Ophthalmic and otorhinolaryngological device materials containing a multi-arm peg macromer

A technology of ENT and ophthalmology, applied in the field of ophthalmology and ENT device materials containing multi-arm PEG macromers

Inactive Publication Date: 2014-11-05
NOVARTIS AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Likewise, higher molecular weight PEG dimethacrylates cannot be mixed with hydrophobic acrylic monomers

Method used

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  • Ophthalmic and otorhinolaryngological device materials containing a multi-arm peg macromer
  • Ophthalmic and otorhinolaryngological device materials containing a multi-arm peg macromer
  • Ophthalmic and otorhinolaryngological device materials containing a multi-arm peg macromer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] Partially Methacrylated 2000M n Synthesis of 4-arm PEG, Batch #1

[0090] Commercially available 4-arm polyethylene glycol was degassed at 70°C for 4 days and then dissolved in about 100 ml THF. Triethylamine and p-methoxyphenol (ca. 50 mg) were added and the mixture was cooled to 0°C. Add methacryloyl chloride dropwise. Formation of triethylamine-HCl salt started immediately. The mixture was stirred at ambient temperature for 72 hours, then filtered through a plug of silica using a medium porosity sintered glass funnel. The silica was rinsed with dichloromethane so the total volume of the filtrate was about 500-700ml. The solvent was removed by rotary evaporation and the product was dried under vacuum for 3-4 days to give a light yellow liquid (yield 60%).

[0091] Reaction table showing the synthesis of 4-arm PEG using 1.5 equivalents of methacryloyl chloride

[0092]

Embodiment 2

[0094] Partially Methacrylated 2000M n Synthesis of 4-arm PEG, Batch #2

[0095] Procedure: same as Example 1. Pale yellow liquid (yield about 60%).

[0096] Reaction table showing the synthesis of 4-arm PEG using 3.5 equivalents of methacryloyl chloride

[0097]

Embodiment 3

[0099] IOL preparation

[0100] The multi-armed PEG derivatives from Examples 1 and 2 were formulated as shown in Tables 1 and 2. Specimens measuring a thickness of 0.9 mm were cured thermally at 70°C for 1 hour and at 110°C for 2 hours. Samples were extracted in acetone for 20 hours at 55°C, then slowly dried at ambient temperature for 20 hours, followed by vacuum (0.1 mm Hg) at 70°C for a minimum of 20 hours. The extractable weight percent, equilibrium water content (EWC), refractive index (R.I.) and plate appearance of the hydrated samples subjected to the 45-22°C ΔT test are shown in Table 3. The mechanical and thermal properties of selected compositions are shown in Table 4.

[0101] Table 1

[0102]

[0103] Table 2

[0104]

[0105]

[0106] table 3

[0107]

[0108] 1 Samples were equilibrated in deionized water for 9 days at 45°C, then cooled to ambient temperature and later examined by light microscopy using a 10X objective for 1-2 hours.

[0109] ...

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Abstract

Disclosed are soft, high refractive index, acrylic device materials. The materials contain a multi-arm PEG macromer.

Description

technical field [0001] The present invention relates to improved materials for ophthalmic and ENT devices. In particular, the present invention relates to soft, high refractive index, acrylic device materials comprising multi-armed polyethylene glycol macromers. Background of the invention [0002] With recent advances in small-incision cataract surgery, there has been increased emphasis on developing soft, foldable materials suitable for intraocular lenses. In general, these materials fall into one of three categories: hydrogels, silicon, and acrylic. [0003] In general, the relatively low refractive index of hydrogel materials makes them less desirable than other materials due to the thicker lens optics necessary to achieve a given refractive power. Traditional silicon materials typically have a higher refractive index than hydrogels, but tend to unfold explosively after being placed in the eye in a folded position. Explosive deployment may damage the corneal endotheli...

Claims

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Application Information

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IPC IPC(8): A61L27/16A61L27/50
CPCA61L27/50A61L2430/16A61L27/16C08L33/08
Inventor W·R·拉雷多
Owner NOVARTIS AG
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