JPH0136869B2 - - Google Patents

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention relates to a fluorine-based paint that has good adhesive properties, particularly to inorganic materials such as metals. [Prior Art] Paints with excellent weather resistance and durability are required for the exterior of buildings, vehicles, ships, aircraft, etc., and high-quality polyester or acrylic exterior paints are used. However, existing paints have a short outdoor service life, and even the above-mentioned high-quality paints lose their aesthetic appearance and substrate protection effect within a few years. On the other hand, fluorine-based polymers are extremely stable both thermally and chemically, and have excellent weather resistance, water resistance, chemical resistance, solvent resistance, mold releasability, low friction, and water repellency. , suitable as a surface treatment agent for various substrates. However, conventionally known fluorine-based polymers suffer from the above-mentioned properties and are difficult to dissolve in organic solvents and form a coating film, making them extremely difficult to use as paints. For example, most of the currently known fluoropolymer paints are powder paints, and only a few
PVdF (polyvinylidene fluoride) is simply used as an organic solvent-dispersed paint by taking advantage of its ability to dissolve in specific solvents at high temperatures. Moreover, these fluoropolymer paints require baking at a high temperature when forming a film, so their field of use is limited to areas where heating equipment is available. Furthermore, the presence of heating equipment and the baking process are not desirable from the viewpoint of the safety of workers and the environment of the workplace. Therefore, in recent years, attempts have been made to develop fluorine-based polymers that are soluble in solvents or do not require a baking process at high temperatures. For example, Japanese Patent Application Laid-open No. 57-34107 describes fluoroolefin, cyclohexyl vinyl ether,
A quaternary copolymer consisting of an alkyl vinyl ether and a hydroxyalkyl vinyl ether is disclosed, the copolymer being soluble in an organic solvent and comprising:
It is also described that it can be cured at room temperature. In addition, a patent application filed by the present applicant in Japanese Patent Application No. 59-263017 discloses a three-dimensional compound consisting of a fluoroolefin, a vinyl ether, an organosilicon compound having an olefinic unsaturated bond and a hydrolyzable group.
The original copolymer is disclosed, and it is described that this copolymer is also soluble in organic solvents and can be cured at room temperature. However, when these fluoropolymers are dissolved in an organic solvent and used as a paint, the film formed on the base material has excellent weather resistance, chemical resistance, and low friction, but it does not interact with the base material. There is a problem of poor adhesion, especially to inorganic substrates such as metals.
For this reason, when applying the above-mentioned paint onto a base material, a method is used in which a primer layer is formed on the surface of the base material in advance and the primer layer is coated thereon. However, with this method, the painting work is complicated, and although the fluoropolymer film has good properties, the presence of a primer layer conversely reduces its solvent resistance and weather resistance. However, it also causes poor durability of the film. [Problems to be Solved by the Invention] In view of this situation, the present inventors developed a solution-type fluorine-based system that does not require a primer layer and can be cured at room temperature and has good adhesive strength even when applied directly onto a base material. The present invention was arrived at after repeated studies on how to obtain paints. [Means for solving the problems] That is, the present invention provides (a) a fluoroolefin;
(b) a vinyl ether, and (c) an organic silicon compound having an olefinic unsaturated bond and a hydrolyzable group; This is a fluorine-based paint characterized by dissolving in an organic solvent. [Function] The fluorine-based polymer, which is the main component of the fluorine-based paint of the present invention, can be cured at room temperature and has the property of being soluble in organic solvents. Fluorinated polymers with such properties contain fluoroolefin and vinyl ether as essential monomer components, and can be cured by a crosslinking reaction at room temperature in the presence or absence of a curing agent or curing accelerator catalyst. It also contains monomer components with organic functional groups. A more specific example of such a fluorine-based polymer includes the following polymer [A]. [A] A copolymer consisting essentially of (a) a fluoroolefin, (b) a vinyl ether, and (c) an organosilicon compound having an olefinic unsaturated bond and a hydrolyzable group; Combining (a)
(a): 30 to 70 mol%, (b): 20 to 60 mol%, (c): 1 to 25 mol%, with respect to the total number of moles of ~(c), and gel permeation The number average molecular weight (n) measured by chromatography is
3000 to 200,000 fluorine-based polymer, where the fluorine-based polymer [A] is a random copolymer consisting of at least the three types of monomer component units (a), (b), and (c) mentioned above. It is. However, within a range that does not impair the purpose of the present invention, small amounts of other copolymerizable monomer components, such as α-olefins,
Cycloolefins, unsaturated carboxylic acids, etc. may be copolymerized. Fluoroolefin (a), which is a monomer component constituting the fluoropolymer [A], has at least one fluorine atom in the molecule, and preferably all hydrogen atoms of the olefin are fluorine atoms and Perhaloolefins substituted with other halogen atoms are preferred. Furthermore, from the viewpoint of polymerizability and properties of the produced polymer, the number of carbon atoms is 2 or 3.
