JP3354066B2 - Eyeglass lens - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a spectacle lens which is excellent in impact resistance and transparency and has high ultraviolet absorbing ability, particularly high ultraviolet absorbing ability at a specific wavelength. More specifically, the present invention relates to a spectacle lens containing a polycarbonate resin as a resin component, hardly yellowing, and excellent in moldability.

[0002]

2. Description of the Related Art Polycarbonate resins have high refractive index and excellent characteristics of transparency and impact resistance, and have recently been receiving attention as materials for lenses, particularly as materials for eyeglass lenses. The spectacle lenses made of polycarbonate resin are thinner, lighter, and have significantly higher impact strength than conventional glass lenses and cast-polymerized plastic lenses (hereinafter referred to as cast lenses), and are therefore safe and highly functional.
As spectacle lenses, they have been used for eyesight correction lenses, sunglasses, protective glasses, and the like. recently,
There is a strong demand for spectacle lenses to have ultraviolet absorbing ability and to protect eyes from harmful ultraviolet rays.For example, in cast lenses and glass lenses, a coating layer having ultraviolet absorbing ability is provided on the lens surface, To meet your needs.
However, such a coating method is disadvantageous in that it is expensive and the lens itself becomes slightly yellow. In addition, an ultraviolet absorber is added to the cast lens when polymerizing. However, such a method has disadvantages such as inhibition of polymerizability and remarkable yellowing of the lens itself.

[0003] On the other hand, in a polycarbonate resin spectacle lens, the polycarbonate resin itself has an ultraviolet absorbing ability, and is thermoplastic. Since an absorber can be contained, an ultraviolet absorber having a longer wavelength can be added. However, the conventional polycarbonate resin has a limit of absorbing ultraviolet rays up to 375 nm, and if an attempt is made to absorb a longer wavelength than this, the content of the ultraviolet absorber must be added 2 to 10 times the usual amount. No. In general, since a UV absorber is sublimable, if a large amount of the UV absorber is added, during injection molding of a polycarbonate resin, the UV absorber will sublimate and contaminate the mirror mold, significantly impairing the appearance of the obtained lens. become.

JP-B-6-35141 and JP-B-6-41162 disclose that a polycarbonate resin is added with 0.1 to 20 parts by weight of an oligomer type ultraviolet absorber which is hardly sublimated, and is used for preparing a multilayer laminated sheet or film. A method of forming the surface layer at the time of extrusion molding is exemplified.
However, its purpose is to impart weatherability to the sheet,
Not for optical purposes. Some types of UV absorbers have the ability to absorb longer wavelength UV light. However, the addition of these UV absorbers for long wavelength absorption causes the polycarbonate resin to turn remarkably yellow. It is necessary to add an agent to eliminate the yellow color.
However, in such a method, transparency was hindered in lens applications due to a large amount of bluing agent, and the luminous transmittance was reduced, so that only a very dull lens could be provided.
Furthermore, Japanese Patent Application Laid-Open No. 7-92301 proposes a plastic lens that blocks the transmission of ultraviolet light and near infrared light by adding an ultraviolet absorber and an infrared absorber. However, the lenses obtained by this method have insufficient transparency. Therefore, for a polycarbonate resin spectacle lens, completely absorbing ultraviolet light of 380 nm or less and high transparency were considered to be contradictory characteristics.

On the other hand, JP-A-62-146951 discloses that an alkylidenebis (benzotriazolylphenol) compound represented by a specific structural formula is contained in an amount of 0.001 to 5 parts by weight based on 100 parts by weight of a polycarbonate resin. Thus, a polycarbonate resin composition having improved light resistance is described. This publication discloses that the above five specific compounds are each added to a polycarbonate resin by 0.30.
The results are shown in which a test piece with weight% added was prepared, irradiated with ultraviolet light from a high-pressure mercury lamp, the yellowness of the test piece was measured, and the change (ΔYI) was measured. The results merely show that the addition of the specific compound reduced the yellowness change.

Further, JP-A-4-292661 discloses a transparent thermoplastic resin 1 containing a polycarbonate resin.
0.0 parts by weight of an ultraviolet absorbent which has an absorption maximum at a wavelength of 280 to 360 nm and has no absorption at a wavelength of 400 nm is 0.0.
A resin composition containing 1 to 0.15 parts by weight is described. This resin composition has a silver salt film having a wavelength of 400 nm.
Because of the presence of a sensitivity peak, the lens was developed as a camera lens having a light transmittance at a wavelength of 400 nm of 80% or more.

[0007]

SUMMARY OF THE INVENTION It is a first object of the present invention to provide a spectacle lens made of a polycarbonate resin which has excellent impact resistance and transparency and can almost completely cut off ultraviolet rays having a specific wavelength. . A second object of the present invention is to provide an eyeglass lens made of a composition that hardly causes yellowing due to ultraviolet light and does not cause contamination of a mirror surface of a mold by sublimation of an ultraviolet absorbent during molding.
A third object of the present invention is to provide a spectacle lens that does not substantially transmit a wavelength of 380 nm and has a high luminous transmittance.

