JPH11292859A - 2h-benzotriazole derivative and its production and use - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound little in volatilization and dissipation, high in stability, excellent in compatibility with a base material and ultraviolet ray absorbability and useful for ultraviolet ray absorbents and weather-resistant organic polymer compounds. SOLUTION: This compound, e.g. 2,4-bis[2-hydroxy-3-(2H-benzotriazole-2-yl)-5 methylphenylureilene]toluene, shown by formula I (R is e.g. H or alkyl; R<1> is e.g. a halogen or alkyl; R<2> is e.g. H or alkyl; and (n) is 4 to 8) is obtained by reacting a compound [e.g. 2-(2-hydroxy-3-amino-5-methylphenyl)-2H- benzotriazole] of formula II with a compound (e.g. toluylene 2,4-diisocyanate) of formula III in an organic solvent e.g. tetrahydrofuran pref. at 20 to 80 deg.C.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a 2H-benzotriazole derivative having excellent ultraviolet absorbing ability, low scattering and high light stability, an ultraviolet absorber containing the same, a weather-resistant organic polymer composition and the 2H-benzotriazole derivative. The present invention relates to a method for producing a benzotriazole derivative.

[0002]

2. Description of the Related Art Many ultraviolet absorbers are currently used to prevent organic polymer substances from being deteriorated by ultraviolet rays. Representative UV absorbers include benzophenone, benzotriazole, cyanoacrylate, and salicylate. These absorb ultraviolet rays and dissipate them as harmless energy, thereby preventing deterioration of the organic polymer substance.

[0003] Many of the conventionally known ultraviolet absorbers are:
Although it has excellent ultraviolet absorption efficiency, it has a problem that it is partially decomposed or volatilized when kneaded into an organic polymer material and heated and processed, or gradually volatilized and scattered when used as a molded product after processing. To improve this, by increasing the molecular weight of the UV absorber or adding a non-volatile functional group,
Attempts have been made to improve the shortcomings of volatilization and scattering, but they have not been sufficiently satisfactory in terms of ultraviolet absorption efficiency.

[0004]

SUMMARY OF THE INVENTION The first object of the present invention is to reduce volatilization and scattering, to have high stability, to have excellent compatibility with a substrate, and to have an ultraviolet absorbing ability, that is, an extremely high molecular absorption coefficient. It is to provide a large novel compound and a method for producing the same. A second object of the present invention is to provide a novel ultraviolet absorber utilizing the above-mentioned ultraviolet absorbing ability and a weather-resistant organic polymer composition containing the same.

[0005]

Means for Solving the Problems A first aspect of the present invention is that the general formula (1)

Embedded image (Wherein, R represents a hydrogen atom, a halogen atom, a group selected from the group consisting of alkyl and alkoxy groups, R ¹
Is a group selected from the group consisting of a halogen atom, an alkyl group and an alkoxy group, and R ² is selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an amino group, an acylamino group and an aroylamino group Group. )).

A second aspect of the present invention relates to an ultraviolet absorber containing the 2H-benzotriazole derivative according to the first aspect.

A third aspect of the present invention relates to a weather-resistant organic polymer composition containing the 2H-benzotriazole derivative according to the first aspect.

A fourth aspect of the present invention is the following general formula (2):

Embedded image (Wherein R ¹ and R ² are the same as described above) and a compound represented by the following general formula (3)

Embedded image Wherein R is the same as defined above, wherein an aryl diisocyanate represented by the following general formula (1) is reacted in an organic solvent:

Embedded image (Wherein, R, R ¹ and R ² are the same as described above).

Examples of the alkyl group represented by R include:
Examples thereof include a methyl group, an ethyl group, an n-propyl group, and an iso-propyl group.
Are preferred. Examples of the alkoxy group include a methoxy group, an ethoxy group, and an n-propoxy group, and the number of carbon atoms is preferably 1 to 3.

Examples of the alkyl group for R ¹ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a tert-butyl group, a tert-amyl group,
Although a tert-octyl group etc. can be mentioned, those having 1 to 8 carbon atoms are preferable. Examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group and the like, and those having 1 to 3 carbon atoms are preferred.

