Silicone hydrogels comprising desirable water content and oxygen permeability

Patent metadata

Field	Value
Publication number	US-9244197-B2
Application number	US-201414564667-A
Country	US
Kind code	B2
Filing date	Dec 9, 2014
Priority date	Dec 23, 2011
Publication date	Jan 26, 2016
Grant date	Jan 26, 2016

Abstract

The present invention relates to a process comprising the steps of reacting a reactive mixture comprising at least one silicone-containing component, at least one hydrophilic component, and at least one diluent to form an ophthalmic device having an advancing contact angle of less than about 80°; and contacting the ophthalmic device with an aqueous extraction solution at an elevated extraction temperature, wherein said at least one diluent has a boiling point at least about 10° higher than said extraction temperature.

First claim

What is claimed is:

1. A silicone hydrogel comprising a water content of at least about 50% and an oxygen permeability of at least about 80 barrers wherein said silicone hydrogel is formed from a reaction mixture comprising about 37 to about 75 wt % of at least one slow-reacting hydrophilic monomer having a slow-reacting hydrophilic monomer kinetic half life;
at least one silicone-containing component having a silicone-containing component kinetic half life, which may be optionally substituted with at least one hydroxyl containing group;
at least one hydroxyl-containing component selected from said silicone-containing components substituted with at least one hydroxyl group, at least one hydroxyalkyl monomer, and mixtures thereof,
wherein ratio of said slow-reacting hydrophilic component half life to said silicone-containing component half life is at least 2, said reaction mixture comprising between 9 and 14 wt % silicon from all components and less than 15 wt % TRIS and wherein all reactive components other than said slow-reacting hydrophilic monomer and said silicone containing components in the reaction mixture are ancillary components and the hydroxyl containing components are present in an amount sufficient to provide a molar ratio of hydroxyl groups in the reaction mixture to silicon atom content between about 0.16 and about 0.4.

2. The silicone hydrogel of claim 1 wherein said silicone containing components comprise less than 10 wt % TRIS.

3. The silicone hydrogel of claim 1 wherein said silicone containing components are free of TRIS.

4. The silicone hydrogel of claim 1 wherein said ancillary components in said reaction mixture in a concentration of less than 12 wt % based upon reactive components.

5. The silicone hydrogel of claim 1 wherein said water content is at least about 55%.

6. The silicone hydrogel of claim 1 wherein said water content is at least about 60%.

7. The silicone hydrogel of claim 1 , 5 or 6 wherein said oxygen permeability is at least about 90 barrers.

8. The silicone hydrogel of claim 1 , 5 or 6 wherein said oxygen permeability is at least about 100 barrers.

9. The silicone hydrogel of claim 1 wherein said ancillary components in amounts between about 38 and about 76 mmol/g reactive components.

10. The silicone hydrogel of claim 1 , 5 or 6 wherein said oxygen permeability is between about 85 and about 150 barrers.

11. The silicone hydrogel of claim 1 , 5 or 6 wherein said oxygen permeability is between about 85 and about 130 barrers.

12. The silicone hydrogel of claim 1 , 5 or 6 further comprising a modulus of less than about 150 psi.

13. The silicone hydrogel of claim 1 , 5 or 6 further comprising a contact angle of less than about 80°.

14. The silicone hydrogel of claim 1 , 5 or 6 further comprising an advancing contact angle of less than about 70°.

15. The silicone hydrogel of claim 1 wherein said at least one slow reacting monomer selected from the group consisting of N-vinylamide monomer of Formula I, vinyl pyrrolidone of Formula II-IV, N-vinyl piperidone of Formula V:

wherein R is H or methyl;
R 1 , R 2 , R 3 , R 6 , R 7 , R 10 , and R 11 are independently selected from the group consisting of H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , C(CH 3 ) 2 ;
R 4 and R 8 are independently selected from the group consisting of CH 2 , CHCH 3 and C(CH 3 );
R 5 is selected from H, methyl, ethyl; and
R 9 is selected from CH═CH 2 , C(CH 3 )═CH 2 , and CH═CHCH 3 ;
wherein said silicone-containing component is selected from the group consisting of at least one mono (meth)acryloxyalkyl polydialkylsiloxane monomer of Formula VII or the styryl polydialkylsiloxane monomer of Formula VIII:

wherein R 12 is H or methyl;

