JPH0245161B2 - GOSEIJUSHIRENZU - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a synthetic resin lens, and more specifically to a surface-treated synthetic resin lens having an inorganic dielectric hard coat layer, an antireflection film, and both of these functions provided on the surface of the lens. The gist of the invention is to significantly improve the adhesion between the synthetic resin lens and the inorganic dielectric material, thereby effectively extending the durability of eyeglass lenses and the like. In recent years, an increasing number of people are wearing synthetic resin eyeglass lenses instead of glass lenses. This is because synthetic resin lenses are less likely to break than glass, are highly safe, lightweight, can be used for active activities, are easy to dye, have a high degree of flexibility, and are fashionable. Another drawback is that it is more easily scratched than glass. For this reason, hard coat technology has been developed to provide a hard coating layer on the lens surface to make it less likely to be scratched. Two methods have been proposed for forming this hard coat layer: one is to apply an inorganic substance by vacuum deposition or chemical vapor deposition, and the other is to apply an organic substance. In addition, anti-reflection film technology increases light transmittance, as typified by camera lenses.
In addition, it is preferable that the reflectance be somewhat lower, since it serves to compensate for the important function of a spectacle lens that causes physiological problems. Therefore, the structure of the antireflection film is a multilayer film, and includes several layers. In particular, synthetic resin lenses cannot be heated to high temperatures during vapor deposition,
In practice, perfect adhesion between the synthetic resin lens and the inorganic material interface has not been achieved because the thermal expansion coefficients are widely different. In the case of spectacle lenses, they are exposed to heat cycles and high humidity environments quite frequently, such as when the wearer washes them with running water or hot water. For this reason, there were problems such as the film peeling off. The present invention is based on the discovery that the interfacial adhesion can be significantly improved by adding a hydrophilic hydroxyl group-containing monomer to the synthetic resin lens composition in order to improve the adhesion of these interfaces. . This monomer containing a hydrophilic hydroxyl group and capable of radical polymerization has the following structure. (In the formula, R represents a carboxy group or an alkyl group) A lens material that is effective by adding the monomer capable of radical polymerization described above is diethylene glycol bisallyl carbonate (hereinafter referred to as CR).
-39) bisphenol A dimethacrylate, 2,2-bis(4-methacroyloxyethoxy 3,5-dibromophenyl)propane, chlorostyrene, styrene, 2,2-bis(4-methacroyloxyethoxy) ethoxyphenyl)propane,
1,3-butylene glycol dimethacrylate
Suitable for homopolymers and copolymers of ethylene glycol acrylate, polyethylene glycol dimethacrylate, ethoxyethyl methacrylate, acrylonitrile, methyl methacrylate, allyl methacrylate, methoxybutyl methacrylate, trimethylolpropane triacrylate, cyanomethyl methacrylate, allyl cinnamate. Yes, you can. It is also common practice to copolymerize the above monomers with vinyl acetate, ethylene glycol maleic anhydride, triallyl cyanurate, diallyl phthalate, etc. to improve the performance of lenses. This will be explained below using examples. Example 1 BisGMA represented by structural formula (1) was added to CR-39 and compared with a product without additives. 93% CR-39 by weight
5% BisGAM and 3% by weight of diisopropyl peroxydicarbonate (IPP) as a polymerization initiator were added thereto, and after stirring well, prepolymerization was carried out at 40°C to give a viscosity of 80 CPS. After cooling to room temperature, apply pressure.
A 0.1μ filter is passed through the glass mold mold prepared in advance (convex glass mold, concave glass mold,
The lens was injected into a gasket and a pressurized spring whose outer periphery was injection-molded with soft synthetic resin, heated to 40°C or 90°C in an atmospheric furnace to polymerize, and then released from the mold and the lens was taken out. Additive-free lenses form in exactly the same way,
After taking it out, it was annealed at 100°C for 2 hours, and an antireflection film was vacuum-deposited to give the same batch treatment. The vacuum-deposited film consists of a hard coat layer of 1 μm of SiO ₂ from the lens surface, and an anti-reflection film layer.
Five layers of ZrO ₂ , Al ₂ O ₃ , ZrO ₂ , and SiO ₂ including the hard coat layer were deposited to the required thickness to produce a finished product. Example 2 2,2-bis(4-methacroyloxyethoxy3,5-dibromphenyl)propane 50% by weight, styrene 40% by weight, BP represented by structural formula (5)
9% by weight of -4EA and 1% by weight of lauroyl peroxide were added and mixed, a lens was formed in the same manner as in Example 1, the hard coat layer was made 2 μ thicker than in Example 1, and an antireflection film was further formed. I did it. Both Examples 1 and 2 contain 0.02 to 0.05% by weight of an ultraviolet absorber, although the composition ratio is not stated. Comparative Example 1 is a lens that does not contain BiSGAM described in Example 1, Comparative Example 2 is a lens that does not contain BP-4EA described in Example 2, and Table 1 shows the investigation results of each lens characteristic.

[Table] The test method in Table-1 was performed as follows. Pencil hardness: Performed according to JIS (K5400). Impact resistance: A steel ball drop test was performed on a flat plate with a center thickness of 2 mm according to FDA standards, and those that did not break were considered good. Heat resistance: Leave in a constant temperature bath at 70℃ for 3 hours, the film will peel off,
A film with no cracks was considered good. Hot water resistance: It was immersed in hot water at 70°C for 2 hours, and those with no film peeling or film cracks were rated as good. Steel wool: A load of 1 kg was applied to #000 steel wool and rubbed 20 times, and the degree of scratching was evaluated as good if it was at a level of Comparative Example 1 or higher. Wire brush: A brass wire brush with 3 rows of 40 wires each measuring 0.3 mm x 2 cm was tested in the same manner as steel wool, and a level of Comparative Example 1 or higher was considered good. Beading processability: Items that can be ground with a diamond edger for lens processing, or polished with a CR-39 lens polisher, and have a clean surface after grinding and polishing, are considered good. As explained above based on the examples, by adding a hydrophilic hydroxyl group-containing monomer,
The coating film quality using inorganic dielectric material has high heat resistance,
It was found that the durability in hot water resistance was improved and the practical value was increased. The amount added depends on the monomers added and the characteristics of the base resin, but no effect will be seen if the amount added is less than 1%. Also, if it exceeds 20%, although it is effective in impact resistance, it becomes easily scratched in terms of scratch resistance, and it also swells when exposed to heat or water, making unevenness with other surfaces noticeable. Not suitable as a lens. The present invention is
It will be able to contribute to maintaining the durability of synthetic resin lenses with anti-reflection coatings in the future, and its industrial value is great.

Claims (1)

[Claims] 1 Or, Copolymerization with a monomer containing 1 to 20% by weight of a monomer, the balance of which is one or two selected from radically polymerizable monomers having an allyl group, a (meth)acrylic group, and a vinyl group. At least ZRO ₂ thin film layer on the synthetic resin lens, consisting of coalescing
A synthetic resin lens characterized by forming a multilayer inorganic material layer including a sio2 thin film layer and a _sio2 thin film layer.