JPH04170469A - Thermosetting resin composition - Google Patents

Abstract

PURPOSE:To obtain the title composition which can give a cured product excellent in chemical properties, physical properties and weathering resistance by mixing a compound having a plurality of specified vinyl (thio)ether groups with a compound having a plurality of acetoacetyl groups in the molecule. CONSTITUTION:A resin composition comprising a compound (A) having at least too vinyl ether groups or vinyl thioether groups of the formula in the molecule and a compound (B) having at least two acetoacetyl groups in the molecule. In the formula, R1 to R5 are each II or a 1-18C organic group; R1 and R4, R1 and R5, R2 and R4 or R2 and R5 may be combined with each other to form a heterocyclic ring having Y as a heteroatom, and Y is 0 or S. Components (A) and (B) are desirably used in such a ratio that the equivalent ratio of the vinyl ether or vinyl thioether groups of component (A) to the acetoacetyl groups of component (B) is 0.2:1 to 1.0:0.2.

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention provides a novel thermosetting resin composition, more specifically,
Provides a cured product with excellent chemical performance, physical performance and weather resistance,
For example, it relates to thermosetting resin compositions suitable for use in paints, inks, adhesives, molded products, and the like. - [Prior Art] Conventionally, thermosetting resin compositions used in the field of paints and the like have been mainly composed of a hydroxyl group-containing resin and a melamine resin or a polyisone atom compound.

However, when a melamine resin is used in the composition, since the melamine resin itself is basic, there arises a problem that the chemical performance of the cured product is insufficient, and the polyisocyanate is insufficient. When using isocyanate compounds, it is possible to obtain a cured product with excellent chemical performance, but there is a problem in that isocyanate compounds are highly toxic and difficult to use in today's world where environmental issues are being emphasized.

In order to solve these problems, other thermosetting resin compositions have recently been actively investigated. Methods of obtaining things are being tried. However, the cured product obtained by this method may be colored or have insufficient water resistance due to secondary hydroxyl groups generated by the curing reaction, especially when the crosslink density is increased to improve physical performance. It has the following disadvantages.

In addition, hydroxyl group-containing resin and two vinyl ether groups in one molecule.
A method of obtaining a cured product by reaction with a compound containing more than
No. Specification). However, even in this case, problems arise, such as the cured product being easily colored and having insufficient hydrolysis resistance.

[Problems to be Solved by the Invention] Under these circumstances, the purpose of the present invention is to provide a novel thermosetting resin composition that provides a cured product with excellent chemical performance, physical performance, and weather resistance. This was done as a.

[Means for Solving the Problems] As a result of intensive research to develop a thermosetting resin composition having the above-mentioned preferable properties, the present inventors found that two vinyl ether groups or vinyl thioether groups are present in one molecule. It was discovered that the object could be achieved by combining a compound having the above with a compound having two or more acetoacetyl groups in one molecule, and based on this knowledge, the present invention was completed.

That is, in the present invention, in one molecule of (A) - formula % formula % (R1, R2, R8, R1 and R6 are each a hydrogen atom or an organic group having 1 to 18 carbon atoms, R3 and R4 ,R
, and R6, R2 and R, or R7 and R6 may be directly bonded to form a heterocycle in which Y is a heteroatom, and Y is an oxygen atom or a sulfur atom). The present invention provides a thermosetting resin composition comprising a compound having two or more or vinylthioether groups, and (B) a compound having two or more acetoacetyl groups in one molecule.

The present invention will be explained in detail below.

In the composition of the present invention, as component (A), in one molecule, a vinyl ether group represented by the following formula (R1, R2, R1, R6 and Y in the formula have the same meanings as above) or A compound having two or more vinyl thousand-oneythyl groups is used.

R, , R2, R1, R4 and R1 in the above formula (1) are each a hydrogen atom or an organic group such as an alkyl group having 1 to 18 carbon atoms, an aryl group, an alkaryl group, and these organic groups may have a suitable substituent, and R1 and R1, R, and R5, R2 and R4, or R2 and R, have no substituent that is strongly bonded to make Y a heteroatom, or may form a heterocyclic ring having