X is O or NR 16 ;
Each R 14 is independently a C 1 to C 4 alkyl which may be fluorine substituted, or phenyl;
R 15 is a C 1 to C 4 alkyl;
R 13 is a divalent alkyl group, which may further be functionalized with a group selected from the group consisting of ether groups, hydroxyl groups, carbamate groups and combinations thereof;
a is 3 to 50;
R 16 is selected from H, C1-4, which may be further substituted with one or more hydroxyl groups; and
said hydroxyalkyl monomer is selected from the group consisting of at least one hydroxyalkyl (meth)acrylate or (meth)acrylamide monomer of Formula IX or a styryl compound of Formula X

wherein R 1 is H or methyl,
X is O or NR 16 , R 16 is a H, C 1 to C 4 alkyl, which may be further substituted with at least one OH;
R 17 is selected from C 2 -C 4 mono or dihydroxy substituted alkyl, and poly(ethylene glycol) having 1-10 repeating units; wherein said at least one hydroxyalkyl (meth)acrylate or (meth)acrylamide monomer and said slow reacting monomer are present in mole percents which form a molar ratio between about 0.15 and 0.4.

16. The silicone hydrogel of claim 1 wherein said at least one slow reacting hydrophilic monomer is selected from the group consisting of N-vinylamide monomer of Formula I, vinyl pyrrolidone of Formula II or IV:

wherein R is H or methyl;
R 1 , R 2 , R 3 , R 10 , and R 11 are independently selected from the group consisting of H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , C(CH 3 ) 2 ;
R 4 is selected from the group consisting of CH 2 , CHCH 3 and C(CH 3 );
R 5 is selected from H, methyl, ethyl; and
R 9 is selected from CH═CH 2 , C(CH 3 )═CH 2 , and CH═CHCH 3 ;
(b) said at least one silicone-containing component is selected from the group consisting of at least one mono (meth)acryloxyalkyl polydialkylsiloxane monomer of Formula VII:

wherein R 12 is H or methyl;

X is O or NR 16 ;
Each R 14 is independently a C 1 to C 4 alkyl which may be fluorine substituted, or phenyl;
R 15 is a C 1 to C 4 alkyl;
R 13 is a divalent alkyl group, which may further be functionalized with a group selected from the group consisting of ether groups, hydroxyl groups, carbamate groups and combinations thereof;
a is 3 to 50;
R 16 is selected from H, C 1-4 , which may be further substituted with one or more hydroxyl groups;
(c) at least one hydroxylalkyl monomer is selected from the group consisting of hydroxyalkyl (meth)acrylate or (meth)acrylamide monomer of Formula IX

wherein R 1 is H or methyl,
X is O or NR 16 , R 16 is a H, C 1 to C 4 alkyl, which may be further substituted with at least one OH;
R 17 is selected from C 2 -C 4 mono or dihydroxy substituted alkyl, and poly(ethylene glycol) having 1-10 repeating units; wherein said at least one hydroxyalkyl (meth)acrylate or (meth)acrylamide monomer and said slow reacting monomer are present in mole percents which form a molar ratio between about 0.15 and 0.4.

17. The silicone hydrogel of claim 15 or 16 wherein each R 3 is independently selected from ethyl and methyl grou

Assignees

• Johnson & Johnson Vision Care

Inventors

• Alli Azaam
• Ford James D
• Joslin Scott L

Classifications

• C08G77/442

  containing vinyl polymer sequences · CPC title

• C08F290/068

  Polysiloxanes · CPC title

• C08F290/06

  Polymers provided for in subclass C08G · CPC title

• C08F283/12

  on to polysiloxanes · CPC title

• G02B1/043 Primary

  Contact lenses · CPC title