Hydrophilic silicone monomers, process for their preparation and thin films containing the same
View Patent ↗There is provided a mono-(meth)acrylate functionalized hydrophilic silicone monomers containing a polyether with branched linking group, useful in making water absorbing silicone-hydrogel films for contact lens applications. This invention also provides homo-polymers and copolymers made from the mono-(meth)acrylate functionalized hydrophilic silicone monomers described herein. Also provided is a process for producing the monomers and polymers described herein and contact lenses produced from the same.
1. A mono-functional silicone-containing monomer having the general formula:
wherein
a is 1 to about 50;
b is 0 to about 100;
each R is independently selected from the group consisting of monovalent aliphatic, cycloaliphatic or aromatic hydrocarbon groups of 1 to about 10 carbons and halogenated hydrocarbon groups of 1 to about 10 carbons;
Z is a polyether having the general formula:
—H 2 C—CH(R b )—(CH 2 ) n —O—(C 2 H 4 O) p —(C 3 H 6 O) q —(C 4 H 8 O) r —X
wherein
n is 1 to about 20;
p and q individually are 0 to about 100;
R b is an alkyl group having from 1 to about 4 carbon atoms;
r is 0 to about 50 and the sum of p+q+r is greater than 0; and
X is a polyether-capping group having the general formula:
wherein R 3 and R 4 independently are either hydrogen or a substituted or unsubstituted saturated monovalent hydrocarbon group of 1 to about 20 carbons.
2. The monomer of claim 1 wherein at least one R comprises a fluorinated hydrocarbon or trialkylsilyloxy group.
3. The monomer of claim 1 wherein each R independently comprises a saturated monovalent hydrocarbon group of from 1 to 6 carbon atoms or a phenyl group.
4. The monomer of claim 1 wherein a+b is 1 to about 20 for formula (I) and 3 to about 20 for formula (II).
5. The monomer of claim 1 wherein the monomer comprises a cyclic monomer.
6. The monomer of claim 1 wherein the silicone monomer has the following formula:
wherein b is 0 to about 100, and p is 1 to about 50.
7. The monomer of claim 6 wherein b is from 0 to 2 and/or p is from 2 to about 15.
8. The monomer of claim 1 wherein b is equal to 0 and the total number of carbon atoms present in Z is at least 6.
9. The monomer of claim 1 , wherein n is from 1 to 3 and Rb is a methyl group.
10. A polymer comprising the reaction product of at least one monomer of claim 1 .
11. A copolymer comprising the reaction product of at least 2 monomers of claim 1 wherein at least one of said monomers has a different structure than the at least one other monomer.
12. A copolymer comprising the reaction product of at least 1 monomer of claim 1 and at least 1 additional monomer selected from the group consisting of vinylic monomers, acrylamide monomers and acrylic monomers.
13. The copolymer of claim 12 wherein the vinylic monomer is N-vinyl-pyrolidone.
14. The copolymer of claim 12 wherein the acrylic monomer is 2-hydroxy-ethyl-methacrylate (HEMA).
15. The copolymer of claim 12 wherein the acrylamide monomer is N,N-dimethylacrylamide (DMA).
16. The copolymer of claim 12 wherein the additional monomer is a multifunctional crosslinker.
17. The copolymer of claim 12 wherein the ratio of said monomer of claim 1 to said at least one additional monomer is from 1:100 to about 100:1.