US20090291052A1 - Use of alkylpolyglycosides as emulsifying agents for the preparation of oil-in-water emulsions comprising inorganic fillers or pigments, and oil-in-water emulsions comprising such alkylpolyglycosides - Google Patents
Use of alkylpolyglycosides as emulsifying agents for the preparation of oil-in-water emulsions comprising inorganic fillers or pigments, and oil-in-water emulsions comprising such alkylpolyglycosides Download PDFInfo
- Publication number
- US20090291052A1 US20090291052A1 US12/511,762 US51176209A US2009291052A1 US 20090291052 A1 US20090291052 A1 US 20090291052A1 US 51176209 A US51176209 A US 51176209A US 2009291052 A1 US2009291052 A1 US 2009291052A1
- Authority
- US
- United States
- Prior art keywords
- oil
- pigments
- emulsion
- alkylpolyglycosides
- fillers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000839 emulsion Substances 0.000 title claims abstract description 55
- 239000003995 emulsifying agent Substances 0.000 title claims abstract description 30
- 239000011256 inorganic filler Substances 0.000 title claims description 13
- 239000001023 inorganic pigment Substances 0.000 title claims description 13
- 229910003475 inorganic filler Inorganic materials 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000007764 o/w emulsion Substances 0.000 claims description 9
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 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 claims description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 5
- 239000008103 glucose Substances 0.000 claims description 5
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 239000000049 pigment Substances 0.000 abstract description 21
- 239000000945 filler Substances 0.000 abstract description 20
- 239000006185 dispersion Substances 0.000 abstract description 9
- 239000007957 coemulsifier Substances 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 239000002270 dispersing agent Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
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- 230000001804 emulsifying effect Effects 0.000 description 16
- 239000008346 aqueous phase Substances 0.000 description 14
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- 229930182478 glucoside Natural products 0.000 description 6
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- 239000004408 titanium dioxide Substances 0.000 description 5
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
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- 239000011787 zinc oxide Substances 0.000 description 4
- DWHIUNMOTRUVPG-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCO DWHIUNMOTRUVPG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
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- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
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- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
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- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
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- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
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- LFSBSHDDAGNCTM-UHFFFAOYSA-N cobalt(2+);oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[O-2].[Ti+4].[Co+2] LFSBSHDDAGNCTM-UHFFFAOYSA-N 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
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- 229920001436 collagen Polymers 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
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- 239000006184 cosolvent Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 1
- 229940031578 diisopropyl adipate Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GTZOYNFRVVHLDZ-UHFFFAOYSA-N dodecane-1,1-diol Chemical compound CCCCCCCCCCCC(O)O GTZOYNFRVVHLDZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000008524 evening primrose extract Nutrition 0.000 description 1
- 239000010475 evening primrose oil Substances 0.000 description 1
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- 235000010492 gellan gum Nutrition 0.000 description 1
- 239000000216 gellan gum Substances 0.000 description 1
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- 125000005456 glyceride group Chemical group 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- QAKXLTNAJLFSQC-UHFFFAOYSA-N hexadecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC QAKXLTNAJLFSQC-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- JCDAAXRCMMPNBO-UHFFFAOYSA-N iron(3+);oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Ti+4].[Ti+4].[Fe+3].[Fe+3] JCDAAXRCMMPNBO-UHFFFAOYSA-N 0.000 description 1
- 229940078545 isocetyl stearate Drugs 0.000 description 1
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 1
- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Natural products CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229940089456 isopropyl stearate Drugs 0.000 description 1
- 239000012182 japan wax Substances 0.000 description 1
- 229940119170 jojoba wax Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- HFWWEMPLBCKNNM-UHFFFAOYSA-N n-[bis(hydroxyamino)methyl]hydroxylamine Chemical compound ONC(NO)NO HFWWEMPLBCKNNM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- IIGMITQLXAGZTL-UHFFFAOYSA-N octyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCC IIGMITQLXAGZTL-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012168 ouricury wax Substances 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- BWOROQSFKKODDR-UHFFFAOYSA-N oxobismuth;hydrochloride Chemical compound Cl.[Bi]=O BWOROQSFKKODDR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940100460 peg-100 stearate Drugs 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- BFZNCPXNOGIELB-UHFFFAOYSA-N propan-2-yl 10-[5,6-dihexyl-2-(8-oxo-8-propan-2-yloxyoctyl)cyclohex-3-en-1-yl]dec-9-enoate Chemical compound CCCCCCC1C=CC(CCCCCCCC(=O)OC(C)C)C(C=CCCCCCCCC(=O)OC(C)C)C1CCCCCC BFZNCPXNOGIELB-UHFFFAOYSA-N 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
- DPBVJRXPSXTHOL-UHFFFAOYSA-N propyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCCC DPBVJRXPSXTHOL-UHFFFAOYSA-N 0.000 description 1
- 239000001944 prunus armeniaca kernel oil Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008171 pumpkin seed oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- PJHKBYALYHRYSK-UHFFFAOYSA-N triheptanoin Chemical compound CCCCCCC(=O)OCC(OC(=O)CCCCCC)COC(=O)CCCCCC PJHKBYALYHRYSK-UHFFFAOYSA-N 0.000 description 1
- 229940118576 triisostearyl citrate Drugs 0.000 description 1
- ICWQKCGSIHTZNI-UHFFFAOYSA-N tris(16-methylheptadecyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCCCCCCCCCC(C)C)CC(=O)OCCCCCCCCCCCCCCCC(C)C ICWQKCGSIHTZNI-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
-
- 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
-
- 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
- A61K8/062—Oil-in-water 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
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- 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
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
- C09K23/018—Mixtures of two or more different organic oxygen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/56—Glucosides; Mucilage; Saponins
Definitions
- a subject-matter of the present invention is the use of specific alkylpolyglycosides as emulsifying agents for the preparation of oil-in-water emulsions comprising inorganic fillers or pigments.
- the invention finds application in particular in the cosmetics and pharmaceutical field.
- fillers and pigments in particular of inorganic fillers and pigments, in an emulsion is complex. This is because the presence of fillers or pigments introduces electrical charges into the emulsion which disrupt this emulsion. The latter is difficult to stabilize, often forcing the formulator to use a complex emulsifying system, one or more stabilizers for the aqueous phase, or a dispersing surfactant, to prevent reagglomeration of the fillers over time.
- the problem to be solved thus consists in having available oil-in-water emulsions, comprising inorganic fillers or pigments, which are easy to prepare and which are stable over time, that is to say in which the pigments or fillers do not reagglomerate.
- an emulsifier based on an alkylpolyglycoside structure with a length of alkyl chain having from 6 to 12 carbon atoms makes it possible to readily formulate oil-in-water (hereinafter “O/W”) emulsions comprising inorganic fillers and/or pigments.
- O/W oil-in-water
- This result is all the more surprising since short-chain surfactants are not supposed to exhibit good emulsifying properties.
- These emulsions exhibit an excellent dispersion of the fillers without it being necessary to add coemulsifier or dispersant and without it being useful either to apply specific manufacturing processes as described above.
- the dispersion obtained with the emulsifier according to the invention is furthermore stable over time, that is to say that, surprisingly, the emulsifier makes it possible, by itself alone, to prevent the reagglomeration of the fillers and/or pigments, including in fluid emulsions such as milks.
- alkylpolyglycosides represented by the following formulae (Ia) or (Ib):
- X represents the residue of a C 5 or C 6 sugar, preferably the glucose or xylose residue
- R represents an alkylene or alkylidene group having from 6 to 12 carbon atoms
- r, s and t represent the mean degree of polymerization of each sugar residue. They are greater than 1 and less than or equal to 5, and more particularly less than or equal to 2.5.
- alkylpolyglycosides represented by the following formulae (Ia) or (Ib):
- X represents the residue of C 5 or C 6 sugar, preferably the glucose or xylose residue
- R represents an alkylene or alkylidene group having from 6 to 12 carbon atoms
- r, s and t represent the mean degree of polymerization of each sugar residue. They are greater than 1 and less than or equal to 5, and more particularly less than or equal to 2.5.
- r, s and t are more particularly between 1.005 and 1.5.
- X represents the glucose residue
- r, s and tare more particularly between 1.05 and 2.
- the compounds of formula (Ia) or (Tb) in accordance with the present invention can be prepared by reaction of a reducing sugar and of an alkanediol having from 6 to 12 carbon atoms, preferably hexanediol, octanediol, decanediol or dodecanediol, in desired predetermined proportions.
- This reaction results either in the products resulting from the acetalization of one of the two hydroxyl groups of the diol (compounds (Ia)), on in the products resulting from the acetalization of both hydroxyl groups of the diol (compounds (Ib)), or in the mixture of the compounds (Ia) and (Ib).
- these compounds will preferably be prepared according to one of the two routes conventionally used for the synthesis of alkylpolyglycosides, for example by reaction, in an acidic medium, between the alkanediol having from 6 to 12 carbon atoms and a reducing sugar, such as glucose or xylose.
- this synthesis can be supplemented by neutralization, filtration or decoloration operations or operations for the partial distillation or extraction of the excess diol.
- a subject matter of the latter is a concentrate (C), characterized in that it consists essentially of:
- R 1 represents a linear or branched alkyl radical comprising from 6 to 12 carbon atoms
- X 1 represents the xylose residue
- p 1 which represents the mean degree of polymerization of the xylose residue, is a decimal number of greater than 1 and less than or equal to 2.5,
- R 2 represents a linear or branched alkyl radical comprising from 6 to 12 carbon atoms
- G represents the glucose residue
- n which represents the mean degree of polymerization of the xylose residue, is a decimal number of greater than 1 and less than or equal to 2.5
- the mixture (M) of compounds of formula (IIIa) and of formula (IIIb) is composed essentially:
- topically acceptable solvents are water, alcohols, such as ethanol, propanol or isopropanol, glycols, such as propylene glycol, butylene glycol or hexylene glycol, or water/alcohol or water/glycol mixtures.
- the concentrate (C) as defined above exhibits one or another or some following specific characteristics:
- a subject matter of the invention is the use of at least one alkylpolyglycoside of formula (Ia) or (Ib) as emulsifying agent for the preparation of oil-in-water emulsions comprising inorganic fillers and/or pigments.
- a subject matter of the invention is the use of at least one alkylpolyglycoside of general formula (II):
- R—O—(X) p the R—O— group is bonded to X via the anomeric carbon of the sugar residue, so as to form an acetal functional group.
- p is more particularly between 1.005 and 1.5.
- p is more particularly between 1.05 and 2.
- the compound of formula R—O—(X) p can be prepared according to methods well known to a person skilled in the art.
- alkylpolyglycosides in the concentrate (C) in accordance with the invention make it possible to prepare oil-in-water (O/W) emulsions comprising inorganic fillers and/or pigments.
- They advantageously represent from 0.2 to 10% by weight, preferably from 0.5 to 5% by weight, of the O/W emulsion.
- the inorganic fillers and/or pigments can be lamellar or spherical and without specific limitation with respect to the particle size. Mention may in particular be made, as examples of inorganic fillers and pigments, of titanium dioxide; zinc oxide; iron oxide (black, red or yellow); iron titanate; carbon black; chromium oxide; chromium hydroxide; zirconium oxide; cerium oxide; cobalt titanate; ultramarine; Prussian blue; titanium oxide-coated mica; bismuth oxychloride; pearl essence; talc; aluminum powder; copper powder; gold powder; mica; sericite; boron nitride; photochromic pigments; or interferential pigments. These fillers may have been subjected to a surface treatment or may be encapsulated, such as, for example, in nylon matrices or polymers.
- These fillers and pigments generally represent from 0.5 to 40% by weight, preferably from 2 to 25% by weight, of the O/W emulsion.
- the O/W emulsion also comprises from 1 to 50% by weight, preferably from 5 to 35% by weight and more preferably from 5 to 25% by weight of a fatty phase composed of one or more oils and/or of one or more waxes.
- This oil can also be chosen from fatty acids, fatty alcohols, waxes of natural or synthetic origin and more generally still any fatty substance of vegetable, animal or synthetic origin.
- the wax is advantageously chosen from fatty substances which are solid at ambient temperature, such as, for example, beeswax; carnauba wax, candelilla wax; ouricury wax; Japan wax; cork fiber or sugarcane wax; paraffin waxes; lignite waxes; microcrystalline waxes; lanolin wax; ozokerite; polyethylene wax, hydrogenated oils; silicone waxes; vegetable waxes; fatty alcohols and fatty acids which are solid at ambient temperature; or glycerides which are solid at ambient temperature.
- fatty substances which are solid at ambient temperature such as, for example, beeswax; carnauba wax, candelilla wax; ouricury wax; Japan wax; cork fiber or sugarcane wax; paraffin waxes; lignite waxes; microcrystalline waxes; lanolin wax; ozokerite; polyethylene wax, hydrogenated oils; silicone waxes; vegetable waxes; fatty alcohols and fatty acids which are solid at ambient temperature; or g
- the O/W emulsion in accordance with the invention can also comprise up to 10% by weight, for example from 0.1 to 10% by weight, of a stabilizing system.
- the stabilizing system can be composed of one or more compounds chosen from magnesium silicate; aluminum silicate; sodium silicate; xanthan gum; acacia gum; locust bean gum; scleroglucan gum; gellan gum; alginates; cellulose and cellulose derivatives; clays; starches and starch derivatives; carbomer; acrylic acid polymers and copolymers; acryloyldimethyl taurate polymers and copolymers; polyvinylpyrrolidone; acrylamide polymers and copolymers; or polyurethanes.
- the O/W emulsion can also comprise up to 30% by weight of one or more additives generally used in cosmetics and chosen from:
- a subject matter of the present invention is an oil-in-water emulsion comprising at least one alkylpolyglycoside corresponding in particular to the formula (Ia), (Ib) or (II), and pigments and/or fillers.
- a subject matter of the latter is an oil-in-water emulsion comprising from 0.5% to 10% by weight and more particularly from 1% to 5% by weight of the concentrate (C) as defined above, and inorganic pigments and/or fillers.
- the O/W emulsion in accordance with the invention can be prepared by processes known to a person skilled in the art, such as, for example, a process which comprises the following stages:
- a subject matter of the latter is a process for the preparation of a cosmetic or pharmaceutical oil-in-water emulsion for topical use, characterized in that between 0.2% and 10% by weight and more particularly between 0.5% and 5% by weight of a concentrate (C) as defined above is mixed with the other constituents of said composition.
- the protection factor is evaluated according to the method described below:
- the protection factor is evaluated in vitro by measuring the absorbing power with respect to UV-B and UV-A radiation after spreading a film of emulsion over a support which models the skin surface.
