JPH10104401A - Synthetic resin lens material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To decrease the specific gravity of a lens material and to improve transparency and refractive index by constituting the material of a copolymer obtd. by polymerizing a monomer compsn. which contains mixture monomers of specified three components. SOLUTION: A monomer compsn. containing mixture monomers of three components (A), (B), (C) is polymerized to obtain a copolymer having <=1.02 specific gravity. These components are (A) 30 to 90wt.% of an ester compd. of an alcohol components containing specified polyhydric alcohols and an acid component of acryl acid or methacryl acid, (B) 0.5 to 20wt.% or specified radical polymerizable urethane compd. and (C) 9.5 to 65wt.% of monomers which can copolymerize with the components (A) and (B). The obtd. copolymer is used to constitute a synthetic resin lens material. It is preferable to use a α- methylstyrene dimer as a mol.wt. controlling agent because the dimer give little influences on the transparency and tone of the obtd. copolymer.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a synthetic resin lens material, and more particularly, to a material having low specific gravity, excellent optical and mechanical properties, and high adhesion to a hard coat layer and a primer layer. The present invention relates to a synthetic resin lens material capable of forming an optical lens.

[0002]

2. Description of the Related Art Conventionally, various inorganic glass materials have been used as materials for optical lenses, but in recent years, synthetic resin materials have become lighter, more workable, more stable, more dyeable, more mass-produced, and less expensive. It has begun to be widely used together with inorganic glass materials because it has a possibility of reducing the amount of slag.

[0003] Among various physical properties required for an optical lens material, it is extremely important that the specific gravity is small. In other words, if an optical lens made of a material having a low specific gravity can be obtained, it is used to reduce the weight of a lens system that occupies an important position in an optical device such as a microscope, a camera, a telescope, and an eyeglass lens. It becomes possible.

For this reason, there is a tendency to further reduce the specific gravity of the synthetic resin lens material and emphasize its superiority over the inorganic glass lens material. For example, a diethylene glycol bisallyl carbonate resin referred to as “CR-39” is currently the most widely used synthetic resin lens material for spectacles. The specific gravity of this resin is 1.3
1 (a value at a temperature of 20 ° C .; the same applies hereinafter), which is relatively large. Also recently,
As a high-refractive-index lens material, a synthetic resin lens material containing a halogen atom or a sulfur atom is known, and the specific gravity of such a synthetic resin lens material is relatively large, about 1.3 to 1.4. . Furthermore, as a synthetic resin lens material having a relatively small specific gravity, polystyrene (specific gravity: 1.0
2) Thermoplastic resins such as polymethyl methacrylate (specific gravity: 1.20) and polycarbonate (specific gravity: 1.19) are known, but these have sufficient optical characteristics required for practical use. Not something.

On the other hand, as a synthetic resin lens material having excellent properties such as heat resistance, solvent resistance and mechanical strength, a copolymer having a crosslinked structure is introduced. For example, a synthetic resin having a triazine ring structure is used. "Nikon Light Deluxe II" and the like have been put into practical use as lens materials. Although the specific gravity of this synthetic resin lens material is 1.17, which is relatively small, it cannot be said that sufficient weight reduction has yet been achieved.

Recently, as a synthetic resin lens material having a low specific gravity and excellent in various properties such as heat resistance, solvent resistance and mechanical strength, a material made of a specific acrylic cross-linked copolymer has been used. It has been proposed (Japanese Patent Laid-Open No. 7-29)
No. 2043). However, this synthetic resin lens material has the following problems. In general,
In an optical lens, a hard coat layer or a primer layer made of, for example, a silicone material is formed on the surface thereof. However, in the above-mentioned lens material, adhesion to the hard coat layer and the primer layer is not yet sufficient, and improvement thereof is strongly desired.

[0007]

DISCLOSURE OF THE INVENTION The present invention has been made based on the above circumstances, and its object is to provide:
It is an object of the present invention to provide a synthetic resin lens material having a low specific gravity, having excellent optical and mechanical properties, and capable of forming an optical lens having high adhesion to a hard coat layer and a primer layer.

[0008]

The synthetic resin lens material of the present invention comprises 30 to 90% by mass of the following component (A), 0.5 to 20% by mass of the following component (B), and 9 to 9% of the following [C] component. .
It is characterized by comprising a copolymer having a specific gravity of 1.02 or less, obtained by polymerizing a monomer composition containing a mixed monomer of 5 to 65% by mass.

Further, the synthetic resin lens material of the present invention comprises 30 to 90% by mass of the following component [A] and the following component [D].
5 to 20% by mass and the following component [C] 9.5 to 65% by mass
And a copolymer having a specific gravity of 1.02 or less, obtained by polymerizing a monomer composition containing a mixed monomer consisting of

[0010] component [A]: following A ¹ component and the following A ²
At least one polyhydric alcohol 60 selected from the components
100 wt%, and at least one compound selected from the following A ³ component and below A ⁴ component 40 to 0 wt%
Obtained from an alcohol component consisting of: and an acid component consisting of acrylic acid or methacrylic acid. [A ¹ component]: dimer diol obtained by carbon atoms to reduction treatment dimers of higher unsaturated fatty acids is 11 to 22, and reduction treatment dimer of a lower alcohol esters of the higher unsaturated fatty acid At least one diol selected from dimer diols obtained by the above method. [A ² component]: reduction treatment trimer of a lower alcohol ester of carbon number trimer triol obtained by reduction treatment trimer of higher unsaturated fatty acids is 11 to 22, and the higher unsaturated fatty acid At least one triol selected from trimer triols obtained by the above method. [A ³ Component]: A ¹ component and at least one polyhydric intermolecular ether compound obtained by a dehydration reaction of an alcohol selected from A ² component. [A ⁴ Component]: A ¹ component and A ² and a polyhydric alcohol of at least one selected from the components, the polyhydric hydroxyl group-containing ester compound obtained by reacting the corresponding carboxylic acid to alcohol.

[0011] [B] component: following B ¹ component and the radical polymerizable urethane compound obtained by reacting the following B ² component and below B ³ component. [B ¹ component]: a polyisocyanate compound. [B ² Component]: at least one hydroxyl group and at least one radical polymerizable unsaturated bond compound having in the molecule. [B ³ Component]: fatty alcohols having 6 or more monovalent carbon.

Component [C]: A monomer copolymerizable with the components [A] and [B].

Component (D): at least one unsaturated isocyanate compound selected from the compound represented by the following structural formula (I) and the compound represented by the following structural formula (II).

[0014]

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In the synthetic resin lens material of the present invention,
The mixed monomer preferably contains at least one selected from the group consisting of t-butyl (meth) acrylate, styrene and t-butylstyrene as component [C], and divinylbenzene. It is preferable that the monomer mixture contains 3 to 25% by mass of divinylbenzene as all or a part of the component [C].

Further, in the synthetic resin lens material of the present invention, the monomer composition contains the α-methylstyrene dimer at a ratio of 0.1 to 5% by mass of the mixed monomer. It is preferably contained.

[0017]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the synthetic resin lens material of the present invention will be described in detail. In one embodiment of the present invention, (1) a component (A) consisting of an esterified product of an alcohol component containing a specific polyhydric alcohol and an acid component consisting of acrylic acid or methacrylic acid;
A component (B) composed of a specific radically polymerizable urethane compound, and a mixed monomer composed of (3) a component (C) composed of a monomer copolymerizable with the component (A) and the component (B). The synthetic resin lens material is constituted by a copolymer obtained by polymerizing a monomer composition containing a polymer.

