(12) STANDARD PATENT (11) Application No. AU 2009243699 B2 (19) AUSTRALIAN PATENT OFFICE (54) Title Bleaching agent having cationic acyl pyridinium derivatives, co-bleaching activators, and hydrogen peroxide (51) International Patent Classification(s) A61K8/22 (2006.01) A61K8/86 (2006.01) A61K 8/34 (2006.01) A61Q5/08 (2006.01) A61K 8/44 (2006.01) (21) Application No: 2009243699 (22) Date of Filing: 2009.02 (87) WIPONo: WO09/135700 (30) Priority Data (31) Number (32) Date (33) Country 10 2008 022 710.2 2008.05.07 DE (43) Publication Date: 2009.11.12 (44) Accepted Journal Date: 2014.01.30 (71) Applicant(s) Henkel AG & Co. KGaA (72) Inventor(s) Gross, Wibke;Nemitz, Ralph;Pauli, Kristin;Fuhr, Denise (74) Agent / Attorney Spruson & Ferguson, L 35 St Martins Tower 31 Market St, Sydney, NSW, 2000 (56) Related Art DE19745356 (12) NACH DEM VERTRAG LIBER DIE INTERNATIONALE ZUSAMMENARBEIT AUF DEM GEBIET DES PATENTWESENS (PCT) VEROFFENTLICHTE INTERNATIONALE ANMELDUNG (19) Weltorganisation fur geistiges Eigentum Internationales Biiro (10) Internationale Veroffentlichungsnummer (43) Internationales Veroffentlichungsdatum WO 2009/135700 Al 12. November 2009 (12.11.2009) PCT (51) Internationale Patentklassiflkation: (81) Bestimmungsstaaten (soweit nicht anders angegeben, fur A61K8/22 (2006.01) A61K 8/86 (2006.01) jede verfiigbare rationale Schutzrechtsart): AE, AG, AL, A61K8/34 (2006.01) A61Q 5/08 (2006.01) AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, A61K8/44 (2006.01) BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (21) Internationales Aktenzeichen: PCT/EP2009/051835 HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, (22) Internationales Anmeldedatum: KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, 17. Februar2009 (17.02.2009) ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, (25) Einreichungssprache: Deutsch SG, SK, SL, SM, ST, SV, SY, TJ, TM, TN, TR, TT, TZ, (26) Veroffentlichungssprache: Deutsch UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Angaben zur Prioritat: (84) Bestimmungsstaaten (soweit nicht anders angegeben, fur 10 2008 022 710.2 7. Mai 2008 (07.05.2008) DE jede verfiigbare regionale Schutzrechtsart): ARIPO (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, (71) Anmelder (fur alle Bestimmungsstaaten mit Ausnahme ZM, ZW), eurasisches (AM, AZ, BY, KG, KZ, MD, RU, von US): HENKEL AG & CO. KGAA [DE/DE]; Hen- TJ, TM), europaisches (AT, BE, BG, CH, CY, CZ, DE, kelstr. 67, 40589 Diisseldorf (DE). DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, SE, SI, (72) Erflnder; und SK, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, (75) Erflnder/Anmelder (nur fur US): GROB, Wibke GW, ML, MR, NE, SN, TD, TG). [DE/DE]; Annastr. 30, 41836 Huckelhoven (DE). FUHR, Denise [DE/DE]; Wedeler LandstraBe 111, 22559 Ham­ Veroffentlicht: burg (DE). NEMITZ, Ralph [DE/DE]; Honingstr. 8, — mit internationalem Recherchenbericht (Artikel 21 Absatz 41363 Juchen (DE). PAULI, Kristin [DE/DE]; Lischke 3) Str. 16, 42119 Wuppertal (DE). (54) Title: BLEACHING AGENT HAVING CATIONIC ACYL PYRIDINIUM DERIVATIVES, CO-BLEACHING ACTIVA­ TORS, AND HYDROGEN PEROXIDE (54) Bezeichnung: AUFHELLMITTEL MET KATIONISCHEN ACYLPYRIDINIUMDERIVATEN, CO-BLEICHAKTIVATO- REN UND WASSERSTOFFPEROXID Al (57) Abstract: The object of the invention is an agent for bleaching keratinic fibers, characterized in that in a cosmetic carrier the same comprises firstly at least one cationic acyl pyridinium derivative of the formula (I), where R is a C i-CT-alkyl group, a C2-C6- alkenyl group, a C2-C6-hydroxy alkyl group, a Ci-C6-alkoxy-C2-C6-alkyl group, a carboxy-Ci-C6-alkyl group, an aryl-Ci-C6-alkyl group, a Ci-C6-dialkylammo-C2-C6-alkyl group, a heteroaryl-Ci-Ci-alkyl group, a 3-oxobutyl group, a 2-oxopropyl group, an aryl group, or a heteroaryl group, R' is a Ci-Gi-alkyl group, a C2-C6-hydroxy alkyl group, or a Ci-C6-alkoxy-C2-C6-alkyl group, X' is a physiologically compatible anion, secondly at least one toxicologically safe co-bleaching activator and/or the physiologically com­ patible salt thereof, and thirdly hydrogen peroxide. 2009/135700 (57) Zusammenfassung: Gegenstand der Erfindung ist ein Mittel zum Aufhellen von keratinischen Fasem, dadurch gekennzeich- net, dass es in emem kosmetischen [Fortsetzung auf der nachsten Seite] WO WO 2009/135700 Al lllllllllllllllllllllllllllllllllllllllllllllllllllh Trager erstens mindestens ein kationisches Acylpyridiniumderivat der Formel (I) worin R fiir eine Ci-C6-Alkylgruppe, eine C2-C6- Alkenylgruppe, eine C2-C6-Hydroxyalkylgruppe, eine Ci-C6-Alkoxy- C2-C6-alkylgruppe, eine Carboxy-Ci-Ci-alkylgruppe, eine Aryl-Ci-C6-alkylgruppe, eine Ci-C6-Dialkylamino-C2-C6-alkylgruppe, eine Heteroaryl-Ci-C6-alkylgruppe, eine 3-Oxobutylgruppe, eine 2-OxopropyIgruppe, eine Arylgruppe oder eine Heteroarylgruppe steht, R' fiir eine Ci-QAlkylgruppe, eine C2-C6-Hydroxyal- kylgruppe oder eine C1-C6- Al koxy-C2-C6-aIkyIgruppe, X' fiir