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WO2019057730A1 - Résine de polycarbonate ayant une action anti-lumière bleue et une couleur neutre améliorées - Google Patents

Résine de polycarbonate ayant une action anti-lumière bleue et une couleur neutre améliorées Download PDF

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Publication number
WO2019057730A1
WO2019057730A1 PCT/EP2018/075245 EP2018075245W WO2019057730A1 WO 2019057730 A1 WO2019057730 A1 WO 2019057730A1 EP 2018075245 W EP2018075245 W EP 2018075245W WO 2019057730 A1 WO2019057730 A1 WO 2019057730A1
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WO
WIPO (PCT)
Prior art keywords
resin mixture
color
colorant
absorber
colorant additive
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2018/075245
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English (en)
Inventor
Elliot FRENCH
Haifeng Shan
Hao-Wen Chiu
Aref Jallouli
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EssilorLuxottica SA
Original Assignee
Essilor International Compagnie Generale dOptique SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from PCT/EP2017/073812 external-priority patent/WO2018054994A1/fr
Application filed by Essilor International Compagnie Generale dOptique SA filed Critical Essilor International Compagnie Generale dOptique SA
Publication of WO2019057730A1 publication Critical patent/WO2019057730A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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
    • C08K5/16—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
    • 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
    • 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

Definitions

  • the invention relates to the field of ophthalmic lenses with blue-light blocking capabilities.
  • Blue light is a higher-energy component than the rest of the visible light spectrum. Studies suggest that, over time, exposure to the blue end of the light spectrum could cause serious long- term damage to your eyes. In order to prevent blue light-related health issues, ophthalmic lens manufacturers have developed methods to reduce trans mittance of blue light through ophthalmic lenses.
  • One approach for limiting the passage of blue light through the lens and into the eye is to add blue-cut and UV-absorbing filters to ophthalmic lenses.
  • the addition of blue light and UV absorbing dyes to ophthalmic lenses increases the yellowness index (YI) of the material.
  • coloring agents dyes must be added to the lens.
  • Spectacle lenses of various prescription powers create a lens with a variation in thickness from center to edge. This variation in thickness makes it difficult to select colorants that provide uniform, neutral color from lens center to edge (this is referred to as color homogeneity).
  • lens-forming processes such as injection molding
  • a polymeric resin material is subjected to elevated temperature and pressure conditions.
  • the elevated temperatures may cause degradation of some colorants, which in turn adversely affects lens color and homogeneity.
  • lens resin color additives that offset yellow tinting, provide color homogeneity, and withstand lens-processing conditions.
  • the color additives and color formulations disclosed herein are selected to offset or reduce yellowness index of blue-cut lenses.
  • a color formulation is selected to provide color neutrality and color homogeneity for blue-cut lenses.
  • the color formulation may provide color neutrality and color homogeneity for spectacle lenses of different prescription powers.
  • a color formulation is optimized provide color balance and color neutrality for prescription lenses of varying prescription powers.
  • the color formulations disclosed herein comprise a combination of two colorants.
  • the two colorants are provided in a ratio that bestows neutral color and/or color homogeneity to an optical article.
  • the two colorants are selected to provide lenses with a range of homogeneous colors that meet customer preferences.
  • the color formulations are compatible with polycarbonate resins, lens-forming processes, and downstream coating processes.
  • the amount of each color additive concentration is selected to meet the color and transmission shift commonly encountered with anti-reflective coatings.
  • the resin mixture is configured to homogenize a color appearance of the resulting lenses in such a manner that ⁇ ⁇ 5.5 , where ⁇ is the color difference between the lens center and the lens edge calculated using the CIE76 color-difference formula.
  • the resulting lenses have a diopter power > +0.75 or ⁇ -0.75.
  • Lens forming processes involve resins and color additives to be subjected to elevated temperatures.
  • the color additives' thermal stabilities are taken into consideration when selecting color additives for a color formulation.
