(12) United States Patent (10) Patent No.: US 9,301.910 B2 Yontz (45) Date of Patent: Apr

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(12) United States Patent (10) Patent No.: US 9,301.910 B2 Yontz (45) Date of Patent: Apr US0093 0191 OB2 (12) United States Patent (10) Patent No.: US 9,301.910 B2 Yontz (45) Date of Patent: Apr. 5, 2016 (54) FRAGRANT FORMULATIONS, METHODS OF C09D 7/1233 (2013.01); A61 K 2800/49 MANUFACTURE THEREOF AND ARTICLES (2013.01); C08K 5/156 (2013.01) COMPRISING THE SAME (58) Field of Classification Search None (75) Inventor: Dorie J. Yontz, Bloomington, MN (US) See application file for complete search history. (73) Assignee: GFBiochemicals Limited (MT) (56) References Cited (*) Notice: Subject to any disclaimer, the term of this U.S. PATENT DOCUMENTS patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. 1934,309 A 1 1/1933 Hoover 2,008,720 A 7/1935 Lawson (21) Appl. No.: 13/104,706 2,260,261 A 10/1941 Morey et al. 2,556,135 A 6, 1951 Croxall et al. 1-1. 2,654,723 A 10, 1953 Greene (22) Filed: May 10, 2011 2.985,536 A 5, 1961 Stein et al. O O 3,201.420 A 8, 1965 Fuzesi et al. 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A6 IK 8/92 (2006.01) 2003,0007986 A1 1/2003 Stora et al. A61O I/04 (2006.01) 2003.0036489 A1 2/2003 Liu et al. A61O I/10 (2006.01) 2003. O133895 A1 7/2003 China et al. A61O I/12 (2006.01) 2004, OO18954 A1 1/2004 Su et al. A61O3/00 (2006.01) (Continued) A61O I/02 (2006.01) A61O I/06 (2006.01) FOREIGN PATENT DOCUMENTS C09D 7/12 (2006.01) CA 1000285 11, 1976 AOIN 25/00 (2006.01) DE 3220035 A1 1, 1983 A6 IK 8/34 (2006.01) Continued A6 IK 8/35 (2006.01) (Continued) 3. g 3:08: OTHER PUBLICATIONS A6 IK 47/22 (2006.01) Oxford English Dictionary definitions of flavor, perfume and fra A61O 5/10 (2006.01) grance (2014).* A61O 9/04 (2006.01) Boehm, R., “Knowledge on cyclicketals. Part 11: Synthesis of some A61O 15/00 (2006.01) new derivatives and separation of their isomers.” Pharmazie 36(5): A61O 1704 (2006.01) Elrigl, et al., e ReactieaCO O f thee PyruvicP ic AcidC. withW. Glycerin, ss COSR 5/156 (2006.01) Annalender Chemie 476: 215-232 (Received Oct. 7, 1929)(in Ger (52) U.S. Cl. man Only). CPC ................ A61K 8/498 (2013.01): A0IN 25/00 (2013.01); A61K 8/25 (2013.01); A61K 8/29 (Continued) (2013.01); A61K 8/31 (2013.01); A61K 8/34 (2013.01); A61K 8/35 (2013.01); A61K 8/368 Primary Examiner — Tigabu Kassa (2013.01); A61K 8/4953 (2013.01); A61 K (74) Attorney, Agent, or Firm — Cantor Colburn LLP 8/4973 (2013.01); A6IK 8/922 (2013.01); A61K 8/925 (2013.01); A61K 8/927 (2013.01); (57) ABSTRACT A61K 8/97 (2013.01); A61K 47/22 (2013.01); A61O 1/02 (2013.01); A61O I/04 (2013.01); Disclosed herein is a fragrant formulation comprising a fra A61OI/06 (2013.01); A61O 1/10 (2013.01); grant composition, and an alkyl ketal ester. Disclosed herein A61O 1/12 (2013.01); A61O3/00 (2013.01); too are methods for manufacturing the fragrant formulation. 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