Polymerizable and polymer compositions for optical materials having a refractive index of 1.54 to 1.58, spectacle lenses, and a method for producing the same

Abstract

The present invention relates to a polymerizable composition intended to form a polymer composition for optical materials such as the substrate of eyeglass lenses, the polymer composition obtained by polymerizing the polymerizable composition and having a refractive index of 1.54 to 1.58, an eyeglass lens containing the polymer composition, and a method for producing the optical material. The polymerizable composition has a refractive index of 1.54 to 1.58, - at least one non-aromatic polyisocyanate compound containing at least two -NCO groups; - at least one non-aromatic polythiol compound containing at least two -SH groups; and at least one polyol. According to the present invention, the at least one polyol comprises a polyether polyol.

Description

Technical Field

[0001] The present invention relates to a polymerizable composition intended to form a polymeric composition for optical materials such as a base material of an eyeglass lens, the polymeric composition obtained by polymerizing the polymerizable composition and having a refractive index of 1.54 to 1.58, an eyeglass lens containing the polymeric composition, and a method for producing this optical material. The present invention is generally applicable to optical polymeric materials having a refractive index in the intermediate range of 1.54 to 1.58 and the organic monomers from which they are derived.

Background Art

[0002] In a known manner, an organic base material for an eyeglass lens can be manufactured from a thermoplastic material or a thermosetting material.

[0003] Thermoplastic materials for organic lens substrates can generally be selected from polyamides; polyimides; polysulfones; polycarbonates and their copolymers; poly(ethylene terephthalate) and polymethyl methacrylate (PMMA).

[0004] Thermosetting materials for organic lens substrates generally include the following: - Cycloolefin copolymers such as ethylene / norbornene or ethylene / cyclopentadiene copolymers; - Homopolymers and copolymers of allyl carbonates of linear or branched aliphatic or aromatic polyols such as homopolymers of diethylene glycol bis(allyl carbonate); - Homopolymers and copolymers of (meth)acrylic acid and its esters derivable from bisphenol A; - Polymers and copolymers of thio(meth)acrylic acid and its esters; - Polymers and copolymers of allyl esters derivable from bisphenol A or phthalic acid and an allyl aromatic such as styrene; - Copolymers of urethane and thiourethane; - Polymers and copolymers of epoxy; and - Polymers and copolymers of sulfides, disulfides and episulfides may be selected from.

[0005] Such thermosetting materials more commonly use homopolymers and copolymers of diethylene glycol bis(allyl carbonate) having a refractive index (RI) of 1.54 to 1.58 (commonly referred to as "medium RI"), allyl and (meth)acrylic copolymers.

Summary of the Invention

Problems to be Solved by the Invention

[0006] Such acrylic or allyl lens substrates having an RI of about 1.56 exhibit acceptable optical properties. Nevertheless, the main drawback of such acrylic or allyl type thermosetting substrates for medium RI lenses is that they exhibit poor mechanical properties with respect to impact resistance over time. Another drawback of such acrylic / allyl lens substrates is in the casting process which deliberately includes several complex steps to obtain the lens substrate in order to polymerize the monomers.

[0007] Alternatively, it is known to produce polythiourethane-based lens substrates having a higher RI (higher than 1.58, usually 1.60 to 1.74) from specific monomers including alicyclic diisocyanate compounds, polythiol compounds, and diols selected from 1,4-butanediol, triethylene glycol and diethylene glycol. Such polythiourethane-based substrates are disclosed, for example, in European Patent No. 1925629B1, but always exhibit a high RI of 1.59 or more, and thus have the main drawback of being limited to high RI and not being usable to obtain substrates having an RI of 1.54 to 1.58.

Means for Solving the Problems

[0008] The subject of the present invention is to overcome at least the above-mentioned drawbacks, in particular by providing a lens substrate having both a medium RI and satisfactory mechanical properties.

[0009] This object is achieved in that the inventors have found that when a polyether polyol-based polyol is combined with other monomers, namely non-aromatic polyisocyanates and non-aromatic polythiols, these monomers are mixed in the presence of a catalyst and the monomer mixture is polymerized in a mold, a polymer composition based on modified polythiourethane having an RI of 1.54 to 1.58 can be obtained, and surprisingly, as will be explained below, it is possible to impart significantly enhanced mechanical properties to the polymer composition.