In another embodiment of the present invention,
(1) The component (A), (2) a component (D) comprising a specific unsaturated isocyanate compound, and (3) a simple monomer containing a mixed monomer comprising the three components of the component (C). The synthetic resin lens material is composed of a copolymer obtained by polymerizing the monomer composition.

The particular polyhydric alcohol used as the alcohol component for obtaining the <component [A]> [A] component is at least selected from A ¹ component and consisting of a specific triol A ² component consisting specific diol One type of polyhydric alcohol.

The specific diol which is the component A ¹ is (a)
Dimers of unsaturated fatty acids having 11 to 22 carbon atoms (hereinafter also referred to as “dimer acids”), or (b) 11 to 11 carbon atoms
It is a dimer diol obtained by subjecting a component (A1-1) consisting of a dimer of a lower alcohol ester of an unsaturated fatty acid of ^No. 22 (hereinafter, also referred to as "dimer acid ester") to reduction treatment by hydrogenation.

Further, certain triol is A ² component, (i) trimers of unsaturated fatty acids of 11-22 carbon atoms (hereinafter, also referred to as "trimer acids".), Or, (b)
Trimer of a lower alcohol esters of unsaturated fatty acids of 11-22 carbon atoms (hereinafter, also referred to as "trimer acid ester".) Trimer obtained by reduction by hydrogenation of from consisting (A ² -1) component Trial.

[0022] (A ¹ -1) component and (A ² -1) The raw material is a higher unsaturated fatty acid components, 1-4 unsaturated bonds (double bonds), preferably 1 to 2 containing And
Those having 11 to 22, preferably 14 to 20, and more preferably 16 to 18 carbon atoms are used. When the carbon number of the higher unsaturated fatty acid is less than 11, it is difficult to obtain a lens material having a low specific gravity. On the other hand, when the number of carbon atoms exceeds 22, it becomes difficult to obtain a lens material having excellent mechanical performance due to a decrease in crosslink density and the like. Specific examples of such higher unsaturated fatty acids include oleic acid, elaidic acid, octadecenoic acid, linoleic acid, valmitoleic acid, myristoleic acid, linolenic acid, isooleic acid, eicosenoic acid, docosenoic acid, branched octadecenoic acid,
Examples include branched hexadecenoic acid and undecylenic acid. These higher unsaturated fatty acids can be used alone or in combination of two or more.

The lower alcohol esters of higher unsaturated fatty acids (hereinafter, also simply referred to as "higher unsaturated fatty acid esters") include the above-mentioned higher unsaturated fatty acids and those having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms. Esters with lower aliphatic alcohols can be mentioned, for example, methyl ester, ethyl ester, propyl ester, butyl ester and the like. These higher unsaturated fatty acid esters may be used alone or in combination of two or more.

[0024] by reacting a raw material composed of such a higher unsaturated fatty acid or higher unsaturated fatty acid esters, these dimers (A ¹ -1) is a component or trimer (A ² -1 ) Component is obtained.

[0025] As the reaction catalyst in order to obtain a (A ¹ -1) component or (A ² -1) component, it is possible to use a liquid or solid Lewis acids and Bronsted acids,
Specific examples thereof include various types of activated clay such as montmorillonite-based activated clay and bentonite-based activated clay, synthetic zeolite, silica-alumina, silica-magnesia, and the like. Particularly, montmorillonite-based activated clay is preferable. The addition amount of such a reaction catalyst is 1 to 20% by mass, preferably 2 to 8% by mass based on the raw material. As other reaction conditions, the reaction temperature is 20.
0 to 270 ° C, preferably 220 to 250 ° C, and the reaction pressure is normal pressure or a pressure slightly higher than normal pressure,
Specifically, the pressure is 1 to 10 atm. The reaction time varies depending on the amount of the catalyst and the reaction temperature, but is usually 5 to 7 hours. In this reaction, the reaction system tends to increase in viscosity as the reaction proceeds. After completion of the reaction, the reaction catalyst is filtered off from the reaction product solution, and then the reaction product solution is distilled under reduced pressure, for example, to distill unreacted raw materials and by-products such as branched fatty acids. (a ¹ -1) components were distilled off, thereby further a trimer by continuing distillation (a ² -1) distilling components out.

[0026] In the above, when a higher unsaturated fatty acid as a raw material, (A ¹ -1) a carboxyl group 2 has dimer acid obtained as a component, (A ² -1)
A trimer acid having three carboxyl groups as a component is obtained. In the case of using the higher unsaturated fatty acid ester as the starting material, the dimer acid diester is obtained having two ester groups as (A ¹ -1) component, (A ² -
1) A trimer acid triester having three ester groups as a component is obtained.

[0027] By obtained as described above (A ¹ -1) component to a reduction treatment (hydrogenation), dimer diol is A ¹ component is obtained and reduction treatment (A ² -1) component by, trimer triol is a ² component is obtained.

As a method of reducing the component (A ¹ -1) or the component (A ² -1), a known chemical reduction method, for example, lithium aluminum hydride (LiAlH ₄ ), lithium borohydride (LiBH ₄₎ ), Metallic sodium /
A reduction method using a hydrogenating agent such as an alcohol can be employed. To give a specific example of the reduction method, the molar ratio of the dimer (A ¹ -1) component is twice and the molar ratio of the trimer (A ² -1) component is 2 times. three times and made the amount of lithium aluminum hydride are dispersed in a solvent such as diethyl ether or dioxane, to this dispersion was diluted with diethyl ether (a ¹ -1) component or (a ²
-1) The component is gradually dropped at 0 ° C. to room temperature over 1 to 2 hours to react. (A ¹ -1) component or (A ² -
1) After the completion of the dropwise addition of the components, the mixture was stirred at room temperature for about 30 minutes, and then the reaction was terminated by gradually dropping water in an amount about 4 times the molar ratio of the added lithium aluminum hydride. Let it. Then, about 10% by weight of dilute sulfuric acid is added to the reaction solution to remove lithium aluminum from the solvent layer, and the solvent layer is washed with water until the waste liquid becomes neutral. Then, by removing the solvent of the solvent layer, is A ¹ component or A ² component which is a particular polyhydric alcohol is obtained. The specific polyhydric alcohols thus obtained are all transparent and viscous liquids at room temperature.

Further, (A ¹ -1) component or (A ² -
1) As another method for reducing the components, a catalytic reduction method using hydrogen gas can be employed. In the case of hydrogenation by the catalytic reduction method, Raney nickel, platinum-supported nickel diatomaceous earth, copper-chromium, copper-zinc or the like is used as a catalyst, and is used in a ratio of 0.1 to 7% by mass (A ¹
-1) is added to component or (A ² -1) component. As the reaction conditions, the reaction temperature is 100 to 300 ° C, preferably 250 to 280 ° C, and the pressure of hydrogen gas is normal pressure to 30 to 30 ° C.
0 kg / cm ² , preferably 150-250 kg / cm
^2, and the reaction time is 1 to 15 hours, preferably 4 to 8 hours.
Time.

Specific examples of the specific polyhydric alcohol obtained as described above include the following general formulas (1) to (4) obtained by reducing a dimer of a higher unsaturated fatty acid having 18 carbon atoms. ) dimer diol (A ¹ component represented by), the dimer diol represented by the following general formula (1) or the general formula (3), unsaturated fatty represented by the following general formula (5) or the following general formula (6) family and alcohol, may be mentioned respective trimer triol comprising coupled by reacting the unsaturated binding sites (a ² component).

