KR100496911B1 - A Material for Plastic Lense - Google Patents

Abstract

The present invention relates to a substance 1 of component (3) such as styrene monomer in 10 to 50 wt% of the substance of component (1) represented by the following formula (1) and 10 to 60 wt% of the substance of component (2) represented by the following formula (2): The present invention relates to an optical resin composition obtained by mixing -80 wt%. The optical material of the present invention can be used as a raw material for plastic lenses having a high refractive index and high Abbe number.

[Formula 1]

(Wherein R ₁ represents a hydrogen atom or a methyl group)

[Formula 2]

(Herein, an integer of n = 1 to 3 is represented, an integer of m = 0 to 6 is represented, R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a hydrogen atom or a halogen atom.)

Description

Optical resin composition {A Material for Plastic Lense}

The present invention is useful as an optical material such as a plastic lens, more specifically, excellent optical properties such as light weight, impact resistance, moldability, dyeing, transparency, and especially have a high refractive index (n = 1.60) It relates to a plastic lens material having high properties.

Conventionally, plastic lenses have been introduced to overcome the high specific gravity and low impact resistance of glass lenses. Representative examples include polyethylene glycol bis aryl carbonate, modified diaryl phthalate, and ethylene glycol bis aryl carbonate copolymer. Can be. However, these lenses are excellent in moldability, dyeing property, hard coat coating adhesion, impact resistance, etc., but the refractive index is about 1.50 and 1.55, so the edge of the lens is thick. Therefore, the demand for high refractive index in the optical lens has become stronger, and various proposals have been introduced for attempting high refractive index of the lens.

In the patent publication KR-90-7871, a method of manufacturing a plastic lens was introduced by injection molding a mixture of metha xylene diisocyanate and 1,2-dimercaptobenzene into a glass mold treated with a silicone release agent. This lens has excellent transparency, processability, impact resistance and light resistance, but has a low Abbe number. Abbe's number is an intrinsic value that defines the property that the refractive index changes according to the wavelength of light in an isotropic transparent material such as optical glass, and may also be a reverse dispersion rate. The larger the Abbe number, the smaller the dispersion, and conversely, the smaller the Abbe number, the larger the dispersion. Therefore, the "high Abbe number (or large)" in the lens means that the dispersion is small and clear, and is used in the same sense in the present invention.

In patent publication KR-92-1650, a small amount of dibutyltin dilauret is added as a catalyst to a mixture of methaxylene diisocyanate and pentaerthritol tetrakis (mercapto propionate) for 12 hours from 50 ° C to 110 ° C. Although a plastic lens was manufactured by heating, the lens also has excellent transparency, processability, and impact resistance, but has a problem in that light resistance is bad.

Patent publication KR92-6006 introduces a thiocarbamic acid S-alkyl ester plastic lens obtained by mixing and curing thiodimethyldiisocyanate and pentaerythritol tetrakis (3-mercaptopropionate). Transparency, weather resistance, refractive index, Abbe's number, etc. are excellent, but the heat resistance is low, there is a problem that the central portion of the lens is severely deformed in the heat curing process for coating the silicone compound to increase the scratch resistance on the plastic surface.

Patent publication KR-93-6918 discloses 2,5-bis (isocyanatomethyl) bicyclo [2, 2, 1] heptane and 2,6-bis (isocyanatomethyl) bisclo [2, 2, 1] A method of manufacturing a plastic lens by heating and curing a heptane and tetrakis (2-mercapto ethylthiomethyl) methane mixture has been introduced, but this also has a problem in that the central part of the lens is deformed during hard coating due to low thermal stability.

In addition, EP0606905A2 introduces a plastic lens made by adding acrylic acid to a tetrabromo bisphenol A type epoxy resin and a bisphenol A type epoxy resin and mixing styrene, divinylbenzene, benzyl methacrylate, and the like. However, these lenses have good heat resistance but have a low refractive index of 1.590 and an Abbe number of about 32.

In the patent publications KR96-13389 and 96-13390, a urethane bond or thiocarbamic acid characterized in that a polymerization is carried out by adding an internal mold release agent to a mixture of an active hydrogen compound containing an aromatic polyisocyanate, a polyol, and a polythiol containing sulfur atoms. Although a plastic lens having an S-alkyl ester bond is manufactured, it is also excellent in physical properties such as transparency, weather resistance, and workability, but has a problem in that a central portion of the lens is deformed during hard coating due to low thermal stability.

