CH623236A5 - Dispersion of lipid spherules - Google Patents
Dispersion of lipid spherules Download PDFInfo
- Publication number
- CH623236A5 CH623236A5 CH42980A CH42980A CH623236A5 CH 623236 A5 CH623236 A5 CH 623236A5 CH 42980 A CH42980 A CH 42980A CH 42980 A CH42980 A CH 42980A CH 623236 A5 CH623236 A5 CH 623236A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dispersion
- spherules
- encapsulated
- lipid
- phase
- Prior art date
Links
- 239000006185 dispersion Substances 0.000 title claims description 58
- 150000002632 lipids Chemical class 0.000 title claims description 45
- 239000012071 phase Substances 0.000 claims description 31
- 239000008346 aqueous phase Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 239000013543 active substance Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002537 cosmetic Substances 0.000 claims description 9
- -1 lipid compound Chemical class 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 238000002604 ultrasonography Methods 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000000975 dye Substances 0.000 claims description 6
- 235000013305 food Nutrition 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 229920005654 Sephadex Polymers 0.000 claims description 4
- 239000012507 Sephadex™ Substances 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 4
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 230000035515 penetration Effects 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 claims description 2
- 208000001840 Dandruff Diseases 0.000 claims description 2
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 claims description 2
- 229940124091 Keratolytic Drugs 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 210000004381 amniotic fluid Anatomy 0.000 claims description 2
- 230000001166 anti-perspirative effect Effects 0.000 claims description 2
- 239000003213 antiperspirant Substances 0.000 claims description 2
- 239000003212 astringent agent Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 230000002951 depilatory effect Effects 0.000 claims description 2
- 229940120503 dihydroxyacetone Drugs 0.000 claims description 2
- 238000005538 encapsulation Methods 0.000 claims description 2
- UQPHVQVXLPRNCX-UHFFFAOYSA-N erythrulose Chemical compound OCC(O)C(=O)CO UQPHVQVXLPRNCX-UHFFFAOYSA-N 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 claims description 2
- 235000019634 flavors Nutrition 0.000 claims description 2
- 239000003349 gelling agent Substances 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 229960005150 glycerol Drugs 0.000 claims description 2
- 230000035876 healing Effects 0.000 claims description 2
- 239000003906 humectant Substances 0.000 claims description 2
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims description 2
- 229960000367 inositol Drugs 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 230000001530 keratinolytic effect Effects 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 239000003605 opacifier Substances 0.000 claims description 2
- 229940059574 pentaerithrityl Drugs 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 229940079889 pyrrolidonecarboxylic acid Drugs 0.000 claims description 2
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 2
- 229960002920 sorbitol Drugs 0.000 claims description 2
- 239000000516 sunscreening agent Substances 0.000 claims description 2
- 230000001256 tonic effect Effects 0.000 claims description 2
- 239000003643 water by type Substances 0.000 claims description 2
- 239000002502 liposome Substances 0.000 claims 10
- 239000007788 liquid Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000000926 separation method Methods 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 238000010828 elution Methods 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 230000008520 organization Effects 0.000 claims 1
- 150000003904 phospholipids Chemical class 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000010409 thin film Substances 0.000 claims 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- 239000003995 emulsifying agent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 239000002353 niosome Substances 0.000 description 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 description 1
- 102000019197 Superoxide Dismutase Human genes 0.000 description 1
- 108010012715 Superoxide dismutase Proteins 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C09K23/34—Higher-molecular-weight carboxylic acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
- A61K9/1277—Processes for preparing; Proliposomes
-
- 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
- A61K8/14—Liposomes; Vesicles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers with substantial amounts of non-phosphatidyl, i.e. non-acylglycerophosphate, surfactants as bilayer-forming substances, e.g. cationic lipids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/04—Preparations for care of the skin for chemically tanning the skin
-
- 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
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/542—Macromolecular compounds
- C09K19/544—Macromolecular compounds as dispersing or encapsulating medium around the liquid crystal
-
- 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
-
- 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
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K2019/523—Organic solid particles
-
- 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
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K2019/528—Surfactants
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Biophysics (AREA)
- Birds (AREA)
- Crystallography & Structural Chemistry (AREA)
- Molecular Biology (AREA)
- Medicinal Preparation (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Cosmetics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Colloid Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Fats And Perfumes (AREA)
Description
La présente invention, qui vise à remédier aux inconvénients précités, a pour objet: a) la dispersion de sphérules lipidiques définie dans la revendication 1 et b) le procédé défini dans la revendication 9, pour l'obtention d'une telle dispersion. The object of the present invention, which aims to remedy the aforementioned drawbacks, is: a) the dispersion of lipid spherules defined in claim 1 and b) the process defined in claim 9, for obtaining such a dispersion.
Les sphérules de la dispersion selon l'invention peuvent encapsuler des substances actives avec un fort rendement d'encapsulation. Au sens de la présente description, le mot encapsuler est utilisé pour indiquer que l'on dispose une phase aqueuse à l'intérieur d'une capsule constituée par les sphérules lipidiques. The spherules of the dispersion according to the invention can encapsulate active substances with a high encapsulation yield. Within the meaning of the present description, the word encapsulate is used to indicate that there is an aqueous phase inside a capsule constituted by the lipid spherules.
