JPH1017556A - Triazine-based compound, ultraviolet absorber consisting thereof and composition containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a triazine-based compound bearing substituents on respectively specific sites, affording an ultraviolet absorber excellent in heat resistance, and capable of imparting organic materials with high weatherability without discoloration when incorporated in the materials. SOLUTION: This triazine-based compound is shown by the formula ((n) is 1 or 2; R1 is H, a 1-12C alkyl, glycidyl, a 3-8C cycloalklyl, 3-8C alkenyl, 6-18C aryl, etc.; R2 is H or a 1-8C alkyl; R3 to R6 are each H, a halogen, hydroxyl, a 1-12C alkyl, etc.), e.g. 2-(2-hydroxy-3-methyl-4-propyloxyphenyl)-4,6- diphenyltriazine. This compound of the formula is obtained, pref., for example, by adding 1mol of phenol to 1mol of cyanuric chloride followed by addition of 2mol of xylene in the presence of aluminum trichloride as catalyst and then by exchange reaction between the phenol and 2,6-dihydroxytoluene followed by reaction of the product with propyl bromide.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a triazine compound having a specific structure, an ultraviolet absorber comprising the same, and a thin film composition or a fibrous composition having improved weather resistance by the ultraviolet absorber. The present invention relates to a specific triazine-based compound, an ultraviolet absorbent comprising the same, and a thin film composition and a fibrous composition such as a film, a sheet or a paint having improved weather resistance.

[0002]

2. Description of the Related Art Polymer materials such as polyethylene, polypropylene, styrene resin, polyvinyl chloride, and polycarbonate, and organic pigments or dyes are deteriorated by the action of light, causing discoloration or reduction in mechanical strength. It is known that it cannot withstand long-term use.

[0003] Therefore, in order to prevent the deterioration of these organic materials and to control the wavelength of transmitted light, various ultraviolet absorbers have been conventionally used. As these ultraviolet absorbers, benzophenone-based, benzotriazole-based, 2,4,6-triaryltriazine-based and cyanoacrylate-based ultraviolet absorbers are known.

[0004] These ultraviolet absorbers exhibit different ultraviolet absorption spectra due to their differences in structure, and also differ in compatibility and volatility with organic materials. In particular, in the thin film used for the protective layer, a high amount of an ultraviolet absorber is added because a high ultraviolet shielding effect is required, the compatibility with the base layer is excellent, the volatility is small, and the absorption coefficient is small. A large UV absorber was required.

The known 2,4,6-triaryltriazine-based UV absorber having a structure similar to that of the specific UV absorber of the present invention has a high absorption coefficient and excellent heat resistance. However, 2- (2,4-dihydroxyphenyl)-
The 4,6-diaryl-s-triazine compound has maximum absorption wavelengths of 275 to 290 nm and 330 to 340 nm, small absorption at 300 to 320 nm, and 350 to 350 nm.
The absorption at 400 nm was also small and not practical as compared with the benzotriazole-based ultraviolet absorber.

For this reason, Japanese Patent Application Laid-Open No. 8-53427 proposes to shift the ultraviolet absorption spectrum of a 2,4,6-triaryltriazine type ultraviolet absorber to a wavelength effective for stabilization by a substituent. I have. For example, by introducing a substituent at the 5-position of the 2,4-dihydroxyphenyl group of 2- (2,4-dihydroxyphenyl) -4,6-diaryltriazine, the maximum absorption at 330 to 340 nm is shifted to around 350 nm. , 350-4
The stabilizing effect is enhanced by improving the absorption at 00 nm. However, since the absorption wavelength includes visible light, it was colored and impractical.

In Japanese Patent Application Laid-Open No. 61-24577, 2,4-bis- (2,4-dihydroxy-3-methylphenyl) -6-phenyltriazine is described in Examples. However, a triazine compound having two dihydroxyphenyl groups has an absorption wavelength range of 400 n.
It was not practical to color the organic material beyond m.

