WO2018212343A1 - ポリカーボネート樹脂レンズ、およびポリカーボネート樹脂組成物 - Google Patents
ポリカーボネート樹脂レンズ、およびポリカーボネート樹脂組成物 Download PDFInfo
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- WO2018212343A1 WO2018212343A1 PCT/JP2018/019364 JP2018019364W WO2018212343A1 WO 2018212343 A1 WO2018212343 A1 WO 2018212343A1 JP 2018019364 W JP2018019364 W JP 2018019364W WO 2018212343 A1 WO2018212343 A1 WO 2018212343A1
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/132—Phenols containing keto groups, e.g. benzophenones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/10—Transparent films; Clear coatings; Transparent materials
Definitions
- the present invention relates to a polycarbonate resin lens and a polycarbonate resin composition containing an ultraviolet absorber.
- Non-patent document 1 describes the effect of short-wavelength blue light having a wavelength of about 420 nm on the eye.
- Non-patent Document 1 retinal nerve cells (rat cultured retinal nerve R28 cells) are irradiated with blue LED light having different peak wavelengths of 411 nm and 470 nm, and the damage to the retinal nerve cells of blue LED light is verified.
- blue light having a peak wavelength at 411 nm is irradiated (4.5 w / m 2 )
- cell death of retinal neurons is caused within 24 hours
- blue light having a peak wavelength at 470 nm It has been shown that the same amount of irradiation does not change the cells. That is, it is shown that it is important to prevent eye damage to suppress exposure by light having a wavelength of 400 to 420 nm.
- exposure of eyes to blue light for a long time is concerned about eye strain and stress, and is considered to be a factor causing age-related macular degeneration.
- Polycarbonate resin has a high refractive index and has excellent properties such as transparency and impact resistance, and has recently attracted attention as a material for lenses, particularly a material for eyeglass lenses. Glasses made of polycarbonate resin have a higher impact strength than conventional glass lenses and plastic lenses made by cast polymerization (hereinafter sometimes referred to as cast lenses), so they can be reduced in weight and reduced in weight. Excellent safety and high functionality. Therefore, spectacle lenses made of polycarbonate resin have been used for vision correction lenses, sunglasses, protective glasses, and the like. Furthermore, since polycarbonate resin can be injection-molded, it has higher productivity than the cast lens.
- the polycarbonate resin itself has an ultraviolet absorbing ability, and since it is a thermoplastic resin, the influence of the addition of an ultraviolet absorber is less than that of a polymerization curable resin.
- An ultraviolet absorber can be blended when melt molding. Therefore, an arbitrary ultraviolet absorber having ultraviolet absorbing ability can be easily contained in a region different from the polycarbonate resin, and for example, an ultraviolet absorber on the long wavelength side can be blended.
- the conventional polycarbonate resin is limited to absorbing ultraviolet rays up to a wavelength of 375 nm, and when trying to absorb light having a longer wavelength than this, the content of the ultraviolet absorber is added 2 to 10 times the usual amount.
- UV absorbers are sublimable, so adding a large amount of UV absorbers adversely affects the appearance of the resulting lens because the UV absorbers sublimate and contaminate the mirror mold during polycarbonate resin injection molding. .
- Patent Document 1 discloses a method of cutting ultraviolet rays having a wavelength of 400 nm or less by using an ultraviolet absorber having an absorption maximum at a wavelength of 300 to 345 nm and an ultraviolet absorber having an absorption maximum at a wavelength of 346 to 400 nm.
- the spectral transmittance of ultraviolet light having a wavelength of 400 nm is 10% or less, which is not always sufficient to protect the eyes from ultraviolet light.
- Patent Document 2 discloses a spectacle lens formed from a polycarbonate resin composition containing a specific amount of a benzotriazole ultraviolet absorber having a specific structure. However, there is only a disclosure regarding the spectral transmittance at a wavelength of 400 nm, and there is no description regarding the light transmittance at a wavelength of 420 nm.
- Patent Document 3 discloses an aromatic polycarbonate resin composition for eyeglass lenses comprising an aromatic polycarbonate resin, a saturated aliphatic hydrocarbon, a benzotriazole-based ultraviolet absorber, and a phosphite-based stabilizer having a specific structure. Yes. However, there is only a disclosure regarding the spectral transmittance at a wavelength of 400 nm, and there is no description regarding the light transmittance at a wavelength of 420 nm.
- Patent Document 4 discloses a spectacle lens containing a polycarbonate resin, a saturated aliphatic hydrocarbon, a benzotriazole ultraviolet absorber having a vapor pressure of 1 ⁇ 10 ⁇ 8 Pa or less at 25 ° C., and a phosphite ester stabilizer.
- An aromatic polycarbonate resin composition is disclosed. This document discloses that when a UV absorber having a high vapor pressure is used, the defective rate of the lens molded product is increased. However, the composition disclosed in Patent Document 4 does not reach the ultraviolet cut wavelengths up to 384 nm and 420 nm.
- Patent Document 5 discloses a light-shielding lens for protective glasses containing an indole ultraviolet absorber having a specific melting point, and in its detailed description, polycarbonate resin is described as an example of a synthetic resin. However, Patent Document 5 relates to a light-shielding lens, and there is no example of actually blending with a polycarbonate resin, and there is no description about the molecular weight of the polycarbonate resin.
- a light-shielding lens for example, a resin spectacle lens mainly composed of diethylene glycol bisallyl carbonate resin called CR39 and blended with organic acid cobalt is used, and casting polymerization is performed so that a polarizing film is embedded in the resin.
- a medical lens having both an antiglare effect and a polarization characteristic is known (Patent Document 6).
- Patent Document 6 a medical lens having both an antiglare effect and a polarization characteristic is known (Patent Document 6).
- this light-shielding lens has low impact resistance and exhibits brittle fracture. Accordingly, there is a demand for a lens having a high total light transmittance and a high impact resistance that suppresses ultraviolet / visible light of 420 nm or less.
- the present invention solves the above-described problems in the prior art, and specifically aims at the following points.
- the first object of the present invention is a polycarbonate which is excellent in impact resistance, mold stain resistance, transparency, color tone stability, has an excellent effect of cutting off ultraviolet rays of a specific wavelength, and is suppressed from yellowing due to ultraviolet rays.
- the object is to provide a resin lens.
- a second object of the present invention is to provide a lens that is excellent in the effect of cutting blue light having a wavelength of 420 nm, has less influence on the eye of the blue light, and has a high total light transmittance.
- a third object of the present invention is to provide a polycarbonate resin composition in which contamination of a mold surface due to sublimation of an ultraviolet absorber is suppressed during molding such as injection molding, and a desired lens can be obtained with high yield. It is providing the manufacturing method of the lens using the said composition.
- a lens comprising 0.01 to 0.8 parts by mass of an indole compound represented by the following general formula (1) with respect to 100 parts by mass of a polycarbonate resin having a weight average molecular weight of 40,000 to 60,000.
- R 1 represents an optionally branched alkyl group or aralkyl group
- R 2 represents —CN or —COOR 3
- R 3 represents an optionally substituted alkyl group or aralkyl group.
- a resin composition comprising 0.01 to 0.8 parts by mass of an indole compound represented by the following general formula (1) with respect to 100 parts by mass of a polycarbonate resin having a weight average molecular weight of 40,000 to 60,000.
- a resin composition comprising 0.01 to 0.8 parts by mass of an indole compound represented by the following general formula (1) with respect to 100 parts by mass of a polycarbonate resin having a weight average molecular weight of 40,000 to 60,000.
- a method for producing a lens comprising a step of molding by injection molding. (Wherein R 1 represents an optionally branched alkyl group or aralkyl group, R 2 represents —CN or —COOR 3 , and R 3 represents an optionally substituted alkyl group or aralkyl group. )
- the present invention it is excellent in impact resistance, mold stain resistance, transparency, and color tone stability, and is excellent in the effect of cutting off ultraviolet rays having a specific wavelength, so that yellowing due to ultraviolet rays is suppressed, and blue having a wavelength of 420 nm is further suppressed. Since it has an excellent light-cutting effect, the influence of the blue light on the eye can be reduced, and a polycarbonate resin lens having a high total light transmittance can be provided. In addition, the lens of the present invention is excellent in storage stability with no change in surface condition even after aging. Furthermore, according to the present invention, it is possible to provide a polycarbonate resin composition capable of suppressing contamination of the mold surface and obtaining a desired lens with a high yield, and a method for producing a lens using the composition.
- the lens of this embodiment includes 0.01 to 0.8 parts by mass of a predetermined indole compound with respect to 100 parts by mass of a polycarbonate resin having a weight average molecular weight of 40,000 to 60,000.
- the polycarbonate resin is an aromatic polycarbonate resin obtained by reacting a dihydric phenol and a carbonate precursor.
- the dihydric phenol include, for example, 2,2-bis (4-hydroxyphenyl) propane (commonly called 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) phenylethane, 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, 2,2-bis (4 -Hydroxy-3,5-dibromophenyl) propane, bis (hydroxy) such as 2,2-bis (4-hydroxy-3,5-dichlorophenyl) propane Geb) al.
- dihydric phenols 2,2-bis (4-hydroxyphenyl) propane (bisphenol A) is preferred as the main dihydric phenol component, particularly 70 mol% or more, especially 80% of the total dihydric phenol component.
- bisphenol A 2,2-bis (4-hydroxyphenyl) propane
- the main dihydric phenol component particularly 70 mol% or more, especially 80% of the total dihydric phenol component.
- the thing whose mol% or more is bisphenol A is preferable.
- an aromatic polycarbonate resin in which the dihydric phenol component is substantially bisphenol A.
- the polycarbonate resin is preferably a bisphenol A type polycarbonate.
- the basic means for producing the polycarbonate resin will be briefly described.