Dans un mode préféré de réalisation, la phase aqueuse à encapsuler est une solution aqueuse de substance active; les substances actives de la phase aqueuse à encapsuler sont des produits à action cosmétique, pharmaceutique ou alimentaire ; la phase continue de la dispersion est une phase aqueuse; la proportion du poids des sphérules par rapport au poids de la phase continue de la dispersion est comprise entre 0,01 et 0,5 environ ; la phase continue de la dispersion est avantageusement iso-osmotique par rapport à la phase aqueuse encapsulée dans les sphérules. In a preferred embodiment, the aqueous phase to be encapsulated is an aqueous solution of active substance; the active substances of the aqueous phase to be encapsulated are products with cosmetic, pharmaceutical or food action; the continuous phase of the dispersion is an aqueous phase; the proportion of the weight of the spherules relative to the weight of the continuous phase of the dispersion is between 0.01 and 0.5 approximately; the continuous phase of the dispersion is advantageously iso-osmotic with respect to the aqueous phase encapsulated in the spherules.
Les substances actives, qui peuvent être encapsulées dans les sphérules ci-dessus définies, sont extrêmement variées et correspondent à celles qui seront indiquées plus loin pour la mise en œuvre du procédé selon l'invention. Il en résulte que les compositions peuvent être utilisées dans des domaines variés et, en particulier, dans le domaine de l'industrie alimentaire, de l'industrie pharmaceutique ou de l'industrie cosmétique. The active substances, which can be encapsulated in the spherules defined above, are extremely varied and correspond to those which will be indicated below for the implementation of the method according to the invention. As a result, the compositions can be used in various fields and, in particular, in the field of the food industry, the pharmaceutical industry or the cosmetic industry.
Les dispersions aqueuses définies ci-dessus ont un intérêt tout particulier en cosmétique, en raison du fait que l'utilisation de sphérules de grandes dimensions permet de réduire les risques de passage de ces préparations à travers la peau. The aqueous dispersions defined above are of particular interest in cosmetics, due to the fact that the use of large spherules makes it possible to reduce the risks of passage of these preparations through the skin.
Il convient de noter que l'utilisation des dispersions aqueuses selon l'invention en cosmétique présente un avantage considérable It should be noted that the use of the aqueous dispersions according to the invention in cosmetics has a considerable advantage.
623 236 623,236
par rapport à l'utilisation bien connue des émulsions. En effet, lorsque l'on désire utiliser des préparations contenant à la fois des corps gras et de l'eau, il est nécessaire, pour assurer la stabilité de l'émulsion, d'utiliser des composés amphiphiles émulsionnants pour assurer la stabilité des dispersions. Il est connu que certains émulsionnants peuvent être relativement irritants lorsqu'ils sont appliqués sur la peau. On a découvert, au cours des travaux relatifs à la présente invention, que cet effet des émulsionnants, pour une structure chimique donnée, dépend considérablement de la forme sous laquelle ils sont appliqués. Ainsi, on a pu mettre en évidence le fait qu'une émulsion eau/huile composée de 42% de perhydrosqualène, de 8% d'émulsionnant et de 50% d'eau est fortement irritante, alors qu'une dispersion aqueuse à 8% du même émulsionnant a un indice d'irritation pratiquement insignifiant et que le perhydrosqualène est absolument inoffensif. Il en résulte qu'il y a une synergie d'irritation, lorsqu'on a en présence un émulsionnant et une phase huile. Les dispersions aqueuses selon l'invention permettent d'éviter l'utilisation simultanée d'un émulsionnant et d'une huile, ce qui constitue un progrès important dans le domaine de la cosmétique. compared to the well known use of emulsions. In fact, when it is desired to use preparations containing both fatty substances and water, it is necessary, to ensure the stability of the emulsion, to use amphiphilic emulsifying compounds to ensure the stability of the dispersions . It is known that certain emulsifiers can be relatively irritating when applied to the skin. It has been discovered, in the course of work relating to the present invention, that this effect of emulsifiers, for a given chemical structure, depends considerably on the form in which they are applied. Thus, we were able to highlight the fact that a water / oil emulsion composed of 42% perhydrosqualene, 8% emulsifier and 50% water is highly irritating, while an aqueous dispersion at 8% of the same emulsifier has a practically insignificant index of irritation and that perhydrosqualene is absolutely harmless. As a result, there is a synergy of irritation when an emulsifier and an oil phase are present. The aqueous dispersions according to the invention make it possible to avoid the simultaneous use of an emulsifier and an oil, which constitutes significant progress in the field of cosmetics.
Il convient de noter que l'on peut ajouter aux dispersions de sphérules selon l'invention différents produits auxiliaires ayant pour but d'en modifier la présentation ou les caractères organoleptiques, tels que des opacifiants, des gélifiants, des arômes, des parfums ou des colorants. It should be noted that it is possible to add to the dispersions of spherules according to the invention various auxiliary products intended to modify the presentation or the organoleptic characters, such as opacifiers, gelling agents, flavors, perfumes or dyes.
