CA2486905A1 - Cosmetic compositions containing salts of malonic acid - Google Patents
Cosmetic compositions containing salts of malonic acid Download PDFInfo
- Publication number
- CA2486905A1 CA2486905A1 CA002486905A CA2486905A CA2486905A1 CA 2486905 A1 CA2486905 A1 CA 2486905A1 CA 002486905 A CA002486905 A CA 002486905A CA 2486905 A CA2486905 A CA 2486905A CA 2486905 A1 CA2486905 A1 CA 2486905A1
- Authority
- CA
- Canada
- Prior art keywords
- weight
- malonic acid
- salt
- cosmetic composition
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 58
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000002537 cosmetic Substances 0.000 title claims abstract description 25
- 150000003839 salts Chemical class 0.000 title claims abstract description 20
- 239000002253 acid Substances 0.000 claims description 13
- 230000032683 aging Effects 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 4
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 claims description 4
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims description 4
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 3
- BDOVYCYVRDSMCL-UHFFFAOYSA-N azane;2-(hydroxymethyl)propane-1,3-diol Chemical compound N.OCC(CO)CO BDOVYCYVRDSMCL-UHFFFAOYSA-N 0.000 claims description 3
- 229960002887 deanol Drugs 0.000 claims description 3
- 239000012972 dimethylethanolamine Substances 0.000 claims description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 3
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 2
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 2
- 239000004471 Glycine Substances 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- 235000004279 alanine Nutrition 0.000 claims description 2
- 235000001014 amino acid Nutrition 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
- JEPPYVOSGKWVSJ-UHFFFAOYSA-N bicyclo[2.2.1]heptan-3-amine Chemical compound C1CC2C(N)CC1C2 JEPPYVOSGKWVSJ-UHFFFAOYSA-N 0.000 claims description 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims description 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 2
- WSTNFGAKGUERTC-UHFFFAOYSA-N n-ethylhexan-1-amine Chemical compound CCCCCCNCC WSTNFGAKGUERTC-UHFFFAOYSA-N 0.000 claims description 2
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 claims description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 2
- 229940100684 pentylamine Drugs 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000011149 active material Substances 0.000 abstract 1
- -1 amine salts Chemical class 0.000 description 31
- 210000003491 skin Anatomy 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000194 fatty acid Substances 0.000 description 17
- 239000000463 material Substances 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 150000002690 malonic acid derivatives Chemical class 0.000 description 11
- 150000002191 fatty alcohols Chemical class 0.000 description 10
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 9
- 239000003974 emollient agent Substances 0.000 description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 9
- 239000003755 preservative agent Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- 229940008099 dimethicone Drugs 0.000 description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 5
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000000017 hydrogel Substances 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- FRRMMWJCHSFNSG-UHFFFAOYSA-N diazanium;propanedioate Chemical compound [NH4+].[NH4+].[O-]C(=O)CC([O-])=O FRRMMWJCHSFNSG-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229920002545 silicone oil Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229940088594 vitamin Drugs 0.000 description 4
- 229930003231 vitamin Natural products 0.000 description 4
- 235000013343 vitamin Nutrition 0.000 description 4
- 239000011782 vitamin Substances 0.000 description 4
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- DSEKYWAQQVUQTP-UHFFFAOYSA-N Cerin Natural products CC12CCC3(C)C4CC(C)(C)CCC4(C)CCC3(C)C2CCC2(C)C1CC(O)C(=O)C2C DSEKYWAQQVUQTP-UHFFFAOYSA-N 0.000 description 3
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 3
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Natural products C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 210000002615 epidermis Anatomy 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 239000003906 humectant Substances 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- 229960003966 nicotinamide Drugs 0.000 description 3
- 235000005152 nicotinamide Nutrition 0.000 description 3
- 239000011570 nicotinamide Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 239000000516 sunscreening agent Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical class CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 229940043268 2,2,4,4,6,8,8-heptamethylnonane Drugs 0.000 description 2
- DWHIUNMOTRUVPG-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCO DWHIUNMOTRUVPG-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ATGQXSBKTQANOH-UWVGARPKSA-N N-oleoylphytosphingosine Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@H](CO)NC(=O)CCCCCCC\C=C/CCCCCCCC ATGQXSBKTQANOH-UWVGARPKSA-N 0.000 description 2
- 239000004264 Petrolatum Substances 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 206010040844 Skin exfoliation Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229940106189 ceramide Drugs 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 239000008278 cosmetic cream Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 2
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 2
- 230000037336 dry skin Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Natural products CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 229940031674 laureth-7 Drugs 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 229920001206 natural gum Polymers 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 2
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- 239000002884 skin cream Substances 0.000 description 1
- 230000035483 skin reaction Effects 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
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- 229940031688 sodium c14-16 olefin sulfonate Drugs 0.000 description 1
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- DSOWAKKSGYUMTF-GZOLSCHFSA-M sodium;(1e)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethanolate Chemical compound [Na+].C\C([O-])=C1/C(=O)OC(C)=CC1=O DSOWAKKSGYUMTF-GZOLSCHFSA-M 0.000 description 1
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- 235000019385 spermaceti wax Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- 229940098780 tribehenin Drugs 0.000 description 1
- HTJNEBVCZXHBNJ-XCTPRCOBSA-H trimagnesium;(2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;diphosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O HTJNEBVCZXHBNJ-XCTPRCOBSA-H 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019164 vitamin B2 Nutrition 0.000 description 1
- 239000011716 vitamin B2 Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
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- 229940011671 vitamin b6 Drugs 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
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- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0208—Tissues; Wipes; Patches
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/046—Aerosols; Foams
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/362—Polycarboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/12—Face or body powders for grooming, adorning or absorbing
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Emergency Medicine (AREA)
- Dispersion Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
A cosmetic composition is provided which includes as an active material a salt of malonic acid in a cosmetically acceptable carrier, wherein the composition exhibits a Flexibility Value greater than 1 according to the Porcine Skin Test.
Description
COSMETIC COMPOSITIONS
CONTAINING SALTS OF MALONIC ACID
The invention concerns cosmetic compositions containing salts of malonic acid, and use of these compositions to control the signs of skin aging.
A soft, supple and flexible skin has a marked cosmetic appeal and is an attribute of normal functioning epidermis.
As human skin ages with advancing years, the epidermis can become folded, ridged or furrowed to form wrinkles. These signal loss of youthful appearance and herald the transition to old age. Exposure to excessive doses of sunlight accelerates the transition process. Also, the outer layer of the epidermis known as the stratum corneum can become dry and flaky following exposure to cold weather or excessive contact with detergents or solvents. Loss of skin moisture thereby results and the skin begins to lose the soft, supple and flexible characteristics.
Emollients such as fats, phospholipids and sterols have in the past been used to soften wrinkled or dry skin. These emollients are only partially effective as a remedy for skin in poor condition.
The use of hydroxy carboxylic acids for enhancing the quality of human skin has been known for some time. There is no doubt that alpha-hydroxy carboxylic acids are effective much beyond the common emollients.
CONTAINING SALTS OF MALONIC ACID
The invention concerns cosmetic compositions containing salts of malonic acid, and use of these compositions to control the signs of skin aging.
A soft, supple and flexible skin has a marked cosmetic appeal and is an attribute of normal functioning epidermis.
As human skin ages with advancing years, the epidermis can become folded, ridged or furrowed to form wrinkles. These signal loss of youthful appearance and herald the transition to old age. Exposure to excessive doses of sunlight accelerates the transition process. Also, the outer layer of the epidermis known as the stratum corneum can become dry and flaky following exposure to cold weather or excessive contact with detergents or solvents. Loss of skin moisture thereby results and the skin begins to lose the soft, supple and flexible characteristics.
Emollients such as fats, phospholipids and sterols have in the past been used to soften wrinkled or dry skin. These emollients are only partially effective as a remedy for skin in poor condition.
The use of hydroxy carboxylic acids for enhancing the quality of human skin has been known for some time. There is no doubt that alpha-hydroxy carboxylic acids are effective much beyond the common emollients.
