JPH0144735B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is a thermosetting plastic molded product made of diethylene glycol bisallyl carbonate or a copolymer thereof, which is coated with an ultraviolet curable coating that has excellent adhesion to the base material and has excellent surface smoothness and surface appearance. This invention relates to a method for manufacturing curable plastic molded articles. Polydiethylene glycol bisallyl carbonate resin (also known as polyallyl diglycol carbonate resin, hereinafter abbreviated as PDAC resin), which is a type of thermosetting plastic, has excellent transparency, abrasion resistance, and impact resistance. Therefore, in recent years, they have been used in large quantities especially in the field of eyeglasses such as prescription lenses, fashion lenses, and sunglasses, or in the field of optics. However, although the abrasion resistance of PDAC resin is excellent among transparent thermosetting plastics, its abrasion resistance is still not sufficient when compared to inorganic glass. Therefore, in recent years, attempts have been made to coat spectacle lenses or optical lenses made from PDAC resin with a coating material that has better wear resistance and surface hardness, but the quality is not sufficient. I couldn't say it. The present invention thus provides a lens surface made of PDAC resin, which is widely used in the eyeglass lens field or optical lens field, which has excellent adhesion to the base material, and has excellent abrasion resistance and scratch resistance with excellent surface smoothness and surface appearance. This relates to the manufacturing method of lenses. Various methods have been studied as surface pretreatment methods for thermoplastic plastics to improve the adhesion between the base material and coating material.For example, chemical treatment methods include organic solvent treatment, amine treatment, and silane cupping. Ring agent treatment, acid treatment, etc., and physical treatment methods include plasma treatment, sputter etching treatment,
Ultraviolet irradiation treatment, corona discharge treatment, surface polishing treatment, etc. are known, but thermosetting resins, especially PDAC
Not much is known about resin pretreatment methods. In view of this situation, the present inventors conducted intensive studies on a method for firmly adhering an ultraviolet curable coating to a thermosetting plastic molded product made of diethylene glycol bisallyl carbonate or its copolymer, and found that After treating a plastic molded article with a solution containing an alkali metal hydroxide, coating it with an ultraviolet curable coating composition and curing the coating film with ultraviolet rays will improve the adhesion of the coating to the substrate. The present invention was completed after discovering that excellent plastic molded products can be obtained. That is, the gist of the present invention is to treat the surface of a thermosetting plastic molded article made of diethylene glycol bisallyl carbonate or its copolymer with a solution containing an alkali metal hydroxide, and then apply an ultraviolet curable coating. By painting a material composition and curing it with ultraviolet light, we manufacture plastic molded products with a hardened surface coating that has excellent adhesion to the base material, as well as abrasion resistance with excellent surface smoothness and surface appearance. The goal is to provide a way to do so. The coating material composition used in the present invention includes (A) one or more compounds (a) having three or more (meth)acryloyloxy groups in one molecule;
99.90 parts by weight, 0 to 49.95 parts by weight of one or more compounds (b) having 2 or less polymerizable unsaturated groups in one molecule, and 1
0.05 to 25 parts by weight of one or more compounds having a (meth)acrylamide group and a hydroxyl group in the molecule, and one or more organic acids (c) substituted with fluorine, chlorine, or bromine that are liquid at room temperature and pressure. 0.05 to 25 parts by weight (total 100 parts by weight), and (B) 0.01 to 25 parts by weight of a photosensitizer per 100 parts by weight of the mixture.
Preferably, the coating composition comprises 10 parts by weight. Among these UV-curable compositions, specific examples of compounds (a) having three or more (meth)acryloyloxy groups in one molecule include trimethylolpropane tri(meth)acrylate, trimethylolethane tri( meth)acrylate, pentaglycerol tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, glycerin tri(meth)acrylate; or the following general formula (In the formula, at least three R are CH ₂ = CH−COO
- group, and the rest are -H or -OH groups.
