Ophthalmic composition having multiple comonomer groups and ophthalmic lens

Abstract

The present invention relates to an ophthalmic composition for producing an ophthalmic lens (10) comprising comonomer groups A) to C), at least one comonomer group being D), E) or a mixture thereof, and at least one cross-linking agent F). Here: A) represents at least one (meth) acrylate having at least one aromatic group; b) represents at least one (meth) acrylate having an aliphatic or non-aromatic cyclic or non-aromatic heterocyclic group; c) represents at least one (meth) acrylate having at least one hydroxyl group; d) represents at least one (meth) acrylamide having an aromatic group and having an aliphatic or non-aromatic cyclic or non-aromatic heterocyclic group; and E) represents a mixture of at least one (meth) acrylamide having two aromatic groups and at least one (meth) acrylamide having two aliphatic and / or non-aromatic cyclic and / or non-aromatic heterocyclic groups. Each of the comonomer sets comprises components respectively determined based on the total weight of the ophthalmic composition. The invention also relates to an ophthalmic lens (10) which is at least partially produced from such an ophthalmic composition.

Description

Technical Field

[0001] The present invention relates to an ophthalmic composition having two or more comonomer groups and to an ophthalmic lens, in particular a soft intraocular lens, produced at least in part from such an ophthalmic composition. Prior art

[0002] In recent decades, a wide variety of different biomaterials suitable for the production of ophthalmic compositions and lenses, especially intraocular lenses (IOLs), have been developed. The different classes of materials include hydrophilic polymers, hydrophobic polymers and silicones. Each class has its own advantages and disadvantages. Although silicone IOLs have very good resistance to post-cataract (PCO), their unfolding behavior after injection may be uncontrollable. Hydrophilic lenses generally show very good biocompatibility, but also show higher PCO and calcification rates. In recent years, hydrophobic IOLs have grown the fastest. They are usually in n D =1.44-1.55 range provides a relatively high refractive index, but with the risk of "flare", which is characterized by aqueous microbubbles that form within the polymer matrix and can disrupt the patient's visual perception, especially with multifocal lenses. Vacuoles with a diameter of less than 200 nm up to 120 μm below the IOL surface are also called "nanoflare" (subsurface nanoflare, SSNG).

[0003] US2002 / 0049290 A1 discloses an optically transparent hydrogel having a high refractive index and an intraocular lens made therefrom. Preferred hydrogels have a refractive index of 1.45 or higher and a water content of about 5 to 30 weight percent.

[0004] WO 99 / 58507A1 discloses hydrophilic, UV light absorbing polymerizable monomers. These monomers are copolymerizable and produce biocompatible hydrogels that can absorb at least 90% of UV light incident on the hydrogel. Such hydrogels are optically transparent, have a high refractive index and have long-term stability.

[0005] US 2013 / 0231740 A1 discloses relatively soft, optically transparent, foldable materials with a high refractive index, which are particularly suitable for use in the manufacture of intraocular lenses, contact lenses and other eye implants.

[0006] In order to tailor the material for such a specific application as an ophthalmic lens, a complex multi-parameter optimization has to be performed. In addition to ensuring biocompatibility, optical, physical and mechanical properties have to be optimized simultaneously. For example, a material with excellent biocompatibility but at the same time low flexibility is not ideal, since this would result in a larger incision for IOL implantation. This is particularly important since the aim is to make the incisions smaller (micro-incision cataract surgery, MICS with incisions <2 mm). The choice of matrix material is particularly important here. Hydrophobic polymers inherently offer good matrix properties for the development of MICS-compatible materials, i.e. a combination of high tensile strength with a high refractive index. However, flare resistance and material flexibility have to be significantly improved. A new class of materials, called "neo-hydrophobic acrylates", is the result of recent research in the field of IOL materials. Table 1 below gives an overview of the current standard material categories.

[0007] Table 1: Physical properties of standard IOL materials

[0008]

[0009] "Hyg." represents the mass percentage of water in the lens at equilibrium at 35°C, "contact angle" is the angle between the leading edge of a water droplet and the surface of the material, "tensile strength" is the maximum stress that a material class can withstand without breaking when stretched, "refractive index n" represents the refractive index at 20°C, and "Tg" represents the glass transition temperature.

[0010] Hydrophilic materials generally have a low refractive index, which actually decreases further when they are fully hydrated. Therefore, the lens curvature and thickness must necessarily be more significant at high diopters than in the case of materials with a higher refractive index. This requires implanting a large lens cross-section through a small injection tip, which increases the risk of damage to the cartridge tip of the implantation tool or the lens itself. In the case of these materials, a higher material flexibility can be obtained through a high water absorption rate of 5 to 30 percent. However, this not only significantly reduces the refractive index, but also requires the lens to be stored in an aqueous or at least moisture-controlled packaging. Otherwise, it is impossible to ensure dimensional accuracy and optical quality after lens implantation.

[0011] The main idea of ​​the "new hydrophobic acrylates" is to add the hydrophilic monomer HEMA (2-hydroxyethyl methacrylate) to the originally hydrophobic comonomer, since this has the ability to disperse water throughout the material. Known ophthalmic compositions contain about 30% HEMA in order not to flare, and about 4% by weight of the balance water. Due to the latter proportion, the corresponding IOLs must be stored in 0.9% saline solution and are therefore not suitable for dry preloaded IOL implantation systems.

[0012] In the case of some "new hydrophobic acrylates", the risk of flare is said to be reduced, but with a relatively low refractive index n d <1.5. This means, as already mentioned, that the cross section of the lens and therefore also the required cutting size must be significantly increased depending on the diopter. In addition, these materials have a relatively slow unfolding speed of the lens under simulated operating conditions (26°C water bath) and are not suitable for steam sterilization, which severely limits the choice of sterilization procedures, which are mandatory for ophthalmic implants.

[0013] Thus, recent developments in the field of IOL biomaterials point to interesting directions for further development, but improvements are still needed for implants that offer a faster and less invasive surgical procedure combined with greater patient satisfaction. Summary of the invention

[0014] The object of the present invention is therefore to provide an ophthalmic composition which enables the production of a flexible, biocompatible ophthalmic lens having a high refractive index and the lowest possible risk of flare, wherein the ophthalmic lens produced from the composition is storable dry and sterilizable by steam sterilization. Another object of the present invention is to indicate a corresponding ophthalmic lens.

[0015] These objects are achieved according to the invention by an ophthalmic composition having the features of claim 1 and an ophthalmic lens according to claim 6. Advantageous configurations with suitable developments of the invention are indicated in the respective dependent claims; advantageous configurations of the ophthalmic composition are to be regarded as advantageous configurations of the ophthalmic lens and vice versa.

