JPS6181416A - Plastic lens material - Google Patents

Abstract

PURPOSE:The titled material having high refractive index, improved dyeability, processing properties, and impact resistance, obtained by copolymerizing dimethallyl orthophthalate, dimethallyl isophthalate and/or dimethalyl terephthalate with a monomer shown by a specific formula. CONSTITUTION:(A) Preferably 70-99wt% dimethllyl orthophthalate, dimethallyl isophthalate and/or dimethallyl terephthalate is copolymerized with (B) 1-30wt% monomer shown by the formula (R1 and R2 are H, or CH3; m is 0-3; n is 0-2) or its mixture, to give the aimed material having >=1.55 refractive index.

Description

[Detailed Description of the Invention] [A.1. Field of Application] The present invention relates to a plastic lens material,
More specifically, the present invention relates to a three-dimensionally crosslinked high refractive index-F plastic lens material.

[Conventional techniques] Plastic lenses are becoming widely used in optical products due to their ease of molding and light weight. In particular, for eyeglass lenses, the weight of the entire eyeglass has a large effect on both the physiology and the optics of the eyeglass, so it is desirable that the lens be lightweight.For this reason, the resin that has become the mainstream for plastic eyeglass lenses in recent years has been made from polydiethylene glycol bisallyl carbonate. Naru CR
-39 (PPG company name, product name), and the lens Tr
M) can be reduced to 1/2 that of inorganic glass.

However, since the refractive index of CR-39 is 1.49 to 1.50, compared to inorganic glass, CR-39 tends to have larger center thickness, edge thickness, and curvature. A plastic lens with a high refractive index is desired. Polycarbonate (n, = 1.5) is a familiar resin with a high refractive index.
8) There is polystyrene (no = 1.60).These are linear polymers, and because they are thermoplastic, they cannot be cast and are not suitable for producing a wide variety of products such as glasses and lenses. It is. Furthermore, 74+i) The plastic lens has a back layer 1. 1) The surface is easily scratched due to insufficient surface hardness, is easily affected by organic solvents, and has poor heat resistance, so its use is limited to only a limited range. The reality is that it is limited to.

Three-dimensionally crosslinked high refractive index plastic lens materials are provided by (1) a method using di(meth)acrylate derived from bisphenol A as the main component (Japanese Patent Publication No. 17527/1982); (2) l・Method using di(meth)acrylate derived from rogogenated bisphenol A as the main component (Japanese Patent Application Laid-open No. 1041101/1983)
, (3) Method of using halogenated styrene monomer and polyfunctional methacrylate together (JP-A-57-104101, JP-A-57-28118, JP-A-57-28118)
No.) (4) Method using diallyl phthalate monomer.

(JP-A-57-212401, JP-A-58-155
No. 13) etc. have been proposed.

[Problems to be Solved by the Invention] However, with the method (1), it is difficult to obtain a three-dimensional crosslinked plastic with a refractive index of 1.55 or more.

Although methods (2) and (3) result in a three-dimensionally crosslinked plastic having a high refractive index of 1.60 or more, there are problems with the coloring and weather resistance of the plastic. Furthermore, the method (4) also has the problem of coloring and, in addition, has the disadvantage of poor transmittance. Li, which generally uses a compound having a (meth)acryloyl group and a styrene monomer, contains a polymerization inhibitor in the compound, and it is extremely difficult to avoid the problem of yellowing of the cured product during cast polymerization. There is a drawback.

It is an object of the present invention to provide a three-dimensionally crosslinked high refractive index plastic lens that solves the above-mentioned problems and has excellent light transmission and weather resistance.

[Means for solving the problems] That is, the gist of the present invention is to provide dimethallyl orthophthalate,
At least one member selected from dimethallyl isophthalate and dimethallyl terephthalate and a 1% fi compound represented by the general formula [N (wherein R is water or a methyl group, - and n represent 0.1 or 2) or a mixture thereof, which has a refractive index of 1.55 or more, and has good dyeability, processability,
A plastic lens material with excellent impact resistance.

Specific examples of the second component of the present invention represented by the general formula [13] include specific examples of the monomer and 1-, phenyl 7
Acrylate, Hensyl acrylate.

Examples include phenoxyethyl acrylate, phenyl methacrylate, hensyl methacrylate, phenoxy-ethyl methacrylate, and the like.

When carrying out the present invention, 1) the first component of the present invention, dimethallyl phthalate (referring to at least one selected from dimethallyl orthophthalate, dimethallyl isophthalate, and dimethallyl terephthalate), is 70 to 99 competition%
It is preferable to use the range of .

If the content of the first component is less than 70% by weight, the optical properties will be significantly deteriorated, and if it exceeds 99%, the dyeing property will be 5, which is not preferable.

