JP2000063701A - Coating composition - Google Patents

Abstract

[PROBLEMS] To form a crosslinked cured film having excellent abrasion resistance, weather resistance, and excellent surface smoothness, heat resistance, chemical resistance, durability, and adhesion to a substrate. An energy ray-curable coating material composition is obtained. (A) At least one selected from poly (meth) acrylates of mono- or polypentaerythritol
(B) urethane poly (meth) having at least two radically polymerizable unsaturated double bonds in one molecule
At least one acrylate compound, (C) poly [(meth) acryloyloxyalkyl] (iso) cyanurate represented by the general formula (II) or (III), (D) an ultraviolet absorber, and (E) a hindered amino ether-based compound. A coating composition comprising a light stabilizer and (F) a photopolymerization initiator.

Description

DETAILED DESCRIPTION OF THE INVENTION [0001] [0001] The present invention relates to an active energy ray.
Irradiation has excellent surface resistance, especially abrasion resistance and weather resistance
Surface smoothness, heat resistance, chemical resistance, durability and substrate
Coating material capable of forming a cross-linked cured film with excellent adhesion to materials
Composition. [0002] 2. Description of the Related Art Polymethyl methacrylate resin, polymer
Tacrylimide resin, polycarbonate resin, polystyrene
Synthetic resin molded products manufactured from Len resin, AS resin, etc.
Is not only lightweight and shock-resistant, but also transparent
Is also good.
For seed lamp lenses, glazing, instrument covers, etc.
It has become widely used. Especially headlamp lens
About car weight reduction and design to improve fuel efficiency
The use of plastic materials is increasing due to the diversification of
You. However, on the other hand, these synthetic resin molded products
Insufficient abrasion resistance causes contact with other hard objects,
The surface is easily damaged by rubbing and scratching. Ma
When used as the above-mentioned automotive material,
Its weather resistance is also an important performance. [0003] The disadvantages of such synthetic resin molded articles are improved.
Various methods have been studied in the past,
For example, a coating made of a silicon-based or melamine-based resin composition
Apply the covering material to the surface of the synthetic resin molded product, heat
How to form a bridge coating to improve wear resistance,
After applying the resin composition consisting of cal polymerizable monomer,
To form a crosslinked film by irradiating reactive energy rays
(JP-A-56-122840)
Information). [0004] However, by these methods, a synthetic resin is formed.
Although the wear resistance of the molded product surface is improved to some extent, the former
The method is resistant to heat shock, hot water, etc. and chemical resistant
Insufficient properties, and the latter method requires durability and chemical resistance.
Although it has excellent properties, it is satisfactory in terms of weather resistance
There was no. In particular, the weather resistance of the synthetic resin molded product
In case of poor quality, such as polycarbonate resin
In that case, even if the weather resistance of the surface hardened film itself is good,
Active energy such as ultraviolet light contained in sunlight passing through the coating
The base material itself is deteriorated by the rugged wire, and the molded product
Yellowing, cracking of the cured film on the surface,
The coating peels off. [0005] In view of these circumstances, the present inventors have developed an anti-friction coating.
With a resin composition with excellent wear resistance, weather resistance, durability and chemical resistance
To obtain a poly (medium or polypentaerythritol)
T) acrylate, at least two radiographs per molecule
Urethane poly (meth) having polymerizable unsaturated double bond
Acrylate compound and poly [(meth) acryloy
Roxyalkyl] (iso) cyanurate and other radicals
Obtained by mixing polymerizable monomers in a specific ratio
(JP-A-05-230397)
Gazette, JP-A-06-128502). This
Resin composition that can achieve both excellent wear resistance and weather resistance.
is suggesting. Incidentally, it is used as a material for automobiles.
The method of evaluating the abrasion resistance of the coating film is based on the conventional steel wool.
Using the evaluation result of rubbing scratch resistance by
Came. Evaluation method of wear resistance by this steel wool and
Contact the rolled steel wool on the sample surface and load
Reciprocate this while applying weight, and then use the damaged tool
Is determined by the light transmittance. But
However, in recent years, the evaluation as an index of this abrasion resistance (scratch resistance)
The method involves contacting an eraser-like ring on the sample surface.