- 2 -U.S. Patent 4,424,234 (Alderson et al.) discloses skin treatment compositions incorporating alpha-hydroxycaproic acid and alpha-hydroxycaprylic acid or mixtures thereof in compositions that have a pH value of less than 7, usually from 2 to 4. Yu and Van Scott have patented widely in this area. For instance, U.S. Patent 4,105,782 reports amines or ammonium salts of alpha-hydroxy carboxylic acids in the treatment of acne or dandruff. In U.S. Patent 4,105,783 and U.S. Patent 4,197,316, these compounds are suggested for the treatment of dry skin. U.S. Patent 4,234,599 discloses the use of alpha-hydroxy carboxylic acids, their esters or amine salts in the treatment of keratoses. More recently, U.S.
Patent 5,091,171 focused attention on these compounds as being effective against age spots, wrinkles and aging related skin changes.
Whilst hydroxy carboxylic acids hold much therapeutic promise, the materials have been found to irritate human skin on repeated topical applications. The irritation may range from a sensation of tingling, itching and burning to clinical signs of redness and peeling. Causes for such irritation have been linked to the lowering of pH in the stratum corneum of human skin. Low pH has been suggested as provoking disturbances in intercorneocyte bondings resulting in adverse skin reactions, especially in some individuals with sensitive skin.
Organic acids other than alpha-hydroxy functionalized have been disclosed in the cosmetic literature. For instance, U.S. Patent 5,641,495 (Jokura et al.) discloses in combination a ceramide or pseudoceramide, a dicarboxylic u: ~'.
Patent 5,091,171 focused attention on these compounds as being effective against age spots, wrinkles and aging related skin changes.
Whilst hydroxy carboxylic acids hold much therapeutic promise, the materials have been found to irritate human skin on repeated topical applications. The irritation may range from a sensation of tingling, itching and burning to clinical signs of redness and peeling. Causes for such irritation have been linked to the lowering of pH in the stratum corneum of human skin. Low pH has been suggested as provoking disturbances in intercorneocyte bondings resulting in adverse skin reactions, especially in some individuals with sensitive skin.
Organic acids other than alpha-hydroxy functionalized have been disclosed in the cosmetic literature. For instance, U.S. Patent 5,641,495 (Jokura et al.) discloses in combination a ceramide or pseudoceramide, a dicarboxylic u: ~'.
-3-acid and a salt of a dicarboxylic acid. The Examples illustrate sodium and potassium salts of succinic acid. Lower molecular weight dicarboxylic acids such as malonic may also be utilized. Although excellent moisturization and little accompanying irritation occurs, there is no suggestion that this system combats signs of aging leading to loss of softness, suppleness, and flexibility of skin. Improvements in these areas remain as an unfulfilled need of the consumer.
Accordingly, it is an advantage of the present invention to provide new cosmetic ingredients in compositions which are effective at controlling and even eliminating the signs of aging, particularly with respect to improving skin softness, suppleness and flexibility.
Thus, according to a first aspect of the invention,, there is provided a cosmetic composition which includes:
(i) from 0.1% to 30% by weight of an ammonium, dimethylethanolammonium or tris(hydroxymethyl)methane ammonium salt of malonic acid, the malonic acid being present as a half neutralized and a fully neutralized acid in a molar ratio ranging from 2:1 to 1:200;
(ii) from about 1% to about 99.9% by weight of a cosmetically acceptable carrier;
wherein the composition exhibits a Flexibility Value greater than 1 inthe Porcine Skin Test.
Furthermore, there is provided a method for controlling signs of aging which includes:
providing a cosmetic composition including:
(i) from 0.1% to 30% by weight of a salt of malonie acid, the malonic acid being present as a half neutralized V fn ' ~~\ k ... E ~' and a fully neutralized acid in a molar ratio ranging from 2:1 to 1:200;
Accordingly, it is an advantage of the present invention to provide new cosmetic ingredients in compositions which are effective at controlling and even eliminating the signs of aging, particularly with respect to improving skin softness, suppleness and flexibility.
Thus, according to a first aspect of the invention,, there is provided a cosmetic composition which includes:
(i) from 0.1% to 30% by weight of an ammonium, dimethylethanolammonium or tris(hydroxymethyl)methane ammonium salt of malonic acid, the malonic acid being present as a half neutralized and a fully neutralized acid in a molar ratio ranging from 2:1 to 1:200;
(ii) from about 1% to about 99.9% by weight of a cosmetically acceptable carrier;
wherein the composition exhibits a Flexibility Value greater than 1 inthe Porcine Skin Test.
Furthermore, there is provided a method for controlling signs of aging which includes:
providing a cosmetic composition including:
(i) from 0.1% to 30% by weight of a salt of malonie acid, the malonic acid being present as a half neutralized V fn ' ~~\ k ... E ~' and a fully neutralized acid in a molar ratio ranging from 2:1 to 1:200;
4 PCT/EP03/05477 (ii) from about 1% to about 99.9% by weight of a cosmetically acceptable carrier;
wherein the composition exhibits a Flexibility Value greater than 1 in the Porcine Skin Test; and applying the cosmetic composition to the skin.
We have now found that salts of malonic acid are at least as effective as alpha-hydroxy carboxylic acids in combating the signs of skin aging. Most particularly, salts of malonic acid have shown significant activity in improving the softness, suppleness and flexibility of skin.
A feature of the present invention is that malonate salts are those which impart to the composition a positive Flexibility Value of at least 1, preferably at least 1.1 relative to water in the Porcine Skin Test. This test utilizes a thermo-mechanical analyzer with a 20 gram load to a one-cm diameter disc of Porcine Skin from which the immediate deflection is recorded in mm. Water serves as a control. Skin samples are measured before and 24 hours after one, two and three treatments. These treatments consist of 150 ~,l of each composition being applied to the skin for five minutes, then removed without rinsing.
Thereafter, drying is performed at 21°C and less than 100 relative humidity.
Data transformation consists of determining the ratio of the deflection value after three applications of the test composition to the deflection value of the water standard.
The ratio is defined as the Flexibility Value.
wherein the composition exhibits a Flexibility Value greater than 1 in the Porcine Skin Test; and applying the cosmetic composition to the skin.
We have now found that salts of malonic acid are at least as effective as alpha-hydroxy carboxylic acids in combating the signs of skin aging. Most particularly, salts of malonic acid have shown significant activity in improving the softness, suppleness and flexibility of skin.
A feature of the present invention is that malonate salts are those which impart to the composition a positive Flexibility Value of at least 1, preferably at least 1.1 relative to water in the Porcine Skin Test. This test utilizes a thermo-mechanical analyzer with a 20 gram load to a one-cm diameter disc of Porcine Skin from which the immediate deflection is recorded in mm. Water serves as a control. Skin samples are measured before and 24 hours after one, two and three treatments. These treatments consist of 150 ~,l of each composition being applied to the skin for five minutes, then removed without rinsing.
Thereafter, drying is performed at 21°C and less than 100 relative humidity.
Data transformation consists of determining the ratio of the deflection value after three applications of the test composition to the deflection value of the water standard.
The ratio is defined as the Flexibility Value.
- 5 -A wide variety of counter rations to the malonate anions may be utilized in forming the salt. Malonate salts may either be the half or fully neutralized malonic acid or combinations thereof, as represented by general formulas (I) and (II) [H02CCH~CO~] [X] + + [X] 2 [02CCH~C02]
I II
wherein X is a cationic counterion.
Suitable cationic counterions include those of alkali and alkaline earth metals. Representative examples include the rations of lithium, sodium, potassium, magnesium, calcium, ammonium and combinations thereof.
Not only inorganic but also organic rations can be employed.
Particularly useful are quaternized nitrogen rations having from 1 to 1,000, preferably from 1 to 20, and optimally from 3 to 12 carbon atoms. Illustrative are those rations derived from amines which include triethanolamine, diethanolamine, propanolamine, monoethanolamine, methylamine, ethylamine, propylamine, isopropylamine, butylamine, isobutylamine, t-butylamine, pentylamine, isopentylamine, hexylamine, cyclohexylamine, cyclopentylamine, norbornylamine, octylamine, ethylhexylamine, nonylamine, decylamine, pyrrolidone, amino acids (lysine, arginine, alanine, glutamine, histidine, glycine), 2-amino-2-methyl-1-propanol, dimethylethanolamine, polyethyleneimine, tris(hydroxymethyl)amino methane and combinations thereof.
a, 7 CA 02486905 2004-11-22 ~~~'~~~"HG~.,~ ~°;'
I II
wherein X is a cationic counterion.
