Intraocular lens composition

Abstract

The present invention relates to an intraocular lens composition comprising a polymer mixture of monomers, products comprising the composition and uses thereof. The composition of the present invention is completely free of vacuoles, thus resulting in a genuine shiny-free material. Further, it is sufficiently soft so as to be easy to fold, has a suitable tuning hardness to provide a comfortable deployment speed, requires low injection force, does not have prohibited stickiness, and has good optical properties. Finally, the intraocular lens composition does not suffer from calcification.

Description

Background Art

[0001] The present invention relates to the field of intraocular lens compositions.

[0002] An intraocular lens (IOL) is a lens that can be implanted in the eye to replace or assist the natural lens material in providing visual function. In the case of, for example, cataract treatment or myopia treatment, an IOL can be implanted in the eye.

[0003] Cataracts affect the eye's natural lens, causing it to become cloudy and blurring vision. In this case, an artificial lens can replace the natural lens, restoring vision. Other conditions, such as myopia, can be treated by placing an artificial lens over the natural lens, thereby changing the eye's optical power.

[0004] Intraocular lens materials are known and are commercially or experimentally available in many varieties. Typically, intraocular lens materials are polymeric compositions of one or more monomers. Important characteristics of such materials are clarity and stability. An important aspect of stability is the tendency of the lens material to form vacuoles over time. Vacuoles are small inclusions within the polymer lens material that contain water and are commonly referred to as glistenings. Due to the difference in refractive index between the lens material and the water within the vacuoles, incident light will diffract, resulting in glare and, therefore, reduced vision.

[0005] Furthermore, the IOL material must be flexible enough to allow the lens to fold. This is crucial during surgery, during which the lens is folded and placed inside a cartridge for implantation. It is then injected into the eye through a small incision via a nozzle. Finally, once in the eye, the lens unfolds and returns to its original shape. However, the material must be flexible enough to prevent the lens from unfolding too quickly. Deployment time is a crucial characteristic of lens materials, as waiting too long for the lens to unfold during surgery is inefficient and can lead to complications, while a lens that unfolds too quickly could damage ocular tissue. The material's viscosity should be low so as not to hinder the lens's unfolding within the eye after injection. The material must also be non-brittle and able to withstand the stresses generated during injection, where the lens is folded and pushed through the approximately 2mm syringe nozzle. Otherwise, the lens could break into two or more fragments or become deformed during injection. Finally, the lens must maintain high optical quality even after the lens has been injected and returned to its original shape.

[0006] Intraocular lens materials are typically either hydrophobic or hydrophilic. The advantage of hydrophilic materials is that they do not contain many vacuoles, but the disadvantage of this material is that they are often subject to calcification, which can make them unusable after an unpredictable period of time. Hydrophobic materials are better in this regard because they do not experience calcification, but hydrophobic materials have a tendency to form vacuoles. This causes the lens material to become increasingly shiny over time. In addition, hydrophobic lens materials are generally more sticky, which can lead to complications during the deployment process because the stickiness may prevent the lens from deploying or the haptic feedback portion from sticking to the optic. Many known hydrophobic lens materials are made into harder materials to reduce the shiny portion and reduce the stickiness, but harder lens materials also deploy more slowly, which can affect the efficiency of the procedure, make it more difficult to inject, and may even cause the nozzle to break during the procedure.

[0007] The present invention improves upon known lens materials by providing an intraocular lens composition that is completely free of vacuoles, thereby creating a truly shimmer-free material. Furthermore, it is flexible enough to be easily folded, has a suitably tuned hardness to provide a comfortable deployment speed, requires low injection force, exhibits no prohibitive tackiness, and exhibits good optical properties. Finally, the present intraocular lens composition is not susceptible to calcification. BRIEF DESCRIPTION OF THE DRAWINGS

[0008] Figure 1 : Lens from Example 1, magnified 20x and 100x.

[0009] Figure 2 : Lens from Example 2, magnified 20x and 100x.

[0010] Figure 3 : Lens from Example 3, magnified 20x and 100x.

[0011] Figure 4 : Lens from Example 4, magnified 20x and 100x.

[0012] Figure 5 : Lens from Example 5, magnified 20x and 100x.

[0013] Figure 6 : Lens from Example 6, magnified 20x and 100x.

[0014] Figure 7 : Lens from Example 7, magnified 20x and 100x.

[0015] Figure 8 : Lens from Example 8, magnified 20x and 100x.

[0016] Figure 9 : Lens from Example 9, magnified 20x and 100x.

[0017] Figure 10 : Lens from Example 10, magnified 20x and 100x.

[0018] Figure 11 : Lens from Example 11, magnified 20x and 100x.

[0019] Figure 12 : Lens from Example 12, magnified 20x and 100x.

[0020] Figure 13 : Lens from Example 13, magnified 20x and 100x.

[0021] Figure 14 : Alcon AcrySof lens, magnified 20x and 100x.

[0022] Figure 15 : Hoya 255 lens, magnified 20x and 100x.

[0023] Figure 16 : Avansee lens, 20x and 100x magnification.

[0024] Figure 17 : Tecnis lens, magnified 20x and 100x.

[0025] Figure 18 : Lens of Asquelio, magnified 20x and 100x.

[0026] Figure 19 : The model called "flying saucer".

[0027] Figure 20 : Lens from Example 19, magnified 20x and 100x.

[0028] Figure 21 : Lens from Example 20, magnified 20x and 100x. Detailed Description of the Invention

[0029] The present invention is as described in claim 1. The present invention provides an intraocular lens composition comprising a polymer mixture of at least four different monomers: a short (meth)acrylate crosslinker, a long (meth)acrylate crosslinker, one or more (meth)acrylate monomers of formula (I), and one or more C1-C4-alkyl (meth)acrylates, or a combination of phenyl-C1-C4-alkyl (meth)acrylates and cycloalkyl (meth)acrylates.

[0030] The composition of the present invention offers the following advantages over known compositions: it provides an intraocular lens composition that is completely free of vacuoles, thereby producing a truly shimmer-free material. Furthermore, it is sufficiently flexible for easy folding, possesses an appropriately tuned hardness to provide a comfortable deployment speed, requires low injection force, exhibits no prohibitive stickiness, and exhibits excellent optical properties. Finally, the present intraocular lens composition is not susceptible to calcification.

[0031] This intraocular lens composition may be abbreviated as IOL. It is a polymeric intraocular lens composition based on at least the above-described monomers, which have been suitably polymerized. In a preferred embodiment, the polymeric composition comprises at least 50% by weight of the above-described monomers, based on the weight of the composition. In a further preferred embodiment, the polymeric composition comprises at least 60% by weight, preferably at least 70% by weight, and more preferably at least 80% by weight of the above-described monomers, which have been suitably polymerized.

[0032] The term "polymeric mixture of monomers" is to be interpreted as known in the art and means that the monomers contained in the polymeric intraocular lens composition have been polymerized to provide the intraocular lens composition of the present invention. In this context, polymerized means that at least 90%, typically greater than 95%, and often substantially all of the monomer molecules (e.g., at least 99% of all monomer molecules) have undergone polymerization to produce the polymeric intraocular lens composition. If the total residual content of unreacted monomers is higher than desired, extraction with a suitable solvent may be optionally performed to eliminate the unreacted monomers, as is well known in the art.

[0033] Thus, a polymer mixture of monomers (which is an intraocular lens composition) is a polymer composition that preferably contains no monomers to a significant extent; except that, in the preparation of the intraocular lens composition, all monomers used have been incorporated into the polymer mixture during the polymerization reaction. A polymer mixture of monomers contains no unreacted monomers to a significant extent.