Roll on concentric circles while applying a load to scratch
A Taber abrasion test to determine by the transmittance of afterglow
The evaluation method is being replaced by the Taber abrasion test.
Demands for improved wear resistance have increased. this is,
Taber wear is finer than steel wool
The same level in the evaluation of wear resistance with steel wool
Even if there are two different samples
In the evaluation of the wear resistance due to bar wear, its superiority can be confirmed
That's because. [0007] SUMMARY OF THE INVENTION The present invention relates to the above background.
It was made in the
Abrasion resistance on the surface, especially by Taber abrasion test
To form a cross-linked cured film with excellent weather resistance
To provide a coating composition. [0008] Means for Solving the Problems Accordingly, the present inventors have set forth the above
As a result of intensive studies to solve the problem, the (C)
Having a polyfunctional (meth) acryloyl group (a
So) a cyanurate compound as a main component, and (meth)
Polypentaerythritol having acryloyl group, la
Urethane poly (meth) having dical polymerizable unsaturated double bond
(T) an acrylate compound having a (meth) acryloyl group
Cyanurate, UV absorber, hindered amino acid
Terrestrial light stabilizer and photopolymerization initiator in specific proportions
Apply the combined coating composition to a synthetic resin
By curing by energy ray irradiation, Taber
Excellent synthesis with both abrasion resistance and weather resistance by abrasion test
The present inventors have found that a resin molded product can be obtained and completed the present invention. That is, the present invention provides (A) the following general formula:
A mono- or polypentaerythritol represented by (I)
At least one selected from poly (meth) acrylates
Of a monomer, 10 to 30 parts by weight, Embedded image (Wherein at least three of X are CH_Two= CR₁-CO
O-groups and the rest are -OH groups. N is 1 to 5
An integer, R₁Represents hydrogen or a methyl group. ) (B) at least two radically polymerizable unsaturated molecules per molecule
Urethane poly (meth) acrylate having sum double bond
At least one compound, 5 to 30 parts by weight, (C) general
Poly ((meth) acrylic compound represented by formula (II) or (III)
Loyloxyalkyl] (iso) cyanurate, 51-
70 parts by weight Embedded image Embedded image (Where Y is an acryloyl group, a methacryloyl group, a hydrogen atom
Represents an atom or an alkyl group, of which at least
Two are (meth) acryloyl groups and R_TwoIs 1 carbon
And oxyalkylene groups 4 to 4. ) (D) UV absorber, 2 to 30 parts by weight, (E) hinder
Deaminoether light stabilizer, 0.1 to 5 parts by weight (F)
Photopolymerization initiator, 0.1 to 10 parts by weight (only
And the total amount of (A), (B), (C), (D), (E), and (F)
Is 100 parts by weight). The coating composition is applied to the surface of a synthetic resin molded product.
To the film and irradiate it with active energy rays.
Abrasion resistance having a cross-linked cured film having a thickness of 1 to 30 μm, especially
Excellent Taber abrasion and weather resistance, heat resistance and chemical resistance
Synthetic resin molded products with excellent properties, durability and adhesion to the substrate
Obtainable. [0011] DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail.
First, each component of the coating composition of the present invention will be described. About the component (A) Component (A) of mono- or polypentaerythritol
Poly (meth) acrylate has high crosslink density
From this, the cured film containing this has a high hardness,
Also shows good polymerization activity by irradiation with active energy rays
You. As a specific example of the component (A), for example,
Nantaerythritol tri (meth) acrylate, penta
Erythritol tetra (meth) acrylate, dipenta
Erythritol tri (meth) acrylate, dipentae
Lisritol tetra (meth), acrylate dipentae
Lithritol penta (meth) acrylate, dipentae
Lisritol hexa (meth) acrylate, tripenta
Erythritol tetra (meth) acrylate, tripene
Taerythritol penta (meth) acrylate, tripe
Antaerythritol hexa (meth) acrylate, tri
Pentaerythritol hepta (meth) acrylate,
Lipetaerythritol octa (meth) acrylate, etc.
Is mentioned. The proportion of the component (A) used is (A) to (F)
10 to 30 parts by weight per 100 parts by weight of the total amount of the components, more preferably
Preferably, it is 15 to 25 parts by weight. (A) Component amount is 1
At less than 0 parts by weight, a cured film with sufficient abrasion resistance can be obtained.
