WO2000057893A1 - Compositions containing boswellia extracts - Google Patents
Compositions containing boswellia extracts Download PDFInfo
- Publication number
- WO2000057893A1 WO2000057893A1 PCT/GB2000/001114 GB0001114W WO0057893A1 WO 2000057893 A1 WO2000057893 A1 WO 2000057893A1 GB 0001114 W GB0001114 W GB 0001114W WO 0057893 A1 WO0057893 A1 WO 0057893A1
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- WO
- WIPO (PCT)
- Prior art keywords
- acid
- carbon atoms
- branched fatty
- branched
- composition according
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 94
- 239000000284 extract Substances 0.000 title claims abstract description 63
- 240000007551 Boswellia serrata Species 0.000 title claims description 59
- 235000018062 Boswellia Nutrition 0.000 title claims description 20
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 55
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 47
- 239000000194 fatty acid Substances 0.000 claims abstract description 47
- 229930195729 fatty acid Natural products 0.000 claims abstract description 47
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 40
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 19
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 19
- NBGQZFQREPIKMG-PONOSELZSA-N Boswellic acid Chemical compound C1C[C@@H](O)[C@](C)(C(O)=O)[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 NBGQZFQREPIKMG-PONOSELZSA-N 0.000 claims abstract description 16
- NBGQZFQREPIKMG-UHFFFAOYSA-N 3beta-hydroxy-beta-boswellic acid Natural products C1CC(O)C(C)(C(O)=O)C2CCC3(C)C4(C)CCC5(C)CCC(C)C(C)C5C4=CCC3C21C NBGQZFQREPIKMG-UHFFFAOYSA-N 0.000 claims abstract description 15
- 241001608538 Boswellia Species 0.000 claims abstract 7
- 239000002253 acid Substances 0.000 claims description 41
- 235000012035 Boswellia serrata Nutrition 0.000 claims description 30
- 239000004615 ingredient Substances 0.000 claims description 26
- 150000007513 acids Chemical class 0.000 claims description 23
- -1 fatty acid ester Chemical class 0.000 claims description 21
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 10
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 2
- 229940051250 hexylene glycol Drugs 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 3
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 14
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 14
- 229920002125 Sokalan® Polymers 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000006071 cream Substances 0.000 description 9
- 235000002639 sodium chloride Nutrition 0.000 description 9
- 239000000969 carrier Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 229960001631 carbomer Drugs 0.000 description 6
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 6
- 239000002304 perfume Substances 0.000 description 6
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 229960005150 glycerol Drugs 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 4
- 229920004511 Dow Corning® 200 Fluid Polymers 0.000 description 4
- 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 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229920001213 Polysorbate 20 Polymers 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 4
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 4
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- WAYINTBTZWQNSN-UHFFFAOYSA-N 11-methyldodecyl 3,5,5-trimethylhexanoate Chemical compound CC(C)CCCCCCCCCCOC(=O)CC(C)CC(C)(C)C WAYINTBTZWQNSN-UHFFFAOYSA-N 0.000 description 3
- JSOVGYMVTPPEND-UHFFFAOYSA-N 16-methylheptadecyl 2,2-dimethylpropanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C(C)(C)C JSOVGYMVTPPEND-UHFFFAOYSA-N 0.000 description 3
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000001914 calming effect Effects 0.000 description 3
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 3
- 229940073507 cocamidopropyl betaine Drugs 0.000 description 3
- 229940008099 dimethicone Drugs 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 3
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 3
- 229960002216 methylparaben Drugs 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- RHIIHYCQYFKTHL-UHFFFAOYSA-N n,n'-dihexadecyl-n,n'-bis(2-hydroxyethyl)propanediamide Chemical compound CCCCCCCCCCCCCCCCN(CCO)C(=O)CC(=O)N(CCO)CCCCCCCCCCCCCCCC RHIIHYCQYFKTHL-UHFFFAOYSA-N 0.000 description 3
- 229940055577 oleyl alcohol Drugs 0.000 description 3
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 3
- 229960005323 phenoxyethanol Drugs 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 3
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 3