[0034] The intraocular lens composition comprises a polymer mixture of monomers and may also contain other conventional elements (such as UV and / or blue light filtering monomers) as described in WO 1995 / 011279 A1.

[0035] In some preferred embodiments, the intraocular lens composition consists solely of a polymer mixture, but may contain unavoidable impurities (eg, impurities resulting from the polymerization process, most notably impurities and degradation products resulting from the polymerization initiator).

[0036] The essential monomers contained in the polymer composition are (meth)acrylate monomers. Therefore, the polymerization process for obtaining the intraocular lens composition must be suitable for polymerizing the (meth)acrylate monomers. In a preferred embodiment, the polymerization process is a free radical polymerization process. Free radical polymerization is well known in the art.

[0037] Short crosslinker

[0038] The first essential monomer included in the intraocular lens composition is a short crosslinker comprising two or more (meth)acrylate moieties and a linker located between the two (meth)acrylate moieties, the linker being connected to the (meth)acrylate moieties via an ester group, wherein the longest linear sequence of atoms between the oxygen atom connecting the first (meth)acrylate moiety to the ester group of the linker and the oxygen atom connecting the second (meth)acrylate moiety to the ester group of the linker is 1 to 11 atoms. The short crosslinker can be represented by the following formula:

[0039]

[0040] In the formula, R is H or CH3, and SC represents a short linking moiety.

[0041] The (meth)acrylate moieties of the short crosslinker can independently be acrylate moieties or methacrylate moieties. In a preferred embodiment, the short crosslinker comprises two acrylate moieties or two methacrylate moieties. Most preferably, the short crosslinker comprises two methacrylate moieties (dimethacrylate).

[0042] The linking moiety is linked to the (meth)acrylate portion of the short crosslinker via an ester group, which is located on the carbonyl group of the (meth)acrylate.

[0043] A linking moiety is defined as a moiety that connects two (meth)acrylate moieties via a covalently bonded sequence of atoms. The longest linear sequence of atoms in the short crosslinker extends between the oxygen atom of the ester group connecting the first (meth)acrylate moiety to the linking moiety and the oxygen atom of the ester group connecting the second (meth)acrylate moiety to the linking moiety, and is 1-11 atoms, preferably 1-8 atoms, and more preferably 2-5 atoms. Thus, the short linking moiety is represented by a linear sequence of 1 to 11, 1 to 8, or 2 to 5 atoms.

[0044] The longest linear sequence of atoms of the short crosslinker comprises C atoms and optionally O atoms and / or N atoms, wherein the total number of C atoms exceeds the total number of O atoms and N atoms. In a preferred embodiment, the longest linear sequence of atoms of the short crosslinker comprises only C atoms and optionally O atoms, wherein the total number of C atoms exceeds the total number of O atoms (if present). In a more preferred embodiment, the C:O ratio is greater than 2:1.

[0045] The longest linear sequence of atoms of the short crosslinker may include side groups which do not significantly affect the reactivity of the (meth)acrylate portion of the short crosslinker during the polymerization reaction. Preferably, the side groups are selected from the group consisting of: R 2 , OR 2 SR 2 NR 2 2. COOR 2 or F, where R 2 is H, alkyl, cycloalkyl, heterocycloalkyl, aromatic moiety, or any combination thereof, wherein R 2 The molecular weight is at most 100 Da.

[0046] The short crosslinker may also contain more than two (meth)acrylate moieties, such as three or four or more (meth)acrylate moieties.

[0047] In a more preferred embodiment, the short crosslinking agent is ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, dibutylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolpropane ethoxylate tri(meth)acrylate, or Acrylates (maximum 1 unit of ethoxylate per arm), trimethylolpropane propoxylated tri(meth)acrylate (maximum 1 unit of propoxylate per arm), glyceryl tri(meth)acrylate, pentaerythritol tri(meth)acrylate, ethoxylated glyceryl tri(meth)acrylate (maximum 1 unit of ethoxylate per arm), propoxylated glyceryl tri(meth)acrylate (maximum 1 unit of propoxylate per arm), ethoxylated pentaerythritol tetra(meth)acrylate (maximum 1 unit of ethoxylate per arm), propoxylated pentaerythritol tetra(meth)acrylate (maximum 1 unit of propoxylate per arm) , di(trimethylolpropane) tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, or dipentaerythritol hexa(meth)acrylate, preferably ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, dibutylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, tri( In some embodiments, acrylates are preferred. In alternative preferred embodiments, methacrylates are preferred. In alternative preferred embodiments, methacrylates are preferred.

[0048] Preferably, the amount of the short crosslinker in the monomer mixture is 0.1 to 12 wt%, preferably 0.2 to 10 wt%, more preferably 0.5 to 8 wt%, based on the total amount of the monomer mixture.

[0049] In some more preferred embodiments, the amount of short crosslinking agent in the monomer mixture is 0.1 wt % to 3 wt %, preferably 0.1 wt % to 2 wt %. In other more preferred embodiments, the amount of short crosslinking agent in the monomer mixture is 2 wt % to 10 wt %, preferably 2 wt % to 7 wt %.

[0050] Long crosslinker

[0051] The second essential monomer included in the intraocular lens composition is a long crosslinker comprising two or more (meth)acrylate moieties and a linker located between the two (meth)acrylate moieties, the linker being connected to the (meth)acrylate moieties via an ester group, wherein the longest linear sequence of atoms between an oxygen atom connecting a first (meth)acrylate moiety to the ester group of the linker and an oxygen atom connecting a second (meth)acrylate moiety to the ester group of the linker is 14 atoms or more. The long crosslinker can be represented by the following formula:

[0052]

[0053] In this formula, R is H or CH3, and LC represents a long linking moiety.

[0054] The (meth)acrylate moieties of the long crosslinker can independently be acrylate moieties or methacrylate moieties. In a preferred embodiment, the long crosslinker comprises two acrylate moieties or two methacrylate moieties.

[0055] The linking moiety is linked to the (meth)acrylate portion of the long crosslinker via an ester group, which is located on the carbonyl group of the (meth)acrylate.

[0056] The linking moiety is defined as a moiety that connects two (meth)acrylate moieties via a covalently bonded sequence of atoms. The longest linear sequence of atoms of the long crosslinker linking moiety extends between the oxygen atom of the ester group connecting the first (meth)acrylate moiety to the linking moiety and the oxygen atom of the ester group connecting the second (meth)acrylate moiety to the linking moiety, and is 12 or more atoms, preferably at least 15 atoms, more preferably at least 20 atoms. In a preferred embodiment, the longest linear sequence of atoms of the long crosslinker is at most 100 atoms, preferably at most 80 atoms, more preferably at most 50 atoms, for example, at most 30 atoms.

[0057] The longest linear sequence of atoms of the long crosslinker comprises C atoms and optionally O atoms and / or N atoms, wherein the total number of C atoms exceeds the total number of O atoms and N atoms. In a preferred embodiment, the longest linear sequence of atoms of the long crosslinker comprises only C atoms and optionally O atoms, wherein the total number of C atoms exceeds the total number of O atoms (if present). In a more preferred embodiment, the C:O ratio is greater than 2:1.

[0058] The longest linear sequence of atoms of the long crosslinker may include side groups which do not significantly affect the reactivity of the (meth)acrylate portion of the long crosslinker during the polymerization reaction. Preferably, the side groups are selected from the group consisting of: R 2 , OR 2 SR 2 NR 2 2. COOR 2 or F, where R 2 is H, alkyl, cycloalkyl, heterocycloalkyl, aromatic moiety, or any combination thereof, wherein R 2 The molecular weight is at most 100 Da.