If not obtained, the hardness of the cured film will be high if it exceeds 30 parts by weight.
Abrasion resistance in Taber abrasion test
Properties tend to decrease. When a large amount is blended
Cracks easily occur in the cured film,
Cracks will occur in the cured film after the weather resistance test,
Also, the heat resistance of the cured film tends to decrease. Regarding the component (B) Component (B), at least two radiographs per molecule
Urethane poly (meth) having polymerizable unsaturated double bond
Acrylate compounds provide toughness, flexibility,
A component that improves heat resistance and weather resistance.
(Meth) acrylate containing a hydroxyl group and two or more
An isocyanate compound having an isocyanate group on
Urethanization reaction product, and two or more
Polyol to isocyanate group-containing isocyanate,
By reacting polyester or polyamide diol
After synthesizing the adduct, the remaining isocyanate groups are
(Meth) acrylate containing droxyl group is added
Urethanation reaction products. The latter ureta
Poly (meth) acrylate is used to improve the toughness and
The flexibility is further improved, which is preferable. Also cured
In terms of improving the adhesion of the coating to the substrate, these
Has a molecular weight of preferably from 1,000 to 5,000. As a specific example of the polyisocyanate compound,
Is, for example, tolylene diisocyanate, ethylenediene
Socyanate, 1,2-diisocyanatopropane, 1,
3-diisocyanatopropane, 4,4'-diphenylme
Tandiisocyanate, xylylene diisocyanate,
Tetramethylxylylene diisocyanate, hexamethyl
Range isocyanate, lysine isocyanate, 4,
4'-methylenebis (cyclohexyl) isocyanate
G, methylcyclohexane-2,4-diisocyanate
G, methylcyclohexane-2,6-diisocyanate
G, 1,3-bis (isocyanatomethyl) cyclohexa
, Isophorone diisocyanate, trimethyl hexame
Tylene diisocyanate, tetramethylene diisocyanate
, Dimer acid diisocyanate, 2-isocyanate
Portions such as ethyl-2,6-diisocyanatohexanoate
Lisocyanate monomer and its burettes and birds
And further adducts thereof with various polyols.
Can be The polyol used for the synthesis of the adduct is particularly
Without limitation, specific examples include, for example, ethylene
Glycol, propylene glycol, butylene glycol
, Neopentyl glycol, trimethylolpropa
, Pentaeristol, sorbitol, mannitol
Alkyl and polyols such as
From ether polyols, polyhydric alcohols and polybasic acids
Synthetic polyester polyol, polycaprolact
And polyester polyols such as polyols.
You. (Meth) acryl containing a hydroxyl group
Specific examples of the rate include, for example, 2-hydroxyethyl
(Meth) acrylate, 2-hydroxypropyl (meth)
), Acrylate 2-hydroxybutyl (meth) ac
Relate, 4-hydroxybutyl (meth) acrylate
Butyl glycidyl ether, 2-ethylhexyl
Silglycidyl ether, glycidyl methacrylate, etc.
Reaction of Monoepoxy Compounds with (Meth) Acrylic Acid
Or polyethylene glycol or polypropylene glycol
Coal mono (meth) acrylate, polycapro
Lactone diol mono (meth) acrylate
Is mentioned. Polyisocyanate, various diols and hydride
Reaction with (meth) acrylate containing roxyl group
Is in the presence of a tin-based catalyst such as n-butyltin dilaurate,
Used so that isocyanate groups and hydroxyl groups are almost equal.
And heat at 60-70 ° C. for several hours. The reactants are generally
During the reaction or after the end of the reaction, because it often becomes highly viscous
Preferably diluted with organic solvents or other diluent monomers.
No. The proportion of the component (B) used is (A) to (F)
5 to 30 parts by weight per 100 parts by weight of the total amount of the components, more preferably
Or 10 to 20 parts by weight. (B) The amount of the component is fivefold
If it is less than 10 parts by weight, a cured film with sufficient toughness and weather resistance
Is not obtained, and the curability in an air atmosphere is deteriorated.
