# US 9,039,174 B2 · Ethylenically unsaturated polymerizable groups comprising polycarbosiloxane monomers > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,039,174 B2 - Document ID: US9039174B2 - Status: Granted - Kind: B2 - Application number: 13/841,145 - Filed: 2013-03-15 - Published: 2013-10-31 - Granted: 2015-05-26 - Earliest claimed: 2009-07-09 - Assignees: Bausch & Lomb Incorporated - Applicants: Bausch & Lomb Incorporated - Inventors: Alok Kumar Awasthi; Jay F. Kunzler - Web page: https://patentgrep.com/patent/US9039174B2 ## CPC - C08F 30/08: containing silicon - C07F 7/0838: {Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21)} - C08G 77/50: by carbon linkages - C08G 77/20: containing silicon bound to unsaturated aliphatic groups - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS ## Abstract The present application relates to novel monomers comprising polycarbosiloxane monomers useful in certain specific embodiments in the manufacture of devices. More particularly, the present application relates to certain ethylenically unsaturated free radical polymerizable monomers comprising polycarbosiloxane monomers. Even more particularly, the present application pertains to monomers comprising polycarbosiloxane monomers which further comprise at least two ethylenically unsaturated free radical polymerizable groups. ## Claims ### Claim 1 An article of manufacture selected from the group consisting of contact lenses, phakic and aphakic intraocular lenses and corneal implants; wherein the article is formed from polymerizing a monomer mixture including an ethylenically unsaturated free radical polymerizable polycarbosiloxane monomer of formula (I) and at least a second free radical copolymerizable monomer, wherein the polycarbosiloxane monomer of formula (I) is present at from about 0.1 to about 30 percent by weight of the monomer mixture: wherein R1, R2, R4, R5, R6, R7, R8, R11, R12, R13, R14, R15 and R16 are each independently a monovalent atom or group selected from H, alkyl, halo alkyl, heteroalkyl, cyclo alkyl, heterocyclo alkyl, alkenyl, halo alkenyl, or aromatic; wherein R3 is a monovalent atom or group selected from H, alkyl, halo alkyl, heteroalkyl, cyclo alkyl, heterocyclo alkyl, alkenyl, halo alkenyl, aromatic or methacryloxypropyl; wherein at least one of R9 or R10 is hydrogen, and the other of R9 and R10 may not be present when monomers of formula (I) comprise -[silyl-alkenyl-siloxy]- units, and when present in a monomer comprising -[silyl-alkyl-siloxy]- units is independently a monovalent atom or group selected from H, alkyl, alkene, alkyne; y is 2-7; n is 1-100; n1 is greater than zero and up to 10; L is the same or different and is a divalent linker group or a bond; and V is an ethylenically unsaturated free radical polymerizable monovalent group. ### Claim 2 (depends on 1) An article of manufacture of claim 1, wherein y is 2. ### Claim 3 (depends on 2) An article of manufacture of claim 2, wherein n is 2-80. ### Claim 4 (depends on 2) An article of manufacture of claim 2, wherein n is 3-20. ### Claim 5 (depends on 2) An article of manufacture of claim 2, wherein n is 5-15. ### Claim 6 (depends on 1) The article of manufacture of claim 1 wherein the article is a contact lens. ### Claim 7 (depends on 6) The article of manufacture of claim 6 wherein the article is a hydrogel contact lens. ### Claim 8 (depends on 1) The article of manufacture of claim 1 and the monomer mixture comprises at least second and third copolymerizable monomers. ### Claim 9 (depends on 8) The article of manufacture of claim 8, wherein the monomer mixture comprises from 0.1 to 75.8 percent by weight of a second copolymerizable silicone comprising hydrophobic monomer, 0 to 60 percent by weight of non-silicone comprising hydrophobic monomers, and 0.1 to 75.8 percent by weight of hydrophilic monomers. ### Claim 10 (depends on 9) The article of manufacture of claim 9 wherein the monomer mixture comprises a bulky monomer selected from the group consisting of methacryloxypropyl tris(trimethylsiloxy)silane (“TRIS”), pentamethyldisiloxy methylmethacrylate, tris(trimethylsiloxy) methacryloxy propylsilane, phenyltretramethyl-disloxanylethyl acrylate, methyldi(trimethylsiloxy) methacryloxymethyl silane, 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate, 3-[tris(trimethylsiloxy)silyl]propyol allyl carbamate, and 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate and mixtures thereof. ### Claim 11 (depends on 10) The article of manufacture of claim 10 wherein the bulky monomer is present at about 25 to about 41 percent by weight of the monomer mixture. ### Claim 12 (depends on 1) An article of manufacture of claim 1, wherein the polycarbosiloxane monomer is of formula (III), (XXVI), (XXVII), (XXVIII), (XXIX), (XXX), (XXXIV), or (XXXV): wherein n2 is 0 to 10. ### Claim 13 (depends on 1) An article of manufacture of claim 1, wherein the polycarbosiloxane monomer is of formula (III): ### Claim 14 (depends on 1) An article of manufacture of claim 1, wherein the polycarbosiloxane monomer is of formula (XXVI), (XXVII), or (XXVIII): wherein n2 is 0 to 10. ### Claim 15 (depends on 1) An article of manufacture of claim 1, wherein the polycarbosiloxane monomer is of formula (XXIX) or (XXX): ### Claim 16 (depends on 1) An article of manufacture of claim 1, wherein the polycarbosiloxane monomer is of formula (XXXIV) or (XXXV): wherein n2 is 0 to 10. ### Claim 17 (depends on 1) An article of manufacture of claim 1, wherein the polycarbosiloxane monomer is of formula (IX): ### Claim 18 (depends on 1) An article of manufacture of claim 1, wherein n is 2-80. ### Claim 19 (depends on 1) An article of manufacture of claim 1, wherein n is 3-20. ### Claim 20 (depends on 1) An article of manufacture of claim 1, wherein n is 5-15.