- the emulsion is spread in a calibrated way (2 mg/cm 2 ) over a prehydrated collagen matrix sold under the name Vitroskin® by IMS. After drying the film for a period of 15 minutes, the coated support is subjected to exposure to UV radiation using a Labsphere® spectro-photometer.
- the sun protection coefficient is calculated by the software of the device according to the Diffey formula from the transmission of the UV radiation over the whole spectrum between 280 and 400 nm.
- the relative importance of the protection with respect to UV-A radiation is calculated by producing the ratio of the area under the absorbance curve in the UV-A spectrum to the area under the absorbance curve in the UV-B spectrum.
- a UV-A/UV-B ratio of >0.6 is recommended for effective protection with respect to UV-A radiation.
- 1,10-decanediol sold by Cognis under the name Speziol® C10/2
- the reactor is brought to a temperature of 90° C., so as to effectively melt the 1,10-decanediol, stirring is started and 390.0 g of xylose are dispersed in the presence of a catalytic amount of sulfuric acid.
- the product After two hours at 80° C./85° C. under vacuum and neutralization with sodium hydroxide, the product exhibits the following analytical characteristics:
- O/W emulsions are prepared which comprise the following ingredients:
- Emulsifier 02.50% C 12 -C 15 Alkyl benzoate 20.00% Titanium oxide (20 nm/dimethicone coating) 10.00% B Cyclomethicone 05.00% Glycerol 07.00% C Tetrasodium EDTA 00.20% Water q.s. for 100% Carbomer ® 00.05% Tromethamine q.s. pH > 7 Magnesium silicate/Aluminum silicate 01.00% Xanthan gum 00.15% D DL- ⁇ -Tocopherol 00.05% Preservatives q.s.
- the Carbomer®, the magnesium silicate/aluminum silicate and the xanthan gum are dispersed in the aqueous phase.
- the aqueous phase is heated to 70-85° C. and then the EDTA and the tromethamine are added.
- the fatty phase comprising the titanium oxide, the emulsifier and the C 12 -C 15 alkyl benzoate, is heated to an identical temperature of 70 to 85° C.
- the cyclo-methicone and the glycerol are added to this hot fatty phase.
- the two phases are subsequently mixed and emulsified using a rotor-stator emulsifying device (Silverson laboratory mixer). After emulsifying for a few minutes, the emulsion is cooled with moderate stirring.
- a rotor-stator emulsifying device Siliconverson laboratory mixer. After emulsifying for a few minutes, the emulsion is cooled with moderate stirring.
- the tocopherol and the preservatives are added at the end of cooling with moderate stirring.
- butylglucoside it is not possible with butylglucoside to obtain an emulsion and dodecylglucoside results in emulsions which are less stable than those obtained with the alkylglucosides according to the invention.
- Cetearyl-glucoside and dodecylglucoside give agglomerates.
- the ethoxylated nonionic surfactants are less effective than the alkylpolyglycosides according to the invention.
- An emulsion is prepared which comprises the following ingredients:
- the Carbomer®, the magnesium silicate/aluminum silicate and the xanthan gum are dispersed in the aqueous phase.
- the aqueous phase is heated to 70-85° C. and then the EDTA and the tromethamine are added.
- the fatty phase comprising the titanium oxide and the zinc oxide, the emulsifier and the oil, is heated to an identical temperature of 70 to 85° C.
- the cyclomethicone and the glycerol are added to this hot fatty phase.
- the two phases are subsequently mixed and emulsified using a rotor-stator emulsifying device (Silverson laboratory mixer). After emulsifying for a few minutes, the emulsion is cooled wish moderate stirring.
- a rotor-stator emulsifying device Siliconverson laboratory mixer. After emulsifying for a few minutes, the emulsion is cooled wish moderate stirring.
- the tocopherol and the preservatives are added at the end of cooling with moderate stirring.
- the emulsifier according to the invention makes it possible, in contrast to the comparative emulsifiers, to retain a fine and homogeneous dispersion of the filters during the storage with consequently a visual texture which remains perfectly smooth over time and a stable protection factor, both in the UV-B spectrum and in the UV-A spectrum, as is illustrated by the value of the factor and that of the UV-A/UV-B ratio.
- An emulsion is prepared which comprises the following ingredients:
- a Emulsifier 03.00% Caprylic/capric triglycerides 20.00% Zinc oxide 05.00% Glycerol 05.00% C Tetrasodium EDTA 00.10% Water q.s. for 100% Sepigel ® 305 01.50% Tromethamine q.s. pH > 7 Magnesium silicate/Aluminum silicate 01.00% Xanthan gum 00.15% D DL- ⁇ -Tocopherol 00.05% Preservatives q.s.
- the Sepigel® 305 (polyacrylamide and C 11 -C 13 isoparaffin and laureth-7; sold by Seppic), the magnesium silicate/aluminum silicate and the xanthan gum are dispersed in the aqueous phase.
- the EDTA and the tromethamine are added to the aqueous phase.
- the fatty phase is produced by simple mixing of the constituents without heating.
- the two phases are subsequently mixed and emulsified using a rotor-stator emulsifying device (Silverson laboratory mixer).
- the tocopherol and the preservatives are added with moderate stirring.
- the pigment paste is milled beforehand on a bead mill.
- the water is heated to 70-75° C. and then the Micropearl®, the EDTA and the pigment paste are added to the hot aqueous phase.
- the fatty phase comprising the emulsifier and the oils, is heated to a temperature of 70 to 75° C.
- the cyclomethicone and the Sepigel® 305 are added to this hot fatty phase.
- the two phases are subsequently mixed and emulsified using a rotor-stator emulsifying device (Silverson laboratory mixer). After emulsifying for a few minutes, the emulsion is cooled with moderate stirring.
- a rotor-stator emulsifying device Siliconverson laboratory mixer. After emulsifying for a few minutes, the emulsion is cooled with moderate stirring.
- the preservatives and the fragrance are added at the end of cooling with moderate stirring.
- the fineness of the dispersion of the fillers is reflected by an improvement in the spreading over the skin, by uniform color and by a better rendering of the color on the skin: decrease in the whiteness (parameter L) and an enhancement in the colored parameters a (red hue) and b (blue hue).
- the non-uniformity in the color with the comparative examples is clearly apparent with regard to the standard deviation values for a and b, which are higher than in the example according to the invention.
- the pigment paste is milled beforehand on a bead mill.
- the Simulgel® NS sodium acryloyldimethyl taurate/hydroxyethyl acrylate copolymer and squalane and polysorbate 80; sold by Seppic
- the aqueous phase B is added to phase A to form the cream gel.
- the pigment paste (phase C) and subsequently phase D are then added directly to the cream gel with moderate stirring.
Abstract
A composition and process of preparation of emulsifier agents based on an alkylpolyglycoside structure with a length of alkyl chain having from 6 to 12 carbon atoms to be used. The resulting emulsions exhibit an excellent dispersion of the fillers and/or pigments without it being necessary to add coemulsifier or dispersant. The emulsifier makes it possible, by itself alone, to prevent the reagglomeration of the fillers and/or pigments.
Description
- This application is a division of application Ser. No.: 10/493,726 filed on Apr. 23, 2004; which is the 35 U.S.C. 371 national stage of International application PCT/FR02/03609 filed on Oct. 22, 2002; which claimed priority to French application FR 01/13808 filed Oct. 25, 2001. The entire contents of each of the above-identified applications are hereby incorporated by reference.
