JPH06289334A - Lens having extremely high dyeability - Google Patents

Abstract

PURPOSE:To provide the lens having excellent dyeability by subjecting a specific monomer, a specific crosslinking agent and a monomer copolymerizable therewith to radical cast polymn. molding. CONSTITUTION:This lens is obtd. by subjecting 30 to 80 pts.wt. monomer expressed by formula I, 10 to 50 pts.wt. crosslinking agent expressed by formula II and 10 to 50 pts.wt. copolymerizable therewith to the radical cast polymn. molding. In the formula, X denotes H, CH3 group; n denotes an integer from 2 to 8. The resin obtd. by the compd. of the formula I alone is highly hydrophobic and is not the material having the desired extremely high dyeability. The limited number of polyethoxy groups expressed by the formula II are incorporated into the resin, by which the material is made sufficiently soft and hydrophilic. Consequently, a relatively high refractive index is obtd. and dyes are diffused easily in a hot bath dispersed with the disperse dyes. The dyeing up to a relatively high density is thus possible.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a highly dyeable lens.

[0002]

2. Description of the Related Art Generally, a resin material used for an eyeglass lens is required to be light, strong and highly dyeable. In particular, the dyeability, which is a property that cannot be obtained by conventional glass materials, is an essential and extremely important property that resin materials used as spectacle lenses should have. In particular, there are many cases where dyeing is required until the transmittance in the visible light wavelength range falls below 20%. Among the resin materials conventionally used as spectacle lenses, diethylene glycol-
Rubisallyl carbonate shows excellent dyeability and is currently the most frequently used resin for eyeglass lenses.
However, the resin obtained by polymerizing the above diethylene glycol bisallyl carbonate has a low refractive index of 1.5
Since it is 0, there is a defect that the dent of the concave lens becomes extremely thick when used as a spectacle lens. Therefore, a plastic material having a high refractive index is strongly desired. However, materials with a high refractive index generally tend to be highly aromatic and hydrophobic. Generally, a method of dyeing a lens is to disperse a disperse dye in water and heat the dispersion. Therefore, in general, a material having a large aromaticity and a hydrophobicity and a high refractive index tends to be difficult to dye. From this point of view, there is a strong demand for a plastic eyeglass material having a relatively high refractive index and a high dyeability.

[0003]

SUMMARY OF THE INVENTION The present invention meets the above demands and provides a useful lens of a plastic eyeglass material having a relatively high refractive index and a highly dyeable material. With the goal.

[0004]

The present invention is directed to a monomer represented by the following chemical formula 3 [Structural Formula (1)] having a specific aromatic group and a limited number of ethoxy groups, and the structural formula (1) The following chemical formula 4 containing more ethoxy groups than the monomer shown in 1)
It is characterized in that a monomer mixture containing a crosslinking agent represented by [Structural Formula (2)] as a main component is subjected to radical cast polymerization.

The plastic spectacle material of the present invention is obtained by radical casting polymerization of a specific monomer. As the monomer used in the present invention, the following specific monomers are used. That is, a structure containing more ethoxy groups than the dimethacrylic ester represented by the following structural formula (1) having a specific aromatic group and a limited number of ethoxy groups and the monomer represented by the structural formula (1). Formula (2)
The main component is a bifunctional methacrylic ester represented by.

[0006]

[Chemical 3]

[0007]

[Chemical 4]

In the present invention, the reason why methacrylic ester having a bisphenol A type aromatic group and a polyethoxy group in the structural formulas (1) and (2) is used is bisphenol A type. This is because the spectacle material of the present invention has a relatively high refractive index by containing the aromatic group. Further, the reason for having a polyethoxy group is that the dye particles are allowed to move freely and the dyeing property is highly achieved by making the material partially flexible and hydrophilic. Therefore, compared with conventional eyeglass materials, the refractive index is relatively high, and the dye easily diffuses in a warm bath in which the disperse dye is dispersed, and a useful plastic that enables dyeing to a relatively high concentration. It becomes possible to make a spectacle material made of.