Examples of such compounds as component (A) include (1), t
Ethylene glycol divinyl ether, propylene glycol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, butanediol divinyl ether, butanediol diisoprobenyl ether, pentanediol divinyl ether, hexanediol divinyl ether, Low molecular weight polyhydric ethers such as benzyl glycol diisobropenyl ether, trimethylolpropane trivinyl ether, pentaerythritol tetravinyl ether, and tishchenko ester of acrolein dimer; (2) adducts of low molecular weight polyhydric ethers and polyols; For example, the low molecular weight polyhydric ether of (1) above, ethanediol, propanediol, butanediol, bentanediol, octanediol or their homologs, corresponding oligomer ethers, glycerin, trimethylolethane, trimethylolpropane, hexanetriol. , pentaerythritol, dipentaerythritol, sorbitol, polyvinyl alcohol, bisphenol A luzorcin, hydroquinone or derivatives thereof, trishydroxyethylison anurate, hydroxyl group-containing epoxide, hydroxyl group-containing polyether, hydroxyl group-containing polyester, hydroxyl group-containing polyester adducts with polyols such as acrylic; (3) adducts between low molecular weight polyhydric ethers and polyhydric carboxylic acids; for example, adducts between low molecular weight polyhydric ethers of (1) above and sulfuric acid, malonic acid, succinic acid, glutaric acid; Acid, adipic acid, azelaic acid, sebacic acid, decamethylene dicarboxylic acid, maleic acid, fumaric acid, heptalacid, isophthalic acid, terephthalic acid, hexahydrophthalic acid, methylated hexahydrophthalic acid, trimellitic acid, pyro Polyhydric carboxylic acids such as mellitic acid, adducts with polyester resins and acrylic resins having two or more carboxyl groups in one molecule, (4) reaction products of monovinyl ether or acetal with polyols, such as methyl vinyl ether, Aliphatic vinyl ether compounds such as ethyl vinyl vinyl ether, isopropyl vinyl ether, n-propyl vinyl ether, n-butyl vinyl ether, inbutyl vinyl ether, cyclohexine rubinyl ether, and corresponding aliphatic vinyl ether compounds, and further 2
．． 3-dihydro7ran, 3.4-dihydrofuran, 2.
3-dihydro-2H-pyran, 3.4-dihydro-2H
-pyran, 3,4-dihydro-2-methoxy-2H-pyran, 3,4-dihydro-4,4-dimethyl-2H-pyran-2-one, 3,4-dihydro-2-ethoxy-2
Monovinyl ethers or monovinylthioethers such as cyclic vinyl ether compounds such as H-pyran, sodium 3,4-dihydro-2H-pyran-2-carboxylate, and corresponding cyclic vinyl thioether compounds, and monovinyl thioethers as exemplified in (2) above. The acetal compound obtained by reaction with polyols is cleaved into a new vinyl ether compound, (5) an adduct of a hydroxyl group-containing monovinyl ether and a polyhydric isocyanate compound, such as ethylene glycol monovinyl ether, propylene glycol. 7-novinyl ether, 1,4-butylene glycol 7-novinyl ether, methanol dihydropyran, etc., and tetramethylene diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, l,12-dodecane diisocyanate, Isocyanate, cyclohexane-1,3- or -1,4-
Diisocyanates, inphorone diisocyanate, perhydro-2,4'- or -4,4''-diphenylmethane diisocyanate, 1,3- and 1,4-7 2-2-2-2 di-inocyanate, 2,4- and 2,6-tolylene diisocyanate Isocyanate, diphenylmethane-2,4'- or -4,
4'-diisocyanate, 3,2- or 3,4-diisocyano-4''-methyldiphenylmethane, naphthalene-1,5-diisocyanate, triphenylmethane-
4,4″,4″-triisonanate or an adduct of these low molecular weight polyisoneanate with isocyanate type, biuret type, polyol addition type polyisocyanate, (6) a, β-union Transesterification reaction products of saturated carboxylic acid ester homopolymers or copolymers with vinyl ether group-containing alcohols or thiols, such as a, β-
An acrylic resin consisting of an unsaturated carboxylic acid ester homopolymer or copolymer, -Formula %Formula % (R6, R7 and R1 in the formula are hydrogen atoms or carbon atoms 1 to 1)
18 alkyl groups, aryl groups, alkaryl groups, R,
is a divalent organic group such as an alkylene group, arylene group, or alkaline group having 2 to 18 carbon atoms, and R6 and R,
They may be bonded to each other to form a heterocycle with or without a substituent that makes X a heteroatom, and X and z
The compound represented by the following formula is a sulfur atom or a sulfur atom, which may be the same or different, respectively, in the presence of a basic catalyst. Examples include products that can be used. These (A) component compounds may be used alone or in combination of two or more.