n ₁ , n ₂ , n ₃ , n ₄ , m ₁ , m ₂ , m ₃ , and m ₄ each takes a numerical value of 0, 1, or 2, and x is a positive integer from 1 to 10. ), such as malonic acid/trimethylolethane/acrylic acid, malonic acid/trimethylolpropane/acrylic acid, malonic acid/glycerin/acrylic acid, malonic acid/pentaerythritol/acrylic acid, succinic acid/trimethylolethane /Acrylic acid, succinic acid/Trimethylolpropane/Acrylic acid, succinic acid/
Glycerin/acrylic acid, succinic acid/pentaerythritol/acrylic acid, adipic acid/trimethylolethane/acrylic acid, adipic acid/trimethylolpropane/acrylic acid, adipic acid/pentaerythritol/acrylic acid, adipic acid/
Glycerin/acrylic acid, glutaric acid/trimethylolethane/acrylic acid, glutaric acid/trimethylolpropane/acrylic acid, glutaric acid/glycerin/acrylic acid, glutaric acid/pentaerythritol/acrylic acid, sebacic acid/trimethylolethane/acrylic Acid, esterification reaction product by combination of compounds such as sebacic acid/trimethylolpropane/acrylic acid, sebacic acid/glycerin/acrylic acid, sebacic acid/pentaerythritol/acrylic acid (in actual reaction, the general formula () (The amount of raw materials can be changed stoichiometrically as necessary within the range that satisfies the following);
Or the following general formula (In formula, X ₁₁ , X ₁₂ , X ₁₃ , X ₂₂ , X ₂₃ ...Xn ₂ , Xn ₃ ,
At least three of _X14 are _CH2 =CH-COO- groups, and the rest are -OH groups. n is an integer from 2 to 5. ), such as dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol tetra(meth)acrylate Examples include acrylate, tripentaerythritol penta(meth)acrylate, tripentaerythritol hexa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, and the like. These can be used in combination of one or more types. Among these compounds having three or more (meth)acryloyloxy groups in one molecule, compounds having an acryloyloxy group represented by the general formula () do not require an inert gas and are resistant to ultraviolet rays in normal air. This is more preferable because it cures sufficiently. These compounds (a) include the compound (a), a compound (b) having two or less polymerizable unsaturated groups in one molecule, and an organic acid (c) substituted with fluorine, chlorine, or bromine. (hereinafter simply referred to as mixture (A)) 100
It is preferably used in a range of 25 to 99.90 parts by weight, more preferably 40 to 99.8 parts by weight. If the proportion of the compound (a) having three or more (meth)acryloyloxy groups in one molecule is less than 25 parts by weight, the resulting coating will have poor abrasion resistance and surface hardness, so it is not preferable. . As the compound (b) having two or less polymer unsaturated groups in one molecule, any ordinary monomer having radical polymerization activity can be used, but
A compound having a (meth)acryloyloxy group as the polymerizable unsaturated group is preferable because it has excellent polymerization activity by ultraviolet rays. Specific examples of these compounds include two (meta) molecules in one molecule.
Compounds having an acryloyloxy group include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate,
Polyethylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, propylene glycol di(meth)acrylate, di Propylene glycol di(meth)
Acrylate; or the following general formula (In the formula, R ₁ is hydrogen or a methyl group, X ₁ , X ₂ ...,
Xn is the same or different alkylene group having 6 or less carbon atoms or has a structure in which one hydrogen atom thereof is replaced with a hydroxyl group, and n is an integer of 0 to 5. ), for example, 2,2-bis-(4acryloxyphenyl)propane, 2,2-bis-(4
Methacryloxyphenyl-)propane, 2,2-bis-(4-acryloxyethoxyphenyl-)propane, 2,2-bis-(4methacryloxyethoxyphenyl-)propane, 2,2-bis-(4-methacryloxyphenyl-)propane Acryloxydiethoxyphenyl-)propane, 2,2-bis-(4methacryloxydiethoxyphenyl-)propane, 2,2-bis-(4acryloxypropoxyphenyl-)propane, 2,2-bis-(4methacryloxydiethoxyphenyl-)propane -(4methacryloxypropoxyphenyl-)propane, 2,2-bis-[4acryloxy(2hydroxypropoxy)
Phenyl-]propane, 2,2-bis[-4methacryloxy(2hydroxypropoxy)phenyl-]propane, 2,2-bis-[4acryloxy(2hydroxypropoxyethoxy)phenyl-]propane, 2,2-bis- Examples include [4methacryloxy(2hydroxypropoxyethoxy)phenyl]propane, etc., but compounds having a (meth)acryloyloxy group represented by the general formula () have excellent polymerization activity by ultraviolet rays in normal air. It is more preferable because Examples of compounds having one (meth)acryloyl group in one molecule include methyl (meth)acrylate, propyl (meth)acrylate, butyl acrylate, isobutyl acrylate, t-butyl acrylate, 2-ethylhexyl acrylate, lauryl acrylate, Tridecyl acrylate, cyclohexyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, glycidyl acrylate, tetrahydrofurfuryl acrylate, benzyl acrylate, 1,4-butylene glycol monoacrylate, ethoxyethyl acrylate, ethyl carbitol acrylate, 2- Hydroxy-
