USOO8835369B2 (12) United States Patent (10) Patent No.: US 8,835,369 B2 Cifeli (45) Date of Patent: Sep. 16, 2014 (54) ODORLESSACETONE-FREE NAIL POLISH 2008/0207933 A1* 8/2008 Bigorra Llosas et al. ....... 554/52 REMOVING COMPOSITION 2008/0241089 A1 * 10, 2008 Banowski et al. .............. 424,65 2009 OO68255 A1* 3, 2009 Yu et al. ......... ... 424/450 O - O 2009/0162446 A1* 6/2009 Gatto et al. ................... 424/489 (75) Inventor: Dana Cifeli, Clark, NJ (US) 2009,0191138 A1 7, 2009 Dechow 2010/0204076 A1 8/2010 Cheng (73) Assignee: L'Oreal, Paris (FR) - FOREIGN PATENT DOCUMENTS (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 CN 101112351 A 1, 2008 U.S.C. 154(b) by 134 days. CN 101953.769. A 1, 2011 DE 202009000908 U1 6, 2009 (21) Appl. No.: 13/487,639 JP 2006182674 A T 2006 OTHER PUBLICATIONS (22) Filed: Jun. 4, 2012 English Abstract of CN-10 1953769-A. (65) Prior Publication Data English Abstract of CN-101112351-A. English Abstract of JP-2006182674-A. US 2013/0319462 A1 Dec. 5, 2013 Notification of Transmittal of the International Search Report and the Written Opinion of the International Searching Authority, or the (51) Int. Cl. Declaration, International Application No. PCT/US2013/042406, CID 3/43 (2006.01) mailed Nov. 12, 2013, including International Search Report and CI ID3/20 (2006.01) Written Opinion of the ISA. (52) U.S. Cl. CPC ................ CIID3/43 (2013.01); C1 1D3/2093 * cited by examiner (2013.01) USPC ........................................... 510/118, 5.10/407 Primary Examiner — Gregory Webb (58) Field of Classification Search (74) Attorney, Agent, or Firm — Novak Druce Connolly CPC .............................. C11D 3/433; C11D 3/2093 Bove + Quigg LLP USPC .................................................. 510/118, 407 See application file for complete search history. (57) ABSTRACT One aspect of the present invention comprises a nail polish (56) References Cited removing composition that is essentially free of acetone and ethyl acetate, and is essentially free of odor. The composition U.S. PATENT DOCUMENTS includes at least one triester of glycerol and C-Cs carboxylic 3,384,592 A 5, 1968 Weems acid, at least one C-Cs glycol, at least one C-C cyclic 5,258,070 A 11/1993 Monteleone et al. carbonate, and, optionally, at least one colorant. Another 5,346,692 A 9, 1994 Wohlrab et al. aspect of the present invention is a method of removing nail 5,827,807 A 10, 1998 Aoshima et al. polish, comprising providing the nail polish removing com 6,585,963 B1 7/2003 Quan et al. 6,936,264 B2 * 8/2005 Glenn et al. .................. 424/401 position; immersing an absorbent material in the composi 6,998.371 B2 2/2006 Tavares tion, wherein the absorbent material absorbs the composition; 7,074,746 B2 7/2006 Fujii contacting the absorbent material to nail polish for a time 8,138,106 B2 * 3/2012 Hamed et al. ................. 442/123 Sufficient to plasticize the nail polish film; and removing the 8,262,634 B1* 9/2012 Gray et al. ........... 604,385.05 plasticized nail polish film by mechanically rubbing with the 2002/0159960 A1* 10, 2002 Scancarella et al. ............ 424,64 2004/0022822 A1 2/2004 Poret .................... ... 424/401 absorbent material, wherein the composition comprises one 2004/0033254 A1* 2/2004 Song et al. .................... 424/449 or more phases. 2004/O198630 A1* 10, 2004 Schmid et al. ................ 510,499 2007/0287647 A1 12/2007 Hadry et al. 19 Claims, No Drawings US 8,835,369 B2 1. 2 ODORLESSACETONE-FREE NAL POLISH may comprise at least one triester of glycerol and C-Cs REMOVING COMPOSITION carboxylic acid in a range from about 5% to about 50% by weight, based on the total weight of the composition. BACKGROUND OF THE INVENTION According to one embodiment, the at least one C-C gly col is selected from the group consisting of 1,2-propylene Organic Solvents, such as acetone and ethyl acetate, are glycol, 1.2-butylene glycol and 1.2-pentylene glycol. typically used to remove nail polish. While such organic According to a further embodiment, the at least one C-Cs Solvents are generally effective in removing most types of nail glycol is propylene glycol. The composition of the present polish, consumers do not consider them desirable because, invention may comprise the at least one C-C glycol in a inter alia, the organic solvents have a strong odor and are 10 range from about 10% to about 30% by weight, based on the harsh on the nail and skin near the nail. total weight of the composition. Acetone, for example, is an organic Solvent capable of According to one embodiment, the at least one C-C, dissolving nail polish effectively, and is a well-known com cyclic carbonate is selected from the group consisting of ponent of nail polish removers. However, acetone can also propylene carbonate, butylene carbonate and pentylene car remove moisture, and thus the nail and