JPH0798441A - Production of resin for high-refractive-index lens - Google Patents

Abstract

PURPOSE:To produce a resin for a highly efficient lens having a refractive index ND ranging from 1.57 to 1.60 by using an easily available monomer capable of being polymerized at a moderately high rate as the quantitative main raw material and copolymerizing the monomer with a refractive index improving monomer. CONSTITUTION:A diacrylate shown by the formula (where R is H or CH,, m>=1, n>=1 and 4>m+n>=6) and/or a dimethacrylate are used as the main raw material, triphenylvinylsilane is added as a monomer to improve the refractive index, further another well-known monomer with the refractive index of the homopolymer being >=1.55 is added, as required, and the mixture is radicalcopolymerized to produce a novel resin for a high-refractive-index lens.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION The present invention provides copolymerization of a specific monomer having a silicon atom in the molecule,
The present invention relates to a method for producing a new resin for a high refractive index lens.

[0002]

2. Description of the Related Art As a thermosetting resin for lenses, a resin obtained by casting polymerization of diethylene glycol bisallyl carbonate has been used for a long time, but its refractive index N _D is 1.
50 and the refractive index N _D 1.5 of the crown glass lens
It is lower than 2 to 1.53, and the lens using this resin has a drawback that the thickness rapidly increases as the number of altitudes increases.

[0003] Thermoplastic resins, high refractive index as polystyrene and polycarbonate _(N D _1.58~
1.59), but they are fusible, soluble, and plastic and therefore unsuitable for the following applications. That is, when framing like a spectacle lens, it is necessary to cut and polish the periphery of the lens, and it is tightened by a spectacle frame. Furthermore, one side of a semi-finished lens is rubbed to make a lens of a special power. It is not suitable for operations such as high-speed cutting and polishing with a processing machine, and it must be a thermosetting resin.

Based on such thinking, many studies have been conducted on the development of thermosetting resin for high refractive index lenses,
Many patent applications have been filed. Among them, what is currently regarded as important is one having a refractive index N _D in the vicinity of 1.59 to 1.60, which includes bisphenol A or a similar compound containing 2 or more halogens, especially bromine atoms. In particular, a high-refractive-index resin whose main component is a monomer having a skeleton obtained by adding 4 units. (Japanese Patent Publication No. 62-25162, Japanese Patent Publication No. 2-15841, Japanese Patent Publication No. 3)
-19521, Japanese Patent Publication No. 3-20721) A high refractive index resin obtained by mainly utilizing a reaction (urethane forming reaction) between an isocyanate compound and a hydroxyl compound or a thiol compound. (JP-A-57-136601, 57-136602, 5)
9-133211, 60-11513, 60-24
9101, 62-73201, 64-26622,
64-54021, JP-A-1-185501, 2-
153302)).

Further, a technique attracting attention for a material having a refractive index N _D in the vicinity of 1.56 to 1.57 (herein referred to as a quasi high refractive index resin) is a quasi high refractive index resin containing diallyl phthalates as a main component. . (Japanese Patent Publication 57-42841, Japanese Patent Publication 60-4432)
7, see JP-B-2-39761) Bisphenol A as it is or by adding 4 mol or less of ethylene oxide thereto, and changing the phenolic OH groups to alcoholic OH groups as much as possible, and then converting it into acrylic acid or methacrylic acid ester. A semi-high refractive index resin whose main component is a polymer. (See Japanese Examined Patent Publication No. 58-17527).

[0006]

When producing a resin for a high refractive index lens, the desirable matters are, from the viewpoint of raw materials,
It should be easily available, or the raw materials should be easily synthesized and purified. From the viewpoint of resin quality, it should be colorless and transparent, have optical homogeneity, impact resistance, light resistance and various processability. In terms of factory work, manufacturing operating conditions are not harsh (for example, there are no difficult conditions such as using extremely low or high temperatures, and slight temperature errors are not allowed), and easy release and high yield. Is easy to obtain.