3-chloropropyl acrylate, acrylamide, N-hydroxymethyl (meth)acrylamide, N-hydroxyethyl (meth)acrylamide, N-hydroxypropyl (meth)acrylamide, N-hydroxybutyl (meth)acrylamide, hydroxymethyldiacetone acrylamide, N-hydroxyethyl-N-(methyl)acrylamide and the like can be mentioned. Among these, compounds such as 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, glycidyl acrylate, tetrahydrofurfuryl acrylate, ethoxyethyl acrylate, ethyl carbitol acrylate, butoxyethyl acrylate, 1,4-butylene glycol monoacrylate, etc. Acrylates having a hydroxyl group and/or a cyclic ether bond and/or a chain ether bond in the side chain are particularly preferred since they have excellent polymerization activity by ultraviolet rays in normal atmosphere. Furthermore, N-hydroxymethyl acrylamide, N-hydroxyethylacrylamide, N-
Compounds having a hydroxyl group and an acrylamide group, such as hydroxypropylacrylamide and hydroxymethyldiacetone acrylamide, can be used in conjunction with an organic acid substituted with fluorine, chlorine, or bromine, as described below, to form a cured film and base material. It is particularly desirable for increasing the adhesion of the cured film, since it provides very good adhesion to the resin molded product. These compounds having a (meth)acrylamide group and a hydroxyl group are used in an amount of 0.05 to 25 parts by weight, but most preferably, among compounds having two or less (meth)acryloyl groups, a (meth)acrylamide group and a hydroxyl group are used. Compounds with 0.1-15
Parts by weight. Examples of organic acids (c) substituted with fluorine, chlorine or bromine include difluoroacetic acid, trifluoroacetic acid, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, monobromoacetic acid, tribromoacetic acid, dichloropropionic acid, tetrachloropropionic acid, etc. However, monochloroacetic acid, dichloroacetic acid and trichloroacetic acid are most preferred from the viewpoint of handling and other effects. These organic acids (c) in 100 parts by weight of mixture (A)
It is preferable to use it in the range of 0.05 to 25 parts by weight, and although the details of the reaction mechanism are not fully elucidated,
By using it in combination with the monomer mixture (A), it is possible to obtain an extremely excellent adhesion to a thermosetting plastic made of diethylene glycol bisallyl carbonate or a copolymer thereof. The preferred range of use of these organic acids (c) is 0.1 to
In the range of 20 parts by weight. If the proportion used is less than 0.05 parts by weight, the effect of improving adhesion by the specific organic acid is small, and if it exceeds 25 parts by weight, the coating may whiten due to the residual organic acid. Examples of photosensitizers that promote curing by ultraviolet rays include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, acetoin, butyroin, toluoin, benzyl, benzophenone, p-methoxybenzophenone, diethoxyacetophenone. , α,α-dimethoxy-α-phenylacetophenone, methyl phenyl glyoxylate, ethyl phenyl glyoxylate, 4,4′-bis(dimethylaminobenzophenone), 2-hydroxy-2-methyl - Carbonyl compounds such as 1-phenylpropan-1-one, sulfur compounds such as tetramethylthiuram monosulfide and tetramethylthiuram disulfide, azobisisobutyronitrile, azobis-2,4-dimethylvaleronitrile azo compounds such as benzoyl peroxide,
Examples include peroxide compounds such as ditertiary butyl peroxide. These compounds may be used alone or in combination of one or more. The amount of these photosensitizers to be added to 100 parts by weight of mixture (A) is preferably 0.01 to 10.0 parts by weight; adding too much of these may discolor the crosslinked cured film or cause a decrease in weather resistance. do. Furthermore, if the amount added is too small, the curability of the coating material with ultraviolet rays will deteriorate. Methods such as brush coating, flow coating, spray coating, spin coating, or dip coating are used to apply the above-mentioned coating composition, but the coating workability of the coating composition and the smoothness and uniformity of the film are important. From this point of view, it is preferable to use a suitable organic solvent in combination, and it is necessary to apply the coating amount to the molded product so that the thickness of the obtained cured film is in the range of 1 to 30 μm. If the film thickness is less than 1 μm, the surface hardness and abrasion resistance of the obtained cured film will not be sufficient, while if the film thickness exceeds 30 μm, cracks will easily appear in the cured film. As a means of curing the coating material composition, 1500 Å ~
It is essential to irradiate ultraviolet light of 8000Å,
By using other curing means, it is not possible to achieve the excellent adhesion with the thermosetting plastic substrate, which is one of the aspects of the present invention. As the ultraviolet rays, high-energy ultraviolet rays emitted from medium-pressure mercury lamps, high-pressure mercury lamps, or ultra-high-pressure mercury lamps are more preferable. Alkali metal hydroxides are listed in the Periodic Table of Elements Ia
Among these, sodium hydroxide and potassium hydroxide are particularly preferred from the viewpoint of handling and effectiveness, and these may be used alone or in combination. The thermosetting plastic molded article treated with a solution containing these alkali metal hydroxides and the UV-curable coating composition provide strong adhesion to the substrate as described in the examples. Although it has not yet been determined in detail whether it can be obtained, it is a type of thermosetting plastic.