Suitable cationic counterions include those of alkali and alkaline earth metals. Representative examples include the rations of lithium, sodium, potassium, magnesium, calcium, ammonium and combinations thereof.
Not only inorganic but also organic rations can be employed.
Particularly useful are quaternized nitrogen rations having from 1 to 1,000, preferably from 1 to 20, and optimally from 3 to 12 carbon atoms. Illustrative are those rations derived from amines which include triethanolamine, diethanolamine, propanolamine, monoethanolamine, methylamine, ethylamine, propylamine, isopropylamine, butylamine, isobutylamine, t-butylamine, pentylamine, isopentylamine, hexylamine, cyclohexylamine, cyclopentylamine, norbornylamine, octylamine, ethylhexylamine, nonylamine, decylamine, pyrrolidone, amino acids (lysine, arginine, alanine, glutamine, histidine, glycine), 2-amino-2-methyl-1-propanol, dimethylethanolamine, polyethyleneimine, tris(hydroxymethyl)amino methane and combinations thereof.
a, 7 CA 02486905 2004-11-22 ~~~'~~~"HG~.,~ ~°;'
-6-Most prefexxed are the cations derived from ammonia, dimethylethanolamine and tris(hydroxymethyl)amino~methane.
Typical malonate salts derived from these preferred materials include ammonium malonate, diammonium malonate, dimethylethanolammonium malonate, bis (dimethylethanolammonium) malonate, tris(hydroxymethyl)methane ammonium malonate, and di [tris (hydroxymethyl ) methane ammonium] malonate .
Amounts of the malonic acid salt may range from about 0.1% to about 30%, preferably from about 0.1% to about 15%, more preferably from about 0.5% to about 10%, optimally from about I% to about 8% by weight of the cosmetic composition.
The present invention utilizes as the active ingredient mixtures of salt I and salt II. The molar ratio of mono-salt I
to di-salt II may range from about 2:1 to about 1:200, optimal3y from about 1:1 to about 1:20.
Compositions of this invention will also include a cosmetically acceptable carrier. Amounts of the carrier may range from 1%
to 99.9%, preferably from about 70% to about 95%, optimally from about 80% to about 90%. Among the useful carriers are water, emollients, fatty acids, fatty alcohols, humectants, thickeners and combinations thereof. The carrier may be aqueous, anhydrous or an emulsion. Preferably the compositions are aqueous, especially water and oil emulsions of the W/O or O/W or triplex W/O/W
_ 7 _ variety. Water when present may be in amounts ranging from about 5% to about 950, preferably from about 20% to about 70%, optimally from about 35o to about 60% by weight.
Emollient materials may serve as cosmetically acceptable carriers. These may be in the form of silicone oils, synthetic esters and hydrocarbons. Amounts of the emollients may range anywhere from about 0.1% to about 95o, preferably between about 1% and about 50% by weight.
Silicone oils may be divided into the volatile and nonvolatile variety. The term "volatile" as used herein refers to those materials which have a measurable vapor pressure at ambient temperature. Volatile silicone oils are preferably chosen from cyclic (cyclomethicone) or linear polydimethylsiloxanes containing from 3 to 9, preferably from 4 to 5, silicon atoms.
Non-volatile silicone oils useful as an emollient material include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane copolymers. The essentially non-volatile polyalkyl siloxanes useful herein include, for example, polydimethyl siloxanes with viscosities of from about 5 x 10 to 0.1 m2/s at 25°C. Among the preferred non-volatile emollients useful in the present compositions are the polydimethyl siloxanes having viscosities from about 1 x 10 to about 4 x 10 4 m2/s at 25°C.
Another class of non-volatile silicones are emulsifying and non-emulsifying silicone elastomers. Representative of this _ g _ category is Dimethicone/Vinyl Dimethicone Crosspolymer available as Dow Corning 9040, General Electric SFE 839, and Shin-Etsu KSG-18. Silicone waxes such as Silwax WS-L
(Dimethicone Copolyol Laurate) may also be useful.
Among the ester emollients are:
(1) Alkenyl or alkyl esters of fatty acidshaving 10 to 20 carbon atoms. Examples thereof include isoarachidyl neopentanoate, isononyl isonanonoate, oleyl myristate, oleyl stearate, and oleyl oleate.
(2) Ether-esters such as fatty acid esters of ethoxylated fatty alcohols.
(3) Polyhydric alcohol esters. Ethylene glycol mono and di-fatty acid esters, diethylene glycol mono- and di-fatty acid esters, polyethylene glycol (200-6000) mono- and di-fatty acid esters, propylene glycol mono- and di-fatty acid esters, polypropylene glycol 2000 monooleate, polypropylene glycol 2000 monostearate, ethoxylated propylene glycol monostearate, glyceryl mono- and di-fatty acid esters, polyglycerol poly-fatty esters, ethoxylated glyceryl mono-stearate, 1,3-butylene glycol monostearate, 1,3-butylene glycol distearate, polyoxyethylene polyol fatty acid ester, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters are satisfactory polyhydric alcohol esters. Particularly useful are _ g _ pentaerythritol, trimethylolpropane and neopentyl glycol esters of C1-C3p alcohols.
(4) Wax esters such as beeswax, spermaceti wax and tribehenin wax.
(5) Sterols esters, of which cholesterol fatty acid esters are examples thereof.
(6) Sugar ester of fatty acids such as sucrose polybehenate and sucrose polycottonseedate.
Hydrocarbons which are suitable cosmetically acceptable carriers include petrolatum, mineral oil, C11-C13 isoparaffins, polyalphaolefins, and especially isohexadecane, available commercially as Permethyl 101A from Presperse Inc.
Fatty acids having from 10 to 30 carbon atoms may also be suitable as cosmetically acceptable carriers. Illustrative of this category are pelargonic, lauric, myristic, palmitic, stearic, isostearic, hydroxystearic, oleic, linoleic, ricinoleic, arachidic, behenic and erucic acids.
Fatty alcohols having from 10 to 30 carbon atoms are another useful category of cosmetically acceptable carrier.
Illustrative of this category are stearyl alcohol, lauryl alcohol, myristyl alcohol and cetyl alcohol.
Humectants of the polyhydric alcohol-type can be employed as cosmetically acceptable carriers. Typical polyhydric alcohols include glycerol, polyalkylene glycols and more preferably alkylene polyols and their derivatives, including propylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol and derivatives thereof, sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1,3-butylene glycol, isoprene glycol, 1,2,6-hexanetriol, ethoxylated glycerol, propoxylated glycerol and mixtures thereof. The amount of humectant may range anywhere from 0.5o to 50%, preferably between 1% and 15% by weight of the composition.
Thickeners can be utilized as part of the cosmetically acceptable carrier of compositions according to the present invention. Typical thickeners include crosslinked acrylates (e. g. Carbopol 982~), hydrophobically-modified acrylates (e. g. Carbopol 1382~), cellulosic derivatives and natural gums. Among useful cellulosic derivatives are sodium carboxymethylcellulose, hydroxypropyl methocellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, ethyl cellulose and hydroxymethyl cellulose. Natural gums suitable for the present invention include guar, xanthan, sclerotium, carrageenan, pectin and combinations of these gums.
Inorganics may also be utilized as thickeners, particularly clays such as bentonites and hectorites, fumed silicas, and silicates such as magnesium aluminum silicate (Veegum~).
Amounts of the thickener may range from 0.0001% to 100, usually from 0.001% to lo, optimally from O.Olo to 0.5% by weight.
Cosmetic compositions of the present invention may be in any form. These forms may include lotions, creams, roll-on formulations, sticks, mousses, aerosol and non-aerosol sprays and fabric (e. g. nonwoven textile)-applied formulations.
Surfactants may also be present in cosmetic compositions of the present invention. Total concentration of the surfactant when present may range from about 0.1o to about 40~, preferably from about 1% to about 20%, optimally from about 1% to about 5% by weight of the composition. The surfactant may be selected from the group consisting of anionic, nonionic, cationic and amphoteriC actives.