The present inventor has conducted intensive studies on the ultraviolet absorber used for the polycarbonate resin in order to achieve the above-mentioned object. As a result, the two types of ultraviolet absorbers having specific absorption maximums are combined in a specific amount and a specific ratio. If you use
The present inventors have found that it is possible to completely absorb ultraviolet light having a wavelength of 380 nm without impairing the moldability and without impairing the transparency of the lens, and arrived at the present invention.

[0009]

According to the present invention, (1) 100 parts by weight of a polycarbonate resin, (2)
When measured in a chloroform solution, the wavelength is 300 to 34.
UV absorber having an absorption maximum at 5 nm (A) 0.05
(3) a resin composition consisting essentially of 0.01 to 0.3 parts by weight of an ultraviolet absorber (B) having an absorption maximum at a wavelength of 346 to 400 nm when measured in a chloroform solution. A more formed spectacle lens is provided.

In the resin composition for forming a spectacle lens of the present invention, the two types of ultraviolet absorbers, the ultraviolet absorber (A) and the ultraviolet absorber (B), are used in combination and in the above amounts. However, the ratio of the ultraviolet absorber (A) and the ultraviolet absorber (B) is
Advantageously, it is in the range from 0.05 to 4, expressed as (B) / (A) (weight ratio). Hereinafter, the spectacle lens of the present invention will be described in more detail.

The polycarbonate resin used in the present invention comprises:
An aromatic polycarbonate resin obtained by reacting a dihydric phenol with a carbonate precursor. Specific examples of the dihydric phenol used here include, for example, 2,2-bis (4-hydroxyphenyl) propane (commonly known as bisphenol A), bis (4-hydroxyphenyl) methane,
1,1-bis (4-hydroxyphenyl) ethane, 2,2
-Bis (4-hydroxyphenyl) butane, 2,2-bis (4-hydroxyphenyl) octane, 2,2-bis (4-hydroxyphenyl) phenylmethane, 2,2-
Bis (4-hydroxy-3-methylphenyl) propane, 1,1-bis (4-hydroxy-3-tert-butylphenyl) propane, 2,2-bis (4-hydroxy-3-bromophenyl) propane, , 2-bis (4
-Hydroxy-3,5-dibromophenyl) propane,
Bis (hydroxyaryl) alkanes such as 2,2-bis (4-hydroxy-3,5-dichlorophenyl) propane, 1,1-bis (hydroxyphenyl) cyclopentane, 1,1-bis (hydroxyphenyl) cyclohexane, etc. Bis (hydroxyphenyl) cycloalkanes of
Dihydroxyaryl ethers such as 4,4'-dihydroxydiphenyl ether, 4,4'-dihydroxy-3,3'-dimethyldiphenyl ether, 4,4'-dihydroxydiphenyl sulfide, 4,4'-dihydroxy-3,
Dihydroxydiaryl sulfides such as 3'-dimethyldiphenyl sulfide, 4,4'-dihydroxydiphenyl sulfoxide, and dihydroxydiaryl sulfoxides such as 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfoxide, 4,4'-dihydroxy And dihydroxydiarylsulfones such as diphenylsulfone and 4,4′-dihydroxy-3,3′-dimethyldiphenylsulfone. These dihydric phenols may be used alone or in combination of two or more.

It is preferable that 2,2-bis (4-hydroxyphenyl) propane (bisphenol A) be the main dihydric phenol component among the dihydric phenols.
In particular, 70 mol% or more, especially 8
Those in which 0 mol% or more is bisphenol A are preferred. Most preferred are aromatic polycarbonate resins wherein the dihydric phenol component is substantially bisphenol A.

The basic means for producing a polycarbonate resin will be briefly described. In the solution method using phosgene as a carbonate precursor, a reaction between a dihydric phenol component and phosgene is usually performed in the presence of an acid binder and an organic solvent. As the acid binder, for example, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide or an amine compound such as pyridine is used. As the organic solvent, for example, halogenated hydrocarbons such as methylene chloride and chlorobenzene are used. Further, a catalyst such as a tertiary amine or a quaternary ammonium salt can be used to promote the reaction, and phenol or p-ter may be used as a molecular weight regulator.
It is desirable to use a terminal terminator such as an alkyl-substituted phenol such as t-butylphenol. The reaction temperature is usually 0 to 40 ° C, the reaction time is several minutes to 5 hours, and the pH during the reaction.
Is preferably maintained at 10 or more.

In the transesterification method (melting method) using a carbonic acid diester as a carbonate precursor, a predetermined ratio of a dihydric phenol component and a carbonic acid diester are stirred while heating in the presence of an inert gas to form an alcohol or phenol formed. It is a method of distilling off kinds. The reaction temperature varies depending on the boiling point of the produced alcohol or phenol, and is usually in the range of 120 to 300 ° C. The reaction is carried out under reduced pressure from the beginning while distilling off alcohol or phenols produced. Further, a normal transesterification catalyst can be used to promote the reaction. Examples of the carbonic acid diester used in this transesterification reaction include diphenyl carbonate, dinaphthyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate and the like, and diphenyl carbonate is particularly preferred.