The above-mentioned techniques (1) and (2) satisfy almost all of these desirable requirements except that they have a quasi-high refractive index, whereas the technique (2) requires the cost of producing and purifying the monomer. The problem is that the resin is expensive and the impact resistance and light resistance of the obtained resin are insufficient, and in the case of, the technology has not been solidified yet and the operating conditions are severe, so the yield has reached a satisfactory point. The problem is not. It improves that the therefore and techniques not obtained only sub-high refractive index, if it was possible to increase the high refractive index (around N _D from 1.59 to 1.60), say to give the most desirable method obtain. The present inventors have conducted extensive research to obtain the most desirable method, and arrived at the present invention.

That is, the present invention provides a high refractive index lens characterized by copolymerizing triphenylvinylsilane and one or more kinds of radically polymerizable monomers having a homopolymer refractive index of 1.55 or more. Is a method for producing a resin for use, and more specifically, 3 to 40% by weight, preferably 7 to 30% by weight, of triphenylvinylsilane as the first monomer, and 1 to 3 as the second monomer.

[Chemical 1] (However, R represents hydrogen or a methyl group, and m ≧ 1, n ≧
1 to 20 and 70% by weight of one or a mixture of two or more compounds represented by the formula (1) and m + n represents a number of more than 4 and 6 or less, and a homopolymer having a refractive index of 1 is used as the third monomer. The method for producing a resin for a high refractive index lens is characterized by mixing 0.55 or more of one or more other radically polymerizable monomers and copolymerizing the mixture in an amount of 0 to 40% by weight.

Now, a method for synthesizing the triphenylvinylsilane used in the present invention will be described. Method for synthesizing triphenylvinylsilane: It can be synthesized using the Grignard reaction. As an example, using sufficiently purified tetrahydrofuran as a solvent, vinylmagnesium bromide is allowed to act on triphenylchlorosilane or triphenylsilane, decomposed with a saturated aqueous solution of ammonium chloride, and then triphenylvinylsilane dissolved in tetrahydrofuran is recovered. Then, it was purified by vacuum distillation in the presence of a polymerization inhibitor and a trace amount of nitrogen gas. It is a colorless and transparent liquid. (When triphenylsilane is used as a raw material, a small amount (for example, about 5 to 10%) of the raw material substance may remain in the synthesized triphenylvinylsilane. However, it may substantially affect the performance of the lens resin of the present invention. Does not have a significant effect.)

Triphenylvinylsilane shows good compatibility with acrylic acid esters and methacrylic acid esters having a benzene nucleus, styrenes, divinylbenzenes, etc., and the mixed composition of monomers, polymerization conditions (polymerization initiation) By appropriately selecting the type and amount of the agent, the polymerization temperature-one hour curve, etc.), it is possible to copolymerize well to form a high quality high refractive index lens resin.

Regarding the amount of triphenylvinylsilane used, even if it is 3% by weight of the total monomer weight, it has the effect of pushing up the refractive index, but when it is used in an amount of preferably 7% by weight or more, the refractive index obviously increases. , Proved to be more effective. The maximum is 40% by weight. If it exceeds this value, the obtained resin may exhibit a decrease in rigidity at a high temperature, for example, around 100 ° C, which is unsuitable for a lens or the like that is dyed at around 100 ° C. Therefore, preferably 3
It is possible to prevent such a problem from occurring by setting the content to 0% by weight or less and appropriately selecting the composition of the monomer mixture.

When this triphenylvinylsilane is used as a copolymerization component, not only the refractive index can be increased but also the Abbe number can be increased at the same time, and the value can be 40 or more.