Examples of the alkyl group represented by R ² include a methyl group, an ethyl group and an n-propyl group, and preferably have 1 to 3 carbon atoms. Examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group and the like, and those having 1 to 3 carbon atoms are preferred. Examples of the acylamino group include an acetylamino group, a propionylamino group, an n-valeroylamino group, an iso-valeroylamino group, and the like.
Are preferred. Examples of the aroylamino group include a benzoylamino group, a toluoylamino group, an anisoylamino group, and the like.

Examples of the organic solvent used in the above reaction include:
Usually, dichloromethane, dichloroethane, di-iso-propyl ether, 1,4-dioxane, tetrahydrofuran and the like can be mentioned. The reaction is carried out at a temperature around the boiling point of the solvent, but preferably at 20 to 80 ° C.

Specific examples of the 2H-benzotriazole derivative represented by the general formula (1) used in the present invention include, for example, 1,3-bis [2-hydroxy-3- (2H-benzotriazole-2- Il) -5-
Methylphenylureylene] benzene, 1,3-bis [2-hydroxy-3- (2H-benzotriazole-
2-yl) -5-tert-butylphenylureylene] benzene, 1,3-bis [2-hydroxy-3-
(2H-benzotriazol-2-yl) -5-ter
t-amylphenylureylene] benzene, 1,3-bis [2-hydroxy-3- (2H-benzotriazol-2-yl) -5-tert-octylphenylureylene] benzene, 2,4-bis [2 -Hydroxy-3-
(2H-Benzotriazol-2-yl) -5-methylphenylureylene] toluene, 2,4-bis [2-hydroxy-3- (2H-benzotriazol-2-yl) -5-tert-butylphenylurei Len] toluene, 2,4-bis [2-hydroxy-3- (2H-benzotriazol-2-yl) -5-tert-amylphenylureylene] toluene, 2,4-bis [2-hydroxy-3- (2H-benzotriazol-2-yl) -5-tert-octylphenylureylene] toluene, 1,3-bis [2-hydroxy-3- (5-chloro-2H-benzotriazol-2-yl) -5 -Methylphenylureylene] benzene, 1,3-bis [2
-Hydroxy-3- (5-chloro-2H-benzotriazol-2-yl) -5-tert-butylphenylureylene] benzene, 1,3-bis [2-hydroxy-
3- (5-chloro-2H-benzotriazol-2-yl) -5-tert-amylphenylureylene] benzene, 1,3-bis [2-hydroxy-3- (5-chloro-2H-benzotriazole- 2-yl) -5-te
rt-octylphenylureylene] benzene, 2,4
-Bis [2-hydroxy-3- (5-chloro-2H-benzotriazol-2-yl) -5-methylphenylureylene] toluene, 2,4-bis [2-hydroxy-
3- (5-chloro-2H-benzotriazol-2-yl) -5-tert-butylphenylureylene] toluene, 2,4-bis [2-hydroxy-3- (5-chloro-2H-benzotriazole- 2-yl) -5-te