[0059] The long cross-linker may also comprise more than two (meth)acrylate moieties, such as three or four or more (meth)acrylate moieties.Such a long cross-linker may be referred to as a "star-shaped" long cross-linker.

[0060] In a more preferred embodiment, the long crosslinking agent is poly(ethylene glycol) di(meth)acrylate, poly(propylene glycol) di(meth)acrylate, poly(butylene glycol) di(meth)acrylate, poly(pentylene glycol) di(meth)acrylate, trimethylolpropane ethoxylated tri(meth)acrylate (having sufficient ethoxylated units to form a linking portion of at least 12 atoms), trimethylolpropane propoxylated tri(meth)acrylate (having sufficient propoxylated units to form a linking portion of at least 12 atoms), ethoxylated glyceryl tri(meth)acrylate (having sufficient ethoxylated units to form a linking portion of at least 12 atoms), propoxylated glyceryl tri(meth)acrylate (having sufficient propoxylated units to form a linking portion of at least 12 atoms), oxylate units to form a linking portion of at least 12 atoms), ethoxylated pentaerythritol tetra(meth)acrylate (having sufficient ethoxylate units to form a linking portion of at least 12 atoms), propoxylated pentaerythritol tetra(meth)acrylate (having sufficient propoxylate units to form a linking portion of at least 12 atoms), preferably poly(ethylene glycol) di(meth)acrylate, poly(propylene glycol) di(meth)acrylate, trimethylolpropane ethoxylated tri(meth)acrylate (having sufficient ethoxylate units to form a linking portion of at least 12 atoms) or trimethylolpropane propoxylated tri(meth)acrylate (having sufficient propoxylate units to form a linking portion of at least 12 atoms).

[0061] In some embodiments, acrylates are preferred. In alternative preferred embodiments, methacrylates are preferred.

[0062] In a preferred embodiment, the molecular weight of the long cross-linker is from 340 Da to 5000 Da, preferably from 346 Da to 3000 Da, more preferably from 350 Da to 1500 Da, and most preferably from 400 Da to 1000 Da.

[0063] Preferably, the amount of the long crosslinker in the monomer mixture is 0.5 to 25 wt %, preferably 1 to 25 wt %, more preferably 2 to 20 wt %, more preferably 2 to 10 wt %, based on the total amount of the monomer mixture.

[0064] In some more preferred embodiments, the amount of long crosslinking agent in the monomer mixture is 1 wt % to 15 wt %, preferably 2 wt % to 12 wt %. In some more preferred embodiments, the amount of long crosslinking agent in the monomer mixture is 1 wt % to 20 wt %, preferably 7 wt % to 18 wt %.

[0065] One or more (meth)acrylate monomers of formula (I)

[0066] The third essential monomer of the polymer intraocular lens is one or more (meth)acrylate monomers of formula (I):

[0067]

[0068] in:

[0069] X is -(C1-C4 alkyl)-O-, -(C1-C4 alkyl)-S-, -(C1-C4 alkyl)-N-, or C1-C8 alkyl, wherein the C1-C8 alkyl includes a cycloalkyl group, and one C atom is substituted by a heteroatom selected from the group consisting of O, S, and N;

[0070] Y is absent or is -C1-C4 alkyl;

[0071] n is 1 to 6;

[0072] R is H or CH3.

[0073] In formula (I), the alkyl moieties in X and Y can be straight-chain, branched or cyclic, but are preferably straight-chain. Optionally, the alkyl moieties can be substituted with groups that do not affect the reactivity of the (meth)acrylate moiety, for example, fluoro groups. In a preferred embodiment, X is -(C1-C4 alkyl)-O- or -(C1-C4 alkyl)-S-, more preferably X is -(C1-C4 alkyl)-O-. In a preferred embodiment, n is 1 or 2.

[0074] In a preferred embodiment, the (meth)acrylate monomer of formula (I) is methoxymethyl (meth)acrylate, methoxyethyl (meth)acrylate, methoxypropyl (meth)acrylate, methoxybutyl (meth)acrylate, ethoxymethyl (meth)acrylate, ethoxyethyl (meth)acrylate, ethoxypropyl (meth)acrylate, ethoxybutyl (meth)acrylate, propoxymethyl (meth)acrylate, propoxyethyl (meth)acrylate, propoxypropyl (meth)acrylate, propoxybutyl (meth)acrylate, butoxymethyl (meth)acrylate, butoxyethyl (meth)acrylate, butoxypropyl (meth)acrylate or butoxybutyl (meth)acrylate. In some embodiments, acrylate is preferred. In an alternative preferred embodiment, methacrylate is preferred.

[0075] In a preferred embodiment, the (meth)acrylate monomer of formula (I) is methoxyethyl methacrylate, methoxypropyl (meth)acrylate, ethoxyethyl (meth)acrylate, methoxyethoxyethyl (meth)acrylate, di(ethylene glycol) ethyl ether (meth)acrylate or triethylene glycol methyl ether (meth)acrylate or ethoxypropyl (meth)acrylate, or propoxyethyl (meth)acrylate.

[0076] In a more preferred embodiment, the (meth) acrylate monomer of formula (I) is methoxyethyl acrylate or methoxyethyl methacrylate. Most preferably, the (meth) acrylate monomers of one or more formulas (I) include methoxyethyl methacrylate, methoxyethyl acrylate, ethoxyethyl methacrylate, ethoxyethyl acrylate, methoxyethoxyethyl methacrylate, methoxyethoxyethyl acrylate, di(ethylene glycol) ethyl acrylate and triethylene glycol methyl ether methacrylic acid. In some embodiments, the mixture of methacrylate and acrylate of the (meth) acrylate monomer of the same formula (I) is preferred. In some preferred embodiments, the mixture of methoxyethyl acrylate and methoxyethyl methacrylate is preferred.

[0077] In a preferred embodiment, the (total) amount of the one or more (meth)acrylate monomers of formula (I) in the monomer mixture is 15-90% by weight, preferably 18-85% by weight.

[0078] In some more preferred embodiments, the total amount of the (meth)acrylate monomer of formula (I) in the monomer mixture is 35 wt % to 90 wt %, preferably 42 wt % to 83 wt %, based on the total amount of the monomer mixture. In other more preferred embodiments, the amount of the (meth)acrylate monomer of formula (I) in the monomer mixture is 15 wt % to 55 wt %, preferably 18 wt % to 45 wt %.

[0079] The fourth unit

[0080] The fourth essential monomer in the polymer intraocular lens composition is one or more C1-C4 alkyl (meth)acrylates, or a combination of a phenyl-C1-C4 alkyl (meth)acrylate and a cycloalkyl (meth)acrylate. The total amount of the alkyl (meth)acrylate or the combination of a phenyl-C1-C4 alkyl (meth)acrylate and a cycloalkyl (meth)acrylate is preferably 5% to 70% by weight, more preferably 5% to 35% by weight, based on the total monomer mixture.

[0081] One or more C1-C4-alkyl (meth)acrylates

[0082] The one or more C1-C4-alkyl (meth)acrylates may be represented by formula (II):

[0083]

[0084] in:

[0085] Y is -C1-C4 alkyl;

[0086] R is H or CH3.

[0087] In formula II, the alkyl portion of Y can be linear, branched or cyclic, but is preferably linear. Optionally, the alkyl portion can be substituted with a group that does not affect the reactivity of the (meth)acrylate portion, for example, a fluorine group.