In the present invention, as the second monomer,
A diacrylate and / or dimethacrylate having the structure of is used, in which the phenolic OH groups at both ends of bisphenol A are completely converted to alcoholic OH groups by addition of ethylene oxide in excess of 4 moles. However, not only is there no risk of discoloration of the product lens or the like due to the residual phenolic OH groups, but it also significantly contributes to the improvement of impact resistance. The decrease in the refractive index due to the increase in the number of moles of ethylene oxide added is compensated for and further enhanced by the copolymerization with triphenylvinylsilane, and as a result, a new high-index lens copolymer having excellent performance is obtained. This is the reason why you can get a coalescence. If the number of moles of ethylene oxide added exceeds 6, the rigidity of the obtained resin at room temperature will decrease, and it will not be suitable for applications such as lenses, so it is not adopted in the present invention. When the amount of the second monomer used is less than 20% by weight of the total monomer mixture, the impact resistance becomes insufficient, and when it exceeds 70% by weight, the amount of the first monomer decreases. High refractive index cannot be obtained. That is, this is the reason why the content is 20 to 70% by weight.

The third monomer according to claim 2 is the first and second monomers.
It is intended to supplementarily improve the properties of the copolymer of monomers, and examples thereof include phenyl acrylate, phenyl methacrylate, benzyl acrylate, benzyl methacrylate, bisphenol S diacrylate, bisphenol S dimethacrylate, styrene, and chloro. Styrene, divinylbenzenes, 1,3,5-triacryloyl-hexahydro-striazine, o-phenylbenzoic acid allyl ester, p-phenylbenzoic acid allyl ester, biphenyl-2,2'-dicarboxylic acid diallyl ester, bisphenol A Diallyl carbonate, bisphenol S diallyl carbonate, o-phenylphenol allyl carbonate, p-phenylphenol allyl carbonate, diphenyldivinylsilane, benzyl methyl maleate And benzyl methyl fumarate, and the like.

These third monomers are used in an amount of 0 to 40% by weight based on the total monomer mixture. However, since allyl compounds and diphenyldivinylsilane generally have a slower polymerization rate than others, it is necessary to use 20% by weight or less based on the total weight of the monomer mixture to improve the copolymerizability.

A radical polymerization initiator is used when copolymerizing the monomer mixture described above. This includes diisopropyl peroxydicarbonate, di-n-propyl peroxydicarbonate, and dineopentyl purge carbonate, which act effectively at relatively low temperatures (about 30 to 50 ° C.), and medium temperatures (60 to 80). T-butylperoxypivalate, t-butylperoxy-2-ethylhexanoate, t-butylperoxyisobutyrate, etc., which act effectively at about (° C. ), 1,1-bis (t-butylperoxy) -3,3,5
Preferred examples include -trimethylcyclohexane, 1,1-bis (t-butylperoxy) cyclohexane and t-butylperoxy-3,5,5-trimethylhexanoate.

These polymerization initiators may be used alone or in admixture of two or more. The amount used is required to be 0.1 to 5% by weight (in total when two or more polymerization initiators are used) with respect to the total weight of the monomer mixture.

Since the resin for a high refractive index lens produced in the present invention places importance on light resistance, an ultraviolet absorber is added to the monomer mixture during the polymerization. 2- (3,5-
Di-t-butyl-2-hydroxyphenyl) benzotriazole, 2- [2-hydroxy-5- (1,1,3,3
3-tetramethylbutyl) phenyl] benzotriazole and other triazoles, or 2-hydroxy-4-
n-octoxybenzophenone, 2-hydroxy-4-
Good results may be achieved with benzophenone-based compounds such as benzyloxybenzophenone. That is, these ultraviolet absorbers are mixed in an amount of 0.05 to 2% by weight based on the total weight of the monomer mixture. This prevents yellowing and deterioration of physical properties due to aging under the irradiation of sunlight after molding into a lens, and especially when used as a lens for eyeglasses, it blocks ultraviolet rays as much as possible and helps to protect the eyes. To be