It is an object of the present invention to provide an optical raw material having excellent optical properties, that is, solvent resistance, transparency, light weight, heat resistance, particularly high refractive index, and high Abbe number.

To this end, the present invention provides a raw material for a plastic lens manufactured by mixing a material represented by the following Chemical Formula 1 and a material represented by the following Chemical Formula 2 and adding an organic or inorganic pigment, an ultraviolet absorber, and a release agent as necessary.

(Wherein R ₁ represents a hydrogen atom or a methyl group)

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(Wherein an integer of n = 1 to 3, an integer of m = 0 to 6, R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a hydrogen atom or a halogen atom)

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The resin composition for producing a plastic lens of the present invention is a component such as styrene monomer in 10 to 50% by weight of the material of component (1) represented by the following formula (1) and 10 to 60% by weight of the material of component (2) represented by the following formula (2): It is obtained by mixing 1-80 weight% of the substance of (3).

Component (1) is obtained by reacting thioprotanic acid with glycidyl (meth) acrylate at 90 to 100 ° C. for 10 to 24 hours under a triethylamine catalyst.

[Formula 1]

(Wherein R ₁ represents a hydrogen atom or a methyl group)

The content of component (1) based on the total mixture is preferably 10 to 50% by weight. When the content is 10% or less, the Abbe number of the lens is low, and when the content is 50% or more, there is a weak heat resistance.

Component (2) is obtained by reacting methacrylic acid or acrylic acid with a bisphenol a epoxy and a triethylamine catalyst, followed by addition of a polyhydric alcohol.

[Formula 2]

(Wherein n is an integer of 3 to 3, an integer is m = 0 to 6, R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a hydrogen atom or a halogen atom.)

When n is 4 or more and m is 7 or more in component (2), the manufactured plastic lens is weak in heat resistance, and thus a phenomenon in which the central portion of the lens is deformed during heat curing after hard coating occurs. The content of component (2) in the total mixture is preferably 10 to 60% by weight. When the content is 10% or less, the refractive index is low, and when the content is 60% or more, thermal stability and light resistance deteriorate rapidly.

Materials of component (3) include styrene monomers; Diisopropenylbenzene; Benzyl methacrylate; Methyl acrylate; Dibenzylmaleate; Dimethyl maleate; Ethyl acrylate; Methacrylate; Divinylbenzene; Glycidyl acrylate; n-propylacrylate; 2-hydroxy propyl acrylate; Cyclohexyl acrylate; One or more substances selected from the group consisting of phenyl acrylate and benzyl acrylate are used. To the mixture of components (1) and (2), 1 to 80% by weight of component (3) is added to suitably adjust the viscosity and reaction rate of the mixture. In one embodiment of the present invention, a composition for producing a plastic lens was obtained by mixing styrene monomer and diisopropenylbenzene as the material of component (3). The curing catalyst of the monomer mixture for producing a plastic lens of the present invention is diisopropylperoxydicarbonate, di-n-propyl oxycarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, t- Butylperoxy pivalate, 2,2-azobis (2,4-dimethylbareronitrile), t-butylperoxy-2-ethyl hexanoate, 1,1-bis (t-butylperoxy) -3 , 3,5-trimethylcyclohexane, t-butylperoxy neodecanoate and the like can be used.

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The monomer composition for plastic lens molding of the present invention is an optical raw material characterized by high refractive index, heat resistance, impact resistance, thermal stability, transparency, in particular high Abbe number.

Example

The present invention will be described in more detail with reference to the following examples. However, the present invention is not limited to the following examples.

Example 1

As component (1), 22.4 g of component (1) represented by the formula (3), 31.5 g of component (2) represented by the formula (4) as the component (2), 29 g of styrene monomer, 18 g of diisopropenylbenzene, and 2.2-azobis ( 0.1 g of 2.4-dimethyl vareronitrile) was mixed.