  • the color additives' photostabilities are take into consideration when selecting color additives for a color formulation.
  • Optical articles comprising the presently disclosed color formulations are intended to provide health benefits to consumers in the form of blue light protection.
  • resin formulations comprising the presently disclosed color formulations may be implemented on a mass production scale to produce thermoplastic semi-finished and finished lenses.
  • a UV and blue light-blocking resin mixture for producing color-homogeneous UV and blue light-blocking lenses comprises a polycarbonate resin, a UV absorber, and at least one colorant additive.
  • the UV absorber and the at least one colorant additive are different compounds.
  • the resin mixture further comprises a second colorant additive.
  • the polycarbonate resin comprises at least one prior to adding the resin to the resin mixture. In additional embodiments, at least one additional or supplementary UV absorber is added to the resin mixture.
  • the polycarbonate resin comprises a polycarbonate polymer with a weight average molecular weight ranging from about 20,000 to about 40,000 g/mol.
  • a UV absorber has a maximum cut in the 315-400nm light wavelength range and partially blocks blue light in the 400-500 nm range. Therefore, in some aspects, UV and blue light-blocking resin mixture for producing color-homogeneous UV and blue light-blocking lenses comprises a polycarbonate resin, which may already include a UV absorber, at least one colorant additive, and a UV absorber.
  • the resin is Teijin Panlige L-1250VX, Bayer Makrolon LQ3187, or Sabic Lexan OQ4120, OQ4320, OQ4320R, OQ4620, or OQ4620R, or other resin known to those of skill in the art.
  • UV absorbers are frequently incorporated in optical articles in order to reduce or prevent UV light from reaching the retina (in particular in ophthalmic lens materials).
  • UV absorbers protect the substrate material from UV light, thus preventing it from weathering and becoming brittle and/or yellow.
  • the UV absorber preferably has the ability to at least partially block light having a wavelength shorter than 400 nm, preferably UV wavelengths below 385 or 390 nm, but also has an absorption spectrum extending to the visible blue light range (400 - 500 nm).
  • Most preferred ultraviolet absorbers have a maximum absorption peak in a range from 350 nm to 370 nm and/or do not absorb light in the 465-495 nm range, preferably the 450-550 nm range.
  • the UV absorber is a benzotriazole absorber.
  • Suitable UV absorbers include without limitation 2-(2-hydroxyphenyl)-benzotriazoles such as 2-(2-hydroxy-3-t-butyl-5- methylphenyl) chlorobenzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl) benzotriazole, 2-(3'- methallyl-2'-hydroxy-5 '-methyl phenyl) benzotriazole or other allyl hydro xymethylphenyl benzotriazoles, 2-(3,5-di-t-amyl-2-hydroxyphenyl) benzotriazole, and the 2-hydroxy-5- acryloxyphenyl-2H-benzotriazoles disclosed in U.S.
  • Preferred absorbers are of the benzotriazole family.
  • Commercially available products include Tinuvin 326 from BASF, Seeseorb 703 from Cipro, Viosorb 550 from Kyodo Chemicals, and Kemisorb 73 from Chemipro, Tinuvin®CarboProtect®.
  • the UV absorber is 2-(5-chloro-2H-benzotriazole- 2-yl)-6-(l ,l -dimethylethyl)-4-methyl phenol, also known as Tinuvin 326.
  • a resin mixture or color formulation comprises at least one colorant additive.
  • a resin mixture or color formulation comprises at least two colorant additives.
  • Suitable colorant additives can be selected from azo dyes, polymethyne dyes, arylmethyne dyes, polyene dyes, anthracinedione dyes, pyrazolone dyes, anthraquinone dyes, auinophtalone dyes, and carbonyl dyes.
  • at least one of the first and second colorant additives is an anthraquinone dye.
  • the first colorant additive and the second colorant additives are anthraquinone dyes.
  • the at least one colorant additive is 3H-naphtho[l ,2,3-de]quinoline-2,7-dione,3-methyl-6-[(4-methylphenyl)amino], also known as Solvent Red 52.