In the present invention, the polymerization and molding are usually carried out by using two well-polished and surface-strengthened glass molds and a rubber-like elastic substance (chemically inert to monomers and the like). For example, through a gasket made of ethylene-butadiene copolymer, ethylene-vinyl acetate copolymer, etc.), the gaskets are assembled in parallel, and each of the above-mentioned monomers, polymerization initiators, and UV absorbers are arranged in the space. If necessary, the mixed solution of (a release agent, a yellowing complementary colorant, etc. may be added) is preliminarily polymerized and then injected. Here, the prepolymerization means that the mixed solution is slightly heated and stirred in advance in the presence of a small amount of a polymerization initiator to slightly increase the viscosity of the solution.
(Alternatively, one component or only a few components of the monomer mixture may be separately pre-polymerized and then mixed with other monomers. That is, block copolymerization is performed.) By doing so, It has an effect of preventing the mixed solution from leaking through the gap between the mold and the gasket, and at the same time, reducing adverse effects due to volume contraction during polymerization.

When the injection is completed, the mixture is placed in a heating furnace and polymerized.
The polymerization time is generally 10 to 30 hours, but 15
-20 hours is often suitable for the convenience of operation. As described above, the temperature of the heating furnace should be adjusted in consideration of the fact that the temperature at which it works effectively varies depending on the type of polymerization initiator. For example, when di-n-propylperoxydicarbonate, which acts effectively at a relatively low temperature as a polymerization initiator, is used alone, the temperature rising rate between 30 and 50 ° C. is made as slow as possible, and the maximum polymerization temperature is 90%. ~ 100
It should be kept at 0 ° C. and kept at this temperature for 0.5 to 3 hours so that all of the polymerization initiator is decomposed without remaining in the polymerization product.

If, for example, dineopentyl purge carbonate which acts effectively at a relatively low temperature as a polymerization initiator and t-butylperoxy-2-ethylhexanoate which acts effectively at an intermediate temperature, a relatively high temperature is used. When t-butylperoxy-3,5,5-trimethylhexanoate, which works effectively under
C., 60 to 80.degree. C., and 90 to 110.degree. C. in the respective temperature ranges, the heating rate is made as slow as possible, the heating rate in the middle between them is made relatively rapid, and the maximum polymerization temperature is set to 120.degree. The temperature should be maintained for 0.5 to 3 hours so as to decompose any excess polymerization initiator.

When the polymerization is completed, the polymer is released from the mold. Mold release is usually performed at a high temperature, but in some cases, it is better to perform at a low temperature. First remove the gasket,
The polymer is then mechanically removed from the mold. The polymer of the present invention can be released from the mold without using a special mold release agent. (The process from the injection of a mixed solution of monomers etc. into a mold to the release is called cast polymerization.)

After releasing the mold, heat treatment is performed. Normally, put in a heating furnace at a temperature 5 to 10 ° C higher than the maximum polymerization temperature and
Heat treatment is performed at the temperature for 0 minutes to 2 hours. This makes it possible to eliminate the internal strain of the polymer generated during the polymerization or the mold release. (It is necessary to perform the heat treatment even after the rough polishing of the next semi-finished lens and the subsequent polishing.)

The lens produced by the above operation can be put to practical use as a product as it is, but by casting polymerization, a semi-finished lens is first made, and the rear surface of this is rough-polished and polished to obtain the desired degree of product lens. Can also be It was confirmed that the polymerized molded product of the present invention is well suited for such rough sliding and polishing steps and can be made into an excellent product without melting or roughening of the polished surface.

Further, the resin for lenses according to the production method of the present invention can be well dyed with a disperse dye in a dyeing bath at 80 to 95 ° C., and a hard coating film of organic or silicon-containing type can be strongly dyed. It was found that the solid deposition of SiO ₂ and metal oxide was basically possible in a vacuum deposition apparatus.