[0031]

Embedded image

(Where m, n, p, q, m ', n',
p ′ and q ′ are each an integer of 0 or 1 or more, and m + n + p + q = 28, m + n = m ′ + n ′ +
1, p + q = p ′ + q ′ + 3. )

[0033]

Embedded image

(T, u, h, j and k are respectively
0 or an integer of 1 or more, t + u + 5 = 18, h +
3j + k + 4 = 18. )

In the present invention, as the alcohol component for obtaining the esterified product as the component (A), (a) a specific polyhydric alcohol is used together with the above specific polyhydric alcohol to carry out an intermolecular dehydration reaction (at the hydroxyl group site). can be obtained by condensation reaction) is, a ³ component is an ether compound having at least one alcoholic hydroxyl group, and, with a carboxylic acid corresponding to (b) a specific polyhydric alcohol, a specific polyhydric alcohol obtained by reacting, either or both of a ⁴ component is an ester compound having at least one alcoholic hydroxyl group, it can be used as needed.

The term "carboxylic acid corresponding to a polyhydric alcohol" used herein means a dimer acid, a dimer acid ester (diester), a trimer acid, or a trimer acid ester (triester) which is a precursor of a specific polyhydric alcohol. "Dimer monocarboxylic acid monoalcohol" obtained by hydrogenation, "trimerized carboxylic acid monoalcohol",
The term "trimer monocarboxylic acid diol" is used.

[0037] A ^3-component, for example, p-toluenesulfonic acid, sulfuric acid, hydrogen fluoride, Three fluoride, methanesulfonic acid, activated clay, the acid catalyst selected from synthetic zeolites, certain polyvalent as a raw material 0.1 for alcohol
10 to 10% by mass, preferably 0.5 to 5% by mass, preferably under reduced pressure at 150 to 280 ° C and 3 to 1%.
It can be obtained by subjecting a specific polyhydric alcohol to a dehydration reaction under the condition of 0 hour.

Further, A ⁴ components are, for example, for a particular polyhydric alcohol as a raw material, the carboxylic acid corresponding to the specific polyhydric alcohols mentioned above, the carboxyl group of the hydroxyl group and the latter having the former equal An acid catalyst selected from paratoluenesulfonic acid, sulfuric acid, hydrogen fluoride, hydrogen trifluoride, methanesulfonic acid, and the like, and a base selected from sodium hydroxide, lithium hydroxide, metal sodium, and the like, added in a molar amount. The catalyst is used at a ratio of 0.1 to 10% by mass, preferably 0.5 to 5% by mass with respect to the polyhydric alcohol, and is used at a temperature of 50 to 150 ° C and 3 to 10% by mass.
It can be obtained by performing an esterification reaction for a time.

Further, a specific polyhydric precursor alcohol (A ¹ component and / or A ² component) (A ¹ -1)
Component and / or (A ² -1) component, by reduction treatment by catalytic reduction method with hydrogen gas, during the resulting alcohol component, particular polyhydric alcohol (A ¹
Components and / or with A ² component), A ³ component and / or A ⁴ components are contained in a proportion to be 15% by weight of the total alcohol component. And this content ratio is
By removing water and lower alcohol by-produced during the reduction treatment, the content can be increased to 15 to 40% by mass.

The A ³ component thus obtained and / or
Or A ⁴ components, by which is contained in the alcohol component for obtaining the component [A], and improves the falling ball strength of the obtained lens (impact resistance) are also facilitates low specific gravity of the lens material Can be achieved.

The proportion of the A ³ component and the A ⁴ component in the alcohol component for obtaining the component (A) is such that the total amount of both components is 0 to 40% by mass, preferably 5 to 30% by mass.
% By mass. If this proportion exceeds 40% by mass, the viscosity of the esterified product obtained from the alcohol component and, consequently, the monomer composition becomes excessive, so that the monomer composition is difficult to handle in the polymerization treatment. Becomes

The ratio of the A ³ component to the A ⁴ component in the alcohol component for obtaining the component (A) can be appropriately selected, but usually, the A ³ component: A ⁴ component is in a mass ratio. It is used at a ratio of 9: 1 to 2: 8.

By esterifying the alcohol component obtained as described above with an acid component comprising acrylic acid or methacrylic acid, one of the monomers [A] as a direct raw material of the present invention is obtained. The components are obtained. This esterification is carried out, for example, at a molar ratio of 1.0 to 1.0 with respect to the alcohol component and the total amount of these alcoholic hydroxyl groups.
The reaction is carried out by reacting 2.0 times, preferably 1.0 to 1.5 times the amount of acrylic acid or methacrylic acid in the presence of a catalyst and necessary additives such as a polymerization inhibitor. As the catalyst, hydrogen fluoride, hydrogen trifluoride,
In addition to acid catalysts such as p-toluenesulfonic acid and methanesulfonic acid, basic catalysts such as lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium hydrogen carbonate and sodium carbonate, aluminum, sodium, potassium, titanium and the like Alkoxides of metals and alcohols such as methyl alcohol, ethyl alcohol, propyl alcohol and butyl alcohol are used, and the addition ratio thereof is 1 to 10% by mass, preferably 1 to 10% by mass, based on the total amount of the alcohol component and the acidic component. 2 to 5% by mass. Hydroquinone, p-methoxyphenol, or the like is used as a polymerization inhibitor used to suppress a side reaction in the esterification reaction, and the addition ratio thereof is 0 to the total amount of the alcohol component and the acid component. 0.0001 to 1% by mass. Other conditions include a reaction temperature of 50 to 130.
C., and the reaction time is 1 to 10 hours. If necessary, the produced component [A] can be purified by distillation under reduced pressure or washing with an aqueous alkali solution.

In addition to the direct esterification reaction between an alcohol component and an acidic component, the esterification may be performed by a transesterification reaction between an alcohol component and an ester of an acid component (eg, methyl methacrylate). Can be achieved. Examples of the catalyst used in such a transesterification reaction include the same catalysts as those exemplified as the catalyst for directly esterifying the alcohol component and the acidic component, and other conditions are the same as those in the esterification reaction. It is.

In the above, A ¹ component, A ² component, A ³
The component or A ⁴ component alone esterification respectively, by mixing the resultant esterified product, can also be prepared component [A], A ¹ component and A ² components, A ³
The mixture of components and A ⁴ component was prepared by esterifying the mixture, it is also this to prepare the component [A].

[0046] <[B] Component> (B) is the component specific radical polymerizable urethane compound, (b) a polyisocyanate consisting of compounds B ¹ component, (ii) at least one hydroxyl group and at least one those obtainable by the B ^2-component consists of those compounds having a radical polymerizable unsaturated bond in the molecule and (c) the number of carbon atoms is from aliphatic alcohols of 6 or more monovalent B ³ component is urethane reaction is there.

The polyisocyanate compound is a B ¹ component is a compound having at least two or three or more isocyanate groups in the molecule, and specific examples thereof include hexamethylene diisocyanate, octamethylene diisocyanate, isophorone diisocyanate, 2,
2,4-trimethylhexamethylene diisocyanate,
Dicyclohexylmethane diisocyanate, tetramethylene diisocyanate, tolylene diisocyanate,
4,4'-diphenylmethane diisocyanate, naphthalene diisocyanate, 3,3'-dimethyl-4,4 '
-Biuretization reaction product of bisphenylenediisocyanate, meta-xylylene diisocyanate, hexamethylene diisocyanate, compound having a trimer structure or adduct reaction product with trimethylolpropane, trifunctional to tetrafunctional polyisocyanate compound derived from isophorone diisocyanate And 2-isocyanatoethyl-2,6-diisocyanatoethylhexanoate. These compounds can be used alone or
More than one type can be used in combination.

