JP2003105012A - Resin composition and coating material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a resin composition with its hardened matter not suffering after-yellowing, short in working life and rapid in hardening in a wide range of low to high temperatures even when polymerized and hardened into a thin film, and to provide a coating material rapid in hardening, with its working life easily controlled according to coating conditions. SOLUTION: The resin composition contains (A) a (meth)acrylic ester, (B) an acrylic polymer soluble in the component (A), (C) one or more compounds selected from the group consisting of a heterocyclic amine, an aliphatic amine, and an alicyclic amine, (D) a metal compound, and (E) a peroxide.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel resin composition, which can be preferably used particularly as a coating material because it cures quickly after a short pot life.

[0002]

2. Description of the Related Art Epoxy resins, acrylic resins and the like are known as resins used as a coating material for coating a road surface such as concrete or asphalt or a floor or wall to be coated. However, the epoxy-based resin has drawbacks such as difficulty in thick coating by one coating, poor durability, slow curing speed and long coating time. On the other hand, the acrylic resin can be applied thickly by one-time application, and has a short curing time and excellent durability.
As a polymerization initiator for polymerizing an acrylic resin, for example, JP-B1-36508 discloses a wall coating or marking composition using a redox polymerization initiator composed of an organic peroxide and a tertiary amine. Has been done. However, when a redox polymerization initiator composed of an organic peroxide and a tertiary amine is used in such an acrylic resin, there is a problem that the weather resistance is poor and the cured product turns yellow over time.

As a method for solving such problems, for example, Japanese Patent Publication No. 50-22586 discloses a polymerization initiator comprising a peroxide, a sulfur compound, a metal compound and water as a polymerization initiator for an acrylic resin. JP-B-6-10221 discloses that in a method for producing a methyl methacrylate polymer, a radical polymerization initiator, a reducing substance containing sulfur in the molecule, a hydrogen halide salt of an amine or a halogen. The use of a compound containing quaternary ammonium chloride and copper is disclosed in JP-B-8-5928 as a method for producing a vinyl polymer from peroxyester, mercaptans, organic amines, tin, aluminum, or antimony. The use of metal complexes of selected metals with organic compounds such as acetylacetone is disclosed. In addition, Japanese Patent Publication No. 4-81661 discloses
A composition which comprises a curing agent composed of a semi-ester of a bifunctional acid and a salt of sulfinic acid and is capable of curing in a short time at room temperature and strongly adhering to a human body hard tissue or metal is provided. It is disclosed. However, although the polymerization initiators used in these methods are effective in suppressing yellowing of the cured product over time, they are at room temperature to low temperature, specifically about -30.
At present, the fast curability in a wide temperature range of up to + 50 ° C is not sufficient.

Further, an organic peroxide is used as a polymerization catalyst, and as a curing accelerator, thiourea and thiourea derivatives, aliphatic and aromatic mercaptan compounds, aliphatic and aromatic amines and amine derivatives, ascorbic acid and the like. Derivative,
The use of inorganic and organic iron, cobalt or copper compounds is known, but when these curing accelerators are blended in (meth) acrylic syrup or monomer and stored for a long time, monomer components and blending components or blending components When interacting with each other, the quality of the product deteriorates, the curability decreases, or gelation occurs.
Storage stability tends to decrease.

As a method for solving such a problem,
For example, JP-A-6-33020 discloses an adhesive composition containing an organic peroxide, dithiosalicylic acid as a curing accelerator, N, N-dimethylbenzylamine, and a copper compound as a polymerization initiator. In this way, (meta)
It is shown that the acrylic monomer is mixed with dithiosalicylic acid, which is a curing accelerator, N, N-dimethylbenzylamine and a copper compound, and good storage stability at + 50 ° C. for 30 days is shown. However, this cured product has a problem that coloring is observed at the initial stage or over time. As described above, it was difficult to put the coating material using the acrylic resin into practical use for outdoor use.

On the other hand, Polymer Communications (Po
lymer Communications Vol. 30 pp136-138, (1989)), an aqueous polymerization of acrylonitrile with a redox initiator of peroxomonosulfate and thiomalic acid, Macromolecular Chemie (makromol. Chem. Vo.
l.179, pp295-300 (1978)), aqueous polymerization of acrylamide with a redox initiator of potassium peroxodisulfate and thioglycolic acid, Journal of Macromolecular Science (J. Macromol. Chem., a. -12 (9),
pp1275-1281 (1978)), aqueous polymerization of methacrylamide with a redox initiator of ammonium peroxodisulfate and thiolactic acid (2-mercaptopropionic acid), Journal of Polymer Science, Polymer Chemistry Edition (J. Polym.chem Vol.21, pp
2665-2674 (1983)) discloses aqueous polymerization of methyl methacrylate with a redox initiator of potassium peroxodisulfate and thiomalic acid. However,
The coating materials described in these known documents are redox aqueous radical polymerization of a water-soluble peroxide and a thio compound. Therefore, it is difficult to use such a polymerization initiator in the civil engineering and construction application as described above, which is performed by bulk polymerization using only a monomer without using a solvent.

[0007]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a resin composition having a property that a cured product having excellent weather resistance can be obtained and that it can be rapidly cured after a short pot life. .

[0008]

That is, the present invention is
(Meth) acrylic acid ester (A), at least one compound selected from an acrylic polymer (B) soluble in the component (A), an amine having a heterocyclic structure, an aliphatic amine, and an alicyclic amine, And a resin composition containing the metal compound (D), and a (meth) acrylic ester (A), an acrylic polymer (B) soluble in the component (A), a heterocyclic compound containing a nitrogen atom, and an aliphatic compound. A coating material containing at least one compound (C) selected from amines or alicyclic amines, a metal compound (D), and a peroxide (E).

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, the "pot life" means the time from the start of mixing and stirring the resin composition of the present invention with a stirring bar until the stirring becomes impossible due to an increase in viscosity. "Curing time" means the time until the surface of the cured product of the resin composition of the present invention becomes completely tack-free.

The "(meth) acrylic acid ester" means an acrylic acid ester and / or a methacrylic acid ester, and the "acrylic polymer" means an acrylic polymer or a methacrylic polymer. , "(Meth) acrylate" means acrylate or methacrylate.

The (meth) acrylic acid ester used as the component (A) in the resin composition of the present invention is not particularly limited.

