(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT)

(19) World Intellectual Property Organization International Bureau

(43) International Publication Date (10) International Publication Number 22 November 2007 (22.11.2007) PCT WO 2007/132439 Al

(51) International Patent Classification: AT,AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, A61Q 15/00 (2006.01) A61K 8/49 (2006.01) CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, A61K 8/42 (2006.01) A61K 8/44 (2006.01) GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, (21) International Application Number: LY,MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, PCT/IL2006/000566 NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, (22) International Filing Date: 14 May 2006 (14.05.2006) UZ, VC, VN, YU, ZA, ZM, ZW (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every (26) Publication Language: English kind of regional protection available): ARIPO (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, (71) Applicant (for all designated States except US): HLAVIN ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), INDUSTRIES LTD. [IL/IL]; 5 Hataasiya Street, P.O. Box European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, 444, 43000 Raanana (IL). FR, GB, GR, HU, IE, IS, IT, LT, LU, LV,MC, NL, PL, PT, RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, (72) Inventor; and GN, GQ, GW, ML, MR, NE, SN, TD, TG). (75) Inventor/Applicant (for US only): HLAVIN, Philip [IL/IL]; 5 Hataasiya Street, POB 444, 4300 Raanana (IL). Published: (74) Agents: THEE, Alfred et al; Seligsohn Gabrieli & Co., — with international search report POB 1426, 61013 Tel Aviv (IL). For two-letter codes and other abbreviations, refer to the "G uid (81) Designated States (unless otherwise indicated, for every ance Notes on Codes and Abbreviations" appearing at the beg in kind of national protection available): AE, AG, AL, AM, ning of each regular issue of the PCT Gazette.

(54) Title: LONG ACTING DEODORANT COMPOSITION

(57) Abstract: A long lasting deodorant composition comprising a cosmetically acceptable base formulation containing from 0.1% to 30% of a compound selected from urea, imidazolidinyl urea or a cosmetically acceptable EDTA salt. 4 -

LONG ACTING DEODORANT COMPOSITION

FIELD OF THE INVENTION The present invention relates to compositions and in particular to deodorant formulations having long term effectiveness. BACKGROUND OF THE INVENTION There are a number of malodor forming skin bacteria, such as corynebacteria, that react with lymph gland secretions to produce body odour, and there is much prior art relating to deodorant compositions. Deodorant compositions typically are provided in a deodorant spray, as a cream or roll on dry liquid or within a waxy stick, and these are effective to a greater or lesser extent, but mostly have an effect lasting less than a number of hours, and typically no more than 24 hours and often considerably less. Many conventional deodorants are also antiperspirants and they work by blocking the sweat glands in the underarm reason where they are applied. There are some antibacterial agents that have been used in deodorant compositions. WO0024370 describes dermatologic gels for the treatment of acne vulgaris and herpes simplex containing methenamine. No reference is made to using this material in deodorants however. WO02074279A2 describes a formulation for treating body odor, in particular foot odor. The formulation comprises a combination of hexamine and zinc oxide or pharmaceutically acceptable salts thereof. The formulation is preferably an aqueous formulation, but it may be a powder formulation. Other ingredients of preferred compositions thereof include glycerol and talc. Another known antimicrobial agent is polyhexamethylene biguanide. For example, US Patent Application No.2004008295 describes a medical dressing useful in healing of wounds including polyhexamethylene biguanide as an antimicrobial agent. EPl 216691 describes an antibacterial composition comprising a synergistic mixture of a fragrance aldehyde and a preservative. One composition discussed, and having antibacterial effect includes polyaminopropyl biguanide. US 6,010,687 discloses a deodorant composition for topical application to human skin which is characterized in that it comprises an effective amount of polyhexamethylene biguanide and an effective amount of chlorhexidine in a cosmetically acceptable carrier. IL Patent Application No. 164640 by the present applicant claims a long lasting deodorant composition comprising a synergistic combination of polyaminopropyl biguanide and methenamine.