  • the second colorant additive is 9,10-anthracenedione, 1,4- bis[(2,4,6-trimethylphenyl) amino], also known as Solvent Blue 104.
  • one of the first or second colorant additives is one of solvent violet 36, solvent violet 13, solvent violet 11 , solvent violet 37, solvent violet 50, solvent blue 138, solvent blue 45, or solvent red 169.
  • the resin mixture comprises a UV absorber in an amount ranging from 0.1 to 2.0 weight percent of the resin mixture.
  • the first colorant additive is present in an amount ranging from 0.1 to 3.0 ppm by weight.
  • the second colorant additive is present in an amount ranging from from 0.1 to 3.0 ppm by weight.
  • the at least one colorant additive e.g., the first colorant additive or second colorant additive
  • the ratio of first colorant additive to second colorant additive ranges from 0.03 to 30. In additional aspects, the ratio of first colorant additive to second colorant additive is selected to provide optimal color and homogeneity.
  • the resin mixture further comprises at least one selective filter.
  • a selective filter selectively inhibits/blocks transmission of light in a selected wavelength range chosen within the 400-500 nm range, preferably in the 400-460 nm range.
  • a selective filter has little or no effect on transmission of wavelengths outside the selected wavelength range, unless specifically configured to do so.
  • the bandwdith of the selected range can preferably range from 10 to 70 nm, preferably from 10 to 60 nm more preferably 20 to 50 nm.
  • the selective filter preferably blocks or cuts at least 5 % of the light in the selected wavelength range, preferably at least 8 %, more preferably at least 12 %.
  • blocking X % of incident light in a specified wavelength range does not necessarily mean that some wavelengths within the range are totally blocked, although this is possible. Rather, “blocking X %" of incident light in a specified wavelength range means that an average of X % of said light within the range is not transmitted.
  • the light blocked in this way is light arriving on the main face of the optical article onto which the layer comprising the at least one optical filtering means is deposited, generally the front main face.
  • the selective filter is a notch filter.
  • the selective filter is an absorbing dye at least partially absorbing light in the 400-500 nm wavelength range, preferably in the 400-460 nm wavelength range.
  • the chemical nature of the absorbing dye that may act as filter for at least partially inhibiting light having the selected wavelength range is not particularly limited as far as the absorbing dye acts as a selective filter.
  • Blue light blocking dyes typically yellow dyes, are preferably selected to have little or no absorbance in other parts of the visible spectrum to minimize the appearance of other colors.
  • Porphyrins are well-known macrocycle compounds composed of four modified pyrrole subunits interconnected at their carbon atoms via methine bridges.
  • the parent porphyrin is porphine and substituted porphines are called porphyrins.
  • Porphyrins are the conjugate acids of ligands that bind metals to form (coordination) complexes.
  • porphyrins or porphyrin complexes or derivatives are interesting in that they provide selective absorption filters having a bandwidth in some cases of for example 20 nm in the selected blue range of wavelengths.
  • the selectivity property is in part provided by the symmetry of the molecules. Such selectivity helps to limit the distortion of the visual perception of color, to limit the detrimental effects of light filtering to scotopic vision and to limit the impact on circadian rhythm.
  • the one or more porphyrins or porphyrin complexes or derivatives are selected from the group consisting of Chlorophyll a; Chlorophyll b; 5,10, 15,20-tetrakis(4- sulfonatophenyl) porphyrin sodium salt complex; 5,10,15,20-tetrakis( -alkyl-4-pyridyl) porphyrin complex; 5,10,15,20-tetrakis( -alkyl-3-pyridyl) porphyrin complex, and 5,10,15,20- tetrakis( -alkyl-2-pyridyl) porphyrin complex, the alkyl being preferably an alkyl chain, linear or branched, comprising 1 to 4 carbon atoms per chain.