fluoroolefins are preferred. Examples of such fluoroolefins include CF ₂
= CF ₂ , CHF = CF ₂ , CH ₂ = CF ₂ , CH ₂ = CHF,
CClF=CF ₂ , CHCl=CF ₂ , CCl ₂ =CF ₂ , CClF=
CClF, CHF= _CCl2 , _CH2 =CClF, _CCl2 =CClF
Fluoroethylene series such as CF ₃ CF=CF ₂ , CF ₃ CF
= CHF, CF ₃ CH = CF ₂ , CF ₃ CH = CH ₂ ,
CHF ₂ CF=CHF, CF ₃ CH=CH ₂ , CH ₃ CF=CF ₂ ,
CH ₃ CH=CF ₂ , CH ₃ CF=CH ₂ , CF ₂ ClCF=CF ₂ ,
CF ₃ CCl=CF ₂ , CF ₃ CF=CFCl, CF ₂ ClCCl=
CF ₂ , CF ₂ ClCF=CFCl, CFCl ₂ CF=CF ₂ ,
CF ₃ CCl=CClF, CF ₃ CCl=CCl ₂ , CClF ₂ CF=
CCl ₂ , CCl ₃ CF=CF ₂ , CF ₂ ClCCl=CCl ₂ ,
CFCl ₂ CCl=CCl ₂ , CF ₃ CF=CHCl, CClF ₂ CF=
CHCl, CF ₃ CCl=CHCl, CHF ₂ CCl=CCl ₂ ,
CF ₂ ClCH=CCl ₂ , CF ₂ ClCCl=CHCl, CCl ₃ CF=
CHCl, CF ₂ ICF=CF ₂ , CF ₂ BrCH=CF ₂ ,
CF ₃ CBr=CHBr, CF ₂ ClCBr=CH ₂ , CH ₂ BrCF
=CCl ₂ , CF ₃ CBr=CH ₂ , CF ₂ CH=CHBr,
CF ₂ BrCH=CHF, CF ₂ BrCF=fluoropropene such as CF ₂ , CF ₃ CF ₂ CF=CF ₂ , CF ₃ CF=
CFCF ₃ , CF ₃ CH=CFCF ₃ , CF ₂ = CFCF ₂ CHF ₂ ,
CF ₃ CF ₂ CF=CH ₂ , CF ₃ CH=CHCF ₃ , CF ₂ =
CFCF ₂ CH ₃ , CF ₂ = CFCH ₂ CH ₃ , CF ₃ CH ₂ CH =
CH ₂ , CF ₃ CH=CHCH ₃ , CF ₂ =CHCH ₂ CH ₃ ,
CH ₃ CF ₂ CH=CH ₂ , CFH ₂ CH=CHCFH ₂ ,
CH ₃ CF ₂ CH=CH ₃ , CH ₂ = CFCH ₂ CH ₃ , CF ₃
(CF ₂ ) ₂ CF=CF ₂ , CF ₃ (CF ₂ ) ₃ CF=CF ₂ , and other fluoroolefin systems having 4 or more carbon atoms can be mentioned. Among these, as mentioned above, fluoroethylene and fluoropropene are preferred, particularly tetrafluoroethylene (CF ₂ = CF ₂ ), chlorotrifluoroethylene (CFCl = CF ₂ ) and hexafluoropropene (CF ₂ = CFCF _{3 )} . ) are preferred, and from the standpoint of safety and ease of handling, hexafluoropropene and chlorotolylfluoroethylene are more preferred. Further, in the present invention, it goes without saying that the fluoroolefin may be used alone or in combination. Vinyl ether (b) is a vinyl group, an alkyl (including cycloalkyl) group, an aryl group,
It is a compound in which an aralkyl group or the like is bonded to an ether, and among them, an alkyl vinyl ether, in particular, the number of carbon atoms is 8 or less, preferably 2 to 2.