In the case of PDAC resin, it is recognized that some of the base material is hydrolyzed by aqueous solution treatment with alkali metal hydroxide, and the interaction between this and strong UV energy irradiation causes UV curing. It is expected that strong adhesion occurred between the adhesive coating composition and the base resin. Water is most preferred as the solvent for the alkali metal hydroxide solution, but if necessary, an organic solvent that can be mixed with water may be used in combination. In the case of PDAC resin lenses, it is preferable to process them in a solution made of these solvents using the immersion method, as sufficient optical properties cannot be obtained with other methods, and white spots, distortions, and Dragging, gear marks, etc. may appear. The concentration of the aqueous alkali metal hydroxide solution during the dipping treatment is preferably in the range of 1 to 30% by weight. If it is less than 1% by weight, long-term processing is required to improve adhesion, resulting in poor workability.Conversely, even if the concentration is high, the effect will not be particularly high, but rather the adhesion improvement effect will be 1 to 30% by weight. It is recognized that there are cases where the condition becomes worse than when the condition is within the range of . The temperature of the aqueous solution of alkali metal hydroxide is
A temperature in the range of 50 to 90°C is suitable; if it is less than 50°C, the effect of improving adhesion will not be sufficient, and if it exceeds 90°C, it will be difficult to control the processing conditions and workability will deteriorate. Furthermore, in the case of dyed lenses made of PDAC resin, decolorization becomes noticeable and the product value decreases. The appropriate time for treating lenses made of PDAC resin is in the range of 5 to 120 seconds; if it is less than 5 seconds, the effect of improving adhesion will be poor, and if it exceeds 120 seconds, the effect will be particularly high. do not have. Rather, in the case of dyed lenses, the decolorization of the dye becomes noticeable, which is not preferable. In order to take advantage of the high-speed curing method called ultraviolet curing method and seek economic efficiency, it is necessary to keep the treatment temperature of alkali metal hydroxide as high as possible and shorten the treatment time. This is essential in order to obtain strong adhesion. Furthermore, when treating a PDAC resin lens in an Al-Ali metal hydroxide solution using the immersion method, the lowering and lifting speeds during immersion of the lens should be adjusted to a smooth 3.
In order to maintain the smoothness and appearance of the lens surface, it is essential to maintain the speed of the alkali metal hydroxide solution adhering to the pulled lens at a speed of cm/second or higher and to prevent the solution from drying out before washing it with water. Manufacturing conditions make it impossible. In other words, if the pull-down and pull-up speed during lens immersion is less than 3 cm/sec, the PDAC is likely to be affected by turbulence in the liquid level when immersed in an alkali metal hydroxide solution.