  • the alkyl may be selected from the group consisting of methyl, ethyl, butyl and propyl.
  • the complex usually is a metal complex, the metal being selected from the group consisting of Cu cation, Cr(III), Ag(II), In(III), Mn(III), Sn(IV), Fe (III), Co (II), Mg(II) and Zn(II).
  • Cr(III), Ag(II), In(III), Mn(III), Sn(IV), Fe (III), Co (II) and Zn(II) demonstrate absorption in water in the range of 425nm to 448nm with sharp absorption peaks.
  • the complexes they provide are stable and not acid sensitive.
  • the one or more porphyrins or porphyrin complexes or derivatives are selected from the group consisting of magnesium meso-tetra(4-sulfonatophenyl) porphine tetrasodium salt, magnesium octaethylporphyrin, magnesium tetramesitylporphyrin, octaethylporphyrin, tetrakis (2,6-dichlorophenyl) porphyrin, tetrakis (o-aminophenyl) porphyrin, tetramesitylporphyrin, tetraphenylporphyrin, zinc octaethylporphyrin, zinc tetramesitylporphyrin, zinc tetraphenylporphyrin, and diprotonated-tetraphenylporphyrin.
  • a UV and blue light-blocking resin mixture is used to produce a lens, a film, a laminate, or any other optical article known to those in the art.
  • a UV and blue light-blocking resin mixture is used to produce a wafer for integrating on the surface of an optical article.
  • a UV absorber and at least one colorant additive, preferably two colorant additives, are added to a reactive monomer and cast into an optical article.
  • a method for using dye spectrophotometer transmission curve data for producing a color balancing model for said dye can be used to predict perceived color for a variety of dye-related variables, including but not limited to dye concentration, lens thickness, and ratios of multiple dyes.
  • a color balancing model may be used to identify optimal dye concentrations to achieve desired levels of blue-cut performance, color neutrality, and/or color homogeneity.
  • compositions and/or methods can consist of or consist essentially of— rather than comprise/include/contain/have— any of the described elements and/or features and/or steps.
  • the term “consisting of or “consisting essentially of” can be substituted for any of the open-ended linking verbs recited above, in order to change the scope of a given claim from what it would otherwise be using the open-ended linking verb.
  • “Derivative,” in relation to a parent compound, refers to a chemically modified parent compound or an analogue thereof, wherein at least one substituent is not present in the parent compound or an analogue thereof.
  • One such non-limiting example is a parent compound which has been covalently modified. Typical modifications are amides, carbohydrates, alkyl groups, acyl groups, esters, pegylations and the like.
  • the words “comprising” (and any form of comprising, such as “comprise” and “comprises”), “having” (and any form of having, such as “have” and “has”), "including” (and any form of including, such as “includes” and “include”) or “containing” (and any form of containing, such as “contains” and “contain”) are inclusive or open-ended and do not exclude additional, unrecited elements or method steps.
  • compositions and methods for their use can "comprise,” “consist essentially of,” or “consist of any of the ingredients or steps disclosed throughout the specification.
  • transitional phase “consisting essentially of” in one non-limiting aspect, a basic and novel characteristic of the compositions and methods disclosed in this specification includes the compositions' abilities to reduce or prevent passage of blue light through a lens.
  • FIGS. 1A-1B are spectrohotometric transmission curves indicating thermal stability of different dyes.
  • FIG. 1A includes two solvent blue 104 stability curves, each run at different temperatures.
  • FIG. IB includes two solvent red 52 stability curves, each run at different temperatures. The two curves in each graph overlap almost completely, indicitating that the dyes are stable at low and high temperatures.
  • FIGS. 2A-2B each include three sets of spectrophotometric transmission curves.
  • FIG. 2A corresponds to Example II.
  • FIG. 2B corresponds to Example III.
  • the transmission curves include a standard clear lens reference curve, a transmission through a 1.3 mm uncoated lens, and a transmission curve through a 1.3 mm HMC coated lens.