SUMMARY OF THE INVENTION It is an object of the present invention to provide a long lasting deodorant composition in a single application. Another object of the invention is to provide a long lasting deodorant composition in the form of a cream. Another object of the invention is to provide a long lasting deodorant composition in the form of a stick. Another object of the invention is to provide a long lasting deodorant composition in the form of a roll-on. Another object of the invention is to provide a long lasting deodorant composition in the form of a spray. A further object of the invention is to provide a deodorant composition that gives odor free protection for 4 to 7 days. DETAILED DESCRIPTION OF THE INVENTION It has been surprisingly found that deodorant formulations containing urea, imidazolidinyl urea, or the salts of ethylenediaminetetraacedic acid (EDTA), particularly the tetrasodiun salt, have long lasting deodorant effects especially when used together with ethylhexylglycerin and/or O-cymen-5-ol. These materials have long lasting deodorant activity even when used independently in a formulation, however, in combination they exhibit a very marked increase in long term deodorant protection. This effect is valid for people of different physiologies, including age, sex and ethnicity. Typically a single application provides a deodorant effect noticeable even up to seven days later. The effectiveness of deodorant compositions of the present invention is readily detectable by comparing the odor of an untreated armpit to a treated armpit of the same subject. Ethylhexylglycerin is known to have deodorant properties. But these are short lived, less than 24 hours. When, however, urea and/or EDTA tetrasodium salt is added to a formulation containing ethylhexylglycerin the deodorant protection is extended to between 5-7 days. In accordance with this invention there is thus provided a long lasting deodorant composition comprising a deodorant base formulation and between 0.1% and 30% of either urea, imidazolidinyl urea or EDTA salt, or any mixture of them. In a preferred composition there is included l%-8% ethylhexylglycerin. Another preferred composition includes 0.01% to 5% O-Cymen-5-ol. In a preferred formulation the deodorant composition comprises between 0.3% to 10% urea or imidazolidinyl urea and /or EDTA salt. A most preferred formulation contains 0.1% to 5% urea or imidazolidinyl urea and 0.1% to 5% EDTA salt and 0.05% to 0.5% O-Cymen-5-ol. A most preferred formulation contains 0.1% to 5% urea or imidazolidinyl urea and/or 0.1% to 5% EDTA salt The O-Cymen-5-ol can have a concentration of 0.05% to 0.5%, and preferably between 0.03% to 1%.. To the best of our knowledge there does not exist a cream deodorant composition that is effective for more than 2 to 3 days, whereas the composition of this invention may be applied to the armpit and gives a long lasting deodorant effect for up to 5 to 7 days. The relative proportions of urea, imidazolidinyl urea and EDTA salt may vary, but the antibacterial effect is already noticeable with quantities as little as 0.3% of each. In a preferred embodiment the deodorant formulation comprises about 1% urea or imidazoli dinyl urea and /or 1% tetrasodium EDTA . As stated previously, the deodorant composition can be formulated in any of the conventional form, such as a cream, a stick, a roll-on or spray. The base deodorant formulations can of course vary, and may include natural creams and oils, fragrances, humectants and powders such as Talc, starch, zinc oxide, as long as the cosmetic cream base is compatible with the active ingredients. Some of the ingredients that we found satisfactory for deodorant formulations are petrolatum, talc, Zinc oxide, potato starch, rice starch, triethyl citrate, chamomile oil, arnica oil, calendula oil, BHT, chlorphenesin, propylene glycol, sodium stearate, ethylhexylgrycerin, cremofor, panthenol, hydroxyethyl cellulose, O-Cymen-5-ol and fragrance. The following examples will best illustrate the invention. Example 1: Long lasting deodorant cream The formulation of Example 1 was tested on 10 people and gave deodorant protection of from 5-7 days whereas without the tetrasodiun EDTA, protection lasted for less than 24 hours. Example 2- Long lasting deodorant stick The formulation of Example 2 was tested on 10 people and gave deodorant protection of from 4-7 days whereas without the urea and tetrasodiun EDTA, protection lasted for less than 24 hours, and with either urea or tetrasodiun EDTA alone protection lasted 2-3 days. Example 3- Long lasting deodorant Roll-On

