Water soluble silicone material

Patent metadata

Field	Value
Publication number	US-10118994-B2
Application number	US-201414765054-A
Country	US
Kind code	B2
Filing date	Jan 31, 2014
Priority date	Jan 31, 2013
Publication date	Nov 6, 2018
Grant date	Nov 6, 2018

Abstract

A water soluble silicone macromer comprising a siloxane backbone having grafted thereto a suitable number of hydrophilic groups to render the macromer water soluble, the macromer comprising a polymerizable functional group grafted to the siloxane backbone. In one aspect, the present invention provides a water soluble silicone macromer having a structure of Formula (1): where M is a hydrophilic group or segment; L is a hydrophilic or hydrophobic linkage; N is a hydrophilic or hydrophobic group or segment. Q is a polymerizable functional group; x is zero or an integer greater than zero; y is zero or an integer greater than zero; v is zero or an integer greater than zero; and z is greater than zero, with the proviso that both y and v are not zero.

First claim

What is claimed is:

1. A macromer comprising:
a siloxane backbone;
a graft attached to the siloxane backbone, the graft comprising a polymerizable functional group; and
a concentration of grafts comprising hydrophilic groups sufficient to render the macromer at least partially hydrophilic, wherein the macromer is of the Formula (1):

where M is a polymeric hydrophilic group or segment chosen from a polyvinyl alcohol (PVA), a polyamide, a polyimide, a polylactone, a homopolymer of a vinyl lactam, a copolymer of at least one vinyl lactam in the presence or in the absence of one or more vinylic comonomers, a homopolymer of acrylamide, a homopolymer of methacrylamide, a copolymer of acrylamide with one or more hydrophilic vinylic monomers, a copolymer methacrylamide with one or more hydrophilic vinylic monomers, polyethylene glycol, a poly-N--N dimethylacrylamide, a polyacrylic acid, a poly-2-ethyl oxazoline, a heparin polysaccharides, a polysaccharide, or a combination of two or more thereof; L is a hydrophilic or hydrophobic linkage; N is a hydrophilic or hydrophobic group or segment; Q is a polymerizable functional group; x is zero or an integer greater than zero; y is zero or an integer greater than zero; v is an integer greater than zero; and z is greater than zero; when the L group is a hydrophilic linkage, L can be the same as or different than the hydrophilic M group; R is independently hydrogen, a straight or branched C1-C30 alkyl group, a C1-C30 fluoroalkyl group, a C1-C20 ester-containing group, an alkyl ether, cycloalkyl ether, cycloalkenyl ether, aryl ether, arylalkyl ether, a polyether-containing group, a C1-C30 alkoxy group, a C3-C30 cycloalkyl group, a C3-C30 cycloalkylalkyl group, a C3-C30 cycloalkenyl group, a C5-C30 aryl group, a C5-C30 arylalkyl group, a C5-C30 heteroaryl group, a C3-C30 heterocyclic ring, a C4-C30 heterocyclolalkyl group, a C6-C30 heteroarylalkyl group, fluorine, a C5-C30 fluoroaryl group, or a hydroxyl group.

2. The macromer of claim 1 , wherein L is chosen from a bond, a straight or branched C1-C30 alkylene group, a C1-C30 fluoroalkylene group, a C1-C20 ester-containing group, an alkylene ether, cycloalkylene ether, cycloalkenylene ether, arylene ether, arylalkylene ether, a polyether-containing group, a C1-C30 alkenoxy group, a C3-C30 cycloalkylene group, a C3-C30 cycloalkylalkylene group, a C3-C30 cycloalkenylene group, a C5-C30 arylene group, a C5-C30 arylalkylene group, a C5-C30 heteroarylene group, a divalent C3-C30 heterocyclic ring, a C4-C30 heterocyclolalkylene group, a C6-C30 heteroarylalkylene group, a C5-C30 fluoroarylene group, a hydroxyl substituted alkylene ether, a divalent C3-C30 cationic moiety containing group; or combinations of two or more thereof.

3. The macromer of claim 1 , wherein Q is chosen from acrylate-containing radicals, methacrylate-containing radicals, acrylamide-containing radicals, methacrylamide-containing radicals, vinyl-containing radicals, allyl-containing radicals, methallyl-containing radicals, styrene-containing radicals, internal olefinic bond containing molecules, or a combination of two or more thereof.

4. The macromer of claim 3 , wherein Q is chosen from vinylcarbonate-containing radicals, vinylcarbamate-containing radicals, butenedioic acid, butenedioic esters or amides, itaconic acid, itaconic acid esters or amides, or a combination of two or more thereof.

