KR100431434B1 - Monomer Composition for an Optical Lens - Google Patents

Abstract

The present invention relates to a monomer composition for plastic lenses, and provides a raw material for plastic lenses having excellent refractive index, light weight, impact resistance, heat resistance or dyeing property.

Such a composition of the present invention consists of diallyl ester oligomer, dialkylmaleate, diethylene glycol bisallylcarbonate and diallyl adipate.

Description

Monomer Composition for an Optical Lens

TECHNICAL FIELD The present invention relates to a monomer composition for plastic lenses, and more particularly, to a plastic lens material having excellent refractive index, light weight, impact resistance, moldability, dyeing property, and especially light stability, and a method of manufacturing the same.

In general, glass, which is a material used to manufacture an optical lens, has a disadvantage of poor impact resistance and relatively large weight, and thus, development of a new material for replacing glass has emerged as a major concern in the industry.

As a solution to this, plastic lenses manufactured using polystyrene, polyethylene glycol bisallyl carbonate, polycarbonate, and modified diallyl phthalate as raw materials have been introduced. However, although lenses made of polystyrene and polycarbonate exhibited excellent refractive indices of 1.59 or more, since the polystyrene and polycarbonate are thermoplastic resins, optical distortions are likely to occur during molding, and adhesion to a hard coat film is achieved. There was this low issue.

In order to solve the above problems, European Patent 06905 A2 discloses 15 to 50 parts by weight of styrene and 5 to 40 parts by weight of acrylic acid and bisphenol A type epoxy resin reactants and acrylic acid and bis-tetra-bromo bisphenol A type epoxy resin reactants 5 ~ 40 parts by weight, divinylbenzene, diallyl diphenate (vinate), vinyl toluene and chlorostyrene by mixing 5 to 20 parts by weight to solve the above problems, but the composition also had a problem of insufficient thermal stability .

In another example, a plastic lens made of polyethylene glycol bis (allyl carbonate) had excellent light weight, dyeability and impact resistance, but had a refractive index of up to 1.50, resulting in too thick the edge of the lens. Therefore, it is widely used in the lens of -3.00 or less, which has a low edge thickness, but it is avoided in the above frequency.

In order to solve the problem of the thickness of the plastic lens, a new plastic lens having a refractive index of 1.55 or more has been proposed.

Plastic lenses manufactured by 85% by weight of diallyl isophthalate and 15% by weight of diethylene glycol bisallylcarbonate of Japanese Patent Laid-Open No. 53-7787 have succeeded in reducing the thickness of the lens but still have a weak impact resistance. I had.

In addition, Japanese Patent Laid-Open Nos. 62-235901 and 64-45412 and No. Hei 1-60494 also provide plastic lenses and diallyl phthalates and methyl acrylates produced by copolymers of modified diallyl phthalate and dibenzyl fumarate. There is a plastic lens made of a copolymer made of, but these also have a problem of low impact resistance.

Korean Patent Publication No. 96-13122 introduces a plastic lens prepared by molding a mixture of modified ethylene glycol (allylcarbonate) and dibenzyl maleate derivative, and Korean Patent Publication No. 98-23955 describes bisphenol A type epoxy and Introducing a plastic lens prepared by dissolving acrylic acid in alcohol, and adding styrene or acrylic monomer and molding the resultant, Korean Patent Laid-Open Publication No. 99-14549 discloses modified diallyl phthalate, zyloxyalkyl and diethylene Plastic lenses obtained by mixing and molding bisallyl carbonate are introduced. However, these plastic lenses have excellent refractive index, moldability, dyeing property and impact resistance, but have poor light stability.

Accordingly, an object of the present invention is to provide an optical lens having excellent optical properties, that is, high refractive index, thermal stability, solvent resistance, light weight, transparency, as well as excellent light stability.

In order to achieve the above object, the present invention is a diallyl adipate or diethylene glycol bisallylcarbonate in a mixture of 40 to 90% by weight of the polymer represented by the following formula (1), 1 to 30% by weight of the polymer represented by the formula (2) To 5 to 30% by weight, to provide a plastic composition for an optical lens comprising a small amount of inorganic pigment and ultraviolet absorber as needed.

Here, examples of Formula 1 are as follows, but are not limited thereto.

Hereinafter, Chemical Formula 1 is referred to as "first component."

[Formula 1]

Here, -OR ₁ represents a divalent alcohol residue having 1 to 6 carbon atoms, m is an integer of 0 to 15, the weight ratio of m = 0 is 10 to 60%, the weight ratio of m = 1 to 3 is 20 to The weight ratio of 60%, m = 4-10 is 0-40%, and the weight ratio of m≥11 is 0-20%.

In addition, examples of the formula (2) are as follows, but are not limited thereto.

Hereinafter, Chemical Formula 2 is referred to as "second component".

[Formula 2]

R ₁ is alkylene having 1 to 4 carbon atoms; R ₂ is an alkyl group having 1 to 3 carbon atoms; n represents the integer of 1-3.

As described above, the resin composition for producing a plastic lens of the present invention is obtained by blending diallyl adipate or diethylene glycol bisallylcarbonate in a specific compounding ratio in the first component and the second component.

The first component is obtained by transesterification of diallyl phthalate and polyhydric alcohol or transesterification of dimethyl phthalate and ethylene glycol monoallyl ester, wherein the reaction is carried out at a temperature of 100 to 200 ° C. and a reaction condition of 5 to 14 hours. Is done in

<First component>

Here, -OR ₁ represents a divalent alcohol residue having 1 to 6 carbon atoms, m is an integer of 0 to 15, the weight ratio of m = 0 is 10 to 60%, the weight ratio of m = 1 to 3 is 20 to The weight ratio of 60%, m = 4-10 is 0-40%, and the weight ratio of m≥11 is 0-20%.

If the weight ratio of m = 0 is less than 10%, the viscosity is remarkably high, and not only the imbalance of polymerization but also bubbles are not easily released when the monomer mixture is injected into the glass mold, so that the defective rate of the lens is high. In addition, when m≥11 is 20% or more, the viscosity is too high, and similar problems occur as above.

Moreover, it is preferable that the weight ratio of the 1st component with respect to the whole mixture is 40 to 90 weight%. This is because, if the weight ratio of the first component is less than 40% by weight, the refractive index is considerably lowered, and if it is greater than 90% by weight, the impact resistance is considerably poor.

The second component was obtained by esterifying glycol ether to maleic acid, maleic anhydride or dimethyl maleic acid at 80 to 200 ° C for 5 to 14 hours.

<Second component>

R ₁ is alkylene having 1 to 4 carbon atoms; R ₂ is an alkyl group having 1 to 3 carbon atoms; n represents the integer of 1-3.

If R ₁ ≥ C _5, the heat resistance of the plastic lens is lowered, and deformation of the center of the lens occurs during hard coating. Moreover, when R <_2> C <_4> , the heat resistance of a plastic lens will fall and light stability will worsen remarkably.

Therefore, in order to have excellent optical properties, it is important that R ₁ is C ₁ -C ₄ and R ₂ is C ₁ -C ₃ .

The second component in the total composition should be used 1 to 40% by weight in order to maximize the light stability effect. It is because solvent resistance and heat resistance worsen when it is 40 weight% or more.

In addition to the first component and the second component, 5 to 30% by weight of diallyl adipate or diethylene glycol bisallylcarbonate is added to improve impact resistance of the plastic lens.

Here, when 30% by weight or more of diallyl adipate or diethylene glycol bisallylcarbonate is added, the refractive index of the lens is lowered.

In the present invention, hydroxy-4-methoxybenzophenone, 2-hydroxy-3,5-di-t-amylphenyl benzotriazole, 2,4- to prepare a plastic lens having improved photostability and thermal stability Bis (2,4-dimethyl phenyl) -6- (2-hydroxy-4-n-octyloxyphenyl-1,3,5-triazine), 2- (3-hydroxy-5-t-octylphenyl ) Benzotriazole, 2- [4- (2-hydroxy-3-dodecyl propyloxy) -4,6-bis (2,4-dimethylphenyl-o-1,3,5-triazine)], 2- (2-hydroxy-benzotriazole-2-phenyl) -p-cresol, 2- (2-hydroxy benzotriazole-2-phenyl) -4,6-bis (1-methyl-1-phenyl An additive selected from the group consisting of ethyl) phenol and 2-2-hydroxy-3-butyl-5-methylphenyl) -5-chlorobenzotriazole is added.

