WO2000032153A1 - Microemulsion compositions - Google Patents
Microemulsion compositions Download PDFInfo
- Publication number
- WO2000032153A1 WO2000032153A1 PCT/GB1999/004053 GB9904053W WO0032153A1 WO 2000032153 A1 WO2000032153 A1 WO 2000032153A1 GB 9904053 W GB9904053 W GB 9904053W WO 0032153 A1 WO0032153 A1 WO 0032153A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- fragrance
- surfactant
- hydrolases
- cores
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 89
- 239000004530 micro-emulsion Substances 0.000 title claims abstract description 55
- 239000003205 fragrance Substances 0.000 claims abstract description 106
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 58
- 230000000694 effects Effects 0.000 claims abstract description 35
- 239000000693 micelle Substances 0.000 claims abstract description 32
- 230000001965 increasing effect Effects 0.000 claims abstract description 14
- 239000002781 deodorant agent Substances 0.000 claims abstract description 7
- 239000002537 cosmetic Substances 0.000 claims abstract description 5
- 239000004094 surface-active agent Substances 0.000 claims description 54
- 239000003623 enhancer Substances 0.000 claims description 38
- 102000004157 Hydrolases Human genes 0.000 claims description 32
- 108090000604 Hydrolases Proteins 0.000 claims description 32
- 102000004190 Enzymes Human genes 0.000 claims description 23
- 108090000790 Enzymes Proteins 0.000 claims description 23
- 229940088598 enzyme Drugs 0.000 claims description 23
- 239000003921 oil Substances 0.000 claims description 23
- 239000002243 precursor Substances 0.000 claims description 18
- 239000002304 perfume Substances 0.000 claims description 16
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
- 229930182470 glycoside Natural products 0.000 claims description 14
- -1 mustard oil glycoside Chemical class 0.000 claims description 12
- 108091005804 Peptidases Proteins 0.000 claims description 10
- 102000035195 Peptidases Human genes 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000002338 glycosides Chemical class 0.000 claims description 8
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 claims description 7
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 claims description 7
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 claims description 7
- 238000012856 packing Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 230000036571 hydration Effects 0.000 claims description 6
- 238000006703 hydration reaction Methods 0.000 claims description 6
- 235000019833 protease Nutrition 0.000 claims description 6
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 5
- 108010010803 Gelatin Proteins 0.000 claims description 5
- 239000008273 gelatin Substances 0.000 claims description 5
- 229920000159 gelatin Polymers 0.000 claims description 5
- 235000019322 gelatine Nutrition 0.000 claims description 5
- 235000011852 gelatine desserts Nutrition 0.000 claims description 5
- 125000003147 glycosyl group Chemical group 0.000 claims description 5
- 239000000787 lecithin Substances 0.000 claims description 5
- 235000010445 lecithin Nutrition 0.000 claims description 5
- 229940067606 lecithin Drugs 0.000 claims description 5
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000499 gel Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000001593 sorbitan monooleate Substances 0.000 claims description 4
- 235000011069 sorbitan monooleate Nutrition 0.000 claims description 4
- 229940035049 sorbitan monooleate Drugs 0.000 claims description 4
- 125000004383 glucosinolate group Chemical group 0.000 claims description 3
- 239000008187 granular material Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000008164 mustard oil Substances 0.000 claims description 3
- 229940066734 peptide hydrolases Drugs 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 2
- 108090000194 Dipeptidyl-peptidases and tripeptidyl-peptidases Proteins 0.000 claims description 2
- 102000003779 Dipeptidyl-peptidases and tripeptidyl-peptidases Human genes 0.000 claims description 2
- 108700035782 EC 3.4.3.- Proteins 0.000 claims description 2
- 241000282326 Felis catus Species 0.000 claims description 2
- 239000005792 Geraniol Substances 0.000 claims description 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 2
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 2
- 206010021639 Incontinence Diseases 0.000 claims description 2
- 102000004195 Isomerases Human genes 0.000 claims description 2
- 108090000769 Isomerases Proteins 0.000 claims description 2
- 102000003960 Ligases Human genes 0.000 claims description 2
- 108090000364 Ligases Proteins 0.000 claims description 2
- 102000004316 Oxidoreductases Human genes 0.000 claims description 2
- 108090000854 Oxidoreductases Proteins 0.000 claims description 2
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 claims description 2
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 claims description 2
- 102000004357 Transferases Human genes 0.000 claims description 2
- 108090000992 Transferases Proteins 0.000 claims description 2
- 239000002386 air freshener Substances 0.000 claims description 2
- 230000001166 anti-perspirative effect Effects 0.000 claims description 2
- 239000003213 antiperspirant Substances 0.000 claims description 2
- 102000005936 beta-Galactosidase Human genes 0.000 claims description 2
- 108010005774 beta-Galactosidase Proteins 0.000 claims description 2
- 102000006995 beta-Glucosidase Human genes 0.000 claims description 2
- 108010047754 beta-Glucosidase Proteins 0.000 claims description 2
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 235000000484 citronellol Nutrition 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 239000002979 fabric softener Substances 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- 229940113087 geraniol Drugs 0.000 claims description 2
- 150000002314 glycerols Chemical class 0.000 claims description 2
- 150000002327 glycerophospholipids Chemical class 0.000 claims description 2
- 229940041616 menthol Drugs 0.000 claims description 2
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 2
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 2
- 150000003904 phospholipids Chemical class 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 150000003505 terpenes Chemical class 0.000 claims description 2
- 235000007586 terpenes Nutrition 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 108010058651 thioglucosidase Proteins 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 239000000443 aerosol Substances 0.000 claims 2
- 238000009991 scouring Methods 0.000 claims 2
- 241000271915 Hydrophis Species 0.000 claims 1
- 102000005741 Metalloproteases Human genes 0.000 claims 1
- 108010006035 Metalloproteases Proteins 0.000 claims 1
- 239000004902 Softening Agent Substances 0.000 claims 1
- 238000004378 air conditioning Methods 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 239000008266 hair spray Substances 0.000 claims 1
- 239000006210 lotion Substances 0.000 claims 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 1
- 235000019341 magnesium sulphate Nutrition 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 239000003380 propellant Substances 0.000 claims 1
- 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 claims 1
- 239000000454 talc Substances 0.000 claims 1
- 229910052623 talc Inorganic materials 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000012459 cleaning agent Substances 0.000 abstract description 4
- 239000012071 phase Substances 0.000 description 13
- INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 9
- 238000009472 formulation Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 3
- 108010031186 Glycoside Hydrolases Proteins 0.000 description 3
- 102000005744 Glycoside Hydrolases Human genes 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000012437 perfumed product Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical compound CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000002532 enzyme inhibitor Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 229940043353 maltol Drugs 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 108010051152 Carboxylesterase Proteins 0.000 description 1
- 102000013392 Carboxylesterase Human genes 0.000 description 1
- 108090000317 Chymotrypsin Proteins 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108010056771 Glucosidases Proteins 0.000 description 1
- 102000004366 Glucosidases Human genes 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 108010058834 acylcarnitine hydrolase Proteins 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229960002376 chymotrypsin Drugs 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002474 experimental method Methods 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
- 235000013305 food Nutrition 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000007908 nanoemulsion Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 238000010587 phase diagram Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01K—ANIMAL HUSBANDRY; AVICULTURE; APICULTURE; PISCICULTURE; FISHING; REARING OR BREEDING ANIMALS, NOT OTHERWISE PROVIDED FOR; NEW BREEDS OF ANIMALS
- A01K1/00—Housing animals; Equipment therefor
- A01K1/015—Floor coverings, e.g. bedding-down sheets ; Stable floors
- A01K1/0152—Litter
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0291—Micelles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/068—Microemulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/01—Deodorant compositions
- A61L9/012—Deodorant compositions characterised by being in a special form, e.g. gels, emulsions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
- C11D17/0017—Multi-phase liquid compositions
- C11D17/0021—Aqueous microemulsions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2041—Dihydric alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/3427—Organic compounds containing sulfur containing thiol, mercapto or sulfide groups, e.g. thioethers or mercaptales
Definitions
- the present invention relates to fragrance-releasing compositions for use in a wide range of products, including perfumery products, laundry compositions, deodorants, cleaning agents, cosmetics and toiletries.
- the present invention relates to compositions comprising water-in-oii microemulsion droplets and/or hydrated reverse micelles dispersed in an anhydrous carrier, wherein the droplet/micelle cores have low water activity and contain a latent fragrance which is activated when the water activity within the cores is increased.
- Fragrances are presently employed in industry in a wide range of products, either as principal functional components (e.g. in perfumes) or as adjuncts to impart a sensorial dimension to the quality of other products. In either case, major difficulties arise from the fact that many fragrances are labile and/or volatile (and so fugitive) . Accordingly, there is considerable interest in means for stabilizing and/or providing for controlled release of fragrances.
- fragrances exist as fragrance precursors which are more stable than the active fragrance itself.
- fragrances especially from plant oils
- glycoside precursors which are much more stable than the fragrance aglycone, but are odourless.
- fragrance delivery systems based on the use of stable fragrance precursors which are activated during use or when required obviates the need for stabilized fragrances, so overcoming the problems associated with fugitive fragrances.
- microemulsion technology (vide infra) can be exploited to stably maintain fragrance precursors prior to use while permitting controlled release of active fragrance moieties derived from the precursors when required and on hydration.
- fragrance enhancers have also been recognized that the problems associated with fugitive fragrances can be addressed through the use of fragrance enhancers.
- Fragrance enhancers many of which are Maillard volatiles, such as furaneol and maltol
- many known fragrance enhancers are themselves highly labile, so limiting their utility in perfumed products.
- many fragrance enhancers also exist as precursors which are much more stable than the enhancer per se (for example, many fragrance enhancers exist as glycoside precursors which are much more stable than the active aglycone).
- the present inventors have therefore also applied microemulsion technology to stably maintain fragrance enhancer precursors in various compositions so that active enhancer can be rapidly released when required to intensify the aroma of other fragrances present in the composition.
- Microemulsions are systems of oil, water and surfactant which exist as single phase liquid solutions that are optically isotropic and thermodynamically stable (Danielsson and Lindmann ( 1 981 ), Colloids Surfaces 3, pp. 391 et seq.) .
- Microemulsions therefore differ fundamentally from emulsions, which are simply ⁇ roplet dispersions of one liquid in another (oil in water or water in oil). As such, emulsions are thermodynamically unstable and ultimately separate into distinct oil and water phases as droplet coalescence and coagulation occurs.
- microemulsion has also been used by those skilled in the art to define compositions comprising very small droplets in a medium, the droolets usually having diameters in the nm size range (and so also referred to as “nanodroplets " or “nanoemulsions ”)
- microemulsion is intended to embrace compositions falling within the scope of both of the definitions set out above .
- microemulsions The structure, properties and known uses of microemulsions is reviewed in Rees and Robinson ( 1 993), Adv Mater 5(9), pp 608-61 9, the disclosure of which relating to the structure of microemulsions and organogels is incorporated herein by reference.
- FIG. 1 The extent and position of the single phase microemulsion region for a typical surfactant (or combination of surfactants) is shown in the schematic phase diagram ( Figure 1); wherein, 1 is liquid crystal (lamellar); 2 is a water-in-oil microemulsion; 3 is a reverse micelle; 20 is oil; 6 is 2 phase; 30 is water; 4 is a micelle; 5 is an oil-in- water microemulsion and 10 is a surfactant.
- Figure 1 liquid crystal (lamellar); 2 is a water-in-oil microemulsion; 3 is a reverse micelle; 20 is oil; 6 is 2 phase; 30 is water; 4 is a micelle; 5 is an oil-in- water microemulsion and 10 is a surfactant.
- the parameter R and the surfactant concentration define the composition.
- R is the mole ratio of water to surfactant (Eq. 1 ) .
- the droplets are relatively small and the amount of water present is only just sufficient to fully hydrate the surfactant head groups and counterions. Under these circumstances, the
- Microemulsions in the form of droplets are essentially monodisperse, the droplets having radii within the range 1 -1 00 nm (more usually, 1 - 1 0 nm).
- Microemulsion surfactants and co-surfactants are Microemulsion surfactants and co-surfactants
- Microemulsion formation is dependent on the presence of amphiphilic surfactant molecules having both polar and non-polar regions which stabilize the oil- water interface.
- co-surfactants are also required to act as spacers and maintain the spacing between charged headgroups (so minimizing coulombic repulsions) .
- V is the effective packing volume of the surfactant hydrocarbon tail
- / is the length of the hydrocarbon tail
- a is the ef ective headgroup area at the oil-water interface.
- microemulsions are technically trivial and the preparation of many different microemulsion compositions has been described in detail in the prior art.
- the surfactant is first dissolved in the oil and then water is added with gentle shaking. This procedure generally results in the formation of an optically-clear single-phase solution containing microemulsion droplets. Heating or sonication (e.g. in sonicating water baths) is not necessary to achieve the single- phase dispersion, though such steps may be employed where convenient to facilitate preparation.
- Winsor 1 948) ; Trans. Faraday Soc , 44: page 376.
- an oil-in-water microemulsion may co-exist with an oil phase (Winsor I), or a water-in-oil microemulsion may co-exist with excess water (Winsor II) .
- Winsor III also possible is a Winsor III system, which forms when the surfactant is concentrated in a surfactant-rich middle phase which co-exists with oil and water phases containing low concentrations of droplets (water-in-oil and oil-in-water, respectively).
- Winsor I to Winsor II interconversion can be induced by changing the temperature or ionic strength of the microemulsion composition or through the addition of co-surfactants.
- the ability to effect such interconversions has great utility in microemulsion-based synthetic systems, since phase interconversion provides a simple means of separating water-soluble products from surfactant (Winsor II) as well as oil-soluble species from surfactant (Winsor I).
- enzymes can be solubilized in the droplet cores of w/o microemulsion droplets with retention of activity and stability.
- a large number of enzymes have been solubilized in this way (see Rees and Robinson, infra).
- the resultant systems are essentially a single phase, they can assimilate both water-insoluble and water-soluble substrates.
- Microemulsion systems containing solubilized enzymes have also been used in organic synthesis, and syntheses on the preparative scale have been reported with hydrolases such as chymotrypsin and Iipase (see Rees and Robinson, op at) These synthetic systems have been used to produce esters from alcoholic and fatty acid precursors for use in the food industry (West ( 1 988) , Chem Br (Dec) p 1 220)
- MSGs microemulsion-based organogels
- MBGs may be easily prepared by incubating the parent microemulsion at 50°C and mixing with a solution of gelatin in water at the same temperature. The resulting mixture is then shaken vigorously and allowed to cool, whereupon an optically transparent single phase gel is formed. Gel strength is controlled by varying the amount of gelatin present.
- a composition e.g. a fragrance releasing composition
- a composition comprising water-in-oil microemulsion droplets and/or hydrated reverse micelles dispersed in an anhydrous carrier, wherein the droplet/micelle cores have low water activity and contain a latent fragrance or latent fragrance enhancer which is activated when the water activity within the cores is increased
- the latent fragrance may comprises a system comprising a fragrance/fragrance enhancer precursor and an enzyme which is inactive due to the low water activity within the cores, wherein the enzyme acts on the fragrance precursor to produce an active fragrance/fragrance enhancer moiety on hydration of the cores.
- anhydrous is used to define carriers (which may be in the solid, gaseous, liquid or polyphasic state) which have a water activity low enough to prevent activation of the latent fragrance.
- the term is intended to define a water activity within the cores which is insufficient to permit significant catalysis. Thus, the term does not necessarily imply an absolute absence of water.
- fragrance enhancer is a term of art used to define any of a variety of agents which synergise with other fragrances and so intensify their odour.
- One important class of fragrance enhancers is the Maiilard volatiies, which include altol and furaneol and their analogues which occur naturally or which can be formed by e.g. caramelization.
- Fragrance enhancers find particular application in circumstances where it is desired to increase the intensity or permanence of one or more selected labiie and/or volatile fragrances. In such embodiments, this is achieved by providing the labile and/or volatile fragrance(s) (hereinafter referred to as the "co-fragrance(s) ”) in admixture with a composition according to the invention which comprises water- in-oil microemulsion droplets and/or hydrated reverse micelles dispersed in an anhydrous carrier, wherein the droplet/micelle cores have low water activity and contain a latent fragrance enhancer which is activated when the water activity within the cores is increased.
- the activated fragrance enhancer acts in synergy with the co-fragrance(s), so increasing their intensity and/or persistence.
- the invention finds particular application in a method for increasing the intensity and/or permanence of a fragrance comprising the step of mixing the fragrance with a composition comprising water-in-oil microemulsion droplets and/or hydrated reverse micelles to produce an anhydrous mixture, wherein the droplet/micelle cores have low water activity and contain a latent fragrance enhancer which is activated when the water activity within the cores is increased.
- a composition comprising water-in-oil microemulsion droplets and/or hydrated reverse micelles to produce an anhydrous mixture, wherein the droplet/micelle cores have low water activity and contain a latent fragrance enhancer which is activated when the water activity within the cores is increased.
- the microemulsion composition for use in this embodiment of the invention may of course be as defined herein.
- the invention provides a perfume comprising water-in-oil microemulsion droplets and/or hydrated reverse micelles, wherein the droplet/micelle cores have low water activity and contain a latent fragrance enhancer which is activated when the water activity within the cores is increased.
- the perfume preferably includes one or more co-fragrances, and any of a wide variety of known perfume formulations (e.g. based on ethanol or propylene glycol) may be employed. Such perfumes may be incorporated into a wide range of perfumed goods (as defined infra).
- the fragrance delivery system may also be used to release a cascade of different fragrances over time to produce a particular desired fragrance profile. This may be achieved by using combinations of different enzymes and cognate substrates within a single MEM system, or by using mixtures of different MEMs each having different solubilized enzyme/precursor systems. Control over the rate of release may then be achieved through any or a combination of the following mechanisms:
- Suitable enzyme sources include bacterial, fungal (e.g. yeast), plant, animal (e.g. mammalian) sources, and may include those derived from thermophilic and halophilic organisms); and/or
- the fragrance/fragrance enhancer precursor may comprise any of a large number of known fragrance/fragrance enhancer glycosides (for example furaneol glycoside, maltol glycoside or mustard oil glycoside, e.g. a glucosinolate or thioglucoside) .
- known fragrance/fragrance enhancer glycosides for example furaneol glycoside, maltol glycoside or mustard oil glycoside, e.g. a glucosinolate or thioglucoside
- the active fragrance or fragrance enhancer moiety is preferably a fragrance/enhancer aglycone.
- fragrance/enhancer aglycones having the general formula R-OH.
- R may be selected from an aliphatic alcohol residue, an aromatic alcohol residue (for example a terpene, e.g. menthol, geraniol or citronellol) and an alicyclic alcohol residue.
- Such embodiments may find particular application in the delivery of sweet and/or fruit fragrances.
- the fragrance/enhancer aglycone may have the general formula R-SH.
- the enzyme for use in the invention may be selected from any of oxidoreductases, transferases, hydrolases, Iyases, isomerases, ligases or combinations of different enzymes of any of the aforementioned type.
- hydrolases selected from ester hydrolases, glycosyl hydrolases, ether (e.g. thioether) hydrolases, peptide hydrolases or combinations of any of the foregoing.
- ether hydrolases e.g. thioether hydrolases
- peptide hydrolases e.g. peptide hydrolases or combinations of any of the foregoing.
- Such enzymes find particular application in the generation of fragrance or fragrance enhancer aglycones from glycoside precursors.
- Preferred ester hydrolases for use according to the invention include carboxylic ester hydrolase (e g. Iipase), thioester hydrolase, phosphoric monoester hydrolase, phosphoric diester hyd-colase, t ⁇ phospho ⁇ c monoester hydrolase, a sulphuric ester hydrolase, diphosphoric monoester hydrolase and combinations of any of the foregoing.
- Preferred glycosyl hydrolases for use according to the invention include those which hydrolyse O-glycosyl residues, and in particular ⁇ -glucosidase, ⁇ - glucosidase, ⁇ -galactosidase or ⁇ -galactosidase.
- Other preferred glycosyl hydrolases include those which hydrolyse /V-glycosy 1 or S-glycosyl compounds In the latter case, particularly preferred is myrosinase, which finds particular application in the hydrolysis of mustard oil glycosides (such as glucosinolates and thioglucosides) to aglycones of general formula R-SH.
- Preferred peptide hydrolases include ⁇ -aminoacylpeptide hydrolase, peptidyiamino-acid or acylamino-acid hydrolases, dipeptide hydrolases, dipeptidylpeptide hydrolases, peptidyldipeptide hydrolases, proteinases (e.g. se ⁇ ne proteinases, SH-protemases, acid proteinases or metalloprotemases) or combinations of any of the foregoing.
- proteinases e.g. se ⁇ ne proteinases, SH-protemases, acid proteinases or metalloprotemases
- the droplets or micelles may further comprise a surfactant, and any surfactant with a low hydrophilic-lipophilic balance value may be used.
- suitable surfactants for use in the invention include sorbitan esters (e.g. sorbitan monooleate), glycerol derivatives (e.g. stearyl monoglyceride), phospholipids (e.g. lecithin), naturally occurring phosphoglycerides (e.g. phosphatidylcholine or phosphatidylethanolamine) and mixtures of one or more of these surfactants.
- a surfactant especially where sunflower oil is used is a mixture of lecithin and sorbitan monooleate.
- a co-surfactant is used in addition to the surfactants discussed above.
- Any suitable co-surfactant may be used, provided that it functions to stabilize the water-oil interface.
- Particularly preferred are co-surfactants selected from short chain alcohols, propylene glycol or mixtures thereof.
- the surf actant/co-surf actant mix for use in the compositions of the invention are preferably selected such that the packing parameter 5 p (as hereinbefore defined) of the surfactant/co-sur actant mix is greater than 1 .
- Particularly preferred according to the invention are double tail and/or medium tail length surfactants/co-surfactants.
- Surfactant/co-surfactants having relatively high V to a ratios have been found to be particularly useful for use in the invention.
- the R value of the microemulsion droplets and/or hydrated reverse micelles in the compositions of the invention is preferably less than 10 (e.g. less than 5).
- the water activity in the droplet/micelle core is very low, and may render the solubilized enzyme(s) latent and/or modify enzyme activity and/or specificity.
- the droplet/micelle size is preferably 1 -1 00 nm, and in most applications is 1 -10 nm.
- compositions of the invention find application in any perfumed product which can be formulated and stored in a substantially anhydrous condition and which become hydrated in use.
- the invention finds application in a wide range of products including tableware (napkins, table dressings and serviettes), deodorants (including those for use on the body, in the air and on surfaces such as furniture, carpet and upholstery) .
- the products may be in any convenient form, including sprays, sticks, bars, granules, powders, impregnated sheets, tablets and non-aqueous solutions)
- talcs e g. body talcs
- furniture polishes and waxes e g. body talcs
- anti- perspirants for application to the body and to work sur aces and floors
- laundry products including detergents, fabric softeners and antistatic agents
- cosmetics toiletries, personal hygiene products and perfumes
- the invention finds application in deodorants, air fresheners, laundry freshener or washes, soaps, perfumes, surface cleaners or scourers, cosmetics, litters (e.g. cat litters), nappies, sanitary or incontinence pads, shaving sticks or shaving foams, odour-masking shoe inserts, tissues and towels.
- deodorants air fresheners, laundry freshener or washes, soaps, perfumes, surface cleaners or scourers, cosmetics, litters (e.g. cat litters), nappies, sanitary or incontinence pads, shaving sticks or shaving foams, odour-masking shoe inserts, tissues and towels.
- the fragrance in all the foregoing products is stable on storage in the anhydrous state but is released when the product is hydrated in use
- the moisture of the skin hydrates the perfumes and deodorants of the invention, while the laundry products are hydrated by the water used in the wash.
- any of a wide variety of known MEM systems may be used. Examples include those described in El-Nokaly and Georgia ( 1 991 ), American Chemical Society Symposium Series 448, pp 62-79 and by Rees and Robinson (op c/t) .
- Example 1 Flavour enhancing composition
- Aroma glycoside and glycosidase was incorporated into the aqueous phase of the MEM perfume system described by Tokuoka et al ( 1 994) Colloid Polym Sci 272, 31 7 (the teachings of which relating to MEM compositions are incorporated herein by reference) .
- Various formulations were produced having 0J , 0.2, 0.3, 0.4 and 0.5 % glycosidase and OJ , 0.3, 0.5, 0.8 and 1 % flavour glycoside. On hydration, the compositions exhibited sustained release of the aroma over time.
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Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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AU15736/00A AU1573600A (en) | 1998-12-03 | 1999-12-02 | Microemulsion compositions |
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GBGB9826555.6A GB9826555D0 (en) | 1998-12-03 | 1998-12-03 | Microemulsion compositions |
GB9826555.6 | 1998-12-03 |
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PCT/GB1999/004053 WO2000032153A1 (en) | 1998-12-03 | 1999-12-03 | Microemulsion compositions |
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001096521A1 (en) * | 2000-06-14 | 2001-12-20 | Henkel Kommanditgesellschaft Auf Aktien | Fabric conditioner in liquid or gel form |
WO2002049591A3 (en) * | 2000-12-21 | 2002-08-29 | Beiersdorf Ag | Antiperspirant cloths |
EP2039376A1 (en) * | 2007-09-13 | 2009-03-25 | The Procter & Gamble | Absorbent articles comprising an aglycone derivable from an iridoid glycoside |
US7556210B2 (en) | 2006-05-11 | 2009-07-07 | S. C. Johnson & Son, Inc. | Self-contained multi-sprayer |
US8551973B2 (en) | 2008-12-23 | 2013-10-08 | Gilead Pharmasset Llc | Nucleoside analogs |
US8716263B2 (en) | 2008-12-23 | 2014-05-06 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
US8716262B2 (en) | 2008-12-23 | 2014-05-06 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
US8859756B2 (en) | 2010-03-31 | 2014-10-14 | Gilead Pharmasset Llc | Stereoselective synthesis of phosphorus containing actives |
WO2023012493A1 (en) * | 2021-08-03 | 2023-02-09 | Thomas Kuhlmann | Pad and reactor for the development of terpenes nd their dispersion in room air |
US12116550B2 (en) | 2020-06-03 | 2024-10-15 | The Procter & Gamble Company | Process of making a liquid conditioning composition |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996023425A1 (en) * | 1995-02-01 | 1996-08-08 | Societe Des Produits Nestle S.A. | Food microemulsion formulations |
WO1998008927A2 (en) * | 1996-08-26 | 1998-03-05 | Colgate-Palmolive Company | Color/perfume concentrates |
US5766628A (en) * | 1992-02-24 | 1998-06-16 | Merz + Co. Gmbh & Co. | Bath and shower composition having vesicle-forming properties and method for the production and use thereof |
WO1999062357A1 (en) * | 1998-06-01 | 1999-12-09 | Kerry Ingredients (Uk) Limited | Flavour delivering systems comprising a microemulsion or hydrated reversed micelles |
-
1998
- 1998-12-03 GB GBGB9826555.6A patent/GB9826555D0/en not_active Ceased
-
1999
- 1999-12-02 AU AU15736/00A patent/AU1573600A/en not_active Abandoned
- 1999-12-03 WO PCT/GB1999/004053 patent/WO2000032153A1/en active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5766628A (en) * | 1992-02-24 | 1998-06-16 | Merz + Co. Gmbh & Co. | Bath and shower composition having vesicle-forming properties and method for the production and use thereof |
WO1996023425A1 (en) * | 1995-02-01 | 1996-08-08 | Societe Des Produits Nestle S.A. | Food microemulsion formulations |
WO1998008927A2 (en) * | 1996-08-26 | 1998-03-05 | Colgate-Palmolive Company | Color/perfume concentrates |
WO1999062357A1 (en) * | 1998-06-01 | 1999-12-09 | Kerry Ingredients (Uk) Limited | Flavour delivering systems comprising a microemulsion or hydrated reversed micelles |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001096521A1 (en) * | 2000-06-14 | 2001-12-20 | Henkel Kommanditgesellschaft Auf Aktien | Fabric conditioner in liquid or gel form |
WO2002049591A3 (en) * | 2000-12-21 | 2002-08-29 | Beiersdorf Ag | Antiperspirant cloths |
US7556210B2 (en) | 2006-05-11 | 2009-07-07 | S. C. Johnson & Son, Inc. | Self-contained multi-sprayer |
EP2039376A1 (en) * | 2007-09-13 | 2009-03-25 | The Procter & Gamble | Absorbent articles comprising an aglycone derivable from an iridoid glycoside |
EP2039375A1 (en) * | 2007-09-13 | 2009-03-25 | The Procter and Gamble Company | Absorbent articles comprising an aglycone derivable from an iridoid glycoside |
WO2009034527A3 (en) * | 2007-09-13 | 2010-03-18 | The Procter & Gamble Company | Absorbent articles comprising an aglycone derivable from an iridoid glycoside |
US8551973B2 (en) | 2008-12-23 | 2013-10-08 | Gilead Pharmasset Llc | Nucleoside analogs |
US8716263B2 (en) | 2008-12-23 | 2014-05-06 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
US8716262B2 (en) | 2008-12-23 | 2014-05-06 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
US8957045B2 (en) | 2008-12-23 | 2015-02-17 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
US9045520B2 (en) | 2008-12-23 | 2015-06-02 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
US8859756B2 (en) | 2010-03-31 | 2014-10-14 | Gilead Pharmasset Llc | Stereoselective synthesis of phosphorus containing actives |
US12116550B2 (en) | 2020-06-03 | 2024-10-15 | The Procter & Gamble Company | Process of making a liquid conditioning composition |
WO2023012493A1 (en) * | 2021-08-03 | 2023-02-09 | Thomas Kuhlmann | Pad and reactor for the development of terpenes nd their dispersion in room air |
Also Published As
Publication number | Publication date |
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GB9826555D0 (en) | 1999-01-27 |
AU1573600A (en) | 2000-06-19 |
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