De façon générale, l'intérêt des dispersions selon l'invention réside dans le fait qu'elles permettent d'introduire des substances hydrophiles dans un milieu essentiellement lipophile. Il en résulte que, dans ces conditions, celles-ci se trouvent masquées, d'où un effet de protection vis-à-vis des différents agents d'altération possibles: oxydants, sucs digestifs et, plus généralement, composés réactifs vis-à-vis des substances encapsulées. La pénétration et/ou la fixation des substances actives peuvent être modulées par variation de la taille des globules et de leur charge électrique. Leur action peut également être différée (effet retard). En outre, le fait qu'elles soient masquées permet de supprimer ou d'altérer sensiblement leurs caractères organoleptiques, en particulier le goût. Enfin, les lipides utilisés dans ces préparations possèdent, par eux-mêmes, une action bénéfique, par exemple émollience, lubrification, lustrage. Generally, the advantage of the dispersions according to the invention lies in the fact that they make it possible to introduce hydrophilic substances into an essentially lipophilic medium. It follows that, under these conditions, these are masked, hence a protective effect with respect to the various possible alteration agents: oxidants, digestive juices and, more generally, reactive compounds with respect to -vis encapsulated substances. The penetration and / or fixation of active substances can be modulated by varying the size of the globules and their electrical charge. Their action can also be postponed (delay effect). In addition, the fact that they are masked makes it possible to suppress or substantially alter their organoleptic characters, in particular the taste. Finally, the lipids used in these preparations have, by themselves, a beneficial action, for example emollience, lubrication, polishing.
Dans un mode préféré de mise en œuvre du procédé selon l'invention, le rapport pondéral entre la quantité de phase aqueuse à encapsuler mise en contact avec les lipides et la quantité de lipides formant la phase lamellaire est compris entre 0,1 environ et 3 environ ; la phase aqueuse à encapsuler peut être de l'eau ou une solution aqueuse de produit actif ; le rapport pondéral de la quantité de phase de dispersion, que l'on ajoute, à la quantité de phase lamellaire, que l'on disperse, est compris entre 2 environ et 100 environ; la phase de dispersion et la phase aqueuse à encapsuler sont, de préférence, iso-osmotiques; la phase de dispersion peut avantageusement être une solution aqueuse; l'agitation réalisée comme dernière phase du procédé est obtenue au moyen d'un agitateur à secousses; le procédé est mis en œuvre à température ambiante ou à une température plus élevée si le lipide est solide à température ambiante; dans le cas où l'on désire que les sphérules obtenues aient un diamètre moyen inférieur à 1000 Â, on peut soumettre la dispersion de sphérules à un traitement aux ultra-sons. In a preferred embodiment of the process according to the invention, the weight ratio between the quantity of aqueous phase to be encapsulated brought into contact with the lipids and the quantity of lipids forming the lamellar phase is between approximately 0.1 and 3 about ; the aqueous phase to be encapsulated can be water or an aqueous solution of active product; the weight ratio of the quantity of dispersion phase, which is added, to the quantity of lamellar phase, which is dispersed, is between approximately 2 and approximately 100; the dispersion phase and the aqueous phase to be encapsulated are preferably iso-osmotic; the dispersion phase can advantageously be an aqueous solution; the agitation carried out as the last phase of the process is obtained by means of a shaker; the process is carried out at room temperature or at a higher temperature if the lipid is solid at room temperature; if it is desired that the spherules obtained have an average diameter of less than 1000 Å, the dispersion of spherules may be subjected to an ultrasound treatment.
Pour former la phase lamellaire, on peut utiliser un seul lipide ou un mélange de lipides. Le (ou les) lipide(s), que l'on utilise, comporte(nt) une chaîne lipophile longue comportant de 12 à 30 atomes de carbone, saturée ou insaturée, ramifiée ou linéaire; on peut, en particulier, choisir des chaînes oléique, lanolique, tétra-décylique, hexadécylique, isostéarylique, laurique ou alcoylphényl. Comme lipide formant la phase lamellaire, on peut avantageusement choisir un composé amphotère comportant deux chaînes lipo-philes ou une association de deux ions organiques à longue chaîne de signes opposés. To form the lamellar phase, a single lipid or a mixture of lipids can be used. The lipid (s) which are used comprises (s) a long lipophilic chain comprising from 12 to 30 carbon atoms, saturated or unsaturated, branched or linear; in particular, it is possible to choose oleic, lanolic, tetra-decyl, hexadecyl, isostearyl, lauric or alkylphenyl chains. As the lipid forming the lamellar phase, it is advantageous to choose an amphoteric compound comprising two lipophilic chains or a combination of two long-chain organic ions of opposite signs.