- the reaction of a dihydric phenol component and phosgene is usually performed in the presence of an acid binder and an organic solvent.
- the acid binder include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and amine compounds such as pyridine.
- the organic solvent for example, halogenated hydrocarbons such as methylene chloride and chlorobenzene are used.
- a catalyst such as a tertiary amine or a quaternary ammonium salt can be used to promote the reaction
- a terminal terminator such as an alkyl-substituted phenol such as phenol or p-tert-butylphenol is used as a molecular weight regulator. It is desirable to use it.
- the reaction temperature is usually 0 to 40 ° C.
- the reaction time is several minutes to 5 hours
- the pH during the reaction is preferably maintained at 10 or more.
- transesterification method using a carbonic acid diester as a carbonate precursor, a predetermined proportion of a dihydric phenol component and a carbonic acid diester are stirred with heating in the presence of an inert gas, and the resulting alcohol or phenols are distilled. It is a method to make it come out.
- the reaction temperature varies depending on the boiling point of the alcohol or phenol produced, but is usually in the range of 120 to 300 ° C.
- the reaction is carried out while distilling off the alcohol or phenol produced under reduced pressure from the beginning.
- a normal transesterification reaction catalyst can be used.
- Examples of the carbonic acid diester used in the transesterification include diphenyl carbonate, dinaphthyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, and the like, and diphenyl carbonate is particularly preferable.
- the molecular weight of the polycarbonate resin is preferably 40,000 to 60,000, more preferably 40,000 to 50,000, and more preferably 40,000 to 45,000 as the weight average molecular weight measured by gel permeation chromatography in terms of standard polystyrene. 000 is particularly preferred.
- Eyeglass lenses are precision molded, and it is important to accurately transfer the mirror surface of the mold to give the specified curvature and power. A low-viscosity resin with good melt flow is desirable, but if it is too low The impact strength that is characteristic of polycarbonate resin cannot be maintained. On the other hand, when the viscosity is high, the handling property is lowered and the productivity of the lens is lowered. Therefore, when the weight average molecular weight of the polycarbonate resin is in the above range, the mold transferability is excellent, the impact resistance is excellent, and the lens productivity is also excellent.
- the indole compound used in the present embodiment is an ultraviolet absorber represented by the following general formula (1).
- R 1 represents an optionally branched alkyl group or aralkyl group
- R 2 represents —CN or —COOR 3
- R 3 represents an optionally substituted alkyl group or aralkyl group.
- examples of R 1 include an alkyl group having 1 to 12 carbon atoms or an aralkyl group which may have a branched chain. Specific examples include methyl, ethyl, (iso) butyl, t-butyl, hexyl, octyl, 2-ethylhexyl, dodecyl, benzyl and the like.
- R 2 is a nitrile (-CN) group or an ester (-COOR 3) group.
- R 3 include an alkyl group having 1 to 20 carbon atoms or an aralkyl group which may have a substituent. Specific examples of R 3 include those exemplified for R 1 above and ⁇ -cyanoethyl group, ⁇ -chloroethyl group, ethoxypropyl group, hydroxyalkyl group, alkoxyalkoxyalkyl group.
- the indole compound represented by the general formula (1) is not sublimable, and contamination of the mirror mold during the injection molding of the polycarbonate resin is suppressed, and even when a large amount of the compound is added. Contamination of the mirror mold is suppressed. Furthermore, the lens containing the indole-based compound has no change in surface state even after time, and is excellent in storage stability.
- the indole compound (1) is obtained by subjecting a compound represented by the following general formula (2) to a condensation reaction of a compound represented by the following general formula (3).
- R 1 has the same meaning as R 1 in the general formula (1).
- R 2 has the same meaning as R 2 in the general formula (1).
- ⁇ -cyanoacetic acid ester examples include cyanoacetic acid methyl ester, cyanoacetic acid ethyl ester (ethyl cyanoacetate), cyanoacetic acid isopropyl ester, cyanoacetic acid butyl ester, cyanoacetic acid tertiary butyl ester, cyanoacetic acid amyl ester, cyanoacetic acid Examples thereof include octyl esters, esters from cyanoacetic acid and higher alcohols (for example, undecyl alcohol, dodecyl alcohol, C13 to C20 aliphatic alcohol), cyanoacetic acid benzyl ester, and the like.
- the amount of compound (3) used is preferably 0.9 to 1.2 equivalents relative to compound (2).
- the condensation reaction can be carried out in a solvent at 10 ° C. to the boiling point of the solvent at 0.5 to 20 hours.
- the solvent alcohols (for example, methanol, ethanol and the like), acetic anhydride and the like can be used.
- bases for example, pyridine, triethylamine, etc.
- catalysts for example, pyridine, triethylamine, etc.
- the compound (1) is obtained by separation and purification if necessary.
- the separation and purification method is not particularly limited.
- the reaction product mixture is discharged into water or the like, and the compound (1) is precipitated as a precipitate, and then separated. In general, it can be purified by washing with an alcohol solvent or the like, but if necessary, it may be purified by recrystallization or the like.
- the starting compound (2) can be easily synthesized by a known method. For example, it can be easily synthesized by adding phosphoryl oxychloride to a dimethylformamide solution of a compound represented by the following general formula (4) to formylate (Vilsmeier reaction).
- R 1 has the same meaning as R 1 in the general formula (1).
- a compound represented by the following formula (5) and a compound (3) are subjected to a condensation reaction to obtain a compound represented by the following general formula (6), and then alkyl.
- the compound (1) can also be obtained by reacting with an agent or an aralkylating agent for N-alkylation or aralkylation.
- R 3 is hydrogen, the derivative can be obtained by treatment with an alkylating agent.
- R 2 has the same meaning as R 2 in the general formula (1).
- the condensation reaction of the compound (5) and the compound (3) can be performed under the same conditions as in the case of the aforementioned condensation reaction.
- N-alkylation or aralkylation may be performed by a usual method.
- the alkylating agent or aralkylating agent include alkyl halides or halogenated aralkyls (for example, methyl iodide, benzyl iodide), dialkyl sulfates or diaalkyl sulfates (for example, dimethyl sulfate, dibenzyl sulfate), and aromatic sulfonates. Can be mentioned.
- the indole compound (1) synthesized as described above generally has a maximum absorption at 380 to 400 nm. Accordingly, it is possible to effectively shield ultraviolet rays having a wavelength in this range.
- the compounding amount of the indole compound (1) is preferably 0.01 to 0.8 parts by mass, more preferably 0.01 to 0.3 parts by mass with respect to 100 parts by mass of the polycarbonate resin.
- the amount is more preferably 0.02 to 0.3 parts by mass, and particularly preferably 0.02 to 0.1 parts by mass.
- the above blending amount is 0.01 parts by mass or more, the ability to shield ultraviolet / visible light of 420 nm or less is clearly expressed, and when it is 0.8 parts by mass or less, the yellowness (YI) of the polycarbonate resin is preferred. Value) is preferable. Moreover, when it is 0.8 mass part or less, since favorable impact strength can be hold
- the polycarbonate resin composition of the present embodiment can be obtained by mixing a polycarbonate resin and an indole compound represented by the general formula (1).
- the mixing method is not particularly limited, but the mixing can be performed by melt kneading with a melt extruder (short axis or biaxial).
- the indole compound represented by the general formula (1) may be mixed with the polycarbonate resin at a high concentration and then mixed as a master batch with the polycarbonate resin.
- the polycarbonate resin composition according to this embodiment is desired to have as little foreign matter content as possible, and filtration of the polycarbonate resin composition with a polymer filter is preferably performed.
- the mesh of the polymer filter is preferably 100 ⁇ m or less, more preferably 30 ⁇ m or less.
- the step of collecting the resin pellet is naturally preferably a low dust environment, and more preferably a cleanness of class 1000 or less.
- the lens according to this embodiment can be obtained by molding the polycarbonate resin composition according to this embodiment.
- the manufacturing method of the lens of this embodiment includes the process of shape
- This step can be performed by an injection molding method such as an injection molding method or an injection compression molding method.
- the injection molding process can be performed under conventionally known conditions.
- the polycarbonate resin composition according to the present embodiment is excellent in moldability and can suppress contamination of the mold surface, so that a desired lens can be obtained with high yield by a manufacturing method including an injection molding process. A lens excellent in heat resistance and impact resistance can be obtained.
- the polycarbonate resin composition according to the present embodiment can use various additives in order to impart various characteristics within a range that does not impair the object of the present invention.
- Additives include antioxidants, processing heat stabilizers, mold release agents, UV absorbers, bluing agents, polymeric metal deactivators, flame retardants, lubricants, antistatic agents, heat ray shielding agents, fluorescent dyes (fluorescent dyes) Whitening agents), pigments, light scattering agents, reinforcing fillers, surfactants, antibacterial agents, plasticizers, compatibilizers and the like.
- antioxidants examples include triethylene glycol-bis [3- (3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate], 1,6-hexanediol-bis [3- (3,5 -Di-tert-butyl-4-hydroxyphenyl) propionate], pentaerythritol-tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], octadecyl-3- (3,5- Di-tert-butyl-4-hydroxyphenyl) propionate, 1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, N, N- Hexamethylenebis (3,5-di-tert-butyl-4-hydroxy-hydrocinnamide), 3,5-di tert-Butyl-4-hydroxy-benzylphosphonate-diethyl ester, tris
- processing heat stabilizer examples include a phosphorus processing heat stabilizer and a sulfur processing heat stabilizer.
- phosphorus processing heat stabilizer include phosphorous acid, phosphoric acid, phosphonous acid, phosphonic acid and esters thereof.