- 229960003415 propylparaben Drugs 0.000 description 3
- 229920001285 xanthan gum Polymers 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- RMFFCSRJWUBPBJ-UHFFFAOYSA-N 15-hydroxypentadecyl benzoate Chemical compound OCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1 RMFFCSRJWUBPBJ-UHFFFAOYSA-N 0.000 description 2
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 description 2
- BOSXZNXZBFCZQM-UHFFFAOYSA-N 2-(2-hydroxypropoxy)propan-1-ol Chemical compound CC(O)COC(C)CO.CC(O)COC(C)CO BOSXZNXZBFCZQM-UHFFFAOYSA-N 0.000 description 2
- LNEXUGPWTFNCSO-UHFFFAOYSA-N 2-[(2-pyridin-1-ium-1-ylacetyl)amino]ethyl octadecanoate;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC(=O)OCCNC(=O)C[N+]1=CC=CC=C1 LNEXUGPWTFNCSO-UHFFFAOYSA-N 0.000 description 2
- DHVLDKHFGIVEIP-UHFFFAOYSA-N 2-bromo-2-(bromomethyl)pentanedinitrile Chemical compound BrCC(Br)(C#N)CCC#N DHVLDKHFGIVEIP-UHFFFAOYSA-N 0.000 description 2
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- 239000010677 tea tree oil Substances 0.000 description 1
- 229940111630 tea tree oil Drugs 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000004018 waxing Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229940043810 zinc pyrithione Drugs 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
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 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
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/32—Burseraceae (Frankincense family)
- A61K36/324—Boswellia, e.g. frankincense
-
- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
-
- 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
-
- 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
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/75—Anti-irritant
-
- 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
- A61Q19/004—Aftersun preparations
-
- 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
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q9/00—Preparations for removing hair or for aiding hair removal
- A61Q9/04—Depilatories
Definitions
- the invention relates to compositions comprising at least one Boswellia extract, or at least one boswellic acid or derivative thereof.
- the compositions are suitable for application to the skin or hair.
- Boswellia family of plants including Boswellia Serrata can produce a soothing effect to irritated skin and that this activity is due to the terpenoid compounds grouped under the general name 'boswellic acids' .
- the different boswellic acids share the same basic pentacyclic triterpene (steroid-like) structure but differ in their side groupings.
- EP-A-755,940 relates to a novel fraction and a process for the isolation of said fraction comprising a mixture of specified boswellic acids from the gum resin of Boswellia Serrata.
- the fraction is stated to exhibit anti-inflammatory, anti-arthritic and antiulcerogenic activity.
- Typical extracts of Boswellia plants are solids or powders with a wide melting range - normally above 80° C.
- an extract of Boswellia containing the boswellic acids, or boswellic acids or derivatives thereof themselves, need to be dissolved or dispersed in a suitable carrier. Although they can be dissolved in solvents such as methanol, ethyl acetate, acetone, and the like, these solvents are not suitable for use in typical skin and hair care formulations because of their aggressive solvent action on the skin and hair, and/or because of their high volatility and/or strong odour.
- Ingredients which are commonly used in skin care or hair care formulations such as glycerine, sorbitol, mineral oil, cyclomethicone, dimethicone and petrolatum are not suitable solvents or carriers for Boswellia extracts or boswellic acids or derivatives thereof as they are either too polar or not sufficiently polar.
- Alkalies can produce aqueous solutions of boswellic acids by forming the respective salts.
- alkaline products e.g. with a pH greater than 8.5
- prolonged skin or hair contact by alkaline products is not recommended, especially for sensitive skin or scalp, or for damaged hair.
- a specified group of fatty alcohols or fatty acids, or derivatives, or mixtures thereof are suitable carriers for dissolving and/or dispersing at least one Boswellia extract, or at least one boswellic acid or derivative thereof. Further, the carrier aids the incorporation of the extract, or acid, into compositions suitable for use on the skin or hair and improves the stability of said compositions containing the extract, or acid.