[0048] Specific examples of the compound having a B ² hydroxyl groups and a radical polymerizable unsaturated bond is a component in the molecule, acrylic acid, methacrylic acid, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate,
3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2,3-hydroxypropyl acrylate, 2,3-hydroxypropyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 2-carboxyethyl acrylate, 2-carboxyethyl Examples include methacrylate and vinylbenzoic acid. These compounds can be used alone or in combination of two or more. By using the compound having such a hydroxyl group and a radical polymerizable unsaturated bond in the molecule as B ² component, the urethane compound obtained becomes to have a radical-polymerizable, consisting the urethane compound (B) component , [A] can be copolymerized.

[0049] Specific examples of the aliphatic alcohols B ³ is the component carbon atoms of 6 or more monovalent, lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol. These compounds can be used alone or in combination of two or more. By such number of carbon atoms is used an aliphatic alcohol of 6 or more monovalent as B ³ component, a is a specific polymerizable urethane compound obtained component [B],
The esterified product (A) and the copolymerizable monomer (C) described later have high compatibility with the copolymerizable monomer, and the copolymer obtained from these mixed monomers has excellent properties. It has optical characteristics.

In the present invention, the urethanization reaction of the component B ^{1 with the} components B ² and B ³ can be carried out in an organic solvent which is inert to this reaction. By removing the above, a radically polymerizable urethane compound as the component [B] is obtained. Further, when the reaction system (B ¹ component, a mixture of B ^2-component and B ³ component) exhibiting the liquid state, without the use of organic solvents,
The urethanization reaction of the B ¹ component, the B ² component and the B ³ component can be performed. Further, the urethanization reaction can be performed in the presence of the component [A] and the component [C] described below. In this case, the obtained reaction product solution can be used as it is as a mixed monomer, which is preferable.

The urethanization reaction between the B ¹ component, the B ² component and the B ³ component occurs only by heating the reaction system. From the viewpoint of shortening the reaction time, usually, an appropriate urethanization reaction catalyst is used. used. Examples of such a urethanization reaction catalyst include di-n-butyltin dilaurate, stannas octoate, dimethyltin dichloride, stannic chloride and the like.

[0052] and B ¹ component to be subjected to the urethanization reaction, the ratio of the B ^2-component and B ³ component, the number of moles of isocyanate groups of the B ¹ component a, B ² component and B ³ components Assuming that the number of moles of the hydroxyl group is b, the molar ratio (a / b) is 0.5 to 2.0, particularly 0.75 to 2.0.
It is preferably 1.5. When the value of the molar ratio (a / b) is less than 0.5, the obtained copolymer is
It tends to have low durability. On the other hand, this molar ratio (a
When the value of / b) exceeds 2.0, the obtained copolymer tends to be discolored.

<Component (C)> The copolymerizable monomer that is the component (C) is one that can be copolymerized with the components (A) and (B) described above and the component (D) described below. If the specific gravity is not more than 1.02, preferably 0.95 to
1.015, the refractive index of which is 1.45 to 1.60, which is appropriately selected so as to obtain a copolymer satisfying mechanical properties and optical properties required for an optical material. is there. Specifically, a compound having an acryloyl group, a methacryloyl group, a vinyl group, or the like in a molecule can be used as the copolymerizable monomer as the component [C].

Specific examples of the compound having an acryloyl group or a methacryloyl group in the molecule include methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, and t-butyl (meth) acrylate. (Meth) acrylates having an aliphatic alkyl group such as acrylate, n-hexyl (meth) acrylate, and isostearyl (meth) acrylate; phenyl (meth) acrylate, cyclohexyl (meth) acrylate, naphthyl (meth) acrylate, (Meth) having an aromatic or alicyclic group such as 2,3-tribromophenyl (meth) acrylate
Acrylates; ethylene glycol di (meth) acrylate, polyethylene glycol poly (meth) acrylate, propylene glycol di (meth) acrylate,
Butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, Tetramethylolmethanetri (meth) acrylate, tetramethylolmethanetetra (meth) acrylate, 2,2-bis [4- (meth) acryloxyethoxyphenyl] propane, 2,2
And polyfunctional (meth) acrylates such as -bis [4- (meth) acryloxypolyethoxyphenyl] propane. In the above, “(meth) acrylate” means “acrylate” or “methacrylate”.

As the compound having a vinyl group in the molecule, an aromatic vinyl compound having an aromatic ring is preferably used because the refractive index of the obtained copolymer can be increased. Specific examples of such an aromatic vinyl compound include styrene, t-butylstyrene, α-methylstyrene, divinylbenzene, 4-chlorostyrene,
Chloromethylstyrene, 4-hydroxymethylstyrene, ethylstyrene, o-methylstyrene, 4-methoxystyrene and the like can be mentioned. These compounds having an acryloyl group, a methacryloyl group or a vinyl group can be used alone or in combination of two or more.

Of these compounds, it is preferable to use divinylbenzene as part or all of the component (C), and it is particularly preferable to use 3 to 25% by mass of the mixed monomer. By using divinylbenzene as the component (C), a synthetic resin lens material having an excellent balance of specific gravity, optical properties, mechanical properties, and the like can be obtained. It is particularly preferable to use at least one selected from t-butyl (meth) acrylate, styrene and t-butylstyrene together with divinylbenzene as the component (C).

<Component (D)> The specific unsaturated isocyanate compound as the component (D) is represented by the above structural formula (I) having (1) a (meth) acryloyl group and an isocyanate group in the molecular structure. The compound is (2) at least one unsaturated isocyanate compound selected from the aromatic compounds represented by the structural formula (II) having a radically polymerizable unsaturated bond and an isocyanate group in the molecular structure.

Here, specific examples of the compound represented by the structural formula (I) include acryloyl isocyanate, methacryloyl isocyanate, acryloylethyl isocyanate, methacryloylethyl isocyanate, acryloylethoxyisocyanate, methacryloylethoxyisocyanate and the like.

Specific examples of the compound represented by the above structural formula (II) include 1- (2-isocyanatopropyl)
-3-isopropenylbenzene, 1- (2-isocyanatopropyl) -4-isopropenylbenzene and the like can be mentioned.

<Monomer composition> The monomer composition for obtaining the copolymer constituting the synthetic resin lens material of the present invention is as follows:
The above component (A), a mixed monomer composed of the component (B) and the component (C), or a mixed monomer composed of the component (A), the component (D) and the component (C). It becomes.

The component [A] in this mixed monomer,
As the respective proportions of the ([B] component or [D] component) and the [C] component, the proportion of the [A] component is 30 to 90.
% By mass, preferably 40 to 80% by mass, the ratio of the component [B] or [D] is 0.5 to 20% by mass, preferably 1 to 10% by mass, and the ratio of the component [C] is 9.5 to 5%. It is 65% by mass, preferably 15 to 50% by mass. When the proportion of the component (A) is less than 30% by mass, it is difficult to obtain a copolymer having good mechanical properties and a specific gravity of 1.02 or less. On the other hand, the proportion of the component (A) is 90% by mass.
When it exceeds, the obtained copolymer has high flexibility, and good mechanical properties cannot be obtained. When the proportion of the component (B) or the component (D) is less than 0.5% by mass, it becomes difficult to obtain a synthetic resin lens material having high adhesion to the hard coat layer and the primer layer. on the other hand,
When the ratio of the component (B) or the component (D) exceeds 20% by mass, the effect according to the amount of the component is not obtained, and the specific gravity of the obtained copolymer tends to increase. When the proportion of the component (C) is less than 9.5% by mass,
The obtained copolymer has high flexibility, and good mechanical properties cannot be obtained. On the other hand, when the proportion of the component [C] is 6
If it exceeds 5% by mass, it has good mechanical properties,
Moreover, it is difficult to obtain a copolymer having a specific gravity of 1.02 or less.