[0008]

Means for Solving the Problems The present inventors have made intensive studies in view of the above situation, and as a result, have found the following general formula (I)
It has been found that an ultraviolet absorber composed of a triazine compound having a substituent at a specific position represented by represents a high degree of weather resistance without coloring an organic material and has excellent heat resistance, and has reached the present invention. .

That is, the present invention provides a triazine compound represented by the following general formula (I) and an ultraviolet absorbent comprising the same.

[0010]

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Hereinafter, the present invention having the above gist will be described in detail.

In the above formula, the alkyl groups represented by R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ may be, for example, methyl, ethyl, propyl, isopropyl, butyl, Sec-butyl, tert-butyl, isobutyl, amyl, tert-amyl, octyl, tert-octyl, decyl,
Undecyl, dodecyl and the like. Examples of the arylalkyl group include 1-methyl-1-phenylethyl, benzyl, 2-phenylethyl and the like.

The cycloalkyl group represented by R ¹ includes cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl and the like.

The alkenyl group represented by R ₁ includes linear and branched propenyl, butenyl, pentenyl, hexenyl, heptenyl and octenyl, irrespective of the position of the unsaturated bond.

The aryl group represented by R ₁ includes, for example, phenyl, naphthyl, biphenyl and the like. Further, as the aryl group having a substituent or insertion,
4-methylphenyl, 3-chlorophenyl, 4-benzyloxyphenyl, 4-cyanophenyl, 4-phenoxyphenyl, 4-glycidyloxyphenyl, 4-isocyanurate phenyl and the like.

The substituent represented by R ₁ and the optionally substituted alkyl group and cycloalkyl group include 2
-Hydroxypropyl, 2-methoxyethyl, 3-sulfo-2-hydroxypropyl, 4-methylcyclohexyl and the like.

The alkylene group represented by R ₁ includes, for example, methylene, ethylene, propylene, trimethylene, tetramethylene, pentamethylene, 2,2-dimethylpropylene, hexamethylene, heptamethylene, octamethylene and the like. Examples of the cycloalkylene group include cyclopentylene and cyclohexylene.

The arylene group represented by R ₁ includes:
1,3-phenylene and 1,4-phenylene are mentioned. Examples of the combination of an alkylene group and an arylene group include 1,3-xylylene, 1,4-xylylene,
-(1-phenyl-1-methyl-ethyl) phenyl and the like.

Examples of the substituent represented by R ₁ , an optionally substituted alkylene group, an arylene group and a combination thereof include -C ₂ H ₄ (OC ₂ H ₄ ) _m- , -CH (CH ₃ ) CH ₂ (OC
_{H 2 CH (CH 3))} m -, - C 2 H 4 NHC 2 H 4 -, - CH 2 CH (OH) CH 2 -, - C 2 H 4 O
—C ₆ H ₄ —C (CH ₃ ) ₂ —C ₆ H ₄ OC ₂ H ₄ — and the like.

The alkoxy group and alkoxycarbonyl group represented by R ₂ , R ₃ , R ₄ , R ₅ and R ₆ include derivatives of the aforementioned alkyl groups. Examples of the arylalkyl group include a cumyl group and a benzyl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.

The triazine compound represented by the above general formula (I) of the present invention includes, for example, the following compound No.
1 to No. 6 and the like.

[0022]

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[0023]

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[0024]

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[0025]

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[0026]

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[0027]

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The method for synthesizing the triazine compound represented by the general formula (I) of the present invention is not particularly limited, and may be any of the commonly used synthesis methods. For example, Compound No. 2 is obtained by adding 1 mol of phenol to 1 mol of cyanuric chloride, further adding 2 mol of xylene with an aluminum trichloride catalyst, and adding phenol and 2,6-
By performing an exchange reaction with dihydroxytoluene, 2- (2,2
(4-dihydroxy-3-methylphenyl) -4,6-diphenyltriazine was synthesized and reacted with propyl bromide to give 2- (2-hydroxy-3-methyl-4-
(Propyloxyphenyl) -4,6-diphenyltriazine is synthesized.