The formulation of Example 3 was tested on 11 people and gave deodorant protection of from 4-7 days whereas without the urea and tetrasodiun EDTA, protection lasted for less than 24 hours, and with either urea or tetrasodiun EDTA alone protection lasted 2-3 days. Example 4- Long lasting deodorant Spray The formulation of Example 4 was tested on 11 people and gave deodorant protection of from 4-7 days whereas without the urea and tetrasodiun EDTA, protection lasted for less than 24 hours, and with either urea or tetrasodiun EDTA alone protection lasted 2-3 days. Example 5: Long lasting deodorant cream

The formulation of Example 5 was tested on 10 people and gave deodorant protection of from 5-7 days whereas a control gave protection that lasted less than 24 hours. Example 6- Long lasting deodorant Sprav The formulation of Example 6 was tested on 9 people and gave deodorant protection of from 4-7 days whereas a control group had protection that lasted for less than 24 hours, and with either imidazolidinyl urea or tetrasodiun EDTA alone protection lasted 2-3 days. CLAIMS

1. A long lasting deodorant composition comprising a cosmetically acceptable base formulation containing from 0.1% to 30% of a compound selected from urea, imidazolidinyl urea or a cosmetically acceptable EDTA salt.

2 . A composition as in claim I comprising between 0.3 to 10% urea and optionally 0.3 to 10% of a cosmetically acceptable EDTA salt.

3. A composition as in claim 1, comprising between 0.3 to 10% of imidazolidinyl urea and optionally 0.3 to 10% of a cosmetically acceptable EDTA salt.

4 . A composition as in claim 1, comprising between 0.3 to 10% each of urea and imidazolidinyl urea and optionally 0.3 to 10% a cosmetically acceptable EDTA salt.

5. A composition as in claim 1, comprising between 0.1% to 5% each of urea and imidazolidinyl urea and optionally 0.1 to 5% of a cosmetically acceptable EDTA salt.

6. A composition as in any one of claims 1 to 5, wherein the EDTA salt is tetrasodium EDTA.

7. A composition as in any one of claims 1 to 6, further comprising between 1% to 8% ethylhexylglycerin.

8. A composition as in any one of claims 1 to 7, further comprising between 0.3% to 1% O-Cymen-5-ol. 9. A long lasting cream deodorant formulation comprising a composition as in any one of claims 1 to 8.

10. A long lasting stick deodorant formulation comprising a composition as in any one of claims 1 to 8.

11.A long lasting roll-on deodorant formulation comprising a composition as in any one of claims 1 to 8.

12.A long lasting spray deodorant formulation comprising a composition as in any one of claims 1 to 8.

G35417 A. CLASSIFICATION OF SUBJECT MATTER , INV. A61Q15/00 A61K8/42 A61K8/49 A61K8/44

According to International Patent Classification (IPC) or to both national classification and IPC

B. FIELDS SEARCHED Minimum documentation searched (classification system followed by classification symbols) A61K

Documentation searched other than minimum documentation to the extent that such documents are included in the fields searched

Electronic data base consulted during the international search (name of data base and, where practical, search terms used) EPO-Internal , CHEM ABS Data, PAJ, EMBASE, WPI Data

C. DOCUMENTS CONSIDERED TO BE RELEVANT

Category* Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No

US 6 468 512 Bl (CARMODY WALTER J ) 1,3,9, 11 22 October 2002 (2002-10-22) column 3 , line 24 - line 38 claim 14; examples 1,2,7

US 5 162 378 A (GUTHAUSER ET AL) 1,2 10 November 1992 (1992-11-10) column 7 , line 7 - line 10 example 2 & US 5 069 896 A (THE GILLETTE COMPANY) 1,3,9-12 3 December 1991 (1991-12-03) example 6 col umn 3 , l ine 49 - l ine 54 /