In the composition of the present invention, a compound having two or more acetoacetyl groups is used as component (B).

Specific examples of such compounds as component (B) include (7
) Transesterified products of acetoacetic ester and polyol, such as methyl acetoacetate, ethyl acetoacetate, (transesterified product of acetoacetic ester such as -butyl acetoacetate and the polyol of (2) above,
(8) Polyols with diketene added and acetoacetylated, such as the polyol and diketene adduct of (2) above, (9) acetoacetyl group-containing a, β-unsaturated compounds, or hydroxyl group-containing α, Homopolymers of β-unsaturated compounds acetoacetylated with acetoacetate or diketene, or copolymers with other α,β-unsaturated compounds without reactive functional groups, such as acetoacetoxyethyl methacrylate. acetoacetyl group-containing σ, β-unsaturated compound, 2-hydroxyethyl (meth)acrylate, hydroquinepropyl (meth)
acrylate, 2-hydroxy-3-chloropropyl acrylate, acryloyloxyethyl hydrogen phthalate,
β-hydroxyethyl-β-acryloyloxyethyl phthalate, 1,4-butylene glycol monoacrylate, N-methylol acrylamide, hydroxystyrene, vinyl alcohol, (meth)allyl alcohol, impropenyl alcohol, 1-butynyl alcohol, etc. A hydroxyl group-containing σ, β-unsaturated compound is acetoacetylated with the acetoacetate or diketene of (7) above, and a homopolymer thereof, or a monomer thereof, methyl (meth)acrylate, ethyl (meth)acrylate, etc.
Acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate
Acrylate, isobutyl (meth)acrylate, 5e
c-butyl (meth)acrylate, nclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, stearyl (meth)acrylate, styrene,
Examples include copolymers with a1β-unsaturated compounds having no reactive functional group, such as a-methylstyrene, p-vinyltoluene, and acrylonitrile.

One type of compound having two or more acetoacetyl groups in one molecule of component (B) may be used, or two or more types may be used in combination. Furthermore, the composition of the present invention contains one vinyl ether group or vinyl thioether group and one acetoacetyl group represented by the general formula (I) in one molecule.
A self-crosslinkable curable resin composition may contain at least one of these.

Regarding the usage ratio of the component (A) and component (B) in the composition of the present invention, the equivalent ratio of the vinyl ether group or vinyl thioether group in the component (A) to the acetoacetyl group in the component (B) is 0. .2: 1.0 to 1.0:
It is desirable to use component (A) and component (B) in a ratio of 0.2. If this equivalent ratio deviates from the above range, the effects of the present invention will not be fully exhibited.

The compositions of the present invention can be cured more quickly in the presence of an acid catalyst such as a Lewis or Brønsted acid. Examples of these acid catalysts include p-1-luenesulfonic acid, dodecylbenzenesulfonic acid, dinonylnaphthalenesulfonic acid, dinonylnaphthalenesulfonic acid,
Sulfonic acids such as methanesulfonic acid, ethanesulfonic acid and aliphatic sulfonic acid compounds obtained by decationizing aliphatic sulfonic acid surfactants, monomethyl phosphoric acid, monoethyl phosphoric acid, dimethyl phosphoric acid, diethyl phosphoric acid, etc. Organic phosphoric acids, and formic acid, acetic acid, propionic acid,
Examples include carboxylic acids such as oxalic acid, malonic acid, and maleic acid.

At this time, the acid catalyst is an amine, such as monoethylamine, n-propylamine, isopropylamine, n-
Primary amines such as butylamine, isobutylamine, 5ec-butylamine, t-butylamine, pentylamine, secondary amines such as diethylamine, dipropylamine, diisopropylamine, dibutylamine, diisobutylamine, dipentylamine, trimethylamine, triethylamine, Neutralized salts with tertiary amines such as propylamine, tributylamine, pyridine, and N-methylmorpholine may also be used.

Furthermore, in the case of sulfonic acids, the acid catalyst may be a β-hydroxy ester with an epochine compound, such as phenylgrindyl ether, versatic acid grindyl ester, styrene oxide, or bisphenol A type epoxy compound. It can also be an ester with an aliphatic or alicyclic primary, secondary or tertiary alcohol.

