JP3324854B2 - Polymerizable composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a polymerizable composition suitable as a raw material for producing a transparent resin, particularly a lens for eyeglasses. More specifically, it has low water absorption, excellent dyeing properties, and is not colored and has sufficient physical properties as an eyeglass lens, for example, dispersing properties, hardness, light resistance, heat resistance, and odorlessness during resin processing. An object of the present invention is to provide a polymerizable composition suitable for producing a transparent resin.

[0002]

2. Description of the Related Art Conventionally, various studies have been made on organic glasses in place of inorganic glasses, but there are many drawbacks, and no satisfactory properties have yet been obtained. For example, a polymer obtained by polymerizing a monomer containing methyl methacrylate or diethylene glycol bis (allyl carbonate) as a main component is used as an optical material or a lens, but has a low refractive index of about 1.50.

[0003] Various high-refractive-index resins have been proposed which have alleviated this disadvantage. For example, polycarbonate and polysulfone-based high refractive index resins have been proposed. Although these resins have a high refractive index of about 1.60, they have problems such as low light transmittance, optical homogeneity, and coloring.

For this reason, various cross-linkable high refractive index resins have been proposed. For example, JP-A-4-227617 proposes a resin containing dimethacrylate of a bisphenol compound and polyoxyalkylene glycol dimethacrylate. However, since this resin contains polyoxyalkylene glycol dimethacrylate, it has a high water absorption, and the lens tends to be misaligned, and the coating film is liable to crack when an antireflection coating of an inorganic compound is applied to the lens substrate surface. Also, Japanese Patent Application Laid-Open No. 55-13747 proposes a composition for a high refractive index resin comprising bisphenol compounds such as dimethacrylate and phenyl methacrylate. However, these resins have poor impact resistance.

In WO 92/05209, impact resistance is improved by adding an alkyl acrylate or methacrylate such as butyl acrylate or methacrylate to a polymerizable composition having dimethacrylate of a bisphenol compound. The disadvantage is that the lens is colored yellow.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide a polymer having low water absorption, excellent dyeing properties, excellent impact resistance, no coloring, and excellent physical properties as a lens for eyeglasses. To provide a polymerizable composition that gives

[0007]

The present inventors have made intensive studies to achieve the above object, and as a result, (A) a diacrylate compound or a dimethacrylate compound having a specific structure is added to (B) an alkyl acrylate or an alkyl acrylate. The inventors have found that the above object can be achieved by a polymerizable composition containing methacrylate and (C) a specific urethane acrylate compound or a urethane methacrylate compound, and have completed the present invention.

That is, the present invention relates to (A) the general formula (1)

[0009]

Embedded image

(Where R ¹ and R ² are a hydrogen atom or a methyl group, m and n are each an integer of 0 to 2, X is a halogen atom excluding fluorine, and a is an integer of 0 to 4) 100 parts by weight of a diacrylate compound or a dimethacrylate compound represented by the following formula: (B) 5 to 200 parts by weight of an alkyl acrylate or alkyl methacrylate and (C) a general formula (2)

[0011]

Embedded image

Wherein R ³ is a hydrogen atom or a methyl group, R ⁴ is an alkylene group which may be substituted with an acryloyloxymethyl group or a methacryloyloxymethyl group, and s is an integer of 2 to 4. And A is an s-valent organic group. Urethane acrylate compounds or mega comprising urethane methacrylate compounds 1 to 30 parts by weight indicated by]
It is a polymerizable composition for nelens .

In the following description, acrylate compounds and methacrylate compounds are collectively referred to as (meth) acrylate compounds.

In the general formula (1), m and n are each independently an integer of 0 to 2, and a is an integer of 0 to 4. m and n are preferably 0 or 1 in consideration of the refractive index of the resin obtained by polymerizing the polymerizable composition of the present invention, and a is preferably 0 to 2. X is a halogen atom excluding fluorine. As a halogen atom, chlorine,
Although each atom of bromine and iodine is employed, a chlorine atom or a bromine atom is particularly preferable from the viewpoint of light resistance.