If it exceeds 30 parts by weight, the abrasion resistance in the Taber abrasion test
Wearability is reduced. Regarding the component (C) Component (C) represented by the general formula (II) or (III)
Poly [(meth) acryloyloxyalkyl] (a
S) Cyanurate cures without compromising high wear resistance
A component that can improve the toughness and heat resistance of the coating
is there. As a specific example of the component (C), for example,
(2-Acroyloxyethyl) iso, cyanurate
Lis (2-acryloyloxyethyl) isocyanurate
G, di (2-acroyloxypropyl) isocyanurate
, Tris (2-acryloyloxypropyl) iso
Cyanurate, di (2-acryloyloxyethyl) shea
Nurate, tris (2-acryloyloxyethyl)
Annulate, di (2-acroyloxypropyl) shea
Nurate, tris (2-acryloyloxypropyl)
Cyanurate and the like. The proportion of the component (C) used is (A) to (F)
51 to 70 parts by weight per 100 parts by weight of the total amount of the components, more preferably
More preferably, it is 51 to 60 parts by weight. (C) The amount of the component
If it is less than 51 parts by weight, sufficient resistance to the Taber abrasion test is required.
Hardened coating with toughness and heat resistance without impairing abrasion
When a film is not obtained and the amount exceeds 70 parts by weight, the curability decreases.
As a result, a sufficient cured film cannot be obtained
Poor adhesion and cracks in the coating. About the component (D) The ultraviolet absorber as the component (D) is not particularly limited, and the composition
If it is uniformly dissolved in the material and has good weather resistance
Can be used, but has good solubility in the composition and
Benzophenone-based and benzophenone-based
Zotriazole, phenyl salicylate, benzoic acid
Compounds derived from phenyl
UV absorbers having a length in the range of 240 to 380 nm are preferred.
More preferably, it can be contained in a large amount in the composition.
Benzophenone-based UV absorbers
It can prevent yellowing of substrates such as carbonate
Benzotriazole UV absorbers are preferred
New Therefore, it is best to use these two types in combination.
Is also preferred. As a specific example of the component (D), for example, 2
-Hydroxybenzophenone, 5-chloro-2-hydro
Xybenzophenone, 2,4-dihydroxybenzofe
Non, 2-hydroxy-4-methoxybenzophenone,
2-hydroxy-4-octyloxybenzophenone, 4
-Dodecyloxy-2-hydroxybenzophenone, 2-
Hydroxy-4-octadecyloxybenzophenone,
2,2'-dihydroxy-4-methoxybenzopheno
2,2'-dihydroxy-4,4'-dimethoxybenzene
Nzophenone, phenyl salicylate, p-tert-
Butylphenyl salicylate, p- (1,1,3,3-
Tetramethylbutyl) phenyl salicylate, 3-hydrido
Roxyphenyl benzoate, phenylene-1,3-di
Benzoate, 2- (2-hydroxy-5'-methylf
Enyl) benzotriazole, 2- (2-hydroxy-
5-tert-butylphenyl) -5-chlorobenzot
Riazol, 2- (2-hydroxy-3,5-di-te
rt-butylphenyl) benzotriazole, 2- (2
-Hydroxy-5-tert-butylphenyl) benzo
Triazole, 2- (2-hydroxy-4-octylph)
Enyl) benzotriazole, 2- (2 * -hydroxy
-5 * -methacryloxyethylphenyl) -2H-benzo
Triazole, 2- (2,4-dihydroxyphenyl)
-4,6-bis (2,4-dimethylphenyl) -1,
3,5-triazine and glycidylalkyl (C12-C
13) Reaction products with ether, etc.
Benzophenone 2-hydroxy-4-oct
Toxicbenzophenone and 2,4-dihydroxyben
Zophenone, benzotriazole-based 2- (2-hydro
(Xy-5-tert-butylphenyl) benzotriazo
Are particularly preferred, and these are used in combination of two or more.