In order to describe the present invention more specifically and in detail, the following examples are shown. However, the present invention is not limited to these examples. The test methods for various physical properties shown in the examples are as follows. 1) Refractive index N _D : Measured using an Abbe refractometer.
Monobromnaphthalene was used as the contact liquid. 2) Abbe number ν _D : Same as above 3) Pencil hardness: Measured according to JIS (K5400). 4) Impact resistance: FD on resin plate for lens with thickness of 2mm
A steel ball drop test conforming to the A standard was carried out, and those that did not crack were rated good. 5) Light resistance: An irradiation test was carried out for 200 hours in an ultraviolet irradiation tester, and those having no coloring, that is, yellowing were regarded as good. (The polystyrene and polycarbonate tests carried out for comparison showed yellowing and were unsatisfactory.) 6) Dyeability: Dipping for 15 minutes in a disperse dyeing bath at 90 ° C. to see if dyeing to a medium density Tested and accepted what was possible.

[0027]

Example 1 25 parts by weight of triphenylvinylsilane,
2,2-Bis (acryloxy-poly (4.2) ethoxy-phenyl) propane [Note: Poly (4.2) ethoxy represents a total of 4.2 mol polymerizing groups of ethylene oxide. Same below] 55 parts by weight, bisphenol S diacrylate 15
To a monomer mixture consisting of 10 parts by weight of m-divinylbenzene and 2- [2-hydroxy-5- (1,1,3,3-tetramethylbutyl) phenyl] benzotriazole as an ultraviolet absorber was added. 3 parts by weight was added and dissolved, and 0.8 parts by weight of dineopentyl purge carbonate and 0.8 parts by weight of t-butylperoxy-2-ethylhexanoate as a radical polymerization initiator were added and dissolved, and the polymerization was performed. The mixed solution was poured at room temperature into a space formed by two surface-reinforced glass flat plate molds (distance: 2 mm) and a gasket made of an ethylene-butadiene copolymer, and cast polymerization was carried out.

The temperature-time curve for cast polymerization is 30 ° C.
From 50 to 50 ° C with a gentle slope over 8 hours,
Temperature rises rapidly from 50 ° C to 65 ° C in 2 hours,
From 5 ℃ to 85 ℃, the temperature rises slowly over 5 hours,
The temperature rises rapidly from 85 ° C to 100 ° C in 2 hours,
Then, heating was continued at 100 ° C. for 2 hours to terminate the polymerization. When heated, the gasket was removed, and the resin plate was mechanically released from the mold flat plate. Release was relatively easy. This resin plate was heat-treated at 105 ° C. for 1 hour to remove the internal strain. The heat-treated resin plate was colorless and transparent, and had a high refractive index and a low dispersion (ν _D 44). The test results are shown in Table 1.

[0029]

Example 2 Instead of the monomer mixture used in Example 1,
20 parts by weight of triphenylvinylsilane, 2,2-bis (acryloxy-poly (4.2) ethoxy-phenyl)
A monomer mixture consisting of 55 parts by weight of propane, 18 parts by weight of bisphenol S diacrylate and 7 parts by weight of m-divinylbenzene was used, and the radical polymerization initiator was t-butylperoxy-2-ethylhexanoate 1.5 parts by weight. The temperature-time curve at the time of cast polymerization was gradually increased from 12 ° C. to 85 ° C. over 12 hours, and from 85 ° C. to 105 ° C. at a rapid rate of 3%. The temperature was raised over a period of time, heating was continued at 105 ° C. for 2 hours to terminate the polymerization, and after mold release, heat treatment was performed at 110 ° C. for 1 hour. The other operating method was the same as in Example 1 except that a resin plate was prepared. This product was colorless and transparent, had a high refractive index and low dispersion (ν _D 41). The test results are shown in Table 1.

[0030]

Example 3 Instead of the monomer mixture used in Example 2,
25 parts by weight of triphenylvinylsilane, 2,2-bis (acryloxy-poly (4.2) ethoxy-phenyl)
A resin plate was prepared under the same conditions as in Example 2 except that a monomer mixture consisting of 45 parts by weight of propane, 10 parts by weight of bisphenol S diacrylate and 20 parts by weight of phenyl methacrylate was used. It was colorless and transparent, had a high refractive index and low dispersion (ν _D 44). The test results are shown in Table 1.

