JP4681820B2 - Plastic spectacle lens and manufacturing method thereof - Google Patents

Description

The present invention relates to a plastic spectacle lens and a manufacturing method thereof excellent in ultraviolet light absorbing, in particular wavelength can satisfactorily absorb long wavelength ultraviolet around 400 nm, the yellow coloration is small plastic spectacle lens and its manufacturing how It is related.

Ultraviolet rays are electromagnetic waves having a wavelength of about 200 to 400 nm, and are said to have various adverse effects on the human body. In relation to eyeglass lenses, there is an increasing demand for ultraviolet absorbing lenses from the viewpoint of protecting human eyes from ultraviolet rays.
There are various methods for imparting ultraviolet absorbing ability to a plastic spectacle lens. As the first method, Patent Documents 1 to 5 disclose 2,2′-dihydroxy-4-methoxybenzophenone, 2,2 ′. A polymerized plastic lens is described in which -dihydroxy-4-n-octoxybenzophenone or the like is used as an ultraviolet absorber, and this ultraviolet absorber is mixed with a plastic lens monomer.
The second method is the same method as dyeing of plastic lenses, in which a plastic lens is impregnated into a plastic lens by immersing the plastic lens in an aqueous solution in which an ultraviolet absorber heated to 80 to 100 ° C. is dispersed. Yes (Patent Document 6). The third method is a method of applying a substance that absorbs and / or scatters ultraviolet rays onto the surface of a plastic lens (Patent Document 7).
Among these methods, it is presumed that most of the conventional commercially available plastic spectacle lenses having a characteristic of absorbing ultraviolet rays having a wavelength up to 400 nm are manufactured by the second method.

However, the first method is a method used for the purpose of improving the light resistance of the plastic lens. In the first method, the wavelength is around 400 nm using a conventional UV absorber (2,2′-dihydroxy-4-methoxybenzophenone, 2,2′-dihydroxy-4-n-octoxybenzophenone, etc.). When manufacturing a lens that absorbs up to UV rays, a poly (thio) urethane lens known as a high refractive index lens, or a lens made of a compound having an episulfide group as a raw material has a large yellow coloration, so it does not look good In addition, since the amount of the UV absorber used is increased, the polymerization reaction is affected, and the physical properties of the obtained plastic lens tend to be deteriorated.
Even in the case of producing a plastic lens that absorbs ultraviolet light having a wavelength of up to about 400 nm by the second method, the ultraviolet absorbent to be used needs to have high ultraviolet absorbing ability and appropriate solubility in water, so that sufficient ultraviolet absorption is achieved. In many cases, a long immersion time is required even when the ability cannot be imparted or even when the ability can be imparted. Furthermore, a method using an organic solvent instead of water has been proposed. However, a plastic lens that absorbs ultraviolet rays having a wavelength up to about 400 nm manufactured by this method has a problem that yellow coloring is large.
The third method is also not an appropriate method for obtaining a plastic lens that absorbs ultraviolet rays having a wavelength of around 400 nm.

Japanese Patent Laid-Open No. 50-50049 JP 58-122501 A JP-A-2-171716 Japanese Patent Laid-Open No. 2-93422 JP-A-62-254119 JP-A-1-230003 Japanese Patent Laid-Open No. 9-265059

The present invention has been made to solve the above problems, a wavelength excellent in absorbability of the ultraviolet to near 400 nm, and an object thereof is to provide a plastic spectacle lens and a manufacturing how less coloring yellow .

As a result of intensive studies to achieve the above object, the present inventors use a combination of a (thio) urethane-based monomer and / or an episulfide-based plastic lens monomer and an ultraviolet absorber composed of a benzotriazole compound having a specific structure. As a result, the present inventors have found that a spectacle lens having excellent absorption of ultraviolet rays up to a wavelength of around 400 nm and having little yellow coloring can be obtained.
That is, this invention provides the ultraviolet absorber for plastic spectacle lenses which consists of a benzotriazole compound shown by following General formula (1).

（式中、Ｒは炭素数１〜４のアルキル基またはアルコキシ基を表し、Ｒ'は炭素数１〜１２のアルキル基またはアルコキシ基を表し、ｎは１または２の整数である。）

(Wherein R represents an alkyl group having 1 to 4 carbon atoms or an alkoxy group, R ′ represents an alkyl group having 1 to 12 carbon atoms or an alkoxy group, and n is an integer of 1 or 2).

  The present invention also relates to a plastic in which one or more benzotriazole compounds selected from the general formula (1) are added to and mixed with a (thio) urethane monomer and / or an episulfide monomer, and then the monomer is polymerized. An eyeglass lens manufacturing method and a plastic eyeglass lens manufactured by this method are provided.

The plastic spectacle lens obtained by the production method of the present invention is excellent in ultraviolet absorptivity, in particular, excellent in the absorptivity of ultraviolet rays up to a wavelength of about 400 nm and having little yellow coloring.

The ultraviolet absorber of the present invention comprises a benzotriazole compound represented by the following general formula (1).

In the general formula (1), R represents an alkyl group having 1 to 4 carbon atoms or an alkoxy group, and examples of the alkyl group include a methyl group, an ethyl group, a propyl group, and a butyl group. Examples of the alkoxy group include Includes a methoxy group, an ethoxy group, a propoxy group, and a butoxy group.
In the general formula (1), R ′ represents an alkyl group having 1 to 12 carbon atoms or an alkoxy group, and examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, Examples include alkoxy group, methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, hexyloxy group, butyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, etc. Examples include a ptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, and a dodecyloxy group.
In the general formula (1), n = 1 or an integer of 2 is represented.

  Specific examples of the benzotriazole compound represented by the general formula (1) include 5-methyl-2- (2-hydroxy-4-methylphenyl) benzotriazole and 5-methyl-2- (2-hydroxy-4). -Ethylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-4-propylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-4-butylphenyl) benzotriazole, 5-methyl-2 -(2-hydroxy-4-pentylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-4-hexylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-4-heptylphenyl) benzo Triazole, 5-methyl-2- (2-hydroxy-4-octylphenyl) benzotriazol 5-methyl-2- (2-hydroxy-4-nonylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-4-decylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy- 4-dodecylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-5-methylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-5-ethylphenyl) benzotriazole, 5-methyl- 2- (2-hydroxy-5-propylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-5-butylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-5-pentylphenyl) Benzotriazole, 5-methyl-2- (2-hydroxy-5-hexylphenyl) benzoto Azole, 5-methyl-2- (2-hydroxy-5-heptylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-5-octylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy) -5-nonylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-5-decylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-5-dodecylphenyl) benzotriazole, 5-methyl 2- (2-hydroxy-3,5-dimethylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-3,5-diethylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy- 3,5-dipropylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-3, 5-dibutylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-3,5-dipentylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-3,5-dihexylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-3,5-diheptylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-3,5-dioctylphenyl) benzotriazole, 5-methyl-2- ( 2-hydroxy-3,5-dinonylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-3,5-didecylphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-3, 5-Didodecylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-4-methylphenyl) Nzotriazole, 5-ethyl-2- (2-hydroxy-4-ethylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-4-propylphenyl) benzotriazole, 5-ethyl-2- (2 -Hydroxy-4-butylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-4-pentylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-4-hexylphenyl) benzotriazole, 5 -Ethyl-2- (2-hydroxy-4-heptylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-4-octylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-4-) Nonylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-4-decyl) Enyl) benzotriazole, 5-ethyl-2- (2-hydroxy-4-dodecylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-5-methylphenyl) benzotriazole, 5-ethyl-2- ( 2-hydroxy-5-ethylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-5-propylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-5-butylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-5-pentylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-5-hexylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-5) -Heptylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-5) -Octylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-5-nonylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-5-decylphenyl) benzotriazole, 5-ethyl-2 -(2-hydroxy-5-dodecylphenyl) benzotriazole,