Optionally, small amounts of inorganic pigments or ultraviolet adsorbents can be added.

In the present invention, small amounts of blue and red pigments are added to clear the initial color of the lens, and some alcohols, such as methanol, ethanol, butanol, pentanol, 2-phenylethanol or benzyl alcohol, are added.

The curing catalyst of the monomer mixture for producing a plastic lens of the present invention is 2,2-azobis (2,4-dimethylbutyronitrile), di-isopropylperoxydicarbonate, di-n-propyloxycarbonate, bis (4-t -Butylchlorohexyl) peroxydicarbonate, t-butylperoxy pivalate and t-butyl peroxy neodecanoate may be selected from the group consisting of, but preferably di-isopropyl peroxydicarbonate monomer composition It is preferable to use 1-5 weight part with respect to 100 weight part.

Accordingly, the present invention provides a monomer composition for producing a plastic lens excellent in improved impact resistance, heat resistance, thermal stability, transparency and especially light stability.

Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following examples are intended to illustrate the invention but not to limit the invention.

Example 1

79 g of the first component, 21 g of the second component, and 3.2 g of di-isopropylperoxycarbonate were mixed. The mixture was poured into a mold consisting of two glass plates and an ethylene-vinylacetate copolymer, heated at 35 ° C to 40 ° C for 3 hours, heated at 40 ° C to 85 ° C for 12 hours, and then 85 Heat at C for 2 h.

After heat curing, it was cooled at 80 ° C., the cured molding was taken out of the mold, and annealing was carried out at 120 ° C. for 2 hours to remove residual stress to prepare an optical plastic material. The physical property evaluation of the manufactured material was performed as follows, and the result is shown in Table 1. (See Table 1)

<First component>

Here, -OR ₁ represents a divalent alcohol residue having 3 carbon atoms, the weight ratio of m = 0 is 60%, the weight ratio of m = 1 is 20%, and the weight ratio of m = 3 is 13%, m = 4 The weight ratio of the above is 7%.

<Second component>

In the above, R ₁ represents a hydrocarbon having 2 carbon atoms, that is, ethylene, and R ₂ represents a hydrocarbon having 1 carbon atoms, ie, methyl, and n = 1.

Physical property test

1. Refractive index: Measured using an Atacota Co 1T model.

2. Light transmittance and UV blocking rate were measured using a spectrophotometer.

3. Specific gravity: The ratio of the weight and volume of the plastic lens was measured using the underwater substitution method.

4. Impact resistance: A 68g steel ball was dropped at a height of 127cm to a plastic lens with a thickness of 1.8 mm and a diameter of 80 mm (0.00 tap), and if the lens was not broken, it was marked as "O". If broken, it is indicated by "X".

5. Heat resistance: When the plastic lens is kept at 130 ℃ for 2 hours, when the lens shows signs of deformation, cracks on the lens or turns yellow, it is marked with "X" and there is only slight change. In the case of " △ ", no change was indicated by " O ".

6. Solvent resistance: When the plastic lens is immersed in acetone and methylene chloride for 2 hours, when the lens is deformed or cracked, it is marked with "X", otherwise it is marked with "O".

7. Light stability: The plastic lens specimen was exposed to Qv / spray model (5W) of Q-Panel lad products Co., Ltd. for 200 hours, and then YI (Yeollw Index; yellowness) was measured.

Example 2

An optical lens material was prepared in the same manner as in Example 1 except that 10 g of diallyl adipate was used for 90 g of the first component (see Table 1).

Example 3

An optical lens material was prepared in the same manner as in Example 1 except that 80 g of the first component, 10 g of the second component, and 10 g of diethylene glycol bisallylcarbonate were added thereto (see Table 1).

Example 4

An optical lens material was prepared in the same manner as in Example 1 except that 80 g of the first component and 20 g of the second component having R ₁ of C ₃ were used (see Table 1).

Example 5

An optical lens material was prepared in the same manner as in Example 1 except that 80 g of the first component and 20 g of the second component having R ₁ of C ₄ were used (see Table 1).

Example 6

An optical lens material was prepared in the same manner as in Example 1 except that 80 g of the first component and 20 g of the second component having R ₂ of C ₃ were used (see Table 1).