Specific examples of the (meth) acrylic acid ester useful as the component (A) include, for example, methyl acrylate, ethyl acrylate, n-butyl acrylate, t-butyl acrylate, 2-ethylhexyl acrylate and the like. Acrylic acid ester, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, i-methacrylic acid
Butyl, t-butyl methacrylate, lauryl methacrylate, 2-ethylhexyl methacrylate, tridecyl methacrylate, stearyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, 2-methacrylate
Examples thereof include methacrylic acid esters such as hydroxyethyl, 2-hydroxypropyl methacrylate, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, glycidyl methacrylate, tetrahydrofurfuryl methacrylate and allyl methacrylate. These may be used alone or in combination of two or more.

The cured product obtained when the glass transition temperature (hereinafter referred to as Tg) as the homopolymer of the component (A) is low becomes soft, and when the Tg is high, the cured product obtained is high. Becomes harder. Therefore, in order to develop desired properties of the cured product, it is preferable to appropriately select and use the component (A) according to the Tg of the component (A) as a homopolymer.

For example, in order to develop a cured product having excellent toughness, methyl methacrylate having a Tg of 80 ° C. or higher as a homopolymer and acrylic acid 2-having a Tg of 0 ° C. or lower as a homopolymer. A mixture with ethylhexyl can be preferably used.

(B) used in the resin composition of the present invention
The component is an acrylic polymer soluble in the component (A).
Here, the term “soluble” includes the case where the component (A) is in a dispersed state.

Specific examples of the acrylic polymer (B) include, for example, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, i-butyl methacrylate, t-butyl methacrylate, lauryl methacrylate,
2-ethylhexyl methacrylate, methyl acrylate,
Examples thereof include homopolymers or copolymers of monomers selected from ethyl acrylate, n-butyl acrylate, t-butyl acrylate, 2-ethylhexyl acrylate, and the like.

Of these, in order to exhibit cured product properties excellent in transparency, a homopolymer of methyl methacrylate or a monomer having a low Tg as methyl methacrylate and a homopolymer, for example, acrylic acid n -Butyl, i-butyl acrylate, 2-ethylhexyl acrylate, n-butyl methacrylate, 2-ethylhexyl methacrylate,
Particularly preferred are copolymers with lauryl methacrylate and the like.

In the resin composition of the present invention, the use ratio of the component (A) and the component (B) is not particularly limited, but from the viewpoint of coating workability of the resin composition of the present invention,
In the total amount of 100 parts by mass of the component (A) and the component (B), the content of the component (A) is preferably 40 to 90% by mass, the content of the component (B) is 10 to 60% by mass, and more preferably (A). )
The component is in the range of 45 to 80 mass%, and the component (B) is in the range of 20 to 55 mass%.

When the proportion of the component (A) used is less than 40% by mass, that is, when the proportion of the component (B) used exceeds 60% by mass, the curing time is shortened but the viscosity of the composition increases. Then, coating workability tends to decrease. On the other hand, when the usage ratio of the component (A) exceeds 90% by mass, that is, when the usage ratio of the component (B) is less than 10% by weight, the viscosity of the composition is lowered and the coating workability is improved. Polymerization curability tends to decrease.

In the resin composition of the present invention, an aliphatic amine or an alicyclic amine used as the component (C),
At least one compound selected from the heterocyclic compounds containing a nitrogen atom exhibits an excellent effect in improving the polymerization curability.

The component (C) is not particularly limited as long as it is a compound selected from an aliphatic amine, an alicyclic amine, and a heterocyclic compound containing a nitrogen atom, and may be used alone. You may use it in combination of 2 or 3 types. The heterocyclic compound of the heterocyclic compound containing a nitrogen atom as used herein means a cyclic compound having a ring composed of two or more kinds of atoms (in addition to carbon, nitrogen, oxygen, sulfur, etc.). .

The term "aliphatic amine" as used herein means that the compound contains at least one or more nitrogen atoms, has a linear atomic arrangement (including branching), and a bond between carbon atoms is a single bond. An amine means an acyclic amine represented by an unsaturated amine containing a double bond or a triple bond between carbon atoms.

Specific examples of the aliphatic amine include, for example,
Aliphatic compounds such as n-ethylamine, n-propylamine, n-butylamine, n-octylamine, 1-methylheptylamine, 1-amino-2-propanol, isopropylamine, isobutylamine, t-butylamine, t-octylamine Primary amine, di-n-methylamine, diethylamine, di-n-butylamine, di-n-
Aliphatic secondary amines such as octylamine, diisopropylamine, diisobutylamine, tri-n-ethylamine, tri-n-butylamine, tri-n-octylamine, N, N-dimethylethanolamine, N, N-diethylethanol. Examples thereof include amines, N-methyldiethanolamine, N, N-dibutylethanolamine, aliphatic tertiary amines such as dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate and the like.

Although these are not particularly limited,
Of the aliphatic amines, from the viewpoint of excellent curability at low temperatures,
An aliphatic amine having 1 to 8 carbon atoms in the compound is preferable, and an aliphatic amine having 4 to 8 carbon atoms in the compound is more preferable. From the viewpoint of reactivity, aliphatic tertiary amines are particularly preferable.

The alicyclic amine referred to herein includes at least one nitrogen atom in the compound, unpaired electrons on the nitrogen do not delocalize, and has a property similar to that of the aliphatic amine. Carbocyclic amine.

Specific examples of the alicyclic amine include, for example,
Cyclohexylamine, 1,4-bis (aminomethyl)
Cyclohexane, dicyclohexylamine, bis (4-
Aminocyclohexyl) methane and the like can be mentioned, but these are not particularly limited.

Among these alicyclic amines, from the viewpoint of excellent curability at low temperatures, alicyclic amines having 1 or 2 rings in the compound are preferable, and alicyclic primary amines are more preferable. Alternatively, it is an alicyclic amine having one ring in the compound. From the viewpoint of reactivity, alicyclic tertiary amine is particularly preferable.

Specific examples of the heterocyclic compound containing a nitrogen atom include, for example, 1,4-diazabicyclo [2.2.
2] octane, quinuclidine, hexamethylenetetramine, piperazine, piperidine, N-methylpiperidine,
N-methylpiperazine, 2-methylimidazole, 4-
Examples thereof include dimethylaminopyridine and 3-amino-1,2,4-triazole. These can be used alone or in combination of two or more.

In the present invention, among these heterocyclic compounds containing nitrogen, from the viewpoint of low coloring property of the cured product, preferably a compound having a saturated bond, more preferably components (A) to (D). It is a tertiary amine having a heterocyclic structure such as 1,4-diazabicyclo [2.2.2] octane and quinuclidine because it has excellent storage stability when mixed and stored.

In the present invention, the proportion of the component (C) used is not particularly limited, but it is in the range of 0.001 to 10 parts by mass with respect to 100 parts by mass of the total amount of the components (A) and (B). Is preferable, and the range of 0.01 to 5 parts by mass is particularly preferable.