The monomer composition usually contains a polymerization initiator and a molecular weight regulator in addition to the above-mentioned mixed monomer.
In the present invention, it is preferable to use a dimer of α-methylstyrene as the molecular weight regulator, since the influence on the transparency and color tone of the obtained copolymer is small. Such a dimer of α-methylstyrene is preferably contained in the monomer composition at a ratio of 0.1 to 5% by mass based on the mixed monomer. When this proportion is less than 0.1% by mass, the resulting copolymer is liable to cause optical distortion (striae), while when this proportion exceeds 5% by mass, the obtained weight is low. It is not preferable because the heat resistance and mechanical performance of the coalescence may be reduced. Further, the above monomer composition may contain an antistatic agent, a colorant, an ultraviolet absorber, a heat stabilizer, an antioxidant, a filler, and the like, as necessary.

By subjecting such a monomer composition to a polymerization treatment, a copolymer constituting the synthetic resin lens material of the present invention can be obtained. As the polymerization method, a method such as radical polymerization, ionic polymerization, or photopolymerization can be used, and a method using a usual radical polymerization initiator or a photopolymerization initiator is preferable. For example, in the method by radical polymerization, the polymerization is performed at a temperature of 30 to 120 ° C. using a radical polymerization initiator capable of initiating a polymerization reaction. Further, in the method by photopolymerization, the reaction is carried out at about room temperature,
A high-pressure mercury lamp or a low-pressure mercury lamp is used as a light source.

In the present invention, since the component [A] constituting the mixed monomer is a polyfunctional monomer, a crosslinked structure is introduced into the copolymer obtained from the mixed monomer. .
Therefore, it is difficult to use this copolymer as a molding material in a molding method involving melting or melting. Therefore, as a method of polymerizing a mixed composition, a desired lens shape can be directly obtained. It is preferable to apply a type polymerization method.

The casting polymerization method is a well-known technique and can be applied to the present invention as it is. As a container for casting polymerization, a plate or a lens, a cylinder, a prism, a cone, a sphere, or any other mold or mold designed according to the purpose or application can be used. The material of the container can be selected from inorganic glass, plastic, metal, and any other material depending on the purpose. The actual polymerization reaction is
The polymerization is carried out by injecting a monomer composition containing a polymerization initiator into a container for casting polymerization and heating.
The monomer in the monomer composition is preliminarily reacted to a certain extent by using another reaction vessel, and the prepolymer or syrup having increased viscosity is injected into a casting polymerization vessel to complete the polymerization. You can also. The required monomer components and the polymerization initiator may be mixed in their entirety at once, or may be mixed stepwise.

As means for obtaining an actual optical lens using the synthetic resin lens material of the present invention, in addition to means for directly obtaining an optical lens having a specific shape by a casting polymerization method, a plate-like or It is also possible to use a means for obtaining a massive synthetic resin lens material and shaving a lens having a desired shape from the lens material. The lens obtained as described above can be subjected to a surface polishing treatment, an antistatic treatment, and other post-treatments as necessary. Also, for the purpose of increasing the surface hardness of the lens,
By coating an appropriate inorganic material or organic coating agent, a hard coat layer or a primer layer can be formed.

According to the present invention, the mixed monomer for obtaining the copolymer constituting the copolymer is obtained by esterifying an alcohol component containing a specific polyhydric alcohol with acrylic acid or methacrylic acid. Since component (A) is contained as an essential monomer component, a synthetic resin lens material having excellent mechanical properties and an extremely low specific gravity of 1.02 or less can be obtained. Moreover, since the mixed monomer contains the component [B] composed of a specific radically polymerizable urethane compound or the component [D] composed of a specific unsaturated isocyanate compound as an essential monomer component, A lens having high adhesion to a coat layer or a primer layer can be formed.

[0068]

Hereinafter, embodiments of the present invention will be described.
The present invention is not limited by these. In addition,
In the following examples, the amount of polymerization charged is indicated by pure content unless otherwise specified. "Parts" means "parts by mass"
And “%” means “% by mass” except for those relating to the releasability of the hard coat layer and the transparency of the lens material.

Various properties of the lens materials obtained in the following Examples and Comparative Examples were evaluated as follows. (1) Specific gravity: measured according to ASTM D792. (2) Refractive index: The refractive index at 20 ° C. was measured with an Abbe refractometer. (3) Releasability of the hard coat layer: The surface of the lens material was ultrasonically cleaned using isopropyl alcohol and dried, and then subjected to a Tesla coil discharge treatment for 30 seconds. Then
A silicone-based hard coat agent “TS-56H” (manufactured by Tokuyama Soda Co., Ltd.) is applied to the surface of the lens material by an immersion method, left at room temperature for 30 minutes, and then heat-cured at 120 ° C. for 2 hours. A hard coat layer was formed on the surface of the lens material. The lens material having the hard coat layer formed on the surface is used as a test piece, and a weather meter (ATLAS: Ci35) is used for the test piece.
Was performed for 100 hours, and then a cross-cut tape test was performed 10 times on the surface of the test piece, and the percentage (%) of the peeled hard coat layer was measured. (4) Impact resistance: weight 16.
When a steel ball of 33 g was dropped on a test piece (lens material) from a height of 127 cm, the presence or absence of breakage of the test piece was examined.
Those that were not destroyed were marked with “O”, and those that were destroyed were marked with “X”. (5) Transparency: Visible light transmittance was measured according to JIS K7105, and those having a visible light transmittance of 90% or more were rated as ○, and those less than 90% were rated as x.

(1) Preparation of component [A]: <Preparation example 1 of component [A]> 72% of methyl oleate, 18% of methyl linoleate, and 10% of higher saturated fatty acid methyl
% Of a mixture of higher unsaturated fatty acid methyl esters containing 70% and 70 g of activated clay in an autoclave having a capacity of 2 liters under a nitrogen atmosphere at 230 ° C.
For 5 hours. From the obtained reaction product liquid, the unreacted higher unsaturated fatty acid methyl ester fraction and the isomerized higher unsaturated fatty acid methyl ester fraction were separated at 230 ° C./1 Ton.
It was removed by vacuum distillation under the conditions of rr, by molecular distillation the residue under the conditions of ^{280 ℃ / 0.1Torr, (A 1} -1) is the component dimer acid ester (dimethyl ester) of about 450 g were obtained. Then
To 400 g of the obtained dimer acid ester, 12 g of a copper-chromium catalyst (a ratio of 3% based on the dimer acid ester) was added, and a hydrogen gas pressure of 220 kg / cm ² and a temperature of 2 were added.
The reaction conditions of 70 ° C., by performing hydrogenation with a 3 hours catalytic reduction over 10 hours while introducing 10 min of hydrogen gas for each, dimer diol (A ¹ component) 85%
When, generated by intermolecular dehydration of dimer diol, a polyol compound having an ether bond (A ³ component) and 12% alcohol (A ⁴ having an ester bond
(Hereinafter referred to as “alcohol component (1)”). 340 g were obtained. The hydroxyl value of this alcohol component (1) is 180 KOHmg /
g. By performing such an operation, a total of 1000 g or more of the alcohol component (1) was prepared.

