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US-12624132-B2 - Liquid polymerizable allylic compositions comprising lake pigments

US12624132B2US 12624132 B2US12624132 B2US 12624132B2US-12624132-B2

Abstract

Disclosed is a polymerizable liquid composition for the manufacture of an optical article, including: a) at least one allyl monomer or allyl oligomer, b) at least one initiator for the polymerization of the allyl monomer or allyl oligomer, and c) at least one lake pigment including an organic ionic colorant and at least one compound including metal atoms having a charge opposite to that of the organic ionic colorant, d) wherein the lake pigment is not contained in nanoparticles, which are not the lake pigment itself, if the lake pigment is in the form of particles dispersed in the composition.

Inventors

  • Laurie MARION
  • Pierre FROMENTIN
  • Tipparat LERTWATTANASERI

Assignees

  • ESSILOR INTERNATIONAL

Dates

Publication Date
20260512
Application Date
20211220
Priority Date
20201223

Claims (20)

  1. 1 . A polymerizable liquid composition for the manufacture of an optical article, comprising: a) at least one allyl monomer or allyl oligomer, b) at least one initiator for the polymerization of said allyl monomer or allyl oligomer, and c) at least one lake pigment comprising an organic ionic colorant and at least one compound comprising metal atoms having a charge opposite to that of the organic ionic colorant, wherein the lake pigment is not contained in nanoparticles, which are not the lake pigment itself, if the lake pigment is in the form of particles dispersed in the composition.
  2. 2 . The polymerizable liquid composition according to claim 1 , wherein, an alkaline metal salt of the at least one compound comprising metal atoms or a halide salt of said compound or an acid form of said compound or a basic form of said compound is soluble in water, and/or an alkaline metal salt of the ionic organic colorant or a halide salt of the ionic organic colorant or a conjugate base of the ionic organic colorant or a conjugate acid of the ionic organic colorant is soluble in water.
  3. 3 . The polymerizable liquid composition according to claim 1 , wherein, the ionic organic colorant is anionic and the at least one compound comprising metal atoms is a non-alkali metallic cation selected from Mg 2+ , Al 3+ , Ca 2+ , Cr 3+ , Mn 2+ , Fe 2+ , Fe 3+ , Co 3+ , Ni 2+ , Cu 2+ , Zn 2+ , Ba 2+ , Sr 2+ , and mixtures thereof, or the ionic organic colorant is cationic and the at least one compound comprising metal atoms is an anionic coordination complex comprising metal atoms selected from polyoxometalates, [Cu 3 Fe(CN) 6 ] − , and mixtures thereof.
  4. 4 . The polymerizable liquid composition according to claim 1 , wherein the ionic organic colorant is anionic and the at least one compound comprising metal atoms is a trivalent cation.
  5. 5 . The polymerizable liquid composition according to claim 1 , wherein the ionic organic colorant is anionic and comprises carboxylate groups (RCO 2 − ) and/or sulfonate groups (RSO 3 − ).
  6. 6 . The polymerizable liquid composition according to claim 1 , wherein the at least one lake pigment is chosen from: a phosphomolybdotungstate salt of N-methyl derivatives of 4-[(4-aminophenyl)-(4-methyliminocyclohexa-2,5-dien-1-ylidene)methyl]aniline, a mixture of an aluminium, 7-hydroxy-8-[(4-sulfo-1-naphthalenyl)azo]-1,3-naphthalenedisulfonic acid complex and (E)-3,3′-dioxo-1H,1′H,3H,3′H-[2,2′-biindolylidene]-5,5′-disulfonic acid aluminium, a mixture of dihydrogen (ethyl) [4-[[4-[ethyl(3-sulphonatobenzyl)amino]phenyl](2-sulphonatophenyl)methylene]cyclohexa-2,5-dien-1-ylidene](3-sulphonatobenzyl)ammonium, aluminium salt and dialuminium tris[2-(2,4,5,7-tetrabromo-6-oxido-3-oxoxanthen-9-yl)-3,4,5,6-tetrachlorobenzoate], a mixture of tris[5-amino-4-hydroxy-3-(phenylazo)naphthalene-2,7-disulphonato(2-)]dialuminium and dihydrogen (ethyl)[4-[[4-[ethyl(3-sulphonatobenzyl)amino]phenyl](2-sulphonatophenyl)methylene]cyclohexa-2,5-dien-1-ylidene](3-sulphonatobenzyl)ammonium, aluminium salt.