It is more preferable to use. The proportion of the component (D) used is (A) to (F)
2 to 30 parts by weight per 100 parts by weight of the total amount of the components, more preferably
Or 5 to 15 parts by weight. (D) The amount of the component is 2 weight
Less than the part, from the weather resistance of the cured film and the ultraviolet light of the substrate
Protection is not sufficient, and if it exceeds 30 parts by weight,
Insufficient curing, toughness, heat resistance and abrasion resistance of the cured film
Wearability is reduced. About the component (E) (E) Component hindered amino ether light stabilizer
Examples include, for example, bis (2,2,6,6-tetramethyl
Ru-4-piperidyl) sebacate, bis (1,2,2,2)
6,6-pentamethyl-4-piperidyl) sebacate,
Bis (1-methoxy-2,2,6,6-tetramethyl-
4-piperidyl) sebacate, bis (1-ethoxy-
2,2,6,6-tetramethyl-4-piperidyl) seba
Kate, bis (1-propoxy-2,2,6,6-tet
Lamethyl-4-piperidyl) sebacate, bis (1-bu
Toxi-2,2,6,6-tetramethyl-4-piperidi
Le) sebacate, bis (1-pentyloxy-2,2,2)
6,6-tetramethyl-4-piperidyl) sebacate,
Bis (1-hexyloxy-2,2,6,6-tetramethyl
Ru-4-piperidyl) sebacate, bis (1-heptylo)
Xy-2,2,6,6-tetramethyl-4-piperidi
Le) sebacate, bis (1-octoxy-2,2,6,6)
6-tetramethyl-4-piperidyl) sebacate, bis
(1-nonyloxy-2,2,6,6-tetramethyl-4
-Piperidyl) sebacate, bis (1-decaniloxy)-
2,2,6,6-tetramethyl-4-piperidyl) seba
Kate, bis (1-dodecyloxy-2,2,6,6-te
Tramethyl-4-piperidyl) sebacate and the like.
Of these, bis (1-octoxy-2,2,2)
6,6-tetramethyl-4-piperidyl) sebacate
Particularly preferred. The proportion of the component (E) used is (A) to (F)
0.1 to 5 parts by weight per 100 parts by weight of the total amount of the components, more preferably
Preferably, it is 0.5 to 2 parts by weight. (E) The amount of the component
If the amount is less than 0.1 part by weight, the weather resistance and durability of the cured film may be poor.
Insufficiently, if more than 5 parts by weight, the coating itself will be insufficiently cured.
And the toughness, heat resistance, and abrasion resistance of the cured film decrease.
I do. About the component (F) As the photopolymerization initiator as the component (F), benzoin,
Benzoin monomethyl ether, benzoin isopropyl
Ruether, acetoin, benzyl, benzophenone,
p-methoxybenzophenone, diethoxyacetopheno
, Benzyldimethyl ketal, 2,2-diethoxy
Cetophenone, 1-hydroxycyclohexylphenyl
Ketone, methylphenylglyoxylate, ethylphen
Nylglyoxylate, 2-hydroxy-2-methyl-
Carbonyl compounds such as 1-phenylpropan-1-one
Substance, tetramethylthiuram monosulfide, tetramethyl
Sulfur compounds such as rutiuram disulfide, 2,4,6
-Trimethylbenzoyldiphenylphosphine oxa
Acylphosphine oxides such as
Can be. These are used in one or two or more mixed systems
Is done. Among these, benzophenone, benzoin
Isopropyl ether, methylphenylglyoxylate
G, benzyldimethyl ketal is more preferred. The proportion of the component (F) used is (A) to (F)
0.1 to 10 parts by weight in 100 parts by weight of the total amount of the components, and more
Preferably it is 1 to 5 parts by weight. When the amount of the component (F) is 0.
If it is less than 1 part by weight, the curability becomes insufficient and 10 parts by weight
Exceeding the above causes coloring of the cured film and also reduces weather resistance.
You. The coating composition of the present invention comprises the above (A)
(B), (C), (D), (E) and (F) each component
Organic solvents, antioxidants, yellowing
Inhibitor, bluing agent, pigment, leveling agent, defoaming
Agents, thickeners, antisettling agents, antistatic agents, antifogging agents, etc.
May be included. Organic solvent depends on the type of substrate
It is better to select and use according to the kind. For example, as a substrate
Synthetic tree of acrylic board, vinyl chloride, polycarbonate, etc.
When using fats, alcohols such as isobutanol
Solvent, n-butyl acetate, diethylene glycol acetate
Ester solvents such as ethylcellosolve, etc.
It is preferable to use a combination of three types of lube solvents. solvent
Is used in an amount of 20 to 8 with respect to 100 parts by weight of the coating composition.