rt-amylphenylureylene] toluene, 2,4-
Bis [2-hydroxy-3- (5-chloro-2H-benzotriazol-2-yl) -5-tert-octylphenylureylene] toluene, 1,4-bis [2-hydroxy-3- (5-bromo -2H-benzotriazol-2-yl) -5-methylphenylureylene] benzene, 1,3-bis [2-hydroxy-3- (5-bromo-2H-benzotriazol-2-yl) -5-te
rt-butylphenylureylene] benzene, 1,3-
Bis [2-hydroxy-3- (5-bromo-2H-benzotriazol-2-yl) -5-tert-amylphenylureylene] benzene, 1,3-bis [2-hydroxy-3- (5-bromo -2H-benzotriazol-2-yl) -5-tert-octylphenylureylene] benzene, 2,4-bis [2-hydroxy-3-
(5-bromo-2H-benzotriazol-2-yl)
-5-methylphenylureylene] toluene, 2,4-
Bis [2-hydroxy-3- (5-bromo-2H-benzotriazol-2-yl) -5-tert-butylphenylureylene] toluene, 2,4-bis [2-hydroxy-3- (5-bromo -2H-benzotriazol-2-yl) -5-tert-amylphenylureylene] toluene, 2,4-bis [2-hydroxy-3-
(5-bromo-2H-benzotriazol-2-yl)
-5-methylphenylureylene] toluene, 1,3-
Bis [2-hydroxy-3- (5-methyl-2H-benzotriazol-2-yl) -5-methylphenylureylene] benzene, 1,3-bis [2-hydroxy-3
-(5-methyl-2H-benzotriazol-2-yl) -5-tert-butylphenylureylene] benzene, 1,3-bis [2-hydroxy-3- (5-methyl-2H-benzotriazole-2) -Il) -5-te
rt-amylphenylureylene] benzene, 1,3-
Bis [2-hydroxy-3- (5-methyl-2H-benzotriazol-2-yl) -5-tert-octylphenylureylene] benzene, 1,3-bis [2-hydroxy-3- (6-methyl) -2H-benzotriazol-2-yl) -5-methylphenylureylene] benzene, 1,3-bis [2-hydroxy-3- (6-methyl-2H-benzotriazol-2-yl) -5-te
rt-butylphenylureylene] benzene, 1,3-
Bis [2-hydroxy-3- (6-methyl-2H-benzotriazol-2-yl) -5-tert-amylphenylureylene] benzene, 1,3-bis [2-hydroxy-3- (6-methyl) -2H-benzotriazol-2-yl) -5-tert-octylphenylureylene] benzene, 2,4-bis [2-hydroxy-3-
(5-methyl-2H-benzotriazol-2-yl)
-5-methylphenylureylene] toluene, 2,4-
Bis [2-hydroxy-3- (5-methyl-2H-benzotriazol-2-yl) -5-tert-butylphenylureylene] toluene, 2,4-bis [2-hydroxy-3- (5-methyl) -2H-benzotriazol-2-yl) -5-tert-amylphenylureylene] toluene, 2,4-bis [2-hydroxy-3-
(5-methyl-2H-benzotriazol-2-yl)
-5-tert-octylphenylureylene] toluene, 2,4-bis [2-hydroxy-3- (6-methyl-2H-benzotriazol-2-yl) -5-methylphenylureylene] toluene, 2, 4-bis [2-hydroxy-3- (6-methyl-2H-benzotriazol-2-yl) -5-tert-butylphenylureylene] toluene, 2,4-bis [2-hydroxy-3-
(6-methyl-2H-benzotriazol-2-yl)
-5-tert-amylphenylureylene] toluene, 2,4-bis [2-hydroxy-3- (6-methyl-2H-benzotriazol-2-yl) -5-ter
[t-octylphenylureylene] toluene and the like.