A 5-liter flask having an internal capacity of 5 liters is equipped with a stirrer, a thermometer, a dropping funnel, a nitrogen inlet tube and an air inlet tube (the nitrogen inlet tube is arranged so that its tip is immersed in the raw material in the flask. , The air introduction tube was arranged so that the tip is located in the head space.) And two condensers (the first condenser was directly connected to the reaction tank, and the second condenser was connected to the first condenser by a T-shaped connecting pipe. To prevent the liquid condensed by the second condenser from returning to the reaction tank.) To form a reaction apparatus.

In a flask of this reactor, 1000 g of the alcohol component (1) and methyl methacrylate 3
42 g and 0.61 g of 2,4-dimethyl-6-t-butylphenol were charged, and the temperature was raised to the reaction temperature while introducing nitrogen gas into the raw material liquid in the flask.
The pressure in the flask was reduced to 10 torr over 1 hour to remove water from the raw material liquid. Next, by introducing nitrogen gas, the inside of the flask was returned to normal pressure, then nitrogen gas was introduced into the raw material liquid, and while introducing air into the head space inside the flask, titanium was introduced into the flask. Tetraisopropoxide 18.9
g is dissolved in 200 g of n-hexane,
The alcohol component (1) was esterified by transesterification by gradually adding it over 2 hours with a dropping funnel. At this time, set the first condenser to 5
By setting the temperature to 0 ° C. (the azeotropic temperature of n-hexane and methanol) and setting the second condenser to 0 ° C.,
Methyl methacrylate was refluxed by the first condenser, and n-hexane and methyl alcohol were condensed by the second condenser. The n-hexane was recovered and returned to the flask. The transesterification was carried out until no more methyl alcohol was distilled off. After terminating the transesterification reaction, excess n-
Hexane and methyl methacrylate are removed under reduced pressure, and 1
The catalyst was hydrolyzed by adding activated carbon and water while maintaining the temperature at 00 ° C. and stirring for 1 hour. Thereafter, the pressure inside the flask was reduced under the conditions of 80 ° C. and 10 torr, thereby removing excess water in the flask. To the obtained reaction product, 6.25 g of a filter aid "Hyflo Super Cell" (manufactured by Celite) was added, and the mixture was stirred. Thereafter, the reaction product was filtered at 80 ° C. to obtain an alcohol component (1). [A] component (hereinafter referred to as “[A] component (1)”) which is an esterified product of methacrylic acid and methacrylic acid was prepared.

<Preparation Example 2 of Component (A)> An alcohol component (1) was prepared in the same manner as in Preparation Example 1, and 200 g of the alcohol component (1) was subjected to molecular distillation (250 ° C./0.1 Ton).
By rr), almost 100% of dimer diol (A ¹ Ingredients: hydroxyl value 199KOHmg / g) [hereinafter, this is referred to as "alcohol component (2)". 160
g was obtained. Preparation Example 1 using this alcohol component (2)
By performing the same operation as described above, component [A], which is an esterified product of alcohol component (2) and methacrylic acid (hereinafter referred to as “[A] component (2)”) was prepared.

<Preparation Example 3 of Component (A)> An alcohol component (2) was prepared in the same manner as in Preparation Example 2, and 100 g of the alcohol component (2) was added with 2 g of acidic activated clay, and the mixture was added under a nitrogen atmosphere. A dehydration reaction was performed at 200 ° C. for 10 hours. After completion of the reaction, was filtered off activated clay from the reaction solution obtained, the unreacted dimer diol (A ¹ component) was removed by molecular distillation, which is produced by the intermolecular dehydration of dimer diol ether polyol compounds having a bond (a ³ components: a hydroxyl value 103KOHm
g / g) 75 g were obtained. Then, A ¹ component and A ³ component and the mixture was mixed at a ratio at which the mass ratio of 90:10 [hereinafter, this is referred to as "alcohol component (3)". ] Was obtained. By performing the same operation as in Preparation Example 1 using this alcohol component (3), the component [A], which is an esterified product of the alcohol component (3) and methacrylic acid (hereinafter, referred to as “A”)
This is designated as “[A] component (3)”. ) Was prepared.

<Preparation Example 4 of Component (A)> 1000 g of a mixture of higher unsaturated fatty acid esters containing 75% of methyl oleate, 15% of methyl linoleate and 9% of methyl stearate, and 70 g of montmorillonite activated clay
Were reacted at 230 ° C. for 5 hours in a 2 liter autoclave under a nitrogen atmosphere. After filtering the catalyst from the reaction product solution, the reaction product solution is subjected to molecular distillation to remove the monomer fraction distilled at a temperature of 200 to 220 ° C. at 0.3 to 0.5 mmHg, thereby obtaining (A ¹
About 450 g of a dimer acid ester (dimethyl ester) as the (-1 component) and about 150 g of a trimer acid ester (trimethyl ester) as the (A ² -1) component were obtained.
200 g of the dimer acid ester and 50 g of the trimer acid ester were mixed to obtain a mixed solution having a mixing ratio of 80:20. Next, 250 g of the mixed solution was diluted with 350 ml of diethyl ether to prepare a diluted solution.

On the other hand, after replacing the inside of a reactor equipped with a stirrer, a cooling pipe, a thermometer, a dropping funnel and a nitrogen gas inlet pipe with nitrogen gas, 32 g of lithium aluminum hydride was charged into the reactor, and a nitrogen gas atmosphere was charged. Under stirring at room temperature, 1200 ml of diethyl ether was gradually added using a dropping funnel to prepare a dispersion of lithium aluminum hydride. The diluent prepared above was added dropwise to this dispersion over about 2 hours to cause a reaction. At this time, the temperature of the reaction system was maintained at about 30 ° C. After completion of the dropwise addition, the reaction system was left for 30 minutes, and then 65 g of water was gradually added dropwise using a dropping funnel. The reaction product thus obtained was slowly transferred to a beaker containing 350 g of ice,
250 g of a 10% sulfuric acid aqueous solution is added into the beaker,
Further, an appropriate amount of diethyl ether was added to extract an ether layer. Then, the extracted ether layer was washed with water until the effluent is neutral, by a solvent of the resultant ether layer was distilled off under reduced pressure, dimer diol (A ¹ component) 80%
If, trimer triol (A ² component) mixture of 20% [hereinafter, this is referred to as "alcohol component (4)". ] 2
10 g were obtained. This alcohol component (4) is a transparent viscous liquid having a hydroxyl value of 190 KOHmg.
/ G.

The same operation as in Preparation Example 1 was carried out using this alcohol component (4) to obtain an ester [A] consisting of an esterified product of the alcohol component (4) and methacrylic acid.
A component (hereinafter, referred to as “[A] component (4)”) was prepared.

[0078] (2) [B] component of Preparation: a cyclic trimer 23.0 parts of hexamethylene diisocyanate is a B ¹ component <component [B] Preparation Example 1> is the B ² component 2-hydroxy butyl methacrylate 6.1 parts, isostearyl alcohol 20.9 is B ³ component
Of the (A) component (1) and 50.0 parts of t-butyl methacrylate as the (C) component, and dissolving the resulting mixture. Was prepared. In the above, the molar number a of the isocyanate groups of the B ¹ component, the value of the molar ratio of the moles b of hydroxyl groups in the B ² component Oyohi B ³ component (a / b) 1.
0. This component [B] prepared for mixture, di-n- butyl laurate 0.03 parts were added and mixed as a urethanization reaction catalyst, over a period of 2 hours at 55 ° C., and B ¹ component, B
By reacting a ^2-component Oyohi B ³ component, consisting of a radical polymerizable urethane compound (B) component (hereinafter,
This is designated as “[B] component (1)”. ) (Hereinafter referred to as “mixture (1)”).
The ratio of the component [A], the component [B], and the component [C] in the mixture (1) was 1: 1: 1 by mass.