5-ethyl-2- (2-hydroxy-3,5-dimethylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-3,5-diethylphenyl) benzotriazole, 5-ethyl-2- (2 -Hydroxy-3,5-dipropylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-3,5-dibutylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-3,5- Dipentylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-3,5-dihexylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-3,5-diheptylphenyl) benzotriazole, 5 -Ethyl-2- (2-hydroxy-3,5-dioctylphenyl) benzotriazole, 5-ethyl-2- 2-hydroxy-3,5-dinonylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-3,5-didecylphenyl) benzotriazole, 5-ethyl-2- (2-hydroxy-3, 5-Didodecylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-4-methylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-4-ethylphenyl) benzotriazole, 5-propyl -2- (2-hydroxy-4-propylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-4-butylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-4-pentylphenyl) ) Benzotriazole, 5-propyl-2- (2-hydroxy-4-hexylphenyl) Benzotriazole, 5-propyl-2- (2-hydroxy-4-heptylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-4-octylphenyl) benzotriazole, 5-propyl-2- (2- Hydroxy-4-nonylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-4-decylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-4-dodecylphenyl) benzotriazole, 5- Propyl-2- (2-hydroxy-5-methylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-5-ethylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-5-propyl) Phenyl) benzotriazole, 5-propyl-2- (2-hydro) Xyl-5-butylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-5-pentylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-5-hexylphenyl) benzotriazole, 5- Propyl-2- (2-hydroxy-5-heptylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-5-octylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-5-nonyl) Phenyl) benzotriazole, 5-propyl-2- (2-hydroxy-5-decylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-5-dodecylphenyl) benzotriazole, 5-propyl-2- ( 2-Hydroxy-3,5-dimethylphenyl) benzotriazol 5-propyl-2- (2-hydroxy-3,5-diethylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-3,5-dipropylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-3,5-dibutylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-3,5-dipentylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-3,5 -Dihexylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-3,5-diheptylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-3,5-dioctylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-3,5-dinonylphenyl) benzotriazol 5-propyl-2- (2-hydroxy-3,5-didecylphenyl) benzotriazole, 5-propyl-2- (2-hydroxy-3,5-didodecylphenyl) benzotriazole, 5-butyl-2 -(2-hydroxy-4-methylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-4-ethylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-4-propylphenyl) benzo Triazole, 5-butyl-2- (2-hydroxy-4-butylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-4-pentylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy) -4-hexylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-4-heptyl) Enyl) benzotriazole, 5-butyl-2- (2-hydroxy-4-octylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-4-nonylphenyl) benzotriazole, 5-butyl-2- ( 2-hydroxy-4-decylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-4-dodecylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-5-methylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-5-ethylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-5-propylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-5) -Butylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-5-pe) Tilphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-5-hexylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-5-heptylphenyl) benzotriazole, 5-butyl-2- ( 2-hydroxy-5-octylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-5-nonylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-5-decylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-5-dodecylphenyl) benzotriazole,

5-butyl-2- (2-hydroxy-3,5-dimethylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-3,5-diethylphenyl) benzotriazole, 5-butyl-2- (2 -Hydroxy-3,5-dipropylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-3,5-dibutylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-3,5- Dipentylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-3,5-dihexylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-3,5-diheptylphenyl) benzotriazole, 5 -Butyl-2- (2-hydroxy-3,5-dioctylphenyl) benzotriazole, 5-butyl-2- 2-hydroxy-3,5-dinonylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-3,5-didecylphenyl) benzotriazole, 5-butyl-2- (2-hydroxy-3, 5-didodecylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4-methylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4-ethylphenyl) benzotriazole, 5-methoxy 2- (2-hydroxy-4-propylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4-butylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4-pentylphenyl) ) Benzotriazole, 5-methoxy-2- (2-hydroxy-4-hexylphenyl) Benzotriazole, 5-methoxy-2- (2-hydroxy-4-heptylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4-octylphenyl) benzotriazole, 5-methoxy-2- (2- Hydroxy-4-nonylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4-decylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4-dodecylphenyl) benzotriazole, 5- Methoxy-2- (2-hydroxy-5-methylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-5-ethylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-5-propyl) Phenyl) benzotriazole, 5-methoxy-2- (2-hydro) Xyl-5-butylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-5-pentylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-5-hexylphenyl) benzotriazole, 5- Methoxy-2- (2-hydroxy-5-heptylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-5-octylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-5-nonyl) Phenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-5-decylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-5-dodecylphenyl) benzotriazole, 5-methoxy-2- ( 2-Hydroxy-3,5-dimethylphenyl) benzotriazol 5-methoxy-2- (2-hydroxy-3,5-diethylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-3,5-dipropylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-3,5-dibutylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-3,5-dipentylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-3,5 -Dihexylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-3,5-diheptylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-3,5-dioctylphenyl) benzotriazole, 5-Methoxy-2- (2-hydroxy-3,5-dinonylphenyl) benzotriazol 5-methoxy-2- (2-hydroxy-3,5-didecylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-3,5-didodecylphenyl) benzotriazole, 5-ethoxy-2 -(2-hydroxy-4-methylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-ethylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-propylphenyl) benzo Triazole, 5-ethoxy-2- (2-hydroxy-4-butylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-pentylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy -4-hexylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-) 4-heptylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-octylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-nonylphenyl) benzotriazole, 5-ethoxy- 2- (2-hydroxy-4-decylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-dodecylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-5-methylphenyl) Benzotriazole, 5-ethoxy-2- (2-hydroxy-5-ethylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-5-propylphenyl) benzotriazole, 5-ethoxy-2- (2- Hydroxy-5-butylphenyl) benzotriazole, 5-ethoxy -2- (2-hydroxy-5-pentylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-5-hexylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-5-heptylphenyl) ) Benzotriazole, 5-ethoxy-2- (2-hydroxy-5-octylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-5-nonylphenyl) benzotriazole, 5-ethoxy-2- (2 -Hydroxy-5-decylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-5-dodecylphenyl) benzotriazole,

5-ethoxy-2- (2-hydroxy-3,5-dimethylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-3,5-diethylphenyl) benzotriazole, 5-ethoxy-2- (2 -Hydroxy-3,5-dipropylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-3,5-dibutylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-3,5- Dipentylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-3,5-dihexylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-3,5-diheptylphenyl) benzotriazole, 5 -Ethoxy-2- (2-hydroxy-3,5-dioctylphenyl) benzotriazole, -Ethoxy-2- (2-hydroxy-3,5-dinonylphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-3,5-didecylphenyl) benzotriazole, 5-ethoxy-2- ( 2-hydroxy-3,5-didodecylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-methylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-ethylphenyl) Benzotriazole, 5-propoxy-2- (2-hydroxy-4-propylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-butylphenyl) benzotriazole, 5-propoxy-2- (2- Hydroxy-4-pentylphenyl) benzotriazole, 5-propoxy-2- (2 Hydroxy-4-hexylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-heptylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-octylphenyl) benzotriazole, 5- Propoxy-2- (2-hydroxy-4-nonylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-decylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-dodecyl) Phenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-5-methylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-5-ethylphenyl) benzotriazole, 5-propoxy-2- ( 2-hydroxy-5-propylphenyl) Benzotriazole, 5-propoxy-2- (2-hydroxy-5-butylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-5-pentylphenyl) benzotriazole, 5-propoxy-2- (2- Hydroxy-5-hexylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-5-heptylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-5-octylphenyl) benzotriazole, 5- Propoxy-2- (2-hydroxy-5-nonylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-5-decylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-5-dodecyl) Phenyl) benzotriazole, 5-propoxy 2- (2-hydroxy-3,5-dimethylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-3,5-diethylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy- 3,5-dipropylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-3,5-dibutylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-3,5-dipentylphenyl) Benzotriazole, 5-propoxy-2- (2-hydroxy-3,5-dihexylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-3,5-diheptylphenyl) benzotriazole, 5-propoxy- 2- (2-Hydroxy-3,5-dioctylphenyl) benzotriazol 5-propoxy-2- (2-hydroxy-3,5-dinonylphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-3,5-didecylphenyl) benzotriazole, 5-propoxy-2 -(2-hydroxy-3,5-didodecylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-methylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-ethyl) Phenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-propylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-butylphenyl) benzotriazole, 5-butoxy-2- ( 2-hydroxy-4-pentylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy) Droxy-4-hexylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-heptylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-octylphenyl) benzotriazole, 5- Butoxy-2- (2-hydroxy-4-nonylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-decylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-dodecyl) Phenyl) benzotriazole,

5-butoxy-2- (2-hydroxy-5-methylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-5-ethylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-5) -Propylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-5-butylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-5-pentylphenyl) benzotriazole, 5-butoxy-2 -(2-hydroxy-5-hexylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-5-heptylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-5-octylphenyl) benzo Triazole, 5-butoxy-2- (2-hydroxy-5-nonyl) Nyl) benzotriazole, 5-butoxy-2- (2-hydroxy-5-decylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-5-dodecylphenyl) benzotriazole, 5-butoxy-2- ( 2-hydroxy-3,5-dimethylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-3,5-diethylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-3,5- Dipropylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-3,5-dibutylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-3,5-dipentylphenyl) benzotriazole, 5 -Butoxy-2- (2-hydroxy-3,5-dihexylphenyl) benzo Riazole, 5-butoxy-2- (2-hydroxy-3,5-diheptylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-3,5-dioctylphenyl) benzotriazole, 5-butoxy-2 -(2-hydroxy-3,5-dinonylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-3,5-didecylphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy- 3,5-didodecylphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4-methoxyphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4-ethoxyphenyl) benzotriazole, 5 -Methoxy-2- (2-hydroxy-4-propoxyphenyl) benzotriazole, 5 -Methoxy-2- (2-hydroxy-4-butoxyphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4-pentyloxyphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4) -Hexyloxyphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4-heptyloxyphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4-octyloxyphenyl) benzotriazole, 5- Methoxy-2- (2-hydroxy-4-nonyloxyphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4-decyloxyphenyl) benzotriazole, 5-methoxy-2- (2-hydroxy-4) -Dodecyloxyphenyl) benzotriazole, 5-d Xyl-2- (2-hydroxy-4-methoxyphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-ethoxyphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-propoxy) Phenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-butoxyphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-pentyloxyphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-hexyloxyphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-heptyloxyphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-octyloxyphenyl) ) Benzotriazole, 5-ethoxy-2- (2 Hydroxy-4-nonyloxyphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-decyloxyphenyl) benzotriazole, 5-ethoxy-2- (2-hydroxy-4-dodecyloxyphenyl) benzotriazole 5-propoxy-2- (2-hydroxy-4-methoxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-ethoxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy- 4-propoxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-butoxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-pentyloxyphenyl) benzotriazole, 5-propoxy -2- (2-hydroxy Ci-4-hexyloxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-heptyloxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-octyloxyphenyl) benzotriazole 5-propoxy-2- (2-hydroxy-4-nonyloxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-decyloxyphenyl) benzotriazole, 5-propoxy-2- (2- Hydroxy-4-dodecyloxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-methoxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-ethoxyphenyl) benzotriazole, 5 -Propoxy-2- (2-G Roxy-4-propoxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-butoxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-pentyloxyphenyl) benzotriazole, 5 -Propoxy-2- (2-hydroxy-4-hexyloxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-heptyloxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy- 4-octyloxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-nonyloxyphenyl) benzotriazole, 5-propoxy-2- (2-hydroxy-4-decyloxyphenyl) benzotriazole, 5 -Propoxy-2- 2-hydroxy-4-dodecyloxyphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-methoxyphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-ethoxyphenyl) benzotriazole 5-butoxy-2- (2-hydroxy-4-propoxyphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-butoxyphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy- 4-pentyloxyphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-hexyloxyphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-heptyloxyphenyl) benzotriazole, 5 -Butoxy-2- (2-hydroxy- 4-octyloxyphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-nonyloxyphenyl) benzotriazole, 5-butoxy-2- (2-hydroxy-4-decyloxyphenyl) benzotriazole, 5 -Butoxy-2- (2-hydroxy-4-dodecyloxyphenyl) benzotriazole and the like.

  Among these, 5-methyl-2- (2-hydroxy-4-decyloxyphenyl) benzotriazole, 5-methyl-2- (2-hydroxy-4-octyloxyphenyl) benzotriazole, 5-ethoxy-2- (2-Hydroxy-4-octyloxyphenyl) benzotriazole and 5-methyl-2- (2-hydroxy-4-dodecyloxyphenyl) benzotriazole are preferred.

In the method for producing a plastic spectacle lens of the present invention, one or more benzotriazole compounds selected from the general formula (1) are added to and mixed with a (thio) urethane monomer and / or an episulfide monomer, This is a method for polymerizing monomers, and the plastic spectacle lens of the present invention is produced by the above method.
In the present invention, the amount of the benzotriazole compound added varies depending on the type of (thio) urethane-based monomer and / or episulfide-based monomer that is a plastic spectacle lens raw material monomer, desired ultraviolet absorption characteristics, etc. It is preferably used in the range of 0.03 to 10 parts by weight, more preferably in the range of 0.03 to 6 parts by weight, and particularly preferably in the range of 0.05 to 2 parts by weight with respect to 100 parts by weight of the monomer. It is.

  In the present invention, the (thio) urethane-based monomer means a thiourethane-based monomer and a urethane-based monomer, and is a raw material monomer for producing a polythiourethane lens or a polyurethane lens. Can include those obtained from a combination of a polyisocyanate compound and a polythiol compound, and a combination of a polyisocyanate compound and a polyol compound.

  The polyisocyanate compound is not particularly limited, and specific examples thereof include hydrogenated 2,6-tolylene diisocyanate, hydrogenated meta and paraphenylene diisocyanate, and hydrogenated 2,4-tolylene diisocyanate. , Alicyclic isocyanate compounds such as hydrogenated diphenylmethane diisocyanate, hydrogenated metaxylylene diisocyanate, hydrogenated paraxylylene diisocyanate, isophorone diisocyanate; meta and paraphenylene diisocyanate, 2,6-tri Range isocyanate, 2,4-tolylene diisocyanate, 4,4′-diphenylmethane diisocyanate, meta and paraxylylene diisocyanate, meta and paratetramethylxylylene diisocyanate, 2,6-naphthalene diisocyanate, 1,5-naphthalene diiso Anato, hexamethylene diisocyanate, octamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate burette reaction product, hexamethylene diisocyanate Isocyanate compounds having no alicyclic or aromatic ring such as trimer, lysine diisocyanate, lysine triisocyanate, 1,6,11-undecane triisocyanate, triphenylmethane triisocyanate; diphenyl disulfide- 4,4'-diisocyanate, 2,2'-dimethyldiphenyl disulfide-5,5'-diisocyanate, 3,3'-dimethyldiphenyl disulfide-5,5'-diisocyanate, 3,3'- Dimethyldiphenyl disulfi 6,6′-diisocyanate, 4,4′-dimethyldiphenyl disulfide-5,5′-diisocyanate, 3,3′-dimethoxydiphenyl disulfide-4,4′-diisocyanate, 4,4 '-Dimethoxydiphenyl disulfide-3,3'-diisocyanate, diphenylsulfone-4,4'-diisocyanate, diphenylsulfone-3,3'-diisocyanate, benzylidenesulfone-4,4'-diisocyanate Diphenylmethanesulfone-4,4′-diisocyanate, 4-methyldiphenylmethanesulfone-2,4′-diisocyanate, 4,4′-dimethoxydiphenylsulfone-3,3′-diisocyanate, 3,3 ′ -Dimethoxy-4,4'-diisocyanatodibenzylsulfone, 4,4'-dimethyldiphenylsulfone -3,3'-diisocyanate, 4,4'-di-tert-butyldiphenylsulfone-3,3'-diisocyanate, 4,4'-dimethoxybenzeneethylenedisulfone-3,3'-diisocyanate 4,4′-dichlorodiphenylsulfone-3,3′-diisocyanate, 4-methyl-3-isocyanatobenzenesulfonyl-4′-isocyanatophenol ester, 4-methoxy-3-isocyanatobenzenesulfonyl-4 '-Isocyanatophenol ester, 4-methyl-3-isocyanatobenzenesulfonylanilide-3'-methyl-4'-isocyanate, dibenzenesulfonyl-ethylenediamine-4,4'-diisocyanate, 4,4'- Dimethoxybenzenesulfonyl-ethylenediamine-3,3′-diisocyanate, 4- Tyl-3-isocyanatobenzenesulfonylanilide-4-methyl-3'-isocyanate, thiophene-2,5-diisocyanate, thiophene-2,5-diisocyanatomethyl, 1,4-dithiane-2,5 -Diisocyanate, 1,4-dithian-2,5-diisocyanatomethyl, 1,4-dithian-2,3-diisocyanatomethyl, 1,4-dithian-2-isocyanatomethyl-5-isocyanate Natopropyl, 1,3-dithiolane-4,5-diisocyanate, 1,3-dithiolane-4,5-diisocyanatomethyl, 1,3-dithiolane-2-methyl-4,5-diisocyanatomethyl 1,3-dithiolane-2,2-diisocyanatoethyl, tetrahydrothiophene-2,5-diisocyanate, tetrahydrothiophene-2,5-dii Examples thereof include sulfur-containing isocyanate compounds such as soocyanatomethyl, tetrahydrothiophene-2,5-diisocyanatoethyl, and tetrahydrothiophene-3,4-diisocyanatomethyl.

  Examples of the polythiol compound include methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, 1,6-hexanedithiol. 1,2,3-propanetrithiol, tetrakis (mercaptomethyl) methane, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxy Butane-1,2-dithiol, 2-methylcyclohexane-2,3-dithiol, 1,1-bis (mercaptomethyl) cyclohexane, bis (2-mercaptoethyl ester) thiomalate, 2,3-dimercaptosuccinic acid ( 2-mercaptoethyl ester), 2,3-dimethyl Capto-1-propanol (2-mercaptoacetate), 2,3-dimercapto-1-propanol (3-mercaptoacetate), diethylene glycol bis (2-mercaptoacetate), diethylene glycol bis (3-mercaptopropionate), 1, 2-dimercaptopropyl methyl ether, 2,3-dimercaptopropyl methyl ether, 2,2-bis (mercaptomethyl) -1,3-propanedithiol, bis (2-mercaptoethyl) ether, ethylene glycol bis (2- Mercaptoacetate), ethylene glycol bis (3-mercaptopropionate), trimethylolpropane tris (2-mercaptoacetate), trimethylolpropane tris (3-mercaptopropionate), pentaerythri Aliphatic thiols such as 1,4-dimercaptobenzene, 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane; 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis (mercaptomethyl) benzene, 1,3-bis (mercaptomethyl) benzene, 1,4-bis (mercaptomethyl) benzene, 1,3-bis (mercaptoethyl) benzene, 1,4-bis (mercaptoethyl) benzene, 1,2-bis (mercaptomethoxy) benzene, 1,3-bis (mercaptomethoxy) benzene, 1,4-bis ( Mercaptomethoxy) benzene, 1,2-bis (mercaptoethoxy) benzene 1,3-bis (mercaptoethoxy) benzene, 1,4-bis (mercaptoethoxy) benzene, 1,2,3-trimercaptobenzene, 1,2,4-trimercaptobenzene, 1,3,5-tri Mercaptobenzene, 1,2,3-tris (mercaptomethyl) benzene, 1,2,4-tris (mercaptomethyl) benzene, 1,3,5-tris (mercaptomethyl) benzene, 1,2,3-tris ( Mercaptoethyl) benzene, 1,2,4-tris (mercaptoethyl) benzene, 1,3,5-tris (mercaptoethyl) benzene, 1,2,3-tris (mercaptomethoxy) benzene, 1,2,4- Tris (mercaptomethoxy) benzene, 1,3,5-tris (mercaptomethoxy) benzene, 1,2,3-tris (mercapto Toxi) benzene, 1,2,4-tris (mercaptoethoxy) benzene, 1,3,5-tris (mercaptoethoxy) benzene, 1,2,3,4-tetramercaptobenzene, 1,2,3,5- Tetramercaptobenzene, 1,2,4,5-tetramercaptobenzene, 1,2,3,4-tetrakis (mercaptomethyl) benzene, 1,2,3,5-tetrakis (mercaptomethyl) benzene, 1,2, 4,5-tetrakis (mercaptomethyl) benzene, 1,2,3,4-tetrakis (mercaptoethyl) benzene, 1,2,3,5-tetrakis (mercaptoethyl) benzene, 1,2,4,5-tetrakis (Mercaptoethyl) benzene, 1,2,3,4-tetrakis (mercaptoethyl) benzene, 1,2,3,5-tetrakis ( Lucaptomethoxy) benzene, 1,2,4,5-tetrakis (mercaptomethoxy) benzene, 1,2,3,4-tetrakis (mercaptoethoxy) benzene, 1,2,3,5-tetrakis (mercaptoethoxy) benzene 1,2,4,5-tetrakis (mercaptoethoxy) benzene, 2,2′-dimercaptobiphenyl, 4,4′-dimercaptobiphenyl, 4,4′-dimercaptobibenzyl, 2,5-toluenedithiol 3,4-toluenedithiol, 1,4-naphthalenedithiol, 1,5-naphthalenedithiol, 2,6-naphthalenedithiol, 2,7-naphthalenedithiol, 2,4-dimethylbenzene-1,3-dithiol, 4, , 5-Dimethylbenzene-1,3-dithiol, 9,10-anthracene dimethanethiol 1,3-di (p-methoxyphenyl) propane-2,2-dithiol, 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, 2,4-di (p-mercapto Aromatic thiols such as phenyl) pentane; 2,5-dichlorobenzene-1,3-dithiol, 1,3-di (p-chlorophenyl) propane-2,2-dithiol, 3,4,5-tribromo-1, 1,2-bis (mercapto), halogen-substituted aromatic thiols such as 2-dimercaptobenzene, chlorine-substituted products such as 2,3,4,6-tetrachloro-1,5-bis (mercaptomethyl) benzene, and bromine-substituted products; Methylthio) benzene, 1,3-bis (mercaptomethylthio) benzene, 1,4-bis (mercaptomethylthio) benzene, 1,2-bis (mercapto) Tilthio) benzene, 1,3-bis (mercaptoethylthio) benzene, 1,4-bis (mercaptoethylthio) benzene, 1,2,3-tris (mercaptomethylthio) benzene, 1,2,4-tris (mercapto) Methylthio) benzene, 1,3,5-tris (mercaptomethylthio) benzene, 1,2,3-tris (mercaptoethylthio) benzene, 1,2,4-tris (mercaptoethylthio) benzene, 1,3,5 Tris (mercaptoethylthio) benzene, 1,2,3,4-tetrakis (mercaptomethylthio) benzene, 1,2,3,5-tetrakis (mercaptomethylthio) benzene, 1,2,4,5-tetrakis (mercapto Methylthio) benzene, 1,2,3,4-tetrakis (mercaptoethylthio) benzene, 1 , 2,3,5-tetrakis (mercaptoethylthio) benzene, 1,2,4,5-tetrakis (mercaptoethylthio) benzene, etc., and aromatic compounds containing sulfur atoms in addition to mercapto groups such as these alkylated products Group thiols: bis (mercaptomethyl) sulfide, bis (mercaptoethyl) sulfide, bis (mercaptopropyl) sulfide, bis (mercaptomethylthio) methane, bis (2-mercaptoethylthio) methane, bis (3-mercaptopropylthio) methane 1,2-bis (mercaptomethylthio) ethane, 1,2-bis (2-mercaptoethylthio) ethane, 1,2-bis (3-mercaptopropylthio) ethane, 1,3-bis (mercaptomethylthio) propane 1,3-bis (2-mercaptoethylthio) propane 1,3-bis (3-mercaptopropylthio) propane, 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane, 2-mercaptoethylthio-1,3-propanedithiol, 1,2,3 -Tris (mercaptomethylthio) propane, 1,2,3-tris (2-mercaptoethylthio) propane, 1,2,3-tris (3-mercaptopropylthio) propane, tetrakis (mercaptomethylthiomethyl) methane, tetrakis ( 2-mercaptoethylthiomethyl) methane, tetrakis (3-mercaptopropylthiomethyl) methane, bis (2,3-dimercaptopropyl) sulfide, 2,5-dimercapto-1,4-dithiane, bis (mercaptomethyl) disulfide Bis (mercaptoethyl) disulfide, bis (me Captopropyl) disulfide and the like, and esters of these thioglycolic acid and mercaptopropionic acid, hydroxymethyl sulfide bis (2-mercaptoacetate), hydroxymethyl sulfide bis (3-mercaptopropionate), hydroxyethyl sulfide bis (2- Mercaptoacetate), hydroxyethyl sulfide bis (3-mercaptopropionate), hydroxypropyl sulfide bis (2-mercaptoacetate), hydroxypropyl sulfide bis (3-mercaptopropionate), hydroxymethyl disulfide bis (2-mercaptoacetate) ), Hydroxymethyl disulfide bis (3-mercaptopropionate), hydroxyethyl disulfide bis (2-mercaptoacetate), Droxyethyl disulfide bis (3-mercaptopropionate), hydroxypropyl disulfide bis (2-mercaptoacetate), hydroxypropyl disulfide bis (3-mercaptopropionate), 2-mercaptoethyl ether bis (2-mercaptoacetate) 2-mercaptoethyl ether bis (3-mercaptopropionate), 1,4-dithian-2,5-diol bis (2-mercaptoacetate), 1,4-dithian-2,5-diol bis (3-mercaptopro Pionate), thioglycolic acid (2-mercaptoethyl ester), thiodipropionic acid bis (2-mercaptoethyl ester), 4,4′-thiodibutyric acid bis (2-mercaptoethyl ester), dithiodiglycolic acid bis ( 2-mel Ptoethyl ester), dithiodipropionic acid bis (2-mercaptoethyl ester), 4,4′-dithiodibutyric acid bis (2-mercaptoethyl ester), thiodiglycolic acid bis (2,3-dimercaptopropyl ester) Bis (2,3-dimercaptopropyl ester) thiodipropionate, bis (2,3-dimercaptopropyl ester) dithiodiglycolate, bis (2,3-dimercaptopropyl ester) dithiodipropionate, 4 -Mercaptomethyl-3,6-dithiaoctane-1,8-dithiol, bis (mercaptomethyl) -3,6,9-trithia-1,11-undecanedithiol, bis (1,3-dimercapto-2-propyl) sulfide Aliphatic thiols containing sulfur atoms in addition to mercapto groups such as 3,4- Offenedithiol, tetrahydrothiophene-2,5-dimercaptomethyl, 2,5-dimercapto-1,3,4-thiadiazole, 2,5-dimercapto-1,4-dithiane, 2,5-dimercaptomethyl-1, Examples include heterocyclic compounds containing a sulfur atom in addition to a mercapto group such as 4-dithiane. In the present invention, among these, from the viewpoint of providing a plastic spectacle lens having a high refractive index, an isocyanate compound containing a sulfur atom and a polythiol compound containing a sulfur atom in addition to a mercapto group (thiol group) are preferable.

  Examples of the polyol compound include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, neopentyl glycol, glycerin, trimethylolethane, trimethylolpropane, butanetriol, 1,2-methylglucoside, pentaerythritol. , Dipentaerythritol, tripentaerythritol, triethylene glycol, polyethylene glycol, tris (2-hydroxyethyl) isocyanurate, cyclobutanediol, cyclopentanediol, cyclohexanediol, cycloheptanediol, cyclooctanediol, bicyclo [4.3. 0] -nonanediol, dicyclohexanediol, tricyclo [5.3.1.1] dodecandio , Aliphatic polyols such as spiro [3.4] octanediol, butylcyclohexanediol; dihydroxynaphthalene, trihydroxynaphthalene, tetrahydroxynaphthalene, dihydroxybenzene, benzenetriol, trihydroxyphenanthrene, bisphenol A, bisphenol F, xylylene glycol , Aromatic polyols such as tetrabromobisphenol A and addition reaction products of these with alkylene oxides such as ethylene oxide and propylene oxide; bis- [4- (hydroxyethoxy) phenyl] sulfide, bis- [4- (2- Hydroxypropoxy) phenyl] sulfide, bis- [4- (2,3-dihydroxypropoxy) phenyl] sulfide, bis- [4- (4-hydroxycyclohexane) Siloxy) phenyl] sulfide, bis- [2-methyl-4- (hydroxyethoxy) -6-butylphenyl] sulfide and these compounds were added with an average of 3 molecules or less of ethylene oxide and / or propylene oxide per hydroxyl group. Compound; di- (2-hydroxyethyl) sulfide, 1,2-bis- (2-hydroxyethyl mercapto) ethane, bis (2-hydroxyethyl) disulfide, 1,4-dithian-2,5-diol, bis ( 2,3-dihydroxypropyl) sulfide, tetrakis (4-hydroxy-2-thiabutyl) methane, bis (4-hydroxyphenyl) sulfone (trade name bisphenol S), tetrabromobisphenol S, tetramethylbisphenol S, 4,4 ′ -Thiobis (6-tert-butyl 3-methylphenol), 1,3-bis (2-hydroxyethyl thio ethyl) - such polyols containing a sulfur atom, such as cyclohexane. In the present invention, among these, a polyol compound containing a sulfur atom is preferred from the viewpoint of providing a high refractive index plastic spectacle lens.

  Further, the (thio) urethane-based monomer has been conventionally known, and specific publications that disclose this monomer include, for example, JP-A-58-127914, JP-A-57-136601, JP-A-01-163012, JP-A-03-236386, JP-A-03-281313, JP-A-4-159275, JP-A-05-148340, JP-A-06- No. 065193, JP-A-06-256459, JP-A-06-313801, JP-A-06-192250, JP-A-07-063902, JP-A-07-104101, JP-A-07-118263. Japanese Patent Laid-Open No. 07-118390, Japanese Patent Laid-Open No. 07-316250, Japanese Patent Laid-Open No. 60-199016 JP, 60-217229, JP 62-236818, JP 62-255901, JP 62-267316, JP 63-130615, JP JP-A-63-130614, JP-A-63-046213, JP-A-63-245421, JP-A-63-265201, JP-A-01-090167, JP-A-01-090168, Japanese Unexamined Patent Publication Nos. 01-090169, 01-090170, 01-096208, 01-152019, 01-045611, 01-213601, 01 JP-A-0202622, JP-A-01-054021, JP-A-01-31118, JP-A-01-29520. No. 1, No. 01-302202, No. 02-153302, No. 01-295202, No. 02-802, No. 02-036216, No. 02-058517. JP, JP 02-167330, JP 02-270859, JP 03-84031, JP 03-084021, JP 03-124722, JP 04-78801, JP 04-117353 A, JP 04-117354 A, JP 04-256558 A, JP 05-78441 A, JP 05-273401 A, JP 05-093801 A, JP No. 05-080201, JP-A 05-297201, JP-A 05-320301 JP-A-05-208950, JP-A-06-072989, JP-A-06-256342, JP-A-06-122748, JP-A-07-165859, JP-A-07-118357, JP 07-242722, JP 07-247335, JP 07-252341, JP 08-73732, JP 08-092345, JP 07-228659, JP 08 No. 3267, JP 07-252207 A, JP 07-324118 A, JP 09-208651 A, and the like. The polyisocyanate compounds, polyol compounds, and polythiol compounds disclosed in these publications correspond to the (thio) urethane-based monomer referred to in the present invention. Furthermore, in order to improve the physical properties such as heat resistance and refractive index, these plastics (thio) urethane monomers may be added with other plastic lens monomers such as disulfide ethylene glycol allyl carbonate in addition to episulfide monomers described later. It is also possible to add.