The thin film composition to which the ultraviolet absorbent comprising the triazine compound of the present invention is applied may be a synthetic resin film, sheet, paint or the like, and the fibrous composition may be nonwoven fabric or nonwoven fabric. Fibers used for woven fabrics and the like may be used. Specifically, in addition to films and sheets such as agricultural materials, fiber materials such as PET and polyester fibers and nylon fibers, synthetic polymer materials such as intraocular lenses and tapes, thermal recording materials, paints, adhesives Agents, putty, lacquer binders, substrates in photographic materials, liquid crystal compositions and the like. In particular, it is suitably used as a paint used for the outermost layer of a laminated film or a top coat layer for protecting a painted surface. When the stabilization target is a synthetic polymer material, the amount of the specific ultraviolet absorber of the present invention is usually 0.0
The amount is from 0.01 to 30 parts by weight, preferably from 0.01 to 10 parts by weight.

The ultraviolet absorber of the present invention has low volatility and imparts excellent weather resistance, and is therefore particularly useful in fields requiring high weather resistance such as agricultural materials and automotive paints. Because of the bonding, a particularly excellent stabilizing effect can be expected when incorporated into a thermosetting paint or the like.

Examples of the synthetic polymer material to which the ultraviolet absorbent of the present invention is added to improve stability include, for example, high density, low density or linear low density polyethylene, polypropylene, polybutene-1, and poly-3. Α-olefin polymers such as methylpentene or ethylene-vinyl acetate copolymers, polyolefins such as ethylene-propylene copolymers and their copolymers, polyvinyl chloride, polyvinylidene chloride, chlorinated polyethylene, chlorinated polypropylene , Polyvinylidene fluoride, chloride rubber, vinyl chloride-vinyl acetate copolymer, vinyl chloride-ethylene copolymer, vinyl chloride-vinylidene chloride copolymer, vinyl chloride-vinylidene chloride-vinyl acetate terpolymer, vinyl chloride -Acrylic acid ester copolymer, vinyl chloride-maleic acid ester copolymer, Vinyl - cyclohexyl maleimide copolymer, vinyl chloride - halogen-containing resins such as cyclohexyl maleimide copolymer, petroleum resin, coumarone resin,
Copolymers of polystyrene, polyvinyl acetate, acrylic resin, styrene and / or α-methylstyrene and other monomers (eg, maleic anhydride, phenylmaleimide, methyl methacrylate, butadiene, acrylonitrile, etc.) (for example, AS resin, ABS resin, MBS resin, heat-resistant ABS resin, etc.), polymethyl methacrylate, polyvinyl alcohol, polyvinyl formal, polyvinyl butyral, linear polyester such as polyethylene terephthalate and polytetramethylene terephthalate, polyphenylene oxide, polycaprolactam and polyhexamethylene Thermoplastic synthetic resins such as polyamides such as adipamide, polycarbonates, branched polycarbonates, polyacetals, polyphenylene sulfides, polyurethanes and cellulose resins These blends or phenolic resins, urea resins, melamine resins, epoxy resins, and thermosetting resins such as unsaturated polycarboxylic Castel resin. Further, elastomers such as isoprene rubber, butadiene rubber, acrylonitrile-butadiene copolymer rubber, and styrene-butadiene copolymer rubber may be used.

The ultraviolet absorber of the present invention can be used in combination with other general-purpose additives such as antioxidants and stabilizers, if necessary.

Particularly preferable examples of these additives include phenol-based, sulfur-based, phosphite-based antioxidants and hindered amine-based light stabilizers.
In particular, a hindered amine-based light stabilizer represented by a 2,2,6,6-tetramethylpiperidine compound is preferable because it exhibits a synergistic effect with the triazine-based compound of the present invention.