The following general formula (2)

Embedded image (Wherein, R ¹ and R ² are the same as described above). Specific examples of the compound include 2- (2-hydroxy-3-amino-5-methylphenyl) -2H-benzotriazole,
2- (2-hydroxy-3-amino-5-tert-butylphenyl) -2H-benzotriazole, 2- (2
-Hydroxy-3-amino-5-tert-amylphenyl) -2H-benzotriazole, 2- (2-hydroxy-3-amino-5-tert-octylphenyl)
-2H-benzotriazole, 2- (2-hydroxy-
3-amino-5-methylphenyl) -2H-5-chlorobenzotriazole, 2- (2-hydroxy-3-amino-5-tert-butylphenyl) -2H-5-chlorobenzotriazole, 2- (2- (Hydroxy-3-amino-5-tert-amylphenyl) -2H-5-chlorobenzotriazole, 2- (2-hydroxy-3-
Amino-5-tert-octylphenyl) -2H-5
-Chlorobenzotriazole, 2- (2-hydroxy-
3-amino-5-methylphenyl) -2H-5-bromobenzotriazole, 2- (2-hydroxy-3-amino-5-tert-butylphenyl) -2H-5-bromobenzotriazole, 2- (2- (Hydroxy-3-amino-5-tert-amylphenyl) -2H-5-bromobenzotriazole, 2- (2-hydroxy-3-
Amino-5-tert-octylphenyl) -2H-5
-Bromobenzotriazole, 2- (2-hydroxy-
3-amino-5-methylphenyl) -2H-5-methylbenzotriazole, 2- (2-hydroxy-3-amino-5-tert-butylphenyl) -2H-5-methylbenzotriazole, 2- (2- Hydroxy-3-amino-5-tert-amylphenyl) -2H-5-methylbenzotriazole, 2- (2-hydroxy-3-
Amino-5-tert-octylphenyl) -2H-5
-Methylbenzotriazole, 2- (2-hydroxy-
3-amino-5-methylphenyl) -2H-6-methylbenzotriazole, 2- (2-hydroxy-3-amino-5-tert-butylphenyl) -2H-6-methylbenzotriazole, 2- (2- (Hydroxy-3-amino-5-tert-amylphenyl) -2H-6-methylbenzotriazole, 2- (2-hydroxy-3-
Amino-5-tert-octylphenyl) -2H-6
-Methylbenzotriazole and the like.

The following general formula (3)

Embedded image (Wherein, R is the same as defined above), for example, 1,3-phenylene diisocyanate-
Toluylene 2,4-diisocyanate, toluylene 2,6-diisocyanate, 4-chloro-1,3-
Phenylene diisocyanate, 4-methoxy-1,3
-Phenylene diisocyanate, 1,4-phenylene diisocyanate, 2-chloro-1,4-phenylene diisocyanate, 2-methoxy-1,4-phenylene diisocyanate and the like.

The organic polymer substance stabilized by the compound represented by the general formula (1) may further contain a conventional additive, for example, an antioxidant, a light stabilizer, and a metal deactivator. And a peroxide scavenger.

Antioxidants which may be added in addition to the compounds according to the invention include, for example, 2,6-di-t-butyl-4-methylphenol, 2-t-4,6-dimethylphenol, 2,2 6-di-t-butyl-4-ethylphenol, 2,6-di-t-butyl-4-n-butylphenol, 2,6-di-t-butyl-4-isobutylphenol, 2,6-di- Cyclopentyl-4-methylphenol, 2- (α-methylcyclohexyl) -4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-dinonyl -4-methylphenol, 2,
6-di-t-butyl-4-methoxymethylphenol,
2,4-dimethyl-6- (1'-methyl-undeca-
1'-yl) -phenol, 2,4-dimethyl-6
(1'-methyl-heptadec-1'-yl) -phenol, 2,4-dimethyl-6- (1'-methyl-trideca-1'-yl) -phenol and mixtures thereof,
2,4-di-octylthiomethyl-6-t-butylphenol, 2,4-di-octylthiomethyl-6-methylphenol, 2,4-di-octylthiomethyl-6-ethylphenol, 2,6- Di-dodecylthiomethyl-4
-Nonylphenol and mixtures thereof, 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-
t-butylhydroquinone, 2,5-di-t-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-t-butylhydroquinone, 2,5-di-t-butyl-4 -Hydroxyanisole, 3,5-di-t-butyl-4-hydroxyanisole, 3,5-di-t-butyl-4-hydroxyphenyl stearate, bis (3,5-di-t-butyl-4-
(Hydroxyphenyl) adipate and mixtures thereof, 2,4-bis-octylmercapto-6- (3,5
-Di-t-butyl-4-hydroxyanilino) -1,
3,5-triazine, 2-octylmercapto-4,6
-Bis (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octylmercapto-4,6-bis (3,5-di-tert-butyl-4) -Hydroxyphenoxy) -1,3,5-triazine, 2,
4,6-tris (3,5-di-tert-butyl-4-hydroxyphenoxy) -1,2,3-triazine, 1,3
5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -isocyanurate, 1,3,5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) -isocyanate Nurate, 2,4,6-tris (3,5-di-t-butyl-4-hydroxyphenylethyl) -1,3,5-triazine, 1,3,5-tris (3,5-di-t -Butyl-4-hydroxyphenylpropionyl) -hexahydro-1,3,5-triazine, 1,3,5-tris (3,5-dicyclohexyl-
4-hydroxybenzyl) -isocyanurate and the like and 2,2'-methylenebis (6-t-butyl-4-methylphenol), 2,2'-methylenebis (6-t-butyl-4-ethylphenol), 2'-ethylidenebis (4,6-di-t-butylphenol), 2,2'-
Ethylidenebis (6-t-butyl-4-isobutylphenol), 4,4'-methylenebis (2,6-di-t-
Butylphenol), 4,4'-methylenebis (6-t
-Butyl-2-methylphenol), 1,1-bis (5
-T-butyl-4-hydroxy-2-methylphenyl)
Butane, ethylene glycol bis [3,3'-bis (3'-tert-butyl-4'-hydroxyphenyl) butyrate] and the like, and 1,3,5-tris (3,5-di-
t-butyl-4-hydroxybenzyl) -2,4,6-
Trimethylbenzene, 1,4-bis (3,5-di-t-
Butyl-4-hydroxybenzyl) -2,3,5,6-
Tetramethylbenzene, 2,4,6-tris (3,5-
Di-t-4-hydroxybenzyl) -phenol and the like.

