Ionically modified silicones, compositions, and medical devices formed therefrom

An organosilicon compound, the technology of the compound, which is applied in the directions of medical preparations without active ingredients, medical preparations containing active ingredients, instruments, etc., can solve the problems of restricting the curative effect, blurring, long contact time, etc.

Active Publication Date: 2019-11-08
MOMENTIVE PERFORMANCE MATERIALS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, significant drug loss occurs upon administration of eye drops as the drug is diluted and washed out by reflex tear flow and blinking or excretion through the nasolacrimal system,

Method used

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  • Ionically modified silicones, compositions, and medical devices formed therefrom
  • Ionically modified silicones, compositions, and medical devices formed therefrom
  • Ionically modified silicones, compositions, and medical devices formed therefrom

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0225] Example 1: 4-(2(-Acryloyloxy)-4-(2-(1,1,1,3,5,5,5-heptamethyltrisiloxane-3-yl)ethyl ) cyclohexyl) oxy-4-oxobutyric acid synthesis

[0226] To a round bottom flask equipped with a stir bar, reflux condenser and dropping funnel was added 100 grams of vinylcyclohexyl epoxy functionalized trisiloxane, and toluene, and the reaction mixture was heated to 70-75°C. At this point, catalytic amounts of titanium isopropoxide and TEMPO (2,2,6,6-tetramethylpiperidine 1-oxy) were added and the reaction mixture was further heated to 90°C. To the reaction mixture was gradually added 21 grams of acrylic acid. After completion, the reaction mixture was passed over Dowex-WBA resin to remove unreacted acrylic acid. The product was decolorized using activated carbon and filtered over a bed of diatomaceous earth. The filtrate was vacuum stripped to yield the pale yellow product 5-(2-(1,1,1,3,5,5,5,-heptamethyltrisiloxane-3-yl)ethyl)-2 - Hydroxycyclohexyl acrylate.

[0227] Further 5-(2-...

Embodiment 2

[0228] Example 2: (4-(((2-(acryloyloxy)-5-(2-(1,1,1,3,5,5,5-heptamethyltrisiloxane-3-yl Synthesis of )ethyl)cyclohexyl)oxy)-4-oxobut-2-enoic acid

[0229] 5-(2-(1,1,1,3,5,5,5,-heptamethyltrisiloxane-3-yl)ethyl)-2-hydroxycyclohexylacrylate (50 g), Toluene and maleic anhydride (18 grams) were further added to a round bottom flask equipped with a stir bar, reflux condenser and nitrogen inlet. To this were added triethylamine and hydroquinone as catalyst and free radical scavenger respectively and the reaction mixture was heated to 60-65°C. After completion, the product was vacuum stripped, redissolved in chloroform, and washed with brine solution. The organic phase was passed over Tulsion T66-MP resin to remove traces of triethylamine and decolorized using activated carbon. The organic layer was concentrated after removal of the charcoal to yield a pale yellow viscous product.

Embodiment 3

[0230] Example 3: 3-(((2-(acryloyloxy)-5-(2-(1,1,1,3,5,5,5-heptamethyltrisiloxane-3-yl) Synthesis of ethyl)cyclohexyl)oxy)carbonyl)but-3-enoic acid

[0231] To a round bottom flask equipped with a stir bar, reflux condenser and nitrogen inlet was added 5-(2-(1,1,1,3,5,5,5,-heptamethyltrisiloxane-3-yl) ethyl)-2-hydroxycyclohexyl acrylate (50 g) and toluene. To this were added triethylamine and hydroquinone as catalyst and free radical scavenger respectively and the reaction mixture was heated to 60-65°C. To this was gradually added itaconic anhydride (20 g). After completion, the product was vacuum stripped, redissolved in chloroform, and washed with brine solution. The organic phase was passed over Tulsion T66-MP resin to remove traces of triethylamine and decolorized using activated carbon. The organic layer was concentrated after removal of the charcoal to yield a pale yellow viscous product.

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Abstract

A hydrophilic silicone, compositions comprising the same, and articles comprising the same are shown and described herein. The hydrophilic silicone is an ionically modified silicone compound wherein the compound has a net neutral charge. The hydrophilic silicone compounds may be provided as part of a composition, e.g., a composition suitable for forming a hydrogel, which may be employed to form afilm material and even an article (e.g., in a contact lens).

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS [0002] This application claims priority to and the benefit of US Provisional Application No. 62 / 459,632, filed February 16, 2017, the entire disclosure of which is incorporated herein by reference in its entirety. technical field [0003] The present invention relates to organosilicon compounds and compositions comprising such compounds. Specifically, there are provided ionically modified organosilicon compounds having an overall charge that is net neutral, compositions comprising such organosilicon compounds, active delivery systems incorporating hydrogels formed from such compositions, and Articles formed from such compositions. Background technique [0004] Long-term continuous wear contact lenses (contact lenses) are made of silicone rubber prepared from polydimethylsiloxane. Since silicone rubber contact lenses are very hydrophobic and distinct from the cornea in thermal properties such as thermal conductivity and therm...

Claims

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Application Information

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IPC IPC(8): C09D183/08C08G77/26C08G77/28C08G77/30C08G77/20C09D183/06C08G77/38C08G77/388
CPCC09D183/06C09D183/08C08G77/20C08G77/26C08G77/38C08G77/388A61K47/6903A61K9/0051A61K9/7023A61K47/34C08G77/045C08G77/18C08G2210/00G02B1/043A61K9/06A61K45/06C08G77/06C08G77/22C08G77/392C08F230/08
Inventor M.梅赫拉R.梅赛德S.布哈特
Owner MOMENTIVE PERFORMANCE MATERIALS INC
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