WO2008103138A1 - Esters de polyoxyalkylène-glycol de beurre de karité - Google Patents
Esters de polyoxyalkylène-glycol de beurre de karité Download PDFInfo
- Publication number
- WO2008103138A1 WO2008103138A1 PCT/US2007/004584 US2007004584W WO2008103138A1 WO 2008103138 A1 WO2008103138 A1 WO 2008103138A1 US 2007004584 W US2007004584 W US 2007004584W WO 2008103138 A1 WO2008103138 A1 WO 2008103138A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- shea butter
- weight
- polyoxyalkylene glycol
- mild
- glycol ester
- Prior art date
Links
- 241001135917 Vitellaria paradoxa Species 0.000 title claims abstract description 42
- 235000018936 Vitellaria paradoxa Nutrition 0.000 title claims abstract description 42
- 229940057910 shea butter Drugs 0.000 title claims abstract description 40
- 150000002334 glycols Chemical class 0.000 title abstract description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 25
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 17
- -1 polyoxyethylene Polymers 0.000 claims abstract description 16
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 19
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229940025703 topical product Drugs 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 abstract description 9
- 238000012545 processing Methods 0.000 abstract description 9
- 239000000203 mixture Substances 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 abstract description 4
- 239000004480 active ingredient Substances 0.000 abstract description 4
- 239000008406 cosmetic ingredient Substances 0.000 abstract description 2
- 239000013503 personal care ingredient Substances 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 235000014121 butter Nutrition 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 235000006708 antioxidants Nutrition 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 238000003306 harvesting Methods 0.000 description 3
- 229930014626 natural product Natural products 0.000 description 3
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- WMBWREPUVVBILR-GHTZIAJQSA-N (+)-gallocatechin gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-GHTZIAJQSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241001072282 Limnanthes Species 0.000 description 2
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound 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 2
- 150000005690 diesters Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000007760 free radical scavenging Effects 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- LVJJFMLUMNSUFN-UHFFFAOYSA-N gallocatechin gallate Natural products C1=C(O)C=C2OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C1OC(=O)C1=CC(O)=C(O)C(O)=C1 LVJJFMLUMNSUFN-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Natural products C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 description 1
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 description 1
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 description 1
- OSELKOCHBMDKEJ-UHFFFAOYSA-N (10R)-3c-Hydroxy-10r.13c-dimethyl-17c-((R)-1-methyl-4-isopropyl-hexen-(4c)-yl)-(8cH.9tH.14tH)-Delta5-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(=CC)C(C)C)C1(C)CC2 OSELKOCHBMDKEJ-UHFFFAOYSA-N 0.000 description 1
- MCWVPSBQQXUCTB-UHFFFAOYSA-N (24Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(=CC)C(C)C)CCC33)C)C3=CCC21 MCWVPSBQQXUCTB-UHFFFAOYSA-N 0.000 description 1
- HCXVJBMSMIARIN-ZETWWWAOSA-N 24alpha-Ethyl-koprostanol Natural products CC[C@H](C=C[C@H](C)[C@H]1CC[C@@H]2[C@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C)C(C)C HCXVJBMSMIARIN-ZETWWWAOSA-N 0.000 description 1
- MCWVPSBQQXUCTB-AMOSEXRZSA-N Delta7-Avenasterol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C MCWVPSBQQXUCTB-AMOSEXRZSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 240000006890 Erythroxylum coca Species 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 1
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
- 235000002290 Shorea stenoptera Nutrition 0.000 description 1
- 241001646710 Shorea stenoptera Species 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- JZVFJDZBLUFKCA-FXIAWGAOSA-N alpha-Spinasterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)CC[C@H]33)C)C3=CC[C@H]21 JZVFJDZBLUFKCA-FXIAWGAOSA-N 0.000 description 1
- FSLPMRQHCOLESF-UHFFFAOYSA-N alpha-amyrenol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C)C(C)C5C4=CCC3C21C FSLPMRQHCOLESF-UHFFFAOYSA-N 0.000 description 1
- FSLPMRQHCOLESF-SFMCKYFRSA-N alpha-amyrin Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C FSLPMRQHCOLESF-SFMCKYFRSA-N 0.000 description 1