[0016] A first aspect of the invention relates to an ophthalmic composition for producing an ophthalmic lens, comprising comonomer groups A) to C), at least one comonomer group which is D), E) or a mixture thereof, and at least one crosslinker F). In this context, A) represents at least one (meth)acrylate having at least one aromatic group; B) represents at least one (meth)acrylate having an aliphatic or non-aromatic cyclic or non-aromatic heterocyclic group; C) represents at least one (meth)acrylate having at least one hydroxyl group; D) represents at least one (meth)acrylamide having an aromatic group and having an aliphatic or non-aromatic cyclic or non-aromatic heterocyclic group, and E) represents a mixture of at least one (meth)acrylamide having two aromatic groups and at least one (meth)acrylamide having two aliphatic and / or non-aromatic cyclic and / or non-aromatic heterocyclic groups. In other words, it is envisaged according to the invention that the ophthalmic composition comprises monomers from at least four or five different molecular classes A), B), C), D) or A), B), C), E) or A), B), C), D), E) and at least one crosslinking agent F), or in the simplest form consists of the mentioned molecular classes and does not contain any other molecular classes. The composition of the invention is preferably free of silicon and / or free of siloxane and preferably free of fluorinated compounds. The molecular classes A) to E) act as comonomers in the polymer synthesized from the ophthalmic composition of the invention and can be crosslinked with the aid of the crosslinking agent F). Therefore, the composition of the invention can also be referred to as a prepolymer. In the context of the present disclosure, in the absence of any explicit discussion of a specific individual compound, the term "(meth)acrylate" is always used to refer to acrylates, methacrylates and any mixtures thereof. For example, the expression "2-phenylethyl (meth)acrylate" covers the compounds 2-phenylethyl acrylate, 2-phenylethyl methacrylate and any mixture of these two compounds. The same applies to the expression "(meth)acrylamide", which, in the absence of any explicit discussion of a specific individual compound, always covers acrylamide, methacrylamide or a mixture thereof. Generally, in the context of the present disclosure, "a / an" should be understood as an indefinite article, that is, in the absence of any clear contrary indication, it is always understood as "at least one". On the contrary, "a / an" can also be understood as "only one".

[0017] The ophthalmic composition of the present invention is particularly suitable for the production of soft MICS-compatible intraocular lenses, but in principle can also be used to produce other ophthalmic lenses, implants, artificial corneas, inlays, etc. At the same time, the composition of the present invention enables the production of ophthalmic lenses that provide high patient satisfaction due to their very low tendency to flare. The surgical operation of implantation can be improved by the rapid, controllable deployment speed of the lens made of the composition. The ophthalmic composition of the present invention also allows the production of ophthalmic lenses that can be used in a fully pre-filled syringe system with dry and wet storage. This reduces manufacturing complexity and facilitates storage while maintaining complete design freedom. Finally, the ophthalmic composition of the present invention or the lens produced therefrom can be sterilized by steam sterilization. Compared with the established ethylene oxide (EtO) sterilization of standard hydrophobic IOLs, this not only opens up a wider range of production processes, but also uses a more sustainable and less costly method.

[0018] The present invention is based on the discovery that in order to design a polymeric biomaterial combining all of the above requirements (if possible), what is required is an ophthalmic composition containing at least four different classes of monomers or comonomers, each having different properties.

[0019] The first group A) may also be referred to as "aromatic monomers" and contain at least one aromatic group or aromatic ring in order to increase the refractive index of the resulting polymer. The term "aromatic ring" includes both individual rings (e.g. phenyl) and fused and separated aromatic ring systems (e.g. naphthyl or biphenyl rings). The aromatic rings may each carry one or more substituents. The aromatic rings are preferably selected from C 6-18 -Aryl.

[0020] The second group B) comprises monomers with aliphatic groups, which can be used to increase the flexibility of the material. Alternatively or in addition to the open-chain aliphatic groups, one or more non-aromatic cyclic groups, such as cyclohexyl, and / or one or more non-aromatic heterocyclic groups, such as piperidinyl, can also be provided. The aliphatic groups are preferably selected from C 1-12 -alkyl, these alkyl groups are preferably unbranched or - as far as possible - branched. The heterocyclic group preferably has at least one atom from the group of N, S and / or O and is suitable for forming hydrogen bonds. The aliphatic group is preferably straight-chain, but in principle can also be branched. In addition, each aliphatic non-aromatic cyclic or non-aromatic heterocyclic group can also contain one or more carbon double bonds and / or triple bonds.

[0021] The third group C) contains one or more monomers having at least one hydroxyl group. These are preferably one or more terminal or sterically unhindered hydroxyl groups, which are able to form hydrogen bonds in the polymer. The third group C) is added mainly to increase the water absorption of the polymer composition.

[0022] A fourth group D) contains "mixed" (meth)acrylamide comonomers which lead to unexpected improvements in the properties of the resulting biomaterials. Molecular class D), defined here as "mixed" (meth)acrylamide comonomers, comprises a vinyl functional group and a tertiary amide for polymerization. The advantage of using acrylamide over acrylates is that two terminal substituents can be attached per monomer unit. In the case of "mixed" acrylamides, the two substituents or functional groups in group D) are different. The comonomers of group D) thus have the general formula (I)

[0023]

[0024] Where R 1 =H / CH3, R 2 = an aromatic group and R 3 = alkyl, where R 2 and / or R 3 Preferably unsubstituted. Two substituents R are selected 2 and R 3 Such that they preferably have chemical structures identical or very similar to those of the aromatic monomers A) or aliphatic monomers B) used in the ophthalmic composition in question. Therefore, generally, the same considerations and restrictions as the substituents of the comonomers of groups A) and B) apply to the substituents of the comonomers of group D). These structural similarities lead to favorable intermolecular interactions between the different comonomer groups A), B) and D) in the latter polymer, because acrylamide D) acts as a medium between groups A) and B). The aromatic groups of acrylamide D) also advantageously lead to an increase in the refractive index and form π-π interactions with the molecules of the aromatic monomer A), which leads to higher structural strength of the polymer. The alkyl groups of acrylamide D) can increase the flexibility of the material, or in the case of branched or cyclic / heterocyclic substituents, also provide higher light resistance and tear resistance. In certain embodiments, R in formula (I) 3 Alternatively, it may be substituted, in particular, by one or more hydroxyl groups. In this way, it is possible for comonomer D) to be structurally similar to comonomer C) and thus for favorable intermolecular interactions to develop between groups A), C) and D).