The molecular weight of the polycarbonate resin used in the present invention is 17,000 to 30,0, expressed as a viscosity average molecular weight.
00 is preferable, and 20,000 to 26,000 is particularly preferable. Eyeglass lenses are precision molded, it is important to accurately transfer the mirror surface of the mold to give a specified curvature and frequency, and a low-viscosity resin with good melt fluidity is desirable, but if the viscosity is too low The impact strength characteristic of polycarbonate resin cannot be maintained. The viscosity average molecular weight (M) is determined by using an Ostwald viscometer to determine the intrinsic viscosity [η] of a solution measured at 20 ° C. using methylene chloride as a solvent, and the Schnell viscosity formula [η] = 1. It is determined from 23 × 10 ⁻⁴ M ^0.83 .

In the resin composition of the present invention, two types of ultraviolet absorbers having different wavelength absorption characteristics are blended in the polycarbonate resin. One is wavelength 300-34
An ultraviolet absorber (A) having an absorption maximum in the range of 5 nm, and the other is an ultraviolet absorber (B) having an absorption maximum in the wavelength range of 346 to 400 nm. The absorption maximum of these two types of UV absorbers is 10
Concentration 10m with chloroform solution using mm quartz cell
2 is an absorption spectrum measured in g / liter.

When these two types of ultraviolet absorbers are used alone, the absorption of ultraviolet light having a wavelength of 380 nm is insufficient, or when added in such a large amount that absorption is sufficient, the ultraviolet absorption at the time of molding is increased. The agent sublimates, causing an increase in haze of the lens and a decrease in hue.

According to the present invention, by using the above two specific types of ultraviolet absorbents (A) and (B) in combination, even if the respective amounts are relatively small, the ultraviolet light of 380 nm is used. Can be almost completely absorbed, the luminous transmittance is maintained at 87% or more, and the hue of the lens is also good. In addition, there is an advantage that the rate of change to yellow by ultraviolet rays is extremely small.

The ultraviolet absorber (A) is 300 to 345 n
m has an absorption maximum, and examples thereof include 2-hydroxy-4-methoxybenzophenone and 2-hydroxy-4-methoxybenzophenone.
Hydroxy-4-n-octoxybenzophenone, 2-
Benzophenone ultraviolet absorbers represented by hydroxy-4-methoxy-2'-carboxybenzophenone and 2,4-dihydroxybenzophenone; and, for example, 2- (2'-hydroxy-5'-methylphenyl) benzotriazole, 2- [ 2-hydroxy-3- (3,4,
5,6-tetrahydrophthalimidomethyl) -5-methylphenyl] benzotriazole, 2- (2-hydroxy-3,5-di-tert-butylphenyl) benzotriazole and 2- (2'-hydroxy-5'-ter
Examples thereof include benzotriazole-based ultraviolet absorbers represented by (t-octylphenyl) benzotriazole, and these may be used alone or in combination of two or more.

Among these ultraviolet absorbers (A), benzotriazole-based ultraviolet absorbers are preferred.
(2′-hydroxy-5′-methylphenyl) benzotriazole and 2- (2′-hydroxy-5′-tert)
-Octylphenyl) benzotriazole is particularly preferred.

These ultraviolet absorbers (A) are added in an amount of 0.05 to 0.5 parts by weight per 100 parts by weight of the polycarbonate resin. If the amount is less than 0.05 part by weight, the ultraviolet ray absorbing performance is insufficient. Even if the amount exceeds 0.5 part by weight, the ultraviolet ray absorbing ability is no longer improved. And the hue deteriorates remarkably. A particularly preferred amount is 0.1 to 0.35 parts by weight.

Wavelength 346 used in combination with ultraviolet absorber (A)
Examples of the ultraviolet absorber (B) having an absorption maximum at ~ 400 nm include a benzophenone-based ultraviolet absorber represented by, for example, 2,2'-dihydroxy-4-methoxybenzophenone; for example, 2- (3-tert-butyl-5- Methyl-
2-hydroxyphenyl) -5-chlorobenzotriazole, 2- (3,5-di-tert-butyl-2-hydroxyphenyl) -5-chlorobenzotriazole,
2,2'-methylenebis [4- (1,1,3,3-tetramethylbutyl) -6- (2H-benzotriazole-2-
Yl) phenol], 2- [2-hydroxy-3,5-
Bis (α, α-dimethylbenzyl) phenyl] -2H-
Benzotriazole and 2- (3,5-di-tert.
Examples thereof include benzotriazole ultraviolet absorbers represented by (-amyl-2-hydroxyphenyl) benzotriazole, and these may be used alone or in combination of two or more.

Among these ultraviolet absorbers (B), benzotriazole-based ultraviolet absorbers are preferred.
(3-tert-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole, 2,2′-
Methylenebis [4- (1,1,3,3-tetramethylbutyl) -6- (2H-benzotriazol) -2-yl)
Phenol] and 2- [2-hydroxy-3,5-bis (α, α-dimethylbenzyl) phenyl] -2H-benzotriazole are particularly preferred.

