USOO8361355B2 (12) UnitedO States Patent (10) Patent No.: US 8,361,355 B2 Li et al. (45) Date of Patent: Jan. 29, 2013 (54) PREPARATION OF ANTIMICROBIAL 4,525,563 A 6/1985 Shibata CONTACT LENSES WITH REDUCED HAZE 3. A SE: thly et al. USING SWELLINGAGENTS 4,605,712 A 8/1986 Mueller 4,661,575 A 4, 1987 Tom (75) Inventors: Yongcheng Li, St. Augustine, FL (US); 4,680,336 A 7/1987 Larsen Stephen R. Beaton, Jacksonville, FL 4,703,097 A 10/1987 Wingler (US) 4,711,943 A 12/1987 Harvey, III 4,837,289 A 6, 1989 Mueller 4,871,785 A 10, 1989 Froix (73) Assignee: Johnson & Johnson Vision Care, Inc., 4,889,664 A 12/1989 Kindt Larsen Jacksonville, FL (US) 4.954,586 A 9/1990 Toyoshima 4.954,587 A 9, 1990 Mueller (*) Notice: Subject to any disclaimer, the term of this 38: A 4. 3. Meller patent is extended or adjusted under 35 5,039,459W - I A 8, 1991 Kindtal Larsen U.S.C. 154(b) by 0 days. 5,057,578 A 10/1991 Spinelli 5,070,215 A 12/1991 Bambury (21) Appl. No.: 13/010, 117 5.314,960 A 5/1994 Spinelli 5,336,797 A 8, 1994 McGee (22) Filed:1-1. Jan. 20, 2011 3.- Iw A 23 oKoyama - - w al O O 5,371,147 A 12/1994 Spinelli (65) Prior Publication Data 5.387.632 A 2, 1995 pine US 2011/011 1120 A1 May 12, 2011 33% A. E. E. O O 5,710,302 A 1/1998 Kunzler et al. Related U.S. Application Data 5,714,557 A 2f1998 Kunzler 5,760, 100 A 6/1998 Nicolson et al. (63) Continuation of application No. 12/055,654, filed on 5,776,999 A 7/1998 Nicolson et al. Mar. 26, 2008, now abandoned. 5,789,461 A 8, 1998 Nicolson et al. 5,807,944 A 9, 1998 Hirt (60) Provisional application No. 60/909,009, filed on Mar. 5,820,918 A 10, 1998 Ronan 30, 2007. 5,849,811 A 12/1998 Nicolson et al. 5,908,906 A 6/1999 Kunzler (51) Int. Cl. 5,958,440 A 9, 1999 Burrell B29D II/00 (2006.01) 5,962.548 A 10, 1999 Vanderlaan B29C 44/08 (2006.01) 5,965,631 A 10, 1999 Nicolson 5,981,615 A 1 1/1999 Meijs (52) U.S. Cl. ......................................... 264/2.6; 264/343 5,981,675 A 1 1/1999 Valint, Jr. (58) Field of Classification Search ................... 535: (Continued) 264/343 See application file for complete search history. FOREIGN PATENT DOCUMENTS EP 406161 B1 2, 1995 (56) References Cited JP 2000-016905 1, 2000 WO WO 94.21698 A1 9, 1994 U.S. PATENT DOCUMENTS WO WO 99.27978 6, 1999 WO WOO1,24837 A1 4/2001 3: A Iggs s WO WOO3,O11351 2, 2003 3,700,761 A * 10/1972 O'Driscollet al. .......... 264/1.36 WO WOO3,O22321 3, 2003 3,808, 178 A 4/1974 Gaylord WO WO 2004/047879. A 6, 2004 4,046,706 A 9, 1977 KreZanoski et al. WO WO 2004/047879 A2 6, 2004 4,113,224. A 9, 1978 Clark WO WO 2006/O12000 A 2, 2006 4,120,570 A 10/1978 Gaylord WO WO 2006/O12000 A1 2, 2006 4,136,250 A 1, 1979 Mueller 4,139,513 A 2f1979 Tanaka OTHER PUBLICATIONS ;: A 22 U.S. Appl. No. 60/909,009, filed Mar. 30, 2007, Yongcheng. 4.182822 A is . ert U.S. Appl. No. 09/532,943, filed Mar. 22, 2000, Margiss. 4,189.546 A 2, 1980 birt Elimelech, M., Gregory J., Jia X., and Williams R., “Particle depo 4,197,266 A 4, 1980 Clark sition and aggregation, measurement, modeling and simulation' pp. 4.254.248 A 3, 1981 Friends 54-55. Butterworth Heinemann, Oxford 1995. 4,259,467 A 3/1981 Keogh 4.260,725 A 4/1981 Keogh (Continued) 4,261,875 A 4, 1981 Le Boeuf 4,276,402 A 1981 Siek Primary Examiner — Joseph Del Sole 4,327,203 A 4, 1982 Deichert 4,341,889 A 7, 1982 Deichert Assistant Examiner — Ryan Ochylski 4,343,927 A 8/1982 Chang 4,354,952. A 10/1982 Riedhammer et al. (57) ABSTRACT 4,450.2644,355,147 A 10,5, 19841982 ChoDeichert This invention relates to antimicrobial lenses containing met 4,463,149 A 7, 1984 Ellis als and methods for their production. 4.486,577 A 12/1984 Mueller 4.495.313 A 1, 1985 Larsen 15 Claims, No Drawings US 8,361,355 B2 Page 2 U.S. PATENT DOCUMENTS 2004/O150788 A1* 8, 2004 Andersson et al. ....... 351,160 R 2004/O151755 A1 8/2004 Rathore et al. ................ 424/429 5.998.498 12, 1999 Vanderlaan et al. 2005, OOO8676 A1 1/2005 Qiu et al. 6,020,445 2, 2000 Vanderlaan 2006, O100408 A1 5, 2006 Powell et al. 6,039,913 3, 2000 Hirt 2008.0102100 A1 5/2008 Rathore 6,087,415 T/2000 Vanderlaan et al. 2009,0051060 A1 2/2009 Li et al. 6,156,244 12, 2000 Muller et al. 6,486,285 11, 2002 Fujita OTHER PUBLICATIONS 6,585,768 T/2003 Hamano et al. 7,112,652 9, 2006 Ford James, T.H. “The theory of the photographic process', 4' Ed. East 7,319,133 1, 2008 Brame et al. man Kodak Company, 1977. 