# US 2014/0155515 A1 · Silicone hydrogel composition and silicone hydrogel contact lenses made from the composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0155515 A1 - Document ID: US20140155515A1 - Status: Published application - Kind: A1 - Application number: 13/870,792 - Filed: 2013-04-25 - Published: 2014-06-05 - Earliest claimed: 2012-11-30 - Assignees: Pegavision Corporation - Applicants: Pegavision Corporation - Inventors: Yu-Chin LAI; Min-Tzung YEH; Heng-Yi LI; Wei-Jia TING - Web page: https://patentgrep.com/patent/US20140155515A1 ## CPC - G02B 1/043: {Contact lenses} - C08F 226/10: N-Vinyl-pyrrolidone - C08F 230/08: containing silicon - C08G 18/61: Polysiloxanes - C08G 18/8116: {esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group} - C08L 83/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen - C08G 77/388: containing nitrogen - G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - 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) ## Abstract A silicone hydrogel composition is disclosed. The composition includes at least one silicone macromer, a hydroxy-functionalized silicone-containing monomer, a first hydrophibic monomer and at least one crosslinker, in which the first hydrophibic monomer is N-vinyl pyrrolidone. The silicone macromer and the hydroxy-functionalized silicone-containing monomer are mutually soluble with N-vinylpyrrolidone. Silicone hydrogel contact lenses prepared from the silicone hydrogel composition are also disclosed. ## Claims ### Claim 1 A silicone hydrogel composition, comprising: at least one silicone macromer in the amount o 5 to 50 weight percentage (wt %) based on the total weight of the composition, and having the number average molecular weight (Mn) of the silicone macromer is less than 3,000; a hydroxy-functionalized silicone-containing monomer in the amount of 5 to 50 wt % based on the total weight of the composition, wherein the ratio of silicon to the hydroxyl group in the silicone-containing monomer is from 4:1 to 2:1; N-vinyl pyrrolidone in the amount of 30 to 60 wt % based on the total weight of the composition, wherein the silicone macromer, the hydroxy-functionalized silicone-containing monomer or a combination thereof are mutually soluble with N-vinylpyrrolidone; and at least one crosslinker in the amount of less than 20 wt % based on the total weight of the composition. ### Claim 2 (depends on 1) The silicone hydrogel composition of claim 1, wherein the silicone hydrogel composition is comprised in a silicone hydrogel contact lens. ### Claim 3 A silicone hydrogel composition, comprising: at least one silicone macromer in the amount of 5 to 50 wt % based on the total weight of the composition, wherein the silicone macromer has a structure of chemical formula (1): wherein X is a secondary amino group (—NH—) or an oxygen atom; Y is a secondary amino group (—NH—) or an oxygen atom; at least one of X and Y is a secondary amino group (—NH—); R1 is a hydrogen atom or a methyl group; R2 is a C1-C12 alkyl group; m is an integer from 2 to 4; n is an integer from 2 to 4; p is an integer from 0 to 4; q is an integer from 2 to 4; and k is an integer which makes the number average molecular weight (Mn) of the silicone macromer in the range of 600 to 3000; a hydroxy-functionalized silicone-containing monomer in the amount of 5 to 50 wt % based on the total weight of the composition, wherein the hydroxy-functionalized silicone-containing monomer has a structure of chemical formula (2): wherein J is a hydrogen atom or a methyl group; r is an integer from 2 to 10; K1, K2 and K3 are each a methyl group or a trimethylsiloxy (—OSi(CH3)3) in which at least one K1, K2 and K3 is a methyl group or one trimethylsiloxy (—OSi(CH3)3); a first hydrophilic monomer in the amount of 30 to 60 wt % based on the total weight of the composition, wherein the first hydrophilic monomer is N-vinyl pyrrolidone, and the silicone macromer, the hydroxy-functionalized silicone-containing monomer or a combination thereof are mutually soluble with N-vinylpyrrolidone; and at least one crosslinker in the amount of less than 20 wt % based on the total weight of the composition. ### Claim 4 (depends on 3) The silicone hydrogel composition of claim 3, wherein, when X is a secondary amino group (—NH—), Y is a secondary amino group (—NH—), m is 2, p is 0, and q is 3 in the structure of chemical formula (1), and the silicone macromer has a structure of chemical formula (3): wherein k is an integer which makes the number average molecular weight (Mn) of the silicone macromer in the range of 600 to 3000; and R2 is a C1-C10 alkyl group. ### Claim 5 (depends on 3) The silicone hydrogel composition of claim 3, wherein X is a secondary amino group (—NH—); Y is an oxygen atom; m is 2, n is 2, q is 3 in the structure of chemical formula (1); and the silicone macromer has a structure of chemical formula (4): wherein k is an