Furthermore, as the acid catalyst, the general formula % ([) (R1゜ in the formula is an alkyl group, an alkenyl group, an aryl group, an alkaryl group, an alkanol group, or a cycloalkyl group having 1 to 12 carbon atoms; , two R's may be bonded to each other to form a heterocyclic ring having N1P, O or S as a heteroatom, R11 is a hydrogen atom, and has 1 to 1 carbon atoms.
12 alkyl groups, alkenyl groups, aryl groups, alkaryl groups, X- is SbF, -1AsF, -1PF, -1
Ammonium, phosphonium, oxonium and sulfonium compounds can also be used.

There is no particular restriction on the amount of the acid catalyst added, but in order to cure efficiently in a short time, it is common to use component (A) and component (B).
It is desirable that the amount is in the range of 0.01-10% by weight based on the total amount of the components.

The temperature and time required for curing the thermosetting resin composition of the present invention vary depending on the types of components (A) and (B) and the acid catalyst used, but at a temperature in the range of room temperature to 200°C for 2 minutes. It is generally about 10 to 10 hours.

The thermosetting resin composition of the present invention may contain pigments, dyes, colorants such as glass flakes, aluminum flakes, mica flakes, fillers, solvents, pigment dispersants, flow regulators, etc. as is or as necessary. , a leveling agent, a curing catalyst, a gelling inhibitor, an antioxidant, an ultraviolet absorber, a radical scavenger, etc. can be blended and used in paints, inks, adhesives, molded products, etc.

[Examples] Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples in any way.

In addition, the coating film performance was evaluated as follows.

(1) Hardness of lead duct according to JIS K-5400 (1979) 6.14.

(2) Place 2 mQ of acid-resistant 40 wt% sulfuric acid on the test piece in a spot shape,
After being left at 20°C for 48 hours, abnormalities in the coating film were visually determined.

(3) Boiling water resistance After immersing the test piece in boiling water for 3 hours, abnormalities in the coating film were visually determined.

(4) Impact resistance DuPont impact deformation tester [JISK-5400 (19
79) 6.13.3B method], radius 6.35 mm
Place the test piece between the shooting molds and add a 500g weight to 40c.
Damage to the paint film was visually determined when dropped from a height of m.

(5) If yellowing Visually determine the degree of yellowing of the cured coating.

(6) Weatherproof sun/cane weather meter (JISB-7753)
After 1000 hours of exposure using
-5400 (1979) 6.71m].

Production Example 1 Production of Compound A-1 Solution In a flask with a stopper, 12.3 parts by weight of trimethylolpropane and 3.4-dihydro-2H-yl-methyl-3,4
-dihydro-2H-pyran-2-carboxylate C (hereinafter abbreviated as DHPDNPC) and 66.7 parts by weight of acetic acid n-
It was suspended in 34 parts by weight of butyl. To this was added 0.1 part by weight of dodecylbenzenesulfonic acid, and the mixture was stirred at room temperature for 24 hours.

After filtration, a compound A-1 solution having a nonvolatile content of 70 wt% and an equivalent weight of vinyl ether groups of 380 was obtained.

Production Example 2 Production of Compound A-2 Solution In a flask with a stopper, 18.5 parts by weight of trishydroxyethylisonanurate and 58.51°C parts of DHPDRPC were suspended in 33 parts by weight of n-butyl acetate. By adding 0.1 part by weight of dodecylbenzenesulfonic acid and stirring at room temperature until the precipitate was dissolved, the nonvolatile content was 71 wt% and the equivalent weight of vinyl ether group was 420%.
A compound A-2 solution was obtained.

Preparation Example 3 Preparation of Compound A-3 Solution Polyisocyanate containing cyanurate groups obtained starting from hexamethylene diisophyl in a four-bottle flask equipped with a reflux condenser, a stirrer, a dropping funnel, and a thermometer. [Product name: Bayer Dismodule N330
0] 191 parts by weight of trimethylhexamethylene diisocyanate and 19 parts by weight of trimethylhexamethylene diisocyanate were dissolved in 149 parts by weight of propylene glycol monoethyl acetate at 50°C, and 0.1 part by weight of dibutyltin dilaurate and 19 parts by weight of 1.4-butylene glycol monovinyl ether were dissolved. and 0.3 S1i parts of hydroquinone monomethyl ether was added from the dropping funnel at 50°C over 40 minutes.

Next, the non-volatile content was reduced to 70w by stirring at 50°C until the isocyanate content became 0.1wt% or less.
A solution of Compound A-3 having a vinyl ether group equivalent weight of 420 was obtained.