Particularly preferred nonionic surfactants are those with a C1p-C2p fatty alcohol or acid hydrophobe condensed with from 2 to 100 moles of ethylene oxide or propylene oxide per mole of hydrophobe; C2-C1p alkyl phenols condensed with from 2 to moles of alkylene oxide; mono- and di-fatty acid esters of ethylene glycol; fatty acid monoglyceride; sorbitan, mono- and di- Cg-C2p fatty acids; and polyoxyethylene 20 sorbitan as well as combinations thereof. Alkyl polyglyCOSides and saccharide fatty amides (e. g. methyl gluCOnamides) are also suitable nonionic surfactants.
Preferred anionic surfactants include soap, alkyl ether sulfates and sulfonates, alkyl sulfates and sulfonates, alkylbenzene sulfonates, alkyl and dialkyl sulfosuCCinates, Cg-C2p aryl isethionate, Cg-C2p alkyl ether phosphates, Cg-Cep sarcosinates and combinations thereof.
Sunscreen actives may also be included in compositions of the present invention. Particularly preferred are such materials as ethylhexyl p-methoxycinnamate, available as Parsol MCX~, Avobenzene, available as Parsol 1789~ and benzophenone-3, also known as Oxybenzone. Inorganic sunscreen actives may be employed such as microfine titanium dioxide, zinc oxide, polyethylene and various other polymers. Amounts of the sunscreen agents when present may generally range from 0.1% to 300, preferably from 2% to 200, optimally from 4% to 10o by weight.
Preservatives can desirably be incorporated into the cosmetic compositions of this invention to protect against the growth of potentially harmful microorganisms. Suitable traditional preservatives for compositions of this invention are alkyl esters of para-hydroxybenzoic acid. Other preservatives which have more recently come into use include hydantoin derivatives, propionate salts, and a variety of quaternary ammonium compounds. Cosmetic chemists are familiar with appropriate preservatives and routinely choose them to satisfy the preservative challenge test and to provide product stability.
Particularly preferred preservatives are phenoxyethanol, methyl paraben, propyl paraben, imidazolidinyl urea, sodium dehydroacetate and benzyl alcohol. The preservatives should be selected having regard for the use of the composition and possible incompatibilities between the preservatives and other ingredients in the emulsion. Preservatives are preferably employed in amounts ranging from 0.01% to 2% by weight of the composition.
Compositions of the present invention may include vitamins.
Illustrative vitamins are Vitamin A (retinol), Vitamin B2, Vitamin B6, Vitamin C, Vitamin E and Biotin. Derivatives of the vitamins may also be employed. For instance, Vitamin C
derivatives include ascorbyl tetraisopalmitate, magnesium ascorbyl phosphate and ascorbyl glycoside. Derivatives of Vitamin E include tocopheryl acetate, tocopheryl palmitate and tocopheryl linoleate. DL-panthenol and derivatives may also be employed. Total amount of vitamins when present in compositions according to the present invention may range from 0.0010 to 10%, preferably from 0.01% to 10, optimally from 0.10 to 0.50 by weight.
Another type of useful substance can be that of an enzyme such as oxidases, proteases, lipases and combinations.
Particularly preferred is superoxide dismutase, commercially available as Biocell SOD from the Brooks Company, USA.
Skin lightening compounds may be included in the compositions of the invention. Illustrative substances are placental extract, lactic acid, niacinamide, arbutin, kojic acid, ferulic acid, resorcinol and derivatives including 4-substituted resorcinols and combinations thereof. Amounts of these agents may range from about 0.1% to about 10%, preferably from about 0.5% to about 2% by weight of the compositions.
Desquamation promoters may be present. Illustrative are the alpha-hydroxycarboxylic acids and beta-hydroxycarboxylic acids. The term "acid" is meant to include not only the free acid but also salts and C1-C3p alkyl or aryl esters thereof and lactones generated from removal of water to form cyclic or linear lactone structures. Representative acids are glycolic, lactic and malic acids. Salicylic acid is representative of the beta-hydroxycarboxylic acids. Amounts of these materials when present may range from about 0.010 to about 15% by weight of the composition.
A variety of herbal extracts may optionally be included in compositions of this invention. Illustrative are green tea, chamomile, licorice and extract combinations thereof. The extracts may either be water soluble or water-insoluble carried in a solvent which respectively is hydrophilic or hydrophobic. Water and ethanol are the preferred extract solvents.
Also included may be such materials as lipoic acid, retinoxytrimethylsilane (available from Clariant Corp. under the Silcare 1M-75 trademark), dehydroepiandrosterone (DHEA) and combinations thereof. Ceramides (including Ceramide 1, Ceramide 3, Ceramide 3B and Ceramide 6) as well as pseudoceramides may also be utilized for many compositions of the present invention may also be excluded. Amounts of these materials may range from about 0.0000010 to about 100, preferably from about 0.0001% to about 1o by weight.
Colorants, fragrances, opacifiers and abrasives may also be included in compositions of the present invention. Each of these substances may range from about 0.05% to about 50, preferably between 0.1% and 3% by weight.
The term "comprising" is meant not to be limiting to any subsequently stated elements but rather to encompass non-specified elements of major or minor functional importance.
In other words the listed steps, elements or options need not be exhaustive. Whenever the words "including" or "having" are used, these terms are meant to be equivalent to "comprising" as defined above.
EXAMPLES
Except in the operating and comparative examples, or where otherwise explicitly indicated, all numbers in this description indicating amounts of material ought to be understood as modified by the word "about".
The following examples will more fully illustrate the embodiments of this invention. All parts, percentages and proportions referred to herein and in the appended claims are by weight unless otherwise illustrated.
Example 1 A typical cosmetic cream according to the present invention is outlined under Table I.
TABLE I
INGREDIENT WEIGHT
PHASE
A
Water Balance Disodium EDTA 0.05 Meth I Paraben 0.15 Ma nesium Aluminum Silicate 0.60 Triethanolamine 1.20 PHASE
B
Xanthan Gum 0.20 Natrosol~ 250HHR eth I 0.50 cellulose But lene GI col 3.00 GI cerin 2.00 PHASE
C
Sodium Stearo I Lact late 0.10 GI cerol Monostearate 1.50 Stea I Alcohol 1.50 Isostea I Palmitate 3.00 Silicone Fluid 1.00 Cholesterol 0.25 Sorbitan Stearate 1.00 But lated H dro Toluene 0.05 Vitamin E Acetate 0.01 PEG-100 Stearate 2.00 Stearic Acid 3.00 Pro I Paraben 0.10 Parsol MCX~ 2.00 Ca lic/Ca ric Tri I ceride 0.50 H dro ca lic Acid 0.01 C12-15 Alk I Octanoate 3.00 PHASE
D
Malonate Salt 3.00 PHASE
E
Vitamin A Palmitate 0.10 Bisabolol 0.01 Vitamin A Acetate 0.01 Fra rance 0.03 Retinol 50C 0.02 Example 2 A water-in-oil topical liquid make-up foundation utilizing the malonate salts of the present invention is described in Table II below.
TABLE II
INGREDIENT WEIGHT
PHASE
A
C clomethicone 9.25 Cet I Octanoate 2.00 Dimethicone Co of of 20.00 PHASE
B
Talc 3.38 Pi ment Iron Oxides 10.51 S heron L-1500 Silica 0.50 PHASE
C
S nthetic Wax Durachem 0.10 Arachid I Behenate 0.30 PHASE
D
C clomethicone 1.00 Trih drox stearin ~ 0.30 PHASE
E
Laureth-7 0.50 Pro I Paraben 0.25 PHASE
F
Fra rance 0.05 PHASE
G
Water balance Ammonium Malonate 3.00 Meth I Paraben 0.12 Pro lens GI col 8.00 Niacinamide 4.00 GI cerin 3.00 Sodium Chloride 2.00 Sodium Deh droacetate 0.30 Example 3 Illustrated herein is a skin cream incorporating the malonate salts of the present invention.
