KR20000058427A - The monomer wmposile for a oplical lens - Google Patents

Abstract

PURPOSE: A monomer composition for a plastic lens is provided, to increase the refractive index, to reduce the weight and to improve the impact resistance, the formability, the coloring property and the photostability. CONSTITUTION: The monomer composition comprises 40-90 wt% of the compound represented by the formula 1; 1-30 wt% of the compound represented by the formula 2; optionally 5-30 wt% of diethylene glycol bisaryl carbonate; and optionally 5-30 wt% of diaryl adipate. In the formula 1, R1 is an alkyl group of C1-C6; m is an integer of 1-15; and the ratio of the compounds whose m are 0, 1-3, 4-10 and 11, respectively, is 10-60 : 20-60 : 0-40 : 0-20 by weight. In the formula 2, R1 is an alkyl group of C1-C4; R2 is an alkyl group of C1-C3, or a phenyl group; and n is an integer of 1-3.

Description

Molding monomer for optics {The monomer wmposile for a oplical lens}

The present invention relates to a monomer composition for plastic lenses, and more particularly, to a plastic lens raw material and a plastic lens which are excellent in high refractive index, light weight, impact resistance, moldability, dyeing property, etc., and are excellent in light stability. Until recently, plastic lenses using polystyrene, polyethylene glycol bisaryl carbonate, polycarbonate, modified diaryl phthalate as raw materials have been introduced and used to overcome problems of glass lenses, that is, weak impact resistance and high specific gravity. The polystyrene and polycarbonate lenses have a high refractive index of 1.59, but are easily thermoplastic due to the thermoplastic resin, and have a low adhesive strength with the hard coat film.

In order to solve this problem, in EP06905A2, 15 to 50 parts by weight of styrene and 10 to 50 parts by weight of acrylic acid and bisphenol A-type epoxy resin reactant and 5 to 40 parts by weight of acrylic acid and bistrabrobobisphenol A type epoxy resin reactant are used. To solve the above problem by mixing 5 to 20 parts by weight of divinyl benzene, diaryl diphenate, vinyl toluene, and chlorostyrene, it was not able to solve the problem of weak thermal stability. Plastic lens made of polyethylene glycol bis (aryl carbonate) is excellent in light weight, moldability, dyeing properties, in particular, excellent impact resistance, there is a problem that the edge thickness of the lens is thick because the refractive index is low to 1.50. 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 plastic lens manufactured by increasing the refractive index to 1.55 was introduced. In Japanese Patent Laid-Open No. 53-7787, diaryl isophthalate and diethylene glycol bisaryl carbonate were introduced to 85 to 15. Although it succeeded in reducing the thickness of the lens by manufacturing a plastic lens by mixing, but the impact resistance of the lens is weak.

Japanese Patent Laid-Open No. 62-235901. 64-45412 and Japanese Patent Publication No. Hei 1-60494 also introduce copolymers of modified diaryl phthalate and dibenzyl fumarate, and polymers of diaryl phthalate and methyl acrylate, but these also have weak impact resistance.

Korean Patent Publication No. 96-013122 introduces a plastic lens manufactured by mixing and molding a modified diaryl phthalate, a modified modified ethylene glycol bis (arylcarbonate), and a dibenzyl maleate derivative.

Korean Laid-Open Patent Publication No. 1998-023955 introduces a plastic lens formed by mixing alcohol with an alcohol and reacting styrene or an acrylic monomer with the bisphenol A epoxy and acrylic acid.

Korean Patent Publication No. 1999-014549 introduces a plastic lens obtained by mixing and modifying a modified diaryl phthalate, zyloxyalkyl, and diethylene bisaryl carbonate. However, these plastic lenses are excellent in refractive index, formability, dyeing property, impact resistance, but there is a problem of poor light stability.