On peut utiliser une phase aqueuse à encapsuler comportant des substances actives de toutes sortes et, en particulier, des substances ayant un intérêt pharmaceutique, ou alimentaire, ou des substances It is possible to use an aqueous phase to be encapsulated comprising active substances of all kinds and, in particular, substances having a pharmaceutical or food interest, or substances
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ayant une activité cosmétique. Les substances actives peuvent être, par exemple, en ce qui concerne la cosmétique; les produits destinés aux soins de la peau et du cheveu, par exemple des humectants, tels que la glycérine, le sorbitol, le pentaérythritol, l'inositol, l'acide pyrrolidonecarboxylique et ses sels; des agents de brunissage artificiel tels que la dihydroxyacétone, l'érythrulose, la glycéral-déhyde, les y-dialdéhydes tels que l'aldéhyde tartrique (ces produits pouvant être éventuellement associés à des colorants); des agents antisolaires hydrosolubles; des antiperspirants, des déodorants, des astringents, des produits rafraîchissants, toniques, cicatrisants, kératolytiques, dépilatoires; des eaux parfumées; des extraits de tissus animaux ou végétaux, tels que protéines, Polysaccharides, liquide amniotique; des colorants hydrosolubles, des agents antipelliculaires, des agents antiséborrhéiques, des oxydants (agents de décoloration) comme l'eau oxygénée, des réducteurs tels que l'acide thioglycolique et ses sels. Comme substances actives pharmaceutiques, on peut citer les vitamines, les hormones, les enzymes, (par exemple, le superoxyde-dismutase), les vaccins, les antiinflammatoires (hydrocortisone, par exemple), les antibiotiques, les bactéricides. having cosmetic activity. The active substances can be, for example, with regard to cosmetics; products intended for skin and hair care, for example humectants, such as glycerin, sorbitol, pentaerythritol, inositol, pyrrolidonecarboxylic acid and its salts; artificial browning agents such as dihydroxyacetone, erythrulose, glyceral dehyde, γ-dialdehydes such as tartaric aldehyde (these products possibly being associated with dyes); water-soluble sunscreen agents; antiperspirants, deodorants, astringents, refreshing, tonic, healing, keratolytic, depilatory products; scented waters; extracts of animal or plant tissues, such as proteins, Polysaccharides, amniotic fluid; water-soluble dyes, anti-dandruff agents, antiseborrhoeic agents, oxidants (bleaching agents) such as hydrogen peroxide, reducers such as thioglycolic acid and its salts. As pharmaceutical active substances, mention may be made of vitamins, hormones, enzymes (for example, superoxide dismutase), vaccines, anti-inflammatories (for example hydrocortisone), antibiotics, bactericides.
Il est clair que l'on choisira, en fonction de la substance active contenue dans la phase aqueuse à encapsuler, des lipides susceptibles d'encapsuler de façon stable la phase aqueuse considérée. Pour que les lipides constituant la phase lamellaire donnent des sphérules stables, il est nécessaire qu'il y ait une interaction latérale suffisante entre les chaînes de lipides qui, placées côte à côte, constituent les couches ou feuillets des sphérules, c'est-à-dire que les forces de Van der Waals entre les chaînes assurent une cohésion suffisante des feuillets. Cette condition est satisfaite pour les lipides ayant les caractéristiques indiquées dans la définition générale du procédé ci-dessus donné. Les lipides pouvant être utilisés dans le procédé selon l'invention appartiennent à la classe des émulsionnants du type eau dans l'huile. It is clear that we will choose, depending on the active substance contained in the aqueous phase to be encapsulated, lipids capable of stably encapsulating the aqueous phase considered. In order for the lipids constituting the lamellar phase to give stable spherules, it is necessary that there is a sufficient lateral interaction between the lipid chains which, placed side by side, constitute the layers or sheets of the spherules, that is to say -to say that the Van der Waals forces between the chains ensure sufficient cohesion of the sheets. This condition is satisfied for lipids having the characteristics indicated in the general definition of the process given above. The lipids which can be used in the process according to the invention belong to the class of emulsifiers of the water in oil type.
Les exemples qui suivent illustrent l'invention. The following examples illustrate the invention.
Exemple 1 Example 1
Dans un ballon rond de 50 ml, on met en contact 300 mg de sphingomyéline avec 0,350 ml d'une solution 0,3M de glucose, et on homogénéise le mélange. L'expérience est faite à la température ambiante. In a 50 ml round flask, 300 mg of sphingomyelin is brought into contact with 0.350 ml of a 0.3M solution of glucose, and the mixture is homogenized. The experiment is carried out at room temperature.
On ajoute ensuite 5 ml d'une solution 0,145M de NaCl. Le ballon, placé sur une secoueuse, est agité énergiquement pendant 2 h. 5 ml of a 0.145M NaCl solution are then added. The flask, placed on a shaker, is shaken vigorously for 2 h.
La dispersion obtenue est laiteuse; le diamètre des sphérules est d'environ 2 ji. The dispersion obtained is milky; the diameter of the spherules is approximately 2 ji.
La dispersion peut être soumise aux ultra-sons durant 1 h afin de diminuer le diamètre des sphérules. The dispersion can be subjected to ultrasound for 1 hour in order to reduce the diameter of the spherules.
Exemple 2 Example 2
Dans un ballon rond de 50 ml, on mélange intimement 300mg du produit obtenu par distillation moléculaire, de formule générale: Into a 50 ml round flask, 300 mg of the product obtained by molecular distillation, of general formula, are intimately mixed:
r-/och2-ch voh r- / och2-ch voh
I I
\ ch2oh. \ ch2oh.
R étant le radical alkyle de l'alcool oléique et n étant égal à 2; 150 mg de cholestérol; 50 mg d'une amine de formule générale: R being the alkyl radical of oleic alcohol and n being equal to 2; 150 mg of cholesterol; 50 mg of an amine of general formula:
c2h5 c2h5
rc00(ch2ch20)n-ch2ch2n^ rc00 (ch2ch20) n-ch2ch2n ^
C2H5 C2H5
RCOO étant le reste du coprah et n étant un nombre compris entre 2 et 5, et on met en contact le mélange obtenu avec 0,5 ml d'une solution 0,3M de sorbitol; on homogénéise le mélange. L'expérience est faite à la température ambiante. RCOO being the remainder of the copra and n being a number between 2 and 5, and the mixture obtained is brought into contact with 0.5 ml of a 0.3M solution of sorbitol; the mixture is homogenized. The experiment is carried out at room temperature.