[0088] In a preferred embodiment, the C1-C4-alkyl (meth)acrylate may be methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate [e.g., n-propyl (meth)acrylate or isopropyl (meth)acrylate], or butyl (meth)acrylate [e.g., n-butyl (meth)acrylate, sec-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, or cyclobutyl (meth)acrylate]. Of these (meth)acrylates, methacrylate is preferred. In a particularly preferred embodiment, the C1-C4-alkyl (meth)acrylate is methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, or tert-butyl (meth)acrylate, preferably methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, or tert-butyl acrylate, and most preferably methyl methacrylate, ethyl methacrylate, propyl methacrylate, or butyl methacrylate.

[0089] The amount of C1-C4-alkyl (meth)acrylate in the monomer mixture, if present, is preferably 5% to 75% by weight, more preferably 15% to 70% by weight, based on the total amount of the monomer mixture.

[0090] Phenyl-C1-C4-alkyl (meth)acrylate

[0091] If present, the phenyl-C1-C4-alkyl (meth)acrylate has the formula (III):

[0092]

[0093] in:

[0094] X is absent or is -C1-C4 alkyl;

[0095] R is H or CH3.

[0096] In formula III, the phenyl portion may be optionally substituted with groups that do not affect the reactivity of the (meth)acrylate portion, such as C1-C6 (cyclo)alkyl, C1-C6 (cyclo)alkoxy or fluoro groups.

[0097] In a preferred embodiment, the phenyl-C1-C4-alkyl (meth)acrylate can be phenylmethyl (meth)acrylate (also known as benzyl (meth)acrylate), phenyl (meth)acrylate, 1-phenylethyl (meth)acrylate, 2-phenylethyl (meth)acrylate, 1-phenylpropyl (meth)acrylate, 2-phenylpropyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, phenylcyclopropyl (meth)acrylate, 1-phenylbutyl (meth)acrylate, 2-phenylbutyl (meth)acrylate, 3-phenylbutyl (meth)acrylate, 4-phenylbutyl (meth)acrylate or phenylcyclobutyl (meth)acrylate.

[0098] In a more preferred embodiment, the phenyl-C1-C4-alkyl (meth)acrylate is phenyl (meth)acrylate, phenylmethyl (meth)acrylate, phenylethyl (meth)acrylate.

[0099] If present, the amount of phenyl-C1-C4-alkyl (meth)acrylate in the monomer mixture is preferably 5% to 40% by weight, more preferably 8% to 33% by weight, based on the total amount of the monomer mixture.

[0100] Cycloalkyl (meth)acrylate

[0101] If present, the cycloalkyl (meth)acrylate has the formula (IV):

[0102]

[0103] in:

[0104] X does not exist and is C1-C5 alkyl or -[(C1-C4 alkyl)-O] n -, where n is 1-8;

[0105] Y is a C3-C18 alkyl group comprising at least one cycloalkyl moiety, wherein the C3-C18 alkyl group optionally comprises one or more heteroatoms selected from O and N groups;

[0106] R is H or CH3.

[0107] In formula IV, the alkyl portion of X may be linear, branched or cyclic, but preferably is linear. Optionally, the alkyl portion may be substituted with groups that do not affect the (meth)acrylate portion, for example, fluorine groups.

[0108] Preferably, X is absent and is methylene, ethylene, propylene, butylene or pentylene, more preferably X is absent and is methylene or ethylene. Most preferably, X is absent.

[0109] Y is a C3-C18 alkyl group comprising at least one cycloalkyl moiety, wherein optionally one or more C atoms of the alkyl group may be substituted by O atoms and / or N atoms, preferably by O atoms. Thus, the total number of C atoms, O atoms and / or N atoms in the group Y does not exceed 18. If present, O atoms and N atoms are preferably not located in the cycloalkyl moiety.

[0110] Preferably, Y comprises a monocyclic ring system, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, or a bicyclic or tricyclic alkyl group comprising any combination of these monocyclic ring systems. Particularly preferably, the bicyclic or tricyclic ring system is norbornyl, isobornyl, or adamantyl.

[0111] Y may further comprise a linear or branched alkyl moiety which may contain heteroatoms O and / or N, which is located between X and the cycloalkyl moiety. Optionally, the cycloalkyl moiety may also be substituted with an alkyl group, a fluoro group, a hydroxyl (OH) or amino group (NH2), and an alkyl-substituted derivative of the amino or hydroxy substituted cycloalkyl moiety (i.e., an ether or a secondary or tertiary amine).

[0112] In a preferred embodiment, Y is a cycloalkyl group, more preferably a C3-C10 cycloalkyl group.

[0113] In a more preferred embodiment, the cycloalkyl (meth)acrylate is cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, cycloheptyl (meth)acrylate, norbornyl (meth)acrylate, isobornyl (meth)acrylate, or adamantyl (meth)acrylate. Among these (meth)acrylates, methacrylate is preferred. Alternatively, acrylate is preferred.

[0114] If present, the amount of cycloalkyl (meth)acrylate in the monomer mixture is preferably 10% to 55% by weight, more preferably 14% to 45% by weight, based on the total amount of the monomer mixture.

[0115] Optional monomers in the monomer mixture

[0116] As mentioned above, the polymer composition preferably comprises at least 50% by weight of the above-mentioned monomers, based on the weight of the composition. In a preferred embodiment, the polymer composition comprises at least 60% by weight, preferably at least 70% by weight, and more preferably at least 80% by weight of the above-mentioned monomers, which are suitably polymerized. Therefore, other conventional monomers other than those listed above may be present to a considerable extent. These other conventional monomers may be selected from all (meth) acrylic monomers and vinyl monomers commonly found in the field of intraocular lenses that do not fall into one of the above-mentioned basic categories.

[0117] In a preferred embodiment, the monomer mixture further comprises a UV light-filtering chromophore ("UV blocker" or "UV filter") in an amount suitable for absorbing at least 50%, preferably at least 75%, and more preferably at least 85% of radiation having a wavelength of 350 nm to 400 nm, preferably a benzotriazole-substituted methacrylate. Examples of such UV light-filtering chromophores are 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl methacrylate (CAS 96478-09-0) and 2-(4-benzoyl-3-hydroxyphenoxy)ethyl acrylate (CAS 16432-81-8).

[0118] If the composition comprises a UV light filtering chromophore as defined, the amount of this monomer is preferably from 0.1% to 2% by weight, preferably from 0.2% to 1% by weight, more preferably from 0.4% to 0.8% by weight of the monomer mixture.

[0119] In other preferred embodiments, the monomer mixture further comprises a blue light-filtering chromophore ("blue filter") in an amount suitable for absorbing at least 50%, preferably at least 75%, and more preferably at least 85% of radiation having a wavelength of 400 nm to 500 nm. Examples of such blue light-filtering chromophores are polymerizable yellow dyes as described in WO 1995 / 011279 A1. If the composition comprises the defined blue light-filtering chromophore, the amount of such monomer is preferably from 0.1% to 2% by weight, preferably from 0.2% to 1% by weight, and more preferably from 0.4% to 0.8% by weight of the monomer mixture.

[0120] Preferred embodiments

[0121] A preferred intraocular lens composition according to the present invention comprises:

[0122] 0.1 to 12% by weight, preferably 0.5 to 8% by weight, of a short crosslinker;

[0123] 1% to 25% by weight, preferably 2% to 10% by weight, of a long crosslinker;

[0124] 15% to 90% by weight, preferably 18% to 85% by weight, of one or more (meth)acrylate monomers of formula (I);

[0125] 5% to 75% by weight, preferably 15% to 70% by weight, of one or more C1-C4 alkyl (meth)acrylates of formula (II) (if present);

[0126] 5% to 40% by weight, preferably 8% to 33% by weight, of one or more phenyl C1-C4 alkyl (meth)acrylates of formula (III) (if present);

[0127] 10% to 55% by weight, preferably 14% to 45% by weight, of a cycloalkyl (meth)acrylate of formula (IV) (if present); and

[0128] Optionally, 0.1 to 2 wt% of a UV light filtering chromophore and / or 0.1 to 2 wt% of a blue light filtering chromophore,

[0129] Here, wt% refers to the weight% in the monomer mixture based on the total amount of the monomer mixture.