- composition suitable for use on the skin or hair comprising;
- a carrier selected from the group consisting of branched fatty alcohols containing 8 to 32 carbon atoms, branched fatty acids containing 8 to 32 carbon atoms, unsaturated fatty alcohols containing 12 to 24 carbon atoms, unsaturated fatty acids containing 12 to 24 carbon atoms, and derivatives of said branched fatty alcohols, said branched fatty acids, said unsaturated fatty alcohols and said unsaturated fatty acids, or mixtures thereof.
- a carrier selected from the group consisting of branched fatty alcohols containing 8 to 32 carbon atoms, branched fatty acids containing 8 to 32 carbon atoms, unsaturated fatty alcohols containing 12 to 24 carbon atoms, unsaturated fatty acids containing 12 to 24 carbon atoms, and derivatives of said branched fatty alcohols, said branched fatty acids, said unsaturated fatty alcohols and said unsaturated fatty acids, or mixtures thereof
- a carrier selected from the group consisting of branched fatty alcohols containing 8 to 32 carbon atoms, branched fatty acids containing 8 to 32 carbon atoms, unsaturated fatty alcohols containing 12 to 24 carbon atoms, unsaturated fatty acids containing 12 to 24 carbon atoms, and derivatives of said branched fatty alcohols, said branched fatty acids, said unsaturated fatty alcohols and said unsaturated fatty acids, or mixtures thereof,
- compositions suitable for application to the skin or hair are suitable for preparing compositions suitable for application to the skin or hair.
- compositions of the invention comprise at least one extract of a Boswellia plant, or at least one boswellic acid or derivative thereof.
- the compositions of the present invention suitably comprise a safe and effective amount, preferably from 0.005 % to 50% by weight of the composition and more preferably from 0.05% to 25% by weight of the composition of at least one Boswellia extract, or at least one boswellic acid or derivative thereof.
- Suitable extracts for use herein may be derived from the following Boswellia plants including Boswellia Carterii, Boswellia Frereana, Boswellia Bhau-dajaina, Boswellia Serrata and Boswellia Thurifera.
- the preferred plants from which extracts are derived are Boswellia Serrata.
- the extracts derived from Boswellia plants can comprise gums, oleo-gums, resins, essential oils and residues, or mixtures thereof.
- Preferred extracts for use herein are gums.
- Boswellia gum extract useful herein comprises a mixmre of active triterpenoid compounds more commonly known as boswellic acids. All boswellic acids have a pentacyclic structure based on 12-ursen-24-oic acid with differing substituents. Many individual boswellic acid compounds have been isolated from the Boswellia extract including - and ⁇ -boswellic acids and derivatives thereof. Of these, ⁇ -boswellic acid and derivatives thereof are thought to be the active components.
- a typical extract comprising Boswellia Serrata gum resin will comprise greater than 50% by weight boswellic acids and often more than 60% by weight boswellic acids.
- a typical extract of a Boswellia plant suitable for use herein comprises a mixture of boswellic acids comprising at least one of 3a-hydroxyurs-12-ene-24-oic acid, 3a- acetoxyurs-12-ene-24-oic acid, 3a-hydroxyurs-12-ene-l l-keto-24-oic acid and 3a- hydroxyurs-9.12-dien-24-oic acid.
- Boswellia extracts suitable for use herein are commercially available for example from Quest International, Kent, UK.
- the compositions of the invention also comprise a carrier for the at least one extract of a Boswellia plant, or the at least one boswellic acid or derivative thereof.
- suitable carriers for this purpose are selected from the group consisting of branched fatty alcohols containing 8 to 32 carbon atoms, branched fatty acids containing 8 to 32 carbon atoms, unsaturated fatty alcohols containing 12 to 24 carbon atoms, unsaturated fatty acids containing 12 to 24 carbon atoms, and derivatives of said branched fatty alcohols, said branched fatty acids, said unsaturated fatty alcohols and said unsaturated fatty acids, or mixtures thereof.