Light stabilizers which may be added in addition to the compounds according to the invention include, for example, 2- (2'-hydroxy-
5'-methylphenyl) benzotriazole, 2-
(3 ', 5'-di-t-butyl-2'-hydroxyphenyl) benzotriazole, 2- (5'-t-butyl-
2'-hydroxyphenyl) benzotriazole, 2-
[2'-hydroxy-5 '-(1,1,3,3-tetramethylbutyl) phenyl] benzotriazole, 2-
(3 ', 5'-di-tert-butyl-2'-hydroxyphenyl) -5-chlorobenzotriazole, 2- (3'-
t-butyl-2'-hydroxy-5'-methylphenyl) -5-chlorobenzotriazole, 2- (2'-hydroxy-4'-octoxyphenyl) benzotriazole, 2- (3 ', 5'-di -T-amyl-2'-hydroxyphenyl) benzotriazole, 2- [3'-t
-Butyl-2'-hydroxy-5 '-(2'-octyloxycarbonylethylphenyl) -5-chlorobenzotriazole and the like: 4-hydroxy-, 4-methoxy-,
4-octoxy, 4-decyloxy-, 4-dodecyloxy-, 4-benzyloxy-, 4,2 ', 4'-trihydroxy-, 2'-hydroxy-4,4'-dimethoxy- or 4- ( 2-ethylhexyloxy) -2-
Hydroxybenzophenone derivatives, etc .: 4-t-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis (4-t-butylbenzoyl) resorcinol, 2,4-di-t-butylphenyl 3,5-di -T
-Butyl-4-hydroxybenzoate, hexadecyl 3,5-di-t-butyl-4-hydroxybenzoate, etc .: ethyl α-cyano-β, β-diphenylacrylate, isooctyl α-cyano-β, β-diphenylacrylate, methyl α-carbomethoxycinnamate, methyl α-cyano-β-methyl-p-methoxycinnamate and the like: bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (2,2,6, 6
-Tetramethyl-4-piperidyl) succinate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis (1-octyloxy-2,2,
6,6-tetramethyl-4-piperidyl) sebacate,
Bis (1,2,2,6,6-pentamethyl-4-piperidyl) adipate and the like: 4,4'-di-octyloxyoxanilide, 2,2'-diethoxyoxyoxanilide, 2,2 '-Di-octyloxy-5,5'-di-t
-Butyl oxanilide, 2,2'-di-dodecyloxy-5,5'-di-tert-butyl oxanilide, 2-ethoxy-2'-ethyl oxanilide, N, N'-bis (3 −
Dimethylaminopropyl) oxanilide, 2-ethoxy-5-t-butyl-2'-ethoxyoxanilide and the like:
2,4,6-tris (2-hydroxy-4-octyloxyphenyl) -1,3,5-triazine, 2- (2-
(Hydroxy-4-octyloxyphenyl) -4,6-
Bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2,4-dihydroxyphenyl) -4,
6-bis (2,4-dimethylphenyl) -1,3,5-
Triazine, 2,4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl ) -4,6-bis (2,
4-dimethylphenyl) -1,3,5-triazine and the like.