The di (meth) acrylate compound represented by the general formula (1) used in the present invention is as follows. 2,2-bis (4-methacryloyloxyphenyl) propane, 2,2-bis (4-methacryloyloxy-3-chlorophenyl) propane, 2,2-bis (4-methacryloyloxy-3,5-dichlorophenyl) propane, 2,2-bis (4-methacryloyloxy-3-bromophenyl) propane, 2,2-bis (4-methacryloyloxy-3,5-dibromophenyl) propane, 2,2-bis (4-methacryloyloxyethoxyphenyl) ) Propane, 2,2-bis (4-methacryloyloxyethoxy-3-chlorophenyl) propane, 2,2-bis (4-methacryloyloxyethoxy-3,5-dichlorophenyl) propane, 2,2-
Bis (4-methacryloyloxyethoxy-3-bromophenyl) propane, 2,2-bis (4-methacryloyloxyethoxy-3,5-dibromophenyl) propane, 2,2-bis (4-methacryloyloxyethoxyethoxyphenyl) Propane, 2,2-bis (4-methacryloyloxyethoxyethoxy-3-chlorophenyl) propane, 2,2-bis (4-methacryloyloxyethoxyethoxy-3,5-dichlorophenyl) propane, 2,2-bis (4- Methacryloyloxyethoxyethoxy-3-bromophenyl) propane, 2,2-
Bis (4-methacryloyloxyethoxyethoxy-
3,5-dibromophenyl) propane and the like. These di (meth) acrylate compounds can be used alone or in combination of two or more.

Next, the alkyl (meth) acrylate used as the component (B) of the polymerizable composition of the present invention is an esterification reaction product of a corresponding alcohol and acrylic acid or methacrylic acid. The compounds can be used without any restrictions. Examples of the alkyl (meth) acrylate compound suitably used in the present invention are as follows. The following general formula (3)

[0017]

Embedded image

(Wherein, R ⁵ is a hydrogen atom or a methyl group, and R ⁶ is an alkyl group).

The alkyl group represented by R ⁶ in the general formula (3) is not limited at all, such as linear, branched or cyclic, and is not particularly limited in the number of carbon atoms. Considering the impact resistance and heat resistance of the obtained resin, R ⁶
Is preferably an alkyl group having 3 to 15 carbon atoms. Specific examples of the alkyl (meth) acrylate suitably used in the present invention include methyl (meth) acrylate, ethyl (meth) acrylate, n-
Propyl (meth) acrylate, n-butyl (meth) acrylate, iso-butyl (meth) acrylate, i
Examples thereof include so-amyl (meth) acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, lauryl (meth) acrylate, and isobornyl (meth) acrylate. These alkyl (meth) acrylates can be used alone or in combination of two or more.

As the urethane (meth) acrylate compound as the component (C) of the polymerizable composition of the present invention, known compounds can be used without any limitation as long as they are represented by the general formula (2). In the present invention, a compound having 2 to 6 acryloyl groups or methacryloyl groups in one molecule is particularly preferable.

In the general formula (2), R ⁴ is an alkylene group which may be substituted with an acryloyloxymethyl group or a methacryloyloxymethyl group. The number of carbon atoms of the alkylene group is not particularly limited, but is generally preferably an alkylene group having 1 to 4 carbon atoms such as a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a propylene group, and a butylene group.

A in the general formula may be any organic group, and in the present invention, the following organic groups are particularly preferable. following formula when ^{s = 2 - (R 7 NHCOOR} 8 CONH) v R 9 - ; and when the s = 3 to 4, the following formula ^{{- (R 7 NHCOOR 8)} v} w R 10 { However, R ⁷ , R ⁸ and R ⁹ are the same or different alkylene groups, respectively,

[0023]

Embedded image

(Where R ¹¹ and R ¹² are the same or different alkylene groups or arylene groups, respectively)
x and y are each 0 or 1, and z is 1 to 1.
It is an integer of 0. ), A group represented by the following formula

[0025]