An alkyl vinyl ether bonded to the alkyl group of No. 4 is preferred. Furthermore, alkyl vinyl ethers in which the alkyl group is in the form of a chain are most preferred. Examples of such vinyl ethers include ethyl vinyl ether, propyl vinyl ether, isopropyl vinyl ether, butyl vinyl ether,
tert-butyl vinyl ether, pentyl vinyl ether, hexyl vinyl ether, isohexyl vinyl ether, octyl vinyl ether, 4-
Chain alkyl vinyl ethers such as methyl-1-pentyl vinyl ether, cycloalkyl vinyl ethers such as cyclopentyl vinyl ether and cyclohexyl vinyl ether, aryl vinyl ethers such as phenyl vinyl ether, o-, m-, p-trivinyl ether, benzyl vinyl ether, Aralkyl vinyl ethers such as enethyl vinyl ether can be mentioned. Among these, linear alkyl vinyl ethers and cycloalkyl vinyl ethers are particularly preferred, and ethyl vinyl ether, propyl vinyl ether, and butyl vinyl ether are particularly preferred. Further, in the present invention, it goes without saying that the vinyl ether may be used alone or in a mixture of two or more vinyl ethers. The organosilicon compound (c) may be one having an olefinic unsaturated bond and a hydrolyzable group in the molecule, and specifically, those shown in the following general formulas (1) to (3) are exemplified. can do. R ¹ R ² SiY ¹ Y ² (1) R ¹ XSiY ¹ Y ² (2) R ¹ SiY ^{1 Y} 2 Y ³ (3) (In the formula, R ¹ and R ² have olefinic unsaturated bonds and , hydrogen and optionally oxygen, each of which is the same or different; X is an organic group having no olefinic unsaturated bond; Y ¹ , Y ² , Y ³ are each the same or different hydrolyzable ) More specific examples of R ¹ and R ² include vinyl,
Examples include allyl, butenyl, cyclohexenyl, and cyclopentadienyl, and terminal olefinic unsaturated groups are particularly preferred. Other preferred examples include CH ₂ =CH—O—(CH ₂ ) ₃ —, CH ₂ =C(CH ₃ ) having an ester bond of a terminal unsaturated acid.
COO(CH ₂ ) ₃ ―, CH ₂ =C(CH ₃ )COO(CH ₂ ) ₂ ―
O-( _CH2 ) _3- , Examples include groups such as. Among these, vinyl groups are most suitable. Specific examples of X include monovalent hydrocarbon groups such as methyl, ethyl, propyl, tetradecyl, octadecyl,
Groups include phenyl, benzyl, tolyl, etc., and these groups may also be halogen-substituted hydrocarbon groups. Specific examples of Y ¹ , Y ² , and Y ³ include alkoxy groups such as methoxy, ethoxy, butoxy, and methoxyethoxy, alkoxyalkoxy groups, acyloxy groups such as formyloxy, acetoxy, and propionoxy, and oximes such as -ON=C (CH ₃ ) ₂ , -ON=CHCH ₂ C ₂ H ₅ and -ON=C(C ₆ H ₅ ) ₂ , or substituted amino groups and arylamino groups such as -NHCH ₃ , -
NHC ₂ H ₅ and -NH (C ₆ H ₅ ), and any other hydrolyzable organic group. The organosilicon compound preferably used in the present invention is a compound represented by the general formula (3), and an organosilicon compound in which the groups Y ¹ , Y ² , and Y ³ are the same is particularly suitable. Among these, it is preferable that R ¹ is a vinyloxyalkyl group (CH ₂ =CH—O—(CH ₂ ) _o —) or a vinyl group, and Y ¹ to ^{Y 3} are an alkoxy group or an alkoxyalkoxy group. Roxypropyltrimethoxysilane, vinyltrimethoxylane, vinyltriethoxysilane,
Examples include vinyltris(methoxyethoxy)silane. However, vinylmethyldiethoxysilane, vinylphenyldimethoxysilane, etc. can be used as well. The content ratio of the monomer components (a) to (c) in the fluorine-based polymer [A] is (a): 30 to 70 mol%, (b) based on the total number of moles of (a) to (c). ): 20 to 60 mol%,
(c): 1 to 25 mol% ((a) + (b) + (c) = 100), mostly (a): 40 to 60 mol%, (b): 20 to 50 mol%, ( c)：
It is in the range of 5 to 20 mol%. The molecular weight is determined by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent and monodisperse polystyrene of known molecular weight as a standard substance, and the number average molecular weight (n) is usually 3000 to 200000, often 5000
~100000 range. By adopting such a composition ratio and molecular weight, it becomes solvent soluble and has excellent film coating properties, and after being cured by the method described below, it has excellent solvent resistance, chemical resistance, weather resistance, heat resistance, and mechanical resistance. It has excellent physical properties. Another property of the fluoropolymer [A] is that it is amorphous or has low crystallinity, and is often amorphous. In general, the degree of crystallinity by X-rays is 0%,
In many cases, the melting point cannot be observed using differential scanning calorimetry (DSC). Therefore, transparency is good. The glass transition temperature (Tg) is usually -60 to +20°C, often -40 to +5 when measured by DSC at a heating rate of 10°C/min after cooling the sample to -120°C.