[0025] Alternatively or in addition to group D), group E) can also be used. Therefore, the two groups D) and E) are used synonymously below. Group E) comprises a mixture of at least two different (meth)acrylamides, wherein the first (meth)acrylamide has two aromatic groups and the second (meth)acrylamide has two aliphatic and / or non-aromatic cyclic and / or non-aromatic heterocyclic groups. In other words, group E) comprises two molecular species of the general formulae IIa and IIb:

[0026]

[0027] Wherein, in Formula IIa, R 1 =H / CH3 and R 2 and R 3 = an aromatic group, and in Formula IIb, R 1 =H / CH3 and R 2 and R 3 = alkyl, where R 2 and R 3 are independently unsubstituted and / or substituted, in particular, by one or more hydroxyl groups, in order to be able to interact with the comonomers of group C). Thus, the two substituents R of (meth)acrylamide 2 , R 3 can be identical or different. Otherwise, the same considerations and restrictions as for the substituents of groups A), B) and C) apply to the substituents of group E). Compared to group D), group E) therefore does not cover intramolecular "mixed" (meth)acrylamides, but rather "mixed" mixtures of at least two different (meth)acrylamides, wherein the mixture E) can also serve as a medium between group A) and B) or C) in the polymer. Compared to the mixed compounds of group D), some individual compounds of group E) can be synthesized more easily and in a cheaper manner, especially when the individual (meth)acrylamides each carry two identical substituents R 2 , R 3 hour.

[0028] In order to produce an elastomeric biocompatible polymer suitable for use as a soft IOL and preferably not thermoplastic, finally, at least one crosslinking agent F) is provided, which is designed to produce covalent bonds between the polymer chains, which ensure reliable unfolding and provide a balance between material thickness and flexibility. Two or more different crosslinking agents may also be provided in order to specifically adjust the mechanical properties of the polymer.

[0029] Since polymer chains generally contain more dense regions and more loosely folded other regions, regions with lower density can lead to local accumulation of water, especially when environmental conditions change rapidly (for example in the case of temperature shock). The present invention is therefore also based on the finding that this risk can be significantly reduced by using flexible substituents that can be freely oriented. This is particularly true for the unsubstituted or substituted alkyl groups that are provided or can be provided in comonomer groups B), C), D) and E).

[0030] On the other hand, it has also been recognized that it is very important to use hydrophilic or hygroscopic comonomers which are distributed with maximum homogeneity in the polymer matrix. These comonomers according to group C) not only stabilize water locally by forming hydrogen bonds, but also form non-covalent bonds with the functional groups of the amides (group D) / E)), which leads to a higher structural strength of the polymer.

[0031] According to the invention, the proportion of comonomer group A) is between 30% by weight and 60% by weight, based on the total weight of the ophthalmic composition, and is therefore, for example, 30% by weight, 31% by weight, 32% by weight, 33% by weight, 34% by weight, 35% by weight, 36% by weight, 37% by weight, 38% by weight, 39% by weight, 40% by weight, 41% by weight, 42% by weight, 43% by weight, 44% by weight, 45% by weight, 46% by weight, 47% by weight, 48% by weight, 49% by weight, 50% by weight, 51% by weight, 52% by weight, 53% by weight, 54% by weight, 55% by weight, 56% by weight, 57% by weight, 58% by weight, 59% by weight, 60% by weight, 61% by weight, 62% by weight, 63% by weight, 64% by weight, 65% by weight, 66% by weight, 67% by weight, 68% by weight, 69% by weight, 70% by weight, 71% by weight, 72% by weight, 73% by weight, 74% by weight, 75% by weight, 76% by weight, 77% by weight, 78% by weight, 79% by weight, 80% by weight, 81% by weight, 42% by weight, 43% by weight, 44% by weight, 45% by weight, 46% by weight, 47% by weight, 48% by weight, 49% by weight, 50% by weight, 51% by weight, 52% by weight, 53% by weight, 54% by weight, 55% by weight, 56% by weight, 57% by weight, 58% by weight, 59% by weight or 60% by weight. The proportion of comonomer group B) is between 10% by weight and 45% by weight and is therefore, for example, 10% by weight, 11% by weight, 12% by weight, 13% by weight, 14% by weight, 15% by weight, 16% by weight, 17% by weight, 18% by weight, 19% by weight, 20% by weight, 21% by weight, 22% by weight, 23% by weight, 24% by weight, 25% by weight, 26% by weight, 27% by weight, 28% by weight, 29% by weight, 30% by weight, 31% by weight, 32% by weight, 33% by weight, 34% by weight, 35% by weight, 36% by weight, 37% by weight, 38% by weight, 39% by weight, 40% by weight, 41% by weight, 42% by weight, 43% by weight, 44% by weight, 45% by weight, 46% by weight, 47% by weight, 48% by weight, 49% by weight, 50% by weight, 51% by weight, 52% by weight, 53% by weight, 54% by weight, 55% by weight, 56% by weight, 57% by weight, 58% by weight, %, 26% by weight, 27% by weight, 28% by weight, 29% by weight, 30% by weight, 31% by weight, 32% by weight, 33% by weight, 34% by weight, 35% by weight, 36% by weight, 37% by weight, 38% by weight, 39% by weight, 40% by weight, 41% by weight, 42% by weight, 43% by weight, 44% by weight or 45% by weight. The proportion of comonomer group C) is between 5% by weight and 30% by weight and is therefore, for example, 5% by weight, 6% by weight, 7% by weight, 8% by weight, 9% by weight, 10% by weight, 11% by weight, 12% by weight, 13% by weight, 14% by weight, 15% by weight, 16% by weight, 17% by weight, 18% by weight, 19% by weight, 20% by weight, 21% by weight, 22% by weight, 23% by weight, 24% by weight, 25% by weight, 26% by weight, 27% by weight, 28% by weight, 29% by weight or 30% by weight.The proportion of the sum of comonomer groups D) and E) is between 1% by weight and 14% by weight and is therefore, for example, 1% by weight, 2% by weight, 3% by weight, 4% by weight, 5% by weight, 6% by weight, 7% by weight, 8% by weight, 9% by weight, 10% by weight, 11% by weight, 12% by weight, 13% by weight or 14% by weight. The proportion of crosslinkers F) is not more than 5% by weight and is therefore, for example, 0.05% by weight, 0.1% by weight, 0.2% by weight, 0.3% by weight, 0.4% by weight, 0.5% by weight, 0.6% by weight, 0.7% by weight, 0.8% by weight, 0.9% by weight, 1.0% by weight, 1.1% by weight, 1.2% by weight, 1.3% by weight, 1.4% by weight, 1.5% by weight, 1.6% by weight, 1.7% by weight, 1.8% by weight, 1.9% by weight, 2.0% by weight, 2.1% by weight, 2.2% by weight, 2.3% by weight, % by weight, 2.4% by weight, 2.5% by weight, 2.6% by weight, 2.7% by weight, 2.8% by weight, 2.9% by weight, 3.0% by weight, 3.1% by weight, 3.2% by weight, 3.3% by weight, 3.4% by weight, 3.5% by weight, 3.6% by weight, 3.7% by weight, 3.8% by weight, 3.9% by weight, 4.0% by weight, 4.1% by weight, 4.2% by weight, 4.3% by weight, 4.4% by weight, 4.5% by weight, 4.6% by weight, 4.7% by weight, 4.8% by weight, 4.9% by weight or 5.0% by weight. The proportion of crosslinkers F) is preferably between 0.5% by weight and 5% by weight.

