 30-75 parts of organic fluorine-silicon resin prepolymer, wherein the organic fluorine-silicon prepolymer has the following structural formula:
(2) 15-35 parts of a fluorosilicone surfactant;
(3) 20-50 parts of a fluorinated solvent;
the preparation process of the organic fluorosilicone resin prepolymer comprises the following steps: preparing a flask provided with a stirrer, a thermometer, a condenser tube and a constant-pressure dropping funnel, heating in a water bath, adding a polymerization monomer, a solvent and an initiator into a reactor under the protection of inert gas, stirring a mixed system for 5-10min to completely dissolve the monomer and the initiator, then heating to 60-70 ℃, and carrying out polymerization reaction for 5-10 h; after the reaction is finished, cooling to room temperature, transferring the reaction mixed solution into a measuring flask, and evaporating to remove the solvent to obtain the organic fluorosilicone resin prepolymer; the polymerized monomers include: 15-45wt.% fluorinated alkyl acrylate, 25-55wt.% fluoroalkene ether, 20-50wt.% unsaturated siloxane compound.
2. The fluorosilicone coating composition of claim 1, wherein the fluoromonomer is present in an amount of from 60wt.% to 80 wt.% based on the weight of the organofluorosilicone prepolymer.
3. The fluorosilicone coating composition of claim 2, wherein the fluoromonomer is present in an amount of 72wt.% based on the weight of the organofluorosilicone prepolymer.
4. The fluorosilicone coating composition of any one of claims 1 to 3, wherein the initiator is AIBN or BPO; the solvent is one or more of toluene, ethyl acetate and methanol.
5. The fluorosilicone coating composition of any one of claims 1 to 3, wherein the fluorinated alkyl acrylate is CH2=CHCOOCH2(CF(CF3)CF2O)mOCF3M is an integer of 1 to 4; the fluoroalkene ether is CH2=CHCH2CF2O(CF(CF3)CF2O)nCF3N is an integer of 1 to 4; the unsaturated siloxane compound is CH2=CHCH2CH2OSi(OCH3)3。
6. The fluorosilicone coating composition according to claim 1, wherein the fluorosilicone surfactant is a perfluoroalkyl ether type silicon-containing surfactant.
7. The fluorosilicone coating composition of claim 6, wherein said fluorosilicone surfactant is INTECHEM-18.
8. The fluorosilicone coating composition of claim 1, wherein said fluorinated solvent is selected from the group consisting of hydrofluorocarbons and/or hydrofluorocarbon ethers.
9. The fluorosilicone coating composition of claim 8, wherein said hydrofluorocarbon is selected from the group consisting of CF3CFHCFHCF2CF3、CF3CF2CH2CH2F、C5F11One or more of H; said hydrofluorohydrocarbon ether is selected from (CF)3)2CFOCH3、CH3O(CF2)4OCH3、C5F11OC2H5One or more of (a).
10. A method for producing the fluorine-containing silicon coating composition according to any one of claims 1 to 9, characterized by comprising the steps of: weighing the organic fluorine-silicon resin prepolymer, the fluorine-silicon surfactant and the fluorinated solvent according to the proportion, and fully and uniformly stirring in a reaction kettle to obtain the fluorine-silicon-containing coating composition.
11. The method for preparing fluorine-containing silicon coating composition according to claim 10, wherein the stirring speed is 500-800rpm and the stirring time is 20-60 minutes.
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Citations (4)
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| JPH09208896A (en) * | 1996-01-30 | 1997-08-12 | Dainippon Toryo Co Ltd | Binder for inorganic/organic composite coating agent |
| CN1474837A (en) * | 2000-11-16 | 2004-02-11 | 3M创新有限公司 | Water-repellent, or-repellent and soil resistant coating composition |
| CN104804148A (en) * | 2015-05-05 | 2015-07-29 | 湖南晟通纳米新材料有限公司 | Fluorosilicone acrylate emulsion and preparing method of fluorosilicone acrylate emulsion |
| CN111234237A (en) * | 2020-03-11 | 2020-06-05 | 东莞泰岳光学镀膜材料有限公司 | Perfluoropolyether modified polysiloxane coating auxiliary agent, preparation method thereof and coating |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09208896A (en) * | 1996-01-30 | 1997-08-12 | Dainippon Toryo Co Ltd | Binder for inorganic/organic composite coating agent |
| CN1474837A (en) * | 2000-11-16 | 2004-02-11 | 3M创新有限公司 | Water-repellent, or-repellent and soil resistant coating composition |
| CN104804148A (en) * | 2015-05-05 | 2015-07-29 | 湖南晟通纳米新材料有限公司 | Fluorosilicone acrylate emulsion and preparing method of fluorosilicone acrylate emulsion |
| CN111234237A (en) * | 2020-03-11 | 2020-06-05 | 东莞泰岳光学镀膜材料有限公司 | Perfluoropolyether modified polysiloxane coating auxiliary agent, preparation method thereof and coating |
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