In this sense, the compound of structural formula (1) is
In particular, it is used for the purpose of increasing the refractive index. However, the resin obtained only by the compound of the structural formula (1) is not a highly hydrophobic material and does not serve as a desired highly dyeable material. In order to overcome this drawback, the present invention makes the material sufficiently flexible and hydrophilic by containing a limited number of polyethoxy groups of structural formula (2), resulting in a relatively High refractive index,
Further, the dye easily diffuses in a warm bath in which the disperse dye is dispersed, and it becomes possible to provide a useful plastic eyeglass material which enables dyeing to a relatively high concentration. From this meaning, the content of the polyethoxy group in the compound of the structural formula (2) is limited. That is, when the content of the polyethoxy group is large, it is advantageous for improving the dyeability by increasing the hydrophilicity, but as the content of the polyethoxy group is increased, the refractive index of the copolymer is lowered, It becomes soft and the heat resistance of the resin tends to decrease. Therefore, in the present invention, the content of the polyethoxy group in the compound of structural formula (2) is an integer of 2 to 8. When the number of n exceeds 8, the refractive index of the copolymer is significantly lowered and the resin becomes flexible and the heat resistance of the resin is lowered. Therefore, in the present invention, n is preferably an integer of 2 to 8 as a preferable range. .

The monomer of the present invention is the compound (1)
In addition to (2) and (2), monomers copolymerizable with these compounds (1) and (2) can be used as a copolymerization partner. The purpose of using this copolymerizable monomer is to adjust the polymerization rate of the copolymer, to adjust the monomer viscosity to a viscosity suitable for radical casting polymerization, or to adjust the moldability, It is used for various purposes such as adjusting the refractive index of the resin. Specific examples of the monomer as the third component include various methacrylic esters such as methyl methacrylate, butyl methacrylate, phenyl methacrylate, isobutyl methacrylate, styrene, and chloro. Examples include various vinyl compounds such as styrene, bromostyrene, α-methylstyrene, and divinylbenzene. These are just examples and the present invention is not limited thereto.

Next, the ratio of the compounds (1) and (2) as the monomer component used in the present invention and the third component is 30 to 80 parts by weight of the compound (1) and the compound (2) 10.
˜50 parts by weight, 10 to 50 parts by weight of the third component are used as appropriate ranges. When the amount of the compound (1) monomer is less than 30 parts by weight, the spectacle material of the present invention cannot obtain a sufficiently high refractive index. Further, if it exceeds 80 parts by weight, a relatively high refractive index can be obtained, but it becomes a material having extremely poor dyeability. Next, if the amount of the compound (2) used is less than 10 parts by weight, the material will not be highly hydrophobic and will not be the desired highly dyeable material. If it exceeds 50 parts by weight, the dyeability is improved but the refractive index of the copolymer is significantly lowered. From this meaning, in the present invention, the monomer amount of the compound (2) is 10
-50 parts by weight is used as a preferred range. The third component monomer is 10 to 50 depending on the purpose of use.
By using it in the range of parts by weight, a good eyeglass material can be obtained. For the above reasons, the monomer raw material of the spectacle material of the present invention contains 30 to 80 parts by weight of the monomer represented by the compound (1) and the crosslinking agent 20 represented by the compound (2).
˜50 parts by weight and 20 to 50 parts by weight of the third component monomer are used as a suitable composition.

Next, a specific method for producing the eyeglass material of the present invention will be described. As mentioned above, the resin of the present invention is obtained by radical casting polymerization. First, a specific monomer composition within the scope of the present invention is mixed, and a radical polymerization initiator is further added to prepare a uniform monomer solution.
This monomer solution is poured into a mold (mold) made of glass, various plastics, or metal, and radical polymerization is started at room temperature or under heating to obtain a desired shape. It is possible to obtain a molded eyeglass material.

The radical polymerization initiator is not particularly limited, and an initiator usually used for radical polymerization can be used. The polymerization temperature is generally in the range of room temperature to 120 ° C. The molded product thus obtained can be used as it is as a spectacle lens, but can also be processed into various optical materials by means such as cutting and polishing depending on the application. Further, dyeing, hard coating, anti-reflection coating and the like are also effective means. The spectacle material of the present invention thus obtained provides a spectacle material having a relatively high refractive index and excellent dyeability as compared with the conventional glass and plastic spectacle materials. In the above description, the radical polymerization was described, but the polymerization is not limited to radicals, and photopolymerization or radiation polymerization is also possible. Next, further description will be given in the examples.