- 1. Field of the Invention
- A subject-matter of the present invention is the use of specific alkylpolyglycosides as emulsifying agents for the preparation of oil-in-water emulsions comprising inorganic fillers or pigments.
- The invention finds application in particular in the cosmetics and pharmaceutical field.
- 2. Related Art
- The formulation of fillers and pigments, in particular of inorganic fillers and pigments, in an emulsion is complex. This is because the presence of fillers or pigments introduces electrical charges into the emulsion which disrupt this emulsion. The latter is difficult to stabilize, often forcing the formulator to use a complex emulsifying system, one or more stabilizers for the aqueous phase, or a dispersing surfactant, to prevent reagglomeration of the fillers over time.
- In the case of antisun emulsions, this reagglomeration of the fillers results in a low or unstable UV protection factor which decreases over time. In the case of makeup emulsions, reagglomeration of the fillers can also occur, resulting in poor homogeneity of the color in the emulsion itself or when it is applied to the skin. In both these cases, the reagglomeration of the fillers, if it is significant, detrimentally affects the texture of the emulsion, which, instead of appearing smooth and glossy, becomes dull and granular.
- To overcome these difficulties, recourse is often had:
-
- either to complex emulsifying systems, which are generally based on fatty chains with a length of 16 and 18 carbon atoms (saturated, unsaturated or branched);
- or to complex manufacturing processes; for example, inorganic filters with a UV-inhibiting role are very often predispersed in the oil phase or in the water phase.
- The problem to be solved thus consists in having available oil-in-water emulsions, comprising inorganic fillers or pigments, which are easy to prepare and which are stable over time, that is to say in which the pigments or fillers do not reagglomerate.
- It has now been discovered unexpectedly, and this is the basis of the invention, that an emulsifier based on an alkylpolyglycoside structure with a length of alkyl chain having from 6 to 12 carbon atoms makes it possible to readily formulate oil-in-water (hereinafter “O/W”) emulsions comprising inorganic fillers and/or pigments. This result is all the more surprising since short-chain surfactants are not supposed to exhibit good emulsifying properties. These emulsions exhibit an excellent dispersion of the fillers without it being necessary to add coemulsifier or dispersant and without it being useful either to apply specific manufacturing processes as described above. The dispersion obtained with the emulsifier according to the invention is furthermore stable over time, that is to say that, surprisingly, the emulsifier makes it possible, by itself alone, to prevent the reagglomeration of the fillers and/or pigments, including in fluid emulsions such as milks.
- Thus, according to a first aspect, a subject matter of the invention is alkylpolyglycosides represented by the following formulae (Ia) or (Ib):
-
HO—R—O(X)r (Ia) -
(X)s—OR—O—(X)t (Ib) - in which:
- X represents the residue of a C5 or C6 sugar, preferably the glucose or xylose residue;
- R represents an alkylene or alkylidene group having from 6 to 12 carbon atoms;
- r, s and t represent the mean degree of polymerization of each sugar residue. They are greater than 1 and less than or equal to 5, and more particularly less than or equal to 2.5.
- One aspect of the invention is alkylpolyglycosides represented by the following formulae (Ia) or (Ib):
-
HO—R—O(X)r (Ia) -
(X)s—OR—O—(X)t (Ib) - in which:
- X represents the residue of C5 or C6 sugar, preferably the glucose or xylose residue;
- R represents an alkylene or alkylidene group having from 6 to 12 carbon atoms;
- r, s and t represent the mean degree of polymerization of each sugar residue. They are greater than 1 and less than or equal to 5, and more particularly less than or equal to 2.5.
- When X represents the xylose residue, r, s and t are more particularly between 1.005 and 1.5.
- When X represents the glucose residue, r, s and tare more particularly between 1.05 and 2.
- The compounds of formula (Ia) or (Tb) in accordance with the present invention can be prepared by reaction of a reducing sugar and of an alkanediol having from 6 to 12 carbon atoms, preferably hexanediol, octanediol, decanediol or dodecanediol, in desired predetermined proportions.
- This reaction results either in the products resulting from the acetalization of one of the two hydroxyl groups of the diol (compounds (Ia)), on in the products resulting from the acetalization of both hydroxyl groups of the diol (compounds (Ib)), or in the mixture of the compounds (Ia) and (Ib).
- On an industrial scale, these compounds will preferably be prepared according to one of the two routes conventionally used for the synthesis of alkylpolyglycosides, for example by reaction, in an acidic medium, between the alkanediol having from 6 to 12 carbon atoms and a reducing sugar, such as glucose or xylose.
- Such synthetic routes are well known to a person skilled in the art.
- If appropriate, this synthesis can be supplemented by neutralization, filtration or decoloration operations or operations for the partial distillation or extraction of the excess diol.
- According to a second aspect of the present invention, a subject matter of the latter is a concentrate (C), characterized in that it consists essentially of:
-
- from 30% to 100% by weight of a mixture (M) of at least one compound of formula (IIIa)
-
R1—O(X1)p1 (IIIa) - in which
- R1 represents a linear or branched alkyl radical comprising from 6 to 12 carbon atoms,
- X1 represents the xylose residue,
- p1, which represents the mean degree of polymerization of the xylose residue, is a decimal number of greater than 1 and less than or equal to 2.5,
- and
of at least one compound of formula (IIIb) -
R2—O(G)n (IIIb) - in which
- R2 represents a linear or branched alkyl radical comprising from 6 to 12 carbon atoms,
- G represents the glucose residue,
- n, which represents the mean degree of polymerization of the xylose residue, is a decimal number of greater than 1 and less than or equal to 2.5, and
-
- from 0% to 70% by weight of a topically acceptable solvent.
- In the concentrate (C) as defined above, the mixture (M) of compounds of formula (IIIa) and of formula (IIIb) is composed essentially:
-
- of 20% to 99% by weight of at least one compound of formula (IIIa), and
- of 1% to 80% by weight of at least one compound of formula. (IIIb).
- Examples of topically acceptable solvents are water, alcohols, such as ethanol, propanol or isopropanol, glycols, such as propylene glycol, butylene glycol or hexylene glycol, or water/alcohol or water/glycol mixtures.
- According to preferred aspects of the present invention, the concentrate (C) as defined above exhibits one or another or some following specific characteristics:
-
- the concentrate (C) does not comprise solvent;
- the concentrate (C) is an aqueous solution of the mixture (M);
- the mixture (M) consists essentially of:
from 20% to 30% by weight of at least one compound of the formula (IIIa) and
from 70% to 80% by weight of at least one compound of formula (IIIb); - in the formula (IIIa), p is ≧1.005 and >1.5;
- in the formula (IIIb), n is ≧1.05 and >2.
- According to a third aspect, a subject matter of the invention is the use of at least one alkylpolyglycoside of formula (Ia) or (Ib) as emulsifying agent for the preparation of oil-in-water emulsions comprising inorganic fillers and/or pigments.
- According to a fourth aspect, a subject matter of the invention is the use of at least one alkylpolyglycoside of general formula (II):
-
R—O(X)p (II) - in which:
-
- R represents a linear or branched alkyl radical having from 6 to 11 carbon atoms;
- X represents the residue of a C5 or C6 sugar, preferably the glucose or xylose residue; and
- p, which represents the mean degree of polymerization of the sugar residue, is a decimal number of greater than 1 and less than or equal to 5, and more particularly of less than or equal to 2.5,
as emulsifying agent for the preparation of oil-in-water emulsions comprising inorganic fillers and/or pigments.
- In the formula R—O—(X)p, the R—O— group is bonded to X via the anomeric carbon of the sugar residue, so as to form an acetal functional group.
- When X represents the xylose residue, p is more particularly between 1.005 and 1.5.
- When X represents the glucose residue, p is more particularly between 1.05 and 2.
- The compound of formula R—O—(X)p can be prepared according to methods well known to a person skilled in the art.
- The alkylpolyglycosides in the concentrate (C) in accordance with the invention make it possible to prepare oil-in-water (O/W) emulsions comprising inorganic fillers and/or pigments.
- They advantageously represent from 0.2 to 10% by weight, preferably from 0.5 to 5% by weight, of the O/W emulsion.
- The inorganic fillers and/or pigments can be lamellar or spherical and without specific limitation with respect to the particle size. Mention may in particular be made, as examples of inorganic fillers and pigments, of titanium dioxide; zinc oxide; iron oxide (black, red or yellow); iron titanate; carbon black; chromium oxide; chromium hydroxide; zirconium oxide; cerium oxide; cobalt titanate; ultramarine; Prussian blue; titanium oxide-coated mica; bismuth oxychloride; pearl essence; talc; aluminum powder; copper powder; gold powder; mica; sericite; boron nitride; photochromic pigments; or interferential pigments. These fillers may have been subjected to a surface treatment or may be encapsulated, such as, for example, in nylon matrices or polymers.
- These fillers and pigments generally represent from 0.5 to 40% by weight, preferably from 2 to 25% by weight, of the O/W emulsion.
- The O/W emulsion also comprises from 1 to 50% by weight, preferably from 5 to 35% by weight and more preferably from 5 to 25% by weight of a fatty phase composed of one or more oils and/or of one or more waxes.
- The oil is advantageously chosen from the following oils:
-
- oils of vegetable origin, such as sweet almond oil, coconut oil, castor oil, jojoba oil, olive oil, rapeseed oil, peanut oil, sunflower oil, wheat germ oil, corn germ oil, soybean oil, cottonseed oil, alfalfa oil, poppy oil, pumpkinseed oil, evening primrose oil, millet oil, barley oil, rye oil, safflower oil, candlenut oil, passionflower oil, hazelnut oil, palm oil, karite butter, apricot kernel oil, calophyllum oil, sisymbrium oil, avocado oil or calendula oil;
- vegetable oils and their methyl esters which are ethoxylated;
- oils of animal origin, such as squalene or squalane;
- mineral oils, such as liquid paraffin, liquid petrolatum and isoparaffins;
- synthetic oils, in particular fatty acid esters, such as butyl myristate, propyl myristate, cetyl myristate, isopropyl palmitate, butyl stearate, hexadecyl stearate, isopropyl stearate, octyl stearate, isocetyl stearate, dodecyl oleate, hexyl laurate, propylene glycol dicaprylate, esters derived from lanolic acid, such as isopropyl lanolate or isocetyl lanolate, or fatty acid monoglycerides, diglycerides and triglycerides, such as glyceryl triheptanoate, alkyl benzoates, poly-α-olefins, polyolefins, such as polyisobutene, synthetic isoalkanes, such as isohexadecane or isododecane, perfluorinated oils and silicone oils.
- This oil can also be chosen from fatty acids, fatty alcohols, waxes of natural or synthetic origin and more generally still any fatty substance of vegetable, animal or synthetic origin.
- The wax is advantageously chosen from fatty substances which are solid at ambient temperature, such as, for example, beeswax; carnauba wax, candelilla wax; ouricury wax; Japan wax; cork fiber or sugarcane wax; paraffin waxes; lignite waxes; microcrystalline waxes; lanolin wax; ozokerite; polyethylene wax, hydrogenated oils; silicone waxes; vegetable waxes; fatty alcohols and fatty acids which are solid at ambient temperature; or glycerides which are solid at ambient temperature.
- The O/W emulsion in accordance with the invention can also comprise up to 10% by weight, for example from 0.1 to 10% by weight, of a stabilizing system.
- The stabilizing system can be composed of one or more compounds chosen from magnesium silicate; aluminum silicate; sodium silicate; xanthan gum; acacia gum; locust bean gum; scleroglucan gum; gellan gum; alginates; cellulose and cellulose derivatives; clays; starches and starch derivatives; carbomer; acrylic acid polymers and copolymers; acryloyldimethyl taurate polymers and copolymers; polyvinylpyrrolidone; acrylamide polymers and copolymers; or polyurethanes.
- The O/W emulsion can also comprise up to 30% by weight of one or more additives generally used in cosmetics and chosen from:
-
- coemulsifiers, such as, for example, fatty acids and fatty acid soaps; ethoxylated fatty acids; fatty acid esters; ethoxylated fatty acid esters, including polysorbates; polyglycerol esters; sucrose esters; alkylpolyglycosides with a chain length of greater than 12 carbon atoms; ethoxylated fatty alcohols; sulfated fatty alcohols; or phosphated fatty alcohols;
- preservatives generally used in cosmetics;
- fragrances or other additives with a scenting function (such as, in particular, essential oils and essential waxes);
- cosmetic active principles;
- cosolvents, such as, for example, glycerol; sorbitol; PEG; monopropylene glycol; butylene glycol; isoprene glycol; 2-methyl-, 3-propanediol; ethanol; or hexylene glycol;
- inorganic or organic bases, such as, for example, sodium hydroxide; potassium hydroxide; ammonia; triethanolamine; tetrahydroxypropylethylenediamine; trishydroxyaminomethane; or aminomethylpropanol;
- acids, in particular lactic acid, citric acid, acetic acid or tartaric acid.
- Thus, according to a fifth aspect, a subject matter of the present invention is an oil-in-water emulsion comprising at least one alkylpolyglycoside corresponding in particular to the formula (Ia), (Ib) or (II), and pigments and/or fillers.
- According to a sixth aspect of the present invention, a subject matter of the latter is an oil-in-water emulsion comprising from 0.5% to 10% by weight and more particularly from 1% to 5% by weight of the concentrate (C) as defined above, and inorganic pigments and/or fillers.
- The O/W emulsion in accordance with the invention can be prepared by processes known to a person skilled in the art, such as, for example, a process which comprises the following stages:
-
- a1) The aqueous phase comprising the fillers is milled using, for example, a bead mill or a device with a rotor-stator turbine mixer of Silverson type. This aqueous phase is subsequently heated to a temperature of 70 to 85° C.
- b1) At the same time, the fatty phase, comprising the emulsifier and the oils, is heated to an identical temperature of 70 to 85° C.
- c1) The compositions according to the invention are introduced without distinction into the fatty phase or the aqueous phase.
- d1) The two phases are subsequently mixed and emulsified using, for example, a rotor-stator emulsifying device (for example, a laboratory mixer of Silverson type). After emulsifying for a few minutes, the emulsion is cooled with moderate stirring.
- Another example of the process for the preparation of the O/W emulsion comprises the following stages:
-
- a2) The aqueous phase is heated to 70-85° C.
- b2) The fatty phase, comprising the fillers, emulsifier and the oils, is heated to an identical temperature of 70 to 85° C.
- c2) The compositions according to the invention are introduced without distinction into the fatty phase or the aqueous phase.