- triphenyl phosphite tris (nonylphenyl) phosphite, tris (2,4-di-tert-butylphenyl) phosphite, tris (2,6-di-tert-butylphenyl) phosphite, Tri n-decyl phosphite, tri n-octyl phosphite, tri n-octadecyl phosphite, di n-decyl monophenyl phosphite, di n-octyl monophenyl phosphite, diisopropyl monophenyl phosphite, mono n-
- sulfur-based processing heat stabilizer examples include pentaerythritol-tetrakis (3-laurylthiopropionate), pentaerythritol-tetrakis (3-myristylthiopropionate), pentaerythritol-tetrakis (3-stearylthiopropioate). Nate), dilauryl-3,3′-thiodipropionate, dimyristyl-3,3′-thiodipropionate, distearyl-3,3′-thiodipropionate, and the like.
- the content of the sulfur-based processing heat stabilizer in the polycarbonate resin composition is preferably 0.001 to 0.2 parts by mass with respect to 100 parts by mass of the polycarbonate resin.
- esters of alcohol and fatty acid include esters of monohydric alcohol and fatty acid, partial esters or total esters of polyhydric alcohol and fatty acid.
- the ester of the monohydric alcohol and the fatty acid is preferably an ester of a monohydric alcohol having 1 to 20 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms.
- the partial ester or total ester of the polyhydric alcohol and fatty acid is preferably a partial ester or total ester of a polyhydric alcohol having 1 to 25 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms.
- esters of monohydric alcohol and saturated fatty acid include stearyl stearate, palmityl palmitate, n-butyl stearate, methyl laurate, isopropyl palmitate and the like.
- partial ester or total ester of polyhydric alcohol and saturated fatty acid include stearic acid monoglyceride, stearic acid monoglyceride, stearic acid diglyceride, stearic acid triglyceride, stearic acid monosorbate, behenic acid monoglyceride, capric acid monoglyceride, lauric acid Monoglycerides, pentaerythritol monostearate, pentaerythritol tetrastearate, pentaerythritol tetrapelargonate, propylene glycol monostearate, biphenyl biphenate, sorbitan monostearate, 2-ethylhexyl stearate, dipentaeryth
- the content of these release agents is preferably in the range of 0.005 to 2.0 parts by weight, more preferably in the range of 0.01 to 0.6 parts by weight, with respect to 100 parts by weight of the polycarbonate resin.
- the range of 0.5 parts by mass is more preferable.
- a benzotriazole UV absorber in addition to the indole compound represented by the general formula (1), a benzotriazole UV absorber, a benzophenone UV absorber, a triazine UV absorber, a cyclic imino ester UV absorber, and a cyanoacrylate It can contain at least 1 sort (s) of ultraviolet absorbers chosen from the group which consists of a system ultraviolet absorber. Any of the ultraviolet absorbers listed below may be used alone or in combination of two or more.
- benzotriazole ultraviolet absorber examples include 2- (2-hydroxy-5-methylphenyl) benzotriazole, 2- (2-hydroxy-5-tert-octylphenyl) benzotriazole, 2- (2- Hydroxy-3,5-dicumylphenyl) phenylbenzotriazole, 2- (2-hydroxy-3-tert-butyl-5-methylphenyl) -5-chlorobenzotriazole, 2,2′-methylenebis [4- (1 , 1,3,3-tetramethylbutyl) -6- (2H-benzotriazol-2-yl) phenol], 2- (2-hydroxy-3,5-di-tert-butylphenyl) benzotriazole, -(2-hydroxy-3,5-di-tert-butylphenyl) -5-chlorobenzotriazole, 2- (2-hydroxy Droxy-3,5-di-tert-amylphenyl) benzotriazole, 2- (2-hydroxy-5-tert-o
- benzophenone ultraviolet absorber examples include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octyloxybenzophenone, 2-hydroxy-4-benzyloxybenzophenone, 2- Hydroxy-4-methoxy-5-sulfoxybenzophenone, 2-hydroxy-4-methoxy-5-sulfoxytrihydride benzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2 ', 4,4' -Tetrahydroxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy-5-sodiumsulfoxybenzophenone, bis (5-benzoyl-4- Hydroxy-2-methoxyphene Nyl) methane, 2-hydroxy-4-n-dodecyloxybenzophenone, 2-hydroxy-4-methoxy-2′-carboxybenzophenone and the like.
- triazine-based ultraviolet absorber examples include 2- (4,6-diphenyl-1,3,5-triazin-2-yl) -5-[(n-hexyl) oxy] -phenol, 2- (4, And 6-bis (2,4-dimethylphenyl) -1,3,5-triazin-2-yl) -5-[(n-octyl) oxy] -phenol.
- Examples of the cyclic imino ester ultraviolet absorber include 2,2′-bis (3,1-benzoxazin-4-one) and 2,2′-p-phenylenebis (3,1-benzoxazine-4-one). ON), 2,2′-m-phenylenebis (3,1-benzoxazin-4-one), 2,2 ′-(4,4′-diphenylene) bis (3,1-benzoxazin-4-one) ), 2,2 ′-(2,6-naphthalene) bis (3,1-benzoxazin-4-one), 2,2 ′-(1,5-naphthalene) bis (3,1-benzoxazine-4) -One), 2,2 '-(2-methyl-p-phenylene) bis (3,1-benzoxazin-4-one), 2,2'-(2-nitro-p-phenylene) bis (3 1-benzoxazin-4-one) and 2,2 ′-(2-chloro-p-pheny) Len) bis (3,1
- cyanoacrylate ultraviolet absorber examples include 1,3-bis-[(2′-cyano-3 ′, 3′-diphenylacryloyl) oxy] -2,2-bis [(2-cyano-3,3 -Diphenylacryloyl) oxy] methyl) propane, 1,3-bis-[(2-cyano-3,3-diphenylacryloyl) oxy] benzene and the like.
- the content of the ultraviolet absorber other than the indole compound (1) is preferably 0.01 to 1.0 part by weight, more preferably 0.02 to 0.8 part by weight with respect to 100 parts by weight of the polycarbonate resin. Part, more preferably 0.05 to 0.8 part by weight. If it is the range of this compounding quantity, it is possible to provide sufficient weather resistance to a polycarbonate resin composition according to a use.
- bluing agents include Bayer's Macrolex Violet B and Macrolex Blue RR, Clariant's Polysynthrene Blue RLS, Kiwa Chemical's K.K. P. Examples include Plast Violet 2R.
- the bluing agent is effective for eliminating the yellow color of the polycarbonate resin composition.
- the polycarbonate resin molded product tends to be yellowish due to the "action and color of the UV absorber".
- blending with a bluing agent is effective.
- the blending amount of the bluing agent is, for example, preferably 0.05 to 20 ppm, more preferably 0.1 to 15 ppm with respect to the polycarbonate resin.
- An ultraviolet / visible light absorbing spectacle lens can be obtained by using the lens of the present embodiment. If necessary, a coating layer may be provided on one side or both sides.
- the coating layer include a primer layer, a hard coat layer, an antireflection layer, an antifogging coat layer, a stain proof layer, and a water repellent layer.
- a primer layer a hard coat layer
- an antireflection layer an antifogging coat layer
- a stain proof layer a water repellent layer.
- Each of these coating layers can be used alone, or a plurality of coating layers can be used in multiple layers. When a coating layer is applied to both sides, a similar coating layer or a different coating layer may be applied to each surface.
- Each of these coating layers is a known ultraviolet absorber other than the indole compound represented by the general formula (1), an infrared absorber for the purpose of protecting the eyes from infrared rays, and a light stabilizer for the purpose of improving the weather resistance of the lens.
- dyes and pigments for the purpose of enhancing the fashionability of lenses, photochromic dyes, photochromic pigments, antistatic agents, and other known additives for enhancing lens performance may be used in combination.
- various leveling agents for the purpose of improving coating properties may be used for the layer to be coated by coating.
- the primer layer is usually formed between a hard coat layer, which will be described later, and the lens.
- the primer layer is a coating layer for the purpose of improving the adhesion between the hard coat layer formed thereon and the lens, and in some cases, the impact resistance can also be improved.
- Any material can be used for the primer layer as long as it has high adhesion to the obtained lens, but usually a primer mainly composed of urethane resin, epoxy resin, polyester resin, melamine resin, or polyvinyl acetal.
- a composition or the like is used.
- the primer composition may use an appropriate solvent that does not affect the lens for the purpose of adjusting the viscosity of the composition. Of course, you may use it without a solvent.
- the primer layer can be formed by either a coating method or a dry method.
- the primer layer is formed by solidifying after applying the primer composition to the lens by a known coating method such as spin coating or dip coating.
- a dry method it forms by well-known dry methods, such as CVD method and a vacuum evaporation method.
- the surface of the lens may be subjected to a pretreatment such as an alkali treatment, a plasma treatment, or an ultraviolet treatment as necessary for the purpose of improving adhesion.
- the hard coat layer is a coating layer for the purpose of imparting functions such as scratch resistance, abrasion resistance, moisture resistance, warm water resistance, heat resistance, and weather resistance to the lens surface.
- the hard coat layer is generally composed of an organic silicon compound having a curing property and an element selected from the element group of Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In, and Ti.
- a hard coat composition containing at least one kind of fine particles composed of one or more kinds of oxide fine particles and / or a composite oxide of two or more elements selected from these element groups is used.
- the hard coat composition includes at least amines, amino acids, metal acetylacetonate complexes, organic acid metal salts, perchloric acids, perchloric acid salts, acids, metal chlorides and polyfunctional epoxy compounds. It is preferable to include any of them.
- a suitable solvent that does not affect the lens may be used for the hard coat composition, or it may be used without a solvent.
- the hard coat layer is usually formed by applying a hard coat composition by a known coating method such as spin coating or dip coating and then curing.
- a known coating method such as spin coating or dip coating and then curing.