These ultraviolet absorbers (B) are added in an amount of 0.01 to 0.3 parts by weight per 100 parts by weight of the polycarbonate resin. If the amount is less than 0.01 part by weight, the ultraviolet absorbing performance is insufficient. If the amount exceeds 0.3 part by weight, depending on the ultraviolet absorbent (B), the hue may be remarkably deteriorated, resulting in a dull lens. More preferred is 0.015
To 0.27 parts by weight, particularly preferably 0.02 to 0.2 parts by weight.
25 parts by weight. Further, for the ultraviolet absorber (A) and the ultraviolet absorber (B), the compounding ratio (weight) R represented by the following formula R = (B) / (A) is set in the range of 0.05 to 4. It is desirable to do. When the compounding ratio R is less than 0.05, the ultraviolet absorbing performance is insufficient, and when the compounding ratio R exceeds 4, the hue is remarkably deteriorated, which is not suitable for practical use. Particularly preferred is 0.06-3.

The timing and method of blending the ultraviolet absorbent (A) and the ultraviolet absorbent (B) are not particularly limited, and may be during or after the polymerization of the polycarbonate resin. With any mixer, such as a tumbler,
They can be mixed and melt-kneaded by a ribbon blender, high-speed mixer, or the like. The ultraviolet absorber (A) and the ultraviolet absorber (B) may be added simultaneously or in any order.

A releasing agent can be added to the polycarbonate resin composition of the present invention, and this gives favorable results. Saturated fatty acid esters are generally used as the release agent, for example, monoglycerides such as stearic acid monoglyceride, lower fatty acid esters such as stearic acid stearate, higher fatty acid esters such as sebacic acid behenate, pentaerythritol tetrastearate and the like. Erythritol esters are used in an amount of 0.03 to 1 part by weight per 100 parts by weight of the polycarbonate resin.
If necessary, a phosphite-based heat stabilizer may be added in an amount of 0.001 to 0.1 part by weight per 100 parts by weight of the polycarbonate resin. Examples of the phosphite-based heat stabilizer include tris (nonylphenyl) phosphite, triphenylphosphite, tris (2,4-di-tert-butylphenyl) phosphite, and tetrakis (2,4-di-tert-butyl). Phenyl) -4,4'-biphenylenediphosphonite, bis- (2,6-di-tert-butyl-4-methylphenyl) pentaerythritol-di-
Phosphite, bis (2,4-di-tert-butylphenyl) pentaerythritol-di-phosphite, tris (ethylphenyl) phosphite, tris (butylphenyl) phosphite and tris (hydroxyphenyl) phosphite are preferred. , Tris (nonylphenyl) phosphite and tetrakis (2,4-di-t
(tert-butylphenyl) -4,4'-biphenylenediphosphonite is particularly preferred.

When molded into a spectacle lens, the polycarbonate resin composition of the present invention may contain a bluing agent for canceling the yellow tint of the lens based on the polycarbonate resin or the ultraviolet absorber. As the bluing agent, any one can be used without any particular difficulty as long as it is used for a polycarbonate resin. Generally, anthraquinone dyes are easily available and preferred.

Specific blueing agents include, for example, Solvent Violet 13 [CA. No
(Color index No.) 60725; Trade name “Macrolex Violet B” manufactured by Bayer, “Diaresin Blue G” manufactured by Mitsubishi Chemical Corporation, “Sumiplast Violet B” manufactured by Sumitomo Chemical Co., Ltd.], generic name S
solvent Violet 31 [CA. No 682
10; trade name “Diaresin Violet D” manufactured by Mitsubishi Chemical Corporation], generic name Solvent Violet 3
3 [CA. No. 60725; Trade name: Mitsubishi Chemical Corporation
"Diaresin Blue J"], generic name Solvent
Blue 94 [CA. No 61500; Trade name “Diaresin Blue N” manufactured by Mitsubishi Chemical Corporation], generic name S
solventViolet36 [CA. No 6821
0; brand name “Macrolex Violet 3R” manufactured by Bayer AG], generic name Solvent Blue 97 [brand name “Macrolex Blue RR” manufactured by Bayer AG] and generic name Solvent Blue 45 [CA. No 6
1110; Trade name "Tetazole Blue R" manufactured by Sando Co., Ltd.
LS "] is a representative example. These bluing agents are usually blended in the polycarbonate resin at a concentration of 0.3 to 1.2 ppm. If too much bluing agent is added, the absorption of the bluing agent becomes strong, and the luminous transmittance is reduced, resulting in a dull lens. Especially in the case of eyesight correction eyeglass lenses, since there is a large change in the thickness of the lens with a thick part and a thin part, if the absorption of the bluing agent is strong,
A hue difference occurs due to the thickness difference between the center part and the outer part of the lens,
The result is a lens with significantly poor appearance.

The spectacle lens formed from the polycarbonate resin composition of the present invention is extremely excellent in transparency, and has a luminous transmittance of 87% or more, preferably 88% or more at a thickness of 1.5 mm. Here, the luminous transmittance is a value measured under the conditions described later, and the present invention in which the polycarbonate resin is blended with ultraviolet absorbers (A) and (B), a phosphorus-based stabilizer, a release agent and a bluing agent. Means a value measured for a lens formed from the composition of When used as sunglasses or polarized lenses containing other dyes or pigments, the values are measured without these dyes or pigments.

The spectacle lens of the present invention has a high degree of transparency and a low yellowness, and the yellowness YI at a thickness of 5 mm.
(Yellowness Index) is 0.7-1.
8, preferably in the range of 1.0 to 1.6. If the value of the yellowness (YI) is less than 0.7, the transmitted light becomes bluish when molded into a lens, and if the yellowness exceeds 1.8, it becomes yellowish.