the skin near the nail 15 bonate. In a further embodiment, the at least one C-C cyclic may appear white and dry after contact with acetone-based carbonate is propylene carbonate. The composition of the removers. Furthermore, acetone has a distinct odor that some present invention may comprise the at least one C-C cyclic users find objectionable; and nail polish removers having carbonate in a range from about 50% to about 75% by weight, acetone at 60% to 70% are flammable. based on the total weight of the composition. Another example of an organic solvent that can also be, and In one embodiment, the at least one triester of glycerol and commonly is, used in nail polish removers is ethyl acetate. C-C carboxylic acid ranges from about 5% to about 50% by While ethyl acetate is not as strong of a solvent as acetone, it weight, the at least one C-Cs glycol ranges from about 10% remains effective in removing nail polish, and thus is com to about 30% by weight, the at least one C-C cyclic carbon monly regarded as an alternative to acetone. Ethyl acetate is ate ranges from about 50% to about 75% by weight, and the at also slightly less harsh to the nail and skin near the nail in 25 least one colorant optionally ranges from 0.01% to about 2% comparison with acetone. Furthermore, ethyl acetate is less by weight, wherein the weight percentages are based on the Volatile than acetone, but its odor is still significant and gen total weight of the composition. erally objectionable. In another embodiment, the at least one triester of glycerol Further non-acetone nail polish removers may contain Sol and C-C carboxylic acid comprises triacetin, the at least one vents such as methyl acetate, methyl alcohol, ethyl alcohol, 30 C-C glycol comprises propylene glycol, and the at least one methyl diglycol, and butyl diglycol. These solvents have C-C cyclic carbonate comprises propylene carbonate. reduced odors but may cause skin irritation on prolonged use. According to one embodiment of the present invention, Also, Some solvents, such as methyl alcohol, are considered triacetin ranges from 5% to about 50% by weight, propylene hazardous to health. glycol ranges from about 10% to about 30% by weight, and Nail polish remover compositions that do not utilize 35 propylene carbonate ranges from about 50% to about 75% by acetone have been attempted. For example, a nail polish weight, wherein the weight percentages are based on the total remover according to U.S. Pat. No. 6,998.371 describes the weight of the composition. use of esters of fatty acids having 16 to 18 carbon atoms, In an embodiment of the present invention, the composi lower alkyl lactate and a naturally occurring wax. However, tion further comprises at least one ester of a C-C alcohol and while the composition according to the 371 patent is acetone 40 myristic acid. The at least one ester of the C-C alcohol and free, it generally leaves an oily feel on the nail and leaves the myristic acid can be a member selected from the group con nail looking unsightly. Another example is a nail polish sisting of methyl myristate, ethyl myristate, n-propyl remover according to U.S. Patent Application Publication myristate, isopropyl myristate, n-butyl myristate, isobutyl No. 2007/0287647 that describes the use of isobutyl nitrite myristate and tert-butyl myristate. According to an embodi and butylated linseed oil as active ingredients for nail polish 45 ment, the at least one ester of the C-C alcohol and myristic removal. However, while the 647 Publication does not use acid is isopropyl myristate. acetone or ethyl acetate, the main ingredient is isobutyl According to an embodiment, the ratio of propylene glycol nitrite, which is a known inhalant recreational drug. to isopropyl myristate by weight ranges from about 9:1 to Therefore, there remains a need for a nail polish removing about 1:9. composition that is essentially odorless and is essentially free 50 According to an embodiment of the composition, the at of acetone and ethyl acetate. least one triester of glycerol and C-Cs carboxylic acid ranges from about 5% to about 50% by weight, the at least one C-Cs BRIEF SUMMARY OF THE INVENTION glycol ranges from about 10% to about 30% by weight, the at least one C-C cyclic carbonate ranges from about 50% to One aspect of the present invention is a nail polish remov 55 about 75% by weight, the at least one colorant ranges from ing composition that includes at least one triester of glycerol 0.01% to about 2% by weight, and the at least one ester of the and a C-C carboxylic acid, at least one C-Cs glycol, at least C-C alcohol and myristic acid ranges from about 15% to one C-C cyclic carbonate, and optionally at least one colo about 45% by weight, wherein the weight percentages are rant, wherein the composition is essentially free of acetone based on the total weight of the composition.