This is because the resin lens surface is disturbed and surface defects such as waves and unevenness occur, resulting in a decrease in the smoothness and surface appearance of the lens surface. The reason for washing the alkali metal hydroxide solution adhering to the lens with water as soon as possible before drying is that once dried, the alkali metal hydroxide and other adhesion cannot be completely washed away with water using normal washing methods, and the coating material This is because the appearance and smoothness of the PDAC resin lens after applying the composition deteriorates, and the optical properties as a lens are lost. The allowable time for washing PDAC resin lenses after alkali metal hydroxide treatment is preferably 30 seconds or less, and if the time for leaving them for washing exceeds 30 seconds, the lenses may not appear to have air-dried. However, the microsolution dries, often resulting in defects such as white spots and spots on the lens. By satisfying the above processing conditions,
PDAC resin lenses are manufactured industrially as lenses that are easy to work with, economical, and have excellent optical properties.If these conditions are not met, use PDAC resin lenses that have excellent optical properties and adhesion. Plastic lenses cannot be manufactured economically. The thermosetting resin molded product having an ultraviolet curable coating on the surface produced by the present invention has excellent adhesion to the base material, has an excellent surface appearance, and has excellent durability of the molded product. It has excellent abrasion and scratch resistance, and can be used for organic window glass, lighting equipment covers, reflectors,
It is extremely useful for applications such as mirrors, glasses, sunglasses, and optical lenses. In particular, when optical lenses or eyeglass lenses made of PDAC resin are manufactured using this manufacturing method, they have excellent optical properties and excellent adhesion to the base material, so the film does not peel off even under harsh conditions and environments. , it becomes possible to obtain industrially inexpensive lenses with excellent abrasion resistance and scratch resistance that do not cause cracks or the like. The content of the present invention will be explained in more detail with reference to Examples below, in which parts represent parts by weight. In addition, the measurement evaluation in the example was performed by the following method. (1) Scratch resistance Scratch test with #000 steel wool. 〇... Even if you rub it lightly, there will be almost no scratches on its surface. △...If you rub it lightly, the surface will be slightly scratched. ×... Even if rubbed lightly, the surface will be seriously scratched (same level as the base resin). (2) Adhesion Thermal cycle test: The sample is immersed in warm water at 65°C for 1 hour, then immediately immersed in ice water for 10 minutes, and then dried at 80°C for 1 hour. This is 5
Repeat times. After performing the above thermal cycle test, a cross-cut cellophane tape peeling test is performed. In other words, cut 11 film cutting lines that reach the base material at 1 mm intervals in the film, making 100 lines of 1 mm ² each, vertically and horizontally, and then tape cellophane tape (manufactured by Sekisui Chemical Co., Ltd.) on top. Paste and peel off quickly. Repeat this operation with the cellophane tape on the same area, and then use a 30x magnifying glass to observe the marks after performing the peel test to see if there are any chips. 〇...Even after performing a peel test on the same spot 10 times, no peeling marks or cracks were observed. ×... After repeating the process 10 times on the same spot, peeling or chipping was observed. (3) Optical properties Place your eyes 50cm vertically in front of a black screen.
Visually observe a sample transparent object placed between the eyes and the screen using a fluorescent lamp placed 25 cm above the eye level above the screen. 〇…No optical defects such as white spots, distortions, sag, gear marks, etc. are observed. Δ... Some optical defects are observed. ×...Optical defects are clearly observed. Example 1 A clear lens made of PDAC resin was immersed in a 5% by weight potassium hydroxide aqueous solution at 70°C at a speed of 5cm/
sec for 90 seconds. Wash this immediately with water,
After draining, add 10 parts of dipentaerythritol pentaacrylate, 10 parts of dipentaerythritol hexaacrylate, 5 parts of tetrahydrofurfuryl acrylate, and 4 parts of 2,2-bis-(4-acryloxydiethoxyphenyl-)propane. , N-
1 part methylol acrylamide, 60% ethanol
1 part of toluene, 1 part of dichloroacetic acid, 0.5 part of benzoin ethyl ether, 0.5 part of p-chlorobenzophenone, and 0.1 part of silicone repelling agent by dipping at a speed of 0.2 cm/sec. A film was formed and irradiated for 10 seconds at a distance of 250 mm using a 5KW high-pressure mercury lamp in air. The scratch resistance, adhesion and optical properties of the obtained lens are shown below.

[Table] Example 2 Prescription clear lenses manufactured by PDAC were immersed in a 20% by weight sodium hydroxide aqueous solution at 85°C at a speed of 6.
After processing at a speed of cm/sec for 30 seconds, it was immediately washed with water and drained. This lens was mixed with 5 parts of dipentaerythritol hexaacrylate, 5 parts of dipentaerythritol pentaacrylate, 5 parts of dipentaerythritol tetraacrylate, 6 parts of tetrahydrofurfuryl acrylate, 2 parts of an ester consisting of adipic acid/trimethylolpropane/acrylic acid, and N −
In a coating composition consisting of 2 parts of methylol acrylamide, 50 parts of isopropyl alcohol, 10 parts of isobutyl alcohol, 10 parts of hexane, 5 parts of dichloroacetic acid, 0.5 part of benzoin methyl ether, 1.0 part of benzophenone, and 0.1 part of a silicone leveling agent.