[0014]

【Example】

Example (1) 55 parts by weight of 2,2-bis [4- (methacryloxy.ethoxy) phenyl] propane 2,2-bis [4- (methacryloxy.triethoxy) phenyl] propane 30 parts by weight 15 parts by weight of α-methylstyrene Was thoroughly mixed, and 1.0 part by weight of lauroylperoxide was further dissolved therein to obtain a monomer solution. This was injected into a glass mold fixed with a gasket, and polymerization was performed under the following conditions. 50 ° C. 16 hours 70 ° C. 4 hours 90 ° C. 2 hours The molded body after polymerization had a thickness of 1.6 mm and diopter-0.2.
It was 5. It is colorless and transparent and has a visible light transmittance of 90.
%showed that. (Visible light transmittance is measured by ASTM D
According to the method of 1003-52. ) Further, the refractive index of this material was 1.548, which was a relatively high value. Next, the dyeability of this molded article was tested. The test method is BPI
One GRAY dye manufactured by Kuraray Co., Ltd. was dissolved in 950 ml of pure water, the temperature of this aqueous solution was raised to 90 ° C., the molded body was dipped in this aqueous solution for 10 minutes, taken out, thoroughly washed with water, and then the visible light transmittance. Then, a dyeability test was conducted. The visible light transmittance of the molded product of Example (1) after the dyeing test was 40%, which confirmed that the dyeing property was excellent.
Next, the lens of Example (1) was subjected to a hard coat and an antireflection coat under the following conditions. Hard coating agent: TS56 manufactured by Tokuyama Soda Co., Ltd.
T (silicon-based hard coat agent) Coating method: Dipping method Curing condition: 110 ° C. 2 hours A hard coat film having a thickness of 5.1 μm was formed by the above method. Antireflection co - to form an antireflection film of Si0 ₂ / Zr0 ₂ based seven layers by preparative sputtering. When this lens provided with a hard coat and an antireflection coat was kept at 80 ° C. for 30 minutes, it was confirmed that there was no change in cracks and the like, and that this lens also had excellent heat resistance. Comparative Example (1) Used in Example (1) 2,2-bis [4- (methacryloxy.ethoxy) phenyl] propane 85 parts by weight 2,2-bis [4- (methacryloxy.triethoxy) phenyl] propane 0 part by weight 15 parts by weight of α-methylstyrene was thoroughly mixed, and polymerization was carried out under the same conditions as in Example (1) to obtain a diopter-0.25 concave lens. It was colorless and transparent and had a visible light transmittance of 90%. The refractive index of this material was 1.556, which was a relatively high value. However, the visible light transmittance of the molded article of Comparative Example (1) after the dyeing test was
It was 83% and it was recognized that the dyeability was extremely difficult.

Example (2) 2,2-bis [4- (methacryloxyethoxy) phenyl] propane 55 parts by weight 2,2-bis [4- (methacryloxypolyethoxy) phenyl] represented by the following structural formula 5. 30 parts by weight of propane

[0016]

[Chemical 5]

15 parts by weight of α-methylstyrene was mixed well, and 1.0 part by weight of lauroylperoxide was further dissolved therein to obtain a monomer solution. This was injected into a glass mold fixed with a gasket and polymerization was performed under the same conditions as in Example (1) to obtain a lens having a thickness of 1.6 mm and diopter-0.25.
This material is colorless and transparent, and has a visible light transmittance of 90.
%showed that. The refractive index of this material was 1.543, which was a relatively high value. It was confirmed that the visible light transmittance after the dyeing test carried out by the method according to Example (1) was 32% and the dyeing property was excellent. Further, when this lens provided with the hard coat and the antireflection coat, which was produced by the method according to Example (1), was maintained at 80 ° C. for 30 minutes, there was no change in cracks and the like. It was confirmed that the heat resistance was also excellent.

[0018]

The spectacle lens material of the present invention has a relatively high refractive index as compared with the conventional spectacle materials, and the dye easily diffuses in a warm bath in which the disperse dye is dispersed, so that the concentration is relatively high. Moreover, the present invention provides a useful plastic spectacle material that enables dyeing.

Claims (1)

[Claims] 1. A monomer of 30 to 80 parts by weight represented by the following chemical formula 1 [Structural formula (1)], 10 to 50 parts by weight of a crosslinking agent represented by the following chemical formula 2 [Structural formula (2)], and these. A highly dyeable lens obtained by radical-cast polymerization molding of 10 to 50 parts by weight of a copolymerizable monomer. [Chemical 1] [Chemical 2]