[0010] Accordingly, the polymerizable composition according to the present invention is intended to form a polymer composition for an optical material having a refractive index of 1.54 to 1.58, and the polymerizable composition comprises: - at least one non-aromatic polyisocyanate compound containing at least two -NCO groups; - at least one non-aromatic polythiol compound containing at least two -SH groups; - at least one polyol, which contains a polyether polyol and

[0011] As used herein, "polyether polyol" means a polyether of a polyol containing at least one polyether block and at least two -OH groups (alcohol functional groups) bonded thereto.

[0012] The polyether polyol not only makes it possible to offset the effects of the polyisocyanate and polythiol monomers on the refractive index of the polymer composition by significantly reducing this refractive index compared to the refractive index of a conventional polythiourethane-based composition that does not contain polyether polyol, but also, unexpectedly, by strengthening the resulting modified polythiourethane, as demonstrated in the following examples, it is noted that it is possible to significantly improve the mechanical properties of the polymer composition compared to those of a "proven" composition derived from both allyl and acrylic monomers.

[0013] According to a preferred embodiment of the present invention, the at least one non-aromatic polythiol contains at least 3 -SH groups, and the polymerizable composition further contains at least one dithiol compound.

[0014] In connection with the preferred embodiment, the at least one dithiol compound can preferably be an aliphatic dithiol selected from 1,5 - pentanedithiol, 1,4 - butanedithiol, 1,3 - propanedithiol, 1,10 - decanedithiol, 1,2 - butanedithiol, 2,3 - butanedithiol, 1,6 - hexanedithiol, and mixtures thereof.

[0015] (Regarding any of the above features of the present invention, including the preferred embodiment), the polyether polyol is as follows: - A molecular weight greater than 900 g / mol and less than or equal to 2000 g / mol, and / or - 3 to 5 OH groups It may have.

[0016] Polyether polyols generally usable in the present invention are preferably those each having, for example, the formula (OC x H y ) n(Wherein x and y are integers, and n is the number of ether repeating units for each polyether block), polyethers of polyols having at least three -OH groups each bonded to three polyether blocks can be mentioned. Preferably, x = 3 and y = 6.

[0017] More preferably, the polyether polyol is selected from glycerol propoxylate, glycerol-initiated polyoxypropylene polyol, sorbitol-initiated polyoxypropylene polyol, propylene glycol-initiated polyoxypropylene polyol, ethylene glycol-initiated polyoxypropylene polyol, sucrose-initiated polyoxypropylene polyol, and mixtures thereof.

[0018] Even more preferably, the polyether polyol of the present invention is glycerol propoxylate represented by the following formula (I).

Chemical formula

[0019] Also, in relation to any of the above features including the preferred embodiments, - The at least one non-aromatic polyisocyanate compound is preferably an aliphatic or alicyclic diisocyanate selected from isophorone diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane-4,4'-diisocyanate, butamethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, decamethylene diisocyanate, undecamethylene diisocyanate, trimethyl-1,6-diisocyanatohexane, 1,4-diisocyanatobutane, 1,12-diisocyanatododecane, and mixtures thereof; and / or - The at least one non-aromatic polythiol compound may be selected from dipentaerythritol hexakis 3-mercaptopropionate, pentaerythritol tetrakis(mercaptoacetate), pentaerythritol tetrakis 3-mercaptopropionate, and mixtures thereof; and / or - The molar ratio [SH]:[OH] in the polymerizable composition may be 5 or more and 24 or less, preferably 10 or more and 14 or less; and / or - The polymerizable composition comprises the following: · 35 wt% or more, preferably 45% - 60% of the at least one non-aromatic polyisocyanate compound, · 20 wt% or more, preferably 25% - 35% of the at least one non-aromatic polythiol compound, · 1 wt% or more, preferably 1.5% - 10%, more preferably 1.5% - 5% of the at least one polyether polyol, and · Optionally, in the preferred embodiment, 10% - 25% of the at least one dithiol compound and may contain.