- SJMCNAVDHDBMLL-UHFFFAOYSA-N alpha-amyrin Natural products CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CCC(O)CC5CCC34C)C2C1C SJMCNAVDHDBMLL-UHFFFAOYSA-N 0.000 description 1
- JZVFJDZBLUFKCA-UTQQLQBSSA-N alpha-spinasterol Natural products CC[C@H](C=C[C@H](C)[C@H]1CC[C@H]2C3=CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C JZVFJDZBLUFKCA-UTQQLQBSSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- MCWVPSBQQXUCTB-OQTIOYDCSA-N avenasterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)CC/C(=C/C)C(C)C)CC[C@H]33)C)C3=CC[C@H]21 MCWVPSBQQXUCTB-OQTIOYDCSA-N 0.000 description 1
- JFSHUTJDVKUMTJ-QHPUVITPSA-N beta-amyrin Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C JFSHUTJDVKUMTJ-QHPUVITPSA-N 0.000 description 1
- QQFMRPIKDLHLKB-UHFFFAOYSA-N beta-amyrin Natural products CC1C2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C)CCC1(C)C QQFMRPIKDLHLKB-UHFFFAOYSA-N 0.000 description 1
- PDNLMONKODEGSE-UHFFFAOYSA-N beta-amyrin acetate Natural products CC(=O)OC1CCC2(C)C(CCC3(C)C4(C)CCC5(C)CCC(C)(C)CC5C4=CCC23C)C1(C)C PDNLMONKODEGSE-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001697 butter ester Substances 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 235000008957 cocaer Nutrition 0.000 description 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 description 1
- 235000012734 epicatechin Nutrition 0.000 description 1
- 229940030275 epigallocatechin gallate Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005645 linoleyl group Chemical group 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229940032091 stigmasterol Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- 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
- A61K8/45—Derivatives containing from 2 to 10 oxyalkylene groups
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- 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
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
Definitions
- the present invention relates to novel shea butter polyoxyalkylene glycol esters prepared by the reaction of a polyoxyethylene glycol (PEG) or polyoxypropylene glycol (PPG) or mixtures thereof with shea butter, preferably mild-processed shea butter (MPSB) under specific mild-processing conditions.
- PEG polyoxyethylene glycol
- PPG polyoxypropylene glycol
- MPSB mild-processed shea butter
- Shea Butter is a butter extracted from the kernel of Butrospermum parkii. This plant, also referred to as Vitellaria paradoxa, is native to Africa.
- the term butter describes a material that is a solid at room temperature, but melts at about 40 0 C. Chemically, the butter is a triglyceride conforming to the following structure
- R 1 , R 2 and R 3 each have one of the following compositions: R Group Common Name Ran ⁇ e (%) Tv ⁇ ical (%)
- R 2 The average composition of R 2 is different than R 1 and R 3 , the latter two being similar.
- the R 2 moiety contains predominantly the unsaturated C, 8 group (oleyl) while R 1 and R 3 contain predominantly the saturated Cis group (stearyl). Differences between internal (R 2 ) and terminal (R 1 , R 3 ) substitution are seen in natural products but not in synthetic molecules produced in the laboratory.
- the novel polyoxyalkylene ester compounds of the present invention are produced by reacting shea butter (preferably MPSB under specific mild conditions) with polyoxyethylene glycol (PEG) or polyoxypropylene glycol (PPG) or mixtures thereof.
- shea butter preferably MPSB under specific mild conditions
- PEG polyoxyethylene glycol
- PPG polyoxypropylene glycol
- mild processing is meant processes that do not remove or otherwise diminish the amount or potency of active ingredients, particularly highly desired unsaponifiables.
- mild processing is employed both at the time of harvesting and initial extraction and during subsequent preparation of derivatives. These mild processes result in materials containing unexpectedly high amounts unsaponifiables, notably antioxidants.
- polyoxyalkylene glycol esters are known in the art. Monoesters as well as saturated, unsaturated and Guerbet diesters are commercially available. Differing hydrophile-lipophile balances (HLB) and melting points can be achieved by varying one or both of the length of the carbon chain in the fatty source and the molecular weight of the poloxyakylene group.
- HLB hydrophile-lipophile balances
- the HLB of lauric acid (Ci 2 ) diesters of PEG can vary from about 6 to about 18, where the molecular weights of the poloxyethylene glycol (the hydrophilic portion of the surfactant) ranges from PEG-200 to PEG-4000.