  • thermoplastic resin for clear application with enhanced blue light absorbance must contain a combination of thermally and photo stable dyes with a specific absorbance, as well as, other additives such as mold release and heat stabilizers at sufficient levels to meet the demands for injection molding of ophthalmic quality parts.
  • the dyes used in the formulation include:
  • Tinuvin 329 2-(2H-benzotriazol-2-yl)-4-( l ,l ,3,3-tetramethylbutyl)phenol (CAS# 3147-75-9)
  • Tinuvin 326 2-(5-chloro-2H-benzotriazol- 2-yl)-6-(l ,l -dimethylethyl)- 4-methylphenol (CAS# 3896-1 1 -5)
  • Solvent Blue 104 l ,4-bis[(2,4,6-trimethylphenyl) amino] 9,10-anthracenedione (CAS# 1 16-75- 6)
  • Solvent Red 52 3H-Naphtho[l ,2,3-de]quinoline-2,7-dione,3-methyl-6-[(4-methylphenyl) amino] (CAS# 81 -39-0)
  • the general resin formulation is:
  • Base polycarbonate resin (100 parts) - includes a polycarbonate polymer, 0.05-0.5 wt% Tinuvin 329, 0.01 -0.3 wt% Tinuvin 326, a heat stabilizer, and a mold release agent
  • Solvent Red 52 (0.1 x 10 ⁇ 4 to 3.Ox 10 "4 parts) All general resin formulation were combined via a tumbling technique to produce a final pre- mix.
  • the final pre-mix may be produced in a single step, or may be composed of a concentrated pre-mix for each component.
  • the final pre-mix can be melt extruded with a compounder such as a single- or twin-screw prior to injection molding.
  • the final pre-mix can be added directly to the injection molding machine.
  • Compounding prior to injection molding has the advantage of ensuring a well-blended formula and minimal impact on existing injection molding processes.
  • Injection molding of the pre-mix directly has the advantage of eliminating the thermal history of compounding which could shift the color.
  • Optical standards (lenses of known thickness including a single dye at a known concentration) can be produced and measured with a spectrophotometer such as a Cary 50 or Cary 60 to produce transmission curve data for each dye.
  • This standard data may then be used to build a "color balancing model” based on Beer Lambert's Law.
  • the predicted color can then be computed at various dye concentrations, ratios and lens thicknesses.
  • the "color balancing model” may be used to pre-determine optimal dye concentrations to achieve a desired level of blue-cut, color neutrality, and color homogeneity.
  • Pre-mix concentrate was produced for each dye via a tumbling process by adding the dye to PC pellets.
  • Lens standard produced for each dye by mixing a known quantity of PC pellets with Pre- mix concentrate.
  • Lens standards were produced at low and high injection molding barrel temperatures. The standards were measured on a Cary 60 spectrophotometer to identify temperature impact on dye absorbance profiles. Low barrel temperature was 510 °F and the residence time was 100 seconds. High barrel temperature was 600 °F and residence time was 240 seconds.
  • the Cary 60 results show almost no measurable change in the transmission profile for either dye (two lines are almost completely overlapping).
  • both dyes have suitable thermal stability for the polycarbonate injection molding process.
  • Lens standards were produced for solvent blue 104 and solvent red 52.
  • the standards were measured on the Cary 60 before and after a Q-sun 40 hour test.
  • the color results before and after are given in Table 4 below. The color results show no significant change for either dye, indicating that both dyes exhibit suitable photostability.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention, selon des modes de réalisation, concerne des additifs de couleur et des formulations de couleur pour décaler ou réduire l'indice de jaunissement de lentilles anti-lumière bleue. Les additifs de couleur et les formulations de couleur sont sélectionnés pour fournir une neutralité de couleur et une homogénéité de couleur pour des lentilles anti-lumière bleue. L'invention concerne également des formulations de résines comprenant au moins deux additifs de couleur à équilibrage des couleurs.