Embedded image

Or

[0027]

Embedded image

(Where R ¹³ is a hydrogen atom, a halogen atom or an alkyl group, R ¹⁴ is a hydrogen atom or a methyl group, t is an integer of 0 to 8, and p and q are each independently 0 or R ¹⁰ is a trivalent to tetravalent hydrocarbon residue, and v is 0 to 2.
An integer of 10 and w is the number of groups bonded to R ¹⁰ and is an integer of 3 to 4. ｝. ] Is an organic group represented by the formula: In the above formula, the carbon number of the alkyl group and the alkylene group is preferably in the range of 1 to 6, and the alkylene group is more preferably an ethylene group or a propylene group. Further, the number of carbon atoms of the arylene group is preferably in the range of 6 to 10, and a phenylene group is particularly preferable. Further, as the hydrocarbon residue, a trivalent to tetravalent group derived from an alkane having 2 to 6 carbon atoms is preferable.

The urethane (meth) acrylate compound used in the present invention is produced by a known method by reacting a polyfunctional isocyanate compound, a compound having a hydroxyl group and a polymerizable double bond, and / or a polyol compound. Is done. Examples of the polyfunctional isocyanate compound include ethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, tolylene diisocyanate, and polyisocyanate prepolymer. Examples of the compound having a hydroxyl group and a polymerizable double bond include 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl (meth) acrylate, and glycerin diacrylate. Examples of the polyol compound include polyethylene glycol, polypropylene glycol, bisphenol A, an ethylene oxide adduct of bisphenol A, polyester, polyurethane polyol, pentaerythritol, 2,2-bis (hydroxymethyl) butanol, and the like.

In the present invention, the above (A) and (B)
The amount of the component (B) is 5 to 200 parts by weight per 100 parts by weight of the component (A).
Component should be in the range of 1 to 30 parts by weight, more preferably 100 parts by weight of component (A) and 1 part by weight of component (B).
It is preferable that 0 to 150 parts by weight and the component (C) be in the range of 4 to 25 parts by weight. When a composition comprising only two components excluding the component (C), that is, a composition comprising only the two components (A) and (B), is polymerized, the resulting polymer is colored yellow and can no longer be used for lens applications. . In addition, the viscosity of the composition is significantly increased only by the components (A) and (C),
In effect, casting polymerization becomes difficult. Furthermore, a sufficient refractive index cannot be obtained with only the components (B) and (C).

When the amounts of the components (B) and (C) do not fall within the above ranges with respect to 100 parts by weight of the component (A), the physical properties of the obtained polymer, that is,
It is not preferable because heat resistance, dyeability, light resistance and the like are reduced. Specifically, when the amount of the component (B) is 5 parts by weight or less with respect to 100 parts by weight of the component (A), the viscosity of the composition is significantly increased, and the operability is poor. The refractive index decreases. When the amount of the component (C) is 1 part by weight or less with respect to 100 parts by weight of the component (A), the lens is colored or heat-resistant yellowing occurs. I do.

In the present invention, when polymerizing the polymerizable composition, the polymerizable composition is often adjusted for ease of polymerization, adjustment of the viscosity of the polymerizable composition, adjustment of the refractive index, or adjustment of other physical properties. It is also possible to carry out copolymerization by mixing the hydrophilic composition and other radical copolymerizable monomers. Examples of these other monomers include unsaturated carboxylic acids such as methacrylic acid, maleic anhydride and fumaric acid; and suitable functional groups such as 2-hydroxyethyl (meth) acrylate and glycidyl (meth) acrylate ( (Meth) acrylate compounds; alkylene glycol (meth) acrylate compounds such as methoxypolyethylene glycol (meth) acrylate, methoxypolypropylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, and polypropylene glycol di (meth) acrylate; methylthio Thio (meth) acrylate compounds such as (meth) acrylate and benzylthio (meth) acrylate; monomethyl fumarate;
Fumaric ester compounds such as diethyl fumarate and diphenyl fumarate; styrene or α-methylstyrene derivatives such as styrene, divinylbenzene, α-methylstyrene, α-methylstyrene dimer and bis- (vinylbenzyl) ether; diallyl phthalate; Allyl compounds such as diallyl terephthalate, diallyl isophthalate, diallyl tartrate, diallyl epoxysuccinate, diallyl maleate, allyl cinnamate, diallyl carbonate, and allyl diglycol carbonate; and epoxy (meth) acrylate. These other monomers can be used alone or in combination of two or more.

The amount of these other monomers may be selected according to the purpose, but is preferably in the range of 0 to 200 parts by weight per 100 parts by weight of component (A).

In particular, in the present invention, considering the physical properties such as the refractive index, hard coat property, heat-resistant yellowing property and dyeing property of the obtained polymer, the polymer (A) has a phenyl group with respect to 100 parts by weight of the component (A). It is preferable to use a meth) acrylate, a (meth) acrylate having a hydroxyl group, glycidyl methacrylate, an epoxy acrylate, an alkylene glycol (meth) acrylate or the like in an amount of 1 to 50 parts by weight. Examples of the (meth) acrylate having a hydroxyl group include 2-hydroxyethyl acrylate,
Examples thereof include 2-hydroxyethyl methacrylate, 1,2-dihydroxyethyl methacrylate, and 2-hydroxypropyl methacrylate. Examples of the alkylene glycol (meth) acrylate include methoxy (tetraethylene glycol) (meth) acrylate and methoxy (nonaethylene glycol) (meth).
Examples include acrylate, tetraethylene glycol di (meth) acrylate, and nonaethylene glycol di (meth) acrylate.

The polymerizable composition of the present invention can be polymerized by a known casting polymerization method. The polymerization initiation method is
It can be carried out by thermal polymerization using a radical polymerization initiator such as various peroxides and azo compounds. To illustrate a typical polymerization method, it is possible to exemplify a cast polymerization in which the polymerizable composition of the present invention is injected between molds held by an elastomer gasket or a spacer, cured in an air furnace, and then removed. it can.

The radical polymerization initiator is not particularly limited and known ones can be used. Typical examples thereof include benzoyl peroxide, p-chlorobenzoyl peroxide, decanoyl peroxide, lauroyl peroxide, and the like. Diacyl peroxide such as acetyl peroxide; tert-butylperoxy-2
-Ethylhexanoate, tert-butylperoxydicarbonate, cumylperoxyneodecanate, t
tert-butyl peroxyneodecane, tert-
Peroxyesters such as butyl peroxybenzoate; diisopropyl peroxydicarbonate, di-2
-Ethylhexyl peroxydicarbonate, di-se
Percarbonates such as c-butyl peroxydicarbonate; and azo compounds such as azobisisobutyronitrile.

The amount of the radical polymerization initiator used depends on the polymerization conditions, the type of the initiator and the type and composition of the above-mentioned monomers, and cannot be limited unconditionally.
It is preferable to use 0.01 to 10 parts by weight based on parts by weight.

Among the polymerization conditions, particularly the temperature affects the properties of the obtained resin. This temperature condition is affected by the type and amount of the radical polymerization initiator and the type of the monomer, and thus cannot be limited unconditionally. Generally, the polymerization is started at a relatively low temperature and the temperature is gradually increased. It is preferable to perform a so-called taper type two-stage polymerization in which the polymerization is completed and the mixture is cured at a high temperature at the end of the polymerization.

Since the polymerization time also depends on various factors like the temperature, it is preferable to determine an optimum time in advance in accordance with these conditions. However, in general, the conditions are set so that the polymerization is completed in 2 to 40 hours. It is preferred to choose

The polymerizable composition of the present invention can be similarly cast-polymerized by known photopolymerization using ultraviolet light or visible light, in addition to the above-described cast polymerization method using thermal polymerization. In this case, benzoin, benzoin methyl ether, benzoin isobutyl ether, benzophenol, acetophenone,
4'-dichlorobenzophenone, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzylmethylketal, 1- (4-
Isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-isopropylthioxanthone, 2,
4,6-trimethylbenzoyldiphenylphosphine oxide and the like. These photopolymerization initiators,
In order to prevent coloring and deterioration of the obtained polymer, it is generally used in the range of 0.001 to 5 parts by weight based on 100 parts by weight of all monomers.