[0130] In a more preferred embodiment, the intraocular lens composition comprises a polymer mixture of the following monomers:

[0131] 15% to 90% by weight, preferably 18% to 85% by weight, of one or more (meth)acrylate monomers of formula (I);

[0132] 5% to 75% by weight, preferably 15% to 70% by weight, of one or more C1-C4 alkyl (meth)acrylates of formula (II);

[0133] 1% to 25% by weight, preferably 2% to 10% by weight, of a long crosslinker;

[0134] 0.1 to 12 wt. %, preferably 0.5 to 8 wt. % of short crosslinkers.

[0135] This mixture is referred to as embodiment A. In a more preferred embodiment, a UV light filtering chromophore and / or a blue light filtering chromophore as described above is included in embodiment A.

[0136] In an alternative more preferred embodiment, the intraocular lens composition comprises a polymer mixture of the following monomers:

[0137] 15% to 90% by weight, preferably 18% to 85% by weight, of one or more (meth)acrylate monomers of formula (I);

[0138] 5% to 40% by weight, preferably 8% to 33% by weight, of one or more phenyl C1-C4-alkyl (meth)acrylates of formula (III);

[0139] 10% to 55% by weight, preferably 14% to 45% by weight, of cycloalkyl(meth)acrylate of formula (IV);

[0140] 1% to 25% by weight, preferably 2% to 10% by weight, of a long crosslinker;

[0141] 0.1 to 12 wt. %, preferably 0.5 to 8 wt. % of short crosslinkers.

[0142] This mixture is referred to as embodiment B. In a more preferred embodiment, a UV light filtering chromophore and / or a blue light filtering chromophore as described above is included in embodiment B.

[0143] Other preferred compositions according to the present invention comprise polymer mixtures of the monomers of Examples 1-13. For each of the exemplary compositions in Examples 1-13, the amount of the listed monomers present may deviate slightly from the amount used in the examples. In this context, a slight deviation means that the amount of monomer may be 5% by weight lower or 5% higher than the indicated amount in the examples, preferably 2% by weight lower or 2% higher than the exemplary amount, more preferably 1% by weight lower or 1% higher, and even more preferably 0.5% by weight lower or 0.5% higher. Thus, for each lens composition according to the present invention in the examples, the listed monomers may be present in the listed amounts ±5% by weight, preferably ±2% by weight, more preferably ±1% by weight, and most preferably ±0.5% by weight. Such slight deviations do not affect the properties of the resulting lens. Thus, the present invention provides a lens material characterized by being in accordance with each of the examples of the present invention.

[0144] Characteristics of the polymer composition

[0145] The intraocular lens compositions defined herein are completely free of vacuoles. This distinguishes the compositions of the present invention from prior art compositions, in which the tendency of a composition to form vacuoles over time is determined by aging the composition at a specific temperature for a specific period of time. Common aging temperatures disclosed in the literature are 37°C or 40°C (for example, in WO2015084788A1 and US8449610B2, the aging temperature is 45°C for 1 day and then at room temperature for 1-2 hours; in EP1857477B1, a temperature of 33°C is used; in Biomedical Optic Express 4, 8, 2013, 1294-1304, a temperature of 35°C for 8 hours is used; in J Cataract Refract Surg 2004, 30, 1768-1772, a maximum temperature of 41°C is used; in WO2012106118A2, a temperature of 50°C is used, but the specimen is examined at room temperature without a step); for example, the aging time is 1 day or several hours. In prior art experiments on vacuolar formation, the aging temperature has never been as high as 50°C or higher, and then cooled to room temperature.

[0146] It is known and accepted that aging the composition at elevated temperatures simulates the accelerated aging process under in vivo conditions. Thus, the tendency of a material to form vacuoles after years of use can be simulated by aging at elevated temperatures for shorter periods of time. This test involves aging the composition in a 0.9% aqueous NaCl solution at 50°C for 16 hours or longer. These conditions are significantly more severe than those previously employed in the art, and thus the method is more sensitive in demonstrating vacuolar formation after prolonged in vivo use.

[0147] Comparisons of various known intraocular lens compositions using current standardized and more stringent test conditions revealed that known compositions are susceptible to vacuole formation and / or turbidity. However, the compositions of the present invention are completely vacuole-free and remain completely vacuole-free, also using the more stringent test conditions of the present invention described above. This makes the compositions of the present invention particularly suitable for use as foldable implantable ophthalmic devices in ophthalmic surgery, for example, in the treatment of cataracts and refractive surgery, such as in the treatment of myopia, because vacuole formation is completely prevented.

[0148] The intraocular lens composition defined herein preferably has a water absorption of less than 10% by weight, more preferably less than 5% by weight. Water absorption is measured by weight according to the following steps: a certain number of lenses (usually 10 to 20) are allowed to fully hydrate and their weight is measured. Next, the lenses are dried in a vacuum oven until the weight stabilizes. Subsequently, the water absorption (percentage) is calculated according to the formula (W 湿 -W 干 ) / W 干*100% measured, where W 湿 is the weight of the hydrated lens (the hydrated lens is of course dried with residual water on its surface), W 干 is the weight of the lens after complete drying in a vacuum oven.

[0149] The viscosity of the intraocular lens composition defined herein is within the limits required for use in intraocular surgery. Viscosity can be assessed by the following procedure: a lens having a diameter of approximately 14 mm, an optical portion of approximately 6 mm, and a plan parallel flap circumference of approximately 0.35 mm (see Figure 9 A saucer-shaped specimen (likely a non-sticky material) is folded in half and pressure is applied with the fingers for 1 or 2 seconds or longer, causing one half of the specimen flap to contact the other half of the same specimen and compress it. Subsequently, the pressure is released. A non-sticky specimen will easily return to its original shape, while a sticky specimen will remain folded because the interaction between the two halves of the lens is too strong to allow the lens to unfold. Furthermore, and most importantly, when finished lenses of the current formulation were injected using a syringe with a 2.2mm nozzle and a viscoelastic medium, no unfolding due to viscosity was observed.

[0150] The intraocular lens composition defined herein is sufficiently soft and foldable. Its unfolding time is 1-150 seconds, preferably 3-120 seconds, and more preferably 5-30 seconds. The unfolding time is determined by recording a video of the lens after it passes through the syringe nozzle and is deposited in a small water bath at 26°C (simulating surgical conditions) to accurately observe and time the unfolding process.

[0151] Thus, the present invention also provides an intraocular lens, an artificial cornea, a corneal ring, a corneal implant or a corneal inlay comprising an intraocular lens composition as defined herein.

[0152] Method for preparing intraocular lens composition

[0153] The present intraocular lens composition can be prepared by a generally known polymerization process using the monomer mixture defined above as the starting mixture for polymerization. In a preferred embodiment, the polymerization process is a free radical polymerization process. In other preferred embodiments, the polymerization is carried out in a single step using the monomer mixture as a reactant. The monomer mixture may suitably contain a solvent, as is known in the art. However, the polymerization mixture preferably consists solely of the monomers to be polymerized and a polymerization initiator.