[0020] It is particularly noted that the ratio [SH]:[OH] is lower than that of many conventional polythiourethane-based compositions lacking polyether polyol. This contributes to the refractive index of the composition of the present invention being lowered to fall within the medium RI range of 1.54 - 1.58.

[0021] The polymer composition according to the present invention is for an optical material having a refractive index of 1.54 - 1.58. This polymer composition, thanks to a suitable catalyst (e.g., a double metal cyanide called "DMC") and other usual components for in-mold polymerization such as a mold release agent, an ultraviolet absorber, etc., is obtained after the curing cycle and post-curing cycle intentionally carried out in a mold and with respect to a conventional polythiourethane-based lens substrate, and contains the polymerization product of the polymerizable composition as defined above.

[0022] Advantageously, the polymer composition of the present invention may have a glass transition temperature Tg that is 100 °C or higher and 150 °C or lower, as measured by dynamic mechanical analysis (DMA) or differential scanning calorimetry (DSC).

[0023] Also advantageously, the polymer composition of the present invention may have a storage modulus E' that is 3.0 GPa or higher, as measured by dynamic mechanical analysis (DMA) at 25 °C.

[0024] (Including the following examples) In this specification, - According to DMA measurement, the E' modulus and Tg are measured by dynamic mechanical analysis (three-point bending, heating from 23 °C to 160 °C at 2 °C / min) using a DMA Q800 from TA instruments; and - According to DSC measurement, the Tg at the midpoint is measured by a differential scanning calorimeter (DSC823e Module - Mettler Toledo) in a heating range of 10 °C / min from 23 °C to 180 °C under N2 at 50 mL / min.

[0025] Such Tg and / or modulus values obtained in the present invention are significantly higher than those of known compositions derived from both allyl and acrylic monomers, as demonstrated in the following examples for the "proof composition", which contributes to imparting improved mechanical properties to the compositions of the present invention.

[0026] The spectacle lens according to the present invention comprises a polymer composition as defined above, which preferably forms the base material of the lens.

[0027] The spectacle lens may be a spectacle lens such as a polarizing lens, a photochromic lens or a sunglass lens, may or may not be colored, and may or may not be for correction.

[0028] This spectacle lens may be inserted into a spectacle frame, or may be inserted into a head-mounted device that may be of the immersion or non-immersion type (in particular, see-through devices and see-around devices).

[0029] Preferably, the spectacle lens of the present invention is a corrective spectacle lens or a non-corrective spectacle lens worn in front of the eyes. The corrective lens can be used, for example, for the treatment of myopia, hyperopia, astigmatism and presbyopia, and can be either a single-focus spectacle lens or a multi-focus spectacle lens (such as a progressive addition spectacle lens).

[0030] The method according to the present invention for producing an optical material having a refractive index of 1.54 to 1.58 is as follows: a) In the presence of the catalyst (such as DMC) and optionally other additives such as a mold release agent and a UV absorber, - at least one non-aromatic polyisocyanate compound containing at least two -NCO groups; - at least one non-aromatic polythiol compound containing at least two -SH groups; - at least one polyol containing a polyether polyol; - optionally, when the at least one non-aromatic polythiol contains at least three -SH groups, at least one dithiol compound are mixed to form a polymerizable composition; and b) polymerizing the polymerizable composition in a mold to obtain a polymer composition forming the optical material is included.

[0031] Advantageously, the obtained polymer composition is cured, and then a post-curing cycle is carried out in a known manner as conventionally practiced for, for example, a prior art polythiourethane-based substrate composition.

Mode for Carrying Out the Invention

[0032] The terms "comprise" (and its grammatical variants such as "comprises" and "comprising"), "have" (and its grammatical variants such as "has" and "having"), "contain" (and its grammatical variants such as "contains" and "containing"), and "include" (and its grammatical variants such as "includes" and "including") are open-ended conjunctive verbs. These are used to define the presence of the recited features, integers, steps, or components, or groups thereof, but do not preclude the presence or addition of one or more other features, integers, steps, or components, or groups thereof. As a result, a method or a step within a method that "comprises", "has", "contains", or "includes" one or more steps or elements has those one or more steps or elements, but is not limited to having only those one or more steps or elements.