It is preferable to use 00 parts by weight. In applying the coating composition of the present invention to a substrate,
Is brush coating, spray coating, dip coating, spin coating
Coating, curtain coating, etc. are used,
Coating workability of coating material composition, coating smoothness, uniformity, hardness
From the viewpoint of improving the adhesion of
It is preferable to apply by adding a solvent. The coating composition of the present invention was applied to a substrate.
By the subsequent irradiation of active energy rays, it crosslinks and forms a cured film.
Form. When curing by active energy ray irradiation
Is a coating material composition having a film thickness of 1 to 50 μm on a substrate, preferably
Or a high pressure mercury run
100 to 400 using a metal halide lamp, etc.
1000 nm to 5000 mJ / cm^TwoBecomes
Irradiation as follows. The atmosphere for irradiation may be air,
It may be in an inert gas such as nitrogen or argon. The coating composition of the present invention can be used for various base materials.
It can be used to modify the surface of synthetic resin molded products.
The molded fat product is not particularly limited, but
In addition, there have been requests for improvements in wear resistance, weather resistance, etc.
There are various kinds of thermoplastic resins and thermosetting resins. concrete
For example, polymethyl methacrylic resin, polycarbonate
Nate resin, polyester resin, poly (polyester)
Carbonate resin, polystyrene resin, ABS resin, A
S resin, polyamide resin, polyarylate resin, polymer
Tacrylimide resin, polyallyl diglycol carbonate
And the like. In particular, polymethylmethacrylate
Resin, polycarbonate resin, polystyrene resin,
Limethacrylimide resin has excellent transparency and abrasion resistance
Since the demand for improvement is strong, the coating composition of the present invention is applied.
Is particularly effective. Also, synthetic resin molded articles are those resins
Sheet-like molded products, film-shaped molded products,
Shapes and the like. [0036] The present invention will be further described with reference to the following Examples and Comparative Examples.
explain in detail. The measurement evaluation in the examples is as follows
Made by the way. (1) Appearance of cured film The appearance after application and curing of the composition was visually evaluated. The surface is flat
○: smooth and transparent
Is indicated by も の, and whitening or clouding is observed by ×.
Was. (2) Wear resistance Wear wheel CS-10,500 using Taber abrasion tester
After 300 rotation wear under a g load, the diffuse transmittance (haze
Value) was measured to determine the wear resistance. This abrasion resistance
The criterion of the haze value before wear measured beforehand
Depending on the increase haze value, it becomes ◎, ○, △, and × as follows
Classified. …: Increase haze value = 0 to 10 …: Increase haze value = 10 to 15 Δ: Increase haze value = 16 to 20 ×: Increase haze value = 20 or more (3) Adhesion Cross cut to reach the substrate at 1mm intervals on the cured coating
Put 1mm^TwoMake 100 cross-cuts and put a cello on it
Paste the tape and peel off sharply.
I counted. When there is no peeling, the number of peeling is 1
The thing of 50 pieces is set to △, and the number of peeling is 51 to 100 pieces.
Is indicated by x. (4) Heat resistance The coated plate sample was placed in a hot air dryer at 120 ° C. for 24 hours,
The appearance change of the cured film was visually observed. no change
も の indicates a small thing and 発 生 indicates a small crack
Then, those in which cracks occurred on the entire surface of the coated plate were evaluated as x. (5) Weather resistance As a weather tester, Sunshine Carbon Weatherome
(Suga Test Machine, WEL-SUN-HC-B type)
Use, black panel temperature 63 ± 3 ℃, rainfall 12 minutes,
The weather resistance test was performed with a cycle of irradiation for 48 minutes. And
Of the cured film after exposure for 2000 hours and after exposure for 2500 hours
The change was observed and the adhesion was tested. (A) Regarding the discoloration of the external appearance, those without discoloration were marked with a circle.
Then, those with slight yellowing were marked as △, and yellowing was large
Those were marked as x. (B) Regarding generation of cracks and peeling of the cured film,
Those that did not exist were marked with ○, and those that did exist were marked with x. Examples 1 to 5 and Comparative Examples 1 to 5 The coating material composition was adjusted at the compounding ratios shown in Tables 1 and 2, and the thickness was adjusted.
3mm polycarbonate resin plate (manufactured by GE, product
Name: Lexan LS-II), and the cured film became 8 μm thick.
