JPH11236532A - Coating agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a coating agent which imparts excellent stainproofness, anticorrosiveness, low adhesion, high lubricity, and heat resistance to a substrate by using a polymer or prepolymer having specified fluoroalkylsiloxane groups as the principal component. SOLUTION: This coating agent mainly consists of a polymer or prepolymer having fluoroalkylsiloxane groups represented by formula I (p is an integer of 0-16; q is an integer of 2-10; n is an integer of 0-1,000; a is an integer of 0-2; u is an integer of 1-6; v is 0 or 1; R<1> and R<2> are each independently fluorine or trifluoromethyl). This polymer or prepolymer may be one produced by any desired process. For example, it is prepared by reacting a fluoroalkylsiloxane- group-containing alcohol of formula II with an isocyanato-containing compound. In formula II, p, q, n, a, u, v, R<1> , and R<2> are as defined in formula I; R<3> is H or the like; R<4> is OH or the like; and R<5> is an ethylene group or the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention is used for forming a functional film surface on the surface of various articles and materials for the purpose of imparting stain resistance, corrosion resistance, high lubricity, heat resistance and the like. It relates to a coating agent.

[0002]

2. Description of the Related Art Architectural paints, tunnel paints, automotive paints, agricultural greenhouse pollution-preventing coating agents and the like have hitherto been used for the purpose of preventing surface contamination of various articles.

[0003] For the purpose of corrosion protection, bridges, overpasses, ship bottom paints and the like are used.

Further, for the purpose of imparting low adhesion, ship bottom paints, ice and snow adhesion prevention paints, paints capable of easily removing adhered dirt, super water repellent paints, coating agents for the production of release paper for adhesives, etc. Used.

Further, for the purpose of imparting low lubricity, a back coating agent for sublimation printing or the like is used.

Further, for the purpose of imparting heat resistance, a back coat agent for sublimation printing and the like are used.

[0007] Various improvements have been made to these coating agents and paints in order to enhance their intended performance. However, many of these coating agents and paints conventionally contain silicone.

[0008] However, a coating agent containing silicone,
Paints and the like are still often inadequate in terms of their durability and intended functions, and therefore have higher performance paints,
There is a need for a coating agent.

[0009]

As a result of various studies to solve the above problems, the present inventors have found that the above problems can be solved by using a polymer having a fluoroalkylsiloxane group as a coating agent. The purpose of the present invention is to provide a coating agent capable of imparting excellent stain resistance, corrosion resistance, low adhesion, high lubricity, and heat resistance. It is in.

[0010]

Means for Solving the Problems To achieve the above object, the present invention provides [1] the following formula (1):

[0011]

Embedded image (Where p is an integer of 0 to 16, q is an integer of 2 to 10, n is an integer of 0 to 1000, a is an integer of 0 to 2, u is an integer of 1 to 6, and v is 0 or 1 , R ¹ and R ² are independently a fluorine atom or a trifluoromethyl group), and a coating agent mainly comprising a polymer having a fluoroalkylsiloxane group or a prepolymer thereof, [2] a polymer, or The prepolymer is represented by the following formula (2)

[0012]

Embedded image (Where p is an integer of 0 to 16, q is an integer of 2 to 10, n is an integer of 0 to 1000, a is an integer of 0 to 2, u is an integer of 1 to 6, and v is 0 or 1 , R ¹ and R ² are each independently a fluorine atom or a trifluoromethyl group, r is an integer of 1 to 7, s is an integer of 0 to 100, t is 0 or 1, R ³ is hydrogen or a carbon number of 1 to 4. Wherein R ⁴ is a hydroxyl group or a hydroxymethyl group, and R ⁵ is an ethylene group or a propylene group.) And an isocyanate group-containing compound. The [3] polymer or its prepolymer is represented by the following formula (2):

[0013]

Embedded image (Where p is an integer of 0 to 16, q is an integer of 2 to 10, n is an integer of 0 to 1000, a is an integer of 0 to 2, u is an integer of 1 to 6, and v is 0 or 1 , R ¹ and R ² are each independently a fluorine atom or a trifluoromethyl group, r is an integer of 1 to 7, s is an integer of 0 to 100, t is 0 or 1, R ³ is hydrogen or a carbon number of 1 to 4. R ⁴ is a hydroxyl group or a hydroxymethyl group, and R ⁵ is an ethylene group or a propylene group), an isocyanate group-containing compound, and an active hydrogen-containing resin. And (4) the polymer or its prepolymer is represented by the following formula (3)

[0014]

Embedded image (Where p is an integer of 0 to 16, q is an integer of 2 to 10, n is an integer of 0 to 1000, a is an integer of 0 to 2, u is an integer of 1 to 6, and v is 0 or 1 , R ¹ and R ² are each independently a fluorine atom or a trifluoromethyl group.) And a polymerizable unsaturated compound. Including.