- compositions of the present invention typically comprise from 50% to 99.995% , preferably from 75% to 99.95% , and even more preferably from 80% to 95% of a carrier by weight of the composition.
- the preferred carriers for use herein are selected from branched fatty alcohols or branched fatty acids containing 8 to 32 carbon atoms, or mixtures thereof, which are liquids at room temperature.
- the branched fatty alcohols and fatty acids are saturated. Saturated compounds generally have good stability against oxidation. More preferred, are saturated, branched fatty alcohols or fatty acids containing from 8 to 20 carbon atoms.
- Particularly useful branched fatty alcohols and fatty acids herein include isostearyl alcohol, isostearic acid, isocetyl alcohol, isopalmitic acid, octyldodecanol, octyldecanol, hexyldecanol, butyloctanol and ethylhexanol.
- Unsaturated fatty alcohols and unsaturated fatty acids containing 12 to 24 carbon atoms which are liquid at room temperature are also good carriers for Boswellia extracts. However, their presence may be disadvantageous in compositions requiring long term storage because as they are unsaturated, they have the potential to become oxidised and rancid over time.
- Preferred for use herein are unsaturated fatty alcohols or unsaturated fatty acids containing from 16 to 20 carbon atoms. Particularly useful unsaturated alcohols and unsaturated acids herein include oleyl alcohol, oleic acid, linoleic acid and linolenic acid.
- Ethoxylated derivatives that are liquid at room temperature.
- Useful ethoxylated derivatives herein include derivatives of branched fatty alcohols or acids and derivatives of unsaturated fatty alcohols or acids.
- the number of ethylene oxide units per mole of fatty acid or fatty alcohol is in the range 1 to 15 and more preferably is in the range 1 to 10. It is also preferred that the derivative has a calculated HLB (hydrophilic / lipophilic balance) of less than 15 and preferably in the range 2 to 9.
- esters of the abovementioned branched, or unsaturated fatty acids the esters being liquid at room temperature.
- the fatty acids may be esterified with a wide variety of alcohols, including branched or linear, saturated or unsaturated alcohols.
- the fatty acid is esterified with an alcohol containing from 2 to 18 carbon atoms.
- Preferred esters for use herein are branched or unsaturated fatty acids esterified with a hexitol anhydride.
- the esters of hexitol anhydrides can be mono-, di- or tri-esters but are preferably mono-esters (i.e. the ratio of acid to hexitol anhydride is 1 : 1).
- a particularly preferred hexitol anhydride from which to prepare an ester is sorbitan.
- Other preferred esters are monoesters of glycerol and a branched fatty acid (monoglycerides of branched fatty acids).
- Monoglyceride compositions herein contain at least 80 per cent by weight of a monoglyceride of a single acid.
- Yet other preferred esters are monoesters of propylene glycol, butylene glycol, hexylene glycol or dipropylene glycol and a branched or an unsaturated fatty acid.
- esters of the branched fatty alcohols or unsaturated fatty alcohols the esters being liquid at room temperature.
- the fatty alcohols may be reacted with a wide variety of acids, including branched or linear, samrated or unsaturated acids and hydroxy acids such as ⁇ - hydroxy acids or ⁇ -hydroxy acids.
- the acid contains from 2 to 18 carbon atoms .
- (e) Ethoxylated derivatives of monoglycerides as defined in (b) above.
- the degree of ethoxylation is preferably from 1 to 15 ethylene oxide units per mole of monoglyceride and the ethoxylated monoglyceride is liquid at room temperature.
- the carriers used in the compositions of the invention are liquid at room temperature. However, it is not essential that the carrier should be completely free from solid matter. Since many available fatty alcohols and fatty acids comprise mixtures of alcohols or acids, certain isomers can be present as solid matter in the mixture. The presence of such solid matter is not detrimental to the use of a particular carrier, provided that the carrier is fluid at room temperature. For the purposes of assessing fluidity in relation to this invention a temperature of 23° C is assumed for "room temperature" .