[0033] Unless otherwise indicated, all numbers or expressions referring to amounts, ranges, reaction conditions, etc. of components used in this specification are to be understood as being modified in all cases by the term "about". Also, unless otherwise indicated, the indication of an interval of values "X to Y" or "between X and Y" according to the present invention means including the values of X and Y.

[0034] Generally applicable features of the optical lens according to the present invention In a known aspect, the spectacle lens according to the present invention may include a multilayer coating covering the front main surface of the substrate (the rear main surface of the substrate is intended to be adjacent to the wearer's eye).

[0035] For certain applications, it is preferred that the front major surface of the substrate be coated with one or more functional coatings prior to the deposition of the multilayer coating. These functional coatings conventionally used in optical systems can be, without limitation, an impact-resistant primer layer, an abrasion-resistant and / or scratch-resistant coating, a polarizing coating, a photochromic coating or a coloring coating. Generally, this front major surface of the substrate is thus coated with an impact-resistant primer layer, an abrasion-resistant coating and / or an anti-scratch coating, or an impact-resistant primer layer coated with an abrasion-resistant coating and / or a scratch-resistant coating.

[0036] These abrasion-resistant and / or scratch-resistant coatings are preferably hard coatings based on poly(meth)acrylate or silane, generally containing one or more mineral fillers intended to increase the hardness and / or refractive index of the once-cured coating, and they are preferably produced from a composition containing at least one alkoxysilane and / or one hydrolyzate thereof obtained by hydrolysis with hydrochloric acid solution and optionally condensation and / or a curing catalyst. Coatings based on hydrolyzates of epoxysilanes as described in French Patent No. 2702486 (European Patent No. 0614957), U.S. Patent No. 4,211,823 and U.S. Patent No. 5,015,523 may be mentioned.

[0037] The abrasion-resistant and / or scratch-resistant coating composition can be deposited on the major surface of the substrate by dip coating or spin coating. It is then cured using an appropriate process (preferably thermally or under UV). The thickness of the abrasion-resistant and / or scratch-resistant coating generally ranges from 2 μm to 10 μm, preferably from 3 μm to 5 μm.

[0038] Prior to the deposition of the wear-resistant and / or scratch-resistant coating, it is possible to deposit on the substrate a primer coating (also called a tie layer) that improves the resistance to impact in the final product and / or the adhesion of subsequent layers. This coating can be any of the impact-resistant primer layers conventionally used on articles made of transparent polymers such as spectacle lenses.

[0039] Among the preferred primer compositions, there may be mentioned compositions based on thermoplastic polyurethane such as those described in JP-A-63-141001 and JP-A-63-87223, poly(meth)acrylic primer compositions such as those described in US Patent No. 5,015,523, compositions based on thermosetting polyurethane such as those described in European Patent No. 0404111, and compositions based on poly(meth)acrylic latex or polyurethane latex such as those described in US Patent No. 5,316,791 and European Patent No. 0680492. Preferred primer compositions are polyurethane-based compositions and latex-based compositions, particularly polyurethane latex optionally containing polyester units.

[0040] In the primer composition, it is also possible to use blends of these latexes, particularly blends of polyurethane latex and poly(meth)acrylic latex.

[0041] These primer compositions are deposited by dip coating or spin coating to form a primer layer having a thickness of 0.2 μm to 2.5 μm, preferably 0.5 μm to 1.5 μm after post-baking, and then dried at a temperature of at least 70°C, in some cases about 100°C, preferably about 90°C for 2 minutes to 2 hours, generally about 15 minutes.

[0042] Before a multilayer coating is deposited on a substrate optionally coated, for example, with a wear-resistant layer, it is possible to perform a chemical or physical activation treatment on the surface of the optionally coated substrate, with the intention of enhancing the adhesion of the coating. This pretreatment is generally carried out under vacuum. This can be an energy species, such as collisions by an ion beam (ion precleaning or IPC), corona discharge treatment, electron beam, ultraviolet treatment, or a plasma under vacuum, generally an argon or oxygen plasma treatment. It can also be an acidic or basic surface treatment and / or a surface treatment with a solvent (water or organic solvent).