The coating agent of the present invention has a fluoroalkylsiloxane group consisting of a fluoroalkyl moiety and a silicone moiety in the polymer or its prepolymer molecule, so that any of the conventional silicone polymer, silicone group or fluoroalkyl group can be used. Unlike the case where a polymer having only one of them is used as a coating agent,
Excellent stain resistance, water repellency, oil repellency, anticorrosion, low adhesion,
It can exhibit high lubricity and heat resistance.

Hereinafter, the present invention will be described in detail.

[0017]

BEST MODE FOR CARRYING OUT THE INVENTION The polymer or prepolymer used as a coating agent in the present invention has a fluoroalkylsiloxane group represented by the above formula (1).

In the above formula (1), p is an integer of 0 to 16, particularly preferably an integer of 3 to 11. q is an integer of 2 to 10, and particularly preferably an integer of 2 to 4. n is 0 to 100
An integer of 0, particularly an integer of 0 to 500 is preferable. a is 0
An integer of from 2 to 2, particularly preferably 1. R ¹ and R ² are each independently a fluorine atom or a trifluoromethyl group.

Although a material other than the above range can be used, as the degree of departure from the above range increases,
There is a tendency that stain resistance, corrosion resistance, low adhesion, and the like are reduced.

The content of the fluoroalkylsiloxane group in the polymer or its prepolymer is 0.1 to 20.
% By weight, and particularly preferably 0.5 to 5% by weight.

In the present invention, the polymer or prepolymer having a fluoroalkylsiloxane group represented by the above formula (1) used as a coating agent may be produced by any method.

For example, a compound capable of reacting with these starting materials is reacted with an alcohol compound having a fluoroalkylsiloxane group represented by the following formula (2) or a methacryl compound having a fluoroalkylsiloxane group represented by the following formula (3). Can be manufactured.

[0023]

Embedded image However, in the formula, p is an integer of 0 to 16, q is an integer of 2 to 10,
n is an integer of 0 to 1000; a is an integer of 0 to 2;
An integer of 6, v is 0 or 1, R ¹ and R ² are independently a fluorine atom or a trifluoromethyl group, r is an integer of 1 to 7, s
Is an integer of 0 to 100, t is 0 or 1, R ³ is hydrogen or an alkyl group having 1 to 4 carbon atoms, R ⁴ is a hydroxyl group or hydroxymethyl group, and R ⁵ is an ethylene group or a propylene group.

[0024]

Embedded image However, in the formula, p is an integer of 0 to 16, q is an integer of 2 to 10,
n is an integer of 0 to 1000; a is an integer of 0 to 2;
Integer of 6, v is 0 or 1, R ¹ and R ² are independently a fluorine atom or a trifluoromethyl group.

(Reaction format) The following formulas (2) and (3)
A typical reaction scheme for producing a polymer or prepolymer having a fluoroalkylsiloxane group represented by the formula (1) using the compound of formula (1) will be described.

First, a reaction scheme for producing a polymer or a prepolymer using an alcohol represented by the formula (2) will be described.

Reaction type 1 (when OH group is 1) As shown in the following reaction formula (A), an alcohol (5) containing a fluoroalkylsiloxane group Rf is reacted with an isocyanate compound (6) to give an isocyanate. Compound (7) is obtained. Then, it is reacted with an active hydrogen-containing resin (8) such as an acrylic polyol having active hydrogen to obtain a polyol (9) containing a fluoroalkylsiloxane group Rf. Further, a polyol (9) and 2
By reacting with the isocyanate compound (10) having the above isocyanate group, the coating agent (11) of the present invention can be obtained.

In the following formula (A), R, R ⁵ and R ⁶ each represent an arbitrary linking group.

[0029]

Embedded image This reaction is carried out by an alcohol having a fluoroalkylsiloxane group (Rf), an isocyanate group-containing compound,
It is an example of a reaction for producing a coating agent of the present invention by reacting with an active hydrogen-containing resin.