- the carriers used in the compositions of the invention are capable of dispersing or dissolving the Boswellia extracts or boswellic acids or derivatives thereof. It is not essential that the extract or acid be completely soluble in the carrier, provided that the mixture of extract or acid and carrier can be incorporated into skin care or hair care products to produce a stable composition.
- the carrier of the present invention may also include other exicipients conventionally added to compositions suitable for application to the skin or hair such as, silicones, solvents such as water, emollients, or emulsifiers for example.
- exicipients conventionally added to compositions suitable for application to the skin or hair
- solvents such as water, emollients, or emulsifiers for example.
- compositions herein may comprise conventional ingredients normally present in compositions for application to the skin or hair.
- ingredients include alkanolamide surfactants, alkyl polyglucose derivatives, alkyl ether sulphate surfactants, allantoin, aloe barbadensis mil (aloe vera linne), ⁇ -hydroxycarboxylic acids, aluminium chlorhydrate and its derivatives, aluminium salts, amide derivatives, amino acids, amphoteric surfactants, ascorbic acid and its salts, bentonite and hectorite, benzyl alcohol, bisabolol, butane propellants, carboxy vinyl polymer water soluble salts, carboxy methylcellulose, carrageenan, cetrimonium salts, cholesterol, cocamidopropyl betaine, depilatories, dihydroxyacetone, dimethyl ether, ethanol, fatty acids, fatty acid citrate esters, fatty alcohols, fragrance ingredients, glucose esters of higher
- oil matter oligosaccharide(s), organic acids, pantothe ⁇ ic acid and its derivatives, petroleum jelly, phospholipid, polysaccharides eg locust bean gum, polyvinyl alcohol, polypeptides, proteins, piroctone olamine, quaternised silicone derivatives, raffinose, saponins, sodium chloride, sodium cocoyl isethionate, sodium hyaluronate, sources of linoleic acid, sterols, sterol esters, sucrose, sugar esters of higher fatty acids, sunscreens, surfactants, talc, tea tree oil (Melaleuca spp.), thioglycolic acid and its derivatives, titanium dioxide, tocopherol and esters thereof, triclosan, mono- or di- or triglycerides, vegetable oils, vitamins and analogues, volatile silicone fluids, water, water soluble moisture-retaining agents, water soluble polymers, waxes, zinc oxide, zinc pyri
- compositions of the present invention may be used in a wide range of products suitable for use on, or application to, the skin or hair particularly, but not exclusively, cosmetic compositions.
- Such products may be formulated in various product forms such as lotions, creams, gels, sticks, solutions, aerosols, solid soaps or liquid cleansers.
- the present invention provides a product for application to the skin or hair comprising a composition in accordance with the invention.
- 'skin' as used herein, means any outer surface of the body including the nails.
- composition of the invention can be separately prepared and added to the other ingredients of the desired product, or the compositions of the invention can be formed during the manufacture of the product.
- compositions according to the invention were prepared by mixing ingredients in the amounts listed below.
- Composition 1 Boswellia Serrata Gum Resin Extract 10% w/w Isostearyl Alcohol 90% w/w
- Composition 2 Boswellia Serrata Gum Resin Extract 15% w/w Isostearic Acid 85 % w/w
- composition 3 Boswellia Serrata Gum Resin Extract 5% w/w Oleic Acid 95% w/w
- composition 5 Boswellia Serrata Gum Resin Extract 5 % w/w Polyoxyethylene (3) isostearic acid 95% w/w Composition 6) Boswellia Serrata Gum Resin Extract 10% w/w Sorbitan monolaurate 90% w/w
- composition 7 Boswellia Serrata Gum Resin Extract 20% w/w
- Composition 8 Boswellia Serrata Gum Resin Extract 5% w/w Isopropyl isostearate 95 % w/w
- An Aftersun Cream Gelee was prepared according to the following formulation.
- Isostearyl alcohol Isostearyl Alcohol 1.35
- Phase B Deionised water (A) and hydroxypropylcellulose were combined and mixed under very high shear for 1 hour. Carbomer was added and left to wet out. Phase B was prepared by combining the ingredients with heating to 65° C and was then added to A with minimal shearing so as to avoid breaking down the structure. Phase C was prepared by combining the ingredients and added to the mixture of Phases A and B and the combined mixmre was stirred gently for 15 minutes.
- Boswellia Serrata extract helps to reduce redness and irritation and produces an even skin tone.
- An Acne Minimising Night Cream was prepared to the following formulation.
- Emcol E 607S Steapyrium chloride 3.50
- Phase B was prepared by combining the ingredients.
- Phase C was prepared by combining the ingredients and was added to Phase B using high shear.
- Phase A was prepared by combining the ingredients and this mixmre and Phase A were heated to 75 °C.
- Phase A was added to the mixmre using shear, and then cooled with stirring to 40 °C, when Phase D was added and stirred in thoroughly.
- An After Hair Removal Cream was prepared according to the following formulation.
- Phase C Triethanolamine 0.20 Phenonip Phenoxyethanol, methylparaben 0.50 Ethylparaben, propylparaben, butylparaben
- Phase A and Phase B were separately prepared by combining the ingredients and heated to 75 °C when Phase B was added to Phase A, and the triethanolamine was added. The emulsion was stirred until it was homogeneous and cooled. When the temperature reached 40°C, the preservative (Phenonip) and apricot extract and perfume were added and stirred in thoroughly.
- this cream prevents the appearance of red dots which usually appear after shaving as well as waxing or other ways of removing hair.
- a shampoo suitable for cleansing a baby's hair and scalp was prepared according to the following formulation:
- Isostearic acid Isostearic Acid 0.50
- Phase A was prepared by firstly dissolving with stirring the disodium EDTA and benzophenone-4 in water. The remaining ingredients of Phase A were then combined with this solution, stirring the mixmre between each addition.
- Phase B was prepared by combining the ingredients with heating to 65 °C. This mixture was then combined with Phase A. Perfume was then added to the mixmre of Phases A and B and the combined mixmre thickened upon the addition of sodium chloride.
- a hair shampoo suitable for frequent use was prepared according to the following formulation:
- Isostearic acid Isostearic Acid 0.40
- Phase A was prepared by dissolving the disodium EDTA in water with stirring. The remaining ingredients of Phase A were then combined with this solution, stirring the mixture between each addition.
- Phase B was prepared by combining the ingredients with heating to 65 °C. This mixmre was then combined with Phase A. Perfume was then added to the mixmre of Phases A and B and the combined mixture thickened upon the addition of sodium chloride.
- Boswellia Serrata extract helps to prevent and calm irritation caused by surfactants.
- a depilatory cream was prepared according to the following formulation.
- Isostearyl Alcohol Isostearyl Alcohol 1.80
- Phase B was prepared by combining the carbomer and dipropylene glycol with water and allowing the carbomer to wet out. Potassium thioglycolate (40%) was then carefully added to the hydrated polymer aqueous mixmre, followed by potassium hydroxide. Phase B was then heated to 65 °C.
- Phase A was separately prepared by combining all of the ingredients and heating to 65 °C. Phase A was then added to phase B using high shear mixing. The emulsion was stirred until it was homogeneous and cooled to room temperature. The pH of the resulting emulsion was then adjusted to 12.5 with the addition of a 20% solution of potassium hydroxide.
- this cream alleviates the appearance of red dots or rashes appearing on the skin following depilation with the alkaline cream.