Further, since the polycarbonate spectacle lens has a high refractive index and a high impact resistance, the thickness and weight of the lens can be reduced. In general, a concave lens has an extremely thin center thickness of about 1.5 mm. Adopted. Therefore, the UV transmittance of 1.5 mm at the center is extremely important for protecting eyes. In the case of spectacle lenses having no power such as sunglasses and protective eyeglasses, a polycarbonate molding material that has been colored in advance may be used.In such a case, the spectacle lens of the present invention has a high ultraviolet absorbing effect and high transparency. It is extremely effective.

Since the spectacle lens of the present invention uses a polycarbonate resin as a base, it has a high impact strength and a high refractive index, as well as an ultraviolet absorbing effect, especially 380 to 400 mm.
Excellent in absorbing harmful ultraviolet rays of mm.

Thus, the spectacle lens of the present invention can be provided with either a type that emphasizes the luminous transmittance or a type that emphasizes the ultraviolet absorbing ability according to the application or purpose. That is, in applications where importance is placed on luminous transmittance, the ultraviolet absorber (A) is used in an amount of 0.1 to 0.5 part by weight and the ultraviolet absorber (B) is used in an amount of 0.01 to 0.1 based on 100 parts by weight of the polycarbonate resin. 1 part by weight, and the mixing ratio (weight) R of the ultraviolet absorber (A) and the ultraviolet absorber (B)
Is selected from the range of 0.05 to 0.5, the spectral transmittance at 380 nm at 1.5 mm thickness is 0.005% or less, the luminous transmittance is 88% or more, and the yellowness at 5.0 mm thickness (Y
It is preferred that I) be 0.7 to 1.8. In this case, the spectral transmittance at 400 nm is desirably 70% or less, preferably 60% or less.

In applications where importance is placed on ultraviolet absorption,
0.05 to 0.5 part by weight of ultraviolet absorber (A) and ultraviolet absorber (B) based on 100 parts by weight of polycarbonate resin
Is selected from the range of 0.05 to 0.3 parts by weight, and the blending ratio (weight) of the ultraviolet absorber (A) and the ultraviolet absorber (B) is selected.
When R is selected from the range of 0.5 to 4, the spectral transmittance at 400 nm at 1.5 mm thickness is 10% or less and the luminous transmittance is 8
7% or more, the yellowness (YI) at a thickness of 5.0 mm is 0.7.
It is preferable to set it to 1.8. In this case, 3
The spectral transmittance at 80 nm is desirably 0.005% or less.

[0035]

The present invention will be described in more detail with reference to the following examples. Parts are parts by weight, and the evaluation was made by the following method. (1) Spectral transmittance: Spectrophotometer CAR manufactured by Varian Japan
It measured in the wavelength range of 378-403 nm using Y-5. (2) Luminous transmittance: spectrophotometer CAR manufactured by Varian Japan
From the values of the spectral transmittance at each wavelength measured in the wavelength region of 360 nm to 800 nm using Y-5, JISZ-8
The luminous transmittance according to the following equation

[0036]

(Equation 1)

Wherein a is 380, b is 780, s
(Λ) is the spectral distribution of standard light used for displaying color, y
(Λ) is a color matching function, and τ (λ) is a spectral transmittance]. (3) Yellowness (YI): Spectrophotometer C manufactured by Varian Japan
The measurement was performed using ARY-5 in the wavelength range of 380 nm to 780 nm according to ASTM D-1925. (4) Lens hue: The lenses were compared visually under a fluorescent lamp. (5) APHA: 5 g of ultraviolet absorber is added to dichloromethane 1
It was dissolved in 00 ml and measured by comparing with a Hazen color number standard solution according to JIS K 6901. (6) Thermal stability: hue (L, a, h) of a sample plate (70 × 50 × 2 mm) obtained by continuously molding at a cylinder temperature of 340 ° C. by an injection molding machine using the pellets obtained in each example.
b) and the hue (L ', a', b ') of the sample plate obtained by molding after being retained in the cylinder for 10 minutes was measured with a color difference meter (manufactured by Nippon Denshoku Co., Ltd.) for 10 minutes. The degree of discoloration due to stagnation is expressed by the following formula: ΔE = [(LL ′) ² + (aa ′) ² + (bb ′) ² ]
^It was indicated by ΔE obtained by ^1/2 . ΔE of 0.5 or less was regarded as a pass.