In the present invention, if the use ratio of the component (C) is less than 0.001 part by mass, the polymerization curability of the composition tends to be deteriorated, and if the use ratio exceeds 10 parts by mass, the polymerization and curing properties of the composition are cured. The promotion effect does not tend to improve.

The metal compound used as the component (D) in the resin composition of the present invention is a component for improving the polymerization curability of the composition.

The metal compound (D) is not particularly limited, and includes, for example, Group IA metals and Group IIA metals of the periodic table, zinc, lead, cobalt, nickel,
Examples thereof include a metal compound selected from manganese, iron and copper, and an organometallic complex in which a metal and an organic compound form a complex.

Specific examples of the organometallic complex include metal oxides or hydroxides; sodium, potassium or zinc carbonates; sodium, potassium, copper, strontium, magnesium, lead, cobalt and manganese. Acetates; Acidic phthalates of sodium and potassium; Bicarbonates; Benzoates; Phosphates; Sulfides; Methacrylates, etc., or mixtures thereof, acetylacetone, phenylacetylacetone, 2,2,6,6 -A metal complex with an organic compound selected from tetramethyl-3,5-heptadione and the like.

In the present invention, the proportion of the component (D) used is not particularly limited, but is in the range of 0.01 to 15 parts by mass with respect to 100 parts by mass of the total amount of the components (A) and (B). A range of 0.05 to 10 parts by mass is particularly preferable.

In the present invention, when the amount of the metal compound (D) used is less than 0.01 parts by mass, the polymerization curability of the resin composition tends to be lowered, and even if the amount of the metal compound (D) exceeds 15 parts by mass, the polymerization is performed. The effect of improving the curability tends to almost disappear.

In the resin composition of the present invention, a peroxide is used as the component (E). When this peroxide is used in combination with the above-mentioned component (C) and component (D), it imparts a short pot life and fast curing property to the acrylic syrup composition containing the components (A) and (B). It is the ingredient to do.

Specific examples of the peroxide (E) are not particularly limited, but t-butylperoxymaleic acid, t-amylperoxymaleic acid, t-butylperoxysuccinic acid, t -Peroxyesters such as amyl succinic acid and the like. These are -30 to
It is preferably used from the viewpoint of exhibiting fast curing property at + 50 ° C.

In the present invention, the peroxide (E) is
The range of 0.01 to 15 parts by mass is preferable with respect to 100 parts by mass of the total amount of the components (A) and (B), and
The range of 10 parts by mass is more preferable.

In the present invention, when the proportion of the peroxide (E) used exceeds 15 parts by mass, the molecular weight of the cured product decreases,
Further, the mechanical strength of the cured product tends to decrease, and the pot life of the composition tends to remain unchanged or increase.

On the other hand, the proportion of the peroxide (E) used is 0.
If the amount is less than 01 parts by mass, the curability tends to be insufficiently imparted.

In the resin composition of the present invention, if necessary,
Water can be added. In this case, water participates as a solvent for the metal salt and can adjust the reactivity and reaction rate during curing of the resin composition. When water is added in the present invention, the amount of water added is not particularly limited, and may be any amount within the range that does not impair the polymerization curability of the resin composition.

For example, the pot life of the present invention is set to -30 to +
When adjusted to the range of about 5 seconds to 20 minutes under the condition of 50 ° C., the addition amount of water is 0.05 with respect to 100 parts by mass of the total amount of the components (A) and (B). The range of 5 to 5 parts by mass is preferable, and the range of 0.1 to 3 parts by mass is more preferable. If the amount of water added exceeds 5 parts by mass, the curability of the composition tends to decrease.

If desired, the composition of the present invention is soluble in (meth) acrylic acid ester (A) for the purpose of adjusting the viscosity of the resin composition or improving the trackability of the cured product to the road surface. A different plasticizer (F) can be added.

Specific examples of the plasticizer (F) include dibutyl phthalate, di-n-octyl phthalate, di-2-ethylhexyl phthalate, octyl decyl phthalate, di-n-decyl phthalate, diisodecyl phthalate, butyl benzyl. Phthalates such as phthalate, di-2-ethylhexyl adipate, octyl didecyl adipate, di-2-ethylhexyl sebacate, dibutyl sebacate, di-2-ethylhexyl sebacate, polypropylene glycol, chlorinated paraffin; adipic acid , Azelaic acid type, sebacic acid type and phthalic acid type polyester plasticizers; epoxidized oil,
Epoxy polymer plasticizers such as epoxidized fatty acid ester can be used. These may be used alone or in combination of two or more.

In the present invention, a plasticizer may be added,
The amount added is not particularly limited. For example, the working life of the present invention is about 5 seconds under the condition of -30 to + 50 ° C.
When adjusting to a range of 20 minutes, (A) component and (B)
The range of 0.1 to 25 parts by mass is preferable, and the range of 0.5 to 20 parts by mass is more preferable, based on 100 parts by mass of the total amount of the components.

In the present invention, when the added amount of the plasticizer exceeds 25 parts by mass, the compression strength and stain resistance of the obtained cured product tend to be lowered, and when it is less than 0.1 parts by mass. On the other hand, the finish of the coating film tends to be poor.

The composition of the present invention contains, if necessary, at least two polymerizable functional groups in one molecule other than the components (A) to (E) for the purpose of improving the durability of the cured product. A compound (F) having a can be added.

Specific examples of such a compound (F) include, for example, ethylene glycol di (meth) acrylate, 1,2-propylene glycol di (meth) acrylate, 1,3-butylene glycol di (meth) acrylate, Alkanediol di (meth) acrylates such as 1,6-hexanediol di (meth) acrylate;
Polyoxyalkylene glycol di (meth), such as diethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, triethylene glycol (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate Acrylate; divinylbenzene and the like can be mentioned. These may be used alone or in combination of two or more.

In the present invention, at least 2 per molecule
When the compound (F) having a single polymerizable functional group is added, its addition amount is not particularly limited. For example, the pot life of the present invention is about 5 under the condition of -30 to + 50 ° C.
When adjusting in the range of seconds to 20 minutes, 0.1 to 3 with respect to 100 parts by mass of the total amount of the components (A) and (B).
The range of 0 parts by mass is preferable, and the range of 1 to 20 parts by mass is more preferable.

In the present invention, at least 2 in one molecule
When the amount of the compound (F) having a number of polymerizable functional groups is more than 30 parts by mass, the strength tends to decrease. The curability tends to decrease.

