JPS58168614A - Resin for plastic lens - Google Patents

Abstract

PURPOSE:The titled resin for high-refractive index spectacles, prepared by addition-polymerizing a vinyl monomer capable of providing a polymer having a refractive index of above a specified value with a mixture containing an isocyanate compound and a hydroxyl group-containing vinyl monomer at a specified ratio. CONSTITUTION:The following components are mixed together and subjected to addition polymerization: (A) 20-80wt% vinyl monomer capable of providing a polymer of refractive index >=1.55, e.g., diallyl phthalate, and (B) 20-80wt% mixture containing an isocyanate compound (e.g., xylylene diisocyanate) and a hydroxyl group-containing vinyl monomer (e.g., 2-hydroxyethyl acrylate) and having an NCO/OH molar ratio of 0.5-2.0 (if necessary, a hydroxyl group-containing compound other than the above, e.g., trimethylolpropane, may be added). The titled resin capable of providing a high refractive index is obtained from the above produced polymer.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a resin for eyeglass plastic lenses.

Plastic lenses have the advantage of being easier to manufacture than glass lenses, and are also lightweight and have good impact resistance, making them highly safe when used in eyeglass lenses. Conventional plastic lens resins include acrylic resin, polycarbonate resin, allyl diglycol carbonate resin, and polystyrene resin. Among these, which plastic lenses are widely used for vision correction glasses.

Diethylene glycol bisallyl carbonate is a thermosetting resin. This resin has excellent impact resistance, and the lens power does not change significantly with changes in temperature.
Furthermore, it has various features such as good machinability and workability.

However, diethylene glycol bisallyl carbonate has a refractive index of 1.50, and when a lens is made from this resin, it has the disadvantage that the lens is thicker than a glass lens. This is particularly noticeable when the lens power increases.

In particular, in recent years, there has been a demand for plastic lenses to be smaller and thinner, and there has been a need for resins for plastic lenses that have a high refractive index that makes this possible.

The inventors of the present invention solved the above-mentioned problems and conducted extensive studies on resins for plastic lenses that provide a high refractive index, and as a result, they arrived at the present invention described below.

That is, the present invention relates to a 41 resin for plastic lenses characterized by comprising a polymer obtained by addition polymerizing a composition consisting of a 9th-order A component and a B component.

A: Vinyl monomer that provides a polymer with a refractive index n2J of 1.55 or more 20 to 80% by weight B: Consisting of an incyanate compound and a vinyl monomer containing a hydroxyl group, the molar ratio of NC010H Composition such that 0.5 to 2.0 20 to 80
The A component in the weight-related material is used for the purpose of imparting a high refractive index. Therefore, the vinyl monomer used as component A has a refractive index n2D of a polymer of the vinyl monomer. is required to be 1.55 or more. Usually, there are many vinyl monomers containing aromatic rings and halogen elements other than fluorine, and specific examples include the following.

Diallylchlorendate Dimethallylchlorendate Ethyl chlorendate diacrylate Ethyl chlorendate dimethacrylate Probyl chlorendate diacrylate Glopyl chlorendite dimethacrylate Styrene a-methylstyrene Chloromethylstyrene diaryl Phthalate Dimethallyl phthalate Triallyl trimellitate Grindyl styrene Iodide Styrene Divinylbenzene 2.3-Dipromoglobyl acrylate Tetrabromobisphenol A-Bisallyl ether Tetra 7'0-E'''''xy,''' Meno 1- ．?
2Metal 1L etherTetrabromobisphenol A-bisacrylateTetrabromobisphenol A-bismethacrylate 1B component has various performances required for eyeglass lenses.

For example, it is used to improve mechanical properties such as impact resistance and bending elasticity, as well as machinability and polishability.

0) incyanate compound in component B.

Both aromatic and aliphatic types can be used.9 Examples include the following.

Hexamethylene diisocyanate inphorone diisocyanate 2,2,4-trimethylhexamethylene diisocyanate dicyclohexylmethane diisocyanate lysine diisocyanate methyl ester Cyanates can also be used.