- d2) The two phases are subsequently mixed and emulsified using, for example, a rotor-stator emulsifying device (Silverson laboratory mixer). After emulsifying for a few minutes, the emulsion is cooled with moderate stirring.
- It is also possible, provided all the constituents of the emulsion are liquid at ambient temperature, to prepare said emulsion by a process devoid of heating.
- According to a final aspect of the present invention, a subject matter of the latter is a process for the preparation of a cosmetic or pharmaceutical oil-in-water emulsion for topical use, characterized in that between 0.2% and 10% by weight and more particularly between 0.5% and 5% by weight of a concentrate (C) as defined above is mixed with the other constituents of said composition.
- The invention is illustrated by the nonlimiting examples below. In these examples, the emulsions prepared are monitored:
-
- by monitoring using a microscope with a magnification of 40.
- by visual (macroscopic) monitoring of the stability of the emulsions with checking after 3 months of the appearance of the emulsions in the flask; smooth or granular appearance, glossy or matt appearance, monitoring of phenomena of phase separation, of release of pigments at the surface of the emulsion or of stratification of the pigments with a nonuniform visual effect. The optimum criteria are a glossy, perfectly smooth and homogeneous emulsion without phase separation or release or stratification of the pigments and fillers. The grading is as follows: + if all the criteria are satisfactory, +/− if at least one of the criteria is unsatisfactory, 0 if none of the criteria is satisfactory.
- by monitoring of the texture with the preparation, on a Plexiglas® sheet, of films calibrated to 120 μm and checking for the absence of agglomerates of fillers and pigments. The grading is as follows: + in the absence of specks 3 months after the manufacture of the emulsion, +/− in the presence of a few specks, 0 in the presence of numerous specks.
- In the case of the emulsions comprising fillers with the role of protecting from UV radiation, the protection factor is evaluated according to the method described below:
- The protection factor is evaluated in vitro by measuring the absorbing power with respect to UV-B and UV-A radiation after spreading a film of emulsion over a support which models the skin surface.
- The emulsion is spread in a calibrated way (2 mg/cm2) over a prehydrated collagen matrix sold under the name Vitroskin® by IMS. After drying the film for a period of 15 minutes, the coated support is subjected to exposure to UV radiation using a Labsphere® spectro-photometer. The sun protection coefficient is calculated by the software of the device according to the Diffey formula from the transmission of the UV radiation over the whole spectrum between 280 and 400 nm.
- In view of the role of UV-A radiation in the onset of skin cancers, the relative importance of the protection with respect to UV-A radiation is calculated by producing the ratio of the area under the absorbance curve in the UV-A spectrum to the area under the absorbance curve in the UV-B spectrum. A UV-A/UV-B ratio of >0.6 is recommended for effective protection with respect to UV-A radiation.
- 908.4 g of 1,10-decanediol, sold by Cognis under the name Speziol® C10/2, are gradually introduced into a two liter glass reactor. The reactor is brought to a temperature of 90° C., so as to effectively melt the 1,10-decanediol, stirring is started and 390.0 g of xylose are dispersed in the presence of a catalytic amount of sulfuric acid. After two hours at 80° C./85° C. under vacuum and neutralization with sodium hydroxide, the product exhibits the following analytical characteristics:
-
- Appearance (visual): off-white solid
- Color of a molten product (NFT 20 030): 1 vcs
- pH of a 5% dispersion (NFT 73 206): 7.8
- Water content: 0.47%
- Acid number (NFT 60 204): 0.25
- Hydroxyl number: 689
- Residual 1,10-decanediol: 37.3%
-
-
- The procedure of example 1 is repeated but 500.6 g of 1,10-decanediol being reacted with 430 g of xylose to result in a product exhibiting the following analytical characteristics:
- Appearance (visual): black solid
- pH of a 5% dispersion (NFT 73 206): 7.8
- Water content: 2.0%
- Acid number (NFT 60 204): 4.9
- Hydroxyl number: 726
- Residual 110-decanediol: 9.0%
- O/W emulsions are prepared which comprise the following ingredients:
-
A Emulsifier 02.50% C12-C15 Alkyl benzoate 20.00% Titanium oxide (20 nm/dimethicone coating) 10.00% B Cyclomethicone 05.00% Glycerol 07.00% C Tetrasodium EDTA 00.20% Water q.s. for 100% Carbomer ® 00.05% Tromethamine q.s. pH > 7 Magnesium silicate/Aluminum silicate 01.00% Xanthan gum 00.15% D DL-α-Tocopherol 00.05% Preservatives q.s. - The Carbomer®, the magnesium silicate/aluminum silicate and the xanthan gum are dispersed in the aqueous phase. The aqueous phase is heated to 70-85° C. and then the EDTA and the tromethamine are added.
- The fatty phase, comprising the titanium oxide, the emulsifier and the C12-C15 alkyl benzoate, is heated to an identical temperature of 70 to 85° C. The cyclo-methicone and the glycerol are added to this hot fatty phase.
- The two phases are subsequently mixed and emulsified using a rotor-stator emulsifying device (Silverson laboratory mixer). After emulsifying for a few minutes, the emulsion is cooled with moderate stirring.
- The tocopherol and the preservatives are added at the end of cooling with moderate stirring.
- The results are presented in table 1.
-
TABLE 1 Microscopic Texture Brookfield appearance of the viscosity Stability of the Emulsifier emulsion (mPa · s) at AT emulsion Decylglucoside Smooth 9500 >3 months Fine and (p = 1.45) milk homogeneous Decylglucoside Smooth 7000 >3 months Fine and (p = 1.9) milk homogeneous Example 1 Smooth 9000 >3 months Fine and milk homogeneous Ethylhexyl- Smooth 10 500 >3 months Fine end glucoside milk homogeneous (p = 1.45) - The procedure of example 3 is repeated by using alkylpolyglucoside-based emulsifiers having a chain with 4 and 12 carbon atoms and ethoxylated emulsifiers. The results are presented in table 2.
-
TABLE 2 Microscopic Texture of Brookfield appearance the viscosity Stability of the Emulsifier emulsion (mPa · s) at AT emulsion Cetearyl- Granular 43 000 >3 months agglomerates glucoside cream (p = 1.25) Dodecyl- Granular 7000 <7 days agglomerates glucoside milk (p = 1.43) Butyl- Non- — — — glucoside emulsifying (p = 1.45) Laureth-7 Granular 15 000 <3 months agglomerates Deceth-4 Granular 8000 <7 days agglomerates milk Deceth-5 Granular 11 000 <7 days agglomerates cream Deceth-3 Non- — — — emulsifying - It is not possible with butylglucoside to obtain an emulsion and dodecylglucoside results in emulsions which are less stable than those obtained with the alkylglucosides according to the invention. Cetearyl-glucoside and dodecylglucoside give agglomerates. The ethoxylated nonionic surfactants are less effective than the alkylpolyglycosides according to the invention.
- An emulsion is prepared which comprises the following ingredients:
-
A Emulsifier 2.50% Diisopropyl adipate 25.00% Titanium oxide (20 nm/dimethicone coating) 10.00% Zinc oxide (50 nm) 02.00% B Cyclomethicone 03.00% Glycerol 07.00% C Tetrasodium EDTA 00.20% Water q.s. for 100% Carbomer ® 00.05% Tromethamine q.s. pH > 7 Magnesium silicate/Aluminum silicate 01.00% Xanthan gum 00.15% D DL-α-Tocopherol 00.05% Preservatives q.s. - The Carbomer®, the magnesium silicate/aluminum silicate and the xanthan gum are dispersed in the aqueous phase. The aqueous phase is heated to 70-85° C. and then the EDTA and the tromethamine are added.
