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N I W O 2011/152886 (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date / n / i 8 December 2011 (08.12.2011) W O 2011/152886 A 2 (51) International Patent Classification: AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, A61L 9/01 (2006.01) A61K 31/23 (2006.01) CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, A61K 31/221 (2006.01) A61Q 15/00 (2006.01) DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, A61K 31/22 (2006.01) A61Q 13/00 (2006.01) HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, (21) International Application Number: ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, PCT/US201 1/022697 NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, (22) International Filing Date: SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, 27 January 201 1 (27.01 .201 1) TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (26) Publication Language: English GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, (30) Priority Data: ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, 61/35 1,435 4 June 2010 (04.06.2010) US TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, ΓΓ 12/974,7 16 2 1 December 2010 (21 .12.2010) US EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, , LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, (71) Applicant (for all designated States except US): SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, ROBERTET, INC. [US/US]; 125 Bauer Drive, Oakland, GW, ML, MR, NE, SN, TD, TG). NJ 07436 (US). Declarations under Rule 4.17 : (72) Inventors; and — as to applicant's entitlement to apply for and be granted (75) Inventors/ Applicants (for US only): DENTE, Stephen, a patent (Rule 4.1 7(H)) V. [US/US]; 125 Bauer Drive, Oakland, NJ 07436 (US). LEKA, Ketrin [US/US]; 125 Bauer Drive, Oakland, NJ — as to the applicant's entitlement to claim the priority of 07036 (US). FIELDER, Brian [US/US]; 125 Bauer the earlier application (Rule 4.17(Hi)) Drive, Oakland, NJ 07036 (US). JOHNSON, Garry [US/ Published: US]; 125 Bauer Drive, Oakland, NJ 07036 (US). — without international search report and to be republished (74) Agent: RABIN, Frederick; Fish & Richardson P.C., P.O. upon receipt of that report (Rule 48.2(g)) Box 1022, Minneapolis, MN 55440-1022 (US). (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, < 00 00 (54) Title: MALODOR NEUTRALIZING COMPOSITIONS COMPRISING UNDECYLENIC ACID OR CITRIC ACID o (57) Abstract: Compositions comprising undecylenic acid or citric acid and certain esters are effective for reducing malodors. The esters are in the molecular weight range of between 150 and 200 when the acid is undecylenic acid and in the range of between 130 and 230 when the acid is citric acid. These compositions can be used in perfumed products, household products and personal care products. MALODOR NEUTRALIZING COMPOSITIONS COMPRISING UNDECYLENIC ACID OR CITRIC ACID This invention relates to odor neutralizer compositions and their use for reducing malodors. In many applicational areas, perfumes are used for masking malodors. Annoyance caused by malodors occurs frequently in daily life and impairs personal well-being. Such malodors are, for example, those resulting from substances transpired or excreted by humans, in particular, perspiration, mouth odors, feces and urine, odors caused by animal feces or urine, in particular, those of domestic pets, kitchen odors, such as those resulting from the preparation of onions, garlic, cabbage or fish, odors due to tobacco smoke, garbage, bathrooms, molds and waste. In addition, malodors may be caused by many industrially produced basic materials used in cleansing agents, such as, for example, detergents and fabric softeners, or in body care products, such as, for example, soaps and cosmetics. The use of specific cosmetic preparations, such as, for example, hair dyes, hair-forming agents and depilatories, also produce malodors. Many rubber and plastic products also produce malodors if, due to the method of their manufacture, they still contain quantities of highly odorous, volatile active ingredients. These malodors are usually caused by particularly odorous substances which are, however, generally only present in trace amounts. Such substances include, for example, nitrogen- containing compounds such as ammonia and amines, heterocyclic compounds such as pyridines, pyrazines, indoles, etc., and sulfur-containing compounds such as hydrogen sulfide, mercaptans, sulfides, etc. The masking of malodors is a problem which is difficult to handle and solve with perfume compositions. Usually, it is only possible to mask malodors by means of a specially developed perfume oil having specific types of fragrances. Malodor counteractings are particularly advantageous when