Metal deactivators which may be added in addition to the compounds according to the invention include, for example, N, N'-diphenyloxalic acid diamide, N-sartilal-N'-salicyloylhydrazine, N, N ' -Bis (salicyloyl) hydrazine, N, N'-bis (3,5-di-t-butyl-4)
-Hydroxyphenylpropionyl) hydrazine, 3-
Salicyloylamino-1,2,3-triazole, bis (benzylidene) oxalic acid hydrazide, isophthalic dihydrazide, N, N'-diacetal-adipic dihydrazide, N, N'-bis-salicyloyloxalic dihydrazide, N, N'-bis-salicyloyl-thiopropionic acid dihydrazide and the like.

Peroxide scavengers which may be added in addition to the compounds according to the invention include, for example, dilauryl-thiodipropionate, distearyl-thiodipropionate, dimyristyl-thiodipropionate or ditridecyl-thiodipropionate. And thiodipropionate, 2-mercaptobenzimidazole, and pentaerythritol tetrakis (dodecylmercapto) propionate.

The maximum absorption range of the 2H-benzotriazole derivative represented by the general formula (1) of the present invention is in the range of 280 to 350 nm, and has an extremely large ultraviolet absorption capacity as compared with a conventionally known ultraviolet absorber in the UV-B range. Have.

[0022]

EXAMPLES The present invention will now be described specifically with reference to examples of the compound of the present invention. However, these are merely examples of preferred embodiments, and the present invention is not limited to these examples. .

Example 1 2,4-bis [2-hydroxy-3- (2H-benzotriazol-2-yl) -5-methylphenylureylene] toluene [In the general formula (1), R = R ¹ = Synthesis of methyl, R ² = hydrogen atom] To 150 ml of tetrahydrofuran (THF) was added 2-hydroxy-3-amino-5-methylphenyl) -2H-benzotriazole (4.00 g, 16.7 mmol), and the mixture was stirred. At 40 ° C. with stirring. When a clear liquid was obtained, toluylene 2,4-diisocyanate (1.45 g, 8.45 g) dissolved in tetrahydrofuran (5 ml) was used.
(3 mmol) is added dropwise over 5 minutes at the same temperature. After the completion of the dropwise addition, the mixture is refluxed for 1 hour. About 10 minutes after the start of the heating and refluxing, the precipitation of the target substance starts. After cooling,
The solvent is removed by decantation. The residue was filtered off, and the resulting powder was treated with dimethylformamide (50 ml).
When recrystallized at a melting point of 220 to 221.5 ° C., 4.8
7 g (94%) of the purified product are obtained. The identification data of the compound is as follows.

Ultraviolet absorption spectrum (dimethylacetamide): λmax (nm) 316.0, εmax 27,
900 infrared absorption spectrum (KBr): cm ^-1 3358,
280 (OH and NH), 1660 (amide C = O),
1540, 1218 (coupling of amide NH and amide CN)