  In the present invention, the episulfide monomer is also referred to as an epithio monomer and refers to a monomer having an episulfide group (epithio group) or a mixed monomer including the monomer. Here, specific examples of the monomer having an episulfide group include 1,3 and 1,4-bis (β-epithiopropylthio) cyclohexane, 1,3 and 1,4-bis (β-epithiopropylthiomethyl). ) Cyclohexane, bis [4- (β-epithiopropylthio) cyclohexyl] methane, 2,2-bis [4- (β-epithiopropylthio) cyclohexyl] propane, bis [4- (β-epithiopropylthio) ) Cyclohexyl] Episulfide compounds having an alicyclic skeleton such as sulfide; 1,3 and 1,4-bis (β-epithiopropylthio) benzene, 1,3 and 1,4-bis (β-epithiopropylthio) Methyl) benzene, bis [4- (β-epithiopropylthio) phenyl] methane, 2,2-bis [4- (β-epithiopropylthio) pheny ] Propane, bis [4- (β-epithiopropylthio) phenyl] sulfide, bis [4- (β-epithiopropylthio) phenyl] sulfine, 4,4-bis (β-epithiopropylthio) biphenyl, etc. Episulfide compound having an aromatic skeleton of 2,5-bis (β-epithiopropylthiomethyl) -1,4-dithiane, 2,5-bis (β-epithiopropylthioethylthiomethyl) -1,4 -Dithiane ring such as dithiane, 2,5-bis (β-epithiopropylthioethyl) -1,4-dithiane, 2,3,5-tri (β-epithiopropylthioethyl) -1,4-dithiane Episulfide compound having a skeleton; 2- (2-β-epithiopropylthioethylthio) -1,3-bis (β-epithiopropylthio) propane, 1,2-bis [(2-β- Epithiopropylthioethyl) thio] -3- (β-epithiopropylthio) propane, tetrakis (β-epithiopropylthiomethyl) methane, 1,1,1-tris (β-epithiopropylthiomethyl) propane And episulfide compounds having an aliphatic skeleton such as bis- (β-epithiopropyl) sulfide. In the present invention, among these, an episulfide compound having a high sulfur atom content is preferable from the viewpoint of providing a plastic eyeglass lens having a high refractive index.

  Episulfide monomers have been conventionally known, and specific examples of publications disclosing such episulfide monomers include JP 09-071580 A, JP 09-110979 A, and JP 09-255781 A. JP-A-03-08320, JP-A-11-140070, JP-A-11-183702, JP-A-11-189582, JP-A-11-180977, JP-T-01-810575. Etc. It goes without saying that the episulfide monomers disclosed in these publications correspond to the episulfide monomers in the present invention. Of course, in order to improve lens properties such as impact resistance and processability, it is possible to add other plastic lens monomers such as the (thio) urethane-based monomer described above.

In the present invention, as an optional component, a diethylene glycol bisallyl carbonate monomer can be added to the (thio) urethane monomer and / or episulfide monomer.
Examples of the diethylene glycol bisallyl carbonate monomer include diethylene glycol bisallyl carbonate alone and a mixed monomer of a monomer copolymerizable with diethylene glycol bisallyl carbonate. Specific examples of the copolymerizable monomer include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene, chlorostyrene, chloromethylstyrene, and divinylbenzene; methyl (meth) acrylate, n-butyl (meta ) Acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, 3-chloro-2-hydroxypropyl (meth) ) Acrylates, stearyl (meth) acrylates, lauryl (meth) acrylates, phenyl (meth) acrylates, glycidyl (meth) acrylates, mono (meth) acrylates such as benzyl methacrylate 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 3-phenoxy-2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) Mono (meth) acrylates having a hydroxy group such as acrylate; ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,3- Butylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, 2-hydride Roxy-1,3-di (meth) acryloxypropane, 2,2-bis [4-((meth) acryloxyethoxy) phenyl] propane, 2,2-bis [4-((meth) acryloxydiethoxy) Di (meth) acrylates such as phenyl] propane and 2,2-bis [4-((meth) acryloxy polyethoxy) phenyl] propane; tri (meth) acrylates such as trimethylolpropane trimethacrylate and tetramethylolmethane trimethacrylate Tetra (meth) acrylates such as tetramethylolmethane tetra (meth) acrylate [wherein (meth) acrylate means methacrylate or acrylate]; diallyl phthalate, diallyl isophthalate, diallyl terephthalate, etc. Is mentioned. In the present invention, among these, a monomer having an aromatic ring is preferable from the viewpoint of providing a high refractive index plastic spectacle lens. Copolymers of diethylene glycol bisallyl carbonate and other monomers are known, and examples thereof include JP-A-54-41965, JP-A-51-125487, and JP-T-01-503809. Examples include the disclosed copolymers. Needless to say, the mixture of diethylene glycol bisallyl carbonate and the monomer copolymerizable with diethylene glycol bisallyl carbonate described in these publications corresponds to the diethylene glycol bisallyl carbonate monomer in the present invention.

In addition, there are various properties of the plastic spectacle lens of the present invention, and it may be appropriately selected depending on the purpose of use. For example, the following (i) to (ii) are preferable. .
(I) YI (yellowness) at the lens center when the center thickness of the lens is 2.0 mm is in the range of 0.7 to 1.8, and the light transmittance at a wavelength of 400 nm is 40% or less. .
(Ii) YI (yellowness) at the center of the lens when the center thickness of the lens is 2.0 mm is in the range of 0.7 to 1.7, the light transmittance at a wavelength of 395 nm is 6% or less, the wavelength The light transmittance at 400 nm is 7 to 20%, and the light transmittance at a wavelength of 405 nm is 50% or more.

In the plastic spectacle lens of the present invention, when a thiourethane monomer is used as a main component, when the weight of the whole plastic spectacle lens raw material monomer is 1, the polyisocyanate compound and the polythiol compound that become the lens raw material monomer The polymerization is preferably performed from raw materials having a total weight of 0.6 or more.
In addition, when an episulfide monomer is used as a main component, a raw material in which the amount of the compound having an episulfide group that becomes a plastic spectacle lens raw material monomer is 0.6 or more when the weight of the whole lens raw material monomer is 1 It is preferable to be polymerized from.

  The plastic spectacle lens of the present invention can be obtained by polymerizing a plastic spectacle lens raw material monomer to which one or more benzotriazole compounds selected from the general formula (1) are added and mixed. The method for polymerizing the plastic spectacle lens raw material monomer is not particularly limited, but usually cast polymerization is employed. That is, after mixing one or more kinds of benzotriazole compounds selected from the general formula (1) and the above-mentioned plastic spectacle lens raw material monomer, this mixed solution is injected into a lens molding mold, usually at −20 ° C. A plastic spectacle lens can be obtained by heating between ˜150 ° C.