- the curing method include thermal curing, a curing method by irradiation with energy rays such as ultraviolet rays and visible rays, and the like.
- the refractive index of the hard coat layer is preferably in the range of ⁇ 0.1 in the difference in refractive index from the lens.
- the antireflection layer is usually formed on the hard coat layer as necessary.
- inorganic oxides such as SiO 2 and TiO 2 are used, and vacuum deposition, sputtering, ion plating, ion beam assist, and CVD are used. It is formed by the dry method.
- an organic type it is formed by a wet method using a composition containing an organosilicon compound and silica-based fine particles having internal cavities.
- the antireflection layer has a single layer and a multilayer, and when used in a single layer, the refractive index is preferably at least 0.1 lower than the refractive index of the hard coat layer.
- a multilayer antireflection film is preferably used. In that case, a low refractive index film and a high refractive index film are alternately laminated. Also in this case, the refractive index difference between the low refractive index film and the high refractive index film is preferably 0.1 or more.
- Examples of the high refractive index film include ZnO, TiO 2 , CeO 2 , Sb 2 O 5 , SnO 2 , ZrO 2 , and Ta 2 O 5, and examples of the low refractive index film include an SiO 2 film. .
- an antifogging layer, an antifouling layer and a water repellent layer may be formed as necessary.
- the processing method and processing materials are not particularly limited, and a known antifogging treatment is possible. Methods, antifouling treatment methods, water repellent treatment methods, and materials can be used.
- a method of covering the surface with a surfactant for example, a method of adding a hydrophilic film to the surface to make it water absorbent, a method of covering the surface with fine irregularities and increasing water absorption
- a method of covering the surface with fine irregularities and increasing water absorption examples thereof include a method of absorbing water by utilizing photocatalytic activity, and a method of preventing water droplet adhesion by applying a super water-repellent treatment.
- a method of forming a water repellent treatment layer by vapor deposition or sputtering of a fluorine-containing silane compound or the like, or a method of forming a water repellent treatment layer by coating after dissolving the fluorine-containing silane compound in a solvent Etc a method of forming a water repellent treatment layer by vapor deposition or sputtering of a fluorine-containing silane compound or the like, or a method of forming a water repellent treatment layer by coating after dissolving the fluorine-containing silane compound in a solvent Etc.
- the spectral transmittance of ultraviolet / visible light of 420 nm or less is preferably 0 to 20%, more preferably 0 to 15%, and further preferably 0 to 10%. It is. It is preferable that the spectral transmittance of ultraviolet / visible light is 20% or less because it is effective for preventing eye damage.
- the spectral transmittance at 450 nm, 550 nm, and 650 nm is preferably 50% or more, more preferably 60% or more, and more preferably 70% or more. Further preferred.
- the spectral transmittances of 450 nm, 550 nm, and 650 nm do not need to be 50% or more in all cases, and only the spectral transmittance of 450 nm is 50% or more, depending on the function desired.
- only the spectral transmittance at 550 nm may be 50% or more, and only the spectral transmittance at 650 nm may be 50% or more. Even if the spectral transmittance at two or more wavelengths selected from them is 50% or more, Good.
- the spectral transmittance at one or more wavelengths is 50% or more, more preferably the spectral transmittance at two or more wavelengths is 50% or more, and more preferably the spectral transmittance at the wavelengths of the three primary colors. 50% or more.
- the lens of the present embodiment preferably has a total light transmittance of 75% or more, more preferably a total light transmittance of 80% or more, and further preferably a total light transmittance of 85% or more. It is.
- a film or sheet can also be produced by a melt extrusion molding method.
- a resin melted by an extruder is extruded from a die into a film or a sheet, and is then brought into close contact with a cooling roll and solidified by cooling.
- the melt extrusion molding method can be performed under conventionally known conditions.
- Polycarbonate resin-1 Panlite L-1225, manufactured by Teijin Ltd., bisphenol A type polycarbonate having a weight average molecular weight of 43,000
- Polycarbonate resin-2 SD-2173M, weight average molecular weight manufactured by Sumika Polycarbonate Co., Ltd.
- UV absorber-A ethyl -2-Cyano-3- (1N-methyl-2-phenyl-1H-indol-3-yl) acrylate
- UV absorber-B (hereinafter sometimes abbreviated as UVA-B): 2- [ (1N-butyl-2-phenyl-1H-indol-3-yl) methylene] Rononitrile
- UV absorber-C (hereinafter sometimes abbreviated as UVA-C): ethyl-2-cyano-3- (1N-benzyl-2-phenyl-1H-indol-3-yl) acrylate
- UVA-D Ultraviolet absorber-D
- UVA-D benzyl-2-cyano-3- (1
- spectrophotometer Multispec manufactured by Shimadzu Corporation was used, and an ultraviolet / visible light spectrum was measured using a planar lens having a thickness of 2 mm.
- Y. I. Value measurement Measurement was performed with a color difference meter Cute-i manufactured by Suga Test Instruments Co., Ltd. using a planar lens having a thickness of 2 mm.
- Total light transmittance / Haze Measurement was performed in accordance with JIS K 7136 using NDH2000 manufactured by Nippon Denshoku Co., Ltd. using a planar lens having a thickness of 2 mm.
- the weight average molecular weight of the polycarbonate resin was measured as a value in terms of standard polystyrene by eluent chloroform using a Waters GPC system (pump: 1515, differential refractometer: 2414, column: Shodex K-806L).
- [Impact resistance test of molded lenses] A puncture impact test was conducted using a Plano lens having a thickness of 2 mm in accordance with JIS K 7211-2, and a ductile fracture sample was evaluated as “ ⁇ ”, and a brittle fracture sample was evaluated as “X”.
- Example 1 100 parts by weight of polycarbonate resin-1 and 0.035 parts by weight of UVA-A are fed to a twin-screw extruder with a vent (TEX30 ⁇ manufactured by Nippon Steel, Ltd., cylinder setting temperature 260 ° C.) by a quantitative feeder, and foreign matter is passed through a filter. After being filtered, it was discharged from the die in a strand form, cooled with water and solidified, and then pelletized with a rotary cutter to obtain a polycarbonate resin composition. Thereafter, the polycarbonate resin composition was dried in a clean oven at 120 ° C. for 5 hours. The polycarbonate resin composition was injection molded at a resin temperature of 280 ° C.
- Example 2 In Example 1, instead of using 0.035 parts by mass of UVA-A, a polycarbonate resin composition was produced according to the procedure described in Example 1, except that 0.021 parts by mass of UVA-A was used. A polycarbonate resin dried by a clean oven was injection molded to obtain a lens. Adherence of contaminants and the like was not observed on the mold of the injection molding machine. The optical characteristics of the obtained lens were measured and summarized in Table 1. This lens was not observed to be deposited on the surface even after being stored at room temperature for 3 months, and no change was observed in the surface condition.
- Example 3 In Example 1, instead of using 0.035 parts by mass of UVA-A, a polycarbonate resin composition was produced according to the procedure described in Example 1 except that 0.021 parts by mass of UVA-B was used. A polycarbonate resin dried by a clean oven was injection molded to obtain a lens. Adherence of contaminants and the like was not observed on the mold of the injection molding machine. The optical characteristics of the obtained lens were measured and summarized in Table 1. This lens was not observed to be deposited on the surface even after being stored at room temperature for 3 months, and no change was observed in the surface condition.
- Example 4 In Example 1, instead of using 0.035 parts by mass of UVA-A, a polycarbonate resin composition was produced according to the procedure described in Example 1, except that 0.020 parts by mass of UVA-C was used. A polycarbonate resin dried by a clean oven was injection molded to obtain a lens. Adherence of contaminants and the like was not observed on the mold of the injection molding machine. The optical characteristics of the obtained lens were measured and summarized in Table 1. This lens was not observed to be deposited on the surface even after being stored at room temperature for 3 months, and no change was observed in the surface condition.
- Example 5 In Example 1, instead of using 0.035 parts by mass of UVA-A, a polycarbonate resin composition was produced according to the procedure described in Example 1, except that 0.020 parts by mass of UVA-D was used. A polycarbonate resin dried by a clean oven was injection molded to obtain a lens. Adherence of contaminants and the like was not observed on the mold of the injection molding machine. The optical characteristics of the obtained lens were measured and summarized in Table 1. This lens was not observed to be deposited on the surface even after being stored at room temperature for 3 months, and no change was observed in the surface condition.
- Example 6 In Example 1, instead of using 0.035 parts by mass of UVA-A, a polycarbonate resin composition was produced according to the procedure described in Example 1, except that 0.75 parts by mass of UVA-A was used. A polycarbonate resin dried by a clean oven was injection molded to obtain a lens. Adherence of contaminants and the like was not observed on the mold of the injection molding machine. The optical characteristics of the obtained lens were measured and summarized in Table 1. This lens was not observed to be deposited on the surface even after being stored at room temperature for 3 months, and no change was observed in the surface condition.
- Example 7 In Example 1, instead of using 0.035 parts by mass of UVA-A, a polycarbonate resin composition was produced according to the procedure described in Example 1, except that 0.3 parts by mass of UVA-A was used. A polycarbonate resin dried by a clean oven was injection molded to obtain a lens. Adherence of contaminants and the like was not observed on the mold of the injection molding machine. The optical characteristics of the obtained lens were measured and summarized in Table 1. This lens was not observed to be deposited on the surface even after being stored at room temperature for 3 months, and no change was observed in the surface condition.
- Example 8 In Example 1, except that 100 parts by mass of polycarbonate resin-1 was used instead of 100 parts by mass of polycarbonate resin-1, a polycarbonate resin composition was produced in accordance with the procedure described in Example 1, and then a clean oven was used. The dried polycarbonate resin was injection molded to obtain a lens. Adherence of contaminants and the like was not observed on the mold of the injection molding machine. The optical characteristics of the obtained lens were measured and summarized in Table 1. This lens was not observed to be deposited on the surface even after being stored at room temperature for 3 months, and no change was observed in the surface condition.