Example 2 2,4-bis [2-hydroxy-3- (2H-benzotriazol-2-yl) -5-tert-octylphenylureylene] toluene [In the general formula (1),
Synthesis of R = methyl, R ¹ = tert-octyl, R ² = hydrogen atom] 2- (2-hydroxy-3-amino-5-tert-octylphenyl) -2H-benzotriazole (4.00 g) in 20 ml of THF. , 11.8 mmol) and warm to 40 ° C. with stirring. When a clear liquid is obtained, toluylene dissolved in tetrahydrofuran (2 ml)
2,4-diisocyanate (1.03 g, 5.9 mmol
The solution of 1) is added dropwise at the same temperature over 5 minutes. After completion of the dropwise addition, the mixture is refluxed for 2 hours. After cooling, the reaction solution is poured into 5% saline (1000 ml) with vigorous stirring.
After the end of the injection, the stirring is continued for another 30 minutes. The precipitate is collected by filtration and dried. Dried product is isopropanol (60m
Heat to reflux with l) for 5 minutes. The insoluble target compound is collected by filtration while hot. The obtained powder was treated with dimethylformamide (4
3ml) and isopropanol (80ml), recrystallized, melting point: 214-215 ° C, 4.56g
(90%) of 2,4-bis [2-hydroxy-3- (2
H-benzotriazol-2-yl) -5-tert-
[Octylphenylureylene] toluene is obtained. The identification data of the compound is as follows.

UV absorption spectrum (chloroform): λ
max (nm) 323.5, εmax 38,000 infrared absorption spectrum (KBr): cm ^-1 3400,3
360 (OH and NH) 1670 (amide C = O),
1540, 1218 (coupling of amide C = O and amide CN).

Example 3 (Light Stabilizing Effect on Polymeric Substance) The samples prepared in Example 2 were added to 100 parts by weight of polyethylene powder or polypropylene powder, respectively, for 0.0%.
After blending 5 parts by weight, 0.2 parts by weight and 0.5 parts by weight and sufficiently mixing with a mixer, cylinder temperature 200
The mixture was melt-kneaded with a 25 mm diameter extruder at a temperature of 0 ° C. and granulated.
The obtained pellet was compression molded at 210 ° C. into a sheet having a thickness of 0.25 mm to prepare a test piece. The obtained test piece was punched out into a dumbbell type corresponding to a tensile test. In the same manner as above, a test piece for comparison and control without light stabilizer was prepared and evaluated.

These test pieces were prepared by using Suga Test Instruments Co., Ltd.
Using a EL-75XS-HS-BEC type xenon sunshine long life weatherometer, light was irradiated at a black panel temperature of 80 ° C., and the change over time in the decrease in tensile strength of each test piece was compared. The tensile test was performed using a DSS-5000 type tensile tester manufactured by Shimadzu Corporation at a temperature of 23 ± 2 ° C., a relative humidity of 50 ± 5%, and a test speed of 50 ± 5 min.
The measurement was performed at 5.0 mm. The tensile strength was determined by the following method.

(Equation 1) Ts = tensile strength (kgf / mm ² ) T = thickness of sample (mm) W = width of sample (mm) S = maximum strength of sample (kgf)

The results obtained are as shown in Table 1.
As is clear from the results shown in Table 1, 2
The H-benzotriazole derivative shows an excellent stabilizing effect (i.e., prolongs the deterioration time).

[Table 1]

[0030]

The novel compound of the present invention has an excellent ultraviolet absorbing ability, greatly prevents photodeterioration of organic substances, especially high molecular compounds, and is extremely stable to light, heat and moisture.

Claims (4)

[Claims] 1. A compound of the general formula (1) (Wherein, R represents a hydrogen atom, a halogen atom, a group selected from the group consisting of alkyl and alkoxy groups, R ¹
Is a group selected from the group consisting of a halogen atom, an alkyl group and an alkoxy group, and R ² is selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an amino group, an acylamino group and an aroylamino group Group. 2H-benzotriazole derivatives represented by the formula: 2. An ultraviolet absorber containing the 2H-benzotriazole derivative according to claim 1. 3. A weather-resistant organic polymer composition containing the 2H-benzotriazole derivative according to claim 1. 4. The following general formula (2): (Wherein R ¹ and R ² are the same as described above), and a compound represented by the following general formula (3): Wherein R is the same as defined above, wherein an aryl diisocyanate represented by the following general formula (1) is reacted in an organic solvent. (In the formula, R, R ¹ and R ² are the same as described above.) A method for producing a 2H-benzotriazole derivative represented by the formula: