WO2008150263A1 - Esters de phosphate alcoxylés de beurre de karité - Google Patents
Esters de phosphate alcoxylés de beurre de karité Download PDFInfo
- Publication number
- WO2008150263A1 WO2008150263A1 PCT/US2007/013477 US2007013477W WO2008150263A1 WO 2008150263 A1 WO2008150263 A1 WO 2008150263A1 US 2007013477 W US2007013477 W US 2007013477W WO 2008150263 A1 WO2008150263 A1 WO 2008150263A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- shea butter
- weight
- alkoxylated phosphate
- mild
- phosphate ester
- Prior art date
Links
- 241001135917 Vitellaria paradoxa Species 0.000 title claims abstract description 62
- 235000018936 Vitellaria paradoxa Nutrition 0.000 title claims abstract description 62
- 229940057910 shea butter Drugs 0.000 title claims abstract description 60
- 150000003014 phosphoric acid esters Chemical class 0.000 title description 11
- -1 glycol phosphate esters Chemical class 0.000 claims abstract description 21
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 10
- 229910019142 PO4 Inorganic materials 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 239000010452 phosphate Substances 0.000 claims description 15
- 229940025703 topical product Drugs 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 15
- 238000012545 processing Methods 0.000 abstract description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 5
- 229920001451 polypropylene glycol Polymers 0.000 abstract description 5
- 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
- 150000001875 compounds Chemical class 0.000 description 11
- 150000002334 glycols Chemical class 0.000 description 11
- 235000006708 antioxidants Nutrition 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 235000014121 butter Nutrition 0.000 description 7
- 238000000605 extraction Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- 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
- 239000003153 chemical reaction reagent Substances 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
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 239000002904 solvent Substances 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
- 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
- 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
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000001697 butter ester Substances 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
- 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
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 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 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 238000005809 transesterification reaction Methods 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
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- 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
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-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
- 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
- 241000907903 Shorea 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
- 238000013019 agitation Methods 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
- 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
- 239000006071 cream 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
- OQMZNAMGEHIHNN-CIFIHVIMSA-N delta7-stigmasterol 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=C21 OQMZNAMGEHIHNN-CIFIHVIMSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 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
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 239000000499 gel Substances 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
- 239000006210 lotion Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000006072 paste Substances 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 241000894007 species Species 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 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
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 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
- A61K8/55—Phosphorus compounds
- A61K8/556—Derivatives containing from 2 to 10 oxyalkylene groups
-
- 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
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
Definitions
- the present invention relates to novel shea butter alkoxylated phosphate esters prepared by the reaction of shea butter, preferably mild-processed shea butter (MPSB), with polyoxyalkylene glycols, including polyoxyethylene glycol, polyoxypropylene glycol and mixtures thereof, followed by phosphation with a suitable phosphation reagent selected from the group consisting of polyphosphoric acid and P 2 O 5 .
- MPSB mild-processed shea butter
- Shea Butter is a butter extracted from the kernel of Butrospermum park ⁇ i. 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 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 1S group (oleyl) while R 1 and R 3 contain predominantly the saturated C ⁇ s 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.
- shea butter alkoxylated phosphate esters, and particularly MPSB alkoxylated phosphated esters, of the present invention typically contain from about 5% to about 15% by weight of unsaponifiables.
- the novel shea butter and MPSB alkoxylated phosphate esters of the present invention are produced by the transesterification of shea butter or MPSB with one or a combination of polyoxyalkylene glycols followed by phosphation.
- mion processed 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 (creating mild-processed shea butter) and during subsequent preparation of its alkoxylated phosphate derivatives.
- These processes result in materials containing unexpectedly high amounts unsaponifiables, notably antioxidants.
- the novel alkoxylated phosphate esters of the present invention are thus water-soluble emollients and emulsifiers that not only not only condition and soften skin and hair, but also deliver antioxidants (present in the unsaponifable fraction of mild-processed shea butter) in a heretofore unachievable manner.
- the compounds of the present invention are shea butter alkoxylated phosphate esters produced by a transesterification reaction of shea butter with polyoxyalkylene glycol compounds followed by phosphation of the resulting alkoxylate.
- the shea butter is mild-processed, and the reactions are conducted under specific mild-processing conditions.
- the novel alkoxylated phosphate esters of the present invention are rich in unsaponifiables, including antioxidants.
- the present invention relates to a novel class of alkoxylated phosphate esters made by reacting shea butter with polyoxyethylene glycol or polyoxypropylene glycol or mixtures thereof followed by phosphation of the resulting phosphate ester.
- the invention is also directed to a process for using the shea butter alkoxylated phosphate esters 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 unsaponif ⁇ ables, are produced.
- Shea butter (and MPSB) alkoxylated phosphate esters of the present invention conform to the following structure:
- R x is shea butter or, preferably mild-processed shea butter, which comprises from about 0.1% to about 2.0 % by weight Ci 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 1 5H 31 ; from about 25% to about 50% by weight Ci 7 H 35 ; from about 40% to about 60.0 % by weight C) 7 H 33 ; and a, b and c are independently integers ranging from 1 to 20; M is selected from the group consisting of H, Na and K.