- Example 9 In Example 1, instead of using 100 parts by weight of polycarbonate resin-1 and 0.035 parts by weight of UVA-A, 100 parts by weight of polycarbonate resin-2 and 0.020 parts by weight of UVA-A were used. A polycarbonate resin composition was produced according to the procedure described in Example 1, and then the polycarbonate resin dried by a clean oven was injection molded to obtain a lens. Adherence of contaminants and the like was not observed on the mold of the injection molding machine. The optical characteristics of the obtained lens were measured and summarized in Table 1. This lens was not observed to be deposited on the surface even after being stored at room temperature for 3 months, and no change was observed in the surface condition.
- the polycarbonate resin composition was injection molded at a resin temperature of 280 ° C. and a mold temperature of 90 ° C. using an injection molding machine (SE-180DU manufactured by Sumitomo Heavy Industries, Ltd.) to mold a lens having a diameter of 75 mm and a thickness of 2 mm. Adherence of fine powdery contaminants was observed on the mold of the injection molding machine.
- the spectral transmittance, total light transmittance, haze, and YI value of the obtained lens at 400 nm and 420 nm were measured and summarized in Table 1. This lens had a powdery substance deposited on its surface after storage for 3 months, and poor appearance was observed.
- the spectral transmittance, total light transmittance, haze, and YI value of the obtained lens at 400 nm and 420 nm were measured and summarized in Table 1.
- This lens had a powdery substance deposited on its surface after storage for 3 months, and poor appearance was observed.
- Example 10 Polycarbonate resin-1 100 parts by weight, UVA-A 0.035 parts by weight, processing heat stabilizer A 0.02 parts by weight and bluing agent A 10 ppm with a biaxial extruder equipped with a vent [Nippon Steel Co., Ltd. The product was supplied to TEX30 ⁇ manufactured in the factory, and the cylinder set temperature was 260 ° C., and foreign matter was filtered through a filter. The foreign matter was discharged from the die into strands, cooled with water, solidified, and pelletized with a rotary cutter to obtain a polycarbonate resin composition. Thereafter, the polycarbonate resin composition was dried in a clean oven at 120 ° C. for 5 hours.
- the polycarbonate resin composition was injection molded with an injection molding machine (SE-180DU manufactured by Sumitomo Heavy Industries Ltd.) at a resin temperature of 280 ° C. and a mold temperature of 90 ° C. to form a lens having a diameter of 75 mm and a thickness of 2 mm. Adherence of contaminants and the like was not observed on the mold of the injection molding machine.
- the optical characteristics of the obtained lens were measured and summarized in Table 1. This lens was not observed to be deposited on the surface even after being stored at room temperature for 3 months, and no change was observed in the surface condition.
- Example 11 100 parts by weight of polycarbonate resin-1, 0.025 parts by weight of UVA-A, 0.02 parts by weight of processing heat stabilizer A, 0.4 parts by weight of UVA-F and 10 ppm of bluing agent are biaxially attached with a vent by a quantitative feeder.
- Supply to an extruder TEX30 ⁇ manufactured by Nippon Steel Works, Cylinder Setting Temperature 260 ° C
- filter the foreign matter through the filter discharge it from the die into strands, cool with water, solidify, and pelletize with a rotary cutter
- a polycarbonate resin composition was obtained. Thereafter, the polycarbonate resin composition was dried in a clean oven at 120 ° C. for 5 hours.
- the polycarbonate resin composition was injection molded at a resin temperature of 280 ° C. and a mold temperature of 90 ° C. using an injection molding machine (SE-180DU manufactured by Sumitomo Heavy Industries, Ltd.) to mold a lens having a diameter of 75 mm and a thickness of 2 mm. Adherence of contaminants and the like was not observed on the mold of the injection molding machine.
- the optical characteristics of the obtained lens were measured and summarized in Table 1. This lens was not observed to be deposited on the surface even after being stored at room temperature for 3 months, and no change was observed in the surface condition.
- the lens according to the present invention sufficiently shields ultraviolet and visible light having wavelengths of 400 nm and 420 nm, while having high total light transmittance, excellent transparency and hue, and impact resistance. It was confirmed to be high. Furthermore, it was confirmed that mold contamination was suppressed. In addition, the lens of the present invention was excellent in storage stability with no change in the surface condition after aging.
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Abstract
Description
また、長い間、眼に青色光の照射を浴びることは、眼精疲労やストレスを受けることが懸念されており、加齢黄斑変性を引き起こす要因と考えられている。
さらにポリカーボネート樹脂は射出成型が可能なため、上記の注型レンズと比較して生産性が高い。
したがって、420nm以下の紫外・可視光線を抑制した全光線透過率の高い、さらには耐衝撃性の高いレンズが求められている。
本発明の第1の目的は、耐衝撃性、耐金型汚染性、透明性、色調安定性に優れ、かつ特定波長の紫外線のカット効果に優れており、紫外線による黄変が抑制されたポリカーボネート樹脂製レンズを提供することにある。
