DE102006004111A1 - Contact lens material for single-day use and one-month hydrogel contact lenses based on alkyl-ammonium-halogenide derivate - Google Patents
Contact lens material for single-day use and one-month hydrogel contact lenses based on alkyl-ammonium-halogenide derivate Download PDFInfo
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- DE102006004111A1 DE102006004111A1 DE102006004111A DE102006004111A DE102006004111A1 DE 102006004111 A1 DE102006004111 A1 DE 102006004111A1 DE 102006004111 A DE102006004111 A DE 102006004111A DE 102006004111 A DE102006004111 A DE 102006004111A DE 102006004111 A1 DE102006004111 A1 DE 102006004111A1
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- Germany
- Prior art keywords
- contact lens
- lens material
- material according
- chloride
- ammonium
- Prior art date
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- 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
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
- C08F220/365—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate containing further carboxylic moieties
-
- 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
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
Abstract
Description
Die Erfindung betrifft ein Kontaktlinsenmaterial nach dem Oberbegriff des Hauptanspruches. Kontaktlinsenmaterialien sollen bevorzugt einen hohen Wassergehalt, gute Sauerstoffdurchlässigkeit, ein gutes Wasserrückhalteverhalten, eine gut gleitende Oberfläche, gute optische Eigenschaften, gute Verarbeitungseigenschaften und gute mechanische Eigenschaften, wie Reißfestigkeit, besitzen. Dabei sollen die Kontaktlinsenmaterialien auch annähernd die Eigenschaften der Cornea des menschlichen Auges aufweisen.The The invention relates to a contact lens material according to the preamble of the main claim. Contact lens materials are preferably a high water content, good oxygen permeability, good water retention behavior, a good sliding surface, good optical properties, good processing properties and have good mechanical properties, such as tear resistance. there The contact lens materials should also approximate the properties of Cornea of the human eye.
Der Wassergehalt der Cornea liegt üblicherweise bei ca. 65 bis 75 Gew.-%, der auf ein außerordentlich hohes Wasserrückhaltevermögen der Cornea selbst zurückzuführen ist. Durch diese Wasserretention wird eine zu starke Abnahme der Oberflächenfeuchtigkeit in trockener Luft, wie etwa in kalter (Polar-)Luft, sowie auch in klimatisierten Räumen mit hoher Wasserverdunstung, wie etwa in Flugzeugen, vermieden. Dabei verhindert das hohe Wasserrückhaltevermögen gleichzeitig, dass die Konzentration der in der Tränenflüssigkeit gelösten Stoffe bei ansonsten hoher Verdunstung zu stark ansteigt und diese dann auskristallisieren.Of the Water content of the cornea is usually at about 65 to 75 wt .-%, which is based on an extraordinarily high water retention capacity of Cornea itself is due. Due to this water retention, the surface moisture will decrease too much in dry air, such as in cold (polar) air, as well as in air-conditioned rooms with high water evaporation, such as in aircraft avoided. At the same time, the high water retention capacity prevents the Concentration of the substances dissolved in the tear fluid otherwise increases too high evaporation and then this crystallize.
In diesem Zusammenhang ist es bekannt, dass für das Wasserrückhaltevermögen der natürlichen Cornea Sulfoverbindungen, insbesondere Keratansulfate und Chondroitinsulfate, eine Rolle spielen.In In this context, it is known that the water retention capacity of natural cornea Sulfo compounds, in particular keratan sulfates and chondroitin sulfates, play a role.
Neben der besonderen Eigenschaft des Wasserrückhaltevermögens muss die Cornea auch ein hohe Sauerstoffdurchlässigkeit aufweisen, da die Cornea auf ihrer Innenseite eine endotheliale Zellschicht besitzt, deren Sauerstoffversorgung nicht durch Gefäße, sondern aus der Umgebungsluft durch die Cornea hindurch erfolgt. Ein immerwährendes Aussetzen der Cornea mit der Umgebungsluft würde jedoch trotz ihres hohen Wasserrückhaltevermögens zu ihrem Austrocknen führen. Um dies zu vermeiden, wird die Cornea daher durch Lidschlag permanent mit einer als Tränen bezeichneten Flüssigkeit benetzt, die Proteine, Lipoproteine, Lipide und Mucine gelöst enthält.Next The special feature of the water retention ability must also be the cornea high oxygen permeability exhibit, since the Cornea on its inside an endothelial Cell layer possesses, whose oxygen supply not by vessels, but takes place from the ambient air through the cornea. An everlasting However, exposure of the cornea to the ambient air would increase, in spite of its high water retention capacity lead to their drying out. To avoid this, the cornea becomes permanent by blinking with one as tears designated liquid which contains proteins, lipoproteins, lipids and mucins dissolved.
Durch die dauernde Neuzufuhr dieser Flüssigkeit und deren Verdunstung auf der Augenoberfläche müssten sich diese in der Tränenflüssigkeit gelösten Stoffe auf der Cornea ablagern und diese eintrüben. Damit dies nicht geschieht, hat die Natur Schutzmechanismen entwickelt, die jedoch noch nicht gänzlich aufgeklärt sind.By the continuous re-feeding of this liquid and their evaporation on the ocular surface would have these in the tear fluid dissolved Deposit substances on the cornea and cloud them. So that does not happen, Nature has developed protective mechanisms, but they have not completely enlightened are.
Es ist jedoch bekannt, dass in der Natur die Ablagerung der oben genannten Substanzen auf der Corneaoberfläche auch durch eine Betainstruktur innerhalb des Kollagens vermieden wird. Dabei enthält das Kollagen der Cornea als Aminosäuren Glycin, Prolin, Glutamin, Alanin, Arginin, Asparagin, Lysin, Leucin, Serin, Isoleucin sowie andere.It However, it is known that in nature the deposition of the above Substances on the corneal surface also avoided by a betaine structure within the collagen becomes. It contains the collagen of the cornea as amino acids glycine, proline, glutamine, Alanine, arginine, asparagine, lysine, leucine, serine, isoleucine as well other.
Bei der Anfertigung von Kontaktlinsen besteht deshalb die Notwendigkeit, darauf zu achten, dass die physiologischen Aufgaben der Cornea durch die auf die Cornea aufgesetzte Kontaktlinse und damit durch Abdecken eines Teilbereichs der Cornea im Wesentlichen nicht beeinträchtigt werden. Dieses kann dadurch erreicht werden, dass die Kontaktlinse annähernd die Eigenschaften der Cornea des Auges besitzt, wobei auch darauf geachtet werden muss, dass der Brechungsindex der Kontaktlinse dem Brechungsindex der Cornea von 1,37 angenähert sein sollte.at the manufacture of contact lenses therefore requires to pay attention that the physiological tasks of the cornea through the placed on the cornea contact lens and thus by covering a portion of the cornea are not substantially affected. This can be achieved in that the contact lens approximately the Features of the cornea of the eye possesses, while also paying attention must be that the refractive index of the contact lens the refractive index approximated to the cornea of 1.37 should be.
Aus
der
Aufgabe der Erfindung ist es daher, ein Material für Kontaktlinsen, insbesondere für Ein-Tages-Kontaktlinsen und bis zu einen Monat getragene Hydrogel-Kontaktlinsen, anzugeben, das eine vorteilhafte Kombination der genannten Eigenschaften aufweist. Eine Herstellung im Formgussverfahren wird in einer bevorzugten Ausführungsform angestrebt.task The invention is therefore a material for contact lenses, in particular for one-day contact lenses and hydrogel contact lenses worn for up to one month, which has an advantageous combination of the properties mentioned. A production in the casting method is in a preferred embodiment sought.
Zur Lösung der Aufgabe wird erfindungsgemäß ein Material mit den Merkmalen des Anspruches 1 vorgeschlagen, dass zudem in Kontaktlinsenform mit einem Pflegemittel gereinigt werden kann, dass dasselbe Material als wasserlösliches Lösungspolymerisat enthält.to solution the object is a material according to the invention proposed with the features of claim 1 that also in Contact lens mold can be cleaned with a care product, that contains the same material as a water-soluble solution polymer.
Im Wesentlichen besteht die Erfindung darin, dass in das Basismaterial eines Kontaktlinsenmaterials wenigstens ein Alkylammoniumhalogenid-Derivat als Comonomer einpolymerisiert ist.in the Essentially, the invention consists in that in the base material a contact lens material at least one alkylammonium halide derivative copolymerized as a comonomer.
Dabei
kann es sich bei dem Alkylammoniumhalogenid-Derivat um ein Alkylammoniumesterhalogenid der
allgemeinen Formel oder ein Alkylammoniumamidhalogenid
der allgemeinen Formel handeln, wobei
R1: verzweigter
oder unverzweigter, bevorzugt C2, Alken-Rest,
R2: verzweigter
oder unverzweigter, bevorzugt C2-C3, Alkylen-Rest,
R3: verzweigter
oder unverzweigter, bevorzugt C1-C12, Alkyl-Rest,
m: verzweigter
oder unverzweigter, bevorzugt C1-C20, Alkylen-Rest,
R4: verzweigter
oder unverzweigter, bevorzugt C1-C20, Alkoxycarbo- oder Phenyl-
oder Alkoxysilyl-Rest
R5: Halogen
bedeutet.In this case, the alkylammonium halide derivative may be an alkylammonium ester halide of the general formula or an alkylammonium amide halide of the general formula act, being
R1: branched or unbranched, preferably C2, alkene radical,
R 2: branched or unbranched, preferably C 2 -C 3, alkylene radical,
R 3: branched or unbranched, preferably C 1 -C 12, alkyl radical,
m: branched or unbranched, preferably C 1 -C 20, alkylene radical,
R 4: branched or unbranched, preferably C 1 -C 20, alkoxycarbo or phenyl or alkoxysilyl radical
R5: halogen
means.
Bevorzugt ist das Comonomer ein Alkyammoniumchlorid-Derivat, wobei aber auch andere Halogenide, beispielsweise Bromide oder Jodide, denkbar sind. Das Alkylammoniumchlorid-Derivat ist bevorzugt N-Carbomethoxymethyl-N-methacryloylamidopropyl-N,N-dimethylammoniumchlorid (AM1M) oder N-Carboxyethoxymethyl-N-methacryloylamidopropyl-N,N-dimethylammoniumchlorid (AM1E) oder ein anderes der im Anschluss an die Beschreibung in Tabelle 1 aufgeführten Alkylammoniumhalogenid-Derivate.Prefers the comonomer is an alkylammonium chloride derivative, but also other halides, for example bromides or iodides, are conceivable. The alkylammonium chloride derivative is preferably N-carbomethoxymethyl-N-methacryloylamidopropyl-N, N-dimethylammonium chloride (AM1M) or N-carboxyethoxymethyl-N-methacryloylamidopropyl-N, N-dimethylammonium chloride (AM1E) or another following the description in Table 1 listed Alkylammonium halide derivatives.
Das Basismaterial besteht bevorzugt aus Hydroxyethylmethacrylat (HEMA) und/oder Hydroxypropylmethacrylat (HPMA) und/oder einem Sulfobetain, besonders bevorzugt N,N-Dimethyl-N-(2-methacryloyloxyethyl-N-(3-sulfopropyl)ammonium-betain (SPE), oder einem Gemisch davon.The Base material preferably consists of hydroxyethyl methacrylate (HEMA) and / or hydroxypropyl methacrylate (HPMA) and / or a sulfobetaine, particularly preferably N, N-dimethyl-N- (2-methacryloyloxyethyl-N- (3-sulfopropyl) ammonium betaine (SPE), or a mixture thereof.
Bevorzugt wird das erfindungsgemäße Kontaktlinsenmaterial durch Hitzepolymerisation oder durch Polymerisation mit UV-Licht hergestellt. Die aus diesem Material gefertigten Hydrogel-Kontaktlinsen sind weiterhin bevorzugt durch ein spanabhebendes Verfahren aus einem Stangenmaterial oder direkt durch Formgießen hergestellt.Prefers becomes the contact lens material according to the invention by heat polymerization or by polymerization with UV light produced. The hydrogel contact lenses made of this material are further preferred by a machining method a bar stock or directly made by molding.
Schließlich ist ein Pflegemittel für die erfindungsgemäße Hydrogel-Kontaktlinse vorgesehen, dass die erfindungsgemäßen unter Bedingungen der Lösungspolymerisation hergestellten Polymere als Lösungspolymerisat enthält.Finally is a care product for the hydrogel contact lens according to the invention provided that the inventive under conditions of solution polymerization produced polymers as a solution polymer contains.
Die
Erfindung wird im Folgenden anhand von Beispielen näher erläutert:
Ausgehend
von einem zur Herstellung von Kontaktlinsen üblicherweise verwendeten Basismaterial,
beispielsweise Hydroxyethylmethacrylat (HEMA) oder N,N-Dimethyl-N-(2-methacryloyloxyethyl-N-(3-sulfopropyl)ammoniumbetain
(SPE), wurde ein Comonomer gesucht, das dem polymerisierten Kontaktlinsenmaterial
die zur Weiterverarbeitung zur Kontaktlinse notwendigen eingangs
genannten Eigenschaften verleiht.The invention is explained in more detail below with reference to examples:
Starting from a base material commonly used for producing contact lenses, for example, hydroxyethyl methacrylate (HEMA) or N, N-dimethyl-N- (2-methacryloyloxyethyl-N- (3-sulfopropyl) ammonium betaine (SPE), a comonomer was sought which polymerized Contact lens material gives the necessary for further processing to the contact lens properties mentioned above.
Überraschenderweise wurde gefunden, dass sich Cholinchlorid als Ausgangsmaterial zur Herstellung von Hydrogelmaterial eignet. Cholinchlorid ist eine hygroskopische Substanz, die in kristalliner Form als weißes Pulver vorliegt und in Wasser und in polaren organischen Lösungsmitteln, wie z.B. Methanol, Ethanol, Dimethylformamid, löslich ist. Cholinchlorid ist in der Physiologie auch als Vitamin B4 und wird vor allem als Futtermittelzusatz, beispielsweise zur Schweinemast, eingesetzt. Für den Menschen ist eine Tageseinnahmeempfehlung nicht festgelegt, da es zumeist ausreichend mit der Nahrung zugeführt wird.Surprisingly was found to be choline chloride as the starting material for Production of hydrogel material is suitable. Choline chloride is one hygroscopic substance in crystalline form as a white powder present in water and in polar organic solvents, such as. Methanol, ethanol, dimethylformamide, is soluble. Choline chloride is in physiology also as vitamin B4 and is used primarily as a feed additive, For example, for pig fattening, used. For humans is a daily intake recommendation not fixed, since it is usually supplied with sufficient food.
Aufgrund seiner physiologischen Unbedenklichkeit, seiner guten Wasserlöslichkeit und seiner hygroskopischen Eigenschaft besitzt Cholinchlorid gegenüber den bekannten toxischen, flüssigen Monomeren, wie beispielsweise N-Vinyl-2-pyrrolidinon oder N,N-Dimethylacrylamid gute Voraussetzungen zum Einsatz in Kontaktlinsen.Due to its physiological harmlessness, its good water solubility and its hygroscopic property, choline chloride has over the known toxic, liquid monomers, such as For example, N-vinyl-2-pyrrolidinone or N, N-dimethylacrylamide good conditions for use in contact lenses.
Problematisch erschien zunächst allerdings, dass zur Herstellung eines als Kontaktlinsenmaterials geeigneten Polymers eine vinyloge Doppelbindung in das Cholinmolekül eingeführt werden muss ohne dessen Struktur im Wesentlichen zu verändern. Insbesondere muss die Ammoniumstruktur erhalten bleiben, um die Wechselwirkung zwischen dem Polymer und Wasser zu erhalten.Problematic first appeared however, that for making a contact lens material suitable polymer a vinylogous double bond are introduced into the choline molecule without essentially changing its structure. In particular, the Ammonium structure are preserved to the interaction between to obtain the polymer and water.
Prinzipiell
wurde hierzu speziell auf die in der
Es wurde dabei gefunden, dass die so hergestellten Alkylammoniumchloride sehr gut in HEMA löslich sind und nach den bekannten Methoden zu Formguss-Kontaktlinsen und Stangen verarbeitet werden können. Vorteilhaft erwies sich bei dieser Methode auch, dass die Ausgangsprodukte relativ billig sind und die Ausbeute des Reaktionsprodukts sehr gut ist.It was found that the alkyl ammonium chlorides thus prepared are very soluble in HEMA and according to the known methods of molded contact lenses and rods can be processed. Advantageous In this method also proved that the starting materials relative are cheap and the yield of the reaction product is very good.
Zur Polymerisierung wurden die bereits in Tabelle 1 erwähnten, beispielhaft aufgeführten Alkylammoniumchloride verwendet, die entsprechend der nachstehend für das Alkylammoniumchlorid AM1M beispielhaft aufgeführten Anleitung aus den in der Tabelle mit A und B bezeichneten Ausgangsstoffen synthetisiert wurden.to Polymerization were the already mentioned in Table 1, by way of example listed Alkyl ammonium chlorides used according to the below for the Alkylammonium chloride AM1M example listed instructions from the in synthesized in the table labeled A and B starting materials were.
Das Alkylammoniumchlorid AM1M wird aus dem Ausgangsstoff A: Methacrylsäure-(3-dimethylaminopropylamid) und dem Ausgangssstoff B: Chloressigsäuremethylester dargestellt. Hierzu werden 17,03 g (entspricht 0,1 Mol) Methacrylsäure-(3-dimethylaminopropylamid) [MW 170,25] in 40 ml Aceton gelöst und mit einer Lösung aus 11,94 g (entspricht 0,11 Mol) Chloressigsäuremethylester [MW 108,52] in 20 ml Aceton unter starkem Rühren bei Raumtemperatur versetzt. Die über Nacht ausgefallenen Kristalle werden dreimal mit Aceton p.A. gewaschen und im Vakuum bei 30°C getrocknet. Das so entstandene Produkt AM1M (N-Carbomethoxymethyl-N-methacryloylamidopropyl-N,N-dimethylammoniumchlorid) wird bis zur weiteren Verarbeitung im Exsikkator über Calciumchlorid aufbewahrt.The Alkylammonium chloride AM1M is prepared from starting material A: methacrylic acid (3-dimethylaminopropylamide) and the starting material B: chloroacetic acid methyl ester. For this purpose, 17.03 g (equivalent to 0.1 mol) of methacrylic acid (3-dimethylaminopropylamide) [MW 170.25] dissolved in 40 ml of acetone and with a solution of 11.94 g (corresponds to 0.11 mol) of methyl chloroacetate [MW 108.52] in 20 ml of acetone with vigorous stirring at room temperature. The crystals precipitated overnight are washed three times with acetone p.A. washed and dried in vacuo at 30 ° C. The resulting product AM1M (N-carbomethoxymethyl-N-methacryloylamidopropyl-N, N-dimethylammonium chloride) is until further processing in the desiccator via calcium chloride kept.
Alle Alkylammoniumchloride konnten mit einer Ausbeute größer als 90% des theoretischen Wertes hergestellt werden. Bei allen Alkylammoniumchloriden handelt es sich um feste (kristalline) Substanzen, die in bekannten flüssigen Monomeren gelöst unkritisch in der Hitze polymerisiert werden konnten.All Alkylammonium chlorides could be obtained with a yield greater than 90% of the theoretical value are produced. For all alkylammonium chlorides are solid (crystalline) substances that are known in the art liquid Dissolved monomers could be polymerized uncritically in the heat.
Zur Herstellung des Kontaktlinsenmaterials wurden neben einem Alkylammoniumhalogenid beispielsweise eine oder mehrere der Substanzen 2-Hydroxyethymethacrylat (HEMA), Ethy lenglycoldimethacrylat (EGA), 2-(2'-Hydroxy-5'-methacryloyloxyethylphenyl)-2H-benzotriazol (UVA), Isobornylmethacrylat (IBMA), 2,2'-Azobis-(2,4-dimethylvaleronitril) (V-65), 2,2'-Azobis-(2-methylbutyronitril) (V59) und Poly-(ethylenglykol)-methacrylat (Poly-glykol-MA) den entsprechenden Produktionsansätzen entnommen und entweder zu Stangenmaterial oder direkt zu Kontaktlinsen verarbeitet. Beispielsweise bestand ein Produktionsansatz aus 83,7 Gew.-% HEMA, 15 Gew.-% AM2E, 0,4 Gew.-% EGA, 0,5 Gew.-% UVA und 0,4 Gew.-% V65.to Preparation of the contact lens material was in addition to an alkylammonium halide For example, one or more of the substances 2-hydroxyethymethacrylate (HEMA), ethylene glycol dimethacrylate (EGA), 2- (2'-hydroxy-5'-methacryloyloxyethylphenyl) -2H-benzotriazole (UVA), Isobornyl methacrylate (IBMA), 2,2'-azobis (2,4-dimethylvaleronitrile) (V-65), 2,2'-azobis (2-methylbutyronitrile) (V59) and poly (ethylene glycol) methacrylate (poly-glycol-MA) den appropriate production approaches taken and either to bar stock or directly to contact lenses processed. For example, one production approach was 83.7 Wt .-% HEMA, 15 wt .-% AM2E, 0.4 wt .-% EGA, 0.5 wt .-% UVA and 0.4% by weight V65.
Zur Herstellung von Stangenmaterial wurden Röhrchen aus Polypropylen (PP-natur, 16×13 mm, 235 mm; Fa. Gehr) mit einer Füllmenge von 16 g pro Rohr beladen. Nach dem Füllen wurden die Röhrchen mit Stickstoff für 10 Minuten begast und anschließend die Polymerisation mit folgendem Temperatur-/Zeit-Programm durchgeführt: 45°C/24 h; 60°C/24 h; 90°C/24 h. Nach deren Entformung wurden die Stangen bei 90°C/24 h getempert.to Polypropylene tubes (PP natural, 16 × 13 mm, 235 mm; Fa. Gehr) loaded with a capacity of 16 g per tube. After filling were the tubes with nitrogen for Fumigated for 10 minutes and then the polymerization was carried out with the following temperature / time program: 45 ° C / 24 h; 60 ° C / 24 h; 90 ° C / 24 h. To their demoulding, the rods were annealed at 90 ° C / 24 h.
Zur direkten Herstellung von Kontaktlinsen wurde der Reaktionsansatz in Polypropylen-Förmchen eingefüllt und die Kontaktlinse während einer Stunde bei 100°C abgeformt. Die Polymerisation kann jedoch auch mit UV-Licht (λ = 300–400 nm, 3–6 mW/cm2, für 3 Stunden bei Raumtemperatur) beispielsweise mit Darocur 1173 (Ciba-Geigy Corp.) als Photoinitiator durchgeführt werden. Die Monomermenge betrug durchschnittlich 70 μl pro Förmchen. Die Quellung erfolgte in physiologischer Kochsalzlösung unter Sterilisationsbedingungen (121°C während 20 min).For the direct production of contact lenses, the reaction mixture was filled in polypropylene molds and molded the contact lens for one hour at 100 ° C. However, the polymerization can also with UV light (λ = 300-400 nm, 3-6 mW / cm 2 , for 3 hours at room temperature), for example, with Darocur 1173 (Ciba-Geigy Corp.) as a photoinitiator. The amount of monomer averaged 70 μl per mold. The swelling was carried out in physiological saline under sterilization conditions (121 ° C for 20 min).
Das erfindungsgemäße Kontaktlinsenmaterial besitzt die im Folgenden für AM1E beispielhaft gezeigte Struktur: The contact lens material according to the invention has the structure shown by way of example below for AM1E:
Das Kontaktlinsenmaterial ist physiologisch gesehen als Polymer nicht toxisch. Die Extraktion von nicht polymerisierten Restmonomeren aus dem Kontaktlinsenmaterial gestaltet sich einfach, da die verwendeten Monomere voll wasserlöslich sind.The Contact lens material is physiologically not as a polymer toxic. The extraction of unpolymerized residual monomers From the contact lens material is designed simply because the used Monomers fully water-soluble are.
Bevorzugt können weitere Monomere oder auch Copolymere in das Basismaterial einpolymerisiert sein. Dieses sind zum einen UV-absorbierende Substanzen. Erfindungsgemäße Kontaktlinsen, die beispielsweise mit 0,5 Gew.-% UV-Absorber ausgerüstet sind, eine Lichttransmission von 2% UVB, 8% UVA und 98% sichtbarem Licht. Zum anderen besteht die Möglichkeit Substanzen mit bakterizider und/oder fungizider Wirkung einzupolymerisieren. Beispielsweise könnte hierzu ein bereits bei der Medikamentenherstellung eingesetzter Hilfsstoff (MetoHEXAL/Hexal) als Copolymeres, das u.a. aus N-Methacryloyloxyethyl-N,N,N-trimethylammoniumchlorid hergestellt wird, Verwendung finden: Poly(ethylacrylat-co-methylmethacrylat-co-2-trimethylammonioethyl)methacrylatchlorid Preferably, further monomers or else copolymers can be copolymerized into the base material. These are on the one hand UV-absorbing substances. Inventive contact lenses, which are equipped, for example, with 0.5 wt .-% UV absorber, a light transmission of 2% UVB, 8% UVA and 98% visible light. On the other hand, it is possible to polymerize substances having a bactericidal and / or fungicidal action. For example, an excipient (MetoHEXAL / Hexal) already used in the manufacture of medicaments could be used as copolymer, which is prepared, inter alia, from N-methacryloyloxyethyl-N, N, N-trimethylammonium chloride. methacrylate chloride poly (ethyl acrylate-co-methyl methacrylate-co-2-trimethylammonioethyl)
Als weiteres Beispiel könnte sich auch die bakterizide und fungizide Wirkung durch das copolymerisierte AMB ergeben, dessen Monomerstruktur dem bereits in Pflegemitteln als Bakterizid verwendetem Benzalkoniumchlorid ähnlich ist: As a further example, the bactericidal and fungicidal action could also result from the copolymerized AMB, the monomer structure of which is similar to the benzalkonium chloride already used in care products as a bactericide:
Der Vorteil von in das Kontaktlinsenmaterial polymerisierten funktionellen Gruppen mit bakterizider und/oder fungizider Wirkung besteht darin, dass die Wahrscheinlichkeit eines Bewuchses der erfindungsgemäßen Kontaktlinse mit (pathogenen) Organismen dauerhaft und von Anfang an verringert ist. Damit verbunden ist auch, dass die Kontaktlinsen nicht mehr intensiv mit Reinigungslösungen gereinigt werden müssen, die oftmals in der Kontaktlinsenmatrix verbleiben und beim Tragen der Kontaktlinse zu einer Reizung des Auges führen.Of the Advantage of functionalized in the contact lens material polymerized Groups with bactericidal and / or fungicidal activity is that the probability of fouling of the contact lens according to the invention with (pathogenic) organisms permanently and reduced from the beginning is. Connected with this is also that the contact lenses no longer intensive with cleaning solutions need to be cleaned which often remain in the contact lens matrix and when worn the contact lens lead to irritation of the eye.
Die aus dem erfindungsgemäßen Kontaktlinsenmaterial gefertigte erfindungsgemäße Hydrogel-Kontaktlinse besitzt in hydratisierter Form einen Wassergehalt über 50 Gew.-%, bevorzugt zwischen 54 und 70 Gew.-%, mit gegenüber bekannten Hydrogel-Kontaktlinsen verbessertem Wasserrückhalteverhalten. Besonders vorteilhaft ist auch, dass sich die Oberfläche der Kontaktlinsen seifig anfühlt und damit zu einem angenehmen Tragegefühl beiträgt. Dabei ist die Kontaktlinse gleichzeitig äußerst reißfest und auch Hitze-sterilisierbar.The from the contact lens material according to the invention fabricated hydrogel contact lens according to the invention has in hydrated form a water content above 50 wt .-%, preferably between 54 and 70 wt .-%, compared to known hydrogel contact lenses improved water retention behavior. It is also particularly advantageous that the surface of the Contact lenses feel soapy and thus contributes to a comfortable fit. Here is the contact lens at the same time extremely tear-resistant and also heat sterilizable.
Ein besonderer Vorteil des erfindungsgemäßen Kontaktlinsenmaterials ist, dass es sich dabei im Gegensatz zu den bekannten anionischen Kontaktlinsenmaterialien um kationische Polymere handelt. Im physiologischen pH-Wertebereich kann das Halogenid-Ion nämlich nicht abgespalten und durch andere Anionen (z.B. saure Proteine) ersetzt werden. Damit aber bleiben die Eigenschaften der Kontaktlinse konstant. So könnte beispielsweise eine Veränderung der Quellung oder eine verstärkte Adsorptionsfähigkeit des Kontaktlinsenmaterials für Proteine erst durch Behandlung mit einer 2n Natronlauge (pH > 12) erreicht werden, da erst bei diesem pH-Wert die OH-Form des Alkylammoniumhalegonids, das Salz einer schwachen Base und einer starken Säure ist, erhalten wird.One particular advantage of the contact lens material according to the invention is that it is in contrast to the known anionic Contact lens materials are cationic polymers. In the physiological pH range, the halide ion namely not split off and be replaced by other anions (e.g., acidic proteins). In order to but the properties of the contact lens remain constant. For example a change of Swelling or a reinforced adsorption capacity of the contact lens material for Proteins can only be achieved by treatment with a 2N sodium hydroxide solution (pH> 12), since it is only at this pH that the OH form of the alkylammonium halide, the salt of a weak base and a strong acid, is obtained.
Das erfindungsgemäße Kontaktlinsenmaterial kann auch als Silicon-Hydrogel Verwendung finden (siehe Tabelle 1: AMSi). Hierzu ist die Substitution einer Alkylgruppe des Ammoniumsalzes (Ammoniumchlrid, -jodid, -bromid etc.) durch eine Silicium-haltige organische Verbindung, z.B. Trimethoxysilan-(m,p-chlormethyl)-phenylethan, notwendig. Mit einer derartigen Substanz wird ein „multifunktionelles Monomer" erhalten, mit dem sowohl der Wassergehalt, der über die Ammoniumfunktion vorgegeben ist, als auch die Sauerstoffdurchlässigkeit (Dk-Wert) einzustellen ist, die durch den Siliciumgehalt des Polymers geregelt wird.The Contact lens material according to the invention can also be used as silicone hydrogel (see table 1: AMSi). For this purpose, the substitution of an alkyl group of the ammonium salt (Ammonium chloride, iodide, bromide, etc.) by a silicon-containing organic compound, e.g. Trimethoxysilane (m, p-chloromethyl) phenylethane, necessary. With such a substance is a "multifunctional Monomer "obtained with the water content given by the ammonium function is to adjust as well as the oxygen permeability (Dk value) which is controlled by the silicon content of the polymer.
Außerdem ist der Einsatz von Silicium-haltigen Ammoniumsalzen für die Einstellung der hydrophilen Oberfläche von RGP (Rigid Gas Permeable)-Kontaktlinsen vorteilhaft. Im Gegensatz zur derzeit eingesetzten Methacrylsäure enthält das erfindungsgemäße hydrophile Monomer Silicium und erhöht dadurch neben der Hydrophilität, den Dk-Wert des Materials.Besides that is the use of silicon-containing ammonium salts for the adjustment the hydrophilic surface of RGP (Rigid Gas Permeable) contact lenses advantageous. In contrast to the currently used methacrylic acid contains the inventive hydrophilic Monomer silicon and increased in addition to the hydrophilicity, the Dk value of the material.
Schließlich können die erfindungsgemäßen Polymere auch unter Bedingungen der Lösungspolymerisation als wasserlösliche Substanzen hergestellt und in Form eines Kontaktlinsen-Pflegemittels angeboten werden. Die Kontaktlinsen würden während der Pflege mit einer gleitfähigen Schicht überzogen und gleichzeitig bevorzugt durch ein makromolekulares Desinfektionsmittel, das nicht in die Kontaktlinsenmatrix eindringen kann, keimfrei gemacht. Finally, the polymers of the invention can also be prepared under conditions of solution polymerization as water-soluble substances and offered in the form of a contact lens care product. The contact lenses would be coated with a lubricious layer during care and, at the same time, preferably germ-free by a macromolecular disinfectant that can not penetrate the contact lens matrix.
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