In the above formula (A), the isocyanate compounds (6) and (10) used include tolylene diisocyanate, tolylene diisocyanate dimer, diphenylmethane diisocyanate, diphenyl ether diisocyanate, vitriylene diisocyanate, naphthalene diisocyanate and hexane. Methylene diisocyanate, lysine diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, xylylene diisocyanate, tetramethyl xylylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, dimer acid diisocyanate, isopropylidene bis (4 -Cyclohexyl diisocyanate Over g), cyclohexyl diisocyanate, and hydrogenated diphenylmethane diisocyanate and the like.

Further, three or more isocyanate groups such as triphenylmethane triisocyanate, triisocyanate phenyl thiophosphate, or an adduct of the above diisocyanates with polyhydric alcohols such as trimethylolpropane, trimethylolethane, and trimethylolmethane are used. Can also be exemplified.

Further, a prepolymer of the above-mentioned isocyanate compound and a polyhydric alcohol or a compound having two or more amino groups and a compound having an isocyanate group can also be exemplified. That is, any compound having an isocyanate group can be used.

Further, the isocyanate group of the above isocyanate compound is blocked with a compound having active hydrogen such as phenols, oximes, lactams and sodium bisulfate.
So-called blocked isocyanates can also be used.

Examples of the active hydrogen-containing resin (8) include vinyl chloride / vinyl acetate / polyvinyl alcohol copolymer, polyvinyl alcohol, polyacetal, acrylic polyol, polyester polyol and the like.

Reaction type 2 (when the number of OH groups is 2) As shown in the following reaction formula (B), isocyanate compound (6) is reacted with dialcohol (12),
An isocyanate (13) having a fluoroalkylsiloxane group is obtained. On the other hand, isocyanate compound (6)
And the active hydrogen-containing compound (14) to give a diisocyanate (15).

Thereafter, the isocyanate (13) having a fluoroalkylsiloxane group, the diisocyanate (15), and the active hydrogen-containing compound (16) are reacted, and the urethane compound (1) as the coating agent of the present invention is reacted.
7) is obtained. In the reaction formula (B), R ⁷ ,
R ⁸ and R ⁹ are any linking groups.

The active hydrogen-containing compounds (14) and (16) include ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, 2
-Dimethyl-1,3-propanediol, 1,6-hexanediol, 3-methyl-1,5 pentanediol,
1,8-octanediol, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, cyclohexane-1,4-diol, cyclohexane-1,4-dimethanol, and the above diols, etc., and dialkyl carbonate, phosgene, and chloroformic acid There are poly (alkylene carbonate) diols obtained by condensation with esters and the like.

Further, the active hydrogen-containing compounds (14), (1)
Examples of 6) include those obtained by ring-opening polymerization or copolymerization of ethylene oxide, propylene oxide, butylene oxide, and a heterocyclic ether (such as tetrahydrofuran), for example, polyethylene-ether glycol, polypropylene ether glycol, polyethylene-propylene ether glycol, Polytetramethylene ether glycol, polyhexamethylene ether glycol,
There are polyolactone polyols obtained by ring opening of polyoctamethylene ether glycol, ε-caprolactone and the like, and mixtures of two or more thereof.

Further, an active hydrogen-containing compound (14),
Examples of (16) include polyhydric alcohols having three or more alcohols, such as glycerin, trimethylolpropane, trimethylolethane, trimethylolmethane, pentaerythritol, and sorbitol.

This reaction is an example of a reaction for producing a coating agent of the present invention by reacting an alcohol having a fluoroalkylsiloxane group (Rf) with an isocyanate group-containing compound.

[0041]

Embedded image That is, when producing a linear urethane compound, (a) all isocyanate compounds and all hydroxyl group-containing compounds are charged simultaneously to obtain a product by a one-step reaction, and (b) a hydroxyl group-containing compound. Alternatively, there is a method in which one or both of the isocyanate group-containing compounds is used as a prepolymer, and the reaction is sequentially performed in two or more steps. The above formula (B) shows a sequential reaction when the compound represented by the general formula (2) is used as a part of a compound having an active hydrogen group.

Reaction format 3 An active hydrogen-containing compound is used as a compound capable of reacting with the compound represented by the general formula (2). In the above reaction format, a carboxylic acid compound or an amine compound is used instead of the hydroxy compound. To use.