The phenolic antioxidants include, for example, 2,6-di-tert-butyl-p-cresol, 2,6
-Diphenyl-4-octadecyloxyphenol, stearyl (3,5-di-tert-butyl-4-hydroxyphenyl) -propionate, distearyl (3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate, thiodiethylene glycol Bis [(3,5-ditert-butyl-
4-hydroxyphenyl) propionate], 1,6-
Hexamethylene bis [(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 1,6-hexamethylene bis [(3,5-di-tert-butyl-4-hydroxyphenyl) propionamide], 4,4′-thiobis (6-tert-butyl-m-cresol), 2,2′-methylenebis (4-methyl-6-tert-butylphenol), 2,2′-methylenebis (4-ethyl-6-tert-butyl) Tributylphenol), bis [3,3-bis (4-hydroxy-3-tert-butylphenyl) butylic acid]
Glycol ester, 4,4'-butylidenebis (6-
Tert-butyl-m-cresol), 2,2′-ethylidenebis (4,6-di-tert-butylphenol), 2,2′-
Ethylidenebis (4-sec-butyl-6-tert-butylphenol), 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, bis [2-
Tert-butyl-4-methyl-6- (2-hydroxy-3-
Tert-butyl-5-methylbenzyl) phenyl] terephthalate, 1,3,5-tris (2,6-dimethyl-3-
Hydroxy-4-tert-butylbenzyl) isocyanurate, 1,3,5-tris (3,5-di-tert-butyl-4-
Hydroxylbenzyl) isocyanurate, 1,3,5-
Tris (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, 1,3,5-
Tris [(3,5-di-tert-butyl-4-hydroxyphenyl) propionyloxyethyl] isocyanurate,
Tetrakis [methylene-3- (3,5-di-tert-butyl-
4-hydroxyphenyl) propionate] methane, 2
-Tert-butyl-4-methyl-6- (2-acryloyloxy-3-tert-butyl-5-methylbenzyl) phenol, 3,9-bis [1,1-dimethyl-2-−２ (3-tert-butyl Butyl-4-hydroxy-5-methylphenyl) propionyloxydiethyl] -2,4,8,10-tetraoxaspiro [5.5] undecane, triethylene glycol bis [(3-tert-butyl-4-hydroxy) −5-
Methylphenyl) propionate].

Examples of the sulfur-based antioxidant include dialkylthiodipropionates such as dilauryl thiodipropionate, dimyristyl and distearyl, and polyols such as pentaerythritol tetra (β-dodecylmercaptopropionate). β-alkylmercaptopropionates.

Examples of the phosphite-based antioxidant include trisnonylphenyl phosphite, tris (2,4-di-tert-butylphenyl) phosphite,
Tris [2-tert-butyl-4- (3-tert-butyl-4-
[Hydroxy-5-methylphenylthio) -5-methylphenyl] phosphite, tridecyl phosphite, octyl diphenyl phosphite, di (decyl) monophenyl phosphite, di (tridecyl) pentaerythritol diphosphite, distearyl pentaerythritol Diphosphite, di (nonylphenyl) pentaerythritol diphosphite, bis (2,4-ditertbutylphenyl) pentaerythritol diphosphite, bis (2,6-ditertbutyl-4-methylphenyl) penta Erythritol diphosphite, bis (2,4,6-tri-tert-butylphenyl) pentaerythritol diphosphite, tetra (tridecyl) isopropylidenediphenol diphosphite, tetra (tridecyl) -4,
4'-n-butylidenebis (2-tert-butyl-5-methylphenol) diphosphite, hexa (tridecyl)
-1,1,3-tris (2-methyl-4-hydroxy-
5-tert-butylphenyl) butanetriphosphite,
2,2'-methylenebis (4,6-di-tert-butylphenyl) -2-ethylhexyl phosphite, 2,2'-methylene bis (4,6-di-tert-butylphenyl) octadecyl phosphite, 2,2'- Ethylidenebis (4,6
-Di-tert-butylphenyl) fluorophosphite, tetrakis (2,4-di-tert-butylphenyl) biphenylenediphosphonite, 9,10-dihydro-9-oxa-
10-phosphaphenanthrene-10-oxide, tris (2-[(2,4,8,10-tetrakis-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphepin-6 -Yl) oxy] ethyl) amine and the like.