本発明の第2の目的は波長420nmの青色光のカット効果に優れ、当該青色光の眼への影響が軽減され、かつ全光線透過率が高いレンズを提供することにある。
本発明の第3の目的は、射出成型等の成型加工時において、紫外線吸収剤の昇華による金型表面の汚染が抑制されており、所望のレンズを歩留まりよく得ることができるポリカーボネート樹脂組成物および当該組成物を用いたレンズの製造方法を提供することにある。
すなわち、本発明は以下に示すことができる。
[1] 重量平均分子量40,000~60,000のポリカーボネート樹脂100質量部に対し、下記一般式(1)で表されるインドール系化合物を0.01~0.8質量部含むレンズ。
[2] 厚さ2mmにおいて、波長420nm以下の分光透過率が0~20%である、[1]に記載のレンズ。
[3] 厚さ2mmにおいて、波長420nm以下の分光透過率が0~20%であり、波長450nmの分光透過率が50%以上である、[1]または[2]に記載のレンズ。
[4] さらにブルーイング剤を含む、[1]~[3]のいずれかに記載のレンズ。
[5] さらに一般式(1)で表される前記インドール系化合物以外の紫外線吸収剤を含む、[1]~[4]のいずれかに記載のレンズ。
[6] さらに酸化防止剤および/または加工熱安定剤を含む、[1]~[5]のいずれかに記載のレンズ。
[7] 重量平均分子量40,000~60,000のポリカーボネート樹脂100質量部に対し、下記一般式(1)で表されるインドール系化合物を0.01~0.8質量部含む樹脂組成物。
[8] 重量平均分子量40,000~60,000のポリカーボネート樹脂100質量部に対し、下記一般式(1)で表されるインドール系化合物を0.01~0.8質量部含む樹脂組成物を射出成型により成型する工程を含む、レンズの製造方法。
さらに、本発明によれば、金型表面の汚染を抑制することができ、所望のレンズが歩留まりよく得られるポリカーボネート樹脂組成物および当該組成物を用いたレンズの製造方法を提供することができる。
本実施形態のレンズは、重量平均分子量40,000~60,000のポリカーボネート樹脂100質量部に対し、所定のインドール系化合物を0.01~0.8質量部含む。
ポリカーボネート樹脂は、二価フェノールとカーボネート前駆体を反応させて得られる芳香族ポリカーボネート樹脂である。
二価フェノールの具体例としては、例えば2,2-ビス(4-ヒドロキシフェニル)プロパン(通称ビスフェノールA)、ビス(4-ヒドロキシフェニル)メタン、1,1-ビス(4-ヒドロキシフェニル)エタン、2,2-ビス(4-ヒドロキシフェニル)ブタン、2,2-ビス(4-ヒドロキシフェニル)オクタン、2,2-ビス(4-ヒドロキシフェニル)フェニルエタン、2,2-ビス(4-ヒドロキシ-3-メチルフェニル)プロパン、1,1-ビス(4-ヒドロキシ-3-tert-ブチルフェニル)プロパン、2,2-ビス(4-ヒドロキシ-3-ブロモフェニル)プロパン、2,2-ビス(4-ヒドロキシ-3,5-ジブロモフェニル)プロパン、2,2-ビス(4-ヒドロキシ-3,5-ジクロロフェニル)プロパン等のビス(ヒドロキシアリール)アルカン類、1,1-ビス(ヒドロキシフェニル)シクロペンタン、1,1-ビス(ヒドロキシフェニル)シクロヘキサン等のビス(ヒドロキシフェニル)シクロアルカン類、4,4'-ジヒドロキシジフェニルエーテル、4,4'-ジヒドロキシ-3,3'-ジメチルジフェニルエーテル等のジヒドロキシアリールエーテル類、4,4'-ジヒドロキシジフェニルスルフィド、4,4'-ジヒドロキシ-3,3'-ジメチルジフェニルスルフィド等のジヒドロキシジアリールスルフィド類、4,4'-ジヒドロキシジフェニルスルホキシド、4,4'-ジヒドロキシ-3,3'-ジメチルジフェニルスルホキシド等のジヒドロキシジアリールスルホキシド類、4,4'-ジヒドロキシジフェニルスルホン、4,4'-ジヒドロキシ-3,3'-ジメチルジフェニルスルホン等のジヒドロキシジアリールスルホン類等を挙げることができる。これら二価フェノールは単独で用いても、二種以上併用してもよい。
本実施形態において、本発明の効果の観点から、ポリカーボネート樹脂はビスフェノールA型ポリカーボネートであることが好ましい。
カーボネート前駆体としてホスゲンを用いる溶液法では、通常酸結合剤および有機溶媒の存在下に二価フェノール成分とホスゲンとの反応を行う。酸結合剤としては例えば水酸化ナトリウムや水酸化カリウム等のアルカリ金属の水酸化物またはピリジン等のアミン化合物が用いられる。有機溶媒としては例えば塩化メチレン、クロロベンゼン等のハロゲン化炭化水素が用いられる。また反応促進のために例えば第三級アミンや第四級アンモニウム塩等の触媒を用いることができ、分子量調節剤として例えばフェノールやp-tert-ブチルフェノールのようなアルキル置換フェノール等の末端停止剤を用いることが望ましい。反応温度は通常0~40℃、反応時間は数分~5時間、反応中のpHは10以上に保つのが好ましい。
眼鏡レンズは精密成形であり、金型の鏡面を正確に転写して規定の曲率、度数を付与することが重要であり、溶融流動性のよい低粘度の樹脂が望ましいが、あまりに低粘度過ぎるとポリカーボネート樹脂の特徴である衝撃強度が保持できない。一方、粘度が高いとハンドリング性が低下し、レンズの生産性が低下する。したがって、ポリカーボネート樹脂の重量平均分子量が上記範囲であると、金型の転写性に優れるとともに、耐衝撃性にも優れ、さらにレンズの生産性にも優れる。
本実施形態において使用されるインドール系化合物は、下記一般式(1)で表される紫外線吸収剤である。
R3としては、例えば置換基を有してもよい炭素数1~20のアルキル基若しくはアラルキル基が挙げられる。R3の具体例としては、例えば上記R1で例示したもの及びβ-シアノエチル基、β-クロロエチル基、エトキシプロピル基、ヒドロキシアルキル基、アルコキシアルコキシアルキル基が挙げられる。
本実施形態においては、一般式(1)で表されるインドール系化合物は昇華性ではなく、ポリカーボネート樹脂の射出成形時において鏡面金型の汚染が抑制されるとともに、当該化合物を多量添加した場合でも鏡面金型の汚染が抑制される。さらに、当該インドール系化合物を含むレンズは、経時後においても表面状態に変化がなく保存安定性にも優れる。
一般式(3)中、R2は一般式(1)のR2と同義である。
すなわち、インドール系化合物(1)を上記の量で含むことにより、420nm以下の紫外・可視光線を効果的に遮光することができるとともに、色相および耐衝撃性に優れ、耐金型汚染性に特に優れる。
本実施形態のレンズの製造方法は、本実施形態の樹脂組成物を射出成型により成型する工程を含む。当該工程は、射出成形法および射出圧縮成形法等の射出成型方法により行うことができる。射出成型工程は従来公知の条件で行うことができる。
ポリカーボネート樹脂組成物中の酸化防止剤の含有量は、ポリカーボネート樹脂100質量部に対して0.001~0.3質量部であることが好ましい。
リン系加工熱安定剤としては、例えば、亜リン酸、リン酸、亜ホスホン酸、ホスホン酸およびこれらのエステル等が挙げられる。具体的には、トリフェニルホスファイト、トリス(ノニルフェニル)ホスファイト、トリス(2,4-ジ-tert-ブチルフェニル)ホスファイト、トリス(2,6-ジ-tert-ブチルフェニル)ホスファイト、トリn-デシルホスファイト、トリn-オクチルホスファイト、トリn-オクタデシルホスファイト、ジn-デシルモノフェニルホスファイト、ジn-オクチルモノフェニルホスファイト、ジイソプロピルモノフェニルホスファイト、モノn-ブチルジフェニルホスファイト、モノデシルジフェニルホスファイト、モノn-オクチルジフェニルホスファイト、ビス(2,6-ジ-tert-ブチル-4-メチルフェニル)ペンタエリスリトールジホスファイト、2,2-メチレンビス(4,6-ジ-tert-ブチルフェニル)オクチルホスファイト、ビス(n-ノニルフェニル)ペンタエリスリトールジホスファイト、ビス(2,4-ジクミルフェニル)ペンタエリスリトールジホスファイト、ビス(2,4-ジ-tert-ブチルフェニル)ペンタエリスリトールジホスファイト、ジステアリルペンタエリスリトールジホスファイト、トリn-ブチルホスフェート、トリエチルホスフェート、トリメチルホスフェート、トリフェニルホスフェート、ジフェニルモノオルソキセニルホスフェート、ジn-ブチルホスフェート、ジn-オクチルホスフェート、ジイソプロピルホスフェート、ベンゼンホスホン酸ジメチル、ベンゼンホスホン酸ジエチル、ベンゼンホスホン酸ジプロピル、テトラキス(2,4-ジ-t-ブチルフェニル)-4,4'-ビフェニレンジホスホナイト、テトラキス(2,4-ジ-t-ブチルフェニル)-4,3'-ビフェニレンジホスホナイト、テトラキス(2,4-ジ-t-ブチルフェニル)-3,3'-ビフェニレンジホスホナイト、ビス(2,4-ジ-tert-ブチルフェニル)-4-フェニル-フェニルホスホナイトおよびビス(2,4-ジ-tert-ブチルフェニル)-3-フェニル-フェニルホスホナイト等が挙げられる。
ポリカーボネート樹脂組成物中のリン系加工熱安定剤の含有量は、ポリカーボネート樹脂100質量部に対して0.001~0.2質量部が好ましい。
ポリカーボネート樹脂組成物中の硫黄系加工熱安定剤の含有量は、ポリカーボネート樹脂100質量部に対して0.001~0.2質量部が好ましい。
ブルーイング剤の配合量は、例えば、ポリカーボネート樹脂に対して、好ましくは0.05~20ppmであり、より好ましくは0.1~15ppmである。
ハードコート層は、レンズ表面に耐擦傷性、耐摩耗性、耐湿性、耐温水性、耐熱性、耐候性等機能を与えることを目的としたコーティング層である。
本実施形態のポリカーボネート樹脂組成物を用い、溶融押し出し成型法によりフィルムまたはシートを製造することもできる。溶融押し出し成型法は、押し出し機で溶融した樹脂をダイからフィルムまたはシート状に押し出し、次いで冷却ロールに密着させ冷却固化させて製造される。溶融押し出し成型法は従来公知の条件で行うことができる。
〔2〕ポリカーボネート樹脂-2:住化ポリカーボネート株式会社製 SD-2173M 重量平均分子量45,000のビスフェノールA型ポリカーボネート
〔3〕ポリカーボネート樹脂-3:重量平均分子量35,000のビスフェノールA型ポリカーボネート
〔4〕紫外線吸収剤-A(以下、UVA-Aと略記する場合がある):エチル-2-シアノ-3-(1N-メチル-2-フェニル-1H-インドール-3-イル)アクリレート
〔5〕紫外線吸収剤-B(以下、UVA-Bと略記する場合がある):2-〔(1N-ブチル-2-フェニル-1H-インドール-3-イル)メチレン〕マロノニトリル
〔6〕紫外線吸収剤-C(以下、UVA-Cと略記する場合がある):エチル-2-シアノ-3-(1N-ベンジル-2-フェニル-1H-インドール-3-イル)アクリレート
〔7〕紫外線吸収剤-D(以下、UVA-Dと略記する場合がある):ベンジル-2-シアノ-3-(1N-メチル-2-フェニル-1H-インドール-3-イル)アクリレート
〔8〕紫外線吸収剤-E(以下、UVA-Eと略記する場合がある):2-(3-tert-ブチル-5-メチル-2-ヒドロキシフェニル)-5-クロロベンゾトリアゾール
〔9〕紫外線吸収剤-F(以下、UVA-Fと略記する場合がある):2,2’-メチレンビス〔4-(1,1,3,3-テトラメチルブチル)-6-(2H-ベンゾトリアゾール-2-イル)フェノール〕
〔10〕加工熱安定剤A:テトラキス(2,4-ジ-t-ブチルフェニル)-4,4’-ビフェニレンジホスホナイト:〔Hostanox P-EPQ〕
〔11〕ブルーイング剤A:1-ヒドロキシ-4-(p-トリルアミノ)アントラセン-9,10-ジオン〔マクロレックスバイオレットB〕
測定機器として、(株)島津製作所社製、分光光度計 Multispecを使用し、2mm厚のプラノーレンズを用いて紫外・可視光スペクトルを測定した。