Examples of the dicarboxylic acid include succinic acid, maleic acid, adipic acid, glutaric acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, fumaric acid, isophthalic acid, terephthalic acid, hexahydroisophthalic acid and the like. Is mentioned.

Further, polyester diols obtained by condensing the above diols and the above dicarboxylic acids, for example, polyethylene adipate, polybutylene adipate,
Examples include polyhexamethylene adipate, polyethylene butylene adipate, polyethylene propylene adipate and mixtures of two or more thereof.

As the organic diamine, ethylenediamine, 1,3-propylenediamine, 1,2-propylenediamine, hexamethylenediamine, hydrazine, piperazine, N, N-diaminopiperazine, 2-methylpiperazine, 4,4-diamino Dicyclohexylmethane,
Isophoronediamine and the like.

Other active hydrogen-containing compounds include γ
Ring-opened products and ring-opened polymers of lactone compounds such as butyrolactone and t-caprolactone.

Reaction Mode 4 In this reaction mode, a general commercially available resin having active hydrogen is reacted with an alcohol compound of the formula (2) or a modified product thereof to produce a polymer having a fluoroalkylsiloxane group.

As the active hydrogen-containing resin, vinyl chloride /
Vinyl acetate / vinyl alcohol copolymer resin, alkyd resin, epoxy resin, polyurethane resin, polyurea resin, nitrocellulose resin, polybutyral resin, polyester resin, silicone resin,
Known resins such as a melamine resin, a urea resin, an acrylic resin, a polyamide resin, and a polyimide resin can be exemplified. Among these resins, a polyurethane resin, a polyamide resin, and an acrylic resin are particularly preferable.

Next, the reaction type of the methacrylic compound having a fluoroalkylsiloxane group represented by the formula (3) will be described.

The fluoroalkylsiloxane group-containing methacrylic compound represented by the formula (3) has a polymerizable methacrylic group at the terminal of its chemical structure. Therefore, as shown in the following formula (C), copolymerization with compounds (18) and (19) generally having a polymerizable unsaturated bond enables
Polymer having fluoroalkylsiloxane group (2
0) can be produced. This reaction form is represented by the formula (C)
Shown in

[0051]

Embedded image Note that R ¹⁰ and R ¹¹ are any linking groups.

In the above formula (C), the compound having a polymerizable unsaturated bond is not limited to one type, and a compound having a plurality of types of polymerizable unsaturated bonds may be used.

Compounds having a polymerizable unsaturated bond include acrylic acid, alkyl esters of acrylic acid, methacrylic acid, alkyl esters of methacrylic acid, hydroxymethyl esters of acrylic acid or methacrylic acid, styrene, α-methylstyrene, -Chlorostyrene, ethylene, propylene, butadiene, isobutyl vinyl ether, methyl vinyl sulfide, N-vinyl carbazole, methyl vinyl ketone, acrylamide, maleic anhydride, vinyl acetate, isobutene, vinyl chloride, vinylidene chloride, acrylonitrile, γ-methacryloxypropyl Compounds having a radical polymerizable unsaturated bond such as trimethoxysilane can be exemplified.

As the polymerization catalyst to be used, a known catalyst can be appropriately selected and used.

As the polymerization method, general polymerization methods such as emulsion polymerization and solution polymerization can be employed.

The polymer or its prepolymer prepared as described above is used as it is or in the form of a solution using a suitable solvent, and if necessary, various additives such as known curing agents, dyes, pigments and stabilizers. Is used as the coating agent of the present invention.

The coating agent of the present invention can be used for the purpose of imparting stain resistance, corrosion resistance, low lubricity, heat resistance, etc., as described above. Materials, artificial leather, leather processing materials, various belts such as belt conveyors, coatings for resin films for photosensitive paper for electrophotography, adhesives, adhesives, water-repellent paints, oil-repellent paints, highly weather-resistant paints, snow Anti-icing paint, fiber treatment agent,
It can be used in applications such as release paper paints, back coat agents for tapes and sheets, molding agents, sealing materials for construction, binders for magnetic recording media, and antithrombotic materials.

According to the present invention, the following compounds can be provided. (A) fluoroalkylsiloxane-modified polyacrylurethane (b) fluoroalkylsiloxane-modified urethane prepolymer (c) fluoroalkylsiloxane-modified vinyl chloride / vinyl acetate / polyvinyl alcohol copolymer (d) fluoroalkylsiloxane-modified polyvinyl alcohol (e) Fluoroalkylsiloxane-modified polyacetal (f) Fluoroalkylsiloxane-modified acrylic polyol (g) Fluoroalkylsiloxane-modified polyester polyol (h) Fluoroalkylsiloxane-modified acrylic resin (i) Fluoroalkylsiloxane-modified polyester urethane (j) Fluoroalkylsiloxane-modified polyamide The present invention will be described more specifically with reference to examples.