The hindered amine light stabilizer includes, for example, 2,2,6,6-tetramethyl-4-
Piperidyl benzoate, N- (2,2,6,6-tetramethyl-4-piperidyl) dodecylsuccinimide,
1-[(3,5-di-tert-butyl-4-hydroxyphenyl) propionyloxyethyl] -2,2,6,6-tetramethyl-4-piperidyl- (3,5-di-tert-butyl-4- (Hydroxyphenyl) propionate, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-
4-piperidyl) sebacate, bis (1,2,2,6)
6-pentamethyl-4-piperidyl) -2-butyl-2
-(3,5-di-tert-butyl-4-hydroxybenzyl)
Malonate, N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine, tetra (2,2,6,6-tetramethyl-4-piperidyl) butanetetracarboxylate, Tetra (1, 2,
2,6,6-pentamethyl-4-piperidyl) butanetetracarboxylate, bis (2,2,6,6-tetramethyl-4-piperidyl) di (tridecyl) butanetetracarboxylate, bis (1,2,2 2,6,6-pentamethyl-4-piperidyl) di (tridecyl) butanetetracarboxylate, 3,9-bis [1,1-dimethyl-2- {tris (2,2,6,6-tetramethyl- 4-piperidyloxycarbonyloxy) butylcarbonyloxydiethyl] -2,4,8,10-tetraoxaspiro [5.5] undecane, 3,9-bis [1,
1-dimethyl-2- {tris (1,2,2,6,6-pentamethyl-4-piperidyloxycarbonyloxy)
Butylcarbonyloxydiethyl] -2,4,8,10
-Tetraoxaspiro [5.5] undecane, 1,5
8,12-tetrakis [4,6-bis {N- (2,2,
6,6-tetramethyl-4-piperidyl) butylamino {-1,3,5-triazin-2-yl] -1,5.
8,12-tetraazadodecane, 1- (2-hydroxyethyl) -2,2,6,6-tetramethyl-4-piperidinol / dimethyl succinate condensate, 2-tert-octylamino-4,6-dichloro -S-triazine / N, N '
-Bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine, N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine / And dibromoethane condensates.

In addition, if necessary, a heavy metal deactivator, a nucleating agent, a metal soap, an organotin compound, a plasticizer, an epoxy compound, a foaming agent, an antistatic agent, a flame retardant, a lubricant, together with the ultraviolet absorber of the present invention. , A processing aid or the like can be used in combination.

The method of applying the ultraviolet absorbent of the present invention to an organic material is not particularly limited, and the form in which it is added may be a powder, an aqueous dispersion such as an emulsion or a suspension, or a solution with an organic solvent. Good. Also,
Since the ultraviolet absorbent of the present invention has an unsaturated bond, it may be used alone or as an oligomer by copolymerizing with another monomer as the ultraviolet absorbent (triazine-based compound represented by the general formula (I)). it can.

Further, the addition process can be variously changed depending on the form of addition, and when the organic material to be stabilized is a polymer material, any of the commonly used methods of applying an ultraviolet absorber to a polymer material can be used. Good. For example, it may be added during processing, may be adsorbed and impregnated after processing, or may be coated with a film or the like to which the ultraviolet absorbent of the present invention has been added. In the method of addition at the time of processing, a master batch blended at a high concentration may be prepared, or kneaded in a final desired blend after granulation is suppressed to dust. In a paint, a heat-sensitive recording material, a liquid crystal composition, or the like, it may be directly added, or may be added to a protective layer.

