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Macroinitiator containing hydrophobic segment

a technology of hydrophobic segments and micro-initiators, which is applied in the field of micro-initiators, can solve the problems that large polysiloxane segments are difficult to solubilize in aqueous solutions

Inactive Publication Date: 2012-11-08
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 about a type of chemical called macroinitiators, which have a specific part that is not very soluble in water. The size of this part is important - it should be between 300 and 1800. This invention is useful for making certain types of polymers.

Problems solved by technology

However, large polysiloxane segments can be difficult to solubilize in aqueous solutions, such as contact lens packaging, cleaning and care solutions.
This can result in cloudy solutions which do not impart the desired improvement in wettability to the articles being treated.

Method used

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  • Macroinitiator containing hydrophobic segment
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  • Macroinitiator containing hydrophobic segment

Examples

Experimental program
Comparison scheme
Effect test

working example 1

[0082]1.68 g (6 mmol) of 4,4′-azobis(4-cyanovalearic acid) and 1.83 g (15 mmol) of 4-dimethyl amino pyridine, 3.0 g (15 mmol) of N,N-dicyclohexyl carbodiimide, and 40 mL of acetone were added to a 200 mL three mouth flask equipped with a calcium chloride tube under nitrogen gas flow. 8.58 g (9 mmol) of polydimethylsiloxane having a hydroxyl group at one end and expressed by the following formula (a2)

(manufactured by Chisso Corporation FM-0411, Mw 1000) was added by drops to the solution and agitated for six hours at room temperature. A precipitated solid was filtered out, hexane was added to the filtrate obtained, and then the filtrate was washed two times with 0.5 N HCl, two times with saturated sodium bicarbonate aqueous solution, and one time with saturated sodium chloride aqueous solution. The organic phase was dried using sodium sulfate, filtered, and then concentrated to obtain crude product. The crude product was purified using a silica gel column (silica gel 180 g, hexane / et...

working example 2

[0083]1.40 g (5 mmol) of 4,4′-azobis(4-cyanovalearic acid), 9.1 g (9.1 mmol) of polydimethylsiloxane having an amino group at one end and expressed by the following formula (a3) (manufactured by Chisso Corporation, FM0311, Mw 1000), 0.67 g (5.5 mmol) of 4-dimethyl aminopyridine, and 50 mL of acetone were added to a 200 mL three mouth flask equipped with a calcium chloride tube under nitrogen gas flow.

1.70 mL (11 mmol) of N,N-diisopropyl carbodiimide was added by drops to this blended solution. After agitating for 6 hours at ambient temperature, a precipitated solid was filtered out, hexane was added to the filtrate obtained, and then the filtrate was washed two times with 0.5 N HCl, two times with saturated sodium bicarbonate aqueous solution, and one time with saturated sodium chloride aqueous solution. The organic phase was dried using sodium sulfate, filtered, concentrated, and then the crude product was purified using a silica gel column (silica gel 180 g, hexane / ethyl acetate=1...

working example 3

[0086]N-vinyl pyrrolidone (NVP, 29.56 g, 0.266 mol), the silicone macro initiator expressed by the following formula (a4) obtained by working example 1 (Mw of silicone portion is 1000, 0.19 g, 0.0866 mmol), and t-amyl alcohol (TAA, 69.42 g) were added to a 200 mL three mouth flask, and then a three way cock, thermometer, and mechanical stirrer were attached.

The inside of the three mouth flask was evacuated using a vacuum pump and then substituted with argon, three times, and then the temperature was increased to 70° C. After confirming that the temperature had stabilized and heat generation was not occurring, the temperature was increased to 75° C. and the sample was agitated for 6 hours.

[0087]After polymerization was complete, the temperature was cooled to room temperature, and then the sample was poured into n-hexane / ethanol=500 mL / 40 mL and allowed to sit. The supernatant fluid was removed by decanting, and then the washing was performed 2 times using n-hexane / ethanol=500 mL / 20 m...

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Abstract

The present invention relates to macroinitiators comprising at least one hydrophobic segments in a molecule, wherein a molecular weight of the hydrophobic segment is 300 to 1800. The present invention further relates to block copolymers, wetting agent and polymeric materials having the block copolymers of the present invention associated with, which is suitable for medical devices, particularly for ophthalmic devices, including contact lenses, ophthalmic lenses, punctal plugs and artificial corneas.

Description

RELATED APPLICATIONS[0001]This application claims priority to U.S. Provisional Patent Application No. 61 / 482,260, filed on May 4, 2011 entitled MACROINITIATOR CONTAINING HYDROPHOBIC SEGMENT, the contents of which are incorporated by reference.FIELD OF THE INVENTION[0002]The present invention relates to macroinitiators useful for forming block copolymers. The present invention further relates to block copolymers, wetting agents and polymeric materials, as well as, medical devices incorporating the polymeric materials having the block copolymers of the present invention.DESCRIPTION OF THE RELATED ART[0003]Various compounds have been disclosed as suitable for treating preformed silicone hydrogel contact lenses including surface active segmented block copolymers, substantially water-soluble silicone-containing surfactants, functionalized hybrid PDMS / polar amphipathic compolymer block systems, including polydimethylsiloxane-PVP block copolymers and (meth)acrylated polyvinylpyrrolidone. W...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08L83/08C08G77/455C08G77/26
CPCC08G77/26C08G77/388C08L83/08G02B1/043A61L27/18A61L2430/16C08G77/452C08L101/14C08L83/04G02B1/04A61L12/14C08L83/10G02B1/18C08L2201/10C08L2201/54C08L2203/02
Inventor TAMIYA, RYUTAFUJISAWA, KAZUHIKONAKAMURA, MASATAKA
Owner JOHNSON & JOHNSON VISION CARE INC
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