[0059]

EXAMPLE 1 20 g of a fluoroalkylsiloxane group-containing alcohol compound represented by the following formula (21) (average molecular weight: about 1500)
And 4,4'-diphenylmethane diisocyanate
A reaction flask was charged with 3 g (OH group and NCO group at a ratio of 1: 1 mol) and 0.1 g of a 1% toluene solution of dibutyltin dilaurate as a catalyst. The mixture was stirred at 80 ° C. for 2 hours to convert the fluoroalkylsiloxane group-containing alcohol compound into isocyanate.

[0060]

Embedded image Next, 0.4 g of the isocyanated fluoroalkylsiloxane group-containing alcohol compound and Acrydic A-801 (acrylonitrile, 43 wt% solid content, Dainippon Ink and Chemicals, OH concentration 0.0
(1 mol / g) 22.3 g and toluene 10 g were charged into a reaction flask. The temperature was raised to 80 ° C., and a 1% by weight solution of dibutyltin dilaurate in toluene as a catalyst was 0.1%.
g was added and stirred for 3 hours to react, thereby obtaining 32 g of a fluoroalkylsiloxane-modified acrylic polyol resin solution. The crosslinking agent is a triisocyanate compound (hexamethylene diisocyanate adduct compound of trimethylolpropane: Takenate D160N,
Takeda Pharmaceutical Co., Ltd., solid content weight 75%, NCO concentration 0.003 mol / g)
6. The NCO concentration is equimolar to the OH concentration of 01.
5 g were added. The mixture was stirred for 10 minutes to prepare a urethane resin solution. This resin solution was applied to a stainless steel plate so as to have a thickness of 20 μm when cured, and was cured at 80 ° C. for 2 hours to obtain a test piece.

The contact angle of the test piece with water and n-hexadecane and the antifouling property with respect to magic ink were measured. The results were as shown in Table 1.

Example 2 Fluoroalkylsiloxane group-containing alcohol compound represented by the following formula (22) (average molecular weight: about 1550)
5 g (0.02 mol as OH group) and Takenate D
A reaction flask was charged with 10 g of 160N (0.03 mol as an NCO group), 40 g of toluene, and 0.2 g of a 1% by weight solution of dibutyltin dilaurate in toluene as a catalyst. The mixture was stirred at 80 ° C. for 4 hours to obtain an NCO group-containing polyurethane prepolymer solution modified with a fluoroalkylsiloxane group.

[0063]

Embedded image 8.5 g of the above prepolymer solution and 100 g of an acrylic polyol resin (Acridic A-801) were mixed,
Further, 33 g of D-160N as a cross-linking agent was further mixed (the OH concentration and the NCO concentration were made to be equimolar as a whole) to prepare a urethane resin solution.

This resin solution was applied to a stainless steel plate so as to have a thickness of 18 μm when cured, and was cured at 80 ° C. for 2 hours to obtain a test piece. Water and n of this test piece
-The contact angle to hexadecane and the antifouling property to magic ink were measured. The results were as shown in Table 1.

Example 3 A fluoroalkylsiloxane group-containing methacrylic compound represented by the following formula (23) (average molecular weight: about 1500)
g, methyl methacrylate 90 g, 2-hydroxyethyl methacrylate 40 g, butyl methacrylate 50
g, butyl acrylate 10 g, γ-methacryloxypropyltrimethoxysilane 10 g, and 2 g of 200 g of isopropyl alcohol and 20 g of ethyl acetate as a solvent.
The flask was charged.

While stirring, AIBN was used as a polymerization initiator.
Was added and polymerized at 70 ° C. for 5 hours. After polymerization,
The polymerization solution was cooled, and isopropyl alcohol 400
g and 170 g of ethyl acetate were added and diluted to obtain an acrylic resin solution in which the fluoroalkylsiloxane was copolymerized.

[0067]

Embedded image The above acrylic resin solution was applied to a stainless steel plate so as to have a thickness of 18 μm when cured, and cured at 120 ° C. for 20 minutes to prepare a test piece. The contact angle of the test piece to water and n-hexanedecane was measured. The results were as shown in Table 1.