[0043] The various layers of the multilayer coating and the optional underlying layer are preferably deposited by vacuum deposition using one of the following techniques. (i) Evaporation optionally assisted by an ion beam, (ii) Ion beam sputtering, (iii) Cathode sputtering, or (iv) Plasma enhanced chemical vapor deposition.

[0044] These various techniques are described in the books "Thin Film Processes" and "Thin Film Processes II" by Vossen & Kern, Ed., Academic Press, 1978 and 1991 respectively. The particularly recommended technique is the technique of vacuum evaporation.

[0045] Preferably, and as shown above, the deposition of each layer of the coating and the optional underlying layer is carried out by vacuum evaporation.

[0046] The spectacle lenses according to the invention can be made antistatic, i.e. not to retain and / or generate any appreciable electrostatic charge, by incorporating at least one conductive layer in the multilayer coating. This conductive layer is preferably located between two layers of the coating and / or adjacent to the high refractive index layer of the coating. Preferably, this conductive layer is located immediately below the low refractive index layer and ideally immediately below the outermost (low refractive index, e.g. silica-based) layer of the coating, forming the second layer from the bottom of the coating.

[0047] The conductive layer must be thin enough not to change the transparency of the coating and is preferably made of a highly transparent conductor. In this case, its thickness preferably varies in the range from 1 nm to 15 nm, more preferably from 1 nm to 10 nm. This conductive layer preferably comprises an optionally doped metal oxide selected from indium oxide, tin oxide, zinc oxide and mixtures thereof. Indium-tin oxide (In2O3:Sn in the case of tin-doped indium oxide), aluminium-doped zinc oxide (ZnO:Al), indium oxide (In2O3) and tin oxide (SnO2) are preferred. Even more preferably, this optically transparent conductive layer is a layer of indium-tin oxide (ITO) or a layer of tin oxide.

[0048] The spectacle lenses according to the invention may include, without limitation, the following: - a coating that can modify the surface properties and is formed on the external (i.e. exposed) surface of the multilayer inorganic coating, such as an anti-fouling or anti-fog top coat (external coating); - a coating, laminate film, within the substrate or within the wafer on the surface of the substrate, or directly incorporated into the substrate by being concentrated in the substrate by colouring or in a polymer, for example specific filtering functions such as UV, blue-violet (400 nm - 460 nm) or other visible wavelengths, or IR filtering; and / or - a polarizing function and may include complementary functionality such as the above.

[0049] Typically, it can be hydrophobic and / or oleophobic, and generally has a thickness of 10 nm or less, preferably 1 nm to 10 nm, more preferably 1 nm to 5 nm. As an antifouling coating, a fluorosilane or fluorosilazane type coating that can be obtained preferably by depositing a fluorosilane or fluorosilazane precursor containing at least two hydrolyzable groups per molecule can be mentioned. The precursor fluorosilane preferably contains a fluoropolyether group, more preferably a perfluoropolyether group.

[0050] Therefore, the spectacle lens according to the present invention can include, for example, a substrate continuously coated on its front main surface by an impact-resistant primer layer, an abrasion-resistant and / or scratch-resistant layer, the multilayer coating, and a hydrophobic and / or oleophobic top coat.

[0051] The rear main surface of the substrate can be continuously coated, for example, by an impact-resistant primer layer, an adhesion-resistant and / or scratch-resistant layer, an antireflection coating preferably having a low reflectance in the UV region, and a hydrophobic and / or oleophobic coating.

[0052] The following examples illustrate the present invention in a more detailed but non-limiting manner.

Example

[0053] Example 1 In the manner detailed in Table 1 below, first, two separate parts A and B consisting of the following components (each specified by its function, chemical trade name, supplier, CAS number, and mass fraction in the whole mixture of monomers and other additives forming the polymer composition) were prepared respectively to prepare the polymer composition according to the present invention.

[0054]

Table 1

[0055] IPDI: Isophorone diisocyanate

Chem.