Production Example 4 Production of Compound A-4 Solution Polyisocyanate containing cyanurate groups obtained starting from inphoron diisocyanate in a four-bottle flask equipped with a reflux condenser, a stirrer, a dropping funnel, and a thermometer. [Product name, T-18905 manufactured by Huls] 245 parts by weight was dissolved in 241 parts by weight of n-butyl acetate at 50°C,
A mixture of 0.1 part by weight of dibutyltin dilaurate, 31 parts by weight of 116 parts of 1,4-butylene glycol heptanovinyl ether, and 0.5 parts by weight of hydroquinone monomethyl ether was added from the dropping funnel at 50°C over 60 minutes. Next, by stirring until the isocyanate content becomes 0.1 wt% or less, the nonvolatile content is reduced to 60 W (
%, compound A- with an equivalent weight of vinyl ether group of 600
4 solutions were obtained.

Production Example 5 Production of Compound A-5 Solution In a four-bottle flask equipped with a reflux condenser, a stirrer, a dropping funnel, and a thermometer, 134 parts by weight of trimethylolpropane, 462 parts by weight of hexahydrophthalic anhydride, and n-acetic acid were added. By stirring 543 parts by weight of butyl at reflux temperature for 4 hours, a half ester compound having a solution acid value of 148 was obtained.

Next, the mixture in the flask was cooled to room temperature, 1 part by weight of dodecylbenzenesulfonic acid was added, and DHPDHPC
672 parts by weight was added from the dropping funnel over 30 minutes. Thereafter, by stirring at room temperature until the acid value of the solution became 1 or less, a compound A-5 solution having a nonvolatile content of 70 wt% and an equivalent weight of vinyl ether group of 604 was obtained.

Production Example 6 Production of Compound A-6 Solution 130 parts by weight of 2-hydroxyethyl methacrylate, 224 parts by weight of DHPDHPC, and 0.3 parts by weight of dodenlebenzenesulfonic acid were stirred at room temperature for 24 hours in a flask with a stopper. σ containing
A β-unsaturated compound was obtained.

Next, 69 parts by weight of xylene and 0.5 parts by weight of triethylamine were charged into a four-bottle flask equipped with a reflux condenser, a stirrer, a dropping funnel, and a thermometer, and heated to 80°C with stirring. From the above, 35.4 parts by weight of the a, β-unsaturated compound containing the vinyl ether group, 30.0 parts by weight of methyl methacrylate, 34.6 parts by weight of n-butyl acrylate, 260 parts by weight of n-butyl acetate, and 2,2 parts by weight. By adding a mixture consisting of 4.5 parts by weight of azobisisobutyronitrile over 2 hours and stirring at 80°C for 2 hours, a compound A- 6 solutions were obtained.

Production Examples 7 to 9 Production of Compounds B-1 to B-3 Solutions A four-loaf flask equipped with a thermometer, a reflux condenser, a stirrer, and a dropping funnel was charged with the initial charging solvent in the amounts listed in Table 1, respectively. It was heated under stirring and kept at 80°C. Then 80℃
A monomer and polymerization initiator mixture (dropped component) having the composition shown in Table 1 was allowed to flow down at a constant velocity from the dropping funnel over a period of 2 hours at a temperature of . After completing the dropwise addition, maintain the temperature at 80°C for 1 hour, add a polymerization initiator solution (additional catalyst) having the composition listed in Table 1, and further maintain the temperature at 80°C for 4 hours to complete the reaction. Compound B-1, B-2, and B-3 solutions each having the properties listed in Table 1 were obtained.

(Leaving space below) Production Example 1 O Preparation of Compound B-4 Solution In a three-loaf flask equipped with a thermometer, a stirrer, a Daenshark trap, and a reflux condenser, 134 parts by weight of trimethylolpropane and 474 parts by weight of t-butylacetoacetate were added. , 165.4 parts by weight of methyl amyl ketone were charged, and t-
By stirring at 120° C. for 4 hours while removing butanol, a compound B-4 solution having a nonvolatile content of 70 wt% and an equivalent weight of acetoacetyl group of 183.8 was obtained.

Comparative Production Example 1 Production of polyol resin solution Reflux condenser,
7-lens 4-hole flask equipped with stirrer, dropping funnel, and thermometer 61. Add 1 part of s weight and stir while stirring.
Heated to 0°C.