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

In the present invention as Formula 1

(Where -OR 'represents a divalent alcohol residue having 1-6 carbon atoms, m = integer 1-15, the weight ratio of m = o is 10-60%, and m = 1-3 is 20 to 60%, the weight ratio of m = 4-10 is 0 to 40%, the weight ratio of m = 11 or more indicates 0 to 20%) 40 to 90% by weight of the displayed component

By formula (2)

(Where R 'represents 1 to 4 carbon atoms, R2 represents 1 to 3 carbon atoms or a phenyl group. N = 1 to 3 integers.) Diaryl adipate or di 5-30 weight% of ethylene glycol bisaryl carbonates are mixed. Here it is proposed a plastic composition for an optical lens prepared by adding a small amount of inorganic pigment and ultraviolet absorber as needed.

The resin composition for producing a plastic lens of the present invention comprises diaryl adipate or diethylene glycol bis aryl carbonate in a component (1) represented by the formula (1) and the component (2) represented by the formula (2) in a specific blending ratio. It contains.

Component (1) was obtained by transesterification of diaryl phthalate and polyhydric alcohol, or dimethyl glycol mono aryl ester with dimethyl glycol mono aryl ester at 100 to 200 ° C for 5 to 14 hours.

(Where m represents an integer of 1 to 15, the weight ratio of m = 0 is 10 to 60%, the weight ratio of m = 4-10 is 0 to 40%, and the weight ratio of m = 11 or more is 0 to 20%)

If the weight ratio of m = 0 is lower than 10%, the viscosity becomes remarkably high, and the defect rate of the lens is high due to the polymerization imbalance as well as the lack of bubbles when the monomer mixture is injected into the glass mold. In addition, when the weight ratio of m = 11 or more is 20% or more, the viscosity may be too high and the above problems may occur. In addition, the weight% of the component (1) to the total mixture is preferably 40 to 90%, the refractive index is low when the weight% is 40% or less, there is a problem that the impact strength of the lens is lowered when 90% or more.

Component (2) was obtained by esterification of glycol ether to maleic acid, maleic anhydride or dimethyl maleic acid at 80 to 200 ° C. for 5 to 24 hours,

(Where R 'represents 1 to 4 carbon atoms, R2 represents a phenyl group having 1 to 3 carbon atoms, and n = 1 to 3 integers.) R' has desirable physical properties when the carbon number is 1 to 4, and the carbon number is 5 In the case of abnormality, the heat resistance of the plastic lens is low, so that the central portion changes during the hard coating of the lens. R2 also has good optical properties when the carbon number is 1 to 3, when the carbon number is 4 or more, the heat resistance of the lens is worse, there is a phenomenon that the properties to improve the light stability is also significantly reduced. When the weight% of the formula (2) in the total mixture is 1 to 40%, the effect of improving light stability is great. If more than 40% of the substance of Formula 2 is included, the solvent resistance and heat resistance of the lens are inferior.

5-30% by weight of diaryl adipate or diethylene glycol bisaniyl carbonate can be added to the materials of components (1) and (2) to improve the impact strength of plastic lenses. There is a problem that the refractive index is lowered. And in order to further improve the light stability and thermal stability, "hydroxy-4-methoxybenzophenone, 2-hydroxy-3,5-di-t-amylphenyl) benzotriazole, 2,4-bis (2 , 4-dimethylphenyl) -6- (2-hydroxy-4-n-octyloxyphenyl) -1,3,5-triazine, 2- (3-hydroxy-5-t ortylphenyl) benzotriazole , 2- [4- [2-hydroxy-3-dodecylpropyloxy] -4,6-bis (2,4-dimethylphenyl 0-1,3,5-triazine, 2- (2hydroxy- Benzotriazole-2-phenyl) -p-cresol, 2- (2-hydroxybenzotriazole-2-phenyl) -4,6-bis (1-methyl-1-phenylethyl) phenol, 2-2- One of hydroxy-3-butyl-5-methylphenyl) -5-chlorobenzotriazole was used. In addition, small amounts of inorganic pigments and ultraviolet absorbers may be added as necessary.