Chem.

Chem.

Chem.

[0056] The polymerizable composition consisting of the specified parts A and B above was prepared according to the following continuous steps. 1) Part A is prepared by mixing a diisocyanate and an additive package consisting of a release agent, a UV absorber, and a catalyst together until the UV absorber is completely dissolved. 2) A polythiol, a dithiol, and a polyether polyol are mixed together to prepare part B. 3) Parts A and B are mixed at a temperature of less than 11°C for 1 hour under vacuum. 4) N2 gas is purged to replace the vacuum, and then part B is added and stirring is continued at 0°C for 10 minutes. 5) Degassing is carried out for 45 minutes while stirring at a low speed and then for 15 minutes without stirring. 6) The vacuum is released with N2 gas. 7) The mixture of the monomer and the additive is filled into the mold with a washed syringe.

[0057] The polymerization reaction was carried out in an electronically controlled oven adjusted according to the following cycle: at about 10 - 20°C for 8 hours, the temperature was regularly increased from 20°C to 130°C at about 5°C / hour - 25°C / hour for 9 hours, and at about 120 - 130°C for 6 hours.

[0058] The following Table 2 describes some physical properties of the lens substrates obtained according to the present invention from the perspective of refractive index n D and n E as well as Abbe number V D and V E (all measured by a prism coupler).

[0059]

Table 2

[0060] The following Table 3 describes the evaluation of the cosmetic properties of the lens substrates obtained according to the present invention, measured by a Cary instrument. No color balance was added to the mixture.

[0061]

Table 3

[0062] The following Table 4 describes some mechanical properties of the lens substrates obtained according to the present invention.

[0063]

Table 4

[0064] All measured physical, mechanical and cosmetic parameters of the lens substrates of the present invention, and their castability from the perspective of the process, are described, if possible, in the following Table 5 and compared with the same parameters and castability of a prior art lens substrate "1.56 market selection" manufactured from the specific "certified" polymer composition described above. This "certified" polymer composition "1.56 market selection" is derived from both allyl and acrylic monomers.

[0065]

Table 5

[0066] These measurements generally show better performance overall for the polythiourethane-based lens substrates of the present invention having an IR of about 1.56, compared to the allyl / acrylic-derived lens substrates “1.56 market selection”. In particular, the substrates of this first example of the present invention show improved mechanical resistance to impact compared to those of this “proven” allyl / acrylic-derived substrate.

[0067] Example 2 In the manner detailed in Table 6 below, first, two separate parts A and B consisting of the following components (each specified by its function, chemical trade name, supplier, CAS number, and mass fraction in the overall mixture of monomers and other additives forming the polymerizable composition) were prepared respectively to prepare another polymer composition according to the present invention.

[0068] [Table 6]

[0069] The polymerizable composition consisting of parts A and B specified above was prepared as defined in Example 1 above.

[0070] Table 7 below describes some physical properties of the lens substrates obtained according to the second example of the present invention, from the perspective of refractive index n D and n E as well as Abbe number V D and V E (all measured by a prism coupler).

[0071] [Table 7]

[0072] Table 8 below describes the cosmetic properties of the lens substrates obtained according to the second example of the present invention, measured by a Cary instrument. No color balance was added to the mixture.

[0073]

Table 8

[0074] Table 9 below describes some mechanical properties of the lens substrate obtained according to the second embodiment of the present invention.

[0075]