On ajoute ensuite 4 ml d'une solution 0,145M de KCl. Le ballon, placé sur une secoueuse, est agité énergiquement pendant 4 h. Then 4 ml of a 0.145 M KCl solution is added. The flask, placed on a shaker, is shaken vigorously for 4 h.
La dispersion obtenue est opalescente; le diamètre des sphérules est d'environ 2 |i. The dispersion obtained is opalescent; the diameter of the spherules is about 2 | i.
Exemple 3 Example 3
5 Dans un ballon rond de 50 ml, on met en contact 425 mg du produit, de formule générale: 5 In a 50 ml round flask, 425 mg of the product, of general formula:
r-/och2- ch- r- / och2- ch-
oh ch,oh. oh ch, oh.
R étant le radical alkyle de l'alcool oléique et n étant un nombre égal à 2, et 75 mg d'une amine de formule suivante: R being the alkyl radical of oleic alcohol and n being a number equal to 2, and 75 mg of an amine of the following formula:
R-/OCH2-CH 15 V CH2OH/n R- / OCH2-CH 15 V CH2OH / n
£ £
-OCH,CHOH-CH,N -OCH, CHOH-CH, N
R étant le radical oléyle et n ayant une valeur statistique moyenne de 1, avec 0,5 ml d'une solution 0,3M de glucose, et on homogénéise le mélange. L'expérience est faite à température ambiante. 20 On ajoute ensuite 4 ml d'une solution 0,145M (NaCl, KCl). Le ballon, placé sur une secoueuse, est agité énergiquement pendant 4 h. R being the oleyl radical and n having a mean statistical value of 1, with 0.5 ml of a 0.3M solution of glucose, and the mixture is homogenized. The experiment is carried out at room temperature. Then 4 ml of a 0.145 M solution (NaCl, KCl) is added. The flask, placed on a shaker, is shaken vigorously for 4 h.
La dispersion obtenue est opaque; le diamètre des sphérules est supérieur à 2 |i. The dispersion obtained is opaque; the diameter of the spherules is greater than 2 | i.
25 La dispersion peut être soumise aux ultra-sons, la taille des sphérules devenant alors inférieure au micron. The dispersion can be subjected to ultrasound, the size of the spherules then becoming less than one micron.
Exemple 4 Example 4
Dans un ballon rond de 50 ml, 300 mg de sphingomyéline sont 30 mis en contact avec 0,350 ml d'une solution 0,3M d'acide ascorbique, et on homogénéise le mélange. L'expérience est faite à température ambiante. In a 50 ml round flask, 300 mg of sphingomyelin are brought into contact with 0.350 ml of a 0.3M solution of ascorbic acid, and the mixture is homogenized. The experiment is carried out at room temperature.
On ajoute ensuite 2,650 ml d'une solution 0,145M de KCl. Le ballon, placé sur une secoueuse, est agité énergiquement pendant 4 h. 35 La dispersion obtenue est laiteuse; le diamètre des sphérules est d'environ 2 |i. 2.650 ml of a 0.145 M solution of KCl are then added. The flask, placed on a shaker, is shaken vigorously for 4 h. The dispersion obtained is milky; the diameter of the spherules is about 2 | i.
Si on le désire, la dispersion peut être filtrée sur colonne de gel Sephadex G 50 coarse gonflé dans une solution 0,145M de KCl. If desired, the dispersion can be filtered on a column of Sephadex G 50 coarse gel swollen in 0.145 M KCl solution.
40 40
Exemple 5 Example 5
Dans un ballon rond de 50 ml, 142 mg du sel de Na de la N2-(alcoylsuif)-N dodécyl-N-(N',N'-diéthylaminoéthyl)asparagine sont dissous dans 2 ml d'un mélange chloroforme/méthanol dans le rapport 2/1. On évapore le solvant à l'aide d'un évaporateur In a 50 ml round flask, 142 mg of the Na salt of N2- (alkylsuif) -N dodecyl-N- (N ', N'-diethylaminoethyl) asparagine are dissolved in 2 ml of a chloroform / methanol mixture in the report 2/1. The solvent is evaporated using an evaporator
45 rotatif, puis on élimine les dernières traces de solvant en soumettant le produit pendant 1 h à la pression réduite donnée par une pompe à palettes. 45 rotary, then the last traces of solvent are removed by subjecting the product for 1 h to the reduced pressure given by a vane pump.
On met en contact 10 ml d'une solution 0,3M de glucose avec le lipide. 10 ml of a 0.3M glucose solution are brought into contact with the lipid.
5o Le ballon, mis sur une secoueuse, est fortement agité durant 4 h. L'expérience est faite à la température ambiante. La taille des sphérules est d'environ 1 |i. La dispersion est alors filtrée sur colonne de gel Sephadex G 50 coarse gonflé dans une solution 0,145M de NaCl. 5o The balloon, placed on a shaker, is strongly agitated for 4 h. The experiment is carried out at room temperature. The size of the spherules is approximately 1 | i. The dispersion is then filtered on a column of Sephadex G 50 coarse gel swollen in a 0.145 M NaCl solution.