Example 1 Bisphenol A and phosgene were polymerized and purified by an interfacial polymerization method according to a conventional method, and 100 parts of a polycarbonate resin powder having a viscosity average molecular weight of 23,700 was used as an ultraviolet absorber (A) and had an absorption maximum of 340 nm. 0.33 parts of certain 2- (2'-hydroxy-5'-tert-octylphenyl) benzotriazole, and 2- (3-tert-butyl-5- having an absorption maximum of 353 nm as an ultraviolet absorber (B).
(Methyl-2-hydroxyphenyl) -5-chlorobenzotriazole 0.02 parts, stearic acid stearate 0.2.
25 parts, 0.03 part of trisnonylphenyl phosphite and a bluing agent represented by the following formula:

[0039]

Embedded image

The compound (0.6 ppm) was added, and the mixture was sufficiently mixed with a tumbler and then pelletized at 260 to 280 ° C. by a 30 mm vent type extruder. From the pellets, a 1.5 mm thick sample plate for measuring luminous transmittance and a 5.0 mm thick sample plate for measuring yellowness (YI) were obtained at a cylinder temperature of 300 ° C. by an injection molding machine. 380 nm and 40
Table 1 shows the spectral transmittance, luminous transmittance, and YI at 0 nm. Further, using the above pellets, a cylinder temperature of 300 ° C., a mold temperature of 140 ° C., and a 220 ton injection molding machine were used.
A concave lens (spherical refractive power / cylindrical refractive power = S-3.00D / C-1.00D) was molded in 3 minutes of the molding cycle to obtain a lens with good hue. The results are shown in Table 1.

Example 2 2- (2′-hydroxy-5′-ter) in Example 1
The addition amount of t-octylphenyl) benzotriazole (ultraviolet absorber (A)) was 0.3 parts, and 2- (3-tert-
-Butyl-5-methyl-2-hydroxyphenyl) -5
Same as Example 1 except that the amount of chlorobenzotriazole (ultraviolet absorber (B)) was changed to 0.03 parts and the amount of bluing agent was changed to 0.7 ppm to keep bluish constant As a result, a lens having excellent ultraviolet blocking properties and good hue was obtained. The results are shown in Table 1.

Example 3 2- (2′-hydroxy-5′-ter) in Example 1
0.15 parts of t-octylphenyl) benzotriazole (ultraviolet absorber (A)) and 2- (3-ter
t-butyl-5-methyl-2-hydroxyphenyl)-
5-chlorobenzotriazole (ultraviolet absorber (B))
Was used in the same manner as in Example 1 except that the amount of the compound was changed to 0.06 parts and the amount of the bluing agent was changed to 0.8 ppm in order to keep the bluish color constant. Lens. The results are shown in Table 1.

Example 4 2- (2'-hydroxy-5'-ter) in Example 1
The addition amount of t-octylphenyl) benzotriazole (ultraviolet absorber (A)) was adjusted to 0.3 part, and 2- (3-te
rt-butyl-5-methyl-2-hydroxyphenyl)
Maximum absorption is 3 instead of -5-chlorobenzotriazole
2,2′-methylenebis [4- (1,1,1,49 nm
0.05 parts of (3,3-tetramethylbutyl) -6- (2H-benzotriazol-2-yl) phenol] (ultraviolet absorber (B)) and a bluing agent to further maintain a blue tint Was carried out in the same manner as in Example 1 except that the amount of was adjusted to 0.5 ppm, to obtain a lens having excellent ultraviolet blocking properties and good hue. The results are shown in Table 1.

Example 5 2- (2′-hydroxy-5′-ter) in Example 4
The addition amount of t-octylphenyl) benzotriazole (ultraviolet absorber (A)) was 0.25 parts, 2,2′-methylenebis [4- (1,1,3,3-tetramethylbutyl) -6
Except that the amount of-(2H-benzotriazol-2-yl) phenol] (ultraviolet absorber (B)) was changed to 0.08 parts, the ultraviolet ray blocking property was excellent and the hue was good as in Example 4. Lens. The results are shown in Table 1.

Example 6 2- (2′-hydroxy-5′-ter) in Example 1
The addition amount of t-octylphenyl) benzotriazole (ultraviolet absorber (A)) was 0.25 parts, and the ultraviolet absorber (B) was 2- (3-tert-butyl-5-methyl-2-hydroxyphenyl)- 2,2′-methylenebis [4] is newly added together with 0.1 part of 5-chlorobenzotriazole.
-(1,1,3,3-tetramethylbutyl) -6- (2H
-Benzotriazol-2-yl) phenol] 0.0
Except that 5 parts were used in combination and the amount of the bluing agent was changed to 0.7 ppm in order to keep the blue tint constant, a lens having excellent ultraviolet blocking properties and good hue was obtained in the same manner as in Example 1. 3
Table 2 shows the spectral transmittance, luminous transmittance, YI and hue of the lens at 80 nm and 400 nm.

Example 7 2- (2′-hydroxy-5′-ter) in Example 6
The addition amount of t-octylphenyl) benzotriazole (ultraviolet absorber (A)) was changed to 0.2 parts, and 2,2′-methylenebis [4- (1,1,3,3-tetramethylbutyl)- 6- (2H-benzotriazol-2-yl) phenol] (ultraviolet absorber (B)), except that the addition amount was changed to 0.1 part, the ultraviolet ray blocking property was excellent and the hue was the same as in Example 6. Good lens was obtained. The results are shown in Table 2.

Example 8 2- (2′-hydroxy-5′-ter) in Example 6
The addition amount of t-octylphenyl) benzotriazole (ultraviolet absorber (A)) was changed to 0.2 parts, and 2,2′-methylenebis [4- (1,1,3,3-tetramethylbutyl)- 6- (2H-benzotriazol-2-yl) phenol] (ultraviolet absorber (B)) was added at 0.15.
In the same manner as in Example 6, except that the amount of the bluing agent was changed to 1 ppm in order to keep the blue tint constant, thereby obtaining a lens having excellent ultraviolet blocking properties and good hue. Table 2 shows the results
It was shown to.