- The fatty phase, comprising the titanium oxide and the zinc oxide, the emulsifier and the oil, is heated to an identical temperature of 70 to 85° C. The cyclomethicone and the glycerol are added to this hot fatty phase.
- The two phases are subsequently mixed and emulsified using a rotor-stator emulsifying device (Silverson laboratory mixer). After emulsifying for a few minutes, the emulsion is cooled wish moderate stirring.
- The tocopherol and the preservatives are added at the end of cooling with moderate stirring.
- The results are presented in table 3.
-
TABLE 3 (PEG 100 stearate + glycerol stearate) 1.7% + DEA cetyl Dodecyl- Decylglucoside phosphate 0.8% glucoside Emulsifier (invention) (comparative) (comparative) Texture of the Smooth milk Granular milk Granular milk emulsion >1 year at 1 month at 1 day Microscopic Fine and Onset of Onset of appearance homogeneous agglomerates agglomerates dispersion beyond 15 days at 1 day >1 year Stability AT >1 year >1 year <1 month 40° C. >6 months <3 months <1 month 50° C. >1 month <15 days <1 month Protection factor 7 days 14 15 8 1 month 16 8 — 1 year 15 5 — UV-A/UV-B Ratio 7 days 0.9 0.9 0.55 1 year 0.9 0.6 — - Decylglucoside, the emulsifier according to the invention, makes it possible, in contrast to the comparative emulsifiers, to retain a fine and homogeneous dispersion of the filters during the storage with consequently a visual texture which remains perfectly smooth over time and a stable protection factor, both in the UV-B spectrum and in the UV-A spectrum, as is illustrated by the value of the factor and that of the UV-A/UV-B ratio.
- An emulsion is prepared which comprises the following ingredients:
-
A Emulsifier 03.00% Caprylic/capric triglycerides 20.00% Zinc oxide 05.00% Glycerol 05.00% C Tetrasodium EDTA 00.10% Water q.s. for 100% Sepigel ® 305 01.50% Tromethamine q.s. pH > 7 Magnesium silicate/Aluminum silicate 01.00% Xanthan gum 00.15% D DL-α-Tocopherol 00.05% Preservatives q.s. - The Sepigel® 305 (polyacrylamide and C11-C13 isoparaffin and laureth-7; sold by Seppic), the magnesium silicate/aluminum silicate and the xanthan gum are dispersed in the aqueous phase. The EDTA and the tromethamine are added to the aqueous phase.
- The fatty phase is produced by simple mixing of the constituents without heating.
- The two phases are subsequently mixed and emulsified using a rotor-stator emulsifying device (Silverson laboratory mixer). The tocopherol and the preservatives are added with moderate stirring.
- The results are presented in table 4.
-
TABLE 4 Emulsifier Decylglucoside Octylxyloside Texture of the Smooth milk Smooth milk emulsion Microscopic Fine and Fine and appearance homogeneous homogeneous dispersion dispersion Stability AT >1 month >1 month 40° C. >1 month >1 month 50° C. >1 month >1 month Protection factor 1 month 9 6 1 year 8.5 6 -
-
A Emulsifier 2.50% Isononyl isononanoate 08.00% Diisopropyl dimer dilinoleate 08.00% B Cyclomethicone 04.00% Sepigel ® 305 01.50% C Water q.s. for 100% Micropearl ® M305 02.00% (crosslinked methyl methacrylate polymer) Tetrasodium EDTA 00.50% D Pigment paste Butylene glycol 04.00% Polyethylene glycol 400 04.00% Titanium dioxide, E171 07.00% Talc, Luzenac 000C 02.00% Yellow iron oxide, 00.80% Sicovit yellow 10 E172 Red iron oxide, Sicovit red 30 E172 00.30% Black iron oxide, Sicovit black 00.05% Water 20.00% NaOH q.s. for pH > 8 E Preservatives q.s. Fragrance 00.20% - The pigment paste is milled beforehand on a bead mill.
- The water is heated to 70-75° C. and then the Micropearl®, the EDTA and the pigment paste are added to the hot aqueous phase.
- The fatty phase, comprising the emulsifier and the oils, is heated to a temperature of 70 to 75° C. The cyclomethicone and the Sepigel® 305 are added to this hot fatty phase.
- The two phases are subsequently mixed and emulsified using a rotor-stator emulsifying device (Silverson laboratory mixer). After emulsifying for a few minutes, the emulsion is cooled with moderate stirring.
- The preservatives and the fragrance are added at the end of cooling with moderate stirring.
- The results are presented in table 5.
-
TABLE 5 Sodium stearate 1.7% + Cetearyl- Steareth-10 Decylglucoside glucoside 0.8% Emulsifier (invention) (comparative) (comparative) Visual + +/− +/− appearance after 3 months Texture after + +/− 0 3 months Rendering of the color on application (Minolta CR300 chromameter) after 3 months Parameter L 68.3 (±0.7) 70.1 (±0.4) 73.4 (±0.6) Parameter a 2.3 (±0.6) 18.2 (±2.3) 16.5 (±2.7) Parameter b 30 (±0.9) 23.7 (±1.5) 20.2 (±2.8) - The fineness of the dispersion of the fillers is reflected by an improvement in the spreading over the skin, by uniform color and by a better rendering of the color on the skin: decrease in the whiteness (parameter L) and an enhancement in the colored parameters a (red hue) and b (blue hue). The non-uniformity in the color with the comparative examples is clearly apparent with regard to the standard deviation values for a and b, which are higher than in the example according to the invention.
-
-
A Isononyl isononanoate 08.00% Triisostearyl citrate 08.00% Simulgel ® NS 04.00% B Water q.s. for 100% Tetrasodium EDTA 00.05% Emulsifier 0.8% C Pigment paste Butylene glycol 04.00% Polyethylene glycol 400 04.00% Titanium dioxide, E171 05.00% Yellow iron oxide, 00.80% Sicovit yellow 10 E172 Red iron oxide, Sicovit red 30 E172 00.30% Black iron oxide, Sicovit black 00.05% Water 20.00% NaOH q.s. for pH > 8 D Preservatives q.s. Fragrance 00.20% - The pigment paste is milled beforehand on a bead mill.
- The Simulgel® NS (sodium acryloyldimethyl taurate/hydroxyethyl acrylate copolymer and squalane and polysorbate 80; sold by Seppic) is mixed with the oils. The aqueous phase B is added to phase A to form the cream gel. The pigment paste (phase C) and subsequently phase D are then added directly to the cream gel with moderate stirring.
- The results are presented in table 6.
-
TABLE 6 Decylglucoside Laureth-7 Emulsifier (invention) (comparative) Visual appearance + 0 After 3 months Texture after + 0 3 months - It will be understood that many additional changes in the details, materials, steps and arrangement of parts, which have been herein described in order to explain nature of the invention, may be made by those skilled in the art within the principle and scope of the invention as expressed in the appended claims. Thus, the present invention is not intended to be limited to the specific embodiments in the examples given above.