  In addition, a mixed solution of at least one benzotriazole compound selected from the general formula (1) and a plastic lens monomer may be used in JP-A-07-063902, JP-A-07-104101, JP-A-09-. Polymerization catalysts described in 208621, JP 09-255781, etc., internal mold release agents, antioxidants, etc. described in JP 01-163012, JP 03-28112, etc. The auxiliary can be added as required. Moreover, the plastic spectacle lens obtained by the present invention can be dyed using a colorant. Further, in order to improve the scratch resistance, a cured film can be formed on the plastic lens using a coating liquid having a particulate inorganic material such as an organosilicon compound, tin oxide, silicon oxide, zirconium oxide, titanium oxide or the like. In addition, a primer layer mainly composed of polyurethane can be provided in order to improve impact resistance. Furthermore, in order to impart antireflection performance, an antireflection film can be applied using silicon oxide, titanium dioxide, zirconium oxide, tantalum oxide, or the like. In order to improve water repellency, a water repellent film can be formed on the antireflection film using an organosilicon compound having fluorine atoms.

Hereinafter, the present invention will be specifically described with reference to examples. However, the present invention is not limited to these examples. The physical properties of the manufactured lens were determined by the following method.
(1) YI value measurement It measured according to the yellowness of a plastic prescribed | regulated to JISK7103-1977, and the yellowness test method.
(2) Transmittance measurement The ultraviolet transmittance (light transmittance) at wavelengths of 395 nm, 400 nm, and 405 nm was measured using a spectrophotometer (U3410, manufactured by Hitachi, Ltd.).
(3) Refractive index (ne) and Abbe number (νe)
It was measured at 20 ° C. using a precision refractometer KPR-200 manufactured by Carnew.
Examples 1 to 9 produce lenses with an episulfide monomer as a main component, and Example 10 produces lenses by mixing an episulfide monomer and a thiourethane monomer. No. 13 is a lens manufactured with a thiourethane monomer as a main component.

Example 1
93.00 parts by weight of bis- (β-epithiopropyl) sulfide as a lens raw material monomer, 1.00 parts by weight of 2-hydroxyethyl methacrylate, and 5-methyl-2- (2-hydroxy-4-decyloxy) as an ultraviolet absorber After adding 0.05 parts by weight of phenyl) benzotriazole and stirring and mixing, 6.00 parts by weight of n-butylthioglycolate and 0.05 parts by weight of tetra-n-butylphosphonium bromide as a catalyst were added. The mixture was stirred and mixed for 3 minutes under a reduced pressure of 10 mmHg to prepare a lens monomer composition. Next, this lens monomer composition was poured into a lens molding mold (0.00D, lens diameter 80 mm, wall thickness 2.0 mm set) consisting of a glass mold and a resin gasket prepared in advance. After gradually raising the temperature from 20 ° C. to 100 ° C. over 20 hours in a furnace, polymerization was carried out by maintaining at 100 ° C. for 30 minutes. After completion of the polymerization, the mold was removed and then heat treated at 110 ° C. for 1 hour to obtain a lens.
When the physical properties of the above (1) to (3) were measured for the obtained lens, the refractive index was 1.71 and the Abbe number was 36. The YI value at the center of the lens (thickness: 2.0 mm) was 1.3, and the lens was colorless and transparent. The transmittance at 395 nm was 42%, the transmittance at 400 nm was 69%, and the transmittance at 405 nm was 81%. Moreover, when the external appearance was evaluated visually, it was colorless and transparent. The results are shown in Table 1.

Example 2
In Example 1, a lens was produced by changing the types and amounts of the lens raw material monomer and the ultraviolet absorber as follows.
As a lens raw material monomer, 90.00 parts by weight of bis- (β-epithiopropyl) sulfide, 5.00 parts by weight of 2-hydroxy-3-phenoxypropyl methacrylate, and 5.00 parts by weight of bismercaptoethyl sulfide are used. A lens was produced in the same manner as in Example 1 using 0.05 part by weight of 5-methyl-2- (2-hydroxy-4-octyloxyphenyl) benzotriazole as an ultraviolet absorber. ) To (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 1.

Example 3
In Example 1, the lens was manufactured by changing the kind of ultraviolet absorber as follows.
A lens was produced in the same manner as in Example 1 except that 0.05 part by weight of 5-methoxy-2- (2-hydroxy-4-octyloxyphenyl) benzotriazole was used as the ultraviolet absorber. (1) The physical properties of (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 1.

Example 4
In Example 2, a lens was manufactured by changing the type of the ultraviolet absorber as follows.
A lens was produced in the same manner as in Example 2 except that 0.05 part by weight of 5-ethoxy-2- (2-hydroxy-4-octyloxyphenyl) benzotriazole was used as the ultraviolet absorber. (1) The physical properties of (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 1.

Example 5
In Example 1, the lens was manufactured by changing the amount of the ultraviolet absorber as follows.
A lens was produced in the same manner as in Example 1 except that 0.30 parts by weight of 5-methyl-2- (2-hydroxy-4-decyloxyphenyl) benzotriazole was added as an ultraviolet absorber. (1) The physical properties of (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 1.

Example 6
In Example 2, a lens was manufactured by changing the type and amount of the ultraviolet absorber as follows.
A lens was produced in the same manner as in Example 2 except that 0.30 part by weight of 5-methyl-2- (2-hydroxy-4-dodecyloxyphenyl) benzotriazole was added as an ultraviolet absorber. (1) The physical properties of (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 1.

Example 7
In Example 1, a lens was manufactured by changing the type and amount of the ultraviolet absorber as follows.
A lens was produced in the same manner as in Example 1 except that 0.30 part by weight of 5-methyl-2- (2-hydroxy-4-octyloxyphenyl) benzotriazole was added as an ultraviolet absorber. (1) The physical properties of (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 1.

Example 8
In Example 3, lenses were produced by changing the amount of the ultraviolet absorber as follows.
A lens was produced in the same manner as in Example 3 except that 0.25 part by weight of 5-methoxy-2- (2-hydroxy-4-octyloxyphenyl) benzotriazole was added as an ultraviolet absorber. (1) The physical properties of (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 1.

Example 9
In Example 4, lenses were produced by changing the amount of the ultraviolet absorber as follows.
A lens was produced in the same manner as in Example 4 except that 0.25 parts by weight of 5-ethoxy-2- (2-hydroxy-4-octyloxyphenyl) benzotriazole was added as an ultraviolet absorber. (1) The physical properties of (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 1.

Example 10
As a lens raw material monomer, 70.00 parts by weight of bis- (β-epithiopropyl) sulfide, 18.82 parts by weight of 2,5-bismercaptomethyl-1,4-dithiane (polythiol compound), 2,5-bisisocyanato Methyl-1,4-dithiane (polyisocyanate compound) 4.18 parts by weight and bisisocyanatomethylbicyclo [2.2.1] heptane (polyisocyanate compound) 7.00 parts by weight are used as a lens monomer. After adding 0.30 part by weight of 5-ethoxy-2- (2-hydroxy-4-octyloxyphenyl) benzotriazole as an absorbent, stirring and mixing, 0.05 weight of tetra-n-butylphosphonium bromide as a catalyst 0.005 parts by weight of acid phosphate ester (trade name: JP506H (Johoku Chemical Co., Ltd.)) as a mold release agent Then, the mixture was stirred and mixed for 3 minutes under a reduced pressure of 10 mmHg to prepare a lens monomer composition.The lens monomer composition was prepared from a glass mold and a resin gasket prepared in advance. (Set to 0.00D, lens diameter 80 mm, wall thickness 2.0 mm), gradually heated in an electric furnace from 20 ° C. to 100 ° C. over 20 hours, and then held at 100 ° C. for 30 minutes After completion of the polymerization, the mold was removed and then heat treated at 110 ° C. for 1 hour to obtain a lens.
When the physical properties of the above (1) to (3) were measured for the obtained lens, the refractive index was 1.70 and the Abbe number was 36. The YI value at the center of the lens (thickness 2.0 mm) was 1.7, and the lens was colorless and transparent. The transmittance at 395 nm was 3%, the transmittance at 400 nm was 18%, and the transmittance at 405 nm was 52%. Moreover, the external appearance was evaluated visually. The results are shown in Table 1.