The mixture was poured into a glass mold and heated and cured at 46 ° C. for 10 hours, at 46 ° C. to 70 ° C. for 6 hours, at 70 ° C. to 100 ° C. for 3 hours, and at 100 ° C. for 2 hours. After the heat curing, cooled to 70 ℃ to remove the cured molding from the mold, and annealing at 100 ℃ for 2 hours to remove the residual stress to prepare a plastic lens. The manufactured lens was evaluated for physical properties in the following manner and the results are shown in Table 1.

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Refractive Index and Dispersion Value: It was measured using an Abe refractometer Atacosa 1T model.

Light transmittance: Measured using a spectrophotometer.

Impact resistance: 16.2 g of steel balls were dropped at a height of 127 cm in the center portion of the manufactured lens, and if the lens did not break, it was marked as ○, and if broken, it was marked with ×.

Specific gravity: It was measured by the underwater substitution method.

Solvent resistance: The plastic lens was immersed in acetone and methylene chloride for 2 hours, and if there was no crack or deformation of the plastic lens, it was indicated as ○, if present.

Heat resistance: After leaving the plastic lens in the oven for 2 hours at 130 ° C., if there was no deformation in the lens, ○, if there was a deformation, it was indicated by ×.

Light resistance: The plastic lens was exposed to Q-Pannel lad Products' Quv / spray model (5w) for 200 hours, and if there was no color change of the lens, it was marked as ○.

Thermal Stability: After leaving the plastic lens in an oven at 130 ° C. for 2 hours, if there was no change in color of the lens, it was marked as ○, if present.

Example 2

Except for using the material of Formula 5 as the component (1) to prepare a plastic lens in the same manner as in Example 1 and to measure the physical properties are shown in Table 1.

Example 3

Except for using the material of Formula 6 as the component (2) to prepare a plastic lens in the same manner as in Example 1 and to measure the physical properties are shown in Table 1.

Example 4

A plastic lens was manufactured in the same manner as in Example 1, except that 15 g of the material of Formula 3 was used as component (1) and 45 g of the material of formula (4) was used as component (2).

Example 5

Except for using divinylbenzene instead of diisopropenylbenzene, a plastic lens was prepared in the same manner as in Example 1, and the physical properties thereof were shown in Table 1 below.

Example 6

Except for using dibenzyl methacrylate instead of diisopropenylbenzene, a plastic lens was prepared in the same manner as in Example 2, and the physical properties thereof were shown in Table 1 below.

Example 7

Except for using dibenzyl maleate instead of diisopropenylbenzene, a plastic lens was prepared in the same manner as in Example 2, and the physical properties thereof were shown in Table 1 below.

Comparative Example 1

Except for using 35g of the material of Formula 7, 25g of the material of Formula 8, 40g of styrene monomer was prepared in the same manner as in Example 1 to measure the physical properties are shown in Table 1.

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Comparative Example 2

A plastic lens was manufactured in the same manner as in Comparative Example 1 except that 35 g of the material of Formula 7 and 25 g of the material of Formula 8 were mixed with 20 g of styrene monomer and 20 g of divinylbenzene, and the physical properties thereof were shown in Table 1 below.

As shown in the above examples and comparative examples, according to the method of the present invention, it is possible to obtain a plastic lens having a higher refractive index while having a higher refractive index than in the prior art.

Claims (2)

To 10 to 50% by weight of the substance of component (1) represented by the following formula (1) and 10 to 60% by weight of substance of the component (2) represented by the following formula (2), Styrene monomers; Diisopropenylbenzene; Benzyl methacrylate; Methyl acrylate; Dibenzylmaleate; Dimethyl maleate; Ethyl acrylate; Methacrylate; Divinylbenzene; Glycidyl acrylate; n-propylacrylate; 2-hydroxy propyl acrylate; Cyclohexyl acrylate; An optical resin composition obtained by mixing 1 to 80% by weight of component (3) containing at least one substance selected from the group consisting of phenyl acrylate and benzyl acrylate. [Formula 1] (Wherein R ₁ represents a hydrogen atom or a methyl group) [Formula 2] (Wherein an integer of n = 1 to 3 is represented, an integer is m = 0 to 6, R ₁ represents a hydrogen atom or a methyl group, R ₂ represents a hydrogen atom or a halogen atom) The method according to claim 1, The resin composition for optics characterized by mixing and using a styrene monomer and diisopropenylbenzene as said component (3).