Further, the light source used in the photopolymerization is as follows:
Those that emit ultraviolet light are preferable, for example, a mercury lamp,
A germicidal lamp, a xenon lamp or the like can be suitably used. In addition, visible light such as sunlight can be used. The irradiation time varies depending on the wavelength and intensity of the light source, the shape and the material of the polymer, and may be determined in advance by preliminary experiments or the like.

When performing photopolymerization, it is necessary that at least the surface of the mold to be irradiated with light is transparent, and glass or the like is generally used for this portion. In particular, a material that easily transmits ultraviolet light, such as quartz glass, is preferable, but the material is not particularly limited as long as it is transparent. In addition, polymerization may be performed while applying pressure from outside during molding.

In the photopolymerization, a polymerization accelerator, a polymerization regulator, a release agent, an ultraviolet absorber, an antioxidant, a coloring inhibitor,
Various additives such as an antistatic agent, a fluorescent dye, a dye, a pigment, and a fragrance can be selected and used as needed.

The polymer obtained by the above-mentioned method can be coated with a known coating agent in order to improve the scratch resistance of the surface depending on the intended use, whereby a cured film can be formed. At this time, the coating agent that forms the cured film reacts with heat, a catalyst, a curing agent, light, radiation, and the like, and forms a three-dimensional network structure to form a cured film,
So-called crosslinkable substances can be used without limitation. For example, melamine-based coating agents composed of melamines and other reactive substances such as formaldehyde, acrylic-based coating agents composed of acrylates and amides, and epoxy and other reactive substances such as bisphenol A Epoxy-based coating agent composed of other reactive substances such as polyfunctional isocyanates and polyfunctional alcohols, a silicon-based coating agent composed of organosilicon compounds such as methyltrimethoxysilane, etc., Alternatively, a known coating agent that combines these is used.

An example of a coating agent suitably used in the present invention is as follows. The following general formula (4)

[0046]

Embedded image

[0047] (wherein, A ¹ is a straight-chain with at least 4 or more consisting of atoms a divalent functional group, R ^{1 5} and R ^16,
They are the same or different alkyl groups or alkoxyalkyl groups, respectively, and R ¹⁷ and R ¹⁸ are the same or different alkyl groups or alkoxy groups, respectively. And a coating agent containing a disilane compound as a component.

In order to further increase the adhesion between the polymer and the cured film, it is often a preferred embodiment to carry out a pretreatment of the polymer before coating. For example, a known alkali treatment can be used for the pretreatment method, and the stronger the alkalinity, the stronger the adhesion. However, if the alkalinity is too strong, the polymer itself may be deteriorated.
It is preferable that the alkaline treatment condition is milder than the treatment condition of the NaOH aqueous solution at 80 ° C. for 1 hour.

The polymer obtained by curing the polymerizable composition may be coated with an inorganic hard material as an antireflection agent, if necessary. Known methods can be used for coating the inorganic hard material without any particular limitation. For example, a dry plating method such as a vacuum evaporation method, an ion plating method, and a sputtering method can be suitably used.
The thickness of the inorganic hard film is not particularly limited because it varies depending on the purpose, but generally 0.1 to 10 μm is preferable.

As the inorganic hard material, an inorganic compound or metal capable of forming a film on the surface of a polymer by the dry plating method as described above can be used without any limitation, and if it is appropriately selected according to the purpose, Good.
For example, to provide abrasion resistance, silicon oxide (Si
Ox, x = 1 to 2), aluminum oxide and the like are generally used. In order to impart anti-reflection properties, for example,
Metal oxides such as silicon oxide, aluminum oxide, zirconium oxide, titanium oxide, magnesium oxide, cerium oxide, indium oxide, tantalum oxide, and hafnium oxide; metals such as magnesium fluoride, cerium fluoride, lithium fluoride, and neodymium fluoride Fluoride; metal sulfide such as zinc sulfide; and metals such as aluminum, gold, silver, and chromium. Among such inorganic hard materials, a low refractive index material can be coated with a single layer, and a low refractive index material and a high refractive index material can be alternately laminated to an optical thickness. Further, in order to simultaneously provide the reflectivity and the scratch resistance, the amorphous carbon may be coated with diamond-like carbon in which diamond microcrystals are dispersed.