Comparative Example 1 (Comparative Example of Example 1) A test piece was prepared in the same manner as in Example 1 except that a siloxane group-containing alcohol compound represented by the following formula (average molecular weight: 1100) was used.

[0069]

Embedded image The contact angle of the test piece to water and n-hexadecane and the antifouling property to magic ink were measured.
The results were as shown in Table 1.

Comparative Example 2 A test piece was prepared in the same manner as in Example 2 except that a siloxane group-containing alcohol compound represented by the following formula (25) (average molecular weight: 1300) was used.

[0071]

Embedded image The contact angle of the test piece to water and n-hexadecane and the antifouling property to magic ink were measured.
The results were as shown in Table 1.

Comparative Example 3 Example 3 was repeated except that a siloxane-containing methacrylic compound (average molecular weight 1100) represented by the following formula (26) was used.
A test piece was prepared in the same manner as described above.

[0073]

Embedded image The contact angle of the test piece to water and n-hexadecane and the stain resistance to magic ink were measured. The results were as shown in Table 1.

[0074]

[Table 1] Stain resistance indicates the situation when a straight line was drawn on a test piece with red magic ink and wiped off with a dry cloth.

A: Even if drawing and wiping are repeated 10 times or more, it can be wiped off by rubbing lightly.

○: Even if drawing and wiping are repeated, it can be wiped off lightly, but a faint trace remains.

△: If it is not rubbed strongly, it cannot be wiped off, and if it is repeated, it cannot be wiped off at all.

X: No wiping was possible.

[0079]

Since the coating agent of the present invention has a fluoroalkylsiloxane group in the molecule, it exhibits excellent stain resistance, low adhesion, anticorrosion, low lubrication, heat resistance and the like. Further, since the fluoroalkylsiloxane group is chemically bonded to the polymer molecule, the fluoroalkylsiloxane group has characteristics such as less deterioration and no bleeding even when the coating agent is used for a long period of time.

Claims (4)

[Claims] [Claim 1] The following formula (1) (Where p is an integer of 0 to 16, q is an integer of 2 to 10, n is an integer of 0 to 1000, a is an integer of 0 to 2, u is an integer of 1 to 6, and v is 0 or 1 , R ¹ and R ² are each independently a fluorine atom or a trifluoromethyl group), or a coating agent having a fluoroalkylsiloxane group or a prepolymer thereof as a main component. 2. The polymer or a prepolymer thereof is represented by the following formula (2): (Where p is an integer of 0 to 16, q is an integer of 2 to 10, n is an integer of 0 to 1000, a is an integer of 0 to 2, u is an integer of 1 to 6, and v is 0 or 1 , R ¹ and R ² are each independently a fluorine atom or a trifluoromethyl group, r is an integer of 1 to 7, s is an integer of 0 to 100, t is 0 or 1, R ³ is hydrogen or a carbon number of 1 to 4. Wherein R ⁴ is a hydroxyl group or a hydroxymethyl group, and R ⁵ is an ethylene group or a propylene group.) And an isocyanate group-containing compound. 2. The coating agent according to 1. 3. The polymer or a prepolymer thereof is represented by the following formula (2): (Where p is an integer of 0 to 16, q is an integer of 2 to 10, n is an integer of 0 to 1000, a is an integer of 0 to 2, u is an integer of 1 to 6, and v is 0 or 1 , R ¹ and R ² are each independently a fluorine atom or a trifluoromethyl group, r is an integer of 1 to 7, s is an integer of 0 to 100, t is 0 or 1, R ³ is hydrogen or a carbon number of 1 to 4. R ⁴ is a hydroxyl group or a hydroxymethyl group, and R ⁵ is an ethylene group or a propylene group), an isocyanate group-containing compound, and an active hydrogen-containing resin. The coating agent according to claim 1, which is produced by reacting. 4. The polymer or a prepolymer thereof is represented by the following formula (3): (Where p is an integer of 0 to 16, q is an integer of 2 to 10, n is an integer of 0 to 1000, a is an integer of 0 to 2, u is an integer of 1 to 6, and v is 0 or 1 , R ¹ and R ² are each independently a fluorine atom or a trifluoromethyl group.) The methacrylic compound having a fluoroalkylsiloxane group represented by the formula (I) is reacted with a polymerizable unsaturated compound. Coating agent.