Example 9 2- (2'-hydroxy-5'-ter) in Example 6
The addition amount of t-octylphenyl) benzotriazole (ultraviolet absorber (A)) was changed to 0.2 part, and 2- (3-
The addition amount of tert-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole (UV absorber (B)) was 0.07 parts, 2,2′-methylenebis [4- (1,1,1,2) 3,3-tetramethylbutyl) -6
(2H-benzotriazol-2-yl) phenol]
The amount of the (UV absorber (B)) was changed to 0.15 parts, and the amount of the bluing agent was 0.8 in order to keep the bluish constant.
A lens having excellent ultraviolet blocking properties and good hue was obtained in the same manner as in Example 6 except that the content was set to ppm. The results are shown in Table 2.

Example 10 The amount of 2- (3-tert-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole (UV absorber (B)) in Example 6 was adjusted to 0.05.
Part, 2,2'-methylenebis [4- (1,1,3,3-tetramethylbutyl) -6- (2H-benzotriazole-
A lens having excellent ultraviolet blocking properties and good hue was obtained in the same manner as in Example 6 except that the addition amount of [2-yl) phenol] (ultraviolet absorber (B)) was changed to 0.1 part. The results are shown in Table 2.

Comparative Example 1 2- (3-tert-butyl-5-methyl-2-hydroxyphenyl) 5-chlorobenzotriazole (UV absorber (B)) in Example 1 was used,
The results are shown in Table 1 in the same manner as in Example 1 except that only 0.33 parts of (2'-hydroxy-5'-tert-octylphenyl) benzotriazole (ultraviolet absorbent (A)) was used. The hue of the lens is good, but 380 nm
And the absorption at 400 nm was insufficient.

Comparative Example 2 2- (2′-hydroxy-5′-ter) in Example 1
Without using t-octylphenyl) benzotriazole (ultraviolet absorber (A)), 2- (3-tert-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole (ultraviolet absorber (B )) Only 0.
The results are shown in Table 1 in the same manner as in Example 1 except that 02 parts were used. The hue of the lens was good, but the absorption at 380 nm and 400 nm was insufficient.

Comparative Example 3 2- (2′-hydroxy-5′-ter) in Example 1
Without using t-octylphenyl) benzotriazole (ultraviolet absorber (A)), 2- (3-tert-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole (ultraviolet absorber (B )) Only 0.
The results are shown in Table 1 in the same manner as in Example 1 except that 15 parts were used and the amount of the bluing agent was 1.1 ppm in order to keep the blue tint constant. The hue of the lens becomes dull blue,
The difference in hue between the center and the periphery was observed.

Comparative Example 4 2- (2′-hydroxy-5′-ter) in Example 6
Only 0.25 parts of (t-octylphenyl) benzotriazole (ultraviolet absorber (A)) was used, and 2- (3-tert-butyl-5-methyl-2-hydroxyphenyl)-was used as ultraviolet absorber (B). 5-chlorobenzotriazole and 2,2′-methylenebis [4- (1,1,3,
The results are shown in Table 2 in the same manner as in Example 6 except that [3-tetramethylbutyl) -6- (2H-benzotriazol-2-yl) phenol] was not used. The hue of the lens was good, but the absorption at 380 nm and 400 nm was insufficient.

Comparative Example 5 2- (2'-hydroxy-5'-te) in Example 10
The results are shown in Table 2 in the same manner as in Example 10 except that rt-octylphenyl) benzotriazole (ultraviolet absorbent (A)) was not used. The hue of the lens was good, but the absorption at 380 nm was insufficient.

Example 11 Bisphenol A and phosgene were polymerized and refined by an interfacial polymerization method, and 100 parts of a polycarbonate resin powder having a viscosity average molecular weight of 23,700 obtained by adding 2-
0.25 parts of (2'-hydroxy-5'-tert-octylphenyl) benzotriazole and 2,2'-methylenebis [4- (1,1,3,
0.08 parts of 3-tetramethylbutyl) -6- (2H-benzotriazol-2-yl) phenol, tetrakis (2,4-di-tert-butylphenyl) -4,4'-
0.02 parts of biphenylenediphosphonite (compound C),
0.2 parts of stearic acid monoglyceride and bluing agent of the following formula

[0056]

Embedded image

The compound (0.5 ppm) was added, mixed thoroughly in a tumbler, and pelletized at 260 to 280 ° C. by a 30 mm vent type extruder. Table 3 shows the spectral transmittance, luminous transmittance, YI and ΔE of the pellet at 380 nm and 400 nm. Cylinder temperature 3 by 220 ton injection molding machine using the above pellets
A concave lens (S-3.0D / C-1.00D) was molded at 00C, a mold temperature of 140C, and a molding cycle of 3 minutes to obtain a lens with good hue. The results are shown in Table 3.

Example 12 Except for adding 0.03 parts of trisnonylphenyl phosphite (compound D) as a phosphite-based compound in Example 11, it is excellent in ultraviolet ray blocking properties and heat resistance in the same manner as in Example 11. A lens with good hue was obtained.
The results are shown in Table 3.