[0154] Therefore, the present invention also relates to a method for preparing the intraocular lens composition as described herein, comprising the steps of:

[0155] 1) preparing the monomer mixture described above;

[0156] 2) preferably adding a free radical polymerization initiator;

[0157] 3) Allowing polymerization to occur;

[0158] 4) If necessary, extract with a suitable solvent to eliminate residual unreacted monomers or other impurities.

[0159] Suitable polymerization initiators are free radical polymerization initiators. Such compounds are well known, and any compound known for this purpose may be used. Preferably, the initiator is a diazo initiator, such as 2,2-azobis(2,4-dimethylvaleronitrile), 2,2′-azobis(2-methylpropionitrile), azobisisobutyronitrile, lauroyl peroxide, benzoyl peroxide, but photoinitiators such as phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide may also be used. Further preferably, the initiator is an organic peroxide, such as di-tert-butyl peroxide, benzoyl peroxide, lauroyl peroxide, or methyl ethyl ketone peroxide.

[0160] As known to those skilled in the art, the amount of initiator depends on the type of initiator and the specific monomer mixture. Typically, the amount of initiator expressed as a % by weight of the monomer mixture may be from 0.1 wt % to 2 wt %, preferably from 0.2 wt % to 1.5 wt %, more preferably from 0.5 wt % to 1 wt %.

[0161] In certain embodiments, it is necessary to reduce the atmospheric oxygen content prior to polymerization, but in other embodiments of the present composition, polymerization can be carried out in an oxygen-containing atmosphere (e.g., air). This is an advantage because it avoids the conventional use of an inert atmosphere. The polymerization of the present composition can be carried out, for example, in a gas atmosphere containing approximately 21% oxygen. Preferably, polymerization is carried out in an atmosphere having an oxygen content of preferably less than 5% and most preferably less than 1%.

[0162] Alternatively, the polymerization can be carried out in an inert atmosphere, as is known in the art. The inert atmosphere can include nitrogen or argon (or mixtures thereof) or other known inert gases.

[0163] Polymerization is typically carried out in a mold formed from polypropylene or other suitable material that provides the lens shape and optical properties, or is manufactured in the form of a sheet or button of sufficient thickness to form the lens by classical lathe cut technology known in the art.

[0164] Suitably, after polymerisation is complete, the resulting polymer composition is removed from the mould and may optionally be cut to form the haptic portion of the lens. Upon completion, the lens is suitably stored in a water-based system, either dry or hydrated.

[0165] For the purpose of clear and concise description, features are described herein as part of identical or separate embodiments. However, it should be understood that the scope of the present invention may include embodiments with a combination of all or part of the features described. The present invention will now be described by way of the following non-limiting examples.

[0166] According to an embodiment of the present invention

[0167] Examples 1 to 13 show the composition of the composition according to the invention.

[0168] Example 1:

[0169]

[0170] Example 2:

[0171]

[0172] Example 3:

[0173]

[0174] Example 4:

[0175]

[0176] Example 5:

[0177]

[0178]

[0179] Example 6:

[0180]

[0181] Example 7:

[0182]

[0183] Example 8:

[0184]

[0185] Example 9:

[0186]

[0187] Example 10:

[0188]

[0189] Example 11:

[0190]

[0191] Example 12:

[0192]

[0193] Example 13:

[0194]

[0195] The components are mixed together and stirred at room temperature until homogeneity is achieved.The mixture is then filtered through a 0.45 μm inert filter and used to fill a mold made of polypropylene or other suitable material.

[0196] Next, the filled mold is placed in an oven to cure the polymer mixture by increasing the temperature from room temperature (approximately 20° C.) to 90° C. over 5 hours, and then maintaining the temperature at 90° C. for an additional 6 hours. As will be appreciated by those skilled in the art, this thermal profile can be modified to tune the results for a specific mixture.

[0197] At this point, the mold is allowed to cool to room temperature, then the mold is opened and the part is recovered. Depending on the mold type, further processing such as lathing and milling as known in the art may be performed. Extraction of residual unreacted monomers may be considered.

[0198] Comparative Example

[0199] Examples 14-17 show compositions that are not within the scope of the present invention and that do exhibit vacuole formation or other problems.

[0200] Example 14:

[0201]

[0202] Example 15:

[0203]

[0204] Example 16:

[0205]

[0206] Example 17:

[0207]

[0208] Example 18:

[0209]

[0210] Lenses were prepared from these compositions according to the same procedures described above for Examples 1-13.

[0211] The present invention improves upon known lens materials and provides an intraocular lens composition that is completely free of vacuoles, even under demanding testing conditions, has a hardness appropriately adjusted to provide a comfortable deployment speed, easy folding, and comfortable injection force, and does not exhibit prohibitive stickiness. Furthermore, the refractive index (RI) is within acceptable values ​​in all cases, and the optical quality (MTF) is consistently very good.

[0212] Shiny part test

[0213] The glint test is performed by placing the lens in a 7 ml vial filled with 0.9% aqueous NaCl solution, keeping the vial at 50°C for 16 hours or longer, cooling it at room temperature (approximately 20°C) for 0.5 to 1 hour, removing the lens from the vial, and analyzing it under a microscope (Olympus BX50) under dark field illumination at a magnification of 20x to 100x, and up to 500x if necessary. Retroillumination is used on the microscope, and no filters are added. The formation of vacuoles is visually assessed.

[0214] For the lenses of Examples 1-13, the results are shown in Figure 1-13 As can be seen, no vacuoles were observed in the lenses prepared according to the present invention. The results of the glint test and other parameters are summarized in Table 1.

[0215] The lenses of Examples 14-18 were outside the scope of the present invention. The lenses of Examples 14-17 did exhibit vacuoles; the lens of Example 18 turned white after hydration in water and already exhibited some vacuoles before the shine test was performed. These results are summarized in Table 2.

[0216] For comparison, the following commercially available lenses were used for the sparkle test:

[0217] AcrySof (R) (Alcon)

[0218] iSert (R) 255(HOYA Surgical Optics)

[0219] ·Avansee TM(Kowa pharmaceutical Europe)

[0220] ·Tecnis (R) (Johnson&Johnson SurgicalVision)

[0221] Asqelio TM (AST Products)

[0222] The results are shown in Figure 14-18 and are summarized in Table 3.

[0223] In Alcon AcrySof Figure 14 )、Hoya 255( Figure 15 ) and Tecnis( Figure 17 ) lens, many vacuoles can be seen. After the flash test, Avansee lens ( Figure 16 The hazy appearance of the molten material can be attributed to the formation of numerous very small bubbles. In the 100x photograph, residual droplets are seen, which were not removed to avoid affecting the shiny part inside the material.

[0224] In the case of the Asqelio lens ( Figure 18 ), and bubbles can also be seen. In the 100x photo, residual droplets are seen, which were not forcibly removed to avoid affecting the shiny part inside the material.

[0225] Table 1: Shiny part test results on Examples 1 to 13

[0226]

[0227] Unfolding speed: measured after injection into a 26°C water bath (using a syringe tip with a diameter of 2.2 mm; all lenses were injected with the aid of an ophthalmic viscoelastic solution). Viscosity: observed when a flying saucer-shaped specimen was broken in half; however, no lens tested failed to unfold after injection, so the viscosity can be considered very low in all cases. RI: measured at room temperature using a refractometer (Index Instrument Limited, model CRL 12-70) at a wavelength of 589 nm (all samples were hydrated in demineralized water except Example 13, which was hydrated in a 0.9% NaCl aqueous solution). MTF was measured on a Lamda-X on a PMTF (all samples were hydrated in demineralized water except Example 13, which was hydrated in a 0.9% NaCl aqueous solution).