TABLE III
INGREDIENT WEIGHT
GI cerin 6.93 Niacinamide 5.00 Dimeth lethanolammonium Malonate5.00 Permeth I 101 A 3.00 Se i e1305 2.50 Q2-1403 2.00 Iso ro I Isostearate 1.33 Arlatone 2121 1.00 Cet I Alcohol CO-1695 0.72 SEFA Cottonate 0.67 Toco herol Acetate 0.50 Panthenol 0.50 Stea I Alcohol 0.48 Titanium Dioxide 0.40 Disodium EDTA 0.10 GI dant Plus 0.10 PEG-100 Stearate 0.10 Stearic Acid 0.10 Purified Water Balance 1 Isohexadecane, Presperse Inc., South Plainfield, NJ
Polyacrylamide(and)C13-14 Isoparaffin(and) Laureth-7, l0 Seppic Corporation, Fairfield, NJ
3 dimethicone(and)dimethiconol, Dow Corning Corp. Midland, MI
4 Sorbitan Monostearate and Sucrococoate, ICI Americas Inc., Wilmington, DE
5 Sucrose ester of fatty acid CA 02486905 2004-11-22 '~a ~'. '~
u' o c ' S
6 DMDM Hydantoin (and) Iodopropynyl Butylcarbamate, Lonza Inc., Fairlawn, NJ
Example 4 Illustrative of a powdered cosmetic composition according to the present invention is the formula of Table IV.
TABLE IV
INGREDIENT WEIGHT
Pol silicone-11 27.5 C clomethicone 54 Petrolatum 11 Tris h dro meth I methaneammonium Malonate 7 Dimethicone Co of of 0.5 Example 6 An aerosol packaged foaming cleanser suitable for the present invention is outlined in Table VI.
TABLE VI
INGREDIENT WEIGHT
Sunflower Seed Oil 20.00 Maleated So bean Oil 5.00 Silicone Urethane 1.00 Pol I cero-4 Oleate 1.00 Sodium C14-16 Olefin Sulfonate 15.00 Sodium Lau I Ether Sul hate 25% 15.00 active Cocoamido ro Ibetaine 15.00 DC 1754~ Silicone Emulsion 50% 5.00 Pol uaternium-11 1.00 Malonate 1.00 monium Bis dimeth lethanolam _ ~ Balance _ Water An aerosol is prepared using 92% by weight of the concentrate in Table VI~and 8o propellant, the latter being a combination of dimethylether, isobutane and propane.
Example 7 An adhesive cosmetic patch may also be formulated according to the present invention. An adhesive hydrogel is prepared by mixing 30 grams of 2-aCrylamido-2-methylpropane sulphonic acid monomer in 20 grams distilled water and 5 grams of a 1%
aqueous solution of methylene-bis-acrylamide. The solution is then activated with. 0.4% magnesium persulphate catalyst.
Shortly after mixing the catalyst with the hydrogel solution, 0.1 grams ammonium malonate in 5 ml water is added. The resultant solution is coated onto a 50/50 blend of polypropylene and hydrophilic polyester and allowed to solidify. The resulting deposited hydrogel is warmed for 24 hours at 40°C in a hot air oven. Final water content of the hydrogel is 50%. A polystyrene backing layer is laid over the adhesive hydrogel.
Example 9 A variety of carboxylic acid salts were evaluated to determine their response in a Porcine Skin Test. A Perkin-Elmer Thermo-Mechanical Analyzer, Model TMS-1, was operated with a 20 gram load placed to a center of a one-cm diameter disc of Porcine Skin. Deflection of the skin in mm was immediately recorded.
The sample size was six pieces of skin per treatment. Water was used as a control. Each piece served as an internal control. Each was measured dry before and 24 hours after one, two and three treatments.
Each treatment consisted of 150,1 of a test material solution applied to skin for 5 minutes, then removed without rinsing. Drying conditions were 21°C and less then 100 humidity. Results are recorded in Table VIII.
TABLE VIII
Material Evaluated Flexibilit Value Water reference standard 1.00 Succinate Salt* 0.85 GI colate Salt* 0.85 Malonate Salt** ~ 1.36 * ammonium salt ** dimethylethanolammonium salt Evident from the results is that the malonate salt rendered the skin significantly more flexible. By contrast, the succinate and glycolate salts rendered the skin significantly stiffer. The effects of glycolate and succinate were statistically similar. These results indicate that malonate salts and compositions containing these salts can improve the softness, suppleness and flexibility.
Table IX records Flexibility Values as measured on the cosmetic cream formulation detailed under Table I (utilizing different Phase D actives). Flexibility Value for the malonate salt formulated cream was higher than either the base cream or a glycolate salt formulated cream. The results demonstrate that a softer, suppler and more flexible skin is achieved by use of malonates.
TABLE IX
Material Evaluated* Fllexibilit Value Water preference standard 1.00 Base Cream No Salt O,gg Base Cream GI colate Salt 0.84 Base Cream Malonate Salt 1.12 * Salt in parenthesis refers to Phase D active of Example 1 (Table I ) The foregoing description and examples illustrate selected embodiments of the present invention. In light thereof variations and modifications will be suggested to one skilled in the art, all of which are within the spirit and purview of this invention.
Typical malonate salts derived from these preferred materials include ammonium malonate, diammonium malonate, dimethylethanolammonium malonate, bis (dimethylethanolammonium) malonate, tris(hydroxymethyl)methane ammonium malonate, and di [tris (hydroxymethyl ) methane ammonium] malonate .
Amounts of the malonic acid salt may range from about 0.1% to about 30%, preferably from about 0.1% to about 15%, more preferably from about 0.5% to about 10%, optimally from about I% to about 8% by weight of the cosmetic composition.
The present invention utilizes as the active ingredient mixtures of salt I and salt II. The molar ratio of mono-salt I
to di-salt II may range from about 2:1 to about 1:200, optimal3y from about 1:1 to about 1:20.
Compositions of this invention will also include a cosmetically acceptable carrier. Amounts of the carrier may range from 1%
to 99.9%, preferably from about 70% to about 95%, optimally from about 80% to about 90%. Among the useful carriers are water, emollients, fatty acids, fatty alcohols, humectants, thickeners and combinations thereof. The carrier may be aqueous, anhydrous or an emulsion. Preferably the compositions are aqueous, especially water and oil emulsions of the W/O or O/W or triplex W/O/W
_ 7 _ variety. Water when present may be in amounts ranging from about 5% to about 950, preferably from about 20% to about 70%, optimally from about 35o to about 60% by weight.
Emollient materials may serve as cosmetically acceptable carriers. These may be in the form of silicone oils, synthetic esters and hydrocarbons. Amounts of the emollients may range anywhere from about 0.1% to about 95o, preferably between about 1% and about 50% by weight.
Silicone oils may be divided into the volatile and nonvolatile variety. The term "volatile" as used herein refers to those materials which have a measurable vapor pressure at ambient temperature. Volatile silicone oils are preferably chosen from cyclic (cyclomethicone) or linear polydimethylsiloxanes containing from 3 to 9, preferably from 4 to 5, silicon atoms.
Non-volatile silicone oils useful as an emollient material include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane copolymers. The essentially non-volatile polyalkyl siloxanes useful herein include, for example, polydimethyl siloxanes with viscosities of from about 5 x 10 to 0.1 m2/s at 25°C. Among the preferred non-volatile emollients useful in the present compositions are the polydimethyl siloxanes having viscosities from about 1 x 10 to about 4 x 10 4 m2/s at 25°C.
Another class of non-volatile silicones are emulsifying and non-emulsifying silicone elastomers. Representative of this _ g _ category is Dimethicone/Vinyl Dimethicone Crosspolymer available as Dow Corning 9040, General Electric SFE 839, and Shin-Etsu KSG-18. Silicone waxes such as Silwax WS-L
(Dimethicone Copolyol Laurate) may also be useful.
Among the ester emollients are:
(1) Alkenyl or alkyl esters of fatty acidshaving 10 to 20 carbon atoms. Examples thereof include isoarachidyl neopentanoate, isononyl isonanonoate, oleyl myristate, oleyl stearate, and oleyl oleate.
(2) Ether-esters such as fatty acid esters of ethoxylated fatty alcohols.
(3) Polyhydric alcohol esters. Ethylene glycol mono and di-fatty acid esters, diethylene glycol mono- and di-fatty acid esters, polyethylene glycol (200-6000) mono- and di-fatty acid esters, propylene glycol mono- and di-fatty acid esters, polypropylene glycol 2000 monooleate, polypropylene glycol 2000 monostearate, ethoxylated propylene glycol monostearate, glyceryl mono- and di-fatty acid esters, polyglycerol poly-fatty esters, ethoxylated glyceryl mono-stearate, 1,3-butylene glycol monostearate, 1,3-butylene glycol distearate, polyoxyethylene polyol fatty acid ester, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters are satisfactory polyhydric alcohol esters. Particularly useful are _ g _ pentaerythritol, trimethylolpropane and neopentyl glycol esters of C1-C3p alcohols.
