JP2011203634A - Spectacle lens - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a spectacle lens having excellent transparency and impact resistance and excellent ability to absorb ultraviolet light harmful to the human eyes.SOLUTION: The spectacle lens is obtained by molding a polycarbonate resin composition comprising 100 pts.wt. of (A) a polycarbonate resin, 0.5-10 pts.wt. of (B) a diglycerol fatty acid ester, 0.1-5 pts.wt. of (C) a specified compound represented by formula [(R1)R2N](R3SO)(R4SO)Nas an antistatic agent, and 0.1-0.9 pt.wt. of (D) an ultraviolet absorber, wherein R1 denotes 1C-4C alkyl; R2 denotes 1C-20C alkyl; R3 and R4 are 1C-4C perfluoroalkyl and these may be the same or different.

Description

  The present invention relates to a polycarbonate resin spectacle lens. More specifically, by using a diglycerin fatty acid ester and an ammonium salt having a specific structure in combination as an ultraviolet absorber and an antistatic agent, it is excellent in transparency and excellent in ultraviolet rays harmful to human eyes. The present invention relates to a polycarbonate resin spectacle lens that exhibits absorption ability and has less dust adhesion in the manufacturing process.

  Polycarbonate resin is excellent in transparency, impact resistance, and the like, and expectation as a material for spectacle lenses is increasing. Polycarbonate resin eyeglass lenses are safer due to their high impact resistance even if they are thinner and lighter than conventional glass lenses and acrylic plastic lenses. It has come to be used as a material for lenses such as protective glasses, sunglasses, and eyesight correction glasses.

  Recently, the possibility of inducing keratitis and cataracts by ultraviolet rays has been pointed out, and in order to protect the eyes from ultraviolet rays, the development of spectacle lenses imparted with ultraviolet absorbing ability has been desired.

In the conventional technique, in order to absorb ultraviolet rays of 400 nm or less in a polycarbonate resin spectacle lens, it is necessary to add a large amount of an ultraviolet absorber. In this case, since the ultraviolet absorber is generally sublimable, it has a problem that the mold is contaminated or the resulting lens is fogged.
Japanese Patent No. 3354066 Patent No. 3354667

  An object of the present invention is to provide a spectacle lens that is excellent in transparency and impact resistance, and further has an excellent ability to absorb ultraviolet rays harmful to human eyes. Furthermore, there is a problem of dust adhesion in the process of manufacturing a spectacle lens, and it is necessary to provide antistatic properties.

  As a result of diligent investigations to solve the above problems, the present inventor has added a UV absorber to a polycarbonate resin so that it has excellent transparency and absorbs UV rays harmful to human eyes. In order to complete the present invention, it is found that a polycarbonate resin spectacle lens can be obtained, and that antistatic properties are imparted to reduce dust adhesion during lens fabrication and to improve lens fogging. It came.

That is, the present invention includes 100 parts by weight of the polycarbonate resin (A), 0.5 to 10 parts by weight of the diglycerin fatty acid ester (B), and 0.1 to 5 parts by weight of the compound (C) represented by the following formula (1). And a spectacle lens formed by molding a polycarbonate resin composition comprising 0.05 to 1.5 parts by weight of an ultraviolet absorber (D).
Formula (1):
[(R ¹ ) ₃ R ² N] ^+. (R ³ SO ₂ ) (R ⁴ SO ₂ ) N ⁻
(In the formula, R ¹ represents an alkyl group having 1 to 4 carbon atoms, R ² represents an alkyl group having 1 to 20 carbon atoms, and R ³ and R ⁴ are perfluoroalkyl groups having 1 to ⁴ carbon atoms. These may be the same or different.)

  Since the spectacle lens of the present invention uses a polycarbonate resin together with a diglycerin fatty acid ester and an ammonium salt having a specific structure as an antistatic agent, high-quality spectacles are prevented by preventing the adhesion of dust in the process of manufacturing the spectacle lens. The lens is characterized in that it has an excellent ability to absorb ultraviolet rays harmful to human eyes by adding an ultraviolet absorber.

  Hereinafter, the present invention will be described in detail.

  The polycarbonate resin (A) used in the present invention is obtained by a phosgene method in which various dihydroxydiaryl compounds and phosgene are reacted, or a transesterification method in which a dihydroxydiaryl compound and a carbonate such as diphenyl carbonate are reacted. A typical example of the polymer is a polycarbonate resin produced from 2,2-bis (4-hydroxyphenyl) propane (bisphenol A).