[0228] Table 2: Shining test results on Comparative Examples 14 to 18

[0229] Example No. Shining Department 14 Some vacuoles 15 Many vacuoles 16 Many vacuoles 17 Some vacuoles and very blurry 18 (It turns white after hydration)

[0230] Table 3: Sparkle Test Results on Selected Commercially Available Lenses

[0231]

[0232] Other comparative examples

[0233] Example 19

[0234] composition parts by weight weight% 2-Phenoxyethyl acrylate 40 31.0 2-Hydroxyethyl Methacrylate 25 19.4 Ethyl acrylate 60 46.5 Ethylene glycol dimethacrylate 4 3.1

[0235] Example 20

[0236] composition parts by weight weight% 2-Phenoxyethyl acrylate 60 50.4 2-Hydroxyethyl Methacrylate 15 12.6 Ethyl acrylate 40 33.6 Ethylene glycol dimethacrylate 4 3.4

[0237] Examples 19 and 20 represent a comparison with the product of US 6140438. As indicated in the document, Examples 4 and 6 of US 6140438 were reproduced. The polymerizable components identified in Tables 19 and 20 were mixed with 1 part by weight of 2,2'-azobis(2,4-dimethylvaleronitrile) as a polymerization initiator per 100 parts by weight of the total amount of polymerizable components, and the mixture was poured into a casting mold having the desired intraocular lens shape. The casting mold was placed in an oven and subjected to thermal polymerization molding at 50°C for 24 hours. The casting mold was then transferred to an air circulation dryer, heated from 65°C to 130°C at a rate of 10°C / hour, and then cooled to room temperature. Thereafter, LED black light irradiation was performed for more than one hour using an irradiation device. Thereafter, the obtained polymer was removed from the casting mold and further dried in an oven at 50°C for 2 days.

[0238] Identically prepared lens compositions were subjected to the curing procedures described in Examples 1-13 instead of the curing procedure described in US 6 140 438. The results were identical for both curing procedures.

[0239] The sparkle test was performed using the rigorous method described in Examples 1-13. The results for the lenses of Examples 19 and 20 are shown in Figures 20 to 21 and are summarized in Table 4.

[0240] Table 4: Shining test results on Comparative Examples 19 and 20

[0241] Example No. Shining Department 19 Some vacuoles and blurry 20 Many vacuoles and very blurry

[0242] As shown in Table 4, the lens material prepared from the intraocular lens composition according to US Pat. No. 6,140,438 contained vacuoles and appeared hazy when viewed under LED light. Thus, even under the soft conditions and short timeframe employed in US Pat. No. 6,140,438, the lens is said to be vacuole-free. More severe conditions, simulating the accelerated aging process under in vivo conditions, indicate that the lens of US Pat. No. 6,140,438 is not, in fact, vacuole-free and becomes hazy. Thus, the performance of the lens material according to US Pat. No. 6,140,438 is significantly worse than that of the lens material according to the present invention, which appears to be vacuole-free and does not become hazy.

Claims

1. An intraocular lens composition comprising a polymer mixture of the following monomers: A short crosslinker comprising two or more (meth)acrylate moieties and a linker located between the two (meth)acrylate moieties, the linker being linked to the (meth)acrylate moieties via an ester group, wherein the longest linear sequence of atoms between the oxygen atom connecting the first (meth)acrylate moiety to the ester group of the linking moiety and the oxygen atom connecting the second (meth)acrylate moiety to the ester group of the linking moiety is 1 to 11 atoms; a long crosslinker comprising two or more (meth)acrylate moieties and a linking moiety located between the two (meth)acrylate moieties, the linking moiety being linked to the (meth)acrylate moieties via an ester group, wherein the longest linear sequence of atoms between an oxygen atom linking a first (meth)acrylate moiety to the ester group of the linking moiety and an oxygen atom linking a second (meth)acrylate moiety to the ester group of the linking moiety is 12 atoms or more and at most 30 atoms; One or more (meth)acrylate monomers of formula (I): in: X is -(C1-C4 alkyl)-O-, -(C1-C4 alkyl)-S-, -(C1-C4 alkyl)-N-, or C1-C8 alkyl, wherein the C1-C8 alkyl includes a cycloalkyl group, and one C atom is substituted by a heteroatom selected from the group consisting of O, S, and N; Y is absent or is -C1-C4 alkyl; n is 1 to 6; R is H or CH3; One or more C1-C4-alkyl (meth)acrylate monomers of formula (II): in: Y is -C1-C4 alkyl; R is H or CH3; or a combination of at least one phenyl C1-C4-alkyl (meth)acrylate of formula (III) and at least one cycloalkyl (meth)acrylate of formula (IV): in: X is absent or is -C1-C4 alkyl; R is H or CH3; in: X is absent and is C1-C5 alkyl or –[(C1-C4 alkyl)-O] n -, where n is 1-8; Y is a C3-C18 alkyl group comprising at least one cycloalkyl moiety, wherein the C3-C18 alkyl group optionally comprises one or more heteroatoms selected from O and N groups; R is H or CH3, The linear sequence of atoms defined for long-chain crosslinkers and short-chain crosslinkers includes C atoms and optionally O atoms and / or N atoms, wherein, if O atoms and N atoms are present, the total number of C atoms exceeds the total number of O atoms and N atoms.

2. The intraocular lens composition according to claim 1, wherein X is -(C1-C4 alkyl)-O-; Y is -C1-C4 alkyl.

3. The intraocular lens composition according to claim 1 or 2, wherein: Based on the total monomer mixture, the amount of short crosslinkers is 0.1-12% by weight, and / or the amount of long crosslinkers is 0.5-25% by weight, and / or the amount of one or more (meth)acrylate monomers of formula (I) is 10-90% by weight, and / or the amount of one or more C1-C4-alkyl (meth)acrylate monomers of formula (II) or a combination of phenyl-C1-C4-alkyl (meth)acrylate of formula (III) and cycloalkyl (meth)acrylate of formula (IV) is 5-70% by weight.

4. The intraocular lens composition according to any one of claims 1 to 3, wherein Short crosslinkers include ethylene glycol di(meth)acrylate, or trimethylolpropane tri(meth)acrylate, or tetra(ethylene glycol) di(meth)acrylate, or di(ethylene glycol) di(meth)acrylate, or tri(propylene glycol) di(meth)acrylate, or tri(ethylene glycol) di(meth)acrylate.

5. The intraocular lens composition according to any one of claims 1 to 4, wherein Long crosslinkers include poly(ethylene glycol) di(meth)acrylate or poly(propylene glycol) di(meth)acrylate.

6. The intraocular lens composition according to any one of claims 1 to 5, wherein The one or more (meth)acrylate monomers of formula (I) include: di(ethylene glycol) ethyl ether acrylate, or 2-methoxyethyl acrylate, or 2-methoxyethyl methacrylate, or di(ethylene glycol) methyl ether methacrylate, or tetrahydrofuranyl acrylate, or triethylene glycol methyl ether methacrylate or a mixture thereof.

7. The intraocular lens composition according to any one of claims 1 to 6, wherein One or more C1-C4-alkyl(meth)acrylate monomers of formula (II) include: butyl methacrylate, or ethyl methacrylate, or propyl methacrylate, or tert-butyl acrylate, or methyl methacrylate, or phenyl-C1-C4-alkyl(meth)acrylate of formula (III) includes: phenyl methacrylate, or benzyl acrylate, or benzyl methacrylate, or 2-phenylethyl acrylate, or 2-phenylethyl methacrylate, and cycloalkyl(meth)acrylate of formula (IV) includes: cyclohexyl acrylate, or isobornyl methacrylate, or cyclohexyl methacrylate, or 1-adamantyl methacrylate, or isobornyl methacrylate.