[0031]

Example 4 Instead of the monomer mixture used in Example 1,
32 parts by weight of triphenylvinylsilane, 2,2-bis (acryloxy-poly (4.2) ethoxy-phenyl)
Using a monomer mixture consisting of 48 parts by weight of propane, 12 parts by weight of bisphenol A diallyl carbonate and 8 parts by weight of m-divinylbenzene, injection was carried out at a warm temperature, and the radical polymerization initiator was t-butylperoxy-2-ethylhexa. 1.5 parts by weight of noate and 1.2 parts by weight of 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane were added, and the temperature-time curve for the cast polymerization was 55. The temperature rise from ℃ to 80 ℃ is performed slowly over 8 hours, the temperature rises rapidly from 80 ℃ to 95 ℃ in 2 hours, and rises slowly from 95 ℃ to 110 ℃ over 5 hours. Warm to 110 ° C. to 120 ° C. in 1.5 hours, and rise rapidly at 120 ° C.
Polymerization was terminated by continuously heating for 5 hours, and after releasing, heat treatment was performed at 125 ° C. for 1 hour. Other procedures were the same as in Example 1, and a resin plate was prepared and tested. The test results are shown in Table 1.

[0032]

EXAMPLE 5 22 parts by weight of triphenylvinylsilane instead of the monomer mixture used in Example 4, 2,2-bis (methacryloxy-poly (4.5) ethoxy-phenyl) propane [Note: poly (4) .5> Ethoxy represents a total of 4.5 moles of ethylene oxide polymerized groups] 55 parts by weight, 15 parts by weight of phenylphenol allyl carbonate and 8 parts by weight of m-divinylbenzene were used as a monomer mixture,
Other than that, a resin plate was prepared and tested under the same conditions as in Example 4. The results are shown in Table 1.

[0033]

[Table 1]

[0034]

As described above, the present invention has a refractive index N _D
Not only in the vicinity of 1.59 to 1.60, but also in a high Abpe number ν _D (that is, low dispersion), and a lot of other excellent properties. It is provided. That is, in the present invention, by using triphenylvinylsilane as a monomer for improving the performance that brings about a high refractive index, 2,2-bis (acryloxy-polyethoxy-
(Phenyl) propane and / or 2,2-bis (methacryloxy-polyethoxy-phenyl) propane are allowed to coexist as main monomers, and a known third monomer is appropriately added thereto to make it suitable for factory operation. It is intended to provide a method for producing a good resin for a high refractive index lens.

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[Procedure amendment]

[Submission date] September 21, 1994

[Procedure Amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0004

[Correction method] Change

[Correction content]

Based on such thinking, many studies have been conducted on the development of thermosetting resin for high refractive index lenses,
Many patent applications have been filed. Among them, what is currently regarded as important is one having a refractive index N _D in the vicinity of 1.57 to 1.60, which includes bisphenol A or a similar compound containing 2 or more halogens, especially bromine atoms. In particular, a high-refractive-index resin whose main component is a monomer having a skeleton obtained by adding 4 units. (Japanese Patent Publication No. 62-25162, Japanese Patent Publication No. 2-15841, Japanese Patent Publication No. 3)
-19521, Japanese Patent Publication No. 3-20721) A high refractive index resin obtained by mainly utilizing a reaction (urethane forming reaction) between an isocyanate compound and a hydroxyl compound or a thiol compound. (JP-A-57-136601, 57-136602, 5)
9-133211, 60-11513, 60-24
9101, 62-73201, 64-2662
2, the same 64-54021, JP-A-1-185501, and the same 2-153302).

[Procedure Amendment 2]

[Document name to be amended] Statement

[Correction target item name] 0007

[Correction method] Change

[Correction content]

The above-mentioned techniques (1) and (2) satisfy almost all of these desirable requirements except that they have a quasi-high refractive index, whereas the technique (2) requires the cost of producing and purifying the monomer. The problem is that the resin is expensive and the impact resistance and light resistance of the obtained resin are insufficient, and in the case of, the technology has not been solidified yet and the operating conditions are severe, so the yield has reached a satisfactory point. The problem is not. It improves that the therefore and techniques not obtained only sub-high refractive index, if it was possible to increase the high refractive index (around N _D from 1.57 to 1.60), say to give a most desirable method obtain. The present inventors have conducted extensive research to obtain the most desirable method, and arrived at the present invention.

