Silicone hydrogels comprising polyamides

Patent metadata

Field	Value
Publication number	US-11828913-B2
Application number	US-202016952573-A
Country	US
Kind code	B2
Filing date	Nov 19, 2020
Priority date	Jul 6, 2016
Publication date	Nov 28, 2023
Grant date	Nov 28, 2023

Abstract

Described are silicone hydrogels that are more biocompatible than current ocular materials. The silicone hydrogels are formed from a reactive monomer mixture comprising: a mixture of hydroxyl substituted silicone containing components, at least one polyamide; and at least one hydrophilic monomer. The silicone hydrogels also display a desirable balance of properties, including clarity, oxygen permeability, wettability and desirable protein uptake.

First claim

What is claimed is:

1. A silicone hydrogel formed from a reactive monomer mixture comprising:
a) between about 1 and about 15 wt % at least one polyamide;
b) at least one first mono-functional hydroxyl substituted, poly(disubstituted siloxane) having 4 to 8 siloxane repeating units;
c) at least one second hydroxyl substituted poly(disubstituted siloxane) comprising a multifunctional hydroxyl substituted poly(disubstituted siloxane) having 10 to 200 siloxane repeating units;
d) about 5 to about 35 wt % of at least one hydrophilic monomer;
wherein the first mono-functional hydroxyl substituted, poly(disubstituted siloxane) and the second hydroxyl substituted poly(disubstituted siloxane) are present in concentrations to provide a ratio of wt % of all first mono-functional hydroxyl substituted, poly(disubstituted siloxane) to wt % of all second hydroxyl substituted poly(disubstituted siloxane) of 0.4-1.3,

wherein the polyamide consists essentially of one or more acyclic polyamides.

2. The silicone hydrogel of claim 1 , wherein the first monofunctional hydroxyl substituted, poly(disubstituted siloxane) comprises compounds of Formula VII-1

wherein
Z is selected from O, N, S or NCH 2 CH 2 O, wherein when Z is O or S then R 2 is not present;
R 1 is independently H or methyl;
R 2 is H or is a linear, branched, or cyclic alkyl group containing one to eight carbon atoms, any of which may be further substituted with at least one hydroxy group, amide, ether, and combinations thereof;
R 3 and R 4 are independently a linear, branched, or cyclic alkyl group containing one to eight carbon atoms, any of which may be further substituted with at least one hydroxy group, amide, ether, and combinations thereof; or R 3 and R 4 are independently phenyl;
n is 4-8; and
R 5 is selected from straight or branched C 1 to C 8 alkyl groups, which may be optionally substituted with one or more hydroxyl, amide, ether, and combinations thereof.

3. The silicone hydrogel of claim 1 , wherein the multifunctional hydroxyl-substituted poly(disubstituted siloxane) comprises a di-functional hydroxyl-substituted poly(disubstituted siloxane) of Formula XI

wherein
wherein R 1 is independently a hydrogen atom or methyl group;
R 2 and R 3 are independently a linear, branched, or cyclic alkyl group containing one to eight carbon atoms, any of which may be further substituted with at least one hydroxy group, amido, ether, amino, carboxyl, carbonyl groups and combinations thereof; or are selected from —(CH 2 CH 2 O) x OCH 3 where x is from 1 to 20; and
n is from 1 to 200.

4. The silicone hydrogel of claim 1 , wherein the first mono-functional hydroxyl-substituted poly(disubstituted siloxane) and the second hydroxyl-substituted poly(disubstituted siloxane) are present in the reactive monomer mixture in a total concentration between about 40 and about 70 wt %.