8. The intraocular lens composition according to any one of claims 1 to 7, comprising a polymer mixture of: (a) 5-40 wt% phenyl methacrylate, preferably 22±5 wt% 10-55 wt% cyclohexyl acrylate, preferably 29±5 wt% 15-55 wt% di(ethylene glycol) ethyl ether acrylate, preferably 38±5 wt% 1-20 wt% of poly(ethylene glycol) diacrylate having a molecular weight of 250-5000 Da, preferably 400-1000 Da, preferably 7±5 wt% 2-10 wt% trimethylolpropane triacrylate, preferably 4±2 wt% or (b) 5-80 wt% butyl methacrylate, preferably 68±5 wt% 3-45 wt% di(ethylene glycol) ethyl ether acrylate, preferably 20±5 wt% 1-15 wt% of poly(ethylene glycol) diacrylate having a molecular weight of 250-1800 Da, preferably 400-1000 Da, preferably 8±5 wt% 0.1-8 wt% tri(propylene glycol) diacrylate, preferably 4±2 wt% or (c) 5-65 wt% benzyl acrylate, preferably 16±5 wt% 5-75 wt% isobornyl methacrylate, preferably 30±5 wt% 15-80 wt% di(ethylene glycol) ethyl ether acrylate, preferably 45±5 wt% 1-15 wt% of poly(ethylene glycol) dimethacrylate having a molecular weight of 250-5000 Da, preferably 400-2500 Da, preferably 6±5 wt% 0.1-8 wt% ethylene glycol dimethacrylate, preferably 4±2 wt% or (d) 1-60 wt% ethyl methacrylate, preferably 30±5 wt% 3-75 wt% methoxyethyl acrylate and / or 2-85 wt% methoxyethyl methacrylate, preferably 52±5 wt% methoxyethyl acrylate and 9±5 wt% methoxyethyl methacrylate 1-15 wt% of poly(ethylene glycol) diacrylate having a molecular weight of 200-5000 Da, preferably 200-1000 Da, preferably 5±2 wt% 0.1-8 wt% ethylene glycol dimethacrylate, preferably 5±2 wt% or (e) 5-75 wt% benzyl methacrylate, preferably 31±5 wt% 25-75 wt% cyclohexyl acrylate, preferably 15±5 wt% 15-80 wt% di(ethylene glycol) methyl ether methacrylate, preferably 48±5 wt% 1-15 wt% of poly(ethylene glycol) dimethacrylate having a molecular weight of 250-5000 Da, preferably 400-1600 Da, preferably 4±2 wt% 0.1-8 wt% trimethylolpropane triacrylate, preferably 2±1 wt% or (f) 1-65 wt% propyl methacrylate, preferably 22±5 wt% 5-85 wt% 2-(2-methoxyethoxy)ethyl methacrylate, preferably 70±5 wt% 1-15 wt% of poly(propylene glycol) diacrylate having a molecular weight of 230-2000 Da, preferably 400-1600 Da, preferably 5±2 wt% 0.1-8 wt% trimethylolpropane trimethacrylate, preferably 3±2 wt% or (g) 1-55 wt% 2-phenylethyl acrylate, preferably 10±5 wt% 3-65 wt% cyclohexyl methacrylate, preferably 33±5 wt% 15-90 wt% 2-methoxyethyl acrylate, preferably 45±5 wt% 1-15 wt% of poly(ethylene glycol) diacrylate having a molecular weight of 200-5000 Da, preferably 200-1600 Da, preferably 8±5 wt% 0.1-8 wt% ethylene glycol dimethacrylate, preferably 4±2 wt% or (h) 1-70 wt% tert-butyl acrylate, preferably 52±5 wt% 3-75 wt% tetrahydrofuran acrylate, preferably 35±5 wt% 1-15 wt% of poly(ethylene glycol) diacrylate having a molecular weight of 200-2000 Da, preferably 400-1000 Da, preferably 9±5 wt% 0.1-8 wt% tri(ethylene glycol) dimethacrylate, preferably 3±2 wt% or (i) 1-55 wt% benzyl acrylate, preferably 17±5 wt% 2-45 wt% 1-adamantyl methacrylate, preferably 25±5 wt% 15-80 wt. % triethylene glycol methyl ether methacrylate and / or 2-45 wt. % 2-ethoxyethyl methacrylate, preferably 37±5 wt. % triethylene glycol methyl ether methacrylate and 17±5 wt. % 2-ethoxyethyl methacrylate 1-15 wt% of poly(ethylene glycol) diacrylate having a molecular weight of 200-5000 Da, preferably 200-1600 Da, preferably 3±2 wt% 0.1-8 wt% trimethylolpropane triacrylate, preferably 3±2 wt% or (j) 1-75 wt% ethyl methacrylate, preferably 22±5 wt% 2-75% by weight of 2-methoxyethyl acrylate and / or 2-75% by weight of 2-ethoxyethyl methacrylate, preferably 23±5% by weight of 2-methoxyethyl acrylate and 44±5% by weight of 2-ethoxyethyl methacrylate 1-15 wt% of poly(ethylene glycol) dimethacrylate having a molecular weight of 200-2000 Da, preferably 200-1000 Da, preferably 9±5 wt% 0.1-8 wt% tetra(ethylene glycol) dimethacrylate, preferably 2±1 wt% or (k) 1-55 wt% 2-phenylethyl methacrylate, preferably 27±5 wt% 2-55 wt% isobornyl methacrylate, preferably 14±5 wt% 15-80 wt% 2-methoxyethyl acrylate, preferably 48±5 wt% 1-15 wt% of poly(ethylene glycol) diacrylate having a molecular weight of 200-5000 Da, preferably 200-1600 Da, preferably 7±5 wt% 0.1-8 wt% ethylene glycol dimethacrylate, preferably 4±2 wt% or (l) 1-65 wt% methyl methacrylate, preferably 27±5 wt% 10-85 wt% 2-(2-methoxyethoxy)ethyl methacrylate, preferably 65±5 wt% 1-15 wt% of poly(propylene glycol) diacrylate having a molecular weight of 230-2000 Da, preferably 400-1500 Da, preferably 4±2 wt% 0.1-8 wt% tetra(ethylene glycol) diacrylate, preferably 4±2 wt% or (m) 1-55 wt% 2-phenylethyl acrylate, preferably 8±5 wt% 2-45 wt% 1-adamantyl methacrylate, preferably 30±5 wt% 5-80 wt% 2-methoxyethyl acrylate and / or 2-75 wt% di(ethylene glycol) ethyl ether acrylate, preferably 16±5 wt% 2-methoxyethyl acrylate and 35±5 wt% di(ethylene glycol) ethyl ether acrylate 1-15 wt% of poly(ethylene glycol) dimethacrylate having a molecular weight of 200-5000 Da, preferably 200-1600 Da, preferably 8±5 wt% 0.1-8 wt% di(ethylene glycol) dimethacrylate, preferably 3±2 wt%.

9. An artificial lens, an artificial cornea, a corneal ring, a corneal implant or a corneal inlay, comprising the artificial lens composition according to any one of claims 1 to 8.

10. A method for preparing the intraocular lens composition according to any one of claims 1 to 8, the method comprising the following steps: 1) preparing a monomer mixture as claimed in any one of claims 1 to 8; 2) preferably adding a free radical polymerization initiator; 3) allowing polymerization of the monomer mixture; 4) Optionally, extraction is performed to remove any by-products and / or residual unreacted monomers.

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