Paraffin wax and / or wax may be added to the composition of the present invention, if necessary, in order to suppress the effect of inhibiting polymerization of oxygen on the surface of the cured coating film and to improve the stain resistance. You can

The paraffin and / or wax are not particularly limited, and examples thereof include known paraffin wax, polyethylene wax, higher fatty acids such as stearic acid, and the like. In addition, 2 with different melting points
It is also possible to use together more than one paraffin and / or wax.

The amount of paraffin and / or wax added is not particularly limited. For example, the pot life of the present invention is -3
When adjusted to a range of about 5 seconds to 20 minutes under the condition of 0 to + 50 ° C., 0.1 to 5 parts by mass with respect to 100 parts by mass of the total amount of the components (A) and (B). Is preferable, and a range of 0.2 to 2 parts by mass is more preferable.

If the amount of paraffin and / or wax added exceeds 5 parts by mass, the appearance of the cured coating film tends to be poor, and if it is less than 0.1 parts by mass, the effect of inhibiting polymerization of oxygen on the surface of the coating film is exhibited. And the stain resistance effect of the cured coating film tends not to be sufficiently exhibited.

An ultraviolet absorber may be added to the resin composition of the present invention for the purpose of further improving the weather resistance of the resulting cured product. As the ultraviolet absorber, known ones such as benzophenone type ultraviolet absorber, triazine type ultraviolet absorber and benzotriazole type ultraviolet absorber can be used and are not particularly limited.

Specific examples of the ultraviolet absorber include, for example,
2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octyloxybenzophenone, 2-hydroxy-4-decyloxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2-hydroxy-4,4'-dimethoxybenzophenone , 2-hydroxy-4,4'-dibutoxybenzophenone, etc.
Derivatives of hydroxybenzophenone; 2- (2'-hydroxy-5'-methylphenylyl) benzotriazole, 2- (2'-hydroxy-3,5'-ditertiarybutylphenylyl) benzotriazole, 2- [2 ′-
Benzotriazole derivatives such as hydroxy-3,5'-bis (2,2'-dimethylpropyl) phenyl] benzotriazole and / or halogen-substituted derivatives thereof; phenyl salicylate, p-ethylphenyl salicylate, p
Examples thereof include esters of salicylic acid such as tert-butylphenyl salicylate. These may be used alone or in combination of two or more.

When the ultraviolet absorber is added in the present invention, the addition amount is not particularly limited. For example, when the pot life of the present invention is adjusted to the range of about 5 seconds to 20 minutes under the condition of -30 to + 50 ° C, the total amount of the component (A) and the component (B) is 100 parts by mass. For 0.01 to
The range of 10 parts by mass is preferable, and the range of 0.01 to 5 parts by mass is more preferable.

If the amount of the ultraviolet absorber added exceeds 10 parts by mass, the effect of imparting weather resistance tends not to improve, and
If the amount is less than 01 parts by mass, the effect of improving the weather resistance tends not to be sufficiently exhibited.

The method of polymerizing the resin composition of the present invention is not particularly limited, and the components (A) to (E) may be polymerized and cured into a desired shape in a lump or divided.

For example, the resin composition is prepared by previously mixing the above-mentioned components (A) to (E) together and then pouring the resin composition into a mold to polymerize it; the components (A) and (B). A method in which the component (C) and the component (D) are mixed in advance in a mixture of the components, and the component (E) is added thereto and polymerized; (A)
The components and the component (B) are mixed in advance, the mixture is divided into two, the component (E) is added to one side, the components (C) and (D) are added to the other side, and they are separately dissolved and polymerized. Examples include a method of mixing the two liquids immediately before polymerization.

The resin composition of the present invention exhibits a rapid curing property under a wide range of temperature conditions from a low temperature to a high temperature region by appropriately selecting each component. Especially, -30 ℃
In the temperature range of + 50 ° C, rapid curing can be performed within 15 minutes, preferably within 10 minutes. Therefore, it can be suitably used as a coating material for outdoor use.

Specific examples of outdoor uses include, for example, road surfaces such as concrete and asphalt; coating materials for floor surfaces and wall surfaces; and coating materials for marking materials in general.

Further, the resin composition of the present invention exhibits rapid curing property under a wide range of temperature conditions, and therefore various coating methods which require rapid curing property, for example, ladle method, coating method, thin mortar method. It is very useful in a coating method, a mortar thick coating method, a method of spray-mixing two or more liquids immediately before coating and curing.

The cured product obtained by polymerizing the resin composition of the present invention has a transparent feeling, low yellowness, and excellent weather resistance. Therefore, the resin composition of the present invention is very useful particularly when a cured product that is colored in a light color is obtained.

The coating material of the present invention comprises (meth) acrylic acid ester (A), acrylic polymer (B) soluble in component (A), tertiary amine having a heterocyclic structure, and aliphatic tertiary It contains at least one compound (C) selected from a primary amine or an alicyclic tertiary amine, a metal compound (D), and a peroxide (E). These (A)-(E)
The components may be the same as the components (A) to (E) described above. In the coating material of the present invention, various additives, aggregates, fillers and the like are appropriately selected and mixed in the required amounts to be used in order to develop a desired coating performance.

For example, stabilization of the adhesiveness to the base,
For the purpose of improving the durability of the adhesive strength between the resin composition and the filler, γ-methacryloxypropyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, N-β- (aminoethyl) -γ- A silane coupling agent such as aminopropyltrimethoxysilane or γ-mercaptopropyltrimethoxysilane can be added.

For the purpose of stabilizing the curability of the composition, tributyl phosphite, tri (2-ethylhexyl)
Stabilizers such as phosphites such as phosphite, tridecyl phosphite, tristearyl phosphite, tris (nonylphenyl) phosphite and triphenyl phosphite can be added.

For the purpose of improving the storage stability of the composition,
Hydroquinone, hydroquinone monomethyl ether, 2,
A polymerization inhibitor such as 4-dimethyl-t-butylphenol can be added.

As the aggregate, it is preferable to use an aggregate having an average particle size of 10 μm or more and an oil absorption amount of 25 cc or less with respect to 100 g of linseed oil.

Specific examples of the aggregate include, for example, sand, silica sand, quartz sand, or colored or fired products thereof; rock powder such as quartz powder or silica sand powder; fired and cured colored pottery or ceramic base. Pulverized product: zinc white, calcium carbonate, alumina, glass beads and the like.

In particular, in order to improve the coating workability and the self-leveling property, it is preferable that the coating material of the present invention contains an aggregate having different particle diameters.

Further, in order to obtain a coating material having thixotropy, a filler such as a coloring pigment or a dye, in addition to silica powder such as Aerosil, may be added to the coating material of the present invention.