  Examples of the dihydroxydiaryl compound include bisphenol 4-, bis (4-hydroxyphenyl) methane, 1,1-bis (4-hydroxyphenyl) ethane, 2,2-bis (4-hydroxyphenyl) butane, 2, 2-bis (4-hydroxyphenyl) octane, bis (4-hydroxyphenyl) phenylmethane, 2,2-bis (4-hydroxyphenyl-3-methylphenyl) propane, 1,1-bis (4-hydroxy-3) -Tert-butylphenyl) propane, 2,2-bis (4-hydroxy-3-bromophenyl) propane, 2,2-bis (4-hydroxy-3,5-dibromophenyl) propane, 2,2-bis ( Bis (hydroxyaryl) alkanes such as 4-hydroxy-3,5-dichlorophenyl) propane, 1,1- (4-hydroxyphenyl) cyclopentane, bis (hydroxyaryl) cycloalkanes such as 1,1-bis (4-hydroxyphenyl) cyclohexane, 4,4'-dihydroxydiphenyl ether, 4,4'-dihydroxy-3 Dihydroxy diaryl ethers such as 3,3'-dimethyldiphenyl ether, dihydroxy diaryl sulfides such as 4,4'-dihydroxydiphenyl sulfide, 4,4'-dihydroxydiphenyl sulfoxide, 4,4'-dihydroxy-3,3 ' Dihydroxy diaryl sulfoxides such as dimethyldiphenyl sulfoxide, dihydroxy diary such as 4,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfone Sulfone, and the like.

  These are used individually or in mixture of 2 or more types. In addition to these, piperazine, dipiperidyl hydroquinone, resorcin, 4,4'-dihydroxydiphenyl, and the like may be mixed and used.

  Furthermore, the above dihydroxyaryl compound and a trivalent or higher phenol compound as shown below may be used in combination.

  Trihydric or higher phenols include phloroglucin, 4,6-dimethyl-2,4,6-tri- (4-hydroxyphenyl) -heptene, 2,4,6-dimethyl-2,4,6-tri- (4 -Hydroxyphenyl) -heptane, 1,3,5-tri- (4-hydroxyphenyl) -benzol, 1,1,1-tri- (4-hydroxyphenyl) -ethane and 2,2-bis- [4 4- (4,4'-dihydroxydiphenyl) -cyclohexyl] -propane and the like.

  The viscosity average molecular weight of the polycarbonate resin is usually 10,000 to 100,000, preferably 15,000 to 35,000. In producing such a polycarbonate resin, a molecular weight regulator, a catalyst and the like can be used as necessary.

  The diglycerin fatty acid ester (B) used in the present invention can be obtained by esterification of glycerin and a fatty acid. As the diglycerin fatty acid ester (B), an ester compound of a fatty acid having 12 to 18 carbon atoms and diglycerin is preferably used. If the carbon number is less than 12, the sustainability of the antistatic performance is inferior, and if the carbon number exceeds 18, the antistatic property may be inferior. Examples of the fatty acid having 12 to 18 carbon atoms include lauric acid, tridecylic acid, pentadecylic acid, palmitic acid, margaric acid, and stearic acid.

  Specific examples of the diglycerin fatty acid ester (B) include diglycerin monolaurate, diglycerin monomyristate, and diglycerin monostearate. Diglycerin monolaurate is preferably used, and RIKEN vitamins It is easily available as Poem DL-100 manufactured by the company.

  The compounding quantity of the diglycerol fatty acid ester (B) used by this invention is 0.5-10 weight part per 100 weight part of polycarbonate resin (A). When the blending amount is less than 0.5 parts by weight, the antistatic property is inferior, and when it exceeds 10 parts by weight, the degree of yellowing increases due to the decrease in thermal stability, which is not preferable. More preferably, it is 0.5-7.0 weight part, More preferably, it is the range of 0.6-1.5 weight part.

The compound (C) as an antistatic agent used in the present invention is a fluorine-containing organic ammonium salt having a chemical structure represented by the following formula (2).
Formula (2):
[(R ¹ ) ₃ R ² N] ^+. (R ³ SO ₂ ) (R ⁴ SO ₂ ) N ⁻
(In the formula, R ¹ represents an alkyl group having 1 to 4 carbon atoms, R ² represents an alkyl group having 1 to 20 carbon atoms, and R ³ and R ⁴ are perfluoroalkyl groups having 1 to ⁴ carbon atoms. These may be the same or different.)

Among the compounds (C) represented by the above formula (2), 1,1,1-tributyl-1-methylammonium bis (trifluoromethanesulfonyl) imide represented by the following formula (3) can be preferably used. .
Formula (3):

  The compounding quantity of a compound (C) is 0.1-5 weight part per 100 weight part of polycarbonate resin (A). If the blending amount is less than 0.1 parts by weight, the antistatic property is inferior, and if it exceeds 5 parts by weight, the transparency is lowered, which is not preferable. More preferably, it is 0.2-3.0 weight part, More preferably, it is the range of 0.3-1.0 weight part.

