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Medical devices having homogeneous charge density and methods for making same

a technology of homogeneous charge density and medical devices, applied in the field of ionic silicone hydrogels and ophthalmic devices, can solve the problems of increased moduli and non-hydrolytic stability of contact lenses

Inactive Publication Date: 2013-08-08
JOHNSON & JOHNSON VISION CARE INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention is related to an ionic, silicone hydrogel contact lens that includes a statistical copolymer comprising units derived from at least one non-ionic hydrophilic monomer and at least one anionic monomer. The lens has a specific contact angle, a certain level of lysozyme uptake, and a low uptake of polycationic components when contacted with an ophthalmic solution. Additionally, the invention relates to a silicone hydrogel formed from a reactive mixture comprising major polymerizable components and minor polymerizable components. The major components include at least one reactive silicone-containing component, at least one reactive ionic monomer, and optionally reactive hydrophilic components and crosslinker. The minor components can include visibility tint, dyes, UV absorbers, photochromic compounds, pharmaceutical compounds, nutriceutical compounds, and mixtures thereof.

Problems solved by technology

Unfortunately, attempts to add anionic components to silicone hydrogels in the past have produced contact lenses which are not hydrolytically stable and display moduli which increase when exposed to water and heat.

Method used

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  • Medical devices having homogeneous charge density and methods for making same
  • Medical devices having homogeneous charge density and methods for making same
  • Medical devices having homogeneous charge density and methods for making same

Examples

Experimental program
Comparison scheme
Effect test

preparation 1

[0164]N,N-dimethylacrylamide (DMA) and further purified via vacuum distillation. 5-acrylamidopentanoic acid (ACA2) was prepared according to Synthesis 3 The siloxy-functional benzyltrithiocarbonate, S-XG-1996-S′-hexyl-trithiocarbonate, was prepared according to Synthesis 1, above. Irgacure 819 was dissolved in D3O (10 mg / mL).

[0165]The polymerization solution was prepared by dissolving 1.1 g ACA2 in 3 mL of ethanol and 1.5 g DMA in an amber 20 mL glass vial. Next, 166 mg S-XG-1996-S′-hexyl-trithiocarbonate, and 1.51 mg (151 ul of stock solution) Irgacure-819 were added to the monomer and warmed / stirred to ensure homogeneity (CTA to initiator ratio=20). The amber vial containing the final polymerization solution was sealed with a rubber septum and purged for 20 minutes with N2 to remove O2 from the solution. Finally the sealed jar was placed in an N2 glove-box for storage.

[0166]The polymerization solution was cured under an N2 atmosphere with 4 standard Phillips TL 20W / 03 RS bulbs at ...

preparation 2

[0169]N,N-dimethylacrylamide (DMA) was purified via vacuum distillation. 5-acrylamidopentanoic acid (ACA2) was prepared according to Synthesis 3. The siloxy-functional benzyltrithiocarbonate, S-XG-1996-S′-hexyl-trithiocarbonate, was prepared according to Synthesis 1. Irgacure 819, was obtained from Ciba Specialty Chemicals and dissolved in D30 (10 mg / mL).

[0170]The polymerization solution was prepared by dissolving 2.07 g ACA2 in 6 mL ethanol and 300 mg DMA in an amber 20 mL glass vial. Next, 58 mg S-XG-1996-S′-hexyl-trithiocarbonate, and 1.06 mg (106 ul of stock solution) Irgacure-819 were added to the monomer and warmed / stirred to ensure homogeneity (CTA to initiator ratio=20). The amber vial containing the final polymerization solution was sealed with a rubber septum and purged for 20 minutes with N2 to remove O2 from the solution. Finally the sealed vial was placed in an N2 glove-box for storage. The polymerization solution was cured and purified as described in Preparation 1. Th...

examples 1-12

[0175]Three senofilcon lenses were removed from their packages and transferred glass vials containing packing solution containing the non-reactive polysiloxane terminated hydrophilic polymer (“NRPTHP”) produced in Preparation 1 through 4 in the concentrations shown in Table 1. The lenses were re-packaged in the NRPTHP packing solution, autoclaved at 121° C. for 28 minutes and, after sterilization, were allowed to soak in the NRPTHP packing solution at ambient temperature for at least 24 hours. The contact angle, lysozyme uptake and PQ-1 uptake of the lenses were measured and are reported in Table 3. Untreated senofilcon lenses were also tested as a control.

TABLE 3[NRPTHP]% PQ1LysozymeEx#PrepDMA:ionic(ppm)CA°uptake(μg / lens)1170:30ACA25024 ± 57 ± 119 ± 32170:30ACA250028 ± 60 ± 044 ± 73170:30ACA2100029 ± 70 ± 551 ± 64280:20ACA25024 ± 139 ± 033 ± 55280:20ACA250032 ± 1824 ± 9 58 ± 76280:20ACA2100033 ± 1646 ± 7 65 ± 47380:20ACA25017 ± 47 ± 523 ± 48380:20ACA250022 ± 1213 ± 1 43 ± 59380:20A...

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Abstract

The present invention relates to ionic silicone hydrogel polymers comprising at least one pharmaceutical or nutriceutical component and displaying improved lysozyme uptake, low contact angle and reduced water soluble polymeric ammonium salt uptake.

Description

RELATED APPLICATIONS[0001]This application is a continuation-in-part of U.S. patent application Ser. No. 13 / 449,413, filed on Apr. 18, 2012 entitled MEDICAL DEVICES HAVING HOMOGENEOUS CHARGE DENSITY AND METHODS FOR MAKING SAME, the contents of which are incorporated by reference.FIELD OF THE INVENTION[0002]The present invention relates to ionic silicone hydrogels, and ophthalmic devices formed therefrom, which display desirable tear and polycationic ophthalmic solution component uptake profiles and desirable drug uptake.BACKGROUND OF THE INVENTION[0003]It is well known that contact lenses can be used to improve vision. Various contact lenses have been commercially produced for many years. Hydrogel contact lenses are very popular today. These lenses are formed from hydrophilic polymers and copolymers containing repeating units from hydroxyethylmethylacrylate (HEMA). Of these contact lenses formed from copolymers of HEMA and methacrylic acid, are among the most comfortable, and have t...

Claims

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Application Information

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IPC IPC(8): A61K47/34A61K31/4535
CPCA61K47/34A61K31/4535G02B1/041G02B1/043C08L101/14C08L83/04A61K9/0051
Inventor MAHADEVAN, SHIVKUMARFADLI, ZOHRASCALES, CHARLES W.MAGGIO, THOMAS L.VENKATASUBBAN, KUNISIGEORGE, ERIC R.FORD, JAMES D.DAVIS, CARRIE L.HANSEN, LEAHJOSLIN, SCOTT L.RAJA, RANGANATHMUTHUKRISHNAN, SHARMILASURENDRAN, C.
Owner JOHNSON & JOHNSON VISION CARE INC