(4) Wax esters such as beeswax, spermaceti wax and tribehenin wax.
(5) Sterols esters, of which cholesterol fatty acid esters are examples thereof.
(6) Sugar ester of fatty acids such as sucrose polybehenate and sucrose polycottonseedate.
Hydrocarbons which are suitable cosmetically acceptable carriers include petrolatum, mineral oil, C11-C13 isoparaffins, polyalphaolefins, and especially isohexadecane, available commercially as Permethyl 101A from Presperse Inc.
Fatty acids having from 10 to 30 carbon atoms may also be suitable as cosmetically acceptable carriers. Illustrative of this category are pelargonic, lauric, myristic, palmitic, stearic, isostearic, hydroxystearic, oleic, linoleic, ricinoleic, arachidic, behenic and erucic acids.
Fatty alcohols having from 10 to 30 carbon atoms are another useful category of cosmetically acceptable carrier.
Illustrative of this category are stearyl alcohol, lauryl alcohol, myristyl alcohol and cetyl alcohol.
Humectants of the polyhydric alcohol-type can be employed as cosmetically acceptable carriers. Typical polyhydric alcohols include glycerol, polyalkylene glycols and more preferably alkylene polyols and their derivatives, including propylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol and derivatives thereof, sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1,3-butylene glycol, isoprene glycol, 1,2,6-hexanetriol, ethoxylated glycerol, propoxylated glycerol and mixtures thereof. The amount of humectant may range anywhere from 0.5o to 50%, preferably between 1% and 15% by weight of the composition.
Thickeners can be utilized as part of the cosmetically acceptable carrier of compositions according to the present invention. Typical thickeners include crosslinked acrylates (e. g. Carbopol 982~), hydrophobically-modified acrylates (e. g. Carbopol 1382~), cellulosic derivatives and natural gums. Among useful cellulosic derivatives are sodium carboxymethylcellulose, hydroxypropyl methocellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, ethyl cellulose and hydroxymethyl cellulose. Natural gums suitable for the present invention include guar, xanthan, sclerotium, carrageenan, pectin and combinations of these gums.
Inorganics may also be utilized as thickeners, particularly clays such as bentonites and hectorites, fumed silicas, and silicates such as magnesium aluminum silicate (Veegum~).
Amounts of the thickener may range from 0.0001% to 100, usually from 0.001% to lo, optimally from O.Olo to 0.5% by weight.
Cosmetic compositions of the present invention may be in any form. These forms may include lotions, creams, roll-on formulations, sticks, mousses, aerosol and non-aerosol sprays and fabric (e. g. nonwoven textile)-applied formulations.
Surfactants may also be present in cosmetic compositions of the present invention. Total concentration of the surfactant when present may range from about 0.1o to about 40~, preferably from about 1% to about 20%, optimally from about 1% to about 5% by weight of the composition. The surfactant may be selected from the group consisting of anionic, nonionic, cationic and amphoteriC actives.
Particularly preferred nonionic surfactants are those with a C1p-C2p fatty alcohol or acid hydrophobe condensed with from 2 to 100 moles of ethylene oxide or propylene oxide per mole of hydrophobe; C2-C1p alkyl phenols condensed with from 2 to moles of alkylene oxide; mono- and di-fatty acid esters of ethylene glycol; fatty acid monoglyceride; sorbitan, mono- and di- Cg-C2p fatty acids; and polyoxyethylene 20 sorbitan as well as combinations thereof. Alkyl polyglyCOSides and saccharide fatty amides (e. g. methyl gluCOnamides) are also suitable nonionic surfactants.
Preferred anionic surfactants include soap, alkyl ether sulfates and sulfonates, alkyl sulfates and sulfonates, alkylbenzene sulfonates, alkyl and dialkyl sulfosuCCinates, Cg-C2p aryl isethionate, Cg-C2p alkyl ether phosphates, Cg-Cep sarcosinates and combinations thereof.
Sunscreen actives may also be included in compositions of the present invention. Particularly preferred are such materials as ethylhexyl p-methoxycinnamate, available as Parsol MCX~, Avobenzene, available as Parsol 1789~ and benzophenone-3, also known as Oxybenzone. Inorganic sunscreen actives may be employed such as microfine titanium dioxide, zinc oxide, polyethylene and various other polymers. Amounts of the sunscreen agents when present may generally range from 0.1% to 300, preferably from 2% to 200, optimally from 4% to 10o by weight.
Preservatives can desirably be incorporated into the cosmetic compositions of this invention to protect against the growth of potentially harmful microorganisms. Suitable traditional preservatives for compositions of this invention are alkyl esters of para-hydroxybenzoic acid. Other preservatives which have more recently come into use include hydantoin derivatives, propionate salts, and a variety of quaternary ammonium compounds. Cosmetic chemists are familiar with appropriate preservatives and routinely choose them to satisfy the preservative challenge test and to provide product stability.
Particularly preferred preservatives are phenoxyethanol, methyl paraben, propyl paraben, imidazolidinyl urea, sodium dehydroacetate and benzyl alcohol. The preservatives should be selected having regard for the use of the composition and possible incompatibilities between the preservatives and other ingredients in the emulsion. Preservatives are preferably employed in amounts ranging from 0.01% to 2% by weight of the composition.
Compositions of the present invention may include vitamins.
Illustrative vitamins are Vitamin A (retinol), Vitamin B2, Vitamin B6, Vitamin C, Vitamin E and Biotin. Derivatives of the vitamins may also be employed. For instance, Vitamin C
derivatives include ascorbyl tetraisopalmitate, magnesium ascorbyl phosphate and ascorbyl glycoside. Derivatives of Vitamin E include tocopheryl acetate, tocopheryl palmitate and tocopheryl linoleate. DL-panthenol and derivatives may also be employed. Total amount of vitamins when present in compositions according to the present invention may range from 0.0010 to 10%, preferably from 0.01% to 10, optimally from 0.10 to 0.50 by weight.
Another type of useful substance can be that of an enzyme such as oxidases, proteases, lipases and combinations.
Particularly preferred is superoxide dismutase, commercially available as Biocell SOD from the Brooks Company, USA.
Skin lightening compounds may be included in the compositions of the invention. Illustrative substances are placental extract, lactic acid, niacinamide, arbutin, kojic acid, ferulic acid, resorcinol and derivatives including 4-substituted resorcinols and combinations thereof. Amounts of these agents may range from about 0.1% to about 10%, preferably from about 0.5% to about 2% by weight of the compositions.
Desquamation promoters may be present. Illustrative are the alpha-hydroxycarboxylic acids and beta-hydroxycarboxylic acids. The term "acid" is meant to include not only the free acid but also salts and C1-C3p alkyl or aryl esters thereof and lactones generated from removal of water to form cyclic or linear lactone structures. Representative acids are glycolic, lactic and malic acids. Salicylic acid is representative of the beta-hydroxycarboxylic acids. Amounts of these materials when present may range from about 0.010 to about 15% by weight of the composition.
A variety of herbal extracts may optionally be included in compositions of this invention. Illustrative are green tea, chamomile, licorice and extract combinations thereof. The extracts may either be water soluble or water-insoluble carried in a solvent which respectively is hydrophilic or hydrophobic. Water and ethanol are the preferred extract solvents.
Also included may be such materials as lipoic acid, retinoxytrimethylsilane (available from Clariant Corp. under the Silcare 1M-75 trademark), dehydroepiandrosterone (DHEA) and combinations thereof. Ceramides (including Ceramide 1, Ceramide 3, Ceramide 3B and Ceramide 6) as well as pseudoceramides may also be utilized for many compositions of the present invention may also be excluded. Amounts of these materials may range from about 0.0000010 to about 100, preferably from about 0.0001% to about 1o by weight.
Colorants, fragrances, opacifiers and abrasives may also be included in compositions of the present invention. Each of these substances may range from about 0.05% to about 50, preferably between 0.1% and 3% by weight.
The term "comprising" is meant not to be limiting to any subsequently stated elements but rather to encompass non-specified elements of major or minor functional importance.