Claims (5)
1. An alkylpolyglycoside composition of formula (Ia) or (Ib)
HO—RO—X(r (Ia)
(X)aO—RO—(X)t (Ib)
HO—RO—X(r (Ia)
(X)aO—RO—(X)t (Ib)
wherein:
a) X represents the residue of a C5 or C6 sugar;
b) R represents an alkylene or alkylidene group having from 6 to 12 carbon atoms; and
c) r, s, and t represent the mean degree of polymerization of each sugar residue, and are greater than 1 and less than or equal to 5.
2. The alkylpolyglycoside composition of claim 1 , wherein X represents the residue of glucose or xylose.
3. A method of preparing an oil-in-water emulsion, containing inorganic fillers and/or pigments, comprising the step of adding an emulsifying agent which comprises said at least one alkylpolyglycoside of formula (Ia) or (Ib) of claim 1 .
4. An oil-in-water emulsion comprising:
inorganic pigments and/or fillers; and
at least one compound wherein the compound is of the formula (Ia) or (Ib) of claim 1 .
5. The emulsion of claim 4 , which is an antisun or a makeup emulsion.
Priority Applications (1)
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US12/511,762 US20090291052A1 (en) | 2001-10-25 | 2009-07-29 | Use of alkylpolyglycosides as emulsifying agents for the preparation of oil-in-water emulsions comprising inorganic fillers or pigments, and oil-in-water emulsions comprising such alkylpolyglycosides |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0113808A FR2831539B1 (en) | 2001-10-25 | 2001-10-25 | USE OF ALKYLPOLYGLYCOSIDES AS EMULSIFYING AGENTS FOR THE PREPARATION OF OIL-IN-WATER EMULSION CONTAINING MINERAL FILLERS OR PIGMENTS, AND OIL-IN-WATER EMULSIONS CONTAINING SUCH ALKYLPOLYGLYCOSIDES |
FRFR01/13808 | 2001-10-25 | ||
US10/493,726 US7670614B2 (en) | 2001-10-25 | 2002-10-22 | Use of alkylpolyglycosides as emulsifying agents for the preparation oil-in-water emulsions containing mineral pigments or fillers and the oil-in-water emulsions containing such alkylpolyglycosides |
PCT/FR2002/003609 WO2003035657A2 (en) | 2001-10-25 | 2002-10-22 | Use of alkylpolyglycosides as emulsifying agents for the preparation of oil-in-water emulsions containing mineral pigments or fillers and the oil-in-water emulsions containing such alkylpolyglycosides |
US12/511,762 US20090291052A1 (en) | 2001-10-25 | 2009-07-29 | Use of alkylpolyglycosides as emulsifying agents for the preparation of oil-in-water emulsions comprising inorganic fillers or pigments, and oil-in-water emulsions comprising such alkylpolyglycosides |
Related Parent Applications (2)
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PCT/FR2002/003609 Division WO2003035657A2 (en) | 2001-10-25 | 2002-10-22 | Use of alkylpolyglycosides as emulsifying agents for the preparation of oil-in-water emulsions containing mineral pigments or fillers and the oil-in-water emulsions containing such alkylpolyglycosides |
US10/493,726 Division US7670614B2 (en) | 2001-10-25 | 2002-10-22 | Use of alkylpolyglycosides as emulsifying agents for the preparation oil-in-water emulsions containing mineral pigments or fillers and the oil-in-water emulsions containing such alkylpolyglycosides |
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US12/511,762 Abandoned US20090291052A1 (en) | 2001-10-25 | 2009-07-29 | Use of alkylpolyglycosides as emulsifying agents for the preparation of oil-in-water emulsions comprising inorganic fillers or pigments, and oil-in-water emulsions comprising such alkylpolyglycosides |
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US (2) | US7670614B2 (en) |
EP (1) | EP1444243A2 (en) |
JP (2) | JP4611630B2 (en) |
CN (1) | CN1305887C (en) |
AU (1) | AU2002362981A1 (en) |
FR (1) | FR2831539B1 (en) |
WO (1) | WO2003035657A2 (en) |
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FR2883733B1 (en) * | 2005-03-30 | 2012-02-03 | Lyofal | LYOPHILIZED MAKE-UP PRODUCT, COMPOSITIONS AND METHOD OF MANUFACTURING THE SAME |
FR2898810B1 (en) * | 2006-03-24 | 2012-08-17 | Seppic Sa | NOVEL METHOD FOR ENHANCING OCULAR TOLERANCE OF FOAMING AND / OR DETERGENT COMPOSITIONS FOR SKIN USE |
FR2900413B1 (en) | 2006-04-28 | 2008-06-13 | Seppic Sa | NOVEL PROCESS FOR IMPROVING THE FOAMING PROPERTIES OF CLEANING AND / OR FOAMING FORMULATIONS FOR TOPICAL USE |
FR2928376B1 (en) * | 2008-03-06 | 2011-05-20 | Agro Ind Rech S Et Dev | DETERGENT COMPOSITIONS BASED ON ALKYL POLYGLUCOSIDES |
EA021066B1 (en) * | 2008-03-11 | 2015-03-31 | Латексфалт Б.В. | Emulsion comprising non-modified scleroglucan as a stabiliser and use thereof |
FR2959140A1 (en) * | 2010-04-23 | 2011-10-28 | Agro Ind Rech S Et Dev Ard | FACILITATED PREPARATIONS OF VESICLES USING ALKYL POLY-PENTOSIDES AND USES THEREOF |
FR2981568B1 (en) * | 2011-10-20 | 2013-12-13 | Lvmh Rech | COSMETIC OR DERMATOLOGICAL COMPOSITION COMPRISING ALKYL POLYPENTOSIDE VESICLES AND PROCESS FOR PREPARING THE SAME |
MX2014009438A (en) * | 2012-02-14 | 2015-06-23 | Oreal | Cosmetic composition and process for coloring and bleaching of human keratin fibers. |
JP2014091716A (en) * | 2012-11-05 | 2014-05-19 | Kao Corp | Method of producing glycoside compound |
CN109803635A (en) * | 2016-10-11 | 2019-05-24 | 帝斯曼知识产权资产管理有限公司 | Cosmetic composition |
ES2951597T3 (en) * | 2019-09-19 | 2023-10-23 | Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic | Perfuming compositions, stable and having good spray properties |
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-
2002
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- 2002-10-22 CN CNB028211499A patent/CN1305887C/en not_active Expired - Fee Related
- 2002-10-22 JP JP2003538172A patent/JP4611630B2/en not_active Expired - Fee Related
- 2002-10-22 EP EP02790532A patent/EP1444243A2/en not_active Withdrawn
- 2002-10-22 US US10/493,726 patent/US7670614B2/en not_active Expired - Fee Related
- 2002-10-22 WO PCT/FR2002/003609 patent/WO2003035657A2/en active Application Filing
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2009
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US20040241127A1 (en) | 2004-12-02 |
JP2005514340A (en) | 2005-05-19 |
US7670614B2 (en) | 2010-03-02 |
JP2010077132A (en) | 2010-04-08 |
JP4611630B2 (en) | 2011-01-12 |
CN1575296A (en) | 2005-02-02 |
WO2003035657A3 (en) | 2004-01-22 |
AU2002362981A1 (en) | 2003-05-06 |
CN1305887C (en) | 2007-03-21 |
FR2831539B1 (en) | 2005-02-11 |
WO2003035657A2 (en) | 2003-05-01 |
FR2831539A1 (en) | 2003-05-02 |
EP1444243A2 (en) | 2004-08-11 |
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