# US 10,118,994 B2 · Water soluble silicone material

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- Number: US 10,118,994 B2
- Document ID: US10118994B2
- Status: Granted
- Kind: B2
- Application number: 14/765,054
- Filed: 2014-01-31
- Published: 2015-12-24
- Granted: 2018-11-06
- Earliest claimed: 2013-01-31
- Assignees: Momentive Performance Materials Inc.
- Applicants: Momentive Performance Materials Inc.
- Inventors: Weihong Lang; Wen P. Liao; Susan Nye; Kenrick M. Lewis
- Web page: https://patentgrep.com/patent/US10118994B2

## CPC

- C08F 220/54: Amides {, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide}
- A61L 27/18: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 29/06: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C08F 283/12: on to polysiloxanes
- C08F 290/068: {Polysiloxanes}
- C08G 77/44: containing only polysiloxane sequences
- C08G 77/46: containing polyether sequences
- C08L 83/10: 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)
- G02B 1/043: {Contact lenses}
- A61B 2017/00942: {hydrophilic}
- A61F 2/14: Eye parts, e.g. lenses or corneal implants; Artificial eyes
- A61F 2/16: Intraocular lenses
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- A61B: DIAGNOSIS; SURGERY; IDENTIFICATION (usefulness limited to only animals A61D)
- A61F: FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS (dental prosthetics A61C)

## 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.

## Claims

### Claim 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.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

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.

### Claim 4 (depends on 3)

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.

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 1)

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.

### Claim 8 (depends on 1)

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

### Claim 9 (depends on 1)

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.

### Claim 10 (depends on 1)

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.

### Claim 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.

### Claim 12 (depends on 11)

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.

### Claim 13 (depends on 12)

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.

### Claim 14 (depends on 11)

A hydrogel formed from the composition of claim 11.

### Claim 15 (depends on 14)

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

### Claim 16 (depends on 14)

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

### Claim 17 (depends on 14)

An article comprising the hydrogel of claim 14.

### Claim 18 (depends on 17)

The article of claim 17, wherein the article is chosen from a heart valve, a film, a surgical device, a vessel substitute, a intrauterine device, a membrane, a diaphragm, a surgical implant, a blood vessel, and artificial ureter, artificial breast tissue, a membranes for kidney dialysis, or membrane for a heart/lung machine, a catheter, a mouth guard, a denture liner, an ophthalmic device, or a contact lens.

### Claim 19 (depends on 1)

An article comprising an internal wetting agent or a wettable crosslinker, the internal wetting agent and/or wettable crosslinker comprising the macromer of claim 1.

### Claim 20 (depends on 1)

The macromer of claim 1, wherein M is polyethylene glycol, Q comprises a methacrylate group, L is polyethylene glycol, N is polyethylene glycol, R comprises a lower alkyl having up to 8 carbon atoms, z is 1 to about 200, x is 0 to about 1000, v is 2 to about 200, and y is 0 to about 200.