- PEG esters perform several functions, providing emulsification, acting as emollients and solubilizing fragrance oils.
- U.S. Patent 5,917,070 teaches polyoxyalkylene glycol esters prepared by the reaction of polyoxyalkylene glycol with Meadowfoam oil as a triglyceride, as a fatty acid or as a methyl ester. The compounds are said to have good oxidative stability related to the specific carbon chain distribution of Meadowfoam oil.
- the polyoxyalkylene glycol esters described in the '070 Patent do not possess the desirable unsaponif ⁇ able fractions, and with them antioxidant properties, of the compounds of the present invention. Summary of the Invention
- the compounds of the present invention are shea butter esters produced by reacting mild-process shea butter with polyoxyalkylene glycols.
- the shea butter is mild-processed and the reaction with the polyoxyalkylene glycols is under mild conditions.
- the novel compounds of the present invention are rich in unsaponif ⁇ ables, including antioxidants.
- the present invention relates to a novel class of polyoxyalkylene esters — namely
- PEG esters, PPG esters and PEG/PPG esters made by reacting shea butter with polyoxyethylene glycol or polyoxypropylene glycol or mixtures thereof and a process for using them in personal care applications.
- mild processing is employed both at the time of harvesting and initial extraction and during subsequent preparation of alkoxylate derivatives. In so doing, materials containing unexpectedly high amounts of active ingredients, particularly highly desired unsaponifiables, are produced.
- Shea butter polyoxyalkylene glycol esters of the present invention conform to the following structure:
- R is derived from shea butter and comprises from about 0.1 to about 2.0 % by weight C) iH 23 ; from about 0.5 to about 2.0% by weight Ci 3 H 27 ; from about 2.0 to about 6.0% by weight C 15 H 31 ; from about 25 to about 50% by weight Ci 7 H 3S ; from about 40.0 to about 60.0 % by weight C 17 H 33 ; and (ii) a, b and c are independently integers ranging from 1 to 20.
- Another aspect of the invention is a process for delivering antioxidants to the skin and hair by applying thereto a finished topical product comprising an effective concentration of a shea butter polyoxyalkylene ester that is made by an esterification reaction and conforms to the structure:
- R is derived from shea butter and comprises from about 0.1 to about 2.0 % by weight CnH 23 ; from about 0.5 to about 2.0% by weight C) 3 H 27 ; from about 2.0 to about 6.0% by weight CisH 3] ; from about 25 to about 50% by weight C
- the esterification is conducted at a temperature of from about 180 0 C to about 190 0 C .
- the effective concentration of MPSB polyoxyalkylene glycol ester is from about 0.5% to about 15.0% by weight of the total weight of the finished formulation.
- Shea butter can be prepared by standard extraction techniques known to those of skill in the art.
- U.S. Patent No. 6,552,208 the disclosure of which is incorporated herein by reference, describes several methods for processing shea butter.
- Suitable extraction vehicles may include, but are not limited to, ethanol, methanol, ethyl acetate, acetone, chloroform and water, or any other solvent and water.
- shea butter is mild-processed; it is extracted using a hydrocarbon-free solvent system and its polyoxyalkylene ester derivatives of the present invention are made under mild processing conditions.
- ground-up kernels are boiled in water under mild conditions as described in the example below.
- the oil phase is then separated from the water phase by decanting. This process provides a yellow, solid wax rich in unsaponifiables.
- wax is meant a material obtained by boiling in water under ambient conditions, decanted and filtered.
- the mild processing of the present invention may be contrasted with separation using solvents and high temperature treatment with high pressure steam. While the latter processes result in what some may describe as a "more pure" triglyceride, unsaponifiables, and the benefits derived therefrom, are lost. Vacuum distillation which s.trips off the desirable components is also to be avoided in processing MPSB of the present invention.
- materials comprising from about 5% to about 15% by weight of unsaponifiables can be produced.
- Sterols comprise about 20% of the unsaponifiables in shea butter.
- the sterols comprise: cholesterol (from about 1% to about 3%); alpha- spinasterol (from about 1 % to about 4%); deIta-7-stigmasterol (from about 40% to about 44%); delta-7-avenasterol (from about 38% to about 41%).