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- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Microbiology (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
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- Mycology (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Medical Informatics (AREA)
- Pharmacology & Pharmacy (AREA)
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Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BRPI0009340-8B1A BR0009340B1 (en) | 1999-03-26 | 2000-03-23 | composition suitable for use on the skin or hair, product for application on the skin or hair, method of preparing a composition suitable for application on the skin or hair, and use of a composition. |
AT00912785T ATE243524T1 (en) | 1999-03-26 | 2000-03-23 | COMPOSITIONS CONTAINING BOSWELLIA EXTRACTS |
US09/913,952 US6589516B1 (en) | 1999-03-26 | 2000-03-23 | Compositions containing Boswellia extracts |
AU34432/00A AU3443200A (en) | 1999-03-26 | 2000-03-23 | Compositions containing boswellia extracts |
EP00912785A EP1165107B1 (en) | 1999-03-26 | 2000-03-23 | Compositions containing boswellia extracts |
DE60003537T DE60003537T2 (en) | 1999-03-26 | 2000-03-23 | COMPOSITIONS CONTAINING BOSWELLIA EXTRACTS |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9906914.8 | 1999-03-26 | ||
GBGB9906914.8A GB9906914D0 (en) | 1999-03-26 | 1999-03-26 | Compositions containing boswellia extracts |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000057893A1 true WO2000057893A1 (en) | 2000-10-05 |
Family
ID=10850354
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2000/001114 WO2000057893A1 (en) | 1999-03-26 | 2000-03-23 | Compositions containing boswellia extracts |
Country Status (8)
Country | Link |
---|---|
US (1) | US6589516B1 (en) |
EP (1) | EP1165107B1 (en) |
AT (1) | ATE243524T1 (en) |
AU (1) | AU3443200A (en) |
BR (1) | BR0009340B1 (en) |
DE (1) | DE60003537T2 (en) |
GB (1) | GB9906914D0 (en) |
WO (1) | WO2000057893A1 (en) |
Cited By (6)
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FR2819179A1 (en) * | 2001-01-11 | 2002-07-12 | Oreal | PHOTOPROTECTIVE COMPOSITIONS BASED ON AMPHIPHILIC POLYMERS |
WO2004082643A2 (en) * | 2003-03-20 | 2004-09-30 | Shiseido International France | Cosmetic composition |
NL1033954C2 (en) * | 2007-06-08 | 2008-12-09 | Otc Pharma Internat B V | Composition for shaving. |
ES2333639A1 (en) * | 2009-10-27 | 2010-02-24 | Cosmetica Cosbar S.L. | Protective composition of hair and scalp leather (Machine-translation by Google Translate, not legally binding) |
US8192768B2 (en) | 2007-04-03 | 2012-06-05 | Laila Impex | Synergistic anti-inflammatory and antioxidant dietary supplement compositions |
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EP1765761B1 (en) * | 2004-06-18 | 2013-04-03 | Laila Nutraceuticals | Novel analogs of 3-o-acetyl-11-keto-beta-boswellic acid |
US8748598B2 (en) | 2004-06-18 | 2014-06-10 | Laila Nutraceuticals | Analogs of 3-O-acetyl-11-keto-beta-boswellic acid |
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EP1736207A1 (en) * | 2005-06-23 | 2006-12-27 | Mibelle AG Cosmetics | Depilatory composition |
DE102006024911A1 (en) * | 2006-05-24 | 2007-11-29 | Aquanova Ag | Solubilizate of plant extract that contains active agent, useful as additive for e.g. cosmetics, pharmaceuticals and foods, includes water and emulsifier |
US20070048246A1 (en) * | 2005-09-01 | 2007-03-01 | Biophysica Research, Inc. | Novel skin care compositions |
FR2895238B1 (en) * | 2005-12-22 | 2011-04-01 | Oreal | USE OF A SORBITAN OXYALKYLENE ESTER FOR SOOTHING SCALP, AND METHOD FOR COSMETIC TREATMENT OF SCALP |