  7. 7 . The polymerizable liquid composition according to claim 1 , wherein at least a portion of the at least one lake pigment is not dissolved in the at least one allyl monomer or allyl oligomer comprised in the composition, and wherein said portion of the at least one lake pigment is in the form of particles dispersed in the composition, and wherein the size of said particles of the at least one lake pigment is lower than 1 μm.
  8. 8 . The polymerizable liquid composition according to claim 1 , wherein the amount of lake pigment is from 1 to 40 ppm by weight relative to the total weight of the composition.
  9. 9 . The polymerizable liquid composition according to claim 1 , further comprising a light absorbing additive other than the at least one lake pigment selected from the group consisting of a colorant; a colorless light-absorbing additive; and mixtures thereof.
  10. 10 . The polymerizable liquid composition according to claim 9 , wherein the light absorbing additive has the following structure wherein R 3 and R 4 are each independently chosen from H or an alkyl chain having from 1 to 12 carbon.
  11. 11 . The polymerizable liquid composition according to claim 9 , wherein the light absorbing additive is contained in nanoparticles which are dispersed in the allyl monomer or allyl oligomer.
  12. 12 . The polymerizable liquid composition according to claim 1 , wherein the allyl monomer or allyl oligomer is selected from the group consisting of diethylene glycol bis(allyl carbonate), ethylene glycol bis(allyl carbonate), oligomers of diethylene glycol bis(allyl carbonate), oligomers of ethylene glycol bis(allyl carbonate), bisphenol A bis(allyl carbonate), diallyl phthalate, diallyl isophthalate, diallyl terephthalate, and mixtures thereof.
  13. 13 . The polymerizable liquid composition according to claim 1 , wherein the initiator is selected from a peroxydicarbonate, a peroxycarbonate, a peroxyester, a perketal, and mixtures thereof.
  14. 14 . A process for the preparation of the polymerizable liquid composition as defined in claim 1 , comprising the steps of: a) providing an allyl monomer or allyl oligomer; b) providing an initiator for the polymerization of said allyl monomer or allyl oligomer; c) providing at least one lake pigment; d) mixing said allyl monomer or allyl oligomer, said initiator, and said at least one lake pigment.
  15. 15 . A colorant capable of tolerating an initiator for the polymerization of an allyl monomer or allyl oligomer, the colorant comprising a lake pigment dispersed in the polymerizable liquid composition as defined in claim 1 .
  16. 16 . An optical article comprising a material obtainable or obtained by curing an allyl monomer or an allyl oligomer, wherein said material comprises at least one lake pigment dispersed therein and wherein said lake pigment is not contained in nanoparticles, which are not the lake pigment itself, if the lake pigment is in the form of particles dispersed in said material.
  17. 17 . The optical article according to claim 16 comprising an optical substrate essentially made of said material obtainable by curing an allyl monomer or an allyl oligomer and comprising the lake pigment dispersed therein.
  18. 18 . The optical article according to claim 16 , wherein the optical article is an ophthalmic lens.
  19. 19 . The polymerizable liquid composition of claim 9 , wherein the colorant is a dye or a pigment.
  20. 20 . The polymerizable liquid composition of claim 10 , wherein R 3 and R 4 are methyl groups.