integer which makes the number average molecular weight (Mn) of the silicone macromer in the range of 600 to 3000; p is an integer from 0 to 4; and R2 is a C1-C10 alkyl group. ### Claim 6 (depends on 3) The silicone hydrogel composition of claim 3, wherein the molar ratio of silicon to nitrogen of the silicone macromer is in a range from 20:1 to 5:1. ### Claim 7 (depends on 3) The silicone hydrogel composition of claim 3, wherein the molar ratio of silicon to nitrogen of the silicone macromer is in a range from 10:1 to 5:1. ### Claim 8 (depends on 3) The silicone hydrogel composition of claim 3, wherein the silicone macromer contains urethane, urea or a combination thereof. ### Claim 9 (depends on 3) The silicone hydrogel composition of claim 3, wherein the hydroxy-functionalized silicone-containing monomer has a molecular weight less than 500. ### Claim 10 (depends on 3) The silicone hydrogel composition of claim 3, wherein the molar ratio of silicon to the hydroxyl group of the hydroxy-functionalized silicone-containing monomer is in a range from 2:1 to 4:1. ### Claim 11 (depends on 3) The silicone hydrogel composition of claim 3, wherein, when J is a methyl group; r is 3; K1 is a methyl group; K2 and K3 are trimethylsiloxy in the structure of chemical formula (2); the hydroxy-functionalized silicone-containing monomer is (3-methacryloxy-2-hydroxypropoxy)propylbis(trimethylsiloxy)methylsilane; and the hydroxy-functionalized silicone-containing monomer has a structure of chemical formula (5): ### Claim 12 (depends on 3) The silicone hydrogel composition of claim 3, wherein the crosslinker is one selected from the group comprising ethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetramethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, bisphenol A di(meth)acrylate, methylenebis(meth)acrylamide, divinyl ether, divinyl sulfone, divinylbenzene, trivinylbenzene, triallyl isocyanurate, triallyl phthalate and diallyl phthalate, allyl methacrylate, and a combination thereof. ### Claim 13 (depends on 3) The silicone hydrogel composition of claim 3, further comprising at least one second hydrophilic monomer in the amount less than 20 wt % based on the total weight of the composition, wherein the second hydrophibic monomer is one selected from the group comprising 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxy-butyl methacrylate, acrylic acid, methacrylic acid, N,N-dimethylacrylamide, N,N-dimethyl methacrylamide, N-vinyl,N-methyl acetamide, 2-methacryloyloxyethyl phosphorylcholine, and a combination thereof. ### Claim 14 (depends on 3) The silicone hydrogel composition of claim 3, further comprising at least one tint monomer or one tint compound. ### Claim 15 (depends on 3) The silicone hydrogel composition of claim 3, further comprising at least one UV-blocking monomer, and the UV-blocking monomer is a benzotrizole-type monomer. ### Claim 16 (depends on 3) The silicone hydrogel composition of claim 3, further comprising at least one organic solvent, wherein the organic solvent is one selected from the group comprising n-butanol, t-butanol, n-pentyl alcohol, t-amyl alcohol, n-hexanol, n-octanol, n-nonanol, n-decanol, 3-methoxy-1-butanol, methyl cabitol, ethyl carbitol, propyl carbitol, butyl carbitol and a combination thereof. ### Claim 17 (depends on 3) The silicone hydrogel composition of claim 3, wherein the total amount of the silicone macromer and the hydroxy-functionalized silicone-containing monomer is in the range of 40 to 70 wt % based on the total weight of the composition. ### Claim 18 (depends on 3) The silicone hydrogel composition of claim 3, wherein the silicone macromer is in the amount of 10 to 30 wt % based on the total weight of the composition, the hydroxy-functionalized silicone-containing monomer is in the amount of 10 to 30 wt % based on the total weight of the composition, and the N-vinyl pyrrolidone is in the amount of 30 to 50 wt % based on the total weight of the composition. ### Claim 19 (depends on 3) The silicone hydrogel composition of claim 3, wherein the silicone hydrogel composition is comprised in a silicone hydrogel contact lens. ### Claim 20 (depends on 3) The silicone hydrogel composition of claim 3, wherein the silicone macromer is in the amount of 15 to 30 wt % based on the total weight of the composition, and k of chemical formula (1) is an integer which makes the number average molecular weight (Mn) of the silicone macromer in the range of 800 to 1500; the hydroxy-functionalized silicone-containing monomer is in the amount of 15 to 30 wt % based on the total weight of the composition, and the hydroxy-functionalized silicone-containing monomer has a structure of chemical formula (5): the first hydrophilic monomer is in the amount of 30 to 50 wt % based on the total weight of the composition; and the crosslinker is in the amount of less than 5 wt % based on the total weight of the composition.