Non-reactive, hydrophilic polymers having terminal siloxanes and methods for making and using the same

Patent metadata

Field	Value
Publication number	US-10301465-B2
Application number	US-201715723434-A
Country	US
Kind code	B2
Filing date	Oct 3, 2017
Priority date	May 6, 2010
Publication date	May 28, 2019
Grant date	May 28, 2019

Abstract

The present invention relates to compositions comprising at least one stable, near-monodisperse, non-reactive hydrophilic polymer comprising in said polymer's backbone, a hydrophilic segment having a degree of polymerization of about 10 to about 1000, and a linear silicone segment at at least one terminal end of said non-reactive hydrophilic polymer, wherein said silicone segment comprises between about 6 and about 200 siloxy units, and said non-reactive hydrophilic polymer is associated, via the linear silicone block with a silicone hydrogel. The non-reactive hydrophilic polymers may be incorporated into the formulation from which the silicone hydrogel is made or may be contacted with the silicone hydrogel post formation.

First claim

We claim:

1. An ophthalmic solution comprising at least one stable, non-reactive hydrophilic polymer comprising in said polymer's backbone, a hydrophilic segment having a degree of polymerization of about 300 to about 10,000, and a linear silicone segment at at least one terminal end of said non-reactive hydrophilic polymer, wherein said silicone segment comprises between about 6 and about 200 siloxy units, wherein said non-reactive hydrophilic polymer is present in a contact angle reducing amount and said ophthalmic solution is transparent, wherein said polymer has a polydispersity of less than about 1.5.

2. The ophthalmic solution of claim 1 wherein said at least one stable, non-reactive hydrophilic polymer comprises 6 to 60 siloxy repeat units.

3. The ophthalmic solution of claim 1 wherein said at least one stable, non-reactive hydrophilic polymer further comprises 6 to 20 siloxy repeat units.

4. The ophthalmic solution of claim 1 wherein said at least one stable, non-reactive hydrophilic polymer is present in an amount between about 0.005 and about 2%.

5. The ophthalmic solution of claim 1 wherein said at least one stable, non-reactive hydrophilic polymer is present in an amount between about 0.01 and about 0.5 weight %.

6. The ophthalmic solution of claim 1 wherein said hydrophilic segment of said non-reactive hydrophilic polymer has a degree of polymerization between about 500 and about 10,000.

7. The ophthalmic solution of claim 1 wherein said hydrophilic segment of said non-reactive hydrophilic polymer has a degree of polymerization between about 500 and about 5000.

8. The ophthalmic solution of claim 1 wherein hydrophilic segment and linear silicone segment are present in said non-reactive hydrophilic polymer in a ratio, based upon the degree of polymerization, between 13:1 and 500:1.

9. The ophthalmic solution of claim 8 wherein the ratio of hydrophilic segment to linear silicone segment, based upon degree of polymerization is between 70:1 and 200:1.

10. An ophthalmic solution comprising at least one stable, non-reactive hydrophilic polymer comprising in said polymer's backbone, a hydrophilic segment having a degree of polymerization of about 300 to about 10,000, and a linear silicone segment at at least one terminal end of said non-reactive hydrophilic polymer, wherein said silicone segment comprises between about 6 and about 200 siloxy units, wherein said non-reactive hydrophilic polymer is present in a contact angle reducing amount and said ophthalmic solution is transparent, and wherein said polymer is a polymer of Formula I:

wherein R 1 is selected from substituted and unsubstituted C 1-24 alkyl;
R 2 -R 5 are independently selected from H, C 1 -C 4 alkyl and C 6-10 aryl;
n is 6-20;
R 9 is selected from a direct bond and C 1-12 alkylene;
X is selected from the group consisting of —O—(CO)—, —(CO)O—, —NR 8 —(CO)—, —(CO)NR 8 —, —O—, or a direct bond;
R 8 is selected from H, methyl, ethyl or propyl;

R 6 is selected from the group consisting of alkylenes of the following formulae:

and aromatic groups of the following formulae:

Q is the hydrophilic segment,
Z is selected from the group consisting of hydrogen, chlorine, fluorine, optionally substituted alkyl, optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted alkylthio, optionally substituted alkoxy, optionally substituted alkoxycarbonyl, optionally substituted aryloxycarbonyl (—COOR″), carboxy (—COOH), optionally substituted acyloxy (—O 2 CR″), optionally substituted carbamoyl (—CONR″ 2 ), cyano (—CN), dialkyl- or diaryl-phosphonato [—P(═O)(OR″) 2 ], dialkyl- or diaryl-phosphinato [—P(═O)(OR″) 2 ];
t is 1 or an integer greater than 1 and p is an integer of 1-5.

11. The ophthalmic solution of claim 10 wherein
R 1 is selected from the group consisting of substituted and unsubstituted C 1-10 alkyl;
R 2 -R 5 are independently selected from C 1 -C 4 alkyl,
R 6 is selected from the group consisting aromatic groups of the following formulae:

and n is 6-15.

12. The ophthalmic solution of claim 10 wherein R 1 is selected from the group consisting of substituted and unsubstituted C 1-4 alkyl and R 2 -R 5 are methyl.

13. The ophthalmic solution of claim 10 wherein n is 6-12.

14. The ophthalmic solution of claim 10 wherein
R 1 is selected from the group consisting of substituted and unsubstituted C 1-10 alkyl;
R 2 -R 5 are independently selected from C 1 -C 4 alkyl,

R 6 is selected from the group consisting of alkylenes:

15. The ophthalmic solution of claim 10 wherein Z is selected from optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted aryl, and optionally substituted benzyl.

Assignees

• Johnson & Johnson Vision Care

Inventors

• Scales Charles
• Venkatasubban Kunisi
• Mahadevan Shivkumar
• Fadli Zohra
• Davis Carrie
• Healy Brent Matthew

Classifications

• C08G77/442 Primary

  containing vinyl polymer sequences · CPC title

• C08L51/085 Primary

  on to polysiloxanes · CPC title

• C08F226/10

  N-Vinyl-pyrrolidone · CPC title

• C08F290/068

  Polysiloxanes · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title