7,416,737 8, 2008 Alvarez-Carrigan et al. 2001 OO18464 8, 2001 Fujita ..................... 521,84.1 * cited by examiner US 8,361,355 B2 1. 2 PREPARATION OF ANTIMICROBAL As used herein, the term, “antimicrobial lens' means a lens CONTACT LENSES WITH REDUCED HAZE that exhibits one or more of the following properties, the USING SWELLINGAGENTS inhibition of the adhesion of bacteria or other microbes to the lenses, the inhibition of the growth of bacteria or other RELATED APPLICATION microbes on lenses, and the killing of bacteria or other microbes on the Surface of lenses or in an area Surrounding the This application is a continuation of U.S. patent applica lenses. For purposes of this invention, adhesion of bacteria or tion Ser. No. 12/055,654, filed Mar. 26, 2008, now abandoned other microbes to lenses, the growth of bacteria or other which is a non-provisional filing of U.S. patent application microbes on lenses and the presence of bacteria or other Ser. No. 60/909,009, which was filed on Mar. 30, 2007, now 10 microbes on the surface of lenses are collectively referred to abandoned. as “microbial colonization.” Preferably, the lenses of the invention exhibit a reduction of viable bacteria or other FIELD OF THE INVENTION microbe of at least about 0.25 log, more preferably at least about 0.5 log, most preferably at least about 1.0 log (290% This invention relates to methods of preparing antimicro 15 inhibition). Such bacteria or other microbes include but are bial lenses not limited to those organisms found in the eye, particularly Pseudomonas aeruginosa, Acanthamoeba species, Staphyllo BACKGROUND OF THE INVENTION coccus. aureus, Escherichia. Coli, Staphylococcus epidermi dis, and Serratia marce.sens. Contact lenses have been used commercially to improve As used herein the term “swelling agent” refers substances vision since the 1950s. The first contact lenses were made of that increase the size of a lens. As defined hereinafter the hard materials. They were used by a patient during waking lenses of the invention absorb water after they are cured. This hours and removed for cleaning. Current developments in the absorbance of water gives a lens that has water equilibrated field gave rise to Soft contact lenses, which may be worn dimensions (i.e. diameter, water content). These dimensions continuously, for several days or more without removal for 25 are different depending upon the composition of the lens cleaning. Although many patients favor these lenses due to formulation. Swelling agents may be used on lenses after they their increased comfort, these lenses can cause Some adverse are cured or after they have absorbed water and have reached reactions to the user. The extended use of the lenses can their water equilibrated dimensions. Such agents increase the encourage the buildup of bacteria or other microbes, particu dimensions of the lens beyond that of its water equilibrated larly, Pseudomonas aeruginosa, on the Surfaces of Soft con 30 dimensions. It is preferred that the Swelling agents of the tact lenses. The build-up of bacteria and other microbes can invention be used to treat lenses that have absorbed water to cause adverse side effects such as contact lens acute red eye their water equilibrated dimensions. Examples of swelling and the like. Although the problem of bacteria and other agents include but are not limited to extracting solvents as microbes is most often associated with the extended use of disclosed in U.S. Pat. No. 7,112,652, entitled “Solvents Use soft contact lenses, the build-up of bacteria and other 35 ful in the Preparation of Polymers Containing Hydrophilic microbes occurs for users of hard contact lens wearers as and Hydrophobic Monomers’, which is hereby incorporated well. by reference. Particularly examples of Swelling agents U.S. Pat. No. 5,820,918 discloses medical devices made include but are not limited to aqueous isopropanol, aqueous from a water absorbable polymer material with a medical propylene glycol, ethylene glycol-n-butyl ether, diethylene compound having low solubility in aqueous solutions such as 40 glycol-n-butyl ether, diethylene glycol methyl ether, ethylene an antiseptic or radiopaque compound.