<Preparation Example 2 of Component [B]> B The amount of the cyclic trimer of hexamethylene diisocyanate, which is the component ¹ , is 2
The amount of 2-hydroxybutyl methacrylate as the B ² component was changed to 13.4 parts and the amount of isostearyl alcohol as the B ³ component was changed to 11.4 parts in 5.2 parts, and [A]
[A] Component (2) 5 instead of Component (1) 50.0 parts
Except that 0.0 part was used, in the same manner as in Preparation Example 1, a component [B] composed of a radically polymerizable urethane compound (hereinafter referred to as “[B] component (2)”) was contained. A mixture (hereinafter, referred to as “mixture (2)”) was obtained. In the above, the molar number a of the isocyanate groups of the B ¹ component, the value of the molar ratio of the moles b of hydroxyl groups in the B ² component Oyohi B ³ component (a / b) is 1.0.
The ratio of the component [A], the component [B], and the component [C] in the mixture (2) was 1: 1: 1 by mass.

<Preparation Example 3 of Component (B)> In place of 50.0 parts of Component (A) (5), 50.0 parts of Component (A) (3) were used.
Component (B) comprising a radically polymerizable urethane compound in the same manner as in Preparation Example 1 except that styrene 50.0 was used instead of t-butyl methacrylate 50.0 parts as the component (C). Hereinafter, this mixture is referred to as “[B] component (3)” (hereinafter, referred to as “mixture (3)”).

<Preparation Example 4 of Component [B]> In place of 50.0 parts of [A] component (1), 50.0 parts of [A] component (4) were used.
Component (B) comprising a radically polymerizable urethane compound in the same manner as in Preparation Example 1 except that styrene 50.0 was used instead of t-butyl methacrylate 50.0 parts as the component (C). Hereinafter, this mixture is referred to as “[B] component (4)” (hereinafter, referred to as “mixture (4)”).

<Preparation Example of Comparative Radical-Polymerizable Urethane Compound> The amount of the cyclic trimer of hexamethylene diisocyanate, which is the B ¹ component, was 22.8 parts, and the amount of the B ² component, which was 2
- the amount of hydroxybutyl methacrylate was changed to 22.2 parts, B ³ except for not using the isostearyl alcohol as the component in the same manner as in Preparation Example 1, a radical polymerizable urethane compound (hereinafter, "Compare this (Hereinafter referred to as “mixture (5)”).

<Example 1> 1.5 parts of mixture (1) (0.5 part of component (A), 0.5 part of component (B)
And 0.5 parts of t-butyl methacrylate as the component (C)), 68.0 parts of the component (A) (21.5 parts), and 21.5 parts of t-butyl methacrylate (the component (C)).
Part and 9 parts of divinylbenzene ([C] component) by mixing 68.5% of [A] component and 0.1 part of [B] component.
A mixed monomer composed of 5% and 31% of the component [C] was prepared. A monomer composition was prepared by adding and mixing 1 part of lauroyl peroxide as a radical polymerization initiator to 100 parts of the mixed monomer. This monomer composition is poured into a glass lens mold, and is heated at 50 ° C. for 10 hours, at 60 ° C. for 8 hours, at 80 ° C. for 3 hours, at 100 ° C.
By heating at a different temperature sequentially for 2 hours at a different temperature to carry out the polymerization treatment of the monomer composition, the thickness is 1.5 mm
Produced a -2.00 diopter lens.

Example 2 6.0 parts of the mixture (1)
[A] 65.0 parts of component (1), 20 parts of t-butyl methacrylate ([C] component) and 9 parts of divinylbenzene ([C] component) are mixed to obtain 67% of [A] component. , [B] component 2% and [C] component 31% were prepared. Except for using this mixed monomer, in the same manner as in Example 1, the thickness was 1.5 mm,
A -2.00 diopter lens was produced.

Example 3 15.0 parts of the mixture (1)
By mixing 59.0 parts of [A] component (1), 17 parts of t-butyl methacrylate ([C] component), and 9 parts of divinylbenzene ([C] component), 64% of [A] component is obtained. A mixed monomer comprising 5% of the component [B] and 31% of the component [C] was prepared. Except for using this mixed monomer, in the same manner as in Example 1, the thickness was 1.5 mm,
A -2.00 diopter lens was produced.

Example 4 In Example 1, 1.5 parts of mixture (2) (0.5 parts of component (A), 0.5 part of component (B), instead of 1.5 parts of mixture (1) 2) 0.5
(A mixture of 0.5 parts of t-butyl methacrylate as the component (C)) and 68.0 parts of the component (A).
Using 68.0 parts of [A] component (2) instead of parts,
Except that a mixed monomer composed of 68.5% of [A] component, 0.5% of [B] component and 31% of [C] component was prepared, the thickness was 1.5 mm, and -2. A 00 diopter lens was produced.

<Example 5> In Example 2, 6.0 parts of the mixture (2) was used instead of 6.0 parts of the mixture (1), and [5.0%] was used instead of 65.0 parts of the component (A) (1). [A] 67% of component (B) using 65.0 parts of component (2)
In the same manner except that a mixed monomer composed of 2% of the component and 31% of the [C] component was prepared,
A 2.00 diopter lens was produced.

<Example 6> In Example 3, 15.0 parts of the mixture (2) was used in place of 15.0 parts of the mixture (1), and [5] parts were used instead of 59.0 parts of the component (A) (1). A) Using 64 parts of component (2), 64% of component [A]
A thickness of 1.5 mm was obtained in the same manner except that a mixed monomer composed of 5% of the component [B] and 31% of the component [C] was prepared.
Produced a -2.00 diopter lens.

Example 7 In Example 2, 6.0 parts of mixture (3) (2.0 parts of component (A), 2.0 parts of component (B), instead of 6.0 parts of mixture (1) 3) 2.0
(Parts and a mixture of 2.0 parts of styrene as the component (C))
And [A] instead of 65.0 parts of the component (A).
Component (3) 65.0 parts, t-butyl methacrylate 20
A 1.5 mm-thick, -2.00 diopter lens was produced in the same manner except that 20 parts of styrene were used instead of parts.

<Example 8> In Example 2, 6.0 parts of mixture (4) (2.0 parts of component (A), 2.0 parts of component (B) instead of 6.0 parts of mixture (1) 4) 2.0
(Parts and a mixture of 2.0 parts of styrene as the component (C))
And [A] instead of 65.0 parts of the component (A).
Component (4) 65.0 parts, t-butyl methacrylate 20
A 1.5 mm-thick, -2.00 diopter lens was produced in the same manner except that 20 parts of styrene were used instead of parts.

Example 9 In Example 2, the amount of component (A) was changed from 65.0 parts to 47 parts, the amount of t-butyl methacrylate was changed from 20 parts to 22 parts, and the amount of divinylbenzene was changed. Was changed from 9 parts to 7 parts, and 18 parts of isostearyl methacrylate ([C] component) was further added to obtain a mixture comprising [A] component 49%, [B] component 2% and [C] component 49%. A lens having a thickness of 1.5 mm and a -2.00 diopter was produced in the same manner except that the monomer was prepared. The composition of the mixed monomer prepared in Examples 1 to 9 and the test results are shown in Table 1 below.

[0092]

[Table 1]

As is evident from the test results in Table 1, the lenses obtained in Examples 1 to 9 all have extremely small specific gravities of 1.02 or less, and have low refractive index and visible light transmittance. High, excellent impact resistance, and
It was confirmed that the adhesiveness with the hard coat layer was high.