In other words the listed steps, elements or options need not be exhaustive. Whenever the words "including" or "having" are used, these terms are meant to be equivalent to "comprising" as defined above.
EXAMPLES
Except in the operating and comparative examples, or where otherwise explicitly indicated, all numbers in this description indicating amounts of material ought to be understood as modified by the word "about".
The following examples will more fully illustrate the embodiments of this invention. All parts, percentages and proportions referred to herein and in the appended claims are by weight unless otherwise illustrated.
Example 1 A typical cosmetic cream according to the present invention is outlined under Table I.
TABLE I
INGREDIENT WEIGHT
PHASE
A
Water Balance Disodium EDTA 0.05 Meth I Paraben 0.15 Ma nesium Aluminum Silicate 0.60 Triethanolamine 1.20 PHASE
B
Xanthan Gum 0.20 Natrosol~ 250HHR eth I 0.50 cellulose But lene GI col 3.00 GI cerin 2.00 PHASE
C
Sodium Stearo I Lact late 0.10 GI cerol Monostearate 1.50 Stea I Alcohol 1.50 Isostea I Palmitate 3.00 Silicone Fluid 1.00 Cholesterol 0.25 Sorbitan Stearate 1.00 But lated H dro Toluene 0.05 Vitamin E Acetate 0.01 PEG-100 Stearate 2.00 Stearic Acid 3.00 Pro I Paraben 0.10 Parsol MCX~ 2.00 Ca lic/Ca ric Tri I ceride 0.50 H dro ca lic Acid 0.01 C12-15 Alk I Octanoate 3.00 PHASE
D
Malonate Salt 3.00 PHASE
E
Vitamin A Palmitate 0.10 Bisabolol 0.01 Vitamin A Acetate 0.01 Fra rance 0.03 Retinol 50C 0.02 Example 2 A water-in-oil topical liquid make-up foundation utilizing the malonate salts of the present invention is described in Table II below.
TABLE II
INGREDIENT WEIGHT
PHASE
A
C clomethicone 9.25 Cet I Octanoate 2.00 Dimethicone Co of of 20.00 PHASE
B
Talc 3.38 Pi ment Iron Oxides 10.51 S heron L-1500 Silica 0.50 PHASE
C
S nthetic Wax Durachem 0.10 Arachid I Behenate 0.30 PHASE
D
C clomethicone 1.00 Trih drox stearin ~ 0.30 PHASE
E
Laureth-7 0.50 Pro I Paraben 0.25 PHASE
F
Fra rance 0.05 PHASE
G
Water balance Ammonium Malonate 3.00 Meth I Paraben 0.12 Pro lens GI col 8.00 Niacinamide 4.00 GI cerin 3.00 Sodium Chloride 2.00 Sodium Deh droacetate 0.30 Example 3 Illustrated herein is a skin cream incorporating the malonate salts of the present invention.
TABLE III
INGREDIENT WEIGHT
GI cerin 6.93 Niacinamide 5.00 Dimeth lethanolammonium Malonate5.00 Permeth I 101 A 3.00 Se i e1305 2.50 Q2-1403 2.00 Iso ro I Isostearate 1.33 Arlatone 2121 1.00 Cet I Alcohol CO-1695 0.72 SEFA Cottonate 0.67 Toco herol Acetate 0.50 Panthenol 0.50 Stea I Alcohol 0.48 Titanium Dioxide 0.40 Disodium EDTA 0.10 GI dant Plus 0.10 PEG-100 Stearate 0.10 Stearic Acid 0.10 Purified Water Balance 1 Isohexadecane, Presperse Inc., South Plainfield, NJ
Polyacrylamide(and)C13-14 Isoparaffin(and) Laureth-7, l0 Seppic Corporation, Fairfield, NJ
3 dimethicone(and)dimethiconol, Dow Corning Corp. Midland, MI
4 Sorbitan Monostearate and Sucrococoate, ICI Americas Inc., Wilmington, DE
5 Sucrose ester of fatty acid CA 02486905 2004-11-22 '~a ~'. '~
u' o c ' S
6 DMDM Hydantoin (and) Iodopropynyl Butylcarbamate, Lonza Inc., Fairlawn, NJ
Example 4 Illustrative of a powdered cosmetic composition according to the present invention is the formula of Table IV.
TABLE IV
INGREDIENT WEIGHT
Pol silicone-11 27.5 C clomethicone 54 Petrolatum 11 Tris h dro meth I methaneammonium Malonate 7 Dimethicone Co of of 0.5 Example 6 An aerosol packaged foaming cleanser suitable for the present invention is outlined in Table VI.
TABLE VI
INGREDIENT WEIGHT
Sunflower Seed Oil 20.00 Maleated So bean Oil 5.00 Silicone Urethane 1.00 Pol I cero-4 Oleate 1.00 Sodium C14-16 Olefin Sulfonate 15.00 Sodium Lau I Ether Sul hate 25% 15.00 active Cocoamido ro Ibetaine 15.00 DC 1754~ Silicone Emulsion 50% 5.00 Pol uaternium-11 1.00 Malonate 1.00 monium Bis dimeth lethanolam _ ~ Balance _ Water An aerosol is prepared using 92% by weight of the concentrate in Table VI~and 8o propellant, the latter being a combination of dimethylether, isobutane and propane.
Example 7 An adhesive cosmetic patch may also be formulated according to the present invention. An adhesive hydrogel is prepared by mixing 30 grams of 2-aCrylamido-2-methylpropane sulphonic acid monomer in 20 grams distilled water and 5 grams of a 1%
aqueous solution of methylene-bis-acrylamide. The solution is then activated with. 0.4% magnesium persulphate catalyst.
Shortly after mixing the catalyst with the hydrogel solution, 0.1 grams ammonium malonate in 5 ml water is added. The resultant solution is coated onto a 50/50 blend of polypropylene and hydrophilic polyester and allowed to solidify. The resulting deposited hydrogel is warmed for 24 hours at 40°C in a hot air oven. Final water content of the hydrogel is 50%. A polystyrene backing layer is laid over the adhesive hydrogel.
Example 9 A variety of carboxylic acid salts were evaluated to determine their response in a Porcine Skin Test. A Perkin-Elmer Thermo-Mechanical Analyzer, Model TMS-1, was operated with a 20 gram load placed to a center of a one-cm diameter disc of Porcine Skin. Deflection of the skin in mm was immediately recorded.
The sample size was six pieces of skin per treatment. Water was used as a control. Each piece served as an internal control. Each was measured dry before and 24 hours after one, two and three treatments.
Each treatment consisted of 150,1 of a test material solution applied to skin for 5 minutes, then removed without rinsing. Drying conditions were 21°C and less then 100 humidity. Results are recorded in Table VIII.
TABLE VIII
Material Evaluated Flexibilit Value Water reference standard 1.00 Succinate Salt* 0.85 GI colate Salt* 0.85 Malonate Salt** ~ 1.36 * ammonium salt ** dimethylethanolammonium salt Evident from the results is that the malonate salt rendered the skin significantly more flexible. By contrast, the succinate and glycolate salts rendered the skin significantly stiffer. The effects of glycolate and succinate were statistically similar. These results indicate that malonate salts and compositions containing these salts can improve the softness, suppleness and flexibility.
Table IX records Flexibility Values as measured on the cosmetic cream formulation detailed under Table I (utilizing different Phase D actives). Flexibility Value for the malonate salt formulated cream was higher than either the base cream or a glycolate salt formulated cream. The results demonstrate that a softer, suppler and more flexible skin is achieved by use of malonates.
TABLE IX
Material Evaluated* Fllexibilit Value Water preference standard 1.00 Base Cream No Salt O,gg Base Cream GI colate Salt 0.84 Base Cream Malonate Salt 1.12 * Salt in parenthesis refers to Phase D active of Example 1 (Table I ) The foregoing description and examples illustrate selected embodiments of the present invention. In light thereof variations and modifications will be suggested to one skilled in the art, all of which are within the spirit and purview of this invention.
Claims (7)
1. A cosmetic composition comprising:
(i) from 0.1% to 30% by weight of an ammonium, dimethylethanolammonium or tris(hydroxymethyl)methane ammonium salt of malonic acid, the malonic acid being present as a half neutralized and a fully neutralized acid in a molar ratio ranging from 2:1 to 1:200;
(ii) from about 1% to about 99.9% by weight of a cosmetically acceptable carrier;
wherein the composition exhibits a Flexibility Value greater than 1 in the Porcine Skin Test.