Next, 20.0 parts by weight of methyl methacrylate 30.7 parts by weight of n-butyl methacrylate 16.5 parts by weight of 2-ethylhexyl acrylate 29.9 parts by weight of 2-hydroquinepropyl methacrylate 4 parts by weight of L-butylperoxybenzoute A mixture consisting of 0.0 parts by weight was allowed to flow down at a constant velocity at 140° C. over a period of 2 hours. After the dropwise addition, the reaction was terminated by maintaining the temperature at 140°C for another 2 hours, and the nonvolatile content was 60 wt% and the resin hydroxyl value was 1.
20. A polyol resin solution with a viscosity (25° C.) of XY was obtained.

Application Examples 1 to 6 for one-component one-coat solid color (a) Preparation of paint Regarding the composition j in Table 2, in Example 1, compound A-1,
Compound A-2 in Example 2, Compound A-3 in Example 3
, Compound A-4 in Example 4, Compound A-4 in Example 5
5. In Example 6, the mixture excluding compound B-4 was charged into a sand mill and dispersed until the particle size became 10 μm or less, and then the raw materials removed during pigment dispersion were added and mixed to obtain a raw paint. .

(b) Preparation of test piece Cationic electrodeposition paint Aqua No4 on zinc phosphate treated mild steel plate
200 [Product name, manufactured by Nippon Oil & Fats Co., Ltd.] with a dry film thickness of 20
Electrodeposition coating to give a thickness of μm, baking at 175°C for 25 minutes, and applying intermediate coating Epico No1500CP sealer [
A test plate was prepared by air-spraying the sample with a dry film thickness of 40 μm using the product name “Nippon Oil & Fats Corporation” and baking it at 140° C. for 30 minutes.

Next, each of the fresh paints in (a) was diluted with thinner (xylene/n-butyl acetate - 8/2 weight ratio) to a coating viscosity (Ford Cup No. 4, 25 seconds at 20°C), and then prepared by the above method. Paint the test board with air spray, 1
A test piece was prepared by baking at 40°C for 30 minutes.

The coating thickness performance is shown in Table 3. In all cases, a uniform and glossy coating film with no yellowing was obtained, and it had excellent resistance to rs.
It has properties such as durability, boiling water resistance, impact resistance, and weather resistance.

Comparative Example 1.2 (a) Preparation of paint In the composition shown in Table 4, in Comparative Example 1 Cymel 303,
In Comparative Example 2, the mixture excluding Compound A-4 was charged into a sand mill and dispersed until the particle size became 10 μm or less. Thereafter, in Comparative Example 1, Cymel 303 was added and mixed to make a one-component paint, and in Comparative Example 2, a two-component paint was made as it was.

(b) Preparation of test piece The fresh paint of (a) above was used as it is in Comparative Example 1, and in Comparative Example 2, Compound A-4 was added and mixed immediately before dilution. -butyl-8
/2 weight ratio) and coating viscosity (Ford Cup No. 4.20).
℃ for 25 seconds), the test plates prepared in the same manner as Examples 1 to 6 were coated with air spray, and heated at 140℃ for 3 seconds.
Baked for 0 minutes.

The coating film performance is shown in Table 5. In Comparative Example 1, melamine resin was used as the curing agent, and the acid resistance was poor. Further, in Comparative Example 2, since it was a cured product of a resin containing a vinyl ether group and a waterfront group, yellowing was observed during baking and drying, and the boiling water resistance was also poor.

(The following is a blank space) [Effects of the invention] The thermosetting resin composition of the present invention has excellent chemical performance, physical performance,
Furthermore, it provides a cured product with excellent weather resistance and is suitable for use in a wide variety of paints, inks, adhesives, molded products, etc.

Claims (1)

[Claims] 1(A) One molecule contains a general formula ▲a mathematical formula, a chemical formula, a table, etc.▼ (In the formula, R_1, R_2, R_3, R_4 and R_5 are each a hydrogen atom or a carbon number of 18 organic groups, R_
1 and R_4, R_1 and R_5, R_2 and R4 or R
_2 and R_5 may be bonded to each other to form a heterocycle with Y as a heteroatom, and Y is an oxygen atom or a sulfur atom) having two or more vinyl ether groups or vinyl thioether groups represented by A thermosetting resin composition comprising a compound and (B) a compound having two or more acetoacetyl groups in one molecule.