5. The silicone hydrogel of claim 1 , wherein the first monofunctional hydroxyl substituted, poly(disubstituted siloxane) comprises a monofunctional hydroxyl substituted, poly(dimethylsiloxane) of any of Formulae VIIa-IXb:

wherein R 1 is methyl or H; n is between 4 and 30; wherein Z is selected from O, N, S or NCH 2 CH 2 O, when Z is O or S R 2 is not present;
R 2 is independently selected from the group consisting of a linear, branched, or cyclic alkyl group containing one to eight carbon atoms, any of which may be further substituted with at least one hydroxy group, and which may be optionally substituted with amide, ether, and combinations thereof;
R 3 and R 4 are independently a linear, branched, or cyclic alkyl group containing one to eight carbon atoms, any of which may be further substituted with at least one hydroxy group, amide, ether, and combinations thereof; or R 3 and R 4 are independently phenyl;
n 1 and n 2 are independently between 4 to 100;
n 3 is 1-50;
R 5 is selected from straight or branched C 1 to C8 alkyl groups, which may be optionally substituted with one or more hydroxyl, amide, ether, polyhydroxyl groups selected from straight or branched C 1 to C8 groups having a formula of C f H g (OH) h wherein f=1-8 and g+h=2f+1 and cyclic C 1 to C 8 groups having a formula of C f H g (OH) h wherein f=1-8 and g+h=2f−1, and combinations thereof;
a is 4-8.

6. The silicone hydrogel of claim 1 , wherein the hydrophilic monomer comprises a reactive group selected from the group consisting of (meth)acrylates, (meth)acrylamides, styrenes, N-vinyllactams, N-vinylamides, O-vinylcarbamates, O-vinylcarbonates, vinyl ethers, vinyl esters, vinyls, allyls and combinations thereof.

7. The silicone hydrogel of claim 1 further comprising at least one charged monomer.

8. The silicone hydrogel of claim 1 , wherein the hydrophilic monomer is present in the reactive monomer mixture in an amount between about 15 to about 35 wt %.

9. The silicone hydrogel of claim 1 , wherein the multifunctional hydroxyl substituted, poly(disubstituted siloxane) comprises at least one compound of Formula XII:

wherein R 1 is independently a hydrogen atom or methyl group; Z is selected from O, N, S or NCH 2 CH 2 O, wherein for Z═O and S, R 2 is not required;
R 2 is selected from the group consisting of H or a linear, branched, or cyclic alkyl group containing one to eight carbon atoms, any of which may be further substituted with at least one hydroxy group, amido, ether, amino, carboxyl, carbonyl groups and combinations thereof; a linear or branched alkyleneoxy group, optionally substituted with one or more hydroxyl, amino, amido, ether, carbonyl, carboxyl, and combinations thereof; a C 1 -C 6 linear or branched fluoroalkyl groups optionally substituted with one or more hydroxyl, amino, amido, ether, carbonyl, carboxyl, and combinations thereof; a substituted or un-substituted aryl groups, wherein the substituents are selected from halogen, hydroxyl, alkoxy, alkylcarbonyl, carboxy, and linear or branched or cyclic alkyl groups which may be further substituted with halogen, hydroxyl, alkoxy, alkylcarbonyl, and carboxyl groups, and combinations thereof;
n 1 and n 2 are independently selected from 4 to 100; and
n 3 is 1-50.

10. The silicone hydrogel of claim 1 , wherein the hydrophilic monomer is selected from hydrophilic amide monomers.

11. The silicone hydrogel of claim 10 , wherein the reactive monomer mixture comprises less than about 30 wt % hydrophilic amide monomers.

12. The silicone hydrogel of claim 1 , wherein the hydrophilic monomer is selected from the group consisting of N,N-dimethylacrylamide, acrylamide, ethylene glycol vinyl ether (EGVE), di(ethylene glycol) vinyl ether (DEGVE), N-vinyl pyrrolidone (NVP), 1-methyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone; 1-ethyl-5-methylene-2-pyrrolidone, N-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, 1-n-propyl-3-methylene-2-pyrrolidone, 1-n-propyl-5-methylene-2-pyrrolidone, 1-isopropyl-3-methylene-2-pyrrolidone, 1-isopropyl-5-methylene-2-pyrrolidone, N-vinyl-N-methyl acetamide (VMA), N-vinyl-N-ethyl acetamid

Assignees

• Johnson & Johnson Vision Care

Inventors

• Alli Azaam
• Guzman Alexander

Classifications

• G02B1/043 Primary

  Contact lenses · CPC title

• C08F271/00

  Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00 · CPC title

• C08F271/02

  on to polymers of monomers containing heterocyclic nitrogen · CPC title

• C08F290/068 Primary

  Polysiloxanes · CPC title

• C08G77/442

  containing vinyl polymer sequences · CPC title