〔Y.I.値の測定〕
2mm厚のプラノーレンズを用いてスガ試験機株式会社製色彩色差計Cute-iにて測定した。
〔全光線透過率・Haze〕
2mm厚のプラノーレンズを用いて日本電色株式会社製NDH2000にてJIS K 7136に準拠して測定した。
Waters社製GPCシステム〔ポンプ:1515、示差屈折率計:2414、カラム:Shodex K-806L〕を使用して溶出液クロロホルムにより標準ポリスチレン換算の値として、ポリカーボネート樹脂の重量平均分子量を測定した。
〔レンズ成型品の耐衝撃試験〕
2mm厚のプラノーレンズを用いてJIS K 7211-2に準拠し、パンクチャー衝撃試験を行い延性破壊のサンプルを○、脆性破壊のサンプルを×として評価した。
ポリカーボネート樹脂-1を100質量部およびUVA-A 0.035質量部を定量フィーダーによりベント付き2軸押し出し機〔(株)日本製鋼所製TEX30α、シリンダー設定温度260℃〕に供給し、フィルターを通して異物をろ過した後、ダイからストランド状に排出し、水冷、固化させた後回転式カッターでペレット化しポリカーボネート樹脂組成物を得た。その後、該ポリカーボネート樹脂組成物をクリーンオーブンにて120℃で5時間乾燥させた。
該ポリカーボネート樹脂組成物を射出成型機〔住友重工業株式会社製 SE-180DU〕にて樹脂温度280℃、金型温度90℃で射出成型し、直径75mm、厚さ2mmのレンズを成型した。射出成型機の金型には汚染物質等の付着は認められなかった。得られたレンズの400nmおよび420nmの分光透過率、全光線透過率、Haze、YI値を測定し、表1にまとめた。このレンズは室温にて3か月保管した後も表面に物質の析出等が認められず、表面の状態に変化は認められなかった。
実施例1において、UVA-Aを0.035質量部使用する代わりに、UVA-Aを0.021質量部使用した以外は、実施例1に記載の操作に従いポリカーボネート樹脂組成物を製造し、その後クリーンオーブンにより乾燥したポリカーボネート樹脂を射出成型し、レンズを得た。射出成型機の金型には汚染物質等の付着は認められなかった。得られたレンズの光学特性を測定し、表1にまとめた。このレンズは室温にて3か月保管した後も表面に物質の析出等が認められず、表面の状態に変化は認められなかった。
実施例1において、UVA-Aを0.035質量部使用する代わりに、UVA-Bを0.021質量部使用した以外は、実施例1に記載の操作に従いポリカーボネート樹脂組成物を製造し、その後クリーンオーブンにより乾燥したポリカーボネート樹脂を射出成型し、レンズを得た。射出成型機の金型には汚染物質等の付着は認められなかった。得られたレンズの光学特性を測定し、表1にまとめた。このレンズは室温にて3か月保管した後も表面に物質の析出等が認められず、表面の状態に変化は認められなかった。
実施例1において、UVA-Aを0.035質量部使用する代わりに、UVA-Cを0.020質量部使用した以外は、実施例1に記載の操作に従いポリカーボネート樹脂組成物を製造し、その後クリーンオーブンにより乾燥したポリカーボネート樹脂を射出成型し、レンズを得た。射出成型機の金型には汚染物質等の付着は認められなかった。得られたレンズの光学特性を測定し、表1にまとめた。このレンズは室温にて3か月保管した後も表面に物質の析出等が認められず、表面の状態に変化は認められなかった。
実施例1において、UVA-Aを0.035質量部使用する代わりに、UVA-Dを0.020質量部使用した以外は、実施例1に記載の操作に従いポリカーボネート樹脂組成物を製造し、その後クリーンオーブンにより乾燥したポリカーボネート樹脂を射出成型し、レンズを得た。射出成型機の金型には汚染物質等の付着は認められなかった。得られたレンズの光学特性を測定し、表1にまとめた。このレンズは室温にて3か月保管した後も表面に物質の析出等が認められず、表面の状態に変化は認められなかった。
実施例1において、UVA-Aを0.035質量部使用する代わりに、UVA-Aを0.75質量部使用した以外は、実施例1に記載の操作に従いポリカーボネート樹脂組成物を製造し、その後クリーンオーブンにより乾燥したポリカーボネート樹脂を射出成型し、レンズを得た。射出成型機の金型には汚染物質等の付着は認められなかった。得られたレンズの光学特性を測定し、表1にまとめた。このレンズは室温にて3か月保管した後も表面に物質の析出等が認められず、表面の状態に変化は認められなかった。
実施例1において、UVA-Aを0.035質量部使用する代わりに、UVA-Aを0.3質量部使用した以外は、実施例1に記載の操作に従いポリカーボネート樹脂組成物を製造し、その後クリーンオーブンにより乾燥したポリカーボネート樹脂を射出成型し、レンズを得た。射出成型機の金型には汚染物質等の付着は認められなかった。得られたレンズの光学特性を測定し、表1にまとめた。このレンズは室温にて3か月保管した後も表面に物質の析出等が認められず、表面の状態に変化は認められなかった。
実施例1において、ポリカーボネート樹脂-1を100質量部使用する代わりにポリカーボネート樹脂-2を100質量部使用した以外は、実施例1に記載の操作に従いポリカーボネート樹脂組成物を製造し、その後クリーンオーブンにより乾燥したポリカーボネート樹脂を射出成型し、レンズを得た。射出成型機の金型には汚染物質等の付着は認められなかった。得られたレンズの光学特性を測定し、表1にまとめた。このレンズは室温にて3か月保管した後も表面に物質の析出等が認められず、表面の状態に変化は認められなかった。
実施例1において、ポリカーボネート樹脂-1を100質量部およびUVA-Aを0.035質量部使用する代わりにポリカーボネート樹脂-2を100質量部およびUVA-Aを0.020質量部使用した以外は、実施例1に記載の操作に従いポリカーボネート樹脂組成物を製造し、その後クリーンオーブンにより乾燥したポリカーボネート樹脂を射出成型し、レンズを得た。射出成型機の金型には汚染物質等の付着は認められなかった。得られたレンズの光学特性を測定し、表1にまとめた。このレンズは室温にて3か月保管した後も表面に物質の析出等が認められず、表面の状態に変化は認められなかった。
ポリカーボネート樹脂-1を100質量部、UVA-E 0.6質量部および加工熱安定剤A 0.02質量部を定量フィーダーによりベント付き2軸押し出し機〔(株)日本製鋼所製TEX30α、シリンダー設定温度260℃〕に供給し、フィルターを通して異物をろ過した後、ダイからストランド状に排出し、水冷、固化させた後回転式カッターでペレット化しポリカーボネート樹脂組成物を得た。その後、該ポリカーボネート樹脂組成物をクリーンオーブンにて120℃で5時間乾燥させた。
該ポリカーボネート樹脂組成物を射出成型機〔住友重工業株式会社製 SE-180DU〕にて樹脂温度280℃、金型温度90℃で射出成型し、直径75mm、厚さ2mmのレンズを成型した。射出成型機の金型に微粉状の汚染物質の付着が認められた。得られたレンズの400nmおよび420nmの分光透過率、全光線透過率、Haze、YI値を測定し、表1にまとめた。このレンズは3か月保管後表面に粉状の物質が析出しており、外観不良が観察された。
ポリカーボネート樹脂-3を100質量部およびUVA-A 0.020質量部を定量フィーダーによりベント付き2軸押し出し機〔(株)日本製鋼所製TEX30α、シリンダー設定温度260℃〕に供給し、フィルターを通して異物をろ過した後、ダイからストランド状に排出し、水冷、固化させた後回転式カッターでペレット化しポリカーボネート樹脂組成物を得た。その後、該ポリカーボネート樹脂組成物をクリーンオーブンにて120℃で5時間乾燥させた。
該ポリカーボネート樹脂組成物を射出成型機〔住友重工業株式会社製 SE-180DU〕にて樹脂温度280℃、金型温度90℃で射出成型し、直径75mm、厚さ2mmのレンズを成型した。射出成型機の金型には汚染物質等の付着は認められなかった。
得られたレンズの400nmおよび420nmの分光透過率、全光線透過率、Haze、YI値を測定し、表1にまとめた。このレンズは室温にて3か月保管した後も表面に物質の析出等が認められず、表面の状態に変化は認められなかった。
ポリカーボネート樹脂-1を100質量部およびUVA-F 7.5質量部を定量フィーダーによりベント付き2軸押し出し機〔(株)日本製鋼所製TEX30α、シリンダー設定温度260℃〕に供給し、フィルターを通して異物をろ過した後、ダイからストランド状に排出し、水冷、固化させた後回転式カッターでペレット化しポリカーボネート樹脂組成物を得た。その後、該ポリカーボネート樹脂組成物をクリーンオーブンにて120℃で5時間乾燥させた。
該ポリカーボネート樹脂組成物を射出成型機〔住友重工業株式会社製 SE-180DU〕にて樹脂温度280℃、金型温度90℃で射出成型し、直径75mm、厚さ2mmのレンズを成型した。射出成型機の金型に微粉状の汚染物質の付着が認められた。
得られたレンズの400nmおよび420nmの分光透過率、全光線透過率、Haze、YI値を測定し、表1にまとめた。このレンズは3か月保管後表面に粉状の物質が析出しており、外観不良が観察された。
ジエチレングリコールビスアリルカーボネートに重合開始剤IPP(ジイソプロピルパーオキシジカーボネート)3%を添加したもの100質量部に対してUVA-A 1.5質量部を配合し、これらを混合撹拌した後、真空脱気して液状の成型材料を調製した。この液状成型材料を凸面および凹面のガラスモールドにガスケットをセットして厚さが2mmとなるようにしたレンズ成型キャビティ内に注入した。成形材料は40℃で3時間、40~50℃の昇温を7時間、50℃~80℃の昇温を9時間さらに80℃で1時間加熱し、冷却してから取り出し、100℃で2時間アニーリングし、レンズを得た。得られたレンズの400nmおよび420nmの分光透過率、全光線透過率、Haze、YI値を測定し、表1にまとめた。このレンズは3か月保管後表面に粉状の物質が析出しており、外観不良が観察された。
ポリカーボネート樹脂-1を100質量部、UVA-A 0.035質量部、加工熱安定剤A 0.02質量部およびブルーイング剤A 10ppmを定量フィーダーによりベント付き2軸押し出し機〔(株)日本製鋼所製TEX30α、シリンダー設定温度260℃〕に供給し、フィルターを通して異物をろ過した後、ダイからストランド状に排出し、水冷、固化させた後回転式カッターでペレット化しポリカーボネート樹脂組成物を得た。その後、該ポリカーボネート樹脂組成物をクリーンオーブンにて120℃で5時間乾燥させた。
該ポリカーボネート樹脂組成物を射出成型機〔住友重工業株式製 SE-180DU〕にて樹脂温度280℃、金型温度90℃で射出成型し、直径75mm、厚さ2mmのレンズを成型した。射出成型機の金型には汚染物質等の付着は認められなかった。
得られたレンズの光学特性を測定し、表1にまとめた。このレンズは室温にて3か月保管した後も表面に物質の析出等が認められず、表面の状態に変化は認められなかった。
ポリカーボネート樹脂-1を100質量部、UVA-A 0.025質量部、加工熱安定剤A 0.02質量部、UVA-F 0.4質量部およびブルーイング剤10ppmを定量フィーダーによりベント付き2軸押し出し機〔(株)日本製鋼所製TEX30α、シリンダー設定温度260℃〕に供給し、フィルターを通して異物をろ過した後、ダイからストランド状に排出し、水冷、固化させた後回転式カッターでペレット化しポリカーボネート樹脂組成物を得た。その後、該ポリカーボネート樹脂組成物をクリーンオーブンにて120℃で5時間乾燥させた。
該ポリカーボネート樹脂組成物を射出成型機〔住友重工業株式会社製 SE-180DU〕にて樹脂温度280℃、金型温度90℃で射出成型し、直径75mm、厚さ2mmのレンズを成型した。射出成型機の金型には汚染物質等の付着は認められなかった。