5. The macromer of claim 1 , wherein N is chosen from a straight or branched C1-C30 alkyl group, a C1-C30 fluoroalkyl group, a C1-C20 ester-containing group, an alkyl ether, cycloalkyl ether, cycloalkenyl ether, aryl ether, arylalkyl ether, a polyether-containing group, a C1-C30 alkoxy group, a C3-C30 cycloalkyl group, a C3-C30 cycloalkylalkyl group, a C3-C30 cycloalkenyl group, a C5-C30 aryl group, a C5-C30 arylalkyl group, a C5-C30 heteroaryl group, a C3-C30 heterocyclic ring, a C4-C30 heterocyclolalkyl group, a C6-C30 heteroarylalkyl group, a C5-C30 fluoroaryl group, a hydroxyl substituted alkyl ether, a C3-C30 cationic moiety containing group; or combinations of two or more thereof.

6. The macromer of claim 1 , wherein M comprises polyethylene glycol, and Q is a methacrylate group.

7. The macromer of claim 1 , wherein z is 1 to about 200, x is 0 to about 1000, and y is 0 to about 200.

8. The macromer of claim 1 , where N and M are hydrophilic groups, optionally where N and M are the same.

9. The macromer of claim 1 , wherein the macromer is water soluble, and satisfies at least one of the following criteria:
(a) 1% of the macromer in a water solution has a transparency of 80% or greater at a wavelength between 400 to 600 nm;
(b) 10% of the macromer in a water solution has a transparency of 80% or greater at a wavelength between 400 to 600 nm;
(c) 50% of the macromer in a water solution has a transparency of 80% or greater at a wavelength between 400 to 600 nm; and/or
(d) 1% of the macromer in a water solution has a cloud point of over 30 C.

10. The macromer of claim 1 , wherein a solution of 1% by weight of the macromer in water has a turbidity of about 100 NTU or less.

11. A hydrogel forming composition comprising a macromer comprising:
a siloxane backbone;
a graft attached to the siloxane backbone, the graft comprising a polymerizable functional group; and
a concentration of grafts comprising hydrophilic groups sufficient to render the macromer at least partially hydrophilic, wherein the macromer is of the Formula (1):

where M is a polymeric hydrophilic group or segment L is a hydrophilic or hydrophobic linkage; N is a hydrophilic or hydrophobic group or segment. Q is a polymerizable functional group; x is zero or an integer greater than zero; y is zero or an integer greater than zero; v is an integer greater than zero; and z is greater than zero; when the L group is a hydrophilic linkage, L can be the same as or different than the hydrophilic M group; R is independently hydrogen, a straight or branched C1-C30 alkyl group, a C1-C30 fluoroalkyl group, a C1-C20 ester-containing group, an alkyl ether, cycloalkyl ether, cycloalkenyl ether, aryl ether, arylalkyl ether, a polyether-containing group, a C1-C30 alkoxy group, a C3-C30 cycloalkyl group, a C3-C30 cycloalkylalkyl group, a C3-C30 cycloalkenyl group, a C5-C30 aryl group, a C5-C30 arylalkyl group, a C5-C30 heteroaryl group, a C3-C30 heterocyclic ring, a C4-C30 heterocyclolalkyl group, a C6-C30 heteroarylalkyl group, fluorine, a C5-C30 fluoroaryl group, or a hydroxyl group;
wherein the composition comprises from about 0.1 to about 90 weight percent of water.

12. The hydrogel forming composition of claim 11 further comprising a co-monomer, wherein the co-monomer comprises hydroxyethyl methacrylate, N-vinyl-2-pyrrolidone, N,N-dimethylacrylamide, methacrylic acid, glycerol methacrylate, or a combination of two or more thereof.

13. The hydrogel forming composition of claim 12 , wherein the hydrogel forming composition comprises from about 0.1 weight percent to about 99.9 weight percent of the macromer.

14. A hydrogel formed from the composition of claim 11 .

15. The hydrogel of claim 14 , having a contact angle with water of from about 100° to about 5°.

16. The hydrogel of claim 14 , having a water absorption of about 10 wt. % to about 90 wt. %.

17. An article comprising the hydrogel of claim 14 .

18. The article of claim 17 , wherein the articl

Assignees

• Momentive Performance Mat Inc

Inventors

• Lang Weihong
• Liao Wen P
• Nye Susan
• Lewis Kenrick M

Classifications

• A61F2/14

  Eye parts, e.g. lenses or corneal implants; Artificial eyes · CPC title

• A61L29/06

  obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• C08L83/10

  Block- or graft-copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C08L51/08, C08L53/00) · CPC title

• C08F283/12

  on to polysiloxanes · CPC title

• A61F2/16

  Intraocular lenses · CPC title