[Procedure 3]

[Document name to be amended] Statement

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[Correction method] Change

[Correction content]

Now, a method for synthesizing the triphenylvinylsilane used in the present invention will be described. Method for synthesizing triphenylhinylsilane: It can be synthesized using the Grignard reaction. As an example, using sufficiently purified tetrahydrofuran as a solvent, vinylmagnesium bromide is allowed to act on triphenylchlorosilane or triphenylsilane, decomposed with a saturated aqueous solution of ammonium chloride, and then triphenylvinylsilane dissolved in tetrahydrofuran is recovered. Then, it was purified by vacuum distillation in the presence of a polymerization inhibitor and a trace amount of nitrogen gas. It is a white solid (a colorless transparent liquid when melted). (When triphenylsilane is used as the raw material, a small amount (for example, 10% or less) of the raw material substance may remain in the synthesized triphenylvinylsilane, but this has a substantial effect on the performance of the lens resin of the present invention. Is not given.)

[Procedure amendment 4]

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[0027]

Example 1 15 parts by weight of triphenylvinylsilane,
2,2-Bis (methacryloxy-poly <4.3> ethoxy-phenyl) propane [Note: poly <4.3> ethoxy represents a total of 4.3 mol of ethylene oxide polymerized groups. The same applies hereinafter] To a monomer mixture consisting of 70 parts by weight, 5 parts by weight of bis (2-hydroxyethoxy) bisphenol S dimethacrylate and 10 parts by weight of m-divinylbenzene, 2- [2hydroxy-5- ( 1, 1,
3,3-Tetramethylbutyl) phenyl] benzotriazole (0.3 parts by weight) was added and dissolved, and dineopentyl purge carbonate (0.1% by weight) was added as a radical polymerization initiator.
8 parts by weight and 1.2 parts by weight of t-butylperoxy-2-ethylhexanoate were added and dissolved, and this polymerization mixture was mixed with two surface-reinforced glass flat plate molds (spaced 2 m apart.
m) and an ethylene-butadiene copolymer gasket were introduced into the space at room temperature to carry out cast polymerization.

[Procedure Amendment 5]

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[0029]

Example 2 Instead of the monomer mixture used in Example 1,
20 parts by weight of triphenylvinylsilane, 50 parts by weight of 2,2-bis (methacryloxy-poly <4.3> ethoxy-phenyl) propane, 20 parts by weight of bis (2-hydroxyethoxy) bisphenol S dimethacrylate and 10 parts of m-divinylbenzene. 1 part by weight of t-butylperoxy-2-ethylhexanoate was used as the radical polymerization initiator, and a monomer mixture consisting of 1 part by weight was used. The temperature-time curve at the time of mold polymerization shows that the temperature rises from 50 ° C to 85 ° C with a gentle slope over 12 hours, and from 85 ° C to 105 ° C rises rapidly in 3 hours, and at 105 ° C for 2 hours. Polymerization was terminated by continuous heating, and after releasing, heat treatment was performed at 110 ° C. for 1 hour. The other operating method was the same as in Example 1 except that a resin plate was prepared. This product is colorless and transparent, has a high refractive index and low dispersion (ν _D 4
It was 5). The test results are shown in Table 1.

[Procedure correction 6]

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[0030]

Example 3 Instead of the monomer mixture used in Example 2,
Triphenylvinylsilane 25 parts by weight 2,2-bis (acryloxy-poly <4.2> ethoxy-phenyl) propane [Note: poly <4.2> ethoxy represents a total of 4.2 mol of ethylene oxide polymerized groups] 45 A resin plate was prepared under the same conditions as in Example 2, except that a monomer mixture consisting of 10 parts by weight of bisphenol S diacrylate and 20 parts by weight of phenyl methacrylate was used. It was colorless and transparent, had a high refractive index, and had a low dispersion (ν _D 46). The test results are shown in Table 1.