PCT/EP2018/075245 2017-09-20 2018-09-18 Résine de polycarbonate ayant une action anti-lumière bleue et une couleur neutre améliorées Ceased WO2019057730A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PCT/EP2017/073812 WO2018054994A1 (fr) 2016-09-20 2017-09-20 Résine de polycarbonate ayant une action anti-lumière bleue et une couleur neutre améliorées
EPPCT/EP2017/073812 2017-09-20

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WO2019057730A1 true WO2019057730A1 (fr) 2019-03-28

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12429714B2 (en) 2019-11-26 2025-09-30 Oakley, Inc. High transmittance eyewear with chroma enhancement

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4528311A (en) 1983-07-11 1985-07-09 Iolab Corporation Ultraviolet absorbing polymers comprising 2-hydroxy-5-acrylyloxyphenyl-2H-benzotriazoles
EP0197508A1 (fr) * 1985-04-11 1986-10-15 Mobay Corporation Polycarbonates stabilisés
WO1997030362A1 (fr) * 1996-02-13 1997-08-21 Sola International, Inc. Revetement a neutralite chromatique arretant les uv pour lentilles en plastique
EP1580591A1 (fr) * 2004-03-25 2005-09-28 Intercast Europe S.P.A. Eléments optiques polarisant pour augmenter le contraste de couleur et méthode de fabrication
US20100029812A1 (en) * 2006-12-06 2010-02-04 Seiichi Tanabe Spectacle lens
US20110128494A1 (en) * 2008-05-28 2011-06-02 Naoshi Takahashi Spectacle lens
WO2015097492A1 (fr) * 2013-12-23 2015-07-02 Essilor International (Compagnie Generale D'optique) Article optique transparent ayant une apparence de jaunissement réduite
EP3296351A1 (fr) * 2016-09-20 2018-03-21 Essilor International Compositions de résine de polycarbonate de couleur homogène et performances blue-cut stables
EP3296775A1 (fr) * 2016-09-20 2018-03-21 Essilor International Appareils et procédés pour verres anti lumière bleue
EP3296799A1 (fr) * 2016-09-20 2018-03-21 Essilor International Article optique avec filtre anti-lumière bleue, filtre anti-uv renforcé et transparence élevée

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4528311A (en) 1983-07-11 1985-07-09 Iolab Corporation Ultraviolet absorbing polymers comprising 2-hydroxy-5-acrylyloxyphenyl-2H-benzotriazoles
EP0197508A1 (fr) * 1985-04-11 1986-10-15 Mobay Corporation Polycarbonates stabilisés
WO1997030362A1 (fr) * 1996-02-13 1997-08-21 Sola International, Inc. Revetement a neutralite chromatique arretant les uv pour lentilles en plastique
EP1580591A1 (fr) * 2004-03-25 2005-09-28 Intercast Europe S.P.A. Eléments optiques polarisant pour augmenter le contraste de couleur et méthode de fabrication
US20100029812A1 (en) * 2006-12-06 2010-02-04 Seiichi Tanabe Spectacle lens
US20110128494A1 (en) * 2008-05-28 2011-06-02 Naoshi Takahashi Spectacle lens
WO2015097492A1 (fr) * 2013-12-23 2015-07-02 Essilor International (Compagnie Generale D'optique) Article optique transparent ayant une apparence de jaunissement réduite
EP3296351A1 (fr) * 2016-09-20 2018-03-21 Essilor International Compositions de résine de polycarbonate de couleur homogène et performances blue-cut stables
EP3296775A1 (fr) * 2016-09-20 2018-03-21 Essilor International Appareils et procédés pour verres anti lumière bleue
EP3296799A1 (fr) * 2016-09-20 2018-03-21 Essilor International Article optique avec filtre anti-lumière bleue, filtre anti-uv renforcé et transparence élevée

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12429714B2 (en) 2019-11-26 2025-09-30 Oakley, Inc. High transmittance eyewear with chroma enhancement

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