[0051]

The polymer obtained by polymerizing the polymerizable composition of the present invention has a high refractive index, is non-colored, has low water absorption, is excellent in dyeability and impact resistance, and is a lens for glasses. It has excellent physical properties such as dispersion characteristics, hardness, transparency, light resistance, heat resistance, and odorlessness during cutting.

Therefore, the polymer obtained by polymerizing the polymerizable composition of the present invention is useful as an organic glass, and is most suitable as an optical lens such as an eyeglass lens, an optical instrument lens, etc. And optical fibers.

[0053]

EXAMPLES Hereinafter, the present invention will be described specifically with reference to examples, but the present invention is not limited to these examples. Various properties of the resin obtained in the examples were measured by the following test methods.

(1) Refractive index and Abbe number The refractive index at 20 ° C. was measured using an Abbe refractometer manufactured by Atago Co., Ltd. Bromonaphthalene or methylene iodide was used as the contact solution.

(2) Hardness Using a Rockwell hardness tester, the value of the test piece having a thickness of 2 mm was measured on an L-scale.

(3) Yellowness (YI) YI of the sample was measured with a color difference meter (SM-4) manufactured by Suga Test Instruments Co., Ltd.
Was measured.

(4) Specific gravity An electronic hydrometer (ED-120T) manufactured by Mirage Trading Co., Ltd.
(Type).

(5) Dyeability 2 g of a disperse dye (trade name: Vista Brown, manufactured by Hattori Seiko Co., Ltd.) was dispersed in 1 liter of water, heated, and the sample was dyed at 90 ° C. for 10 minutes. The dyeing density at that time was expressed as a reduction rate (percentage) of the light transmittance at 550 nm using a double beam spectrophotometer 220A manufactured by Hitachi, Ltd.

(6) Light fastness A sample was placed in a long life xenon fade meter (FAC-25AX-HC type) manufactured by Suga Test Instruments Co., Ltd., and after exposing for 100 hours to xenon light, Suga Test Instruments Co., Ltd. The YI of the sample was measured with a colorimeter (SM-4 type) and expressed as an increase ΔYI with respect to the initial YI.

(7) Impact resistance 16 g, 32 g, 48 g, 64 g, 80 g, 96 g of a test plate having a thickness of 2 mm and a diameter of 65 mm from a height of 127 cm.
g, 112 g, and 131 g of steel balls were allowed to fall naturally, and the evaluation was made based on the weight of the heaviest steel ball that did not damage the test plate.

(8) Hard Coatability A silicone-based hard coat agent (trade name: TS-56T, manufactured by Tokuyama Soda Co., Ltd.) was used, and a hard coat agent for one week and one month was applied after preparation. One month after the preparation, the hard coat agent having good adhesion was evaluated as ◎, one week after the preparation was evaluated as good, and the poor one was evaluated as x.

(9) Heat-resistant yellowing After heating a sample having a thickness of 2 mm at 130 ° C. for 2 hours, the YI of the sample was measured with a color difference meter (SM-4 type, manufactured by Suga Test Instruments Co., Ltd.).増 加 YI.

(10) Water Absorption A sample piece dried at 120 ° C. for 1 hour was allowed to stand in water at 25 ° C. for 3 days, and then the weight increase rate (percentage) was measured.

The compounds used in the following Examples and Comparative Examples are as follows.

