Silicone hydrogels having desirable water content and oxygen permeability

Patent metadata

Field	Value
Publication number	US-2016103248-A1
Application number	US-201514969292-A
Country	US
Kind code	A1
Filing date	Dec 15, 2015
Priority date	Dec 23, 2011
Publication date	Apr 14, 2016
Grant date	—

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

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 hydrophilic 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 , CCH 3 ═CH 2 , and CH═CHCH 3 ;
at least one silicone-containing component; selected from the group consisting of at least one mono (meth)acryloxyalkyl polydialkylsiloxane monomer of Formula VII or 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;
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, said reaction mixture comprising between 9 and 14% silicon and less than 15 wt % TRIS and wherein all reactive components other than said hydrophilic monomer and said silicone containing components in the reaction mixture are present in an amount between about 11 and about 92 mmol/g reactive components.

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 all ancillary components are present 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 comprise 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 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 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 , CCH 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 groups.

18 . The silicone hydrogel of claim 15 or 16 wherein all R 3 are methyl.

19 . The silicone hydrogel of claim 15 or 16 wherein R 13 is selected from the group consisting of C 1 -C 6 alkylene group which may be substituted with ether, hydroxyl and combinations thereof.

20 . The silicone hydrogel of claim 15 or 16 wherein R 13 is selected from the group consisting of C 1 or C 3 -C 6 alkylene groups which may be substituted with ether,

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

• C08F283/12

  on to polysiloxanes · CPC title

• G02B1/043 Primary

  Contact lenses · CPC title

• C08F290/06

  Polymers provided for in subclass C08G · CPC title