JP2005025228A - Plastic spectacle lens excellent in ultraviolet-ray absorbing property and method of producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a plastic spectacle lens little colored in spite of its power to nearly thoroughly absorb UV up to about 400 nm wavelength. <P>SOLUTION: In the method of producing the plastic spectacle lens excellent in UV absorbing property, 2-(2-hydroxy-4-octyloxyphenyl)-benzotriazole is added and mixed with a diethylene glycol bisallyl carbonate type monomer and this monomer is polymerized. The plastic spectacle lens is also provided. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to a plastic spectacle lens excellent in ultraviolet absorption and a method for producing the same. More specifically, the present invention relates to a plastic spectacle lens with little yellow coloring despite absorbing a long wavelength ultraviolet ray having a wavelength of around 400 nm and a method for manufacturing the same.

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, and the plastic lens is impregnated into the plastic lens by immersing the plastic lens in an aqueous solution in which the ultraviolet absorber heated to 80 to 100 ° C. is dispersed ( 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.

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

Said 1st method currently disclosed by patent documents 3-5 etc. is a method used in order to improve the light resistance of a plastic lens. According to the first method, a wavelength of around 400 nm using a conventionally used ultraviolet absorber (2,2′-dihydroxy-4-methoxybenzophenone, 2,2′-dihydroxy-4-n-octoxybenzophenone, etc.) When manufacturing lenses that absorb up to UV rays, diethylene glycol bisallyl carbonate, which is a typical plastic spectacle lens material, has a problem of poor appearance due to the large yellow coloration, and the use of UV absorbers Since the amount increases, 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. Even when the ability cannot be imparted or can be imparted, a long immersion time is often required. Although a method using an organic solvent instead of water has been proposed, a plastic lens that absorbs ultraviolet rays having a wavelength of up to about 400 nm manufactured by this method has a problem that yellow coloration 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.
The present invention solves the above-mentioned problems, is superior in absorbability of ultraviolet rays up to a wavelength of around 400 nm, has less yellow coloring, and reduces the amount of ultraviolet absorber added compared to conventional plastic spectacle lenses. It is an object of the present invention to provide a method for manufacturing a plastic spectacle lens that can be used.

As a result of intensive investigations to achieve the above-mentioned object, the present inventors are excellent in the absorption of ultraviolet rays up to a wavelength of around 400 nm by using a specific plastic lens monomer and a specific ultraviolet absorber, and yellow coloring is achieved. The inventors have found that fewer spectacle lenses can be obtained and have reached the present invention.
That is, the present invention has an ultraviolet absorptivity characterized in that 2- (2-hydroxy-4-octyloxyphenyl) -benzotriazole is added to and mixed with a diethylene glycol bisallyl carbonate monomer, and then the monomer is polymerized. An excellent plastic spectacle lens manufacturing method and a plastic spectacle lens are provided.

  According to the present invention, it is possible to obtain a plastic spectacle lens with little coloration of the lens although it absorbs ultraviolet rays having a wavelength of around 400 nm almost completely.

The ultraviolet absorber used in the present invention is 2- (2-hydroxy-4-octyloxyphenyl) -benzotriazole. The 2- (2-hydroxy-4-octyloxyphenyl) -benzotriazole is registered in the Chemical Abstract Registry Number (3147-77-1) and is a known substance. However, when 2- (2-hydroxy-4-octyloxyphenyl) -benzotriazole is used as a UV absorber for plastic lenses, and when mixed with a plastic lens monomer and polymerized, the wavelength is close to 400 nm. It has not been known that a plastic lens having a characteristic of absorbing ultraviolet rays and having less yellow coloring than a conventional plastic lens can be obtained. Furthermore, it has not been known that such characteristics can be obtained by adding a small amount of 2- (2-hydroxy-4-octyloxyphenyl) -benzotriazole.
The amount of 2- (2-hydroxy-4-octyloxyphenyl) -benzotriazole added varies depending on the type of plastic lens monomer, desired UV absorption characteristics, etc., but is 0.01 to 10% by weight based on the plastic lens monomer. It is desirable to use in the range of 0.01 to 5% by weight.

  The plastic lens monomer used in the present invention is a diethylene glycol bisallyl carbonate monomer.

  The diethylene glycol bisallyl carbonate-based monomer includes 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 described in these publications and a monomer copolymerizable with diethylene glycol bisallyl carbonate corresponds to the diethylene glycol bisallyl carbonate monomer in the present invention.

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 can be mentioned as preferable ones.
(1) When the lens center thickness is 2.2 mm, the YI (yellowness) at the lens center is in the range of 0.7 to 1.6, and the ultraviolet transmittance at a wavelength of 380 nm is 30% or less. 2- (2-hydroxy-4-octyloxyphenyl) -benzotriazole, a diethylene glycol bisallyl carbonate eyeglass lens.