Biuretization reaction product of hexamethylene diisocyanate Reaction adduct of hexamethylene diisocyanate and trimethylolpropane 2-incyanate ethyl-2,6-diycyanatoethylhexanoate 1,6.11-undecane triisocyanate isophorone diisocyanate Reaction adduct with trimethylolpropane Reaction adduct between xylylene diinocyanate and trimethylolpropane Reaction adduct between bis(isocyanatomethyl)cyclohexane and trimethylolpropane Among the above isocyanate compounds, particularly preferred are xylylene diinocyanate and trimethylolpropane. These include diisocyanate, inphorone diisocyanate, and bis(incyanate methyl)cyclohexane.

Examples of the ←) hydroxyl group-containing vinyl monomer in component B include the following compounds.

acrylic acid-2-hydroxyethyl acrylate-2-hydroxyglopyl methacrylate-2-human, loxethyl methacrylate-2-hydroxyglobil methacrylate-5-hydroxyglopyl methacrylate-2-hydroxy -3-
Chloropropyl allyl alcohol Metaallyl alcohol Among the above vinyl monomers, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, and 2-hydroxyethyl methacrylate can be used.

Ethylene Glycol Propylene Glycol Butylene Glycol Polyethylene Glycol Polypropylene Glycol 1,4-Cyclohexa/Dimethanol Glycerin Trimethylol Glonone 1,2,6-Hexandriol Dibromoneopentyl Glycol Tripromoneopentyl Alcohol Tetrapromo Bisphenol A Ethylene oxide adducts, other polybasic acids such as adipic acid, phthalic anhydride, isophthalic acid, and ethylene glycol.

Polyester polyol synthesized by condensation reaction with diols and triols such as trimethylolbrono ζ. Acrylic esters or methacrylic esters containing these and acrylic polyols prepared by copolymerizing these can also be used.

The amount of A-B components used must be in the range of 20 to 80% by weight. If the amount of the A-B component used is less than 20% by weight, it will not be possible to satisfy various physical properties such as impact resistance and bending elasticity required for eyeglass lenses, while if it is more than 80% by weight, the high refractive index will not be satisfied. Therefore, the object of the present invention cannot be achieved.

What is the proportion of each of components (00) (b) and (c) in component B?

The NC010H molar ratio is adjusted to fall within the range of 0.5 to 2.0. If it deviates from this range, the mechanical properties and workability such as machinability and polishability, which are the intended uses of component B, will be poor.

A general explanation of the method for manufacturing a plastic lens using the resin for plastic lenses of the present invention is as follows.

Manufacturing methods are broadly divided into cast polymerization and injection molding.

The feature of the cast polymerization method is that it directly polymerizes and hardens the raw material monomer and simultaneously forms it into a lens shape. Therefore, the lenses have the characteristics of little molding distortion and excellent optical uniformity, and it is said that most prescription lenses made of plastic on the market are currently manufactured using this method.

On the other hand, the injection molding method is a method in which pre-polymerized resin is injected into the shape of a lens, and methacrylic resin or polycarbonate resin is manufactured using this method for sunglasses and glasses. In injection molding, it is necessary to ensure that the lens molded product has little optical molding distortion, and mold design and molding condition settings are important issues.

For example, to specifically explain the case of the cast polymerization molding method, the A-B components 2 of the present invention are mixed, a normal polymerization initiator is added, the reaction is preliminarily allowed to proceed to some extent (prepolymerization), and air etc. This method involves vacuum degassing the dissolved gas, pouring the wood into a mold, and polymerizing it by heating.

It is preferable to carry out the reaction at a relatively low temperature (for example, 40 to 50°C) at the beginning, and then increase the temperature to about 110°C as one reaction progresses to carry out slow addition polymerization in order to reduce distortion of the lens.

Various known polymerization initiators can be used, but should be selected depending on the desired reaction temperature. For example, 1.1-azobiscyclohexane carbonate, diisopropyl peroxycarbonate, 1.1'-azobiscyclohexane nitrate, di-tert-butyl peroxide, and the like are suitable.

The plastic lens containing the resin of the present invention as a resin component has the following characteristics compared to commercially available plastic lenses.

1. A strong plastic lens can be obtained.

2. Excellent impact resistance.

3. A colorless and transparent resin is obtained.

4. The shrinkage rate during molding polymerization is relatively small. 5. The isocyanate compound and the hydroxy compound can be selected as appropriate, thereby allowing the optical properties to be adjusted freely.

6. High refractive index Z: Excellent bending elasticity.

Plastic lenses containing the resin of the present invention as a resin component are used for surface modification such as antireflection, high hardness, abrasion resistance, improved chemical resistance, and antifogging properties.