[0032] The (meth)acrylamide comonomers D) / E) are preferably used as a kind of "additive" in the ophthalmic composition. This means that the sum of (meth)acrylamide D) / E) in % by weight is preferably minimal compared to the remaining comonomer types A) to C) in the composition. It will be understood that the proportions of all components of the ophthalmic composition always and exclusively add up to 100% by weight. Generally, percentages in the context of the present disclosure should be considered as mass percentages unless otherwise stated.

[0033] In an advantageous configuration of the invention, comonomer group A) comprises or is 2-phenylethyl acrylate, 2-phenylethyl methacrylate, ethylene glycol phenyl ether acrylate, ethylene glycol phenyl ether methacrylate or a mixture thereof. Alternatively or additionally, comonomer group B) comprises or is butyl acrylate, butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate or a mixture thereof. Alternatively or additionally, comonomer group C) comprises or is 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate or a mixture thereof. Alternatively or additionally, comonomer group D) comprises or is N-benzyl-N-isopropylacrylamide, N-benzyl-N-isopropylmethacrylamide, N-benzyl-N-butylacrylamide, N-benzyl-N-butylmethacrylamide, N-benzyl-N-isobutylacrylamide, N-benzyl-N-isobutylmethacrylamide, N-benzyl-N-isoamylacrylamide, N-benzyl-N-isoamylmethacrylamide, N-benzyl-N-amylacrylamide, N-benzyl-N-amylmethacrylamide, N-benzyl-N-methylmethacrylamide or a mixture thereof. Alternatively or additionally, comonomer group E) comprises or is N,N-dibenzyl(meth)acrylamide and N,N-diisopropyl(meth)acrylamide, N,N-dibenzyl(meth)acrylamide and N,N-dibutyl(meth)acrylamide, N,N-dibenzyl(meth)acrylamide and N,N-diisobutyl(meth)acrylamide, N,N-dibenzyl(meth)acrylamide, N,N-diisopentyl(meth)acrylamide and N,N-dipentyl(meth)acrylamide, N,N-dibenzyl(meth)acrylamide and N,N-dimethyl(meth)acrylamide or mixtures thereof. Alternatively or additionally, F) comprises or is a crosslinker having at least two acrylate groups, at least two methacrylate groups or at least one acrylate and at least one methacrylate group, wherein the crosslinker in particular comprises or is butane-1,4-diol diacrylate and / or ethylene glycol dimethacrylate. Such ophthalmic compositions are particularly suitable for producing transparent ophthalmic biomaterials having a favorable refractive index n in a hydrated state of about 1.50 or greater. D,35 ℃, a Shore A hardness of less than 80 (t=3s) or a Shore A hardness of less than 50 (t=10min), a glass transition temperature between 0℃ and 15℃, a water absorption capacity between 0.5% by weight and 3.5% by weight at 35℃, and an Abbe number of at least 30.

[0034] Regarding the Shore A hardness values, it should be noted that these can be determined within the scope of the present disclosure at different indentation times t. The indentation times t are each included within the scope of the present disclosure. Typically, the measurement of elastomers (e.g., rubber) is performed after 3 seconds as defined in DIN ISO 7619-1. The DIN-compliant Shore A limit value of the material of the present invention is preferably a maximum of 80 or less (t=3s), preferably a maximum of 65 or less (t=3s). Alternatively or additionally, at an indentation time of t=10min, the Shore A value is at most 50 or less.

[0035] A further advantage is that the ophthalmic composition comprises at least one further component G), H), I) or a mixture thereof, wherein G) represents at least one UV absorber, preferably covalently bondable, H) represents at least one dye, preferably covalently bondable, for modifying the light absorption properties, and I) represents a polymerization initiator. With the aid of component G), preferably UV absorption properties can be provided at least in the wavelength range between about 300 nm and about 400 nm. With the aid of component H) (which can also be referred to as yellow dye), the ophthalmic composition can be easily adapted to provide yellow biomaterial for the production of a lens having, for example, an absorption maximum in the wavelength range between about 400 nm and about 500 nm. The amount of yellow dye used in the composition can be selected as required within a relatively wide concentration range in order to obtain the desired transmission percentage at each wavelength in the range between about 400 nm and about 500 nm. It is also possible to achieve the desired absorption properties of the biomaterial or the lens produced therefrom in the wavelength range visible to humans by one or more of components G) and / or H), preferably covalently bonded in the reacted polymer in order to avoid external diffusion. By means of polymerization initiators, it is possible to adjust the nature and the speed of the polymerization reaction of the ophthalmic composition.

[0036] Further advantages with regard to the various properties of the ophthalmic composition and the biomaterial formed therefrom result from the fact that the proportion of component G) does not exceed 2% by weight, i.e., for example, 0.1% by weight, 0.2% by weight, 0.3% by weight, 0.4% by weight, 0.5% by weight, 0.6% by weight, 0.7% by weight, 0.8% by weight, 0.9% by weight, 1.0% by weight, 1.1% by weight, 1.2% by weight, 1.3% by weight, 1.4% by weight, 1.5% by weight, 1.6% by weight, 1.7% by weight, 1.8% by weight, 1.9% by weight or 2.0% by weight, in particular 2.0% by weight. It is not more than 1% by weight, and / or the proportion of component H) is not more than 5% by weight, i.e. for example 0.1% by weight, 0.2% by weight, 0.3% by weight, 0.4% by weight, 0.5% by weight, 0.6% by weight, 0.7% by weight, 0.8% by weight, 0.9% by weight, 1.0% by weight, 1.1% by weight, 1.2% by weight, 1.3% by weight, 1.4% by weight, 1.5% by weight, 1.6% by weight, 1.7% by weight, 1.8% by weight, 1.9% by weight, 2.0% by weight, 2.1% by weight, 2.2% by weight, 2.3% by weight, 2.4% by weight. %, 2.5% by weight, 2.6% by weight, 2.7% by weight, 2.8% by weight, 2.9% by weight, 3.0% by weight, 3.1% by weight, 3.2% by weight, 3.3% by weight, 3.4% by weight, 3.5% by weight, 3.6% by weight, 3.7% by weight, 3.8% by weight, 3.9% by weight, 4.0% by weight, 4.1% by weight, 4.2% by weight, 4.3% by weight, 4.4% by weight, 4.5% by weight, 4.6% by weight, 4.7% by weight, 4.8% by weight, 4.9% by weight or 5.0% by weight, and / or the proportion of component I) by weight % by weight, 1.6 % by weight, 1.7 % by weight, 1.8 % by weight, 1.9 % by weight, 2.0 % by weight, 2.1 % by weight, 2.2 % by weight, 2.3 % by weight, 2.4 % by weight, 2.5 % by weight, 2.6 % by weight, 2.7 % by weight, 2.8 % by weight, 2.9 % by weight, 3.0 % by weight, 3.1 % by weight, 3.2 % by weight, 3.3 % by weight, 3.4 % by weight, 3.5 % by weight, 3.6 % by weight, 3.7 % by weight, 3.8 % by weight, 3.9 % by weight, 4.0 % by weight, 4.1 % by weight, 4.2 % by weight, 4.3 % by weight, 4.4 % by weight, 4.5 % by weight, 4.6 % by weight, 4.7 % by weight, 4.8 % by weight, 4.9 % by weight,7% by weight, 2.8% by weight, 2.9% by weight or 3.0% by weight. .