[0041]

Next, the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples.

Specific examples of the synthesis of the triazine compound represented by the general formula (I) used in the present invention are described below, but the present invention is not limited by the following synthesis examples.

(Synthesis Example 1: Synthesis of Compound No. 1) 2-Chloro-4,6-bis (2,4-dimethylphenyl) -s-triazine was added to 124 g (1.0 mol) of 2-methylresorcinol. 323.5 g (1.0 mol) and 147 g (1.1 mol) of aluminum trichloride were refluxed in toluene for 2 hours. After removing aluminum trichloride as a catalyst by a conventional method, the solvent was removed under reduced pressure, and 379 g of a pale yellow powder having a melting point of 193 ° C. was obtained by recrystallization from isopropanol (yield 9).
2.3%).

The obtained compound was analyzed by H ¹ -NMR for compound No. It was identified as 1. 1.1 (-CH ₃ ), 1.7-2.0 (-CH _2- ), 2.2 (-CH ₃ ), 2.4,2.7 (-CH ₃ ),
4.0 (-CH _2- ), 6.5-6.6,7.1-7.3,8.0-8.2,8.4-8.6 (Ar-H)

(Synthesis Example-2: Synthesis of Compound No. 2) Compound No. 2 obtained in the above Synthesis Example-1 was synthesized. 1
82.2 g (0.2 mol), caustic soda 9.6 g
(0.24 mol) in N, N-dimethylformamide 80
0 ml, and 24.3 g of propyl bromide (0.
(24 mol) was added dropwise, and the mixture was reacted at 80 ° C. for 3 hours. After cooling, 200 ml of a 1N aqueous hydrochloric acid solution was added.
76.7 g (yield: 84.7%) of a pale yellow powder having a temperature of 7 ° C was obtained.

The obtained compound was analyzed by H ¹ -NMR for compound No. 2 was identified. 1.1 (-CH ₃ ), 1.7-2.0 (-CH _2- ), 2.2 (-CH ₃ ), 2.4,2.7 (-CH ₃ ),
4.0 (-CH _2- ), 6.5-6.6,7.1-7.3,8.0-8.2,8.4-8.6 (Ar-H)

(Example-1) By the composition shown in Table 1 below,
Extrusion was performed at 250 ° C. to produce pellets. Next, a sheet having a thickness of 2 mm was prepared by injection molding at 250 ° C., and the yellowness was measured. The sheet was subjected to a weather resistance test using a sunshine weatherometer with a rain cycle of 18 minutes in 120 minutes at a black panel temperature of 83 ° C. The evaluation was performed by comparing the crack generation time.

The results are shown in Table 2 below.

[0049]

[Table 1]

[0050]

[Table 2]

[0051]

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[0052]

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(Example 2) 100 g of methyl methacrylate and 66 g of n-butyl acrylate were used as base coat paints.
g, 2-hydroxyethyl methacrylate 30 g, methacrylic acid 4 g, xylene 80 g and n-butanol 2
Of azobisisobutyronitrile, 0.5 g of dodecyl mercaptan, and 80 g of xylene.
And a solution consisting of 20 g of n-butanol was added dropwise over 3 hours. The reaction was further performed for 2 hours to prepare an acrylic resin solution having a resin solid content of 50%. To 12 parts by weight of this acrylic resin solution, 2.5 parts by weight of butoxylated methylol melamine, 50 parts by weight of cellulose acetate butyrate resin, 5.5 parts by weight of aluminum pigment, 10 parts by weight of xylene, 20 parts by weight of butyl acetate and 0 parts by weight of copper phthalocyanine blue 2 parts by weight was used as a base coat paint.