in the range of ℃. An optical property is the refractive index ( _nD ), which is usually
1.48-1.34, mostly in the 1.44-1.36 range. The fluoropolymer can be produced by copolymerizing each of the monomers (a) to (c) detailed above in the presence of a well-known radical initiator. Here, each component (a) to (c) is important; for example, copolymerization does not occur with components (a) and (c) alone, but
By adding component (b), components (a), (b), and (c) are copolymerized. Various known radical initiators can be used for copolymerization. Specifically, organic peroxides, organic peresters such as benzoyl peroxide, dichlorobenzoyl peroxide,
Dicumyl peroxide, di-tert-butyl peroxide, 2,5-dimethyl-2,5-di(peroxybenzoate) hexyne-3,1,4-bis(tert-butylperoxyisopropyl)benzene, lauroyl peroxide, tere-butyl Peracetate, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexyne-3,2,
5-dimethyl-2,5-di(tert-butylperoxy)hexane, tert-butyl perbenzoate, tert-butyl perphenylacetate, tert
-butyl perisobutyrate, tert-butyl per-sec-octoate, tert-butyl perpivalate, cumyl perpivalate, tert-butyl perdiethyl acetate, and other azo compounds such as azobis-isobutylnitrile, dimethyl azoisobutyrate and so on. Among these, dicumyl peroxide, di-tert-butyl peroxide, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexyne-3,2,5-dimethyl-2,5-di(tert- Dialkyl peroxides such as butylperoxy)hexane and 1,4-bis(tert-butylperoxyisopropyl)benzene are preferred. The copolymerization takes place in a reaction medium consisting of an organic solvent. The solvents used here include aromatic hydrocarbons such as benzene, toluene, and xylene, aliphatic hydrocarbons such as n-hexane, cyclohexane, and n-heptane, and chlorobenzene, bromobenzene, iodobenzene, and o-bromotoluene. Examples include halogenated aromatic hydrocarbons, halogenated aliphatic hydrocarbons such as tetrachloromethane, 1,1,1-trichloroethane, tetrachloroethylene, and 1-chlorobutane. Copolymerization is carried out by adding a radical initiator to the above solvent in a molar ratio of 10 ^-2 to 2 x 10 ^-3 based on the total number of moles of monomers. Also, the polymerization temperature is -30 to 200
℃, preferably 20~100℃, polymerization pressure 0~100℃
Kg/cm ² ·G, preferably 0 to 50 kg/cm ² ·G. The metal chelate compound, which is another component of the paint of the present invention, may basically be any known metal chelate compound. For example, the central metal forming the chelate may be Ti, Al, Zr, Co,
Examples include Mn. Among them, Ti, Zr,
Al is preferred, and chelate compounds having Ti or Zr as the central metal are particularly preferred. A metal chelate compound can be easily obtained by reacting an alkoxide of the above metal with a chelating agent. Examples of chelating agents include β-diketones such as acetylacetone and 2,4-heptanedione, ketoesters such as methyl acetoacetate, ethyl acetoacetate, and butyl acetoacetate, lactic acid, salicylic acid, malic acid, tartaric acid, methyl lactate, Hydroxycarboxylic acids or their esters or salts thereof, such as ethyl lactate, ethyl salicylate, phenyl salicylate, ethyl malate, methyl tartrate, ethyl tartrate, ammonium lactate, 4
-Hydroxy-4-methyl-2-pentanone, 4
- Kettle alcohols such as hydroxy-2-pentanone, 4-hydroxy-2-heptanone, 4-hydroxy-4-methyl-2-heptanone, monoethanolamine, diethanolamine, N-
Amino alcohols such as methyl-monoethanolamine, N-ethyl-monoethanolamine, N,N-dimethylethanolamine, N,N-diethylethanolamine, malonic acid diethyl ester, methylolmelamine, methylolurea, methylol acrylamide, etc. Examples include enol-type active hydrogen compounds. In the present invention, from the viewpoint that the fluoropolymer as the main component is transparent, a transparent coating can be obtained by using a colorless or light-colored metal chelate compound. Examples of such colorless or light-colored metal chelate compounds include Ti(O—iC ₃ H ₇ ) ₂