Specific examples of color pigments and dyes include titanium oxide, barium sulfate, carbon black, chrome vermillion, red iron oxide, ultramarine blue, cobalt blue, and the like.
Examples include phthalocyanine blue and phthalocyanine green.

The blending amount of these fillers is not particularly limited, but generally, the resin composition 100 of the present invention is used.
It is preferable that the content is 900 parts by mass with respect to parts by mass, because a cured coating film having a good balance of various physical properties tends to be obtained. In addition, various antifoaming agents and leveling agents may be added for the purpose of adjusting the surface appearance of the cured coating film.

When the resin composition and the coating material of the present invention are applied to the floor surface or wall surface of concrete, asphalt, steel plate or the like, they may be directly applied to the object to be coated, but if necessary, It is preferable to apply a primer treatment to the coated material in advance and then apply the primer.

The coating method of the present invention includes a spray method,
Examples of the method include, but are not limited to, a gold trowel finishing method, a brush coating method, and roller coating.

Further, in the present invention, the appearance of the cured coating film such as smoothness and non-slip property can be appropriately formed as desired.

Specifically, for example, a coating material containing no or only a part of aggregate is applied to an object to be coated to form a coating film, and the coating material surface is cured before the coating material is cured. By spreading the aggregate on the surface of the cured coating, a non-slip cured coating can be obtained in which the aggregate is partially projected on the surface of the cured coating.

At this time, in the case of using the coating material in which the aggregate is mixed in advance, the kind and the amount of the aggregate may be selected according to the purpose of coating.

A relatively thin coating film, for example, 0.2 to 1 mm
When applying the coating film of, spray method, brush coating method,
A coating method such as a roller coating method is preferable. The amount of aggregate used in this case is preferably in the range of 30 to 100 parts by mass with respect to 100 parts by mass of the resin composition of the present invention.

When forming a thicker coating film, for example, a coating film having a thickness of 1 to 30 mm, a gold trowel finishing method is preferable. The amount of aggregate used in this case is preferably in the range of 100 to 900 parts by mass with respect to 100 parts by mass of the resin composition of the present invention.

In order to obtain a cured coating film having a smooth appearance, a small amount of aggregate may be added, but considering the physical properties of the cured coating film, it is preferably about 100 parts by mass.

Further, in order to obtain a thick coating film, a large amount of aggregate may be blended, but from the economical viewpoint and the curability viewpoint,
It is preferable that the amount of aggregate is about 900 parts by mass.

The cured product obtained by polymerizing the resin composition of the present invention has excellent weather resistance. In particular, the cured product Y
The I value exhibits an epoch-making effect of decreasing with time. Thus, the resin composition of the present invention,
It is very useful.

[0086]

EXAMPLES The present invention will be further described below with reference to examples and comparative examples, but the present invention is not limited to these examples. In addition, "part" in an example represents a mass part. The evaluations in the examples were carried out by the following evaluation methods.

[Evaluation method] 1. Polymerization behavior Potential time: Peroxide (E) was added to the obtained acrylic syrup composition, and stirring was started with a stirring bar until the stirring became impossible due to an increase in viscosity. The time (minutes) was measured.

Curing time: The resin composition obtained was heated to 20 ° C.
Polyethylene terephthalate (hereinafter PET)
The film was coated on the film by a gold trowel finishing method, and the time (minutes) from the addition of the peroxide (E) to the time when the coating film surface was completely tack-free was measured. The term "tack-free" used herein means a state in which gauze is placed on the surface of a cured product, a load of 500 g is applied for 1 minute, and then the cured product is tilted at 30 degrees with respect to the horizontal direction and the gauze slides down. The temperature in the table means the temperature from the mixing of the components to the coating.

2. Weather resistance With respect to the obtained cured product, the yellowness index (hereinafter referred to as YI value) immediately after the cured product was obtained (0 hour), after 100 hours and after 500 hours, was calculated by the following methods. However, this value is described in the table.

Calculation method of YI value: Using a color difference analyzer (Model 307 manufactured by Hitachi, Ltd.), JIS standard K-
According to 7103, the color difference of the cured product was measured. next,
The YI value was calculated from the X, Y, and Z stimulus values and the following general formula.

[0091]

[Equation 1]

The weather resistance test (100 hours, 500 hours) was carried out by the following method. Weather resistance test: For the obtained cured product, using a sunshine weatherometer (WE-SUN-DC manufactured by Suga Test Instruments Co., Ltd.), a black panel temperature of 63 ° C., a cycle of water 12 minutes / drying 60 minutes, 100 hours each. And exposed for 500 hours.

Example 1 Methyl methacrylate 60 parts 2-Hydroxyethyl methacrylate 5 parts 2-Ethylhexyl acrylate 10 parts Triethylene glycol dimethacrylate 5 parts Dioctyl terephthalate 1.5 parts Paraffin wax (melting point 47 ° C.) 25 parts paraffin wax (melting point 66 ° C.) 0.25 parts The above compounds are mixed and heated to + 50 ° C. with stirring, and 25 parts by mass of polymethyl methacrylate are added little by little to dissolve and then cooled to room temperature. did. Subsequently, 0.5 parts of TINUVIN 328 (ultraviolet absorber: manufactured by Ciba Geigy), 1,4-diazabicyclo [2.2.2].
0.3 parts of octane and 3 parts of calcium hydroxide were added and stirred to obtain a mixture.

0.9 part of t-butylperoxymaleic acid (hereinafter referred to as PMA) was added to the obtained mixture, and the mixture was stirred to prepare a resin composition. A cured product was obtained by applying a gold trowel finishing method at 20 ° C. so that the thickness was about 3 mm.

As a result, the polymerization behavior was such that the pot life was about 1 minute and the curing time was about 5 minutes. The initial (0 hour) YI value of the obtained cured product was 6.5. The cured product was subjected to a weather resistance test and found to be 100
The YI value after 5.6 hours and the YI value after 500 hours were 5.
It was 0.

Next, a mixture was prepared again under the same conditions as above, and this was stored in a constant temperature bath at + 50 ° C. for 30 days.
To this stored mixture, 0.9 part of PMA was added and stirred to prepare a resin composition. This was rapidly coated on a PET film by a gold trowel finishing method at a temperature of 20 ° C. to a thickness of about 3 mm to obtain a cured product. As a result, this polymerization behavior has a pot life of about 1 minute and a curing time of about 4 minutes.
It was a minute.

