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Low-tack ophthalmic and otorhinolaryngological device materials

An ENT and device technology, applied in the field of acrylic device materials

Inactive Publication Date: 2009-12-30
ALCON INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The macromer additive is a methacrylate terminated polystyrene macromer

Method used

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  • Low-tack ophthalmic and otorhinolaryngological device materials
  • Low-tack ophthalmic and otorhinolaryngological device materials
  • Low-tack ophthalmic and otorhinolaryngological device materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Synthesis of 4-phenylbutyl methacrylate ("PBMA").

[0048]

[0049] Into a three-necked round-bottomed flask equipped with a Teflon-coated magnetic stirring bar, 120 mL (1.09 mol) of methyl methacrylate (2), 5.35 g (0.015 mol) of tetrabutoxytitanium (Ti( OC 4 h 9 ) 4 ), 60 mL (0.39 mol) of 4-phenyl-1-butanol (1) and 14.6 g (0.073 mol) of 4-benzyloxyphenol (4-BOP). Attach the addition funnel, thermometer and short path distillation head with thermometer and receiving flask to the neck of the flask. The flask was placed in an oil bath and the temperature was raised until distillation started. Methyl methacrylate (2) was placed in the addition funnel and added dropwise at the same rate as the distillation. The reaction mixture was heated for 4 hours, then cooled to room temperature. The crude product was vacuum distilled and 62.8 g (0.29 mol, 74%) of a clear, colorless liquid 4-phenylbutyl methacrylate (3) was isolated.

Embodiment 2

[0050] Embodiment 2: Synthesis of 3-benzyloxypropyl methacrylate.

[0051]

[0052] Into a three-necked round-bottomed flask equipped with a Teflon-coated magnetic stirring bar, 95 mL (0.884 mol) of methyl methacrylate (2), 4.22 g (0.012 mol) of tetrabutoxytitanium (Ti( OC 4 h 9 ) 4 ), 50 mL (0.316 mol) of 3-benzyloxy-1-propanol (1) and 14.6 g (0.073 mol) of 4-benzyloxyphenol (4-BOP). Attach the addition funnel, thermometer and short path distillation head with thermometer and receiving flask to the neck of the flask. The flask was placed in an oil bath and the temperature was raised until distillation started. Methyl methacrylate (2) was placed in the addition funnel and added dropwise at the same rate as the distillation. The reaction mixture was heated for 4 hours, then cooled to room temperature. The crude product was vacuum distilled and 36.5 g (0.156 mol, 49%) of a clear, colorless liquid 3-benzyloxypropyl methacrylate (3) was isolated. Example 3: Preferred Int...

Embodiment 3

[0053] Preferred intraocular lens materials are shown below. All amounts are expressed in % by weight. The formulation may be initiated with a peroxy radical initiator, such as 1% bis(4-tert-butylcyclohexyl) peroxydicarbonate ("PERK 16S").

[0054] Element

[0055]The chemicals are weighed, mixed and filtered together. The resulting formulation solution was flushed with nitrogen and transferred to a glove box with a hypoxic atmosphere. The formulation was then pipetted into degassed polypropylene molds. The assembled mold was then transferred to an oven and cured at 90°C for 1 hour, followed by post-curing at 110°C for 1 hour. After cooling the polymer samples were removed from the mold. The low viscous nature of the sample is evident in this step of preparation. The samples were extracted with acetone and dried under vacuum. Subsequent tack evaluations indicated that the material had low tack relative to a control sample containing no PSMA.

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Abstract

Disclosed are soft, high refractive index, acrylic materials. These materials, especially useful as intraocular lens materials, contain an aryl acrylic hydrophobic monomer as the single principal device-forming monomer and a tack-reducing macromer additive. In addition to their use as intraocular lens materials, the present materials are also suitable for use in other ophthalmic or otorhinolaryngological devices, such as contact lenses, keratoprostheses, corneal inlays or rings; otological ventilation tubes and nasal implants.

Description

field of invention [0001] This invention relates to acrylic device materials. In particular, the present invention relates to low tack, high refractive index acrylic device materials that are particularly useful as intraocular lens ("IOL") materials. Background of the invention [0002] With recent advances in small-incision cataract surgery, more emphasis has been placed on developing soft, foldable materials suitable for artificial lenses. In general, these materials fall into one of three categories: hydrogels, silicones, and acrylics. [0003] Typically, hydrogel materials have a low refractive index, so they are less ideal than other materials because thicker lenses are required to achieve a specific refractive power. Silicone materials typically have a higher refractive index than hydrogels, but when placed in the eye in a folded state, they tend to unfold explosively. Explosive deployment may damage the corneal endothelium and / or rupture the natural lens capsule. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61F2/24A61F2/16A61L27/14A61L27/16G02B1/04
CPCG02B1/043A61L27/16A61L2430/16C08L33/04C08L25/08C08L33/08C08L25/04A61L27/14A61F2/16G02B1/04
Inventor D·M·科尔多瓦M·卡拉克勒C·勒曼D·C·施吕特J·I·魏因申克三世
Owner ALCON INC
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