A small amount of blue and red pigment was added to clear the initial color of the lens, and a small amount of methanol, ethanol, butanol, pentanol, phenethyl alcohol, and benzyl alcohol were added.

The curing catalyst of the monomer mixture for plastic lens production of the present invention is "2,2-azobis (2,4-dimethylbareronateyl), diisopropyl peroxydicarbonate, di-n-propyloxycarbonate, Bis (4-t-butylcyclohexyl) peroxydicarboate, t-butylperoxy pivalgate, t-butylperoxy-2-ethylhexanoate, 1,1-bis (t-butylperoxy)- 3,3,5-trimethylcyclohexane, t-butylperoxy neodecanoate and the like may be used, but preferably 1-5 parts by weight of diisopropylperoxydicarbonate is used based on 100 parts by weight of the monomer composition. It is preferable.

The monomer composition for molding a plastic lens of the present invention is an optical raw material excellent in impact resistance, heat resistance, thermal stability, transparency, and in particular, optical stability.

Example

Hereinafter, examples and comparative examples of the present invention will be described in detail, but the present invention is not limited thereto.

Example 1

As component (1), 79 g of component (1) represented by the formula (1), 21 g of component (2) parts by weight represented by the formula (4) and 3,2 g of diisopropyl peroxycarbonate were mixed as the component (2).

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, and heated at 40 ° C. to 85 ° C. for 12 hours. , Heated at 85 ° C. for 2 hours. After heat curing, the cured molding was removed from the mold by cooling to 80 ° C., and annealing was performed at 120 ° C. for 2 hours to remove residual stress, thereby preparing an optical plastic material. The physical property evaluation of the manufactured optical plastic material was performed as follows, and the result is shown in Table 1.

Formula 1

Where -OR₁ represents OCH₂CH (CH₃), the weight ratio of m = 0 is 60%, the weight ratio of m = 1 is 20%, the weight ratio of m = 3 is 13%, and the weight ratio of m = 4 or more is 7%)

Formula 2

(Where R₁ represents 2 carbon atoms, R2 represents carbon number 1, and n = 1 represents an integer.)

Refractive index: It measured using the 1T model of Atacota Co., Ltd ..

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

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

Impact resistance: The lens was manufactured with a center thickness of 1.8 mm and a diameter of 80 mm (drop water 0.00) to drop a 68 gdml steel ball at a height of 127 cm, and marked 0 if the plastic lens was not broken, and X when broken.

Heat resistance: The lens was kept at 130 ° C. for 2 hours. If there was no change in deformation, cracking, yellowing, etc., 0 was displayed.

Solvent resistance: After immersing the plastic lens in acetone and methylene chloride for 2 hours, if there is no crack, deformation, etc. of the plastic lens, it is expressed as 0, if X.

Light stability: The plastic specimens were exposed to a Quv / spray model (5W) of Q-Pannel lad products for 200 hours and the YI values were measured.

Example 2

Curing and physical properties were measured in the same manner as in Example 1, except that 10 g of the component represented by the formula (2) and 10 g of the diaryl adipate were used for 90 g of the formula (1).

Example 3

Curing and physical properties were measured in the same manner as in Example 1 except that 80 g of the component of Formula 1 was used 10 g of diethylene glycol busanyl carbonate in 10 g of the component represented by the formula (2).

Example 4

It is the same as that of Example 1 except having the weight of 80g of the component of General formula (3) in 1, 20g of R <3> among the components of general formula (2).

Example 5

It is the same as that of Example 1 except having the weight of 80g of the component of Formula 3 to 20g of the carbon number of R 'which is a component of Formula (2).

Example 6

The same as that in Example 1 except that 20 g of R 2 having 3 carbon atoms in the component of Formula 2 is present in 80 g of the component of Formula 3.