55 Exemple 6 55 Example 6
Dans un ballon de 50 ml, on dissout 80 mg du produit de formule générale: In a 50 ml flask, 80 mg of the product of general formula are dissolved:
R-/OCH2-CH VOH R- / OCH2-CH VOH
60 x CH2OH/n 60 x CH2OH / n
R étant le radical hexadécyle et n étant égal à 2,10 mg de cholestérol et 10 mg de dicétylphosphate dans 2 ml d'un mélange chloroforme/méthanol dans le rapport 2/1. R being the hexadecyl radical and n being equal to 2.10 mg of cholesterol and 10 mg of diketylphosphate in 2 ml of a chloroform / methanol mixture in the ratio 2/1.
On évapore le solvant à l'aide d'un évaporateur rotatif et on 65 élimine les dernières traces de solvant par passage à la pompe à palettes pendant 1 h. The solvent is evaporated using a rotary evaporator and the last traces of solvent are removed by passage through the vane pump for 1 h.
On met en contact 10 ml d'une solution 0,15M du sel de sodium de l'acide pyroglutamique avec les lipides. Le ballon, mis sur une 10 ml of a 0.15M solution of the sodium salt of pyroglutamic acid are brought into contact with the lipids. The ball, put on a
5 5
623 236 623,236
secoueuse, est agité fortement durant 2 h au bain-marie à 55° C, puis en refroidissant progressivement jusqu'à revenir à la température ambiante. shaker, is stirred vigorously for 2 h in a water bath at 55 ° C, then gradually cooling until it returns to room temperature.
La dispersion est soumise aux ultra-sons pendant 1 h à une température maintenue près de la température ambiante. On filtre 5 alors la dispersion sur une colonne de gel Sephadex G 50 coarse gonflé dans l'eau distillée. The dispersion is subjected to ultrasound for 1 h at a temperature maintained near room temperature. The dispersion is then filtered on a column of Sephadex G 50 coarse gel swollen in distilled water.
La dispersion obtenue est fluide et claire après passage aux ultra-sons; le diamètre des sphérules est inférieur à 1 |i. The dispersion obtained is fluid and clear after passing through the ultrasound; the diameter of the spherules is less than 1 | i.
Exemple 7 Example 7
Dans un ballon rond de 50 ml, on mélange intimement 200 mg du produit de formule générale: In a 50 ml round flask, 200 mg of the product of general formula are intimately mixed:
och2-ch v-oh och2-ch v-oh
I ) 15 I) 15
ch2oh/„ ch2oh / „
R étant le radical hexadécyle et n étant égal à 2,25 mg de cholestérol et 25 mg de dicétylphosphate; on met en contact le mélange obtenu avec 0,3 ml d'une solution d'aldéhyde tartrique à 10% et on homogénéise le mélange. L'expérience est faite à 55° C. On ajoute ensuite 4,7 ml d'une solution 0,145M de KCl. R being the hexadecyl radical and n being equal to 2.25 mg of cholesterol and 25 mg of diketylphosphate; the mixture obtained is brought into contact with 0.3 ml of a 10% tartaric aldehyde solution and the mixture is homogenized. The experiment is carried out at 55 ° C. Then 4.7 ml of a 0.145 M solution of KCl is added.
Le ballon, placé dans un bain-marie, est agité énergiquement à l'aide d'une secoueuse pendant 2 h à 55° C, puis en refroidissant progressivement jusqu'à revenir à la température ambiante. The flask, placed in a water bath, is stirred vigorously using a shaker for 2 h at 55 ° C, then gradually cooling until it returns to room temperature.
La dispersion obtenue est gélifiée et d'aspect légèrement bleuté. The dispersion obtained is gelled and slightly bluish in appearance.
L'application simultanée sur la peau de cette dispersion de niosomes et d'une solution aqueuse à même concentration finale en aldéhyde tartrique permet d'apprécier deux effets des niosomes lesquels, renforçant considérablement la coloration développée, améliorent nettement la tenue de cette coloration aux lavages à l'eau et aux détergents. The simultaneous application to the skin of this dispersion of niosomes and of an aqueous solution with the same final concentration of tartaric aldehyde makes it possible to appreciate two effects of the niosomes which, considerably reinforcing the developed coloration, clearly improve the resistance of this coloration to washing with water and detergents.