Table 9

[0076] These measurements also show better performance for the second substrate of the present invention based on polythiourethane having an IR of about 1.56, compared to the allyl / acrylic-derived lens substrate "1.56 market selection", indicating that the mechanical resistance to impact was significantly improved compared to that of the allyl / acrylic-derived substrate of this "witness". The present disclosure includes the following aspects of the invention: <Aspect 1> A polymerizable composition intended to form a polymer composition for an optical material having a refractive index of 1.54 to 1.58, - at least one non-aromatic polyisocyanate compound containing at least two -NCO groups; - at least one non-aromatic polythiol compound containing at least two -SH groups; - at least one polyol, at least one polyol including a polyether polyol and including a polymerizable composition. <Aspect 2> The polymerizable composition according to Aspect 1, wherein the at least one non-aromatic polythiol contains at least three -SH groups, and the composition further includes at least one dithiol compound. <Aspect 3> The polymerizable composition according to Aspect 2, wherein the at least one dithiol compound is preferably an aliphatic dithiol selected from 1,5-pentanedithiol, 1,4-butanedithiol, 1,3-propanedithiol, 1,10-decanedithiol, 1,2-butanedithiol, 2,3-butanedithiol, 1,6-hexanedithiol, and mixtures thereof. <Aspect 4> The polymerizable composition according to any one of Aspects 1 to 3, wherein the polyether polyol has a molecular weight greater than 900 g / mol and not more than 2000 g / mol. <Aspect 5> The polymerizable composition according to any one of Aspects 1 to 4, wherein the polyether polyol has 3 to 5 OH groups. <Aspect 6> The polymerizable composition according to any one of Aspects 1 to 5, wherein the polyether polyol is selected from glycerol propoxylate, glycerol-initiated polyoxypropylene polyol, sorbitol-initiated polyoxypropylene polyol, propylene glycol-initiated polyoxypropylene polyol, ethylene glycol-initiated polyoxypropylene polyol, sucrose-initiated polyoxypropylene polyol, and mixtures thereof. <Aspect 7> The at least one non-aromatic polyisocyanate compound is preferably an aliphatic or alicyclic diisocyanate selected from isophorone diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane-4,4'-diisocyanate, butamethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, decamethylene diisocyanate, undecamethylene diisocyanate, trimethyl-1,6-diisocyanatohexane, 1,4-diisocyanatobutane, 1,12-diisocyanatododecane, and mixtures thereof. The polymerizable composition according to any one of Aspects 1 to 6. <Aspect 8> The at least one non-aromatic polythiol compound is selected from dipentaerythritol hexakis 3-mercaptopropionate, pentaerythritol tetrakis(mercaptoacetate), pentaerythritol tetrakis 3-mercaptopropionate, and mixtures thereof. The polymerizable composition according to any one of Aspects 1 to 7. <Aspect 9> The molar ratio [SH]:[OH] in the polymerizable composition is 5 or more and 24 or less, preferably 10 or more and 14 or less. The polymerizable composition according to any one of Aspects 1 to 8. <Aspect 10> The polymerizable composition · 35 wt% or more, preferably 45% to 60% of the at least one non-aromatic polyisocyanate compound, · 20 wt% or more, preferably 25% to 35% of the at least one non-aromatic polythiol compound, and · 1 wt% or more, preferably 1.5% to 5% of the at least one polyether polyol The polymerizable composition according to any one of Aspects 1 to 9. <Aspect 11> A polymer composition for an optical material having a refractive index of 1.54 to 1.58, comprising a polymerization product of the polymerizable composition according to any one of Aspects 1 to 10. <Aspect 12> The polymer composition according to Aspect 11, having a glass transition temperature Tg of 100°C or more and 150°C or less, measured by dynamic mechanical analysis (DMA) or differential scanning calorimetry (DSC). <Aspect 13> The polymer composition according to Aspect 11 or 12, having a storage elastic modulus E' of 3.0 GPa or more, measured at 25°C by dynamic mechanical analysis (DMA). <Aspect 14> An eyeglass lens comprising the polymer composition according to any one of aspects 11 to 13, wherein the composition preferably forms a base material of the lens. <Aspect 15> A method for producing an optical material having a refractive index of 1.54 to 1.58, comprising: a) - at least one non-aromatic polyisocyanate compound containing at least two -NCO groups; - at least one non-aromatic polythiol compound containing at least two -SH groups; - at least one polyol containing a polyether polyol; - optionally, when the at least one non-aromatic polythiol contains at least three -SH groups, at least one dithiol compound mixing to form a polymerizable composition; and b) polymerizing the polymerizable composition in a mold to obtain a polymer composition forming the optical material A method comprising.