得られたレンズの光学特性を測定し、表1にまとめた。このレンズは室温にて3か月保管した後も表面に物質の析出等が認められず、表面の状態に変化は認められなかった。
Claims (8)
- 厚さ2mmにおいて、波長420nm以下の分光透過率が0~20%である、請求項1に記載のレンズ。
- 厚さ2mmにおいて、波長420nm以下の分光透過率が0~20%であり、波長450nmの分光透過率が50%以上である、請求項1または2に記載のレンズ。
- さらにブルーイング剤を含む、請求項1~3のいずれかに記載のレンズ。
- さらに一般式(1)で表される前記インドール系化合物以外の紫外線吸収剤を含む、請求項1~4のいずれかに記載のレンズ。
- さらに酸化防止剤および/または加工熱安定剤を含む、請求項1~5のいずれかに記載のレンズ。
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JPWO2020250802A1 (ja) * | 2019-06-10 | 2020-12-17 | ||
JP2022517673A (ja) * | 2019-01-28 | 2022-03-09 | コーロン インダストリーズ インク | 発光素子用紫外線吸収封止材及びこれを含む発光素子 |
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Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04134065A (ja) * | 1990-09-25 | 1992-05-07 | Orient Chem Ind Ltd | インドール系化合物およびその用途 |
JPH04292661A (ja) * | 1991-03-19 | 1992-10-16 | Teijin Chem Ltd | 樹脂組成物 |
JPH05212103A (ja) | 1992-02-06 | 1993-08-24 | Tokyo Keikaku:Kk | 医療用レンズ |
JPH06161128A (ja) * | 1992-11-17 | 1994-06-07 | Mita Ind Co Ltd | 電子写真感光体 |
JPH09263694A (ja) | 1996-01-26 | 1997-10-07 | Teijin Chem Ltd | 眼鏡レンズ |
JP2000206323A (ja) * | 1998-11-11 | 2000-07-28 | Nisshinbo Ind Inc | 近赤外吸収フィルタ― |
JP2004325511A (ja) | 2003-04-21 | 2004-11-18 | Sumitomo Dow Ltd | 眼鏡レンズ |
JP2004352829A (ja) | 2003-05-28 | 2004-12-16 | Mitsubishi Engineering Plastics Corp | メガネレンズ用芳香族ポリカーボネート樹脂組成物 |
JP2004352828A (ja) | 2003-05-28 | 2004-12-16 | Mitsubishi Engineering Plastics Corp | メガネレンズ用芳香族ポリカーボネート樹脂組成物 |
JP2006241410A (ja) * | 2005-03-07 | 2006-09-14 | Nippon Zeon Co Ltd | 熱可塑性樹脂組成物及び用途 |
JP2012058643A (ja) | 2010-09-13 | 2012-03-22 | Talex Optical Co Ltd | 保護眼鏡用遮光レンズ |
JP2012206305A (ja) * | 2011-03-29 | 2012-10-25 | Teijin Chem Ltd | 樹脂積層体 |
JP2013054275A (ja) * | 2011-09-06 | 2013-03-21 | Nikon-Essilor Co Ltd | 染色レンズおよびその製造方法 |
WO2014002864A1 (ja) * | 2012-06-25 | 2014-01-03 | Jsr株式会社 | 固体撮像素子用光学フィルターおよびその用途 |
JP2015189933A (ja) * | 2014-03-28 | 2015-11-02 | 住友金属鉱山株式会社 | 熱線遮蔽樹脂シート材および自動車、建造物 |
JP2017014402A (ja) * | 2015-07-01 | 2017-01-19 | 大阪ガスケミカル株式会社 | フルオレンオリゴマー及びそれからなる樹脂用添加剤 |
JP2017099723A (ja) | 2015-12-02 | 2017-06-08 | 三星電子株式会社Samsung Electronics Co.,Ltd. | ドラム式洗濯機 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0786675B1 (en) * | 1996-01-26 | 2002-11-06 | Teijin Chemicals, Ltd. | Spectacle lens |
CA2289335A1 (en) | 1998-11-11 | 2000-05-11 | Nisshinbo Industries, Inc. | Near infrared absorption filter |
WO2011132510A1 (ja) * | 2010-04-20 | 2011-10-27 | 三菱瓦斯化学株式会社 | 透明難燃性の芳香族ポリカーボネート樹脂組成物及び成形品 |
WO2014163119A1 (ja) | 2013-04-03 | 2014-10-09 | 住友金属鉱山株式会社 | 熱線遮蔽膜、熱線遮蔽合わせ透明基材、熱線遮蔽樹脂シート材、自動車および建造物 |
WO2015166951A1 (ja) * | 2014-05-02 | 2015-11-05 | 三菱瓦斯化学株式会社 | ポリカーボネート樹脂組成物、ならびにそれを用いた光学材料および光学レンズ |
-
2018
- 2018-05-18 WO PCT/JP2018/019364 patent/WO2018212343A1/ja active Application Filing
- 2018-05-18 US US16/614,631 patent/US11630241B2/en active Active
- 2018-05-18 CN CN201880031397.7A patent/CN110622044A/zh active Pending
- 2018-05-18 JP JP2019518895A patent/JP6918102B2/ja active Active
- 2018-05-18 EP EP18803000.1A patent/EP3627193A4/en not_active Withdrawn
Patent Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04134065A (ja) * | 1990-09-25 | 1992-05-07 | Orient Chem Ind Ltd | インドール系化合物およびその用途 |
JPH04292661A (ja) * | 1991-03-19 | 1992-10-16 | Teijin Chem Ltd | 樹脂組成物 |
JPH05212103A (ja) | 1992-02-06 | 1993-08-24 | Tokyo Keikaku:Kk | 医療用レンズ |
JPH06161128A (ja) * | 1992-11-17 | 1994-06-07 | Mita Ind Co Ltd | 電子写真感光体 |
JPH09263694A (ja) | 1996-01-26 | 1997-10-07 | Teijin Chem Ltd | 眼鏡レンズ |
JP2000206323A (ja) * | 1998-11-11 | 2000-07-28 | Nisshinbo Ind Inc | 近赤外吸収フィルタ― |
JP2004325511A (ja) | 2003-04-21 | 2004-11-18 | Sumitomo Dow Ltd | 眼鏡レンズ |
JP2004352829A (ja) | 2003-05-28 | 2004-12-16 | Mitsubishi Engineering Plastics Corp | メガネレンズ用芳香族ポリカーボネート樹脂組成物 |
JP2004352828A (ja) | 2003-05-28 | 2004-12-16 | Mitsubishi Engineering Plastics Corp | メガネレンズ用芳香族ポリカーボネート樹脂組成物 |
JP2006241410A (ja) * | 2005-03-07 | 2006-09-14 | Nippon Zeon Co Ltd | 熱可塑性樹脂組成物及び用途 |
JP2012058643A (ja) | 2010-09-13 | 2012-03-22 | Talex Optical Co Ltd | 保護眼鏡用遮光レンズ |
JP2012206305A (ja) * | 2011-03-29 | 2012-10-25 | Teijin Chem Ltd | 樹脂積層体 |
JP2013054275A (ja) * | 2011-09-06 | 2013-03-21 | Nikon-Essilor Co Ltd | 染色レンズおよびその製造方法 |
WO2014002864A1 (ja) * | 2012-06-25 | 2014-01-03 | Jsr株式会社 | 固体撮像素子用光学フィルターおよびその用途 |
JP2015189933A (ja) * | 2014-03-28 | 2015-11-02 | 住友金属鉱山株式会社 | 熱線遮蔽樹脂シート材および自動車、建造物 |
JP2017014402A (ja) * | 2015-07-01 | 2017-01-19 | 大阪ガスケミカル株式会社 | フルオレンオリゴマー及びそれからなる樹脂用添加剤 |
JP2017099723A (ja) | 2015-12-02 | 2017-06-08 | 三星電子株式会社Samsung Electronics Co.,Ltd. | ドラム式洗濯機 |
Non-Patent Citations (2)
Title |
---|
See also references of EP3627193A4 |
THE EUROPEAN JOURNAL OF EUROSCIENCE, vol. 34, no. 4, 2011, pages 548 - 558 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2022517673A (ja) * | 2019-01-28 | 2022-03-09 | コーロン インダストリーズ インク | 発光素子用紫外線吸収封止材及びこれを含む発光素子 |
JP7232340B2 (ja) | 2019-01-28 | 2023-03-02 | コーロン インダストリーズ インク | 発光素子用紫外線吸収封止材及びこれを含む発光素子 |
JPWO2020250802A1 (ja) * | 2019-06-10 | 2020-12-17 | ||
WO2020250802A1 (ja) * | 2019-06-10 | 2020-12-17 | 三井化学株式会社 | 眼用保護部材、眼の保護方法及び光硬化物の製造方法 |
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CN110622044A (zh) | 2019-12-27 |
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