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HK1161071A1 - Ophthalmological composition and ophthalmological lens - Google Patents

Ophthalmological composition and ophthalmological lens Download PDF

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Publication number
HK1161071A1
HK1161071A1 HK12101531.0A HK12101531A HK1161071A1 HK 1161071 A1 HK1161071 A1 HK 1161071A1 HK 12101531 A HK12101531 A HK 12101531A HK 1161071 A1 HK1161071 A1 HK 1161071A1
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HK
Hong Kong
Prior art keywords
polymer
ophthalmologic
composition according
lens
hydrogen
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HK12101531.0A
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German (de)
French (fr)
Chinese (zh)
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HK1161071B (en
Inventor
Helmut Ritter
Daniel Schmitz
Original Assignee
Carl Zeiss Meditec Ag
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Publication of HK1161071A1 publication Critical patent/HK1161071A1/en
Publication of HK1161071B publication Critical patent/HK1161071B/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02—Prostheses implantable into the body
    • A61F2/14—Eye parts, e.g. lenses or corneal implants; Artificial eyes
    • A61F2/16—Intraocular lenses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A61L27/16—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02—Prostheses implantable into the body
    • A61F2/14—Eye parts, e.g. lenses or corneal implants; Artificial eyes
    • A61F2/16—Intraocular lenses
    • A61F2002/16965—Lens includes ultraviolet absorber
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2430/00—Materials or treatment for tissue regeneration
    • A61L2430/16—Materials or treatment for tissue regeneration for reconstruction of eye parts, e.g. intraocular lens, cornea
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Ophthalmology & Optometry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Cardiology (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Materials For Medical Uses (AREA)

Abstract

The invention relates to an ophthalmological composition comprising a polymer, which comprises at least one hydrophobic monomer of the general formula (I), wherein the polymer has a water absorption capacity of at most 10% and R1, R2, and R3 are hydrogen or alkyl groups independently of each other, Y is O or NR4 with R4 selected from among hydrogen or an alkyl group, X is O, S, SO, or SO2, S is a structural unit selected from among CR5 2 and/or (CR5 2CR5 2O)°CR5 2, wherein all R5s are hydrogen and/or alkyl groups independently of each other, n and o are an integer between 1 and 10 independently of each other, and m is an integer between 2 and 6. The invention further relates to an ophthalmological lens comprising such a polymer.

Description

Technical field
The present invention relates to an ophthalmological composition and an ophthalmological lens.
State of the art
Ophthalmological lenses such as intraocular lenses (IOL) are known to form one-piece or multi-piece. In single-piece IOLs, the optical and non-optical areas are made of one material. In multi-piece IOLs, the optical and non-optical areas can be made of different materials. The non-optical area is also called the haptic part and serves to attach the lens to a patient's eye.
In order to reduce the length of the incision required for the insertion of the ophthalmological lens into the eye, it is desirable to provide polymers or ophthalmological compositions which, for example, allow the incision to be shortened due to their flexibility and unfolding properties.
EP 0 231 572 A2 shows oxygen-permeable hard and medium-hard contact lenses composed of copolymers of unsaturated ethylene siloxanesters, unsaturated fluorine carbonesters and unsaturated sulfonomers.
GB 1 604 519 A is known for contact lenses made of polysiloxane polymers.
WO 2005/047349 A1 proposes a single-piece intraocular lens with an optical and a haptic part, where the optical and haptic areas are made from the same polymer, which is formed as a copolymer and has, in addition to the alcohol-alkylmethacrylate and alcohol-alkyl-lacrylate monomers, other acrylate and methacrylate monomers as subunits, of which no more than 55% may be contained in the copolymer by the total weight of the copolymer.
However, the disadvantage of the known polymers is that they either have a limited foldability or a comparatively low refractive index, which in both cases requires relatively large incisions when implanting ophthalmological lenses and implants made from these polymers.
Description of the invention
The present invention is intended to provide a polymer and an appropriate ophthalmological lens which have improved mechanical and optical properties and high biocompatibility.
This task is solved according to the invention by an ophthalmological composition as described in claim 1 and by an ophthalmological lens as described in claim 11.
A polymer of the invention for an ophthalmological composition, which has improved mechanical and optical properties while maintaining high biocompatibility, shall contain at least one hydrophobic monomer of general formula I Other the polymer has a water absorption capacity of not more than 10% and R1, R2 and R3 each independently represent hydrogen or alkyl residues, Y O or NR4 with R4 selected from hydrogen or alkyl residues, X O, S, SO or SO2 means X O, S means a structural unit selected from CR52 and/or (CR52CR52O) oCR52 where all R5s represent hydrogen and/or alkyl residues independently of each other, n and o independently of each other represent 1, 2, 3, 4, 5, 6, 7, 8, 9 and/or 10 and m 2, 3, 4, 5 or 6 are obtained. In principle, all enantiomers, diasteres and mitochondrial compounds of the general formula should be considered as polymers. In principle, this means that the monomer can be hydrophobic or monomeric in general and show at least one enantiomers of the general formula as improved by the present invention.
The polymer of the invention, by reason of its hydrophobicity, its low water absorption and its high refractive index, makes it possible to produce ophthalmological lenses, implants and the like, which have a higher refractive index than the state of the art, since this is the weighted sum by mass of the refractive indices of the anhydrous polymer and the water it absorbs, with water having only an index of refraction of 1,3.
Furthermore, the biological compatibility of the polymer of the invention in the eye is only improved by its low water absorption and thus reduced interaction with body tissues and by the preferential biological and chemical properties of the hydrophobic monomer. The polymer also offers an optimal machinability for the manufacture of an ophthalmic polymer, a polymer and a monomer, since the glass transition temperature of the monomer is aimed at at a minimum of one monomer and can be easily raised in a general area.
The invention is designed in a favourable way to ensure that the polymer has a water absorption capacity of not more than 5%, in particular not more than 2% and preferably not more than 1%. This allows, on the one hand, to increase the refractive index of the polymer further, which also further improves its biological compatibility due to the additional reduced interaction with biological tissue.
Further advantages are provided when a proportion of at least one hydrophobic monomer of general formula I by weight in relation to the total weight of the polymer is between 2% and 100%. The monomer ratios indicated in the context of the disclosure are in principle those of the total weight of the polymer and are to be selected in such a way that, taking into account any water content, the total is 100% by weight. In the case of additional ingredients such as radical initiators or the like, the weight ratios are to be selected in such a way that the total weight of the polymer, including the other ingredients, is 100% by weight.
A further advantageous design of the invention provides that R1 and/or R2 and/or R3 and/or R4 and/or R5 is hydrogen and/or an unbranched and/or branched alkyl residue with preferably 1, 2, 3, 4, 5, 6, 7, 8, 9 and/or 10 carbon atoms. This allows the mechanical and optical properties of the polymer to be adapted to the specific application in a particularly simple, variable and precise manner. As an alkyl residue, preferably methyl, ethyl, n-propyl, iso-propyl, n-butyl, butyl/terth-butyl residues may be provided. Alternatively, however, it may also be possible to use pentyl, decyl, heptyl, octyl, heptyl or n-oxyl resins, or polymers, with the corresponding mechanical properties and the corresponding optical properties of the polymer.
Further advantages are that R1 is hydrogen or CH3 when Y is O, or that R1 is hydrogen when Y is NH. This gives the polymer a particularly high malleability and correspondingly advantageous suitability for small-scale applications.
Another advantageous design of the invention provides that the monomer of the general formula I is tetrahydrofuran-2-yl (THFFMA) and/or tetrahydrofuran-2-yl (THFFA) and that the polymer has particularly advantageous properties, as it has a high chemical resistance to environmental influences and a particularly good biocompatibility in addition to a particularly high malleability, and that the polymer may be considered to contain only THFFMA and/or THFFFA as monomers, in addition to radical initiators, cross-linkers or the like, where appropriate.
In addition, a further advantageous design provides that the polymer contains at least one other hydrophobic monomer, which is not in accordance with the general formula I. This in particular allows for a particularly variable and precise adjustment of the glass transition temperature of the polymer. In principle, it can also be provided that at least one other hydrophobic monomer is present in enantiomeric pure form or as a racemic mixture. The other hydrophobic monomer may be, for example, only from the group of unbranched alkyl methyl acrylate.
A further advantageous design of the invention provides that at least one other hydrophobic monomer of the general formula II Other has a structural element selected from CR72 and/or (CR82CR82O) oCR82. All R7s are independently hydrogen, alkyl residues and/or cycloalkyl residues. Furthermore, all R8s are independently hydrogen and/or alkyl residues and p and o are independently an integer between 1 and 10. In the case of the other hydrophobic monomer of general formula II, all diastereomers, enantiomers or racemic mixtures are also generally considered to be mitochondria. Using a monomer of general formula II is an additional way to adjust the optimal chemical, mechanical and optical properties of the polymer to the respective application.It has been shown to be advantageous to select the residues R6, R7 and R8 independently from unbranched and/or branched and/or cyclic alkyl groups with preferably 1, 2, 3, 4, 5, 6, 7, 8, 9 and/or 10 carbon atoms. The residues R6, R7 and R8 may therefore be, for example, a methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl and/or cyclohexyl group. Alternatively or additionally, however, their pentyl, hexyl, heptyl, octyl, nonyl or decyl groups with corresponding total polymers may be provided to provide a polymer with the mechanical and optical properties of a monomeric hydrogen, CH3, or R6 respectively.The methacrylate base is obtained.
Further advantages are that the weight ratio of at least one other hydrophobic monomer to the total weight of the polymer is between 1 and 55%, which allows the weight ratio of at least one other hydrophobic monomer to be optimally selected depending on the type and quantity of at least one hydrophobic monomer of the general formula I to achieve the desired polymer properties.
The polymer incorporates a UV absorber, which allows optimal protection of the polymer and, when the polymer is used for ophthalmological applications, of the patient's eye from short and long-wave UV light. UV absorbers are particularly suitable for compounds that predominantly and particularly preferably absorb radiation in the wavelength range from about 200 nm to about 420 nm.
In the case of the UV absorber, the general formula III has been shown to be advantageous. Other has, where R1 means acrylic and/or methacrylic residues independently, R2 means alkyl and/or aryl residues independently branched and/or unbranched with up to 30 atoms selected from C, H, Si, O, N, P, S, F, Cl, Bruten, R3, R4 and R5 independently of each other, hydrogen and/or branched and/or unbranched alkyl and/or aryl residues with up to 30 atoms selected from C, H, Si, O, N, P, S, F, Cl, Bruten, X and Y independently of each other, O, S, NH, or NR6, where R6 means a branched and/or unbranched alkyl and/or aryl residue with up to 30 atoms selected from C,H, Si, O, N, P, S, F, Cl, Br is, and n=0 to 2 and m=0 or 1, where n+m is always greater than 1. Non-limiting examples of advantageous structures (with R = hydrogen and/or CH3; all stereoisomers or racemic mixtures are included) are: Other UV absorbers, whose basic structure is based on structures 2, 3 and 5, have the additional advantage that, due to the presence of several polymerizable end-groups, they not only allow a quantitative incorporation into the polymer but also have interconnecting properties, which allows the addition of an additional interconnector to be avoided.
Other advantages are that the polymer has at least one violet absorber. Preferably, the violet absorber (so-called yellow dye) absorbs predominantly, or preferably, quantitatively, violet light in the wavelength range between about 400 nm and about 430 nm. However, in principle, two or more different violet absorbers with different absorption characteristics may also be provided. Particularly preferable is that at least one violet absorber has an edge filter, i.e. that this light absorbs quantitatively the wavelengths from about 400 nm to about 430 nm and subsequently a strong increase in transmission along the wavelengths of the larger wavelengths. For example, a violet absorber can be designed to transmit a maximum transmission degree between about 400 nm and about 450 nm, in the wavelength range of about 430 nm and about 0,05 nm.
Such an absorption profile is further advantageous in the design of the invention by a violet absorber with general formula IV. where R1 means independently branched and/or unbranched alkyl and/or aryl residues with up to 30 atoms selected from C, H, Si, O, N, P, S, F, Cl, Bruten, R3 hydrogen, electron acceptor substituent or branched and/or unbranched alkyl and/or aryl residue with up to 30 atoms selected from C, H, Si, O, N, P, S, S, F, Cl, Br, and X means O, S, NH or NR4, where R4 means a branched and/or unbranched alkyl and/or aryl residue with up to 30 atoms selected from C, H, Si, O, N, P, F, Cl, Br, R3 hydrogen, electron acceptor substituent or branched and/or unbranched alkyl and/or aryl residue with up to 30 atoms selected from C, H, Si, O, N, S, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F
Alternatively or additionally, the desired violet absorption can be ensured by the violet absorber using the general formula V. Other has, where R1 means acrylic and/or methacrylic residues independently of each other, R2 and R3 means independently branched and/or unbranched alkyl and/or aryl residues up to 30 atoms selected from C, H, Si, O, N, P, S, F, Cl, Br, R4 means hydrogen, an electron acceptor substituent or a branched and/or unbranched alkyl and/or aryl residue up to 30 atoms selected from C, H, Si, O, N, P, S, F, Cl, Br, and X means O, S, NH or NR5, where R5 means a branched and/or unbranched alkyl and/or aryl residues up to 30 atoms selected from Si, C, P, O, P, N, F, Cl, P, S, F, C, P, N, F, C, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F, F,
Further advantages arise when the polymer includes at least one interconnector, which allows the polymer strands of the polymer to be linked into a three-dimensional network, thereby modifying the polymer's property profile specifically and adjusting it according to the intended use.
By at least one network is a UV absorber and/or a violet absorber, the number and quantity of chemicals used to produce the polymer can be reduced to a beneficial extent, which can result in corresponding cost reductions.
In further design, it has been shown to be advantageous if the polymer has a refractive index of at least 1.3 and preferably at least 1.5.
The polymer has a glass transition temperature in the range of - 10°C to 30°C, in particular between 0°C and 30°C and/or between 5°C and 20°C, which allows the deformability of the polymer to be optimally adapted, especially with regard to human or animal body temperature.
Another aspect of the invention concerns an ophthalmological composition which, by incorporating a polymer or an advantageous design, has improved mechanical and optical properties according to the invention, while at the same time being highly biocompatible. The resulting characteristics and advantages are derived from the foregoing descriptions and apply accordingly to the ophthalmological composition. In particular, an ophthalmological composition is to be understood as a chemical composition or preparation for ophthalmology.
The advantageous design of the invention provides that the ophthalmological composition consists exclusively of the polymer according to one of the preceding embodiments. By eliminating additional ingredients, the ophthalmological composition can be produced in a particularly simple and cost-effective manner, whilst retaining the advantageous properties of the polymer in full.
Another aspect of the invention concerns an ophthalmological lens which, according to the invention, has improved mechanical and optical properties with high biocompatibility by incorporating a polymer in one of the previous embodiments and/or an ophthalmological composition in one of the previous embodiments. The lens according to the invention has a high refractive index and a particularly good foldability in high biocompatibility and can be either partial or multi-partial in principle. It can be assumed that the lens consists exclusively of the polymer or ophthalmological composition. Further characteristics and advantages are to be derived from the above descriptions and applied to the ophthalmological lens.
In the present invention, it has been shown to be advantageous to design the ophthalmological lens as an intraocular or contact lens.
A further advantageous design of the invention provides that the ophthalmological lens shall have a water content of not more than 10%, preferably not more than 5%, preferably not more than 2% and particularly preferably not more than 1%.
Another aspect of the invention concerns a medical implant, in particular an eye implant, which has improved mechanical and optical properties according to the invention, while maintaining high biocompatibility, by incorporating a polymer according to one of the previous embodiments and/or an ophthalmological composition according to one of the previous embodiments. The implant according to the invention, which may be, for example, a lens and/or a ring and/or a support and/or a support and/or a prosthesis, thus has a particularly good foldability with high biocompatibility and may be fundamentally proportional or more. The invention is therefore intended to exclude the possibility that the polymer composition may be used for the initial and/or the subsequent development of the implant and its prosthesis.
Another aspect of the invention concerns the use of a polymer in one of the preceding embodiments and/or an ophthalmological composition in one of the preceding embodiments for the manufacture of an ophthalmological lens, in particular a contact or intraocular lens, and/or a medical implant.
Examples of embodiments of the invention Example of implementation 1
5,4 g tetrahydroflufurylmethacrylate (THFFA) is stirred with 1,6 g tetrahydroflufurylmethacrylate (THFFMA), 70 mg ethylene glycoldimethylated (EGDMA) as a solvent, 105 mg cumarine-5,7-di ((propoxymethylated) as a UV absorber and 11,2 mg 4-nitrophenylimino-di ((2'-ethylmethacrylate) as a violet absorber under high pressure stirring at 35°C. The reaction mixture is stirred with nitrogen gas and for about 10 minutes. The polymerization is carried out by adding 4,9 mg ethylene glycoldimethylated (EGDMA) as a solvent, and the mixture is sprayed in a polymerised polymerised solvent. The polymerization is carried out in a vacuum-free manner over a period of 48 hours (usually at a temperature of about 125°C and approximately 1,1°C) and is suitable for the treatment of polymers and polymers with a high degree of polymerisation.
Example of implementation 2
The polymer in the second embodiment was also produced by the process described in the first embodiment. The educts used here and the process parameters are given in Table 1. Unlike in the first embodiment, no additional connector was used, as both the UV absorber (cumarin-5,7-di-propoxymethacrylate) and the violet absorber (4-nitrophenylimino-bis-(2'-ethylmethacrylate)) have two polymerizable end groups and thus have connecting properties. The polymer in the second embodiment also includes, apart from the radical starter (V65) and the UV and violet-A hydrophobic ammonia exclusively of the general formula I of Monmel. Other
Gesamteinwaage [g] 7, 0
Tetrahydrofufurylmethacrylat
Einwaage [g] 1,376
Gew.% (soll) 20,00
Gew.% (ist) 19, 65
Tetrahydrofufurylacrylat
Einwaage [g] 5,503
Gew.% (soll) 80, 00
Gew.% (ist) 78, 62
Radikalstarter V65
Einwaage [g] 0, 0049
Gew.% 0,07
Cumarin-5,7-di(propoxymethacrylat)
Einwaage [g] 0,105
Gew.% 1,5
4-Nitrophenylimino-bis-(2'-ethylmethacrylat)
Einwaage [g] 0, 0112
Gew.% 0,16
Trockenschrank 70°C [h] 24
48
Glasübergangstemperatur Tg [°C] 5,1
Brechungsindex 1,5
The parametric values specified in the documents defining process and measurement conditions for characterizing specific properties of the subject matter of the invention are also to be considered included in the scope of the invention in the case of deviations, for example due to measurement errors, system errors, weighing errors, DIN tolerances and the like.

Claims (14)

  1. Ophthalmologic composition including a polymer comprising at least one hydrophobic monomer of the general formula I wherein the polymer has a water absorption capacity of at most 10%, and:
    R1, R2 and R3 each independently of each other denote hydrogen or alkyl radicals;
    Y denotes O or NR4 with R4 selected from hydrogen or alkyl radical;
    X denotes O, S, SO or SO2;
    S denotes a structural unit selected from CR5 2 and/or (CR5 2CR5 2O)oCR5 2, wherein all R5 each independently of each other denote hydrogen and/or alkyl radicals;
    n and o independently of each other denote an integer between 1 and 10; and
    m denotes an integer between 2 and 6.
  2. Ophthalmologic composition according to claim 1, characterized in that the polymer has a water absorption capacity of at most 5%, in particular of at most 2% and preferably of at most 1%.
  3. Ophthalmologic composition according to claim 1 or 2, characterized in that a weight portion of the at least one hydrophobic monomer of the general formula I related to the overall weight of the polymer is between 2 and 100 percent by weight.
  4. Ophthalmologic composition according to any one of claims 1 to 3, characterized in that R1 is hydrogen or CH3- if Y is O, or that R1 is hydrogen if Y is NH.
  5. Ophthalmologic composition according to any one of claims 1 to 4, characterized in that the monomer of the general formula I is tetrahydrofufuryl methacrylate (THFFMA) and/or tetrahydrofufuryl acrylate (THFFA).
  6. Ophthalmologic composition according to any one of claims 1 to 5, characterized in that the polymer includes at least one further hydrophobic monomer.
  7. Ophthalmologic composition according to any one of claims 1 to 6, characterized in that the polymer includes an UV absorber and/or at least a violet absorber.
  8. Ophthalmologic composition according to any one of claims 1 to 7, characterized in that the polymer includes at least a cross-linker, wherein the cross-linker is in particular an UV absorber and/or a violet absorber.
  9. Ophthalmologic composition according to any one of claims 1 to 8, characterized in that the polymer has a refractive index of at least 1.3 and preferably of at least 1.5.
  10. Ophthalmologic composition according to any one of claims 1 to 9, characterized in that the polymer has a glass transition temperature in the range between -10°C and 30 °C, in particular between 0 °C and 30 °C and/or between 5°C and 20°C.
  11. Ophthalmologic lens including an ophthalmologic composition according to any one of claims 1 to 10.
  12. Ophthalmologic lens according to claim 11, characterized in that it is formed as an intraocular lens or as a contact lens.
  13. Ophthalmologic lens according to claim 11 or 12, characterized in that it has a water content of at most 10%, preferably of at most 5 %, preferred of at most 2% and particularly preferred of at most 1%.
  14. Use of an ophthalmologic composition according to any one of claims 1 to 10 for manufacturing an ophthalmologic lens, in particular a contact or intraocular lens, and/or a medical implant.
HK12101531.0A 2009-03-12 2010-03-11 Ophthalmological composition and ophthalmological lens HK1161071B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102009012959.6 2009-03-12
DE102009012959A DE102009012959A1 (en) 2009-03-12 2009-03-12 Polymer for an ophthalmic composition and ophthalmic lens with such a polymer
PCT/EP2010/053139 WO2010103089A1 (en) 2009-03-12 2010-03-11 Ophthalmological composition and ophthalmological lens

Publications (2)

Publication Number Publication Date
HK1161071A1 true HK1161071A1 (en) 2012-08-24
HK1161071B HK1161071B (en) 2014-01-10

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EP2405860A1 (en) 2012-01-18
WO2010103089A1 (en) 2010-09-16
DE102009012959A1 (en) 2010-09-16

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