  Especially, blended with 0.6 to 1.5 parts by weight of diglycerin fatty acid ester (B) and 0.3 to 1.0 parts by weight of compound (C) with respect to 100 parts by weight of polycarbonate resin (A). Then, it is preferable because a remarkable synergistic effect is exhibited in the antistatic performance, and excellent thermal stability and transparency can be exhibited.

  Examples of the ultraviolet absorber (D) used in the present invention include benzophenone-based ultraviolet absorbers, triazine-based ultraviolet absorbers, and benzotriazole-based ultraviolet absorbers, but benzo has little light absorption in the visible light region. Triazole ultraviolet absorbers are preferred.

Among these, 2- (2′-hydroxy-3′-tert-butyl-5′-methylphenyl) -5-chlorobenzotriazole represented by the following formula (4) can be preferably used.
General formula (4)

  The addition amount of a ultraviolet absorber (D) is 0.05-1.5 weight part with respect to 100 weight part of polycarbonate resin (A). If the amount is less than 0.05 parts by weight, the ultraviolet ray absorbing ability is insufficient, and if it exceeds 1.5 parts by weight, the light transmittance decreases or the haze increases, so that the optical characteristics as a spectacle lens are increased. Is not preferable because it becomes insufficient. Especially preferably, it is the range of 0.3-0.5 weight part.

  The mixing method of the polycarbonate resin (A), diglycerin fatty acid ester (B), compound (C) and ultraviolet absorber (D) of the present invention is not particularly limited, and any mixer such as a tumbler, ribbon blender, high speed The method of mixing with a mixer etc. and melt-kneading with an extruder etc. is mentioned.

  There is no restriction | limiting in particular as a method of shape | molding the spectacle lens of this invention, A well-known injection molding method, injection / compression molding method, etc. can be used.

  Furthermore, in order to color the spectacle lens within a range not impairing the effects of the present invention, various kinds of dyes may be blended in the polycarbonate resin composition of the present invention in combination of one or more. If necessary, other additives such as antioxidants [2,6-di-tert-butyl-4-methylphenol, 2- (1-methylcyclohexyl) -4,6-dimethylphenol, 2,2 -Methylenebis- (4-ethyl-6-tert-methylphenol), 4,4'-thiobis- (6-tert-butyl-3-methylphenol), dilauryl thiodipropionate, tris (di-nonylphenyl) Examples thereof include phosphite. ], Lubricant [paraffin wax, stearic acid, hydrogenated oil, stearamide, methylene bisstearamide, ethylene bisstearamide, n-butyl stearate, ketone wax, octyl alcohol, lauryl alcohol, hydroxystearic acid triglyceride, etc. The ], Fluidity improvers [for example, triphenyl phosphate. ], Decomposition inhibitor for polycarbonate resin, mold release agent [natural beeswax, synthetic beeswax, monohydric alcohol and monohydric fatty acid ester (eg stearyl stearate), polyhydric alcohol partial ester (eg glycerol monoester, glycerol diester) , Saturated esters of polyhydric alcohol (eg glycerol triester, pentaerythritol tetrastearate), polyethylene wax (low molecular weight polyethylene or partially hydrophilized polyethylene wax)], etc. are added as necessary. Can do.

  EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. “Parts” are based on weight unless otherwise specified.

The details of each component used are as follows.
Polycarbonate resin (A):
Polycarbonate resin synthesized from bisphenol A and phosgene (Sumitomo Dow Caliber 200-13, viscosity average molecular weight 21000, hereinafter abbreviated as PC)
Diglycerin fatty acid ester (B):
Diglycerin monolaurate (DL-100 manufactured by Riken Vitamin Co., hereinafter abbreviated as antistatic agent B)
Compound (C) as antistatic agent:
1,1,1-tributyl-1-methylammonium bis (trifluoromethanesulfonyl) imide (manufactured by 3M FC-4400, hereinafter abbreviated as antistatic agent C)
UV absorber (D):
2- (2′-hydroxy-3′-t-butyl-5′-methylphenyl) -5-chlorobenzotriazole (SEESORB 703 manufactured by Cypro Kasei Co., Ltd., hereinafter abbreviated as UVA)

Based on the blending components and blending amounts shown in Tables 1 to 3, each was put into a tumbler and dry-mixed for 10 minutes, and then a twin-screw extruder (Nippon Steel Works TEX30α (L / D = 42, Φ = 30 mm)) Was used and kneaded at a melting temperature of 260 ° C. to obtain pellets of a resin composition.
A test piece having a width of 50 mm, a length of 90 mm, and a thickness of 2 mm was prepared by using an injection molding machine (J100EII-P manufactured by Nippon Steel Works) under the condition of 290 ° C. using the obtained pellet.