The plastic spectacle lens of the present invention is obtained by polymerizing a plastic lens monomer to which 2- (2-hydroxy-4-octyloxyphenyl) -benzotriazole, which is an ultraviolet absorber, is added and mixed.
The method for polymerizing the plastic lens monomer is not particularly limited, but usually cast polymerization is employed. That is, after mixing 2- (2-hydroxy-4-octyloxyphenyl) -benzotriazole and the above-mentioned plastic lens monomer, this mixed solution was poured into a lens molding mold, and -20 ° C to 150 ° C. A plastic spectacle lens can be obtained by heating between. As a mixed solution of 2- (2-hydroxy-4-octyloxyphenyl) -benzotriazole and a plastic lens monomer, JP-A-07-063902, JP-A-07-104101, JP-A-09-208621 are disclosed. Aids such as polymerization catalysts described in JP-A-09-255781, etc., internal mold release agents, antioxidants, etc. described in JP-A-01-163012, JP-A-03-281312, etc. Agents can be added as needed.

  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 described below were determined by the following methods.
(1) YI value measurement:
It was measured in accordance with the yellowness and yellowness test method for plastics specified in JIS K7103-1977.
(2) Transmittance measurement:
The ultraviolet transmittance at a wavelength of 380 nm or 400 nm was measured using a spectrophotometer (U3410, manufactured by Hitachi, Ltd.).

Example 1
To 100 parts by weight of diethylene glycol bisallyl carbonate, 0.10 parts by weight of 2- (2-hydroxy-4-octyloxyphenyl) -benzotriazole as an ultraviolet absorber and 3 parts by weight of diisopropyl peroxydicarbonate as a polymerization catalyst were added. The mixture was thoroughly stirred and mixed to prepare a lens monomer composition.
Next, this lens monomer composition was injected into a lens molding mold (0.00D, lens diameter 70 mm, wall thickness set to 2.2 mm) consisting of a glass mold and a resin gasket prepared in advance. Polymerization was carried out by gradually raising the temperature from 40 to 85 ° C. in an oven over 20 hours and holding at 85 ° C. for 1 hour.
After the polymerization, the gasket and the mold were removed, and then heat treated at 120 ° C. for 1 hour to obtain a lens.
The YI value at the center (thickness: 2.2 mm) of the obtained lens was 1.6, and the lens was slightly yellowish, but the UV transmittance at 380 nm was 1%, and good UV blocking properties. showed that. The spectral curve is shown in FIG.

Example 2
A lens was obtained in the same manner as in Example 1 except that the addition amount of the ultraviolet absorber in Example 1 was changed to 0.05 part by weight.
The YI value at the center (thickness: 2.2 mm) of the obtained lens was 1.4, and the lens was slightly yellowish, but the UV transmittance at 380 nm was 9%, and good UV blocking properties were obtained. Indicated. The spectral curve is shown in FIG.

Example 3
A lens was obtained in the same manner as in Example 1 except that the addition amount of the ultraviolet absorber in Example 1 was changed to 0.025 part by weight.
The YI value at the center (thickness: 2.2 mm) of the obtained lens was 1.0, and the lens was slightly yellowish, but the UV transmittance at 380 nm was 27%, and good UV blocking properties. showed that. The spectral curve is shown in FIG.

Comparative Example 1
A lens was obtained in the same manner as in Example 1, except that 0.50 part by weight of 4-dodecyloxy-2-hydroxybenzophenone was used as the ultraviolet absorber in Example 1.
The YI value at the center (thickness: 2.2 mm) of the obtained lens was 2.1, and the UV transmittance at 380 nm was 1%, indicating good UV cutting properties, but the lens was colored yellow. It was. The spectral curve is shown in FIG.

Comparative Example 2
A lens was obtained in the same manner as in Example 1 except that 0.10 parts by weight of 2- (2-hydroxy-5-tert-octylphenyl) benzotriazole was used as the ultraviolet absorber in Example 1.
The YI value at the center (thickness: 2.2 mm) of the obtained lens was 1.6, and the UV transmittance at 380 nm was 10%, indicating good UV cutting properties, but the lens was colored yellow. It was. The spectral curve is shown in FIG.
The above is summarized in Table 1.

It is a figure which shows the spectral curve in Examples 1-3. It is a figure which shows the spectral curve in the comparative examples 1 and 2. FIG.

Claims (3)

  2- (2-hydroxy-4-octyloxyphenyl) -benzotriazole is added to and mixed with a diethylene glycol bisallyl carbonate-based monomer, and then the monomer is polymerized. Manufacturing method.   A plastic spectacle lens having excellent long-wavelength ultraviolet absorptivity formed by adding 2- (2-hydroxy-4-octyloxyphenyl) -benzotriazole to a diethylene glycol bisallyl carbonate monomer and then polymerizing the monomer. The YI (yellowness) at the lens center when the lens center thickness is 2.2 mm is in the range of 0.7 to 1.6, the ultraviolet transmittance at a wavelength of 380 nm is 30% or less, and 2- A plastic spectacle lens comprising a polymer of a monomer of diethylene glycol bisallyl carbonate, which contains (2-hydroxy-4-octyloxyphenyl) -benzotriazole.

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