ein physiologisch vertragliches Anion steht, zweitens mindestens einen toxikologisch unbedenklichen Co-Bleichaktivator und/oder dessen physiologisch vertragliches Salz und drittens Wasser- stoffperoxid enthalt. PCT/EP2009/051835 WO 2009/135700 Η 07994 PCT/US/ AU BLEACHING AGENT HAVING CATIONIC ACYL PYRIDINIUM DERIVATIVES, CO-BLEACHING ACTIVATORS, AND HYDROGEN PEROXIDE [0002] The present invention relates to agents for lightening keratin fibers, i.e. agents for use on keratin fibers, in particular human hair, containing cationic acylpyridinium derivatives, a toxicologically safe co-bleach activator and hydrogen peroxide for lightening hair and to a corresponding method. [0003] Modifying the shape and color of hair is an important area of modern cosmetics. In this way, the hair's appearance can be adapted both to current fashion trends and to a person's individual wishes. Permanent waves and other methods for modifying hair shape may be applied virtually irrespective of the type of hair to be treated. In contrast, dyeing and blonding methods are restricted to specific initial hair colors. The principles of blonding methods are known to a person skilled in the art and may be looked up in relevant monographs, for example by Kh. Schrader, Grundlagen und Rezepturen der Kosmetika, 2nd edition, 1989, Dr. Alfred HCithig Verlag, Heidelberg, or W. Limbach (ed.), Kosmetik, 2nd edition, 1995, Georg Thieme Verlag, Stuttgart, New York. [0004] In addition to dyeing, lightening of the natural hair color or blonding are what many consumers very specifically desire, since a blonde hair color is regarded as attractive and desirable from a fashion standpoint. Various blonding agents of variable blonding power are commercially obtainable for this purpose. The oxidizing agents present in these products are capable of lightening the hair fibers by oxidative destruction of the hair's own colorant melanin. To achieve a moderate blonding effect, it is sufficient to use hydrogen peroxide, optionally together with ammonia or other alkalizing agents, as the sole oxidizing agent, while if a stronger blonding effect is to be achieved, it is conventional to use a mixture of hydrogen peroxide and peroxodisulfate salts and/or peroxomonosulfate salts. Lightening is, however, also accompanied by hair damage as it is not only the natural color-imparting components of the hair H07994 PCT/US/ AU which suffer oxidative damage, but also the other structural components of the hair. Depending on its extent, the damage ranges from rough, brittle and difficult to comb hair via reduced resistance and tensile strength of the hair as far as to hair breakage. In general, the greater the quantity of hydrogen peroxide and optionally of the peroxodisulfates used, the more severe will be the damage caused to the keratin fibers. Hair dyes or lightening agents which exhibit good lightening power without simultaneously damaging the hair fibers are hitherto unknown. [0005] Before application onto human hair, hair dyes and/or lightening agents in solid or pasty form are conventionally mixed with a dilute aqueous hydrogen peroxide solution. This mixture is then applied onto the hair and rinsed back out after a specific exposure time. The duration of the exposure time on the hair in order to achieve complete decolorization or lightening is between approx. 30 and 40 minutes. Obviously, there is a requirement among users of these hair dyes or blonding agents to shorten this exposure time. [0006] Blonding processes on keratin fibers accordingly conventionally proceed at alkaline pH values, in particular between 9.0 and 10.5. These pH values are necessary to ensure that the external cuticle opens up and the active species (dye precursors and/or hydrogen peroxide) penetrate into the hair. The alkalizing agent which is conventionally used is ammonia, but this has the disadvantage for the user of an intense odor and possible irritation, which may go as far as causing skin irritation and skin sensitization. [0007] Even if the blonding agents previously on the market generally exhibit good lightening power, they cannot be regarded as optimal due to hair damage, long application times and the skin irritation possible as a result of the high concentrations of oxidizing and alkalizing agents. [0008] The use of cationic acylpyridinium derivatives in hair dyeing is known for example from documents DE 10148845 A1 or DE 10261656 A1. In both documents these derivatives are however described together with at least a second dyeing component as an agent for dyeing and thus for increasing the color intensity of the hair. It has not hitherto been apparent from the prior art 2 H07994 PCT/US/AU that these 4-acylpyridinium derivatives may be used in specific combination with specific, toxicologically safe co-bleach activators and hydrogen peroxide for bleaching the hair with very good decolorizing action.