It is possible to apply known physical or chemical methods.

The present invention will be explained in more detail with reference to Examples below.

Note that the refractive index in one example is the value at the D line with a wavelength of 5892.9X.

Example 1 50 parts by weight of diallyl phthalate, 23 parts by weight of xylylene diisocyanate, 24 parts by weight of 2-hydroxyethyl acrylate, 6 parts by weight of trimethylolpropane, di-tert-butyl peroxide as a radical polymerization initiator, and the above mixture. Add 1% by weight to the total amount, pour into a lens mold, heat at 50°C for 6 hours, further react at 80°C for 6 hours, at 100°C for 15 hours, and finally add 1% by weight to the total amount.
Heat treatment was performed at 10°C for 1 hour.

The obtained resin had a high refractive index of 1.57 at 20° C., was extremely tough, and was colorless and transparent.

Example 2 Diallyl phthalate 30 parts by weight 2-hydroxyethyl acrylate 20 j Bisphenol A 19 After heating the above mixture to 50°C to form a uniform solution.

31 parts by weight of xylylene diincyanate was added and heated at 50°C for 6 hours. Thereafter, the mixture was cooled to room temperature and the following polymerization initiator was added.

Di-tθrt-butyl peroxide 0.5 parts by weight The solution thus prepared was poured into a lens mold.

A curing reaction was performed by heating at 70°C for 10 hours and at 100°C for 10 hours.

The molded resin obtained was colorless, transparent, hard, and extremely tough. The refractive index nD at 20°C is as high as 1.58 (Ab
The be number was 36.

Example 3 Diallyl phthalate 60 parts by weight 2-hydroxyethyl acrylate 18 Tetrabromobisphenol A 25 After the above mixture was made into a homogeneous solution.

27 parts by weight of isophorone diincyanate was added and heated at 50°C for 6 hours, then cooled to room temperature, and the following polymerization initiator was added.

Di-tert-butyl peroxide 05 parts by weight The solution thus prepared was poured into a lens mold.

A curing reaction was carried out by heating at 70°C for 10 hours and then at 100°C for 10 hours.

The molded resin obtained was colorless, transparent, hard, and extremely tough. The refractive index nD at 20°C is as high as 1.60 (Ab
The be number was 63.

Example 4 Diisopropyl peroxycarbonate was added as a radical polymerization initiator to 75 parts by weight of diallyl chlorendate, 13 parts by weight of xylylene diisocyanate, 10 parts by weight of 2-hydroxyethyl acrylate, and 2 parts by weight of trimethylolpropane.

Add 2% by weight to the above mixture, pour into a lens mold, and heat at 40°C for 10 hours and at 60°C for 10 hours.

Heat treatment was performed at 100°C for 60 minutes.

The obtained copolymer molded product has a high refractive index of 1.56.
The transparency was excellent, and the impact resistance and bending elasticity were also good.

Patent Applicant Higashi Shi Co., Ltd. Company Procedures Amendment Yu Showa Naoki 7.4 掬0 Japan Patent Office Civil Government Haruki Shimada 1, Indication of Case 1982 Patent Application No. 51896 2, Title of Invention For Plastic Lenses Resin 5. Number of inventions increased by amendment None 6. Specifications subject to amendment - middle [Claims] - and "Detailed Description of the Invention".

7. Contents of amendment, j≧, Description (1) First truth The statement in the "Scope of Claims" column is amended as shown in the attached sheet.

(2) Page 3, lines 10-11 "Composition" is corrected to "E mixture".

Attachment Claim (1) Addition of a composition consisting of the following A component and 8 components -
A resin for plastic lenses characterized by comprising a polymer obtained by combining.

A: Vinyl monomer that provides a polymer with a refractive index n of 1.55 or more 20 to 80% by weight B: Consisting of an isocyanate compound and a vinyl monomer containing a hydroxyl group,
and 11 luster 20-80 weight% such that the molar ratio of NGOloH is 0.5-2.0

Claims (1)

[Claims] (1) A resin for plastic lenses characterized by comprising a polymer obtained by addition polymerizing a composition comprising the following components A and B. A: Vinyl monomer that provides a polymer with a refractive index n of 155 or more 20 to 80% by weight B: Consisting of an isocyanate compound and a vinyl monomer containing a hydroxyl group, and the molar ratio of NCQ/DH 20 to 80% by weight of a composition such that 05 to 2.0