[Examples 2 to 9] A resin composition was obtained in the same manner as in Example 1 except that the compositions and temperatures shown in Table 1 were used. A cured product was obtained from the obtained resin composition in the same manner as in Example 1 under the temperature conditions shown in Table 1. Table 1 shows the results of evaluation of the polymerization behavior (pot life, curing time) and YI value of the obtained cured product. Further, in the same manner as in Example 1 except that the composition and temperature shown in Table 1 were used,
Each mixture was prepared again and this was stored for 30 days in the +50 degreeC thermostat. Component (E) shown in Table 1 was added to each of the stored mixtures, and the mixture was stirred to prepare a resin composition. Using this resin composition, cured products were obtained under the temperature conditions shown in Table 1 in the same manner as in Example 1. Table 1 shows the results of evaluation of the polymerization behavior (pot life, curing time) and YI value of the obtained cured product.

[Examples 10 and 11] The same operation as in Example 1 was carried out except that the compositions and temperatures shown in Table 1 were used to obtain a mixture, which was followed by the addition of 0.2 part of water and 0.9 parts of PMA. Parts were added and stirred to prepare resin compositions. Using this resin composition, cured products were obtained under the temperature conditions shown in Table 1 in the same manner as in Example 1. Table 1 shows the results of evaluation of the polymerization behavior (pot life, curing time) and YI value of the obtained cured product. In addition, a mixture was prepared again in the same manner as in Example 1 except that the composition and temperature shown in Table 1 were used, and the mixture was stored in a constant temperature bath at + 50 ° C. for 30 days. Water was added to each of the stored mixtures.
2 parts and PMA 0.9 parts were added, respectively, and it stirred, and the resin composition was prepared. Under the temperature conditions shown in Table 2, cured products were obtained in the same manner as in Example 1. Polymerization behavior (pot life, curing time) and Y of the obtained cured product
The results of evaluating the I value are shown in Table 1.

Comparative Example 1 Methyl methacrylate 60 parts 2-Hydroxyethyl methacrylate 5 parts 2-Ethylhexyl acrylate 10 parts Triethylene glycol dimethacrylate 5 parts Dioctyl terephthalate 1.5 parts Paraffin wax (melting point 47 ° C.) 25 parts paraffin wax (melting point 66 ° C.) 0.25 parts The above compounds are mixed and heated to + 50 ° C. with stirring, and 25 parts by mass of polymethyl methacrylate are added little by little to dissolve and then cooled to room temperature. did. Subsequently, 0.5 parts of TINUVIN 328 (ultraviolet absorber: manufactured by Ciba Geigy) and 3 parts of calcium hydroxide were added thereto and stirred to obtain a mixture.

To the obtained mixture, 0.9 part of PMA was added and stirred to prepare a resin composition, which was immediately finished on a PET film under a condition of 20 ° C. so as to have a thickness of about 3 mm. It was applied by the method to obtain a cured product. As a result, the coating film was not completely polymerized and cured even after 2 hours from the preparation of the resin composition.

A mixture was prepared again under the same conditions as above, and this was stored in a constant temperature bath at + 50 ° C. for 30 days.
To this stored mixture, 0.9 parts of PMA was added and stirred to prepare a resin composition. This was immediately coated on a PET film by a gold trowel finishing method at a temperature of 20 ° C. so as to have a thickness of about 3 mm. As a result, even after 2 hours had passed since the resin composition was prepared, it was not completely polymerized and cured.

[Comparative Examples 2 to 4] Mixtures were prepared in the same manner as in Example 1 except that the compositions and temperatures shown in Table 1 were used, and the component (E) shown in Table 1 was added thereto. , A resin composition was prepared. The obtained resin composition was applied under the temperature conditions shown in Table 1 in the same manner as in Example 1. This polymerization behavior (pot life, curing time)
The results of evaluating the YI value and the YI value are shown in Table 1. In addition, a mixture was prepared again in the same manner as in Example 1 except that the composition and temperature shown in Table 1 were used, and the mixture was stored in a constant temperature bath at + 50 ° C. for 30 days. Component (E) shown in Table 1 was added to each of the stored mixtures, and the mixture was stirred to prepare a resin composition. This resin composition was applied under the temperature conditions shown in Table 1 in the same manner as in Example 1. The results of evaluation of this polymerization behavior (pot life, curing time) and YI value are shown in Table 1.

[Example 12] A resin composition was prepared under the same conditions as in Example 1, and immediately 150 x 150 x 3 (unit: m
After injecting into the mold of m), it was polymerized and cured at 90 ° C. to obtain a cured product. As a result, the polymerization behavior was such that the pot life was about 0.
5 minutes, curing time was 4 minutes. The YI value of the obtained cured product was 6.4 at the initial stage (0 hours), 5.4 after 100 hours, and 4.8 after 500 hours. Next, a mixture was prepared again in the same manner as in Example 1 and stored in a constant temperature bath at + 50 ° C. for 30 days. PMA was added to this stored mixture.
The resin composition obtained by adding 0.9 parts and stirring was immediately poured into a mold of 150 × 150 × 3 (unit: mm) and polymerized and cured at 90 ° C. to obtain a cured product. It was As a result, the polymerization behavior was such that the pot life was about 0.5 minutes and the curing time was 4 minutes.

[Example 13] A cured product was obtained in the same manner as in Example 1 except that a PET film was coated to a thickness of 0.5 mm. The evaluation results are shown in Table 1.

[0105]

[Table 1]

The abbreviations used in the table are as follows. * 1): polymethyl methacrylate MMA: methyl methacrylate EHA: 2-ethylhexyl acrylate HEMA: 2-hydroxyethyl methacrylate BA: n-butyl acrylate DABCO: 1,4-diazabicyclo [2.2.2] octane DMPT : Dimethyl-p-toluidine PMA: t-butylperoxymaleic acid PSA: t-butylperoxysuccinic acid BPO: benzoyl peroxide T-328: Tinuvin 328 (manufactured by Ciba-Geigy: UV absorber)

Example 14 Methyl methacrylate 70 parts 2-Ethylhexyl acrylate 5 parts Triethylene glycol dimethacrylate 5 parts Dioctyl terephthalate 1.5 parts Paraffin wax (melting point 47 ° C.) 0.25 part Paraffin wax (melting point 66 ° C.) 0.25 parts The above compounds were mixed and heated to + 50 ° C. while stirring, and 25 parts by mass of polymethylmethacrylate was added little by little to dissolve therein, and then cooled to room temperature. Subsequently, 0.5 parts of TINUVIN 328 (UV absorber: manufactured by Ciba-Geigy), 0.4 parts of n-butylamine, and 2 parts of calcium hydroxide were added thereto and stirred to obtain a mixture. ,

PMA (0.9 parts) was added to the obtained mixture and the mixture was stirred to prepare a resin composition, which was immediately finished on a PET film under the conditions of 20 ° C. so as to have a thickness of about 3 mm. It was applied by the method to obtain a cured product. As a result, the polymerization behavior was such that the pot life was about 1 minute and the curing time was about 4 minutes. YI of the initial (0 hour) of the obtained cured product
The value was 6.6. A weather resistance test was carried out on this cured product using a sunshine weatherometer. The YI value after 100 hours was 6.2, and the YI value after 500 hours was YI.
The value was 6.3.