Example 7

An optical lens material was prepared in the same manner as in Example 1 except that 80 g of the first component and 20 g of the second component having R ₂ of C ₄ were used (see Table 1).

Example 8

An optical lens material was prepared in the same manner as in Example 1 except that 80 g of the first component and 20 g of the second component having n of 2 were used (see Table 1).

Example 9

An optical lens material was prepared in the same manner as in Example 5 except that 80 g of the first component, 20 g of the second component having R ₁ of C ₃ , and 10 g of diethylene glycol bisallyl carbonate were used (see Table 1). .

Example 10

An optical lens material was prepared in the same manner as in Example 9 except that diaryl adipate was used instead of diethylene glycol bisallyl carbonate (see Table 1).

Comparative Example 1

An optical lens material was prepared in the same manner as in Example 1 except that 80 g of the first component and 20 g of the third component were used (see Table 1).

<First ingredient>

In the above, R ₁ is C ₂ H ₄ , m is m = 65% by weight, m = 1 is 30% by weight, m = 3 is 5% by weight.

<Third component>

In the above distribution of n, n = 1 is 52% by weight, n = 2 is 36% by weight, n = 3 is 9% by weight, and n = 4 is 3% by weight.

Comparative Example 2

An optical lens material was prepared in the same manner as in Comparative Example 1, except that 70 g of the first component, 20 g of the third component, and 10 g of dibenzyl maleate were used in Comparative Example 1 (see Table 1).

Comparative Example 3

An optical lens material was prepared by performing the same procedure as in Comparative Example 1 using 60 g of the first component of Comparative Example 1, 20 g of diethylene glycol bisallylcarbonate and 20 g of dimethyl maleate (see Table 1).

Comparative Example 4

An optical lens material was prepared in the same manner as in Comparative Example 3 except that dibutyl maleate was used instead of dimethyl maleate (see Table 1).

TABLE 1

Refractive index Light transmittance Impact resistance Solvent resistance Heat resistance importance YI (before exposure to light) YI (after 200 hours of light exposure) Example 1 1.55 92.0 O O O 1.28 4.1 4.6 Example 2 1.55 92.0 O O O 1.28 4.1 5.1 Example 3 1.55 92.0 O O O 1.28 4.2 5.1 Example 4 1.549 91.5 O O O 1.28 4.1 4.7 Example 5 1.549 91.8 O O △ 1.28 4.2 4.6 Example 6 1.549 91.5 O O O 1.28 4.1 4.7 Example 7 1.549 92.0 O O △ 1.28 4.1 4.6 Example 8 1.548 91.8 O O △ 1.28 4.2 4.7 Example 9 1.549 92.0 O O △ 1.28 4.2 5.2 Example 10 1.549 91.9 O O O 1.28 4.2 5.4 Comparative Example 1 1.549 92.0 O O O 1.28 4.2 7.2 Comparative Example 2 1.549 92.0 O O O 1.28 4.1 7.4 Comparative Example 3 1.549 91.8 O O O 1.28 4.1 7.1 Comparative Example 4 1.549 91.6 O O O 1.28 4.2 7.4

As described above, the plastic lens of the present invention has particularly excellent light stability and impact resistance.

Claims (3)

40 to 90% by weight of the modified diallyl phthalate component 1 represented by Formula 1 [Formula 1] (Where -OR _{1 is a} divalent alcohol residue having 1 to 6 carbon atoms; m is an integer of 0 to 15, the weight ratio of m = 0 is 10 to 60%, and the weight ratio of m = 1 to 3 is 20 to 60 %, the weight ratio of m = 4-10 is 0-40%, and the weight ratio of m≥11 is 0-20%.); To 1 to 30% by weight of the component 2 represented by the formula (2) [Formula 2] (Wherein R ₁ is alkylene having 1 to 4 carbon atoms; R ₂ is an alkyl group having 1 to 3 carbon atoms; n is an integer of 1 to 3.) A monomer composition for an optical lens obtained by mixing. The method of claim 1, In addition to the said composition, the monomer composition for optical lenses containing 5-30 weight% of diethylene glycol bisallylcarbonate further. The method of claim 1, In addition to the said composition, the monomer composition for optical lenses containing 5-30 weight% of diallyl adipate further.