Claims

1. A polymerizable composition intended to form a polymer composition for an optical material having a refractive index of 1.54 to 1.58, - at least one non-aromatic polyisocyanate compound containing at least two -NCO groups; - at least one non-aromatic polythiol compound containing at least two -SH groups; - at least one polyol, at least one polyol containing a polyether polyol and the polymerizable composition being 45% to 60% by weight of the at least one non-aromatic polyisocyanate compound, 25% to 35% by weight of the at least one non-aromatic polythiol compound, and 1.5% to 5% by weight of the at least one polyether polyol A polymerizable composition containing.

2. The polymerizable composition according to claim 1, wherein the at least one non-aromatic polythiol contains at least three -SH groups and the composition further contains at least one dithiol compound.

3. The polymerizable composition according to claim 2, wherein the at least one dithiol compound is an aliphatic dithiol.

4. The polymerizable composition according to claim 3, wherein the aliphatic dithiol is selected from 1,5-pentanedithiol, 1,4-butanedithiol, 1,3-propanedithiol, 1,10-decanedithiol, 1,2-butanedithiol, 2,3-butanedithiol, 1,6-hexanedithiol and mixtures thereof.

5. The polymerizable composition according to any one of claims 1 to 4, wherein the polyether polyol has a molecular weight greater than 900 g / mol and not more than 2000 g / mol.

6. The polymerizable composition according to any one of claims 1 to 5, wherein the polyether polyol has 3 to 5 OH groups.

7. The polymerizable composition according to any one of claims 1 to 6, wherein the polyether polyol is selected from glycerol propoxylate, glycerol-initiated polyoxypropylene polyol, sorbitol-initiated polyoxypropylene polyol, propylene glycol-initiated polyoxypropylene polyol, ethylene glycol-initiated polyoxypropylene polyol, sucrose-initiated polyoxypropylene polyol, and mixtures thereof.

8. The polymerizable composition according to any one of claims 1 to 7, wherein the at least one non-aromatic polyisocyanate compound is an aliphatic or alicyclic diisocyanate selected from isophorone diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane-4,4'-diisocyanate, butamethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, decamethylene diisocyanate, undecamethylene diisocyanate, trimethyl-1,6-diisocyanatohexane, 1,4-diisocyanatobutane, 1,12-diisocyanatododecane, and mixtures thereof.

9. The polymerizable composition according to any one of claims 1 to 8, wherein the at least one non-aromatic polythiol compound is selected from dipentaerythritol hexakis 3-mercaptopropionate, pentaerythritol tetrakis(mercaptoacetate), pentaerythritol tetrakis 3-mercaptopropionate, and mixtures thereof.

10. The polymerizable composition according to any one of claims 1 to 9, wherein the molar ratio [SH]:[OH] in the polymerizable composition is 5 or more and 24 or less.

11. The polymerizable composition according to any one of claims 1 to 10, wherein the molar ratio [SH]:[OH] in the polymerizable composition is 10 or more and 14 or less.

12. A polymer composition for an optical material having a refractive index of 1.54 to 1.58, the polymer composition comprising a polymerization product of the polymerizable composition according to any one of Claims 1 to 11.

13. The polymer composition according to Claim 12, having a glass transition temperature Tg of 100°C or higher and 150°C or lower, measured by dynamic mechanical analysis (DMA) or differential scanning calorimetry (DSC).

14. The polymer composition according to Claim 12 or 13, having a storage modulus E' of 3.0 GPa or higher, measured by dynamic mechanical analysis (DMA) at 25°C.

15. An eyeglass lens comprising the polymer composition according to any one of Claims 12 to 14, wherein the composition forms a base material of the lens.

16. A method for producing an optical material having a refractive index of 1.54 to 1.58, a) - 45% to 60% by weight of at least one non-aromatic polyisocyanate compound containing at least two -NCO groups; - 25% to 35% by weight of at least one non-aromatic polythiol compound containing at least two -SH groups; - 1.5% to 5% by weight of at least one polyol containing a polyether polyol; - Optionally, when the at least one non-aromatic polythiol contains at least three -SH groups, at least one dithiol compound are mixed to form a polymerizable composition; and b) polymerizing the polymerizable composition in a mold to obtain a polymer composition forming the optical material comprising the method.

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