[0037] It has also been found that it is advantageous when the UV absorber G) is 2-(5-chloro-2H-benzotriazole-2-yl)-6-(1,1-dimethylethyl)-4-vinylphenol (UVAM). Alternatively or additionally, it has been found that it is advantageous when the dye H) is the yellow dye 4-(3-vinylphenylazo) diphenylamine (3VPADPA or VPAD). Since the yellow dye absorbs in the range between 400nm and 500nm, it is also referred to as a "blue light absorber". These compounds, alone or in any combination, allow the production of biomaterials with absorption properties particularly advantageous for ophthalmic lenses in the wavelength range between about 300nm and 400nm (G)) or between about 400nm and about 500nm (H)). In other words, the combination of UV and blue light absorbers (G), H)) can be used to adjust the absorption properties in a specified wavelength range as required. In this way, the level of high-energy blue light is reduced. If no blue light absorber (H)) is added and only UV absorbers (G)) are used, the cut-off value for absorption is preferably set at about 400 nm and the biomaterial according to the invention remains colorless with maximum UV protection.

[0038] The second aspect of the present invention relates to an ophthalmic lens made at least in part of an ophthalmic composition according to the first aspect of the present invention. The ophthalmic lens is in particular a soft intraocular lens. In a particular embodiment, the lens may have an optical part and a haptic part. The lens may also consist of two or more different biomaterials, at least one of which is according to the present invention. The entire lens is preferably produced by one or more compositions of the present invention or the biomaterial of the present invention. Therefore, in some embodiments, the lens may have two or more regions with different optical, physical and / or mechanical properties. However, it is also possible that the ophthalmic lens is designed as a contact lens. The ophthalmic lens according to the second aspect of the present invention is realized by using an ophthalmic composition according to the first aspect of the present invention, the lens of the present invention is flexible, biocompatible and has a high refractive index and a particularly low risk of flare under physiological conditions. In addition, the ophthalmic lens can be stored dry and sterilized by steam sterilization. Further resulting features and advantages thereof can be inferred from the description of the first aspect of the present invention; advantageous embodiments of the first aspect of the present invention should be considered as advantageous embodiments of the second aspect of the present invention, and vice versa.

[0039] In an advantageous configuration of the invention, the ophthalmic lens in the non-hydrated state has a refractive index n D,20 ℃>1.51 and / or have a refractive index n in the hydrated state D,35℃>1.50 and / or a Shore A hardness of less than 80 (t=3s), in particular not more than 65 (t=3s), or a Shore A hardness of less than 50 (t=10min), and / or a glass transition temperature between 0°C and 15°C, in particular between 4°C and 9°C, and / or a water absorption capacity at 35°C of between 0.5% by weight and 3.5% by weight, in particular between 1.5% by weight and 2.5% by weight, and / or an Abbe number of at least 30, preferably at least 40. In this way, the ophthalmic lens of the invention combines one or more particularly advantageous properties. The ophthalmic lens preferably satisfies all of the abovementioned properties.

[0040] In another advantageous configuration of the invention, in an in vitro flare test by accelerated aging, in which the lens is first placed in a saline solution at 45° C.±1° C. for 24 h and then at 37° C.±1° C. for 2.5 h, the ophthalmic lens has a luminal density of not more than 10 MVs / mm 2 , preferably not more than 1MVs / mm 2 In other words, the ophthalmic lens advantageously has a particularly low microvesicle density, wherein the microvesicle density is determined by the test method cited. The saline solution is preferably a physiological saline solution (NaCl concentration 9 g / l, osmotic pressure 308 mOsm / l). In this way, problems otherwise caused by glare, such as glare symptoms when driving at night with oncoming lights or on sunny days, are completely or at least substantially completely avoided. More preferably, the lens is glare-free and in particular microvesicle-free, which can be achieved without difficulty using the ophthalmic composition according to the invention.

[0041] In another advantageous embodiment of the present invention, the ophthalmic lens has been steam sterilized. In this way, the lens of the present invention can be sterilized cheaply by established steam sterilization, which advantageously makes it possible to save chemical sterilization methods. Alternatively or additionally, the ophthalmic lens has been plasma treated. This can advantageously reduce surface viscosity. For example, plasma treatment can be carried out at 100W to 800W, preferably at about 400W for 1 to 10 minutes, especially about 5 minutes per IOL side, in a furnace with a HF plasma generator (e.g., 13.56MHz) and in a mixed atmosphere of oxygen and argon (e.g., 23sccm O2, 127sccm Ar, 400mTorr). Performance and duration can be changed as needed to achieve desired surface properties. In a plasma furnace, oxygen can be converted into ozone, which strengthens the treatment. Alternatively or additionally, the ophthalmic lens is stored in a storage box and / or in an implantation tool for implanting the lens in the eye in a preferably non-hydrated state. Alternatively or additionally, the lenses of the present invention can advantageously be used in dry and optionally fully pre-filled injection systems and do not have to be packaged or stored in liquids. This simplifies packaging and significantly extends shelf life and handling.

[0042] The polymer biomaterial produced by polymerization of the ophthalmic composition according to the first aspect of the invention constitutes another independent aspect of the invention. Preference is given here to using thermally induced free radical polymerization. Also conceivable is photochemically induced polymerization.

[0043] Another independent aspect of the invention is the plasma treatment of an ophthalmic lens. This can advantageously reduce the surface stickiness of the lens without the need for chemical coatings (e.g. heparin during the dipping process). The preferred procedure for the plasma treatment and the preferred parameters for the plasma treatment should be taken from the description of the second aspect of the invention above.

[0044] Additional features of the present invention will emerge from the claims and working examples. Without departing from the scope of the present invention, the features and combinations of features mentioned in the above description and the features and combinations of features mentioned and / or shown separately in the following working examples can be used not only in the corresponding specified combinations, but also in other combinations or alone. Therefore, the present invention should also be considered to include and disclose configurations that are not explicitly shown and explained in the working examples, but emerge from the explained configurations and can be created by a separate combination of features. The disclosure should also be considered to extend to combinations of embodiments and features, so these embodiments and combinations of features do not have all the features of the independent claims as described in the initial wording. Figure 1 A schematic diagram of an ophthalmic lens according to a working example of the present invention is shown. DETAILED DESCRIPTION

[0045] Figure 1 A schematic diagram of an ophthalmic lens 10 according to a working example of the present invention is shown. In this context, the ophthalmic lens 10 takes the form of a soft intraocular lens (IOL) and has a body 12. In this example, the body 12 has a first region 14a and a second region 14b, which are different in at least one parameter in the stiffness and hardness group. For this purpose, for example, the regions 14a, 14b can be produced by different embodiments of the ophthalmic composition discussed in detail below or undergo different post-processing. However, in the simplest form, the regions 14a, 14b are produced by the same ophthalmic composition and have no difference at the molecular level. The IOL 10 in the exemplary embodiment shown has an optical part 16 and a substantially optional haptic part 18, which is wing-shaped in the current case. However, the geometry of the haptic part 18 can be fundamentally changed and can take the form of, for example, a hook.