(i) from 0.1% to 30% by weight of an ammonium, dimethylethanolammonium or tris(hydroxymethyl)methane ammonium salt of malonic acid, the malonic acid being present as a half neutralized and a fully neutralized acid in a molar ratio ranging from 2:1 to 1:200;
(ii) from about 1% to about 99.9% by weight of a cosmetically acceptable carrier;
wherein the composition exhibits a Flexibility Value greater than 1 in the Porcine Skin Test.
2. A cosmetic patch or a towelette product containing a cosmetic composition according to claim 1.
3. A method for controlling signs of aging related to softness, suppleness and flexibility comprising:
providing a cosmetic composition comprising:
(i) from 0.1% to 30% by weight of a salt of malonic acid, the malonic acid being present as a half neutralized and a fully neutralized acid in a molar ratio ranging from 2:1 to 1:200;
(ii) from about 1% to about 99.9% by weight of a cosmetically acceptable carrier;
wherein the composition exhibits a Flexibility Value greater than 1 in the Porcine Skin Test; and applying the cosmetic composition to the skin.
providing a cosmetic composition comprising:
(i) from 0.1% to 30% by weight of a salt of malonic acid, the malonic acid being present as a half neutralized and a fully neutralized acid in a molar ratio ranging from 2:1 to 1:200;
(ii) from about 1% to about 99.9% by weight of a cosmetically acceptable carrier;
wherein the composition exhibits a Flexibility Value greater than 1 in the Porcine Skin Test; and applying the cosmetic composition to the skin.
4. The method according to claim 3 wherein the salt of malonic acid is an ammonium, dimethylethanolammonium or tris(hydroxymethyl)methane ammonium salt.
pentylamine, isopentylamine, hexylamine, cyclohexylamine, cyclopentylamine, norbornylamine, octylamine, ethylhexylamine, nonylamine, decylamine, pyrrolidone, amino acids (lysine, arginine, alanine, glutamine, histidine, glycine), 2-amino-2-methyl-1-propanol, dimethylethanolamine, tris(hydroxymethyl)amino methane and combinations thereof.
6. A cosmetic patch or a towlette product containing a cosmetic composition according to any of claims 1 to 5.
7. A method for controlling signs of aging comprising:
providing a cosmetic composition comprising:
(i) from about 0.0001% to about 30% by weight of a salt of malonic acid;
(ii) from about 1% to about 99.9% by weight of a cosmetically acceptable carrier;
wherein the composition exhibits a Flexibility Value greater than 1 in the Porcine Skin Test; and applying the cosmetic composition to the skin.
7. A method for controlling signs of aging comprising:
providing a cosmetic composition comprising:
(i) from about 0.0001% to about 30% by weight of a salt of malonic acid;
(ii) from about 1% to about 99.9% by weight of a cosmetically acceptable carrier;
wherein the composition exhibits a Flexibility Value greater than 1 in the Porcine Skin Test; and applying the cosmetic composition to the skin.
7. The method according to claim 6 wherein the signs of aging that are controlled are softness, suppleness and flexibility.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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US38383702P | 2002-05-29 | 2002-05-29 | |
US60/383,837 | 2002-05-29 | ||
US45533003P | 2003-03-17 | 2003-03-17 | |
US60/455,330 | 2003-03-17 | ||
PCT/EP2003/005477 WO2003099254A1 (en) | 2002-05-29 | 2003-05-22 | Cosmetic compositions containing salts of malonic acid |
Publications (1)
Publication Number | Publication Date |
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CA2486905A1 true CA2486905A1 (en) | 2003-12-04 |
Family
ID=29587035
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Application Number | Title | Priority Date | Filing Date |
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CA002486905A Abandoned CA2486905A1 (en) | 2002-05-29 | 2003-05-22 | Cosmetic compositions containing salts of malonic acid |
Country Status (10)
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EP (1) | EP1509197A1 (en) |
JP (1) | JP2005531568A (en) |
KR (1) | KR20050007562A (en) |
CN (1) | CN1665479A (en) |
AR (1) | AR039908A1 (en) |
AU (1) | AU2003240709B2 (en) |
CA (1) | CA2486905A1 (en) |
MX (1) | MXPA04011904A (en) |
TW (1) | TW200404573A (en) |
WO (1) | WO2003099254A1 (en) |
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US20040202689A1 (en) * | 2003-03-17 | 2004-10-14 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Terpenoid fragrance components stabilized with malonic acid salts |
JP2006241021A (en) * | 2005-03-01 | 2006-09-14 | National Food Research Institute | Antiallergic agent |
WO2007089267A1 (en) * | 2006-02-03 | 2007-08-09 | Jr Chem, Llc | Anti-aging treatment using copper and zinc compositions |
US7897800B2 (en) * | 2006-02-03 | 2011-03-01 | Jr Chem, Llc | Chemical compositions and methods of making them |
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US4294852A (en) * | 1973-11-01 | 1981-10-13 | Johnson & Johnson | Skin treating compositions |
JPS60185710A (en) * | 1984-03-05 | 1985-09-21 | Kao Corp | Bath preparation of weak acidity |
US5218001A (en) * | 1984-03-19 | 1993-06-08 | The Rockefeller University | Inhibitors of the advanced glycosylation of proteins and methods of use therefor |
DE4321753A1 (en) * | 1993-06-30 | 1995-01-12 | Beiersdorf Ag | Deodorant cosmetics containing alpha,omega-alkanedicarboxylic acids |
JP3299054B2 (en) * | 1994-10-19 | 2002-07-08 | 花王株式会社 | Skin cosmetics |
JPH08268828A (en) * | 1995-03-31 | 1996-10-15 | Shiseido Co Ltd | Pack cosmetic |
AU6725496A (en) * | 1995-08-15 | 1997-03-19 | Robert Eric Montgomery | Peroxidase-activating oral compositions |
ES2199349T3 (en) * | 1996-03-14 | 2004-02-16 | Schering-Plough Healthcare Products, Inc. | COMPOSITION AND METHOD TO BRONZE WITHOUT SUN. |
JPH10175844A (en) * | 1996-10-18 | 1998-06-30 | Shiseido Co Ltd | Degradation promoter of desmosome |
EP0969089A1 (en) * | 1998-06-29 | 2000-01-05 | F. Hoffmann-La Roche Ag | Phytase formulation |
US6482423B1 (en) * | 1999-04-13 | 2002-11-19 | The Procter & Gamble Company | Antimicrobial wipes which provide improved residual benefit versus gram positive bacteria |
US20020061282A1 (en) * | 2000-10-11 | 2002-05-23 | Constantine Georgiades | Tooth whitening composition and method employing dicarboxylic acid whitening agent |
-
2003
- 2003-05-22 WO PCT/EP2003/005477 patent/WO2003099254A1/en not_active Application Discontinuation
- 2003-05-22 EP EP03730112A patent/EP1509197A1/en not_active Withdrawn
- 2003-05-22 JP JP2004506779A patent/JP2005531568A/en not_active Withdrawn
- 2003-05-22 CN CN03816020XA patent/CN1665479A/en active Pending
- 2003-05-22 AU AU2003240709A patent/AU2003240709B2/en not_active Ceased
- 2003-05-22 MX MXPA04011904A patent/MXPA04011904A/en unknown
- 2003-05-22 CA CA002486905A patent/CA2486905A1/en not_active Abandoned
- 2003-05-22 KR KR10-2004-7019166A patent/KR20050007562A/en not_active Application Discontinuation
- 2003-05-29 AR ARP030101893A patent/AR039908A1/en not_active Application Discontinuation
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EP1509197A1 (en) | 2005-03-02 |
TW200404573A (en) | 2004-04-01 |
AR039908A1 (en) | 2005-03-09 |
JP2005531568A (en) | 2005-10-20 |
MXPA04011904A (en) | 2005-03-31 |
KR20050007562A (en) | 2005-01-19 |
CN1665479A (en) | 2005-09-07 |
WO2003099254A1 (en) | 2003-12-04 |
AU2003240709A1 (en) | 2003-12-12 |
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