[Procedure Amendment 7]

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[0031]

Example 4 Instead of the monomer mixture used in Example 1,
10 parts by weight of triphenylvinylsilane, 70 parts by weight of 2-bis (methacryloxy-poly <4.3> ethoxy-phenyl) propane, 1 of bisphenol S dimethacrylate
A monomer mixture consisting of 0 parts by weight and 10 parts by weight of m-divinylbenzene was used, and the radical polymerization initiator was 1.2 parts by weight of t-butylperoxy-2-ethylhexanoate and 1,1-bis (t). -Butylperoxy) -3,
1 part by weight of 3,5-trimethylcyclohexane was added, hot injection was performed, and the temperature-time curve of the casting polymerization was 50 ° C. to 80 ° C. The temperature rises rapidly from ℃ to 95 ℃ in 2 hours, rises slowly from 95 ℃ to 110 ℃ in 5 hours, and rises rapidly from 110 ℃ to 120 ℃ in 1.5 hours. The mixture was heated and heated continuously at 120 ° C. for 1.5 hours to terminate the polymerization, and after releasing from the mold, it was heat-treated at 125 ° C. for 1 hour. Other procedures were the same as in Example 1, and a resin plate was prepared and tested. The test results are shown in Table 1.

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[0032]

Example 5 In place of the monomer mixture used in Example 4, 30 parts by weight of triphenylvinylsilane, 2,2-bis (methacryloxy-poly (4.5) ethoxy-phenyl) propane [Note: poly <4 .5> ethoxy represents a total of 4.5 mol of ethylene oxide polymerized groups] 38 parts by weight, bis (2
-Hydroxyethoxy) bisphenol S dimethacrylate 20 parts by weight and a monomer mixture of 12 parts by weight of m-divinylbenzene were used, and a resin plate was prepared and tested under the same conditions as in Example 4. The results are shown in Table 1.

[Procedure Amendment 9]

[Document name to be amended] Statement

[Correction target item name] 0034

[Correction method] Change

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[0034]

As described above, the present invention has a refractive index N _D
Is not only high around 1.57 to 1.60, but also has a high Abbe number ν _D (that is, low dispersion) and many other excellent properties. It is provided. That is, in the present invention, by using triphenylvinylsilane as a monomer for improving the performance that brings about a high refractive index, 2,2-bis (acryloxy-polyethoxy-
Phenyl) propane and / or 2,2-bis (methacrylyloxy-polyethoxy-phenyl) propane are allowed to coexist as a main monomer, and a known third monomer is appropriately added thereto to make it suitable for factory operation. It is intended to provide a method for producing a good resin for a high refractive index lens.

[Procedure Amendment 10]

[Document name to be amended] Statement

[Correction target item name] 0033

[Correction method] Change

[Correction content]

[0033]

[Table 1]

Claims (2)

[Claims] 1. A resin for high-refractive-index lenses, characterized by copolymerizing triphenylvinylsilane and one or more radical-polymerizable monomers having a homopolymer refractive index of 1.55 or more. Manufacturing method. 2. Triphenylvinylsilane is used as the first monomer in an amount of 3 to 40% by weight, preferably 7 to 30% by weight, and the second monomer is represented by the following chemical formula 1. (However, R represents hydrogen or a methyl group, and m ≧ 1, n ≧
1 to 20 and 70% by weight of one or a mixture of two or more compounds represented by the formula (1) and m + n represents a number of more than 4 and 6 or less, and a homopolymer having a refractive index of 1 is used as the third monomer. 0.55 or more of one or more other radically polymerizable monomers are mixed in an amount of 0 to 40% by weight and copolymerized, and a method for producing a resin for a high refractive index lens.