[0046] For the production of IOL 10, an ophthalmic composition according to the invention is used, which comprises comonomer groups A) to C), at least one comonomer group which is D), E) or a mixture thereof, and at least one crosslinker F). In this context, A) represents at least one (meth)acrylate having at least one aromatic group; B) represents at least one (meth)acrylate having an aliphatic or non-aromatic cyclic or non-aromatic heterocyclic group; C) represents at least one (meth)acrylate having at least one hydroxyl group; D) represents at least one (meth)acrylamide having an aromatic group and having an aliphatic or non-aromatic cyclic or non-aromatic heterocyclic group, and E) represents a mixture of at least one (meth)acrylamide having two aromatic groups and at least one (meth)acrylamide having two aliphatic and / or non-aromatic cyclic and / or non-aromatic heterocyclic groups.

[0047] Comonomer groups A) to D) / E) are discussed in detail in the following Table 2 together with their meanings, illustrative compounds and illustrative mass proportions based on the total weight of the composition. These mass proportions are related to the sum of all compounds of the corresponding categories A) to D) / E). For example, if category A) contains three different compounds and has a mass proportion of 50% by weight of the total weight of the composition, this mass proportion is composed of the sum of the respective mass proportions of the three compounds of category A).

[0048] Table 2: Comonomer groups A) to D) / E)

[0049]

[0050] Abbreviation meaning:

[0051] PEMA 2-phenylethyl methacrylate

[0052] PEA 2-phenylethyl acrylate

[0053] EGPEA Ethylene glycol phenyl ether acrylate

[0054] nBuA Butyl acrylate

[0055] iBuA Isobutyl acrylate

[0056] EHA 2-Ethylhexyl Acrylate

[0057] HEMA 2-Hydroxyethyl Methacrylate

[0058] HEA 2-Hydroxyethyl Acrylate

[0059] HBA 4-Hydroxybutyl Acrylate

[0060] BIPA N-Benzyl-N-isopropylacrylamide

[0061] BBA N-Benzyl-N-butylacrylamide

[0062] BIBA N-Benzyl-N-isobutylacrylamide

[0063] BIPEA N-Benzyl-N-isoamyl acrylamide

[0064] BMA N-Benzyl-N-methylacrylamide

[0065] BHEA N-Benzyl-N-2-hydroxyethyl acrylamide

[0066] As already mentioned, acrylates and the corresponding methacrylates, and also acrylamides and the corresponding methacrylamides can generally be exchanged or mixed with one another. Within the scope of the present disclosure, the alkyl substituents can generally have 1 to 12 carbon atoms. For example, compounds with the general formula III can generally be used as (meth)acrylamide:

[0067]

[0068] Among them, the alkyl group R 2 can be unbranched or branched and unsubstituted or substituted, in particular, by one, two or more hydroxy groups. 2 When substituted with one or more hydroxyl groups, preferably at least one hydroxyl group is located at a terminal end. The compound having formula III may preferably be N-benzyl-N-isopropylacrylamide (BIPA):

[0069]

[0070] The compound having formula III may be N-benzyl-N-isobutylacrylamide (BIBA):

[0071]

[0072] The compound having formula III may be N-benzyl-N-isoamyl acrylamide (BIPEA):

[0073]

[0074] The compound having formula III may be N-benzyl-N-2-hydroxyethylacrylamide (BHEA):

[0075]

[0076] In this case, the ethyl R 2 Substitution with terminal hydroxyl groups allows the compound BHEA to interact with the comonomer C) and also with water molecules. Generally, two or more, for example two, hydroxyl groups can also be provided as substituents, and the compounds of group D) can therefore conform to the general formula IV, wherein n and m are each selected in the range of 1 to 10, so that the sum of n+m is in the range of 2 to 11.

[0077]

[0078] Instead of the acrylamides shown, as already mentioned, it is fundamentally also possible to provide the corresponding methacrylamides and any mixtures thereof.

[0079] The advantageous interaction of the different comonomer groups A) to D) (or E)) is explained in detail in the following compositions V and VI with reference to the corresponding illustrative compounds.

[0080]

[0081] In composition V, for example, the compounds EGPEA (comonomer type A)), nBuA (comonomer type B)), 2-HEMA (comonomer type C)) and BBA (comonomer type D)) are used. It can be seen that in composition V, due to the selected structural similarity of the individual comonomer types A) to D) (or similarly E)), favorable intermolecular interactions are formed, because the mixed (meth)acrylamide D) acts as a kind of medium between groups A) and B). The aromatic groups of (meth)acrylamide D) also advantageously lead to an increase in the refractive index and form π-π interactions with the aromatic groups of the aromatic monomer A), which leads to a higher structural strength of the polymer. The alkyl groups of (meth)acrylamide D) increase the flexibility of the material. On the other hand, the comonomer type C) can form hydrogen bonds with water molecules enclosed in the polymer and the amide groups of (meth)acrylamide D) / E) through its terminal and sterically unhindered hydroxyl groups.

[0082] The same considerations apply to composition VI, in which, by way of example, the compounds PEA (comonomer type A)), iBuA (comonomer type B)), 2-HEMA (comonomer type C)) and BIPA (comonomer type D)) are used:

[0083]

[0084] According to the material design strategy described above, for example, several novel ophthalmic compositions were produced, polymerized and analyzed. The resulting polymer biomaterials showed promising properties in terms of material flexibility and tensile strength, as well as a high refractive index. In addition to the introduced monomers, (2-(5-chloro-2H-benzotriazole-2-yl)-6-(1,1-dimethylethyl)-4-vinylphenol) (UVAM), 2,2'-azobis(2-methylpropionitrile) (AIBN) as UV blockers for ophthalmic materials were used for thermal free radical initiation of the composition. Table 3 shows an illustrative ophthalmic composition (which is identified as "T-30C" and exists as an optically transparent biomaterial in a polymerized state) with the respective substance groups and the amounts used.

[0085] Table 3: Ophthalmic composition T-30C of the present invention

[0086]

[0087] However, the ophthalmic composition is not only suitable for producing transparent ophthalmic biomaterials. By adding an appropriate amount (usually <1.0% by weight) of yellow dye (group H), the ophthalmic composition can be easily adapted to produce yellow biomaterials. The amount of yellow dye used in the composition can be selected in a wide concentration range as needed. In this example, it is adjusted so that the composition has the same optical properties as the commercially available yellow biomaterial ZEISS CT Lucia (Acrylmex Y) in terms of the transmittance percentage at each wavelength within the range of 400nm to 500nm. This is achieved by adding a small amount (<1.0% by weight) of blue light absorbing yellow dye 4-(3-vinylphenylazo) diphenylamine (3VPADPA or VPAD) to the composition "T-30C" shown above. The correspondingly adjusted composition is referred to as "T-30Y" hereinafter.