Example 7

It is the same as that of Example 1 except that the carbon number of R2 is 4 g in the component of Formula 2, and it is 80 g weight of the component of Formula 3.

Example 8

It is the same as Example 1 except 20g of n = 2 among the components of Formula 2, and 80g of the component of Formula 3.

Example 9

As in Example 5, except that 80 g of the component of Formula 3 and 10 g of diethylene glycol bisaryl carbonate were used for 10 g of R 1 having 3 carbon atoms in the formula (2).

Example 10

Except for using diaryl adipate instead of diethylene glycol bisaryl carbonate in Example 9, and the same as in Example 9.

Comparative Example 1

Of formula 3

(m distribution: m = 0 is 65% by weight, m = 1 is 4% by weight, m = 3 is 1% by weight)

80 g of ingredients

It carried out like Example 1 except having used 20% of components.

Comparative Example 2

The same procedure as in Comparative Example 1 was carried out except that 10 g of dibenzyl malate was used for 70 g of the component of Formula 3 and 20 g of the component of Formula 6.

Comparative Example 3

The same procedure as in Comparative Example 1 was carried out except that 20 g of diethylene glycol bisaryl carbonate and 10 g of dimethyl maleate were used for 70 g of the formula (3).

Comparative Example 4

Dibutyl maleate was used in Comparative Example 3, except that dibutyl maleate was used.

Table 1

Refractive index Light transmittance Impact resistance Solvent resistance Heat resistance importance Y1 value (before exposure to optical specimen) Y1 value (explode the specimen after 200 hours of light) Example 1 1.55 92.0 ○ ○ ○ 1.28 4.1 4.6 Example 2 1.55 92.0 ○ ○ ○ 1.28 4.1 5.1 Example 3 1.55 92.0 ○ ○ ○ 1.28 4.2 5.0 Example 4 1.549 91.5 ○ ○ ○ 1.28 4.1 4.7 Example 5 1.549 91.8 ○ ○ △ 1.28 4.2 4.6 Example 6 1.549 91.5 ○ ○ ○ 1.28 4.1 4.7 Example 7 1.549 92.0 ○ ○ △ 1.28 4.1 4.6 Example 8 1.548 91.8 ○ ○ △ 1.28 4.2 4.7 Example 9 1.549 92.0 ○ ○ △ 1.28 4.2 5.2 Example 10 1.549 91.9 ○ ○ ○ 1.28 4.2 5.4 Example 1 1.549 92.0 ○ ○ ○ 1.28 4.2 7.2 Example 2 1.549 92.0 ○ ○ ○ 1.28 4.1 7.4 Example 3 1.549 91.8 ○ ○ ○ 1.28 4.1 7.1 Example 4 1.549 91.6 ○ ○ ○ 1.28 4.2 7.4

As shown in the above examples and comparative examples, according to the method of the present invention, a plastic lens having excellent light stability can be obtained as compared with the prior art.

Claims (3)

Formula (1) (Where -OR 'represents a divalent alcohol residue having 1 to 6 carbon atoms, m = integer 1 to 15, and a weight ratio of 10 to 60% for m = 0 and a weight ratio 20 to 60 for m = 1 to 3 %, the weight ratio of m = 4 to 10 is 0 to 40%, the weight ratio of m = 11 or more is 0 to 20%.) 40 to 90% of component (1) Formula (2) (Where R 'represents an alkyl group having 1 to 4 carbon atoms, R2 represents an alkyl group having 1 to 3 carbon atoms or a phenyl group and represents n = 1 to 3 integer) and contains 1 to 30% by weight of component (2) Molding type monomer composition for optics, characterized in that. The optical molding template monomer composition according to claim 1, further comprising 5 to 30% by weight of diethylene glycol bisaniyl carbonate. The optically castable monomer composition according to claim 1, wherein 5 to 30% by weight of the diaryl adipate is further contained.