Spray painted as follows. Volatile organic solvent by heating
After emitting, a high-pressure mercury lamp was used in the air at a wavelength of 34
The integrated light amount from 0 nm to 380 nm is 3000 mJ / cm^Two
Was irradiated to obtain a cured coating film. The resulting coating
Are shown in Tables 1 and 2. Example 6, Comparative Example 6 The coating material composition was adjusted at the compounding ratios shown in Tables 1 and 2, and the thickness was adjusted.
3mm polymethyl methacrylate resin plate (Mitsubishi Rei
Yon Co., trade name: Acrypet VH)
Spray coating was performed so that the film became 8 μm. By heating
After evaporating the organic solvent, a high-pressure mercury lamp
Used, and the integrated light amount of wavelength 340 nm to 380 nm is 300
0mJ / cm^TwoEnergy to obtain a cured coating
Was. The evaluation results of the obtained coating film are shown in Tables 1 and 2. Example 7, Comparative Example 7 The coating material composition was adjusted at the compounding ratios shown in Tables 1 and 2, and the thickness was adjusted.
After curing on a 3 mm thick polymethacrylimide resin plate
Spray coating was performed so that the film became 8 μm. By heating
After evaporating the organic solvent, a high-pressure mercury lamp
Used, and the integrated light amount of wavelength 340 nm to 380 nm is 300
0mJ / cm^TwoEnergy to obtain a cured coating
Was. The evaluation results of the obtained coating film are shown in Tables 1 and 2. [0045] [Table 1][0046] [Table 2]The symbols of the compounds in Tables 1 and 2 are as follows:
It is on the street. DPHA: Dipentaerythritol hexaacrelay
G UA1: dicyclohexylmethane diisocyanate
2 mol, 1 mol of nonabutylene glycol and 2-h
Molecule synthesized from 2 mol of droxyethyl acrylate
2500 urethane acrylate TAIC: tris (2-acryloyloxyethyl)
Isocyanurate HBPB: 2- (2-hydroxy-5-tert-butyl)
Tylphenyl) benzotriazole BOTS: bis (1-octoxy-2,2,6,6-
Tetramethyl-4-piperidyl) sebacate BNP: Benzophenone MPG: methylphenylglyoxylate [0048] The coating composition of the present invention can
Apply to active materials and irradiate with active energy such as general ultraviolet rays
By cross-linking without degrading the substrate,
Excellent abrasion resistance, especially in the Taber abrasion test
And excellent in weather resistance, heat resistance, durability and chemical resistance
A synthetic resin molded article having a cured film can be obtained.

   ────────────────────────────────────────────────── ─── Continuation of front page    F term (reference) 4J038 FA011 FA282 KA04 NA19                 4J100 AL08Q AL09P AL67P AL67R                       BA02P BA03P BA03Q BA04R                       BA08P BA11R BA42Q BC73R                       CA05 CA31 FA03 HA53 HC25                       HC33 HC63 HC69 HC75 JA01

Claims (1)

Claims: (A) at least one monomer selected from poly (meth) acrylates of mono- or polypentaerythritol represented by the following general formula (I), 10 to 30:
Parts by weight, (Wherein at least three of X are CH ₂ = CR ₁ -CO
O-groups and the rest are -OH groups. N is an integer of 1 to 5, and R ₁ represents hydrogen or a methyl group. (B) at least one urethane poly (meth) acrylate compound having at least two radically polymerizable unsaturated double bonds in one molecule, 5 to 30 parts by weight, (C) a general formula (II) or (III) )) [Poly ((meth) acryloyloxyalkyl] (iso) cyanurate, 51-
70 parts by weight Embedded image (Wherein, Y represents an acryloyl group, a methacryloyl group, a hydrogen atom or an alkyl group, at least two of which are (meth) acryloyl groups, and R ₂ has 1 carbon atom)
And oxyalkylene groups 4 to 4. (D) UV absorber, 2 to 30 parts by weight, (E) hindered amino ether light stabilizer, 0.1 to 5 parts by weight (F)
Photoinitiator, 0.1 to 10 parts by weight (provided that the total amount of (A), (B), (C), (D), (E), and (F) is 100 parts by weight A coating material composition characterized in that: