Hydrogel copolymers for biomedical devices

A copolymer and hydrogel technology, applied in the field of biomedical device formation, can solve problems such as damage to oxygen permeability, damage to the cornea, and uncomfortable contact lenses

Inactive Publication Date: 2008-03-05
BAUSCH & LOMB INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To make contact lenses more wettable or comfortable, higher water content is required, but higher water content impairs oxygen permeability
Additionally, contact lenses with too high a tensile modulus may be less comfortable, or even damage the cornea when worn for extended periods of time

Method used

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  • Hydrogel copolymers for biomedical devices
  • Hydrogel copolymers for biomedical devices
  • Hydrogel copolymers for biomedical devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0117] Preparation of α, ω-bis(4-hydroxybutyl)polydimethylsiloxane (Mn about 5000)

[0118] The following components were added to a 2-L three-necked round bottom flask equipped with a reflux condenser: 51.26 grams of 1,3-bishydroxybutyltetramethyldisiloxane; 1085 grams of dimethoxydimethylsilane; 157.8 grams of distilled water; and 18.4 mL of concentrated hydrochloric acid. The mixture was heated at 60 °C for 1 hour. Then, methanol was distilled off over 5 hours, and 552 mL was collected. Then, 349 mL of distilled water and 349 mL of concentrated HCl were added, and the contents were refluxed at 100° C. for 3 hours. Then, the crude product was separated from the aqueous layer. Add 600 mL of diethyl ether (ether) and 400 mL of deionized water, and extract twice with 400 mL of sodium bicarbonate (0.5%), and wash twice with distilled water until the washing liquid has a neutral pH. The product (655.8 g) was then added slowly to a methanol / water mixture (508.2 g / 147.97 g). T...

Embodiment 2

[0120] Preparation of α, ω-bis(4-hydroxybutyl)polydimethylsiloxane (Mn about 2700)

[0121] This polysiloxane was prepared according to the general procedure of Example 1, except that the molar ratio of 1,3-bishydroxybutyltetramethyldisiloxane and dimethoxydimethylsilane was changed to about 1:28. alkyl. The molecular weight (Mn) determined by titration was 2730.

Embodiment 3

[0123] Preparation of polydimethylsiloxane-based prepolymers using the PDMS of Example 1 and comprising units of formula (I) and (II)

[0124] A 500 mL dry 3-neck round bottom flask was connected with a nitrogen inlet tube and a reflux condenser. The following components were added in one portion to the flask: isophorone diisocyanate (2.111 g, 9.497 mmol) (IPDI), diethylene glycol (0.498 g, 4.696 mmol) (DEG), dibutyltin dilaurate (0.161 g) and 150 mL of dichloromethane. Reflux the contents. After overnight, the amount of isocyanate was reduced to 43.3% by titration. Then, α,ω-bis(4-hydroxybutyl)polydimethylsiloxane from Example 1 (45.873 g, 9.557 mmol) was added to the flask. Reflux was continued overnight and residual unreacted isocyanate was determined by titration. Then, IPDI (1.261 g, 5.673 mmol) was added and reflux was continued overnight. The amount of isocyanate was reduced to 22.9% as determined by titration. Cool the contents to ambient temperature. 1,1'-bis-2...

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Abstract

Hydrogel copolymers which are hydrated polymerization products of monomeric mixtures comprising polysiloxane prepolymers and hydrophilic comonomers are useful for forming biomedical devices, particularly ophthalmic devices including contact lenses, intraocular lenses and ophthalmic implants. The copolymers have a desirable combination of oxygen permeability, tensile modulus, and water content, especially for soft contact lenses.

Description

technical field [0001] The present invention relates to hydrogel copolymers for use in forming biomedical devices, particularly ophthalmic devices, including contact lenses, intraocular lenses and ophthalmic implants. The copolymer has a desirable combination of oxygen permeability, tensile modulus and water content, especially for soft contact lenses. Background technique [0002] Hydrogels represent a satisfactory class of materials for the fabrication of various biomedical devices including ophthalmic devices such as contact lenses. Hydrogels are hydrated crosslinked polymer systems that contain water in equilibrium. Hydrogel lenses provide satisfactory biocompatibility and comfort. Silicone hydrogels are a known class of hydrogels characterized by the inclusion of silicone-containing materials. Usually silicone-containing monomers are copolymerized with hydrophilic monomers by free radical polymerization, and silicone-containing monomers or hydrophilic monomers that a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/61C08G18/67C08F290/06C08F290/14G02B1/04A61L27/16A61L27/52
CPCC08G2210/00A61L27/52C08G18/10A61L27/165G02B1/043C08G18/672C08F290/06A61L27/18C08G18/8016C08F290/14C08L53/00C08L33/02C08L39/06C08L33/26C08L83/04C08L39/04C08L51/085C08G18/3206C08G18/61C08L51/08C08L2666/02C08G77/42G02C7/04
Inventor 赖有进W·郎E·T·奎因D·V·鲁西奥
Owner BAUSCH & LOMB INC
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