R R
Claims (19)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7520456A FR2315991A1 (en) | 1975-06-30 | 1975-06-30 | METHOD OF MANUFACTURING AQUEOUS DISPERSIONS OF LIPID SPHERULES AND CORRESPONDING NEW COMPOSITIONS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH623236A5 true CH623236A5 (en) | 1981-05-29 |
Family
ID=9157266
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH830776A CH616087A5 (en) | 1975-06-30 | 1976-06-29 | Dispersion of lipid spherules |
| CH42980A CH623236A5 (en) | 1975-06-30 | 1980-01-18 | Dispersion of lipid spherules |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH830776A CH616087A5 (en) | 1975-06-30 | 1976-06-29 | Dispersion of lipid spherules |
Country Status (14)
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|---|---|
| JP (2) | JPS588287B2 (en) |
| AT (1) | AT361893B (en) |
| AU (1) | AU505843B2 (en) |
| BE (1) | BE843300A (en) |
| BR (1) | BR7604270A (en) |
| CA (1) | CA1063908A (en) |
| CH (2) | CH616087A5 (en) |
| DE (3) | DE2660069C2 (en) |
| DK (1) | DK150967C (en) |
| ES (1) | ES449312A1 (en) |
| FR (1) | FR2315991A1 (en) |
| GB (1) | GB1539625A (en) |
| IT (1) | IT1062389B (en) |
| NL (1) | NL168715C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3713493A1 (en) * | 1986-04-22 | 1987-10-29 | Oreal | COSMETIC OR PHARMACEUTICAL AGENT BASED ON AN AQUEOUS DISPERSION OF LIPID BALLS |
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| US4217344A (en) * | 1976-06-23 | 1980-08-12 | L'oreal | Compositions containing aqueous dispersions of lipid spheres |
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| CH624011A5 (en) * | 1977-08-05 | 1981-07-15 | Battelle Memorial Institute | |
| BE871908R (en) * | 1977-11-15 | 1979-05-10 | Oreal | METHOD OF MANUFACTURING AQUEOUS DISPERSIONS OF LIPID SPHERULES AND CORRESPONDING NEW COMPOSITIONS |
| DK22879A (en) * | 1978-01-27 | 1979-07-28 | Sandoz Ag | PROCEDURE FOR MANUFACTURING A MEDICINE DELIVERY SYSTEM |
| GB2026340B (en) * | 1978-07-03 | 1982-12-22 | Ash P | Stabilising microvesicles |
| JPS5639033A (en) * | 1979-09-04 | 1981-04-14 | Kao Corp | Alpha-mono(methyl-branched alkyl glyceryl ether and skin cosmetic containing the same |
| JPS56120612A (en) * | 1980-02-27 | 1981-09-22 | Kanebo Keshohin Kk | Beautifying cosmetic |
| US5489426A (en) * | 1980-07-01 | 1996-02-06 | L'oreal | Cosmetic composition based on an aqueous dispersion of small lipid spheres |
| DE3161962D1 (en) * | 1980-07-01 | 1984-02-23 | Oreal | Process for obtaining stable dispersions in an aqueous phase of at least a water immiscible liquid phase, and corresponding dispersions |
| US5439672A (en) * | 1980-07-01 | 1995-08-08 | L'oreal | Cosmetic composition based on an aqueous dispersion of small lipid spheres |
| FR2492829A1 (en) * | 1980-10-24 | 1982-04-30 | Oreal | NON-IONIC SURFACE AGENTS DERIVED FROM GLUCOSE, PROCESS FOR THEIR PREPARATION AND COMPOSITIONS CONTAINING THE SAME |
| JPS57197236A (en) * | 1981-05-28 | 1982-12-03 | Kao Corp | 2-hydroxy-3-methyl branched alkoxypropyl glyceryl ether and cosmetic containing the same |
| FR2521565B1 (en) * | 1982-02-17 | 1985-07-05 | Dior Sa Parfums Christian | PULVERULENT MIXTURE OF LIPID COMPONENTS AND HYDROPHOBIC CONSTITUENTS, METHOD FOR PREPARING SAME, HYDRATED LIPID LAMELLAR PHASES AND MANUFACTURING METHOD, PHARMACEUTICAL OR COSMETIC COMPOSITIONS COMPRISING HYDRATED LAMID PHASES |
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| FR3046929B1 (en) | 2016-01-26 | 2018-03-02 | L'oreal | COSMETIC OR DERMATOLOGICAL COMPOSITION COMPRISING A MEROCYANINE AND AN OILY PHASE COMPRISING AT LEAST ONE DI OR TRICARBOXYLIC ACID ESTER |
| FR3068354B1 (en) | 2017-06-29 | 2020-07-31 | Oreal | PHOTOPROTECTOR COMPOSITIONS CONSISTING OF A DIBENZOYLMETHANE DERIVATIVE, A MEROCYANINE COMPOUND AND A COMPOUND LIKELY TO ACCEPT THE TRIPLET EXCITE LEVEL ENERGY OF THE DIBENZOYLMETHANE COMPOUND |
| FR3073409B1 (en) | 2017-11-15 | 2019-10-11 | L'oreal | COSMETIC OR DERMATOLOGICAL COMPOSITION COMPRISING A MEROCYANINE AND AN ACRYLIC POLYMER. |
| FR3073408B1 (en) | 2017-11-15 | 2019-10-11 | L'oreal | COMPOSITIONS COMPRISING AT LEAST ONE ACRYLIC POLYMER AND AT LEAST ONE INSOLUBLE ORGANIC FILTER |
| FR3083097B1 (en) | 2018-06-28 | 2020-11-27 | Oreal | COSMETIC OR DERMATOLOGICAL COMPOSITION COMPRISING A MEROCYANINE AND AN OILY PHASE CONTAINING AT LEAST ONE ALKYL OR ALKYLENE CARBONATE |
| EP3854377A1 (en) | 2020-01-22 | 2021-07-28 | Laboratoires Genevrier Sas | Composition comprising hyaluronic acid and a polyol or carboxymethylcellulose |
| US20230415074A1 (en) * | 2020-04-14 | 2023-12-28 | Dow Global Technologies Llc | Foam control agent |
| FR3117824A1 (en) | 2020-12-18 | 2022-06-24 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine and an oily phase comprising at least one citric acid ester |