[0088] The measured values ​​of three transparent (T-30C) and three yellow (T-30Y) biomaterial batches were used to determine the average values ​​of the respective physical properties. An overview of the average properties of the biomaterial of the preferred transparent type T-30C for ophthalmic compositions is given in Table 4, and an overview of the average properties of the biomaterial of the preferred yellow type T-30Y for ophthalmic compositions is given in Table 5.

[0089] Table 4: Properties of optically transparent material T-30C

[0090]

[0091]

[0092] Table 5: Properties of yellow material T-30Y

[0093]

[0094] In addition to the properties highlighted in Tables 4 and 5, the biomaterial also has excellent resistance to flare. The type and amount of crosslinker used for the elastomer affects the mechanical properties and can also be used to reduce flare. However, even in the case of compositions known from the prior art, variation in the amount of crosslinker alone is not sufficient to achieve all of the above requirements for the material, including reduction of flare. However, it was found that even with a constant amount of crosslinker (e.g., about 3% by weight), the addition of (meth)acrylamide comonomers D) / E) helps to steer the material properties in the desired direction.

[0095] Compared to low-glitter hydrophilic compositions known from the prior art that have to be stored in saline solution, the ophthalmic composition of the invention offers both the possibility of dry storage and the possibility of steam sterilization. Tailoring the water absorption of the polymeric biomaterial allows these conflicting requirements to be fulfilled with only one single material.

[0096] For experimental confirmation, flare studies were performed. During an accelerated aging process, five IOLs with a refractive power of 20.0D each were produced from the ophthalmic composition of the present invention and stored in a 0.9% sodium chloride solution at a temperature of 45°C for 24 hours, after which the lenses were incubated at 37°C for 2.5 hours and examined under a microscope with a digital camera and vacuolar detection software (Image J). It was found that two of the five IOLs remained completely free of microvacuoles (MVs) during the accelerated aging process. The other three IOLs had approximately 0.61 MV / mm 2 Very low microvesicle counts. This density not only corresponds to grade 0 on the Miyata scale, but is also well below the MV density achievable by the vast majority of currently commercially available IOL models in previous studies. The results of these previous studies are summarized in Table 6.

[0097] Table 6: Summary of flare study results for various IOL models

[0098]

[0099] Based on the test results, the material composition T-30C can be described not only as flare-free, but also as suitable for producing microvesicle-free lenses. It is important to note that the preferred ophthalmic compositions described in Table 3 can be adjusted for the compounds used in the various comonomer groups and for the concentration ranges of the various comonomer groups. Thus, many alternative formulations of the composition are possible within the scope of the present disclosure and which also possess the advantageous properties of the materials of the present invention.

[0100] It was found that the biomaterial produced from the composition of the present invention having a water absorption capacity of about 1.8% by weight resulted in sufficient distribution of water in the polymer so as not to show flare. At the same time, the water content was low enough not to cause problems due to swelling of the lens after implantation and therefore storage in an aqueous environment was not required. Furthermore, the water content and chemical composition enabled the lens to be steam sterilized.

[0101] It was determined that a lens with an optical zone of 5 mm (made of the material of the invention, for example of T-30C or T-30Y) can be injected with the aid of a Medicel Accuject syringe with a 1.8 cartridge without great expenditure of force. This meets the requirements for cataract surgery with microincisions. The IOL of the invention can also be injected without difficulty with an Accuject 2.2 cartridge. Injection tests were performed in vitro using an OVD (ophthalmic viscoelastic device) or a saline solution (BSS). The suitability is due to both the high refractive index of the material of the invention, which requires a lower lens thickness, and its flexibility, which is strongly influenced by the low glass transition temperature (Tg) of the material. The latter should be designed very carefully, since too high a Tg may make the polymer hard and too low a Tg may make the machining process more difficult. The composition of the invention T-30C / T-30Y has a Tg of about 6°C and is therefore at the lower end of the range of hydrophobic acrylate-based IOL materials (see Table 1). In addition to the production of lenses, mechanical tests were performed in order to demonstrate the machinability of biomaterials produced from the compositions of the invention.

[0102] Furthermore, the T-30C biomaterial was characterized by dynamic-mechanical thermal analysis (DMTA).In order to simulate the conditions during cryogenic turning and cryogenic milling of the material, the respective average rotation speeds of turning (7500 rpm = 125 Hz) and milling (14000 rpm = 233 Hz) were used as load frequencies. After experimental analysis, the shear storage modulus G' and the shear loss modulus G". were determined. Several different non-covalent bonds can be formed between the functional polymer groups of the compositions of the present invention (see compositions V and VI). These forces can be overcome when the biomaterial is heated (e.g. during steam sterilization) and are automatically regenerated when the material is cooled. DMTA testing shows that Tg only changes by about 2K when the load frequency is doubled, which allows good stability throughout the machining process. In addition, the biomaterial of the present invention shows a significantly smaller decrease in material stiffness with increasing temperature in the glassy state (shear storage modulus G'). Therefore, when the biomaterial of the present invention is machined (e.g. at -20°C), it therefore has a higher stiffness. At room temperature or higher, T-30C / Y is significantly softer, which, as already mentioned, leads to better implantability.

[0103] In addition to the advantages already emphasized, the biomaterial of the present invention was also tested for the standard requirements of ophthalmic lenses. These tests included photostability studies, including UV stability of the biomaterial and extraction of storage solutions. These tests were also successfully passed. In addition, several biocompatibility tests were also carried out, including cytotoxicity studies and risk analysis, which were also successfully completed. Material viscosity tests were also carried out, which is particularly important because the biomaterial of the present invention has a low Tg and high flexibility. For this purpose, the biomaterial disc of the present invention was cut into a smooth surface and pushed together with a certain force, and then the force required for separation was measured. In combination with other injection tests, it was found that chemical coatings (such as heparin in the immersion process) were not required for this biomaterial, and a simple plasma treatment specially developed for this purpose was sufficient to reduce surface viscosity. This plasma treatment process has also been shown to be stable over a long period of more than one year, thereby ensuring that the lens is safely unfolded after the storage period. The plasma treatment was performed in a furnace with an RF plasma generator (13.56 MHz) and in a mixed atmosphere of oxygen and argon (23 sccm O2, 127 sccm Ar, 400 mTorr) at 400 W for 5 minutes per IOL side. In the plasma furnace, oxygen is converted to ozone, which intensifies the treatment.