Further, the radical polymerization initiator used in the copolymerization to obtain the lens resin of the present invention is not particularly limited, and may include known benzoyl peroxide, p-chlorobenzoyl peroxide, diimpropyl peroxycarbonate,
Peroxides such as di-2-ethylhexyl rubber quine carbonate and tertiary butyl peroxyn piperate can be used in an amount of 0.1 to 5% by weight.

[Examples] The present invention will be specifically described below based on Examples. In the examples, "parts" means parts by weight.

Example 1 A resin composition consisting of 95 parts of dimethacrylorthophthalate synthesized from methallyl chloride and potassium heptalate, 5 parts of fenoquinethyl methacrylate, 3 parts of diisopropyl peroxycarbonate, and 0.5 parts of penzoyl peroxide was prepared in a 65-liter diameter container. It was poured into a mold consisting of glass for molding and a polyethylene gas get, and
It was kept in a hot air oven at ℃ for 15 hours. Furthermore, at 90℃
time.

After holding at 100'C for 4 hours, the polymer was taken out from the mold and its refractive index, hardness, I@impact property, workability, visible light transmittance, dyeability, etc. were measured. The result is! As shown in Table 7S1, with a colorless and transparent lens.

Pencil hardness 4H1 refractive index 1.563, visible light transmittance 9
0% or more, and a lens with good impact resistance, workability, and dyeability was obtained. The refractive index was measured using an Atsube refractometer, and the pencil hardness was measured according to JIS-5400. Other physical properties were measured by the methods described below.

A lens with a center wall thickness of 21 was tested according to FDA standards.

The additives were processed using an eyeglass lens drilling machine, and those with no chipped edges and a smooth cut surface were considered acceptable.

Dyeing property, Sumikalon Blue-E-FBL (Sumikaron Chemical T
A solution prepared by dispersing 1.5 g (manufactured by a commercial company) of 12 in water is heated to 80°C, and a lens is immersed in this dye bath for 5 minutes to show dyeing properties equivalent to that of diethylene glycol bisallyl carbonate homopolymer. The item was passed.

Examples 2-3. Comparative Examples 1 to 5 Lenses of various compositions were created using the same method as in Example 1, and the results are summarized in Table 1 as Examples and Comparative Examples.

Margins below [Effects of the Invention] As is clear from Table 1, the plastic lens material of the present invention is significantly superior to the conventional products shown in the comparative examples in many of the performances required for eyeglass lenses. Recognize.

The plastic lens material of the present invention has a visible light transmittance of 9
It is a colorless transparent material with a refractive index of 0% or more and has a high refractive index of 1.55 or more, and also has various properties required for eyeglass lenses such as scratch resistance, weather resistance, diamond grindability, and stainability. It is possible to provide a plastic lens that fully satisfies the following, and its industrial value is extremely large.

B Continuing Amendment 16 October 26, 1999 Indication of the case Patent Application No. 1983-203297 26 Name of the invention Plastic lens material 3 Supplement 1 Relationship to the famous case Patent applicant: Kyobashi 2, Chuo-ku, Tokyo No. 3-13 (603) Mitsubishi Rayon Co., Ltd. President Akio Kawasaki 4, Agent Address: 2-3-18 Kyobashi, Chuo-ku, Tokyo 104 "Explanation" column 7, contents of amendment 1, and claims are amended as shown in the attached sheet.

2. The specifications 'a, page 5, lines 1 to 3 are amended as follows.

(In the formula, R and R2 are each hydrogen or methyl group.

The layer is an integer of 0 to 3, and n is an integer of θ to 2) J3, insert the following sentence after the 7th line from the bottom of page 5 of the specification.

By copolymerizing these II-mers represented by general formula [1], the dyeability can be increased to 4 without reducing the refractive index.
can be impregnated with. J (In the second line from the bottom of page 8m5 of the specification, after "99% duplicates", the monomer represented by the general formula [I] is written as 1 to 30%)
Insert 1.

Amended Claims: At least one member selected from dimethallyl orthophthalate, dimethallyl inphthalate, and dimethallyl terephthalate and the general formula [1] (wherein R and R2 are each hydrogen or methyl group.

The layer is an integer of θ~3, and n is g of θ~2! A plastic lens material characterized by having a refractive index of 1.55 or more, which is obtained by copolymerizing a monomer represented by the following formula or a mixture thereof.

Claims (1)

[Claims] 1) At least one member selected from dimethallyl orthophthalate, dimethallyl isophthalate, and dimethallyl terephthalate and the general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] (in the formula R is hydrogen (or methyl group, m and n are 0, 1
or 2) or a mixture thereof, the plastic lens material having a refractive index of 1.55 or more.