Description

This application is the U.S. national phase of International Application No. PCT/EP2021/086751 filed Dec. 20, 2021 which designated the U.S. and claims priority to EP 20306671.7 filed Dec. 23, 2020, the entire contents of each of which are hereby incorporated by reference. The present invention relates to optical articles comprising light absorbing additives and more particularly to polymerizable compositions comprising light absorbing additives that can be polymerized into an optical article. It is often desired to incorporate a light absorbing additive (LAA) in an optical article such as an ophthalmic lens. The reason thereof can be related to the health of the user of the optical article or to their comfort or to cosmetic aspects. For example ultra-violet (UV) light (in particular the UVB and UVA range corresponding respectively to wavelengths comprised between 280 and 315 nm and between 315 and 380 nm), high energy visible (HEV) light (especially the wavelength range comprised between 380 and 450 nm corresponding to violet and blue light) and near infrared light (NIR; corresponding to the wavelength range from 780 to 1400 nm) have been shown to have adverse effects when the eye is exposed to excessive amounts of radiations in those wavelengths ranges. Ophthalmic lenses comprising UV LAA or HEV LAA or NIR LAA can thus be used to protect the health of the wearer of said ophthalmic lens. HEV LAA and, in most cases, UV LAA or NIR LAA absorb in the visible range, imparting an unaesthetic color to the lens. This is detrimental to the color perception of the wearer and in terms of cosmetic aspects. Resulting lenses may not be accepted by wearers, especially when considering non solar products. LAA absorbing in the visible range may be added to neutralize the color brought by the UV LAA or HEV LAA or NIR LAA. In this case, the LAA absorbing in the visible range acts as a color balancing agent. Different methods can be used to incorporate LAA into optical articles. For example, impregnation or imbibition methods consist in dipping a polymerized substrate, such as a lens substrate, in a bath containing a LAA dissolved or dispersed in an organic solvent. The LAA can also be comprised in a coating deposited onto the surface of the optical article substrate. However, incorporating the LAA directly in the polymerizable composition from which the substrate is obtained remains the preferred technique, as it does not require extra-processing steps to incorporate the LAA and it allows the LAA to be incorporated in relatively low concentrations. When the LAA is confined in a relatively thin layer in the article (which is the case when the LAA is comprised in a coating layer or in an impregnated layer), higher concentrations are needed which can deteriorate, for example, the mechanical properties of the article. A known class of substrate material is the class of allylic substrates, which results from the polymerization or copolymerization of allyl monomers and/or allyl oligomers such as CR-39®. The polymerization or copolymerization of these substrate materials necessitates that the polymerizable compositions comprise an initiator for initiating the polymerization or copolymerization, such as a peroxide, for example diisopropyl peroxydicarbonate (IPP). Under the reaction conditions for the polymerization of allylic substrates, the initiators or other reactive intermediates produced during the polymerization reaction may react with LAA and may degrade them. Imparting color to or balancing the color of an allylic substrate by incorporating a LAA directly in the polymerizable composition from which the substrate is obtained thus remains challenging. WO 2019/110264 discloses the use of LAA contained in nanoparticles acting as color balancing agents in polymerizable composition for the preparation of allylic lens substrates. The fact that these LAA are contained in nanoparticles protects them from degradation under the reaction conditions for the polymerization of allylic lens substrates. However, the preparation of the nanoparticles requires additional processing steps. EP 3382428 discloses the use of specific peroxide initiators with a single peroxycarbonate group (thus different from, for example, IPP) in polymerizable composition for the preparation of allylic lens substrates. The use of these initiators allows to avoid the degradation of some LLA (in this case acting as color balancing agents) under the reaction conditions for the polymerization of allylic lens substrates. However, these initiators provide a solution to the problem only for some dyes while some other dyes are still degraded when these initiators are used. There is thus a need in the industry for alternative polymerizable composition for the preparation of allylic substrates for optical articles, such as allylic lens substrates, comprising LAA such that the LAA are not degraded during the polymerization process. Inorganic pigments particles are LAA known t