(OC ₈ H ₁₆ O) ₂ , Ti(O-nC ₄ H ₉ ) ₂ (OC ₈ H ₁₆ O) ₂ , Examples include Zr(OC ₄ H ₉ ) ₃ (C ₅ H ₇ O ₂ ). The fluorine-based paint of the present invention is obtained by dissolving a solvent-soluble fluorine-based polymer that can be cured at room temperature and a metal chelate compound in an organic solvent. The ratio of the fluorine-based polymer to the metal chelate compound is 1 to 70 parts by weight, preferably 3 to 60 parts by weight, per 100 parts by weight of the polymer. If the proportion of metal chelate is too low, no improvement in adhesion is observed, and if it is too high, the coating film becomes brittle. Examples of organic solvents include aromatic hydrocarbons such as benzene, toluene, and xylene, ketones such as acetone and methyl ethyl ketone, ethers such as diethyl ether and dipropyl ether, alcohols such as ethanol, and trichloro. These include halogenated hydrocarbons such as methane, dichloroethane, and chlorobenzene. The fluorine-based paint of the present invention is an organosilicon compound when the fluorine-based polymer as its main component is [A].
Since it has a hydrolyzable organic group derived from (c), when exposed to moisture, a cross-linking reaction occurs between the molecular chains of the polymer, causing it to harden. Therefore, as a matter of course, moisture in the atmosphere can also cause crosslinking. Due to the presence of the metal chelate compound, the fluorine-based paint of the present invention has improved adhesive strength to inorganic substrates such as metal and ceramic substrates, and can be applied directly without a primer layer. Therefore, the properties of the cured fluoropolymer film can be fully exhibited, and there is no fear that the primer layer will be attacked by, for example, organic solvents or light and the film will peel off from the primer layer. Furthermore, when the fluoropolymer [A] is used, the film dries quickly to the touch and exhibits a curing accelerating effect similar to that obtained by adding a silanol condensation catalyst. The fluorine-based paint of the present invention is applied to the surfaces of metal, wood, plastic, ceramic, paper, glass, etc. using a brush, spray, roller coater, etc. in the same way as ordinary liquid paints. The film after curing is weather resistant,
It has excellent chemical resistance, solvent resistance, water resistance, heat resistance, and low friction, as well as excellent transparency and gloss. Furthermore, pigments, dyes, and the like may be blended to form a colored paint, and if necessary, various additives commonly blended with synthetic resins may be blended. [Example] The content of the present invention will be explained below using preferred examples, but unless otherwise specified, the present invention is not limited to these examples, and any embodiments may be modified without impairing the purpose of the present invention. is also possible. [Reference Experiment] Fluorine-based polymers used in Examples were polymerized in the following manner. 80 g of benzene, 14.7 g of ethyl vinyl ether (EVE), and butyl vinyl ether (BVE) in a stainless steel autoclave with an internal volume of 300 c.c. and a stirrer.
3g, trimethoxyvinylsilane (TMVS) 8.8
g, 1 g of dilauroyl peroxide is charged, solidified with acetone and dry ice, and degassed to remove oxygen from the system. Thereafter, 47 g of hexafluoropropene (HFP) was introduced into the autoclave and the temperature was raised. When the temperature inside the autoclave reached 65°C, the pressure was 8.1 Kg/cm ² . The reaction was continued for 8 hours with stirring, and when the pressure reached 4.6 Kg/cm ² , the autoclave was cooled with water to stop the reaction. After cooling, unreacted monomers were expelled, the autoclave was opened, and the reaction solution was taken out. After concentration, the mixture was washed with a benzene-methanol mixed solvent, concentrated again, and dried. The number average molecular weight of the obtained polymer by GPC was 8×10 ³ . In addition, compositional analysis was performed using elemental analysis and NMR, and HFP/EVE/BVE/TMVS = 50/
The molar ratio was 35/5/10. Table 1 also shows the polymerization results obtained by changing the type and amount of monomer.