Example 11
47.54 parts by weight of bis (isocyanatomethyl) cyclohexane as a lens raw material monomer, 0.45 parts by weight of dimethyltin dichloride as a catalyst, and acidic phosphate ester (trade name: JP506H (Johoku Chemical Co., Ltd.) as a release agent After adding 0.20 parts by weight and 1.00 parts by weight of 5-methyl-2- (2-hydroxy-4-octyloxyphenyl) benzotriazole as an ultraviolet absorber and stirring and mixing, bis (mercapto) is further used as a lens raw material monomer. A monomer composition for a lens was prepared by adding 26.00 parts by weight of methyl) -1,4-dithiane and 26.47 parts by weight of pentaerythritol tetrakismercaptoacetate and stirring and mixing for 30 minutes under a reduced pressure of 10 mmHg. This lens monomer composition can be prepared in advance using a glass mold and a resin gasket. After being poured into a lens molding mold (0.00D, lens diameter 80 mm, wall thickness 2.0 mm) and gradually heated from 20 ° C. to 100 ° C. over 20 hours in an electric furnace, After removing from the furnace and removing the gasket, it was returned to the furnace and further heated to 120 ° C. over 1 hour and held for 3 hours at 120 ° C. After the polymerization was completed, the mold was removed and then 120 ° C. To obtain a lens.
When the physical properties of the above (1) to (3) were measured for the obtained lens, the refractive index was 1.60 and the Abbe number was 41. The YI value at the center (thickness 2.0 mm) was 1.6, and the lens was slightly yellowish, but the transmittance at 395 nm was 2%, the transmittance at 400 nm was 15%, and the transmittance at 405 nm was It was 46% and showed a good UV-cutting property. Moreover, the external appearance was evaluated visually. The results are shown in Table 1.

Example 12
In Example 11, the lens was manufactured by changing the kind of ultraviolet absorber as follows.
A lens was produced in the same manner as in Example 11 except that 1.00 parts by weight of 5-methoxy-2- (2-hydroxy-4-octyloxyphenyl) benzotriazole was added as an ultraviolet absorber. (1) The physical properties of (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 1.

Example 13
In Example 11, the lens was manufactured by changing the kind of ultraviolet absorber as follows.
A lens was produced in the same manner as in Example 11 except that 1.00 parts by weight of 5-ethoxy-2- (2-hydroxy-4-octyloxyphenyl) benzotriazole was added as an ultraviolet absorber. The physical properties of (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 1.

Comparative Example 1
Comparative Example 1 corresponds to Examples 1 and 3, and in Examples 1 and 3, the type of the ultraviolet absorber was changed as follows to produce lenses.
Examples 1 and 3 except that 0.05 part by weight of 2- (2-hydroxy-5-tert-octylphenyl) benzotriazole, which is not a benzotriazole compound represented by the general formula (1), was added as an ultraviolet absorber. A lens was produced in the same manner, and the physical properties (1) to (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 2. As shown in Table 2, compared with the lenses obtained in Example 1 and Example 3, the YI value and the ultraviolet absorption performance were inferior in balance.

Comparative Example 2
Comparative Example 2 corresponds to Examples 6 and 9, and in Examples 6 and 9, the type and amount of the ultraviolet absorber were changed as follows to produce lenses.
Examples 6 and 9 except that 0.30 part by weight of 2- (2-hydroxy-5-tert-octylphenyl) benzotriazole, which is not a benzotriazole compound represented by the general formula (1), was added as an ultraviolet absorber. A lens was produced in the same manner, and the physical properties (1) to (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 2. As shown in Table 2, compared with the lenses obtained in Example 6 and Example 9, the balance between the YI value and the ultraviolet absorption performance was inferior.

Comparative Example 3
Comparative Example 3 corresponds to Example 10, and a lens was manufactured in Example 10 except that the type of ultraviolet absorber was changed as follows.
As in Example 10, except that 0.30 part by weight of 2- (2-hydroxy-5-tert-octylphenyl) benzotriazole, which is not a benzotriazole compound represented by the general formula (1), was added as an ultraviolet absorber. A lens was manufactured, and the physical properties (1) to (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 2. As shown in Table 2, compared with the lens obtained in Example 10, the YI value and the ultraviolet absorption performance were inferior in balance.

Comparative Example 4
Comparative Example 4 corresponds to Example 10, and a lens was manufactured in Example 10 except that the type and amount of the ultraviolet absorber were changed as follows.
A lens was obtained in the same manner as in Example 10 except that 0.50 part by weight of 2- (2-hydroxy-5-methylphenyl) benzotriazole which is not a benzotriazole compound represented by the general formula (1) was added as an ultraviolet absorber. And the physical properties of (1) to (3) above were measured. The results are shown in Table 2. Moreover, the external appearance was evaluated visually. As shown in Table 2, compared with the lens obtained in Example 10, the YI value and the ultraviolet absorption performance were inferior in balance.

Comparative Example 5
Comparative Example 5 corresponds to Examples 11-13, and in Examples 11-13, the type and amount of the ultraviolet absorber were changed as follows to produce lenses.
Examples 11 to 13 except that 1.00 parts by weight of 2- (2-hydroxy-5-tert-octylphenyl) benzotriazole, which is not a benzotriazole compound represented by the general formula (1), was added as an ultraviolet absorber. A lens was produced in the same manner, and the physical properties (1) to (3) were measured. Moreover, the external appearance was evaluated visually. The results are shown in Table 2. As shown in Table 2, compared with the lenses obtained in Examples 11 to 13, the YI value and the ultraviolet absorption performance were inferior in balance.

  In Tables 1 and 2, catalyst (1) is tetra-n-butylphosphonium bromide and catalyst (2) is dimethyltin dichloride.

The plastic spectacle lens obtained by the production method of the present invention is excellent in ultraviolet absorptivity, in particular, excellent in the absorptivity of ultraviolet rays up to a wavelength of about 400 nm and having little yellow coloring.

Claims (6)

The following general formula (1)

(In the formula, R represents a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, a propoxy group or a butoxy group, and R ′ represents a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, Hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy group, decyloxy group, undecyloxy group or an dodecyloxy radical, n is the integer 1, and R 'is you bonded to the phenyl group at the 4-position.)
An ultraviolet absorber for plastic spectacle lenses comprising at least one benzotriazole compound selected from the group consisting of (thio) urethane-based monomer and / or episulfide-based monomer is mixed and then polymerized. Production method. A plastic spectacle lens manufactured by the method according to claim 1 . 3. The plastic spectacle lens according to claim 2, wherein the benzotriazole compound is added in an amount of 0.03 to 10 parts by weight based on 100 parts by weight of the (thio) urethane monomer and / or episulfide monomer. The plastic spectacle lens according to claim 2, wherein the benzotriazole compound is added in an amount of 0.03 to 6 parts by weight with respect to 100 parts by weight of a (thio) urethane monomer and / or an episulfide monomer. YI at the lens center when the center thickness of the lens was 2.0 mm (yellowness) is in the range of 0.7 to 1.8, and, according to claim 2 light transmittance at a wavelength of 400nm is 40% or less The plastic spectacle lens in any one of -4 . When the lens center thickness is 2.0 mm, the YI (yellowness) at the lens center is in the range of 0.7 to 1.7, the light transmittance at a wavelength of 395 nm is 6% or less, and the light beam at a wavelength of 400 nm. The plastic spectacle lens according to any one of claims 2 to 4 , having a transmittance of 7 to 20% and a light transmittance of 50% or more at a wavelength of 405 nm.