[0059]

[Table 1]

[0060]

[Table 2]

[0061]

[Table 3]

In the table, A-1 represents 2- (2'-hydroxy-5'-tert-octylphenyl) benzotriazole (absorption maximum 340 nm), and B-1 represents 2- (2'-hydroxy-5'-tert-octylphenyl) benzotriazole.
(3-tert-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole (absorption maximum 353 nm), and B-2 is 2,2′-methylenebis [4- (1,1,3, 3-tetramethylbutyl) -6
(2H-benzotriazol-2-yl) phenol]
(Absorption maximum 349 nm), and Compound C was tetrakis (2,4-di-tert-butylphenyl) -4,4′-
Biphenylenediphosphonite is shown, and compound D is trisnonylphenyl phosphite.

[0063]

The spectacle lens obtained from the polycarbonate resin composition of the present invention can almost completely absorb harmful ultraviolet rays while maintaining excellent impact resistance and transparency, and is excellent in safety. The effect achieved is exceptional, and there is no hindrance in working and forming.

Claims (14)

(57) [Claims] (1) 100 parts by weight of a polycarbonate resin and (2) a wavelength of 3 when measured in a chloroform solution.
Ultraviolet absorber having an absorption maximum at 00 to 345 nm (A) 0.05 to 0.5 parts by weight and (3) an ultraviolet absorber having an absorption maximum at a wavelength of 346 to 400 nm when measured in a chloroform solution (B) An eyeglass lens formed from a resin composition consisting essentially of 0.01 to 0.3 parts by weight. 2. The ratio of the ultraviolet absorbent (A) to the ultraviolet absorbent (B) in the range of 0.05 to 4 as expressed by (B) / (A) (weight ratio). Eyeglass lens. 3. The spectacle lens according to claim 1, wherein a spectral transmittance at 380 nm at a thickness of 1.5 mm is 0.005% or less. 4. The spectacle lens according to claim 1, wherein a spectral transmittance at 400 nm at a thickness of 1.5 mm is 70% or less. 5. The spectacle lens according to claim 1, wherein the spectral transmittance at 380 nm at a thickness of 1.5 mm is 0.005% or less, and the spectral transmittance at 400 nm at a thickness of 1.5 mm is 70% or less. 6. The spectacle lens according to claim 1, wherein the spectral transmittance at 400 nm at a thickness of 1.5 mm is 10% or less. 7. The spectacle lens according to claim 1, wherein the spectral transmittance at 380 nm at a thickness of 1.5 mm is 0.005% or less, and the spectral transmittance at 400 nm at a thickness of 1.5 mm is 10% or less. 8. Luminous transmittance at a thickness of 1.5 mm is 87.
%. 9. The spectacle lens according to claim 1, wherein the yellowness (YI) at a thickness of 5.0 mm is in the range of 0.7 to 1.8. 10. The ultraviolet absorber (A) may be 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-
4-n-octoxybenzophenone, 2-hydroxy-
4-methoxy-2'-carboxybenzophenone, 2,4
-Dihydroxybenzophenone, 2- (2'-hydroxy-5'-methylphenyl) benzotriazole, 2-
[2-hydroxy-3- (3,4,5,6-tetrahydrophthalimidomethyl) -5-methylphenyl] benzotriazole, 2- (2-hydroxy-3,5-di-te
rt-butylphenyl) benzotriazole and 2-
The spectacle lens according to claim 1, which is at least one member selected from the group consisting of (2'-hydroxy-5'-tert-octylphenyl) benzotriazole. 11. The ultraviolet absorbent (A) may comprise 2- (2 ′
The spectacle lens according to claim 1, which is at least one member selected from the group consisting of -hydroxy-5'-methylphenyl) benzotriazole and 2- (2'-hydroxy-5'-tert-octylphenyl) benzotriazole. 12. The ultraviolet absorber (B) may be 2,2′-dihydroxy-4-methoxybenzophenone, 2- (3-
tert-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole, 2- (3,5-
Di-tert-butyl-2-hydroxyphenyl) -5
-Chlorobenzotriazole, 2,2'-methylenebis [4- (1,1,3,3-tetramethylbutyl) -6-
(2H-benzotriazol-2-yl) phenol], 2- [2-hydroxy-3,5-bis (α, α-dimethylbenzyl) phenyl] -2H-benzotriazole and 2- (3,5-di- The spectacle lens according to claim 1, which is at least one member selected from the group consisting of tert-amyl-2-hydroxyphenyl) benzotriazole. 13. The ultraviolet absorbent (B) comprises 2- (3-
tert-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole, 2,2′-methylenebis [4- (1,1,3,3-tetramethylbutyl)-
6- (2H-benzotriazol) -2-ylphenol] and 2- [2-hydroxy-3,5-bis (α, α
The spectacle lens according to claim 1, which is at least one member selected from the group consisting of -dimethylbenzyl) phenyl] -2H-benzotriazole. 14. The polycarbonate resin is 2,2-
The spectacle lens according to claim 1, which is a polycarbonate resin containing bis (4-hydroxyphenyl) propane as a main dihydric phenol component.