Various evaluation items and measurement methods in the present invention will be described.
1. Surface resistivity (Rs):
The obtained test piece was conditioned for 24 hours under the conditions of 23 ° C. and 50% relative humidity, and then using a superinsulator (SME 8311 manufactured by Sicid Electrostatic Co., Ltd.) with a measurement voltage of 500 V and a sampling time of 60 seconds. The surface resistivity was measured. The case where the surface specific resistance Rs was less than 1 × 10 ¹⁴ was regarded as acceptable.
2. Half-life:
Using the obtained test piece, the half-life was measured with a Static Honest Meter H-0110 manufactured by Sicid. First, an electric charge of 10 KV is continuously applied until the withstand voltage of the test piece becomes constant. Thereafter, the charge was stopped, the decay of the charged voltage was observed, and the time until the initial charged voltage was halved was measured to determine the half-life. A half-life of 10 seconds or less was accepted.
3. Total light transmittance:
Using the obtained test piece, the total light transmittance was measured in accordance with JIS K7361.
70% or more was accepted.
4). Yellowness index (YI):
Using the obtained test piece, the yellowness index (YI) was measured according to ASTM D-1925. 10 or less was regarded as acceptable.
5. Spectral transmittance (400nm)
The spectral transmittance was measured in accordance with JIS K7105 at a wavelength of 400 nm using a CMS-35 spectrophotometer manufactured by Murakami Color Research Laboratory. Less than 5 was accepted.

As shown in Table 1, when the polycarbonate resin composition satisfied the requirements of the present invention (Examples 1 to 6), all the required performances including the surface resistivity satisfied the required level. As shown in Examples 1 to 3, Example 5 and Examples 7 to 9, an excellent antistatic effect is obtained even in a polycarbonate resin composition in a region where the total amount of the antistatic agents B and (C) is relatively small. Indicated.
Example 4 was an example in which 1.5 parts of the antistatic agent B and 0.5 part of the antistatic agent C were used in combination, and the surface resistivity was on the order of 10 ¹² Ω. On the other hand, in the example in which only 1.5 part of the antistatic agent B was blended alone (Comparative Example 1) and the example in which only 0.5 part of the antistatic agent C was blended alone (Comparative Example 2), the surface resistivity was 10 ¹⁵ Ω or more. Indicated. As can be seen from this example, by using the antistatic agent B and the antistatic agent C in combination, a synergistic effect in the antistatic performance was obtained.

On the other hand, as shown in Tables 2 and 3, when the configuration of the present invention was not satisfied, each case had some drawbacks.
Comparative Example 1 was a case where the antistatic agent C was not blended, and resulted in inferior surface resistivity and half-life.
Comparative Example 2 was a case where the antistatic agent B was not blended, and resulted in poor surface resistivity and half life.
Comparative Example 3 was a case where the blending amount of the antistatic agent B was less than the prescribed amount, and resulted in poor surface resistivity and half-life.
Comparative Example 4 was a case where the blending amount of the antistatic agent B was larger than the specified amount, and YI was inferior.
Comparative Example 5 was a case where the blending amount of the antistatic agent C was less than the prescribed amount, and the surface resistivity and half-life were inferior.
The comparative example 6 is a case where the compounding quantity of the antistatic agent C is larger than a prescribed quantity, and resulted in inferior transmittance and YI.
Comparative Example 7 was a case where the blending amount of UVA was less than the prescribed amount, and the spectral transmittance at 400 nm was inferior.
Comparative Example 8 was a case where the blending amount of UVA was larger than the prescribed amount, and YI was inferior.

Claims (3)

100 parts by weight of the polycarbonate resin (A), 0.5 to 10 parts by weight of the diglycerin fatty acid ester (B), 0.1 to 5 parts by weight of the compound (C) represented by the following formula (1), and an ultraviolet absorber (D ) A spectacle lens formed by molding a polycarbonate resin composition comprising 0.05 to 1.5 parts by weight.
[(R ¹ ) ₃ R ² N] ^+. (R ³ SO ₂ ) (R ⁴ SO ₂ ) N ⁻
(In the formula, R ¹ represents an alkyl group having 1 to 4 carbon atoms, R ² represents an alkyl group having 1 to 20 carbon atoms, and R ³ and R ⁴ are perfluoroalkyl groups having 1 to ⁴ carbon atoms. These may be the same or different.)   The spectacle lens according to claim 1, wherein the ultraviolet absorber (D) is 2- (2'-hydroxy-3'-t-butyl-5'-methylphenyl) -5-chlorobenzotriazole. The spectacle lens according to claim 1, wherein the compound (C) is 1,1,1-tributyl-1-methylammonium bis (trifluoromethanesulfonyl) imide represented by the following formula (2).
Formula (2):