- Another aspect of the present invention is a process for delivering antioxidants to the skin and hair by applying thereto a finished topical product comprising an effective amount of an alkoxylated phosphate ester made by an esterification reaction of shea butter, or preferably MPSB, and polyoxyalkylene glycol thereof that conforms to the following structure:
- R x is derived from shea butter, preferably mild-processed shea butter, which comprises from about 0.1% to about 2.0 % by weight CnH 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 QsH 3I ; from about 25% to about 50% by weight Ci 7 H 35 ; from about 40% to about 60.0 % by weight Ci 7 H 33 ; a, b and c are independently integers ranging from 1 to 20; and M is selected from the group consisting of H, Na and K.
- finished topical product is meant a cream, lotion, gel, foam, ointment, paste, emulsion, suspension, dispersion, solution, or similar topically-applied carrier or delivery system known to those of skill in the art.
- 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.
- 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%); delta-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! group. They are a class of natural products that possess antioxidant and free radical scavenging properties.
- phenolics in the unsaponifiables of mild-processed shea butter include gallic acid, gallocatchin, catechin, epigallocatechin gal late, epicatechin, gallocatechin gal late, gallocatechin gallate and quercetin.
- 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.
- 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 unsaponifiable (from about 7% to about 15% by weight) and may be used in making the MPSB polyoxyalkylene glycol esters of the present invention.
- Mild processing according to this aspect 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 strips off the desirable components is also to be avoided in processing MPSB of the present invention. By processing shea butter under mild conditions, materials comprising from about 5% to about 15% by weight of unsaponifiables can be produced.
- Polyoxyalkylene glycols are items of commerce and conform to the following structure:
- polyoxyalkylene glycol compounds is meant three different classes of compounds.
- Polyoxyethylene glycols are compounds in which "b” is zero;
- polyoxypropylene glycols are compounds in which "a” and "c” are zero and polyoxyalkylene glycols compounds in which "a” and/or "c" are not zero and "b” is not zero.
- Example 7 - 18 may be used in formulating finished cosmetic and personal care products without additional purification.
- Polyphosphoric acid (CAS No. 008017-16-1) and P 2 O 5 (CAS No. 1314-56-3) are articles of commerce well-known to persons of skill in the art. These reagents are reacted with the above- described alkoxylated shea butter (and MPSB) to produce the compounds of the present invention.
- the following examples are further illustrative of the phosphation step in creating the compounds of the present invention. 49 grams of polyphosphoric acid are added to the specified grams of the polyoxyalkylene glycol shea butter ester of Examples 7 - 18. The reaction mass is stirred well until homogeneous then heated to, 90 0 C for about 4 to 5 hours.
- the compounds of the present invention are effective surface active agents that provide emmoliency as well as mild detergency. They are well tolerated by the skin and eye and deliver antioxidants to the skin.
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Abstract
L'invention concerne de nouveaux esters de phosphate de polyoxyalkylène glycol préparés par la réaction de polyoxyéthylène glycol (PEG) ou de polyoxypropylène glycol (PPG) ou des mélanges de ces composés avec du beurre de karité, de préférence du beurre de karité légèrement transformé (MPSB), suivi d'une phosphatation dans des conditions de transformation modérées. Ces substances sont utiles comme ingrédients cosmétiques et de soins personnels, en permettant l'administration d'ingrédients actifs très souhaitables présents dans le beurre de karité, y compris des antioxydants naturels, sous une forme soluble dans l'eau qui est importante à la peau et aux cheveux.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2007/013477 WO2008150263A1 (fr) | 2007-06-08 | 2007-06-08 | Esters de phosphate alcoxylés de beurre de karité |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2007/013477 WO2008150263A1 (fr) | 2007-06-08 | 2007-06-08 | Esters de phosphate alcoxylés de beurre de karité |
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| Publication Number | Publication Date |
|---|---|
| WO2008150263A1 true WO2008150263A1 (fr) | 2008-12-11 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2007/013477 WO2008150263A1 (fr) | 2007-06-08 | 2007-06-08 | Esters de phosphate alcoxylés de beurre de karité |
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| WO (1) | WO2008150263A1 (fr) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6797836B1 (en) * | 2003-06-24 | 2004-09-28 | Zenitech Llc | Raspberry alkoxy esters as a delivery system for natural antioxidants |
| US7182940B1 (en) * | 2006-02-06 | 2007-02-27 | Rutherford Chemicals, Llc | Shea butter esters |
| US20070048241A1 (en) * | 2005-08-30 | 2007-03-01 | Croda, Inc. | Emulsifying system |
-
2007
- 2007-06-08 WO PCT/US2007/013477 patent/WO2008150263A1/fr active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6797836B1 (en) * | 2003-06-24 | 2004-09-28 | Zenitech Llc | Raspberry alkoxy esters as a delivery system for natural antioxidants |
| US20070048241A1 (en) * | 2005-08-30 | 2007-03-01 | Croda, Inc. | Emulsifying system |
| US7182940B1 (en) * | 2006-02-06 | 2007-02-27 | Rutherford Chemicals, Llc | Shea butter esters |
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