[0104] Finally, the suitability of the biomaterial of the present invention for steam sterilization was tested. For these tests, a disc with a thickness of 1.0 mm and a diameter of 6.0 mm was produced from the biomaterial and several hydrophobic acrylate materials known from the prior art by low temperature rotation. The disc was hydrated in an appropriate amount of aqueous solution in a container that can be autoclaved at room temperature for 48 hours. All containers were transferred to an autoclave and heated to 121 ° C at a standard rate (+6.6K / min, 15min in total). Before gradually cooling to room temperature (21 ° C), the container was kept at this temperature for 30 minutes. Cooling should preferably be carried out at a speed as slow as possible (e.g. -0.07K / min, 24h in total). The visible defects of these panels were then checked, particularly the microvesicles formed in the material. In the tests performed, the disc with the T-30C composition did not show permanent damage due to the microvesicles, and in this respect was able to exceed the hydrophobic reference sample. Therefore, the biomaterial and lens of the present invention are suitable for steam sterilization.

[0105] Table 7 below reports further working examples of ophthalmic compositions according to the invention. The biomaterials and the lenses produced therefrom have the same advantageous properties as the material T-30C / Y already discussed. The alternative compositions reported in Table 7 follow the described strategy and show by way of example and not exhaustive which variations are possible by comonomer exchange and / or by varying the proportions of the groups used in order to obtain comparable optical, physical and mechanical properties of the corresponding biomaterials.

[0106] Table 7: Working examples of ophthalmic compositions of the present invention

[0107]

[0108] Parameter values ​​specified in the literature for defining process and assay conditions for characterizing specific properties of the subject matter of the invention are also to be considered to be encompassed within the scope of the invention in the event of deviations due, for example, to measurement errors, systematic errors, weighing errors, DIN tolerances, etc.

[0109] List of Reference Numerals 10 Lens (IOL) 12 Main Body

[0110] 14a First Area

[0111] 14b Second Area

[0112] 16 Optical part 18 Tactile Part

Claims

1. An ophthalmic composition for producing an ophthalmic lens (10), comprising comonomer groups A) to C), at least one comonomer group D), E) or a mixture thereof, and at least one crosslinking agent F), wherein: -A) represents at least one (meth)acrylate having at least one aromatic group; -B) represents at least one (meth)acrylate having an aliphatic or non-aromatic cyclic or non-aromatic heterocyclic group; -C) represents at least one (meth)acrylate having at least one hydroxyl group; -D) represents at least one (meth)acrylamide having an aromatic group and having an aliphatic or non-aromatic cyclic or non-aromatic heterocyclic group; and -E) represents a mixture of at least one (meth)acrylamide having two aromatic groups and at least one (meth)acrylamide having two aliphatic and / or non-aromatic cyclic and / or non-aromatic heterocyclic groups; It is characterized in that Based on the total weight of the ophthalmic composition, - the proportion of comonomer group A) is between 30 and 60% by weight; - the proportion of comonomer group B) is between 10 and 45% by weight; - the proportion of comonomer group C) is between 5 and 30% by weight; - the proportion of the sum of comonomer groups D) and E) is between 1% by weight and 14% by weight; and The proportion of the crosslinker F) is not more than 5% by weight, in particular between 0.5% by weight and 5% by weight.

2. The ophthalmic composition according to claim 1, It is characterized in that -A) comprises or is 2-phenylethyl (meth)acrylate, ethylene glycol phenyl ether (meth)acrylate or a mixture thereof; and / or -B) contains or is butyl (meth)acrylate, isobutyl (meth)acrylate, 2-Ethylhexyl (meth)acrylate or mixtures thereof; and / or -C) comprises or is 2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate or a mixture thereof; and / or -D) comprises or is N-benzyl-N-isopropyl(meth)acrylamide, N-benzyl-N-butyl(meth)acrylamide, N-benzyl-N-isobutyl(meth)acrylamide, N-benzyl-N-isoamyl(meth)acrylamide, N-benzyl-N-amyl(meth)acrylamide, N-benzyl-N-methyl(meth)acrylamide or a mixture thereof; and / or -E) comprises or is N,N-dibenzyl(meth)acrylamide and N,N-diisopropyl(meth)acrylamide, N,N-dibenzyl(meth)acrylamide and N,N-dibutyl(meth)acrylamide, N,N-dibenzyl(meth)acrylamide and N,N-diisobutyl(meth)acrylamide, N,N-dibenzyl(meth)acrylamide, N,N-diisopentyl(meth)acrylamide and N,N-dipentyl(meth)acrylamide, N,N-dibenzyl(meth)acrylamide and N,N-dimethyl(meth)acrylamide or a mixture thereof; and / or -F) comprises a crosslinker having at least two (meth)acrylate groups, wherein the crosslinker comprises or is in particular butane-1,4-diol diacrylate and / or ethylene glycol dimethacrylate.

3. The ophthalmic composition according to claim 1 or 2, It is characterized in that It comprises at least one further component G), H), I) or a mixture thereof, wherein -G) represents at least one UV absorber which is preferably covalently bondable; -H) represents at least one preferably covalently bindable dye for modifying the light absorption properties; and -I) represents a polymerization initiator.

4. The ophthalmic composition according to claim 3, It is characterized in that Based on the total weight of the ophthalmic composition, - the proportion of component G) does not exceed 2% by weight; and / or - the proportion of component H) does not exceed 5% by weight; and / or - The proportion of component I) is not more than 3% by weight.

5. The ophthalmic composition according to claim 3 or 4, It is characterized in that The UV absorber G) contains or is 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-vinylphenol, and / or is characterized in that The dye H) comprises or is 4-(3-vinylphenylazo)diphenylamine.

6. An ophthalmic lens (10), in particular a soft intraocular lens, produced at least partially from an ophthalmic composition according to any one of claims 1 to 5.

7. The ophthalmic lens (10) according to claim 6, It is characterized in that The ophthalmic lens - has a refractive index n in the non-hydrated state D,20 ℃>1.51; and / or - has a refractive index n in the hydrated state D,35 ℃>1.50; and / or - having a Shore A hardness of less than 80 (t=3 s) and / or a Shore A hardness of less than 50 (t=10 min); and / or - has a glass transition temperature between 0°C and 15°C, in particular between 4°C and 9°C; and / or - has a water absorption capacity at 35° C. of between 0.5% by weight and 3.5% by weight, in particular between 1.5% by weight and 2.5% by weight; and / or - has an Abbe number of at least 30, preferably at least 40.

8. An ophthalmic lens (10) according to any one of claims 6 and 7, It is characterized in that In an in vitro flare test by accelerated aging, the lens (10) was first placed in a saline solution at 45°C ± 1°C for 24 h and then at 37°C ± At 1°C for 2.5h, the ophthalmic lens has a value not exceeding 10 MVs / mm 2 , preferably not more than 1MVs / mm 2 The microvacuole density.

9. The ophthalmic lens (10) according to any one of claims 6 to 8, It is characterized in that The ophthalmic lens has been steam sterilized and / or plasma treated and / or stored in a preferably non-hydrated state in a storage box and / or in an implantation tool for implanting the lens (10) in an eye.

Images