Further documents are listed in the continuation of Box C See patent family annex

* Special categories of cited documents "T" later document published after the international filing date or pnoπty date and not in conflict with the application but "A" document defining the general state of the art which is not cited to understand the principle or theory underlying the considered to be of particular relevance invention "E" earlier document but published on or after the international "X" document of particular relevance, the claimed invention filing date cannot be considered novel or cannot be considered to ■L" document which may throw doubts on prionty claιm(s) or involve an inventive step when the document is taken alone which is cited to establish the publication date of another "Y" document of particular relevance, the claimed invention citation or other special reason (as specified) cannot be considered to involve an inventive step when the "O" document referring to an oral disclosure, use, exhibition or document is combined with one or more other such docu¬ other means ments, such combination being obvious to a person skilled "P" document published prior to the international filing date but in the art later than the priority date claimed "&" document member of the same patent family

Date of the actual completion of the international search Date of mailing of the international search report

1 September 2006 05/10/2006

Name and mailing address of the ISA/ Authorized officer European Patent Office, P B 5818 Patentlaan 2 NL - 2280 HV Rijswijk TeI (+31-70) 340-2040, Tx 3 1 651 epo nl, Fax (+31-70) 340-3016 Irwin , L

Form PCT/ISA/210 (second sheet) (April 2005) C(Continuation). DOCUMENTS CONSIDERED TO BE RELEVANT

Category* Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No.

WO 02/47642 A (REVLON CONSUMER PRODUCTS) 1,2,7 20 June 2002 (2002-06-20) page 5 , line 10 - line 16 page 9 claims 9,12

US 2005/089488 A l (KIM JOO W ) 1-12 28 April 2005 (2005-04-28) paragraph [0022] examples 1-3

US 2003/152644 A l (MODAK SHANTA ET AL) 1-12 14 August 2003 (2003-08-14) paragraph [0013] - paragraph [0018]

A PATENT ABSTRACTS OF JAPAN 7,8 vol. 1999, no. 14, 22 December 1999 (1999-12-22) & JP 11 253542 A (EARTH CHEM CORP LTD), 21 September 1999 (1999-09-21) abstract

US 2001/043911 A l (HAGURA TOYOKI ET AL) 22 November 2001 (2001-11-22) table 4

A WO 02/072018 A (R. F . TECHNOLOGY CONSULTANTS, INC; RIOS, LUIS, A ; FIGUEROA, RAMON, F ) 19 September 2002 (2002-09-19) example 6

Form PCT/ISA/210 (continuation of second sheet) (April 2005) Patent document Publication Patent family Publication cited in search report date member(s) date

US 6468512 Bl 22-10-2002 NONE

us 5162378 A 10-11-1992 NONE

us 5069896 A 03-12-1991 WO 9015077 A l 13-12-1990

WO 0247642 20-06-2002 AU 3458102 A 24-06- 2002 BR 0116215 A 17-08- 2004 CA 2433177 A l 20-06- 2002 HU 0302155 A2 29-09- 2003 JP 2004515521 T 27-05- 2004 MX PA03005330 A 03-12- 2004 NO 20032508 A 03-06- 2003 NZ 526343 A 31-10- 2003

US 2005089488 A l 28-04-2005 NONE

US 2003152644 A l 14-08-2003 CA 2464468 A l 01-05-2003 MX PA04003211 A 27-07-2004 WO 03034994 A2 01-05-2003 US 2004247685 A l 09-12-2004 US 2004219227 A l 04-11-2004

JP 11253542 A 21-09-1999 JP 3749785 B2 01-03-2006

us 2001043911 A l 22-11-2001 NONE

WO 02072018 A 19-09-2002 EP 1408750 A2 21-04-2004

Form PCT/ISA/210 (patent family annex) (April 2005)