- the remaining constituents of the unsaponifiables (about 80%) include other highly desirable active compounds including tocopherol, karitin, cinamic acid esters, alpha and beta amyrin and phenolics.
- Phenolic compounds are natural products composed of one or more aromatic benzene rings with one or more hydroxy 1 group. They are a class of natural products that possess antioxidant and free radical scavenging properties.
- phenolics in the unsaponif ⁇ ables of mild-processed shea butter include gallic acid, gallocatchin, catechin, epigallocatechin gallate, epicatechin, gallocatechin gallate, gallocatechin gallate and quercetin.
- Polyoxyalkylene glycols are an item of commerce and conform to the following structure:
- the starting MPSB is made according to following procedure: 500.0 grams of the nut form the Shea Butter tree are cracked into small pieces and placed into a one-liter vat of water. The water is then heated to 100 0 C. As the temperature increases, an oil phase develops on the surface of the water. The temperature is held for about 2 hours, after which the oil is decanted and passed through filter paper.
- the resulting butter is mild- processed shea butter according to the present invention. It is rich in unsaponif ⁇ able (from about 7% to about 15% by weight) and may be used in making the MPSB polyoxyalkylene glycol esters of the present invention.
- Poloxyalkylene glycols as described in Examples 1 - 6 are reacted with MPSB as follows: To 145.0 grams of the mild process shea butter are added the number of grams of polyoxyalkylene glycols in Examples 7 — 18. Using a reflux condenser, the temperature of the mass is raised to 18O 0 C - 190 0 C. The mass is held within this temperature range for 10 hours. None is distilled off during this time, and the reaction mass becomes hazy. The reaction mass is cooled, glycerin separates off and is removed from the bottom. The products of Example 7 - 18 may be used in formulating finished cosmetic and personal care products without additional purification. imple Polyoxyalkylene Glycol Grams
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Abstract
L'invention concerne de nouveaux esters de polyoxyalkylène glycol préparés par réaction d'un polyoxyéthylène glycol (PEG) ou d'un polyoxypropylène glycol (PPG), ou de mélanges de ceux-ci, avec du beurre de karité, de préférence du beurre de karité transformé par des techniques douces (MPSB: mild processed shea butter), dans des conditions spécifiques de transformation faisant appel à des techniques douces. Ces matières sont utiles en tant qu'ingrédients cosmétiques et de soins personnels, et permettent de fournir des principes actifs de haute valeur contenus dans le beurre de karité, notamment d'anti-oxydants naturels, sous une forme hydrosoluble substantive pour la peau et les cheveux.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2007/004584 WO2008103138A1 (fr) | 2007-02-23 | 2007-02-23 | Esters de polyoxyalkylène-glycol de beurre de karité |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2007/004584 WO2008103138A1 (fr) | 2007-02-23 | 2007-02-23 | Esters de polyoxyalkylène-glycol de beurre de karité |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2008103138A1 true WO2008103138A1 (fr) | 2008-08-28 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2007/004584 WO2008103138A1 (fr) | 2007-02-23 | 2007-02-23 | Esters de polyoxyalkylène-glycol de beurre de karité |
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| Country | Link |
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| WO (1) | WO2008103138A1 (fr) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994018292A1 (fr) * | 1993-02-11 | 1994-08-18 | The Procter & Gamble Company | Compositions d'hygiene corporelle |
| WO2005016309A1 (fr) * | 2003-08-11 | 2005-02-24 | Rovi Gmbh & Co. Kosmetische Rohstoffe Kg | Composition cosmetique favorisant le transport d'oxygene dans la peau |
| US7179494B1 (en) * | 2006-01-20 | 2007-02-20 | Marche Image Corp. | Composition and method for reducing incidents of hot flashes in females |
-
2007
- 2007-02-23 WO PCT/US2007/004584 patent/WO2008103138A1/fr active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994018292A1 (fr) * | 1993-02-11 | 1994-08-18 | The Procter & Gamble Company | Compositions d'hygiene corporelle |
| WO2005016309A1 (fr) * | 2003-08-11 | 2005-02-24 | Rovi Gmbh & Co. Kosmetische Rohstoffe Kg | Composition cosmetique favorisant le transport d'oxygene dans la peau |
| US7179494B1 (en) * | 2006-01-20 | 2007-02-20 | Marche Image Corp. | Composition and method for reducing incidents of hot flashes in females |
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