they are capable of reducing the intensity of malodors without themselves possessing any significantly intense odor or fragrance. Such active ingredients do not mask malodors; rather, they neutralize the malodors. This has the advantage that, when using such active ingredients for perfuming objects or products having malodors, perfume oils of any desired type of fragrance can be used. The consumer can, therefore, be offered a considerably broader range of fragrance types for combating malodors. In addition, active ingredients which neutralize malodors, provide the possibility of reducing the quantity of perfume oil previously required for masking odors. It is also possible to use less intensely odorous perfumes for combating malodors than those heretofore employed. Another area in which malodor reducing compositions find utility is in breath freshening compositions such as chewing gum, mints, mouthwashes, lozenges and sprays. In addition to flavoring and perfuming ingredients which mask oral malodors, it is also useful to neutralize the ingredients which cause such malodors. In recent years, a wide variety of substances have been proposed for use in neutralizing and/or suppressing malodors. These include certain acids such as undecylenic acid and a wide variety of esters, including esters of citric acid. U.S. Patent No. 6,495,097 describes the use of undecylenic acid and its lower alkyl esters as deodorants and odor neutralizers useful in a wide variety of compositions, perfumed and unperfumed. U.S. Patent No. 4,010,253 discloses the use of certain esters of citric acid or acetylcitric acid in compositions for suppressing body odor. Citric acid itself has been used in personal deodorant compositions, as indicated in U.S. Patent No. 5,098,694 and 5,662,937. Recent patent literature disclosing the use of different classes of esters as malodor neutralizers include U.S. Patents Nos. 7,157,41 1, 7,407,922 and 7,638,1 18, and Published Applications US 2010/0021413, US 2010/0028288 and US 2010/0034766. Many of the esters disclosed in the prior art are quite effective in neutralizing malodors, and undecylenic acid (and its derivatives) has also shown some effectiveness in this area. It has now been discovered that combinations of undecylenic acid or citric acid and certain esters within particular molecular weight ranges have surprisingly shown synergistic effectiveness in neutralizing malodors. This invention provides compositions comprising a combination of undecylenic acid or citric acid and one or more of certain esters within a particular molecular weight range. The molecular weight range for esters in combination with undecylenic acid is between 150 and 200. The molecular weight range for esters in combination with citric acid is between 130 and 230. These combinations exhibit a synergistic effect in neutralizing malodors. The esters within these particular molecular weight ranges which, in combination with undecylenic acid or citric acid, provide the synergistic effects are of the Formula (I) have the structure in which R i is hydrogen, phenyl substituted by hydroxy or an amino group, or a Ci-Cn alkyl group which can optionally contain 1 or 2 double bonds and which optionally can be substituted by a phenyl group, and R 2 is C1-C6 unbranched alkyl, a C 3-C12 branched alkyl group which can optionally contain 1 or 2 double bonds, or benzyl, with the proviso that (i) where Ri is a Ci-Cn alkyl or alkylene radical substituted by phenyl, such substitution occurs at the 2- or higher carbon atom, and (ii) where both Ri and R2 are unbranched alkyls, the total number of carbon atoms in said alkyls is not greater than 12 and, if said total number of carbon atoms is greater than 8, the difference between the number of carbon atoms in Ri and R2 is at least 2. The compositions of this invention can be admixed with fragrancing ingredients to yield perfumed products which also have malodor neutralizing affects. Additionally, these compositions can be incorporated into household products such as detergents and other laundry products, air fresheners and disinfectants. These compositions can also be incorporated into personal care products of all types. Undecylenic acid, citric acid and the esters of the Formula (I) are known odor neutralizers but it has now been discovered that a combination of undecylenic acid with at least one of said esters in the molecular weight range of between 150 and 200 provides a synergistic effect in odor neutralization. Likewise, it has now been discovered that compositions comprising a combination of citric acid and one or more ester of Formula (I) in the wider molecular weight range of between 130 and 230 provide a synergistic effect in odor neutralization.
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