Next, a mixture was prepared again under the same conditions as above, and this was stored in a constant temperature bath at + 50 ° C. for 30 days.
To this stored mixture, 0.9 parts of PMA was added and stirred, and this was rapidly coated on a PET film by a gold trowel finishing method at a temperature of 20 ° C. to a thickness of about 3 mm,
A cured product was obtained. As a result, the polymerization behavior was such that the pot life was about 1.2 minutes and the curing time was about 4.3 minutes.

[Examples 15 to 22, 25 to 32] A resin composition was obtained in the same manner as in Example 14, except that the compositions and temperatures shown in Table 2 were used. The obtained resin composition,
A cured product was obtained in the same manner as in Example 14 under the temperature conditions shown in Table 2. Table 2 shows the results of evaluation of the polymerization behavior (pot life, curing time) and YI value of the obtained cured product. Next, a mixture was prepared again in the same manner as in Example 14 except that the composition and temperature shown in Table 2 were used.
This was stored in a constant temperature bath at + 50 ° C. for 30 days. Component (E) shown in Table 2 was added to each of the stored mixtures, and the mixture was stirred to prepare a resin composition. Under the temperature conditions shown in Table 2, cured products were obtained in the same manner as in Example 14. The results of evaluating the polymerization behavior (pot life, curing time) and YI value of the obtained cured product are as follows:
The results are shown in Table 2.

Example 23 The same operation as in Example 14 was carried out except that the composition and temperature shown in Table 2 were used to obtain a mixture. 0.2 parts of water and 0.9 part of PMA were added to the mixture. Resin compositions were prepared by adding and stirring. Table 2
Under the temperature conditions described, cured products were obtained in the same manner as in Example 14. The results of evaluating the polymerization behavior (pot life, curing time) and YI value of the obtained cured product are shown in Table 2.
It was shown to. Next, a mixture was prepared again in the same manner as in Example 14 except that the composition and temperature shown in Table 2 were used, and the mixture was stored in a + 50 ° C. thermostat for 30 days. 0.2 parts of water and PMA were added to each of the stored mixtures.
0.9 parts of each was added and stirred to prepare a resin composition. Under the temperature conditions shown in Table 2, cured products were obtained in the same manner as in Example 14. Table 2 shows the results of evaluation of the polymerization behavior (pot life, curing time) and YI value of the obtained cured product.

Example 24 The same operation as in Example 14 was carried out except that the composition and temperature shown in Table 2 were used, and after cooling to room temperature, 50 parts of calcium carbonate and 50 parts of titanium oxide were added to obtain a mixture. Got To this mixture, PMA 0.9
A resin composition was prepared in the same manner as in Example 14, except that parts were added and coating was carried out on a PET film by a trowel finishing method at -20 ° C to a thickness of about 3 mm. Under the temperature conditions shown in Table 2, cured products were obtained in the same manner as in Example 14. Table 2 shows the results of evaluation of the polymerization behavior (pot life, curing time) and YI value of the obtained cured product. Next, the mixture was prepared again and stored in a constant temperature bath at + 50 ° C. for 30 days. To this stored mixture, the same operation as in Example 14 was performed except that 0.9 part of PMA was added and coating was performed on a PET film by a trowel finishing method at -20 ° C to a thickness of about 3 mm. , A resin composition was prepared. Under the temperature conditions shown in Table 2, cured products were obtained in the same manner as in Example 14. Table 2 shows the results of evaluation of the polymerization behavior (pot life, curing time) and YI value of the obtained cured product.

Comparative Example 5 Methyl methacrylate 70 parts 2-Ethylhexyl acrylate 5 parts Triethylene glycol dimethacrylate 5 parts Dioctyl terephthalate 1.5 parts Paraffin wax (melting point 47 ° C.) 0.25 parts Paraffin wax (melting point 66 ° C.) 0.25 parts The above compounds were mixed and heated to + 50 ° C. while stirring, and 25 parts by mass of polymethylmethacrylate was added little by little to dissolve therein, and then cooled to room temperature. Subsequently, 0.5 parts of TINUVIN 328 (UV absorber: manufactured by Ciba-Geigy) and 0.4 part of n-butylamine were added thereto and stirred to obtain a mixture. The resulting mixture was added with PMA0.
9 parts were added and stirred to prepare a resin composition. This was immediately applied onto a PET film under a condition of -20 ° C to a thickness of about 3 mm. As a result, even after 2 hours had passed since the resin composition was prepared, it was not completely polymerized and cured.

Next, the above mixture was prepared again, and this was
It was stored in a constant temperature bath at 50 ° C. for 30 days. To this stored mixture, 0.9 part of PMA was added and stirred to prepare a resin composition, which was immediately coated on a PET film by a trowel finishing method at -20 ° C to a thickness of about 3 mm. did. As a result, even after 2 hours had passed since the resin composition was prepared, it was not completely polymerized and cured.

[Comparative Examples 6 to 10] Mixtures were prepared in the same manner as in Example 14 except that the compositions and temperatures shown in Table 2 were used, and the component (E) shown in Table 2 was added thereto. , A resin composition was prepared. The obtained resin composition was applied under the temperature conditions shown in Table 2 in the same manner as in Example 14. The results of evaluating the polymerization behavior (pot life, curing time) and YI value are shown in Table 2. In addition, a mixture was prepared again in the same manner as in Example 1 except that the composition and temperature shown in Table 2 were used, and this was +50.
It was stored in a constant temperature bath at 30 ° C. for 30 days. The component (E) shown in Table 2 was added to each of the stored mixtures, and the mixture was stirred to prepare a resin composition. This was applied under the temperature conditions shown in Table 2 in the same manner as in Example 14. The results of evaluating the polymerization behavior (pot life, curing time) and YI value are shown in Table 2.

[Example 33] A mixture and a resin composition were prepared under the same conditions as in Example 14 except that the composition and temperature shown in Table 2 were used. This resin composition was applied in the same manner as in Example 14 except that the thickness was about 0.5 mm to obtain a cured product. Initial stage of the obtained cured product (0 hours)
YI value of was 5.7. Further, when a weather resistance test was conducted, the YI value after 100 hours was 5.3, and the YI value after 500 hours was 5.1.