Comparative Examples 1-4 A lens having a thickness of 1.5 mm and a diopter of -2.00 diopters was prepared in the same manner as in Example 1 except that a mixed monomer was prepared in accordance with the composition shown in Table 2 below. Was manufactured. <Comparative Example 5> In Example 5, 6.0 parts of the mixture (5) was replaced with 6.0 parts of the mixture (2) (component (A) 2.0).
Parts, a mixture of 2.0 parts of the component (b) for comparison (2.0 parts of t-butyl methacrylate as the component (C)) and a thickness of 1.5 mm. −
A 2.00 diopter lens was produced. <Comparative Example 6> In Example 6, mixture (2) 15.0 was used.
In the same manner except that 15.0 parts of the mixture (5) was used in place of the parts, a lens having a thickness of 1.5 mm and -2.00 diopters was produced. Table 2 below shows the monomer compositions of the mixed monomers prepared in Comparative Examples 5 and 6, and the test results of Comparative Examples 1 to 6.

[0095]

[Table 2]

As is evident from the test results in Table 2, the lenses obtained in Comparative Examples 1 to 6 did not use the component [B], and thus had low adhesion to the hard coat layer. Is understood. Also,
[B] instead of component, in Comparative Examples 5 and 6 using a the [b] component (1) comparison prepared without a B ³ component, which is obtained copolymer was cloudy This was unsuitable as a lens material.

Example 10 A monomer composition was prepared in the same manner as in Example 3, except that 1 part of a dimer of α-methylstyrene was added to 100 parts of the mixed monomer. . Each of the monomer compositions has a diameter of 80 mm.
Then, by injecting into a glass lens mold having a thickness of 3 mm and 8 mm and polymerizing the monomer composition under the same conditions as in Example 1, a lens having a thickness of 3 mm and a thickness of 8 mm Was manufactured. Each of these lenses has a small specific gravity of 0.998, has a high refractive index and a high visible light transmittance, has excellent impact resistance, and has high adhesion to a hard coat layer. Was. Further, when these lenses were observed and their optical distortion (striation) was examined, no optical distortion was observed in any of the lenses. On the other hand, using the monomer composition prepared in the same manner as in Example 3, a lens having a thickness of 3 mm and a lens having a thickness of 8 mm were produced in the same manner as described above, and the optical distortion was examined. 3mm
No optical distortion was observed in the lens No., but optical distortion was observed in the lens having a thickness of 8 mm. From the above results, it is possible to prevent or suppress the occurrence of optical distortion (striation) in the obtained copolymer by including a dimer of α-methylstyrene in the monomer composition. Is understood.

<Example 11> [A] Component (3) 67.0
Parts, 1- (2-isocyanatopropyl) -3-isopropenylbenzene ([D] component), 2.0 parts, t-butyl methacrylate ([C] component) 14.0 parts, and 4-t
A mixed monomer was prepared by mixing 10.0 parts of -butylstyrene ([C] component) and 7.0 parts of divinylbenzene ([C] component). A monomer composition was prepared by adding and mixing 1 part of lauroyl peroxide as a radical polymerization initiator to 100 parts of the mixed monomer. This monomer composition was poured into a glass lens mold, and the monomer composition was polymerized under the same conditions as in Example 1 so that the thickness was 1.5 mm.
Was manufactured. The obtained lens has an extremely small specific gravity of 0.991, a high refractive index of 1.511, a high releasability of the hard coat layer of 0%, excellent adhesion to the hard coat layer, and even a steel ball drop test. It was not broken, had excellent impact resistance, and had a high visible light transmittance of 90% or more.

<Example 12> As the component [D], 1-
A mixed monomer and a monomer composition were prepared in the same manner as in Example 11 except that 2.0 parts of methacryloylethyl isocyanate was used instead of (2-isocyanatopropyl) -3-isopropenylbenzene. By performing the polymerization treatment of the monomer composition, a thickness of 1.5
mm. The obtained lens has a very small specific gravity of 0.992, a high refractive index of 1.509, a high releasability of the hard coat layer of 0%, excellent adhesion to the hard coat layer, and even a steel ball drop test. It was not broken, had excellent impact resistance, and had a high visible light transmittance of 90% or more.

[0100]

The synthetic resin lens material of the present invention has an extremely small specific gravity of 1.02 or less, has excellent transparency, has a high refractive index, and has suitable optical characteristics required for an optical lens. In addition, it has excellent mechanical properties such as impact resistance,
Moreover, an optical lens having high adhesion to the hard coat layer and the primer layer can be formed.

Claims (5)

[Claims] 1. A mixed monomer comprising 30 to 90% by mass of the following component [A], 0.5 to 20% by mass of the following component [B], and 9.5 to 65% by mass of the following component [C]. Is obtained by polymerizing a monomer composition containing
A synthetic resin lens material comprising a copolymer having a specific gravity of 1.02 or less. Component [A]: the following A ¹ component and at least one polyhydric alcohol 60-100 wt% selected from the following A ² component, and at least one compound selected from the following A ³ component and below A ⁴ components An ester obtained from an alcohol component consisting of 40 to 0% by mass and an acid component consisting of acrylic acid or methacrylic acid. [A ¹ component]: dimer diol obtained by carbon atoms to reduction treatment dimers of higher unsaturated fatty acids is 11 to 22, and reduction treatment dimer of a lower alcohol esters of the higher unsaturated fatty acid At least one diol selected from dimer diols obtained by the above method. [A ² component]: reduction treatment trimer of a lower alcohol ester of carbon number trimer triol obtained by reduction treatment trimer of higher unsaturated fatty acids is 11 to 22, and the higher unsaturated fatty acid At least one triol selected from trimer triols obtained by the above method. [A ³ Component]: A ¹ component and at least one polyhydric intermolecular ether compound obtained by a dehydration reaction of an alcohol selected from A ² component. [A ⁴ Component]: A ¹ component and A ² and a polyhydric alcohol of at least one selected from the components, the polyhydric hydroxyl group-containing ester compound obtained by reacting the corresponding carboxylic acid to alcohol. Component [B]: the following B ¹ component and the radical polymerizable urethane compound obtained by reacting the following B ² component and below B ³ component. [B ¹ component]: a polyisocyanate compound. [B ² Component]: at least one hydroxyl group and at least one radical polymerizable unsaturated bond compound having in the molecule. [B ³ Component]: fatty alcohols having 6 or more monovalent carbon. Component [C]: a monomer copolymerizable with the component [A] and the component [B]. 2. The component (A) according to claim 1, wherein the component is 30 to 90.
2. A monomer containing a mixed monomer consisting of 0.5% by mass, 0.5 to 20% by mass of the following component [D], and 9.5 to 65% by mass of the component [C] according to claim 1. A synthetic resin lens material comprising a copolymer having a specific gravity of 1.02 or less, obtained by polymerizing the composition. [D] Component: at least one unsaturated isocyanate compound selected from the compound represented by the following structural formula (I) and the compound represented by the following structural formula (II). Embedded image 3. The mixed monomer has t as a component [C].
2. A composition comprising at least one selected from -butyl (meth) acrylate, styrene and t-butylstyrene, and divinylbenzene.
Or the synthetic resin lens material according to claim 2. 4. The mixed monomer according to claim 1, wherein divinylbenzene is contained as a component (C) in a proportion of 3 to 25% by mass. Synthetic resin lens material. 5. The monomer composition according to claim 1, wherein a dimer of α-methylstyrene is contained in a proportion of 0.1 to 5% by mass of the mixed monomer. To claim 4
The synthetic resin lens material according to any one of the above.