Dip coating was carried out at a speed of 0.3 cm/sec. this
Irradiation was performed in the air for 15 seconds using a 2KW high-pressure mercury lamp at an irradiation distance of 200mm. The results obtained are shown below.

[Table] Examples 3 to 6, Comparative Examples 1 to 5 Plano-dyed lenses made of PDAC resin were pretreated as shown in Table 1, and after draining, 8 parts of dipentaerythritol hexaacrylate and 8 parts of dipentaerythritol penta 5 parts of acrylate, 5 parts of dipentaerythritol tetraacrylate, 6 parts of tetrahydrofurfuryl acrylate, 1 part of N-methylolacrylamide, 50 parts of isopropyl alcohol, 15 parts of isobutanol, 9 parts of amyl acetate
0.3 parts of dichloroacetic acid, 0.3 parts of benzoin isopropyl ether, 0.7 parts of benzophenone, and 0.2 parts of silicone leveling agent.
Coating is carried out at a dipping speed of cm/sec, and this is applied at a rate of 2KW.
Irradiation was performed for 13 seconds in an air atmosphere using a high-pressure mercury lamp at an irradiation distance of 200 mm. The results obtained are shown in Table 1.

【table】

Claims (1)

[Scope of Claims] 1. The surface of a thermosetting plastic molded article made of diethylene glycol bisallyl carbonate or its copolymer is coated with a solution containing an alkali metal hydroxide at a concentration of 1 to 30% at a temperature of 50 to 90°C. 5 in solution
A method for producing a thermosetting plastic molded article having an ultraviolet curable cured coating on its surface, which comprises applying the following coating material composition which can be cured by ultraviolet rays after treatment for ~120 seconds, and curing it by ultraviolet rays. <Coating material composition> (A) One or more compounds (a) having three or more (meth)acryloyloxy groups in one molecule 25~
99.90 parts by weight, 0 to 49.95 parts by weight of one or more compounds (b) having two or less polymerizable unsaturated groups in one molecule, and one or more compounds having (meth)acrylamide groups and hydroxyl groups in one molecule. A mixture consisting of 0.05 to 25 parts by weight of one or more types, and 0.05 to 25 parts by weight of one or more organic acids (c) substituted with fluorine, chlorine, or bromine that are liquid at normal temperature and pressure (100 parts by weight in total) ), and (B) 0.01 to 0.01 parts by weight of photosensitizer per 100 parts by weight of the mixture.
A coating composition comprising 10 parts by weight. 2. A thermosetting plastic molding having an ultraviolet curable cured film on its surface as set forth in claim 1, wherein the alkali metal hydroxide solution is an aqueous solution of sodium hydroxide and/or potassium hydroxide. Product manufacturing method. 3. The compound according to claim 1, wherein the compound having two or less polymerizable unsaturated groups in one molecule has a (meth)acryloyloxy group as a polymerizable unsaturated group. A method for manufacturing thermosetting plastic molded products that have an ultraviolet curable coating on the surface. 4 A compound having a (meth)acrylamide group and a hydroxyl group in one molecule is N-(hydroxymethyl)
The ultraviolet curable cured coating according to claim 1, which is selected from acrylamide, N-(hydroxyethyl)acrylamide, N-(hydroxypropyl)acrylamide, and hydroxymethyldiacetone acrylamide. A method for producing a thermosetting plastic molded product having on the surface. 5. The ultraviolet curable cured film according to claim 1, wherein the organic acid substituted with fluorine, chlorine, or bromine is selected from monochloroacetic acid, dichloroacetic acid, and trichloroacetic acid. A method for producing a thermosetting plastic molded product having on the surface. 6. The method according to claim 1 or 2, wherein the treatment with an alkali metal hydroxide solution is an immersion method, and the lowering and pulling speed during immersion is 3 cm/sec or more. A method for manufacturing thermosetting plastic molded products that have an ultraviolet curable coating on the surface. 7. A thermosetting plastic molded article made of diethylene glycol bisallyl carbonate or its copolymer treated with an alkali metal hydroxide solution is washed with water before the solution adhering to its surface dries. A method for producing a thermosetting plastic molded article having an ultraviolet curable cured coating on its surface as claimed in claim 1 or 2. 8. A patent claim characterized in that the time required for washing a thermosetting plastic molded article made of diethylene glycol bisallyl carbonate or its copolymer to which an alkali metal hydroxide solution has adhered is 30 seconds or less. A method for producing a thermosetting plastic molded article having an ultraviolet curable cured coating on its surface according to Item 7.