US20090053331A1 (en) * | 2007-08-21 | 2009-02-26 | Cook Colin W | Hands and feet sanitizing system |
CA2684258A1 (en) | 2009-11-03 | 2011-05-03 | Guy Chamberland | Compositions comprising plant extracts and methods of treating wounds, burns and skin injuries therewith |
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Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0755940A1 (en) * | 1995-04-13 | 1997-01-29 | Council of Scientific and Industrial Research | Boswellic acid compositions and preparation thereof |
-
1999
- 1999-03-26 GB GBGB9906914.8A patent/GB9906914D0/en not_active Ceased
-
2000
- 2000-03-23 EP EP00912785A patent/EP1165107B1/en not_active Expired - Lifetime
- 2000-03-23 AT AT00912785T patent/ATE243524T1/en active
- 2000-03-23 AU AU34432/00A patent/AU3443200A/en not_active Abandoned
- 2000-03-23 BR BRPI0009340-8B1A patent/BR0009340B1/en active IP Right Grant
- 2000-03-23 DE DE60003537T patent/DE60003537T2/en not_active Expired - Lifetime
- 2000-03-23 US US09/913,952 patent/US6589516B1/en not_active Expired - Lifetime
- 2000-03-23 WO PCT/GB2000/001114 patent/WO2000057893A1/en active IP Right Grant
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0755940A1 (en) * | 1995-04-13 | 1997-01-29 | Council of Scientific and Industrial Research | Boswellic acid compositions and preparation thereof |
Non-Patent Citations (2)
Title |
---|
DATABASE WPI Section Ch Week 199931, Derwent World Patents Index; Class A96, AN 1999-369936, XP002141933, QUEST INT UK LTD: "Use of Boswellia extracts, menthyl pyrrolidone carboxylate, ceramides and pongamol - are useful in e.g. cosmetics, food stuffs and pharmaceuticals" * |
RESEARCH DISCLOSURE, vol. 422, no. 034, 10 June 1999 (1999-06-10), Emsworth, GB * |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2819179A1 (en) * | 2001-01-11 | 2002-07-12 | Oreal | PHOTOPROTECTIVE COMPOSITIONS BASED ON AMPHIPHILIC POLYMERS |
WO2002055037A1 (en) * | 2001-01-11 | 2002-07-18 | L'oreal | Amphiphilic polymer-based photoprotective compositions |
US6955803B2 (en) | 2001-01-11 | 2005-10-18 | L'oreal | Photoprotective compositions comprising sulfonic/hydrophobic amphiphilic polymers |
WO2004082643A2 (en) * | 2003-03-20 | 2004-09-30 | Shiseido International France | Cosmetic composition |
WO2004082643A3 (en) * | 2003-03-20 | 2007-06-14 | Shiseido Int France | Cosmetic composition |
US8192768B2 (en) | 2007-04-03 | 2012-06-05 | Laila Impex | Synergistic anti-inflammatory and antioxidant dietary supplement compositions |
US8420132B2 (en) | 2007-04-03 | 2013-04-16 | Laila Impex | Synergistic anti-inflammatory and antioxidant dietary supplement compositions |
NL1033954C2 (en) * | 2007-06-08 | 2008-12-09 | Otc Pharma Internat B V | Composition for shaving. |
WO2008150155A2 (en) * | 2007-06-08 | 2008-12-11 | Otc Pharma International B.V. | Composition for shaving |
WO2008150155A3 (en) * | 2007-06-08 | 2010-03-04 | Otc Pharma International B.V. | Composition for shaving |
ES2333639A1 (en) * | 2009-10-27 | 2010-02-24 | Cosmetica Cosbar S.L. | Protective composition of hair and scalp leather (Machine-translation by Google Translate, not legally binding) |
WO2020174093A1 (en) * | 2019-02-28 | 2020-09-03 | Bic -Violex S.A. | Skin engaging member for razor cartridge comprising skin active ingredient |
Also Published As
Publication number | Publication date |
---|---|
AU3443200A (en) | 2000-10-16 |
GB9906914D0 (en) | 1999-05-19 |
DE60003537D1 (en) | 2003-07-31 |
ATE243524T1 (en) | 2003-07-15 |
BR0009340B1 (en) | 2013-08-27 |
EP1165107B1 (en) | 2003-06-25 |
US6589516B1 (en) | 2003-07-08 |
EP1165107A1 (en) | 2002-01-02 |
DE60003537T2 (en) | 2003-12-24 |
BR0009340A (en) | 2002-04-23 |
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