Component (A): di (meth) acrylate compound BPM: 2,2-bis (4-methacryloyloxyphenyl) propane

[0066]

Embedded image

BPEM: 2,2-bis (4-methacryloyloxyethoxyphenyl) propane

[0068]

Embedded image

TBEM: 2,2-bis (4-methacryloyloxyethoxy-3,5-dibromophenyl) propane

[0070]

Embedded image

Component (B): alkyl methacrylate BuMA: normal-butyl methacrylate i-BuMA: iso-butyl methacrylate MMA: methyl methacrylate CHMA: cyclohexyl methacrylate IBMA: isobornyl methacrylate Component (C): urethane (meth) acrylate compound UA -HTP1: urethane methacrylate of the following formula

[0072]

Embedded image

UA-HTP2: urethane acrylate of the following formula

[0074]

Embedded image

UA-GXE: urethane methacrylate of the following formula

[0076]

Embedded image

UA-HTP3: urethane methacrylate of the following formula

[0078]

Embedded image

UA-HTP4: urethane acrylate of the following formula

[0080]

Embedded image

Component (D): Other monomers HEMA: 2-hydroxyethyl methacrylate GMA: glycidyl methacrylate PhMA: phenyl methacrylate BzMA: benzyl methacrylate 40G: methoxypolyethylene glycol # 230 methacrylate 90G: methoxypolyethylene glycol # 400 methacrylate 1 t-butyl peroxy neodecaneate as a radical polymerization initiator with respect to 100 parts by weight of a polymerizable composition containing the components (A), (B), (C) and (D) shown in Table 1 One part by weight was added and mixed well. This mixture was poured into a mold composed of a glass plate and a gasket composed of an ethylene-vinyl acetate copolymer, and cast polymerization was performed. In the polymerization, the temperature was gradually raised from 30 ° C. to 90 ° C. over 15 hours using an air furnace, and the temperature was maintained at 90 ° C. for 2 hours. After the completion of the polymerization, the mold was taken out of the air furnace, and after standing to cool, the polymer was removed from the glass of the mold. Table 1 shows the physical properties of the obtained polymer.

Comparative Example The same operation as in Example 1 was carried out except that the components shown in Table 1 were used. Table 1 shows the physical properties of the obtained polymer.

[0083]

[Table 1]

[0084]

[Table 2]

[0085]

[Table 3]

Example 2 100 parts by weight of the polymerizable composition containing the components (A), (B), (C) and (D) shown in Table 2 was mixed with 1-hydroxy as a photopolymerization initiator. 0.1 part by weight of cyclohexylphenyl ketone and 0.1 part by weight of 2,4,6-trimethylbenzoyldiphenylphosphine oxide were added and mixed well. This mixed solution is mixed with a glass plate and ethylene-
The mixture was poured into a mold composed of a gasket made of a vinyl acetate copolymer, and irradiated with ultraviolet rays for 15 seconds using a metal halide lamp having an output of 120 W / cm. After the polymerization was completed, the polymer was removed from the glass of the mold. Table 2 shows the physical properties of the obtained polymer.

[0087]

[Table 4]

[0088]

[Table 5]

[0089]

[Table 6]

──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. ⁷ , DB name) G02B 1/04 C08F 20/00-20/70 C08F 220/00-220/70 C08F 290/00-290 / 14 C08F 299/00-299/08

Claims (2)

(57) [Claims] (A) General formula (1) (Where R ¹ and R ² are a hydrogen atom or a methyl group, m and n are each an integer of 0 to 2, X is a halogen atom excluding fluorine, and a is an integer of 0 to 4. ) : 100 parts by weight , (B) an alkyl acrylate or an alkyl methacrylate : 5 to 200 parts by weight , (C) a general formula (2) Wherein R ³ is a hydrogen atom or a methyl group;
⁴ is an alkylene group which may be substituted with an acryloyloxymethyl group or a methacryloyloxymethyl group, s is an integer of 2 to 4, and A is an s-valent organic group. ] Urethane acrylate represented by compound or urethane methacrylate compound: spectacle lens polymerizable composition comprising 1 to 30 parts by weight. 2. An eyeglass lens comprising a polymer of the polymerizable composition according to claim 1.