The above mixture is then re-prepared at + 50 ° C.
It was stored for 30 days in the constant temperature bath. In this stored mixture,
The component (E) shown in Table 1 was added and stirred to prepare a resin composition, which was quickly coated on a PET film in the same manner as in Example 14 so that the thickness was about 0.5 mm. Worked to obtain a cured product. As a result, the polymerization behavior was such that the pot life was about 1.7 minutes and the curing time was about 5.2 minutes.

[0118]

[Table 2]

The abbreviations used in the table are as follows. * 1): Polymethylmethacrylate MMA: Methyl methacrylate EHA: 2-Ethylhexyl acrylate 2-DMAE: 2-Dimethylaminoethanol DMPT: Dimethylparatoluidine Ca (OH) ₂ : Calcium hydroxide Mg (OH) ₂ : Hydroxyl Magnesium 2EHA Ca: 2% calcium ethylhexanoate 5% solution Ca methacrylate: calcium methacrylate PMA: t-butyl peroxymaleic acid PSA: t-butyl peroxysuccinate BPO: benzoyl peroxide 3G: triethylene glycol dimethacrylate 9PG: Polypropylene glycol dimethacrylate T-328: Tinuvin 328 (manufactured by Ciba-Geigy: UV absorber) TP: Tinubin P (manufactured by Ciba-Geigy: UV absorber)

Comparative Example 1 is an example in which the component (C) of the present invention was not used. In this case, the resin composition does not thicken,
The pot life could not be measured. Moreover, since this resin composition was not completely cured, the YI value could not be measured. Further, in the case of the resin composition using the mixture stored under the condition of + 50 ° C. for 30 days as well, similarly, the resin composition was not completely cured, so that the pot life and the YI value could not be measured.

Comparative Example 2 is an example in which the component (D) of the present invention was not used. In this case, the resin composition does not thicken,
The pot life could not be measured. Moreover, since this resin composition was not completely cured, the YI value could not be measured. Further, when the resin composition prepared by using the mixture stored for 30 days under + 50 ° C. was not similarly cured, the YI value could not be measured.

Comparative Example 3 is an example in which dimethylparatoluidine was used in place of the component (C) of the present invention. In this case, the curing time at low temperature was long, the obtained cured product had a high YI value from the initial (0 hour), and further yellowed after the weather resistance test.

Comparative Example 4 is an example in which aniline was used instead of the component (C) of the present invention. In this case, the obtained cured product had a high YI value from the initial stage (0 hours), and after the weather resistance test, turned considerably deeply yellow.

Comparative Example 5 is an example in which the component (D) of the present invention was not used. In this case, the resin composition does not thicken,
The pot life was immeasurable. Further, since this resin composition was not completely cured, the curing time and YI value were also unmeasurable. Further, similarly, the resin composition using the mixture stored under + 50 ° C. for 30 days also did not completely cure, so that the pot life, curing time, and YI value could not be measured.

Comparative Example 6 is an example in which the component (C) of the present invention was not used. In this case, the resin composition does not thicken,
The pot life could not be measured. In addition, the YI value could not be measured because the resin composition was not completely cured. Further, when the resin composition prepared by using the mixture stored for 30 days under + 50 ° C. was not similarly cured, the YI value could not be measured.

Comparative Examples 7 to 9 are examples in which aniline, p-anisidine and p-toluidine were used instead of the component (C) of the present invention. In this case, the obtained cured product had a high YI value from the beginning, and further yellowed after the weather resistance test.

Comparative Example 10 is an example in which dimethylparatoluidine was used instead of the component (C) of the present invention. In this case, the curing time at low temperature was long, the obtained cured product had a high YI value from the beginning, and further yellowed after the weather resistance test.

[0128]

EFFECTS OF THE INVENTION The resin composition of the present invention can provide a cured product having excellent weather resistance, and thus can be suitably used as a coating material applied to outdoor applications. In particular, after being applied in a thin film form, it can be polymerized and cured in a short time, under a wide range of temperature conditions from a low temperature to a high temperature region, has a short pot life, and can be rapidly cured,
It is widely applicable to applications that require coating in a short time, and is very useful industrially. Furthermore, the resin composition of the present invention exerts an epoch-making effect that the YI value of the cured product thereof decreases with time, and is particularly suitable for outdoor use.

   ─────────────────────────────────────────────────── ─── Continued front page    F-term (reference) 4J011 AA03 BA04 FA00 FA01 NA13                       NA30 NA34 PA69 PB06 PB40                       PC02 PC08                 4J015 CA08 CA14                 4J026 AA45 BA27 DB02 DB16 GA07                 4J038 CG141 CG142 FA121 FA141                       FA151 FA161 GA03 GA07                       HA066 HA346 HA416 JA32                       JA66 JB02 JB03 JB06 JB09                       JB25 JB27 JB33 JB38 JC38                       KA03 NA11 NA12 NA27 PA19                       PC04

Claims (7)

[Claims] 1. A (meth) acrylic acid ester (A),
At least one compound (C) selected from an acrylic polymer (B) soluble in the component (A), a heterocyclic compound containing a nitrogen atom, an aliphatic amine, or an alicyclic amine, a metal compound (D ), And a resin composition containing a peroxide (E). 2. The proportion of component (A) is 40 to 90 mass%,
The ratio of the component (C) is 0.001 to 10 parts by mass, and the ratio of the component (D) is 0.01 to 15 parts by mass with respect to 100 parts by mass of the total amount of the component (B) of 10 to 60 mass%. Department,
The resin composition according to claim 1, wherein the ratio of the component (E) is 0.01 to 15 parts by mass. 3. The resin composition according to claim 1, wherein the peroxide (E) is a peroxy ester. 4. In the component (C), a heterocyclic compound containing a nitrogen atom is a tertiary amine having a heterocyclic structure, an aliphatic amine is an aliphatic tertiary amine, and an alicyclic amine is an alicyclic ring. The resin composition according to claim 1, which is a tertiary amine. 5. A heterocyclic compound containing a nitrogen atom in the component (C) is 1,4-diazabicyclo [2.2.2].
The resin composition according to claim 1, which is octane and / or quinuclidine. 6. A cured product obtained by polymerizing and curing the resin composition according to claim 1. 7. A (meth) acrylic acid ester (A),
At least one compound selected from the acrylic polymer (B) soluble in the component (A), a tertiary amine having a heterocyclic structure, an aliphatic tertiary amine, or an alicyclic tertiary amine ( A coating material containing C), a metal compound (D), and a peroxide (E).