[Table] Example 1 For 100 parts by weight of the fluorine-based polymer of Experimental Example 1,
Dibutoxy titanium bisoctylene glycolate 70
% butanol solution (Orgatics TC200, Matsumoto Pharmaceutical Co., Ltd.) in the weight parts ratio shown in Table 2, toluene 100
Parts by weight were added and mixed with stirring to obtain a fluoropolymer solution. Next, the solution was applied to a steel plate using a 50μ applicator, and after being left at room temperature for 7 days, a grid peel test, a 24-hour immersion test in acetone, a 24-hour immersion test in toluene, a pencil hardness test (JIS K5400-1979,
6.14) was carried out. The results are shown in Table 2. Note that the checkerboard peel test was conducted in the following manner. That is, cuts were made on the surface of the coating film applied to the steel plate according to "JIS K5400-1979 Paint General Test Method 6.15 Grid Test". Next, apply cellophane adhesive tape with a width of 20 mm to the surface of the paint film in the grid area, rub it strongly with a spatula of 7 mm width to bring the tape into close contact with the surface of the paint film, and then rapidly move the cellophane tape vertically upward. I pulled it up and peeled it off. The cellophane tape was adhered and peeled off a total of four times from each direction of the four sides of the grid, and the number of grids that remained without being removed was determined, and the test results were indicated by that number.

[Table] Example 2 The same procedure as in Example 1 was carried out except that the titanium compound in Example 1 was replaced with a 75% isopropanol solution of diisopropoxytitanium acetylacetonate (Orgatics TC 100, manufactured by Matsumoto Pharmaceutical Co., Ltd.). The results are shown in Table 3.

[Table] Example 3 The solution used in Example 1 was applied to a steel plate at varying thicknesses, and a checkered peel test was conducted after curing at room temperature for 7 days. The results are shown in Table 4.

[Table] Example 4 A test was conducted in the same manner as in Example 1 except that the titanium compound in Example 1 was replaced with a 75% butanol solution of acetylacetone zirconium butoxide. The results are shown in Table 5.

[Table] Example 5 A test was conducted in the same manner as in Example 1 by replacing the titanium chelate in Example 1 with 10 parts by weight of aluminum di-n-butoxide monoethyl acetate, and no peeling was observed in the grid peel test. . Examples 6 to 10 To 100 parts by weight of each fluorine-based polymer of Experimental Examples 2 to 6, 25 parts by weight of dibutoxytitanium bisoctylene glycolate 70% butanol solution and toluene were added.
100 parts by weight was added to obtain a fluoropolymer solution.
The subsequent steps were the same as in Example 1. The results are shown in Table 6.

〔Effect of the invention〕

The fluorine-based paint of the present invention can be applied to substrates with a brush, spray, roller coater, etc. in the same way as ordinary liquid paints, hardens at room temperature, does not require a baking process, and has excellent transparency, etc. Inorganic substrates such as metal plates and ceramic products that provide films with excellent optical properties, weather resistance, chemical resistance, mechanical properties, low friction properties, and water repellency;
It exhibits strong adhesion to organic substrates such as plastic products without a primer. More specifically, a fluorine-based paint containing a fluorine-based polymer [A] as a main component does not require a curing agent, so it can be used as a one-component paint;
Further, a fluorine-based paint containing [B] as a main component can be used as a two-component paint with a curing agent. Therefore metal,
It can be used as a coating agent for wood, plastics, ceramics, paper, etc., and as a surface coating for optical fibers, optical disks, and liquid crystal display substrates.

Claims (1)

[Claims] 1. Room-temperature curable compound consisting essentially of (a) a fluoroolefin, (b) a vinyl ether, and (c) an organosilicon compound having an olefinic unsaturated bond and a hydrolyzable group. A fluorine-based paint characterized in that it is formed by dissolving a solvent-soluble fluorine-based polymer and a metal chelate compound in an organic solvent. 2 The fluorine-based polymer is (a) fluoroolefin, (b)
A copolymer consisting essentially of vinyl ether and (c) an organosilicon compound having an olefinic unsaturated bond and a hydrolyzable group, the total of (a) to (c) in the copolymer. (a): 30 to 70 mol%, (b): 20 to 60 mol%, and (c): 1 to 25 mol% based on the number of moles, measured by gel permeation chromatography. The number average molecular weight (n) is 3000~
200000. The fluorine-based paint according to claim 1. 3. The fluorine-based paint according to claim 1 or 2, wherein the metal chelate compound is a chelate compound of a metal selected from Ti, Zr, and Al.