100 g of methyl methacrylate, 66 g of n-butyl acrylate, 30 g of 2-hydroxyethyl methacrylate, 4 g of methacrylic acid, 2 g of an ultraviolet absorber (see Table 3), 80 g of xylene and 20 g of n-butanol
Is heated to 110 ° C., and azobisisobutyronitrile 2
g, 0.5 g of dodecyl mercaptan, 80 g of xylene and 20 g of n-butanol were added dropwise over 3 hours. The reaction was further performed for 2 hours to prepare an acrylic resin solution having a resin solid content of 50%. To 48 parts by weight of this acrylic resin solution, 10 parts by weight of butoxylated methylol melamine, 10 parts by weight of xylene, and 4 parts by weight of butyl glycol acetate were added and mixed to obtain a top coat paint.

The base coat paint is sprayed on the primer-treated steel sheet so that the dry film thickness becomes 20 μm.
After standing for 10 minutes, dry the top coat paint
It was sprayed to be 0 μm. After 15 minutes, 14
Baking was performed at 0 ° C. for 30 minutes to prepare a test piece.

The obtained test piece was put into a sunshine weatherometer, and the time until cracks occurred in the coating film was measured. Table 3 shows the results.

[0057]

[Table 3]

(Example 3) A film having a thickness of 0.1 mm was produced by kneading with a kneading roll using the compounds shown in Table 4 below. A test piece was cut from the film and subjected to a weather resistance test using a sunshine weatherometer (without rain).

Table 5 shows the results.

[0060]

[Table 4]

[0061]

[Table 5]

(Example-4) A liquid obtained by finely dispersing 35 parts by weight of an ultraviolet absorber (described in Table 6) in 1 part by weight of a nonionic surfactant (an adduct of nonylphenol and ethylene oxide) and 64 parts by weight of water. 30 g, anthraquinone red dye (Resolin Red FB: manufactured by Bayer) 10 g, and acetic acid 0.1 g.
3 g was dispersed in 1 liter of water to obtain a dye liquor, with a bath ratio of 1: 1.
100 g of polyester cloth in a closed container at 130
Dyeing was carried out for 30 minutes in a thermostat bath. After cooling, it was washed with water and reduced and washed by a conventional method to obtain a test piece. The exhaustion rate of the ultraviolet absorbent was measured from the absorbance before and after the dyeing liquor was dyed. In addition, a weather resistance test was performed on the obtained dyed fabric by a color difference from that before the test at 83 ° C. (without watering) at 240 ° C. (without watering).

The exhaustion rate was also measured when there was no dye. The results are shown in the following Table-6.

[0064]

[Table 6]

Example 5 A protective layer 40 μm obtained by adding 10 parts by weight of an ultraviolet absorber described in Table 7 to 100 parts by weight of a bisphenol A polycarbonate having an intrinsic viscosity of 0.57 (in dioxane, at 30 ° C.) A sheet was obtained by laminating 10 mm of the base material layer to which no ultraviolet absorber was added by co-extrusion at 280 ° C. × 80 rpm. The obtained sheet was evaluated for weather resistance by a color difference before and after irradiation with a high-pressure mercury lamp for 2 weeks.

Table 7 shows the results.

[0067]

[Table 7]

[0068]

From the results of the above examples, it can be seen that when the specific ultraviolet absorbent of the present invention is used, the thin film composition or the thin-film composition can be compared with the conventionally known triazine-based ultraviolet absorbent. It is clear that the stabilizing effect of the fibrous composition is significantly greater.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification number Agency reference number FI Technical display location C08K 5/3492 KKK C08K 5/3492 KKK

Claims (6)

[Claims] 1. A triazine compound represented by the following general formula (I). Embedded image 2. An ultraviolet absorber comprising a triazine compound represented by the general formula (I). 3. A thin film composition to which the ultraviolet absorbent according to claim 2 is added. 4. The thin film composition according to claim 3, which is a coating film. 5. The thin film composition according to claim 3, which is a film. 6. A fibrous composition to which the ultraviolet absorbent according to claim 2 is added.