| FR3117825A1 (en) | 2020-12-18 | 2022-06-24 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine, a triazine UV filter, and a polysaccharide modified by hydrophobic chains |
| FR3119988B1 (en) | 2021-02-25 | 2023-12-29 | Oreal | Aqueous composition comprising an organic UV filter, a superabsorbent polymer, perlite and a fatty alcohol |
| FR3124698A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one UV screening agent, boron nitride, and a nonionic surfactant of ester type |
| FR3128118A1 (en) | 2021-10-14 | 2023-04-21 | L'oreal | Hair treatment method comprising the application of an oil-in-water emulsion comprising an aqueous phase, a fatty phase and a polymer |
| FR3141059A1 (en) | 2022-10-20 | 2024-04-26 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine and a gamma-butyrolactone and/or a gamma-butyrolactam |
| FR3130599A1 (en) | 2021-12-17 | 2023-06-23 | L'oreal | Cosmetic or dermatological composition comprising a merocyanin and a gamma-butyrolactone and/or a gamma-butyrolactam |
| WO2023110767A1 (en) | 2021-12-17 | 2023-06-22 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine and a gamma-butyrolactone and/or a gamma-butyrolactam |
| FR3130598A1 (en) | 2021-12-17 | 2023-06-23 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine and di-t-butyl pentaerythrityl tetra hydroxycinnamate |
| FR3130594A1 (en) | 2021-12-17 | 2023-06-23 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine and resveratrol and/or a resveratrol derivative |
| FR3130593A1 (en) | 2021-12-17 | 2023-06-23 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine and dipropylene glycol |
| FR3130597A1 (en) | 2021-12-17 | 2023-06-23 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine and at least one diol comprising from 4 to 7 carbon atoms |
| FR3132637A1 (en) | 2022-02-15 | 2023-08-18 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine and a polyionic complex |
| FR3141061A1 (en) | 2022-10-21 | 2024-04-26 | L'oreal | Composition comprising a lipophilic organic filter, a hydrophilic organic filter, spherical particles of porous silica, spherical particles of cellulose, and an N-acylated amino acid powder |
| FR3141060A1 (en) | 2022-10-21 | 2024-04-26 | L'oreal | Composition comprising a lipophilic organic UV filter, a hydrophilic organic UV filter and a specific hydrophilic gelling polymer |
| FR3141062A1 (en) | 2022-10-21 | 2024-04-26 | L'oreal | Composition comprising a lipophilic organic filter, a hydrophilic organic filter, with a quantity by weight of fatty phase between 20 and 70% and a mass ratio of hydrophilic organic filters/lipophilic organic filters greater than 0.3 |
| WO2024083567A1 (en) | 2022-10-21 | 2024-04-25 | L'oreal | Composition comprising a lipophilic organic screening agent, a hydrophilic organic screening agent, with an amount by weight of fatty phase between 20 and 70% |
| FR3142897A1 (en) | 2022-12-09 | 2024-06-14 | L'oreal | Composition comprising a water-dispersible organic filter and at least one polyionic complex containing a cationic polysaccharide and a non-polymeric acid having at least 3 pKa values and/or one of its salts |
| FR3143344A1 (en) | 2022-12-16 | 2024-06-21 | L'oreal | Composition comprising a UV filter, a suitably selected lipophilic polymer, and a carrageenan |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2249552A1 (en) * | 1971-10-12 | 1973-05-30 | Inchema S A | PROCESS FOR THE INCAPSULATION OF IN PARTICULAR WATER-SOLUBLE COMPOUNDS |
-
1975
- 1975-06-30 FR FR7520456A patent/FR2315991A1/en active Granted
-
1976
- 1976-06-23 BE BE168219A patent/BE843300A/en not_active IP Right Cessation
- 1976-06-28 AT AT470376A patent/AT361893B/en not_active IP Right Cessation
- 1976-06-28 ES ES449312A patent/ES449312A1/en not_active Expired
- 1976-06-29 DE DE2660069A patent/DE2660069C2/de not_active Expired - Lifetime
- 1976-06-29 AU AU15393/76A patent/AU505843B2/en not_active Expired
- 1976-06-29 DK DK291376A patent/DK150967C/en not_active IP Right Cessation
- 1976-06-29 CH CH830776A patent/CH616087A5/en not_active IP Right Cessation
- 1976-06-29 DE DE2629100A patent/DE2629100C3/en not_active Expired
- 1976-06-29 GB GB27094/76A patent/GB1539625A/en not_active Expired
- 1976-06-29 DE DE2661108A patent/DE2661108C2/en not_active Expired - Lifetime
- 1976-06-29 CA CA255,929A patent/CA1063908A/en not_active Expired
- 1976-06-30 IT IT68608/76A patent/IT1062389B/en active
- 1976-06-30 JP JP51076601A patent/JPS588287B2/en not_active Expired
- 1976-06-30 NL NLAANVRAGE7607210,A patent/NL168715C/en not_active IP Right Cessation
- 1976-06-30 BR BR7604270A patent/BR7604270A/en unknown
-
1980
- 1980-01-18 CH CH42980A patent/CH623236A5/en not_active IP Right Cessation
-
1981
- 1981-01-07 JP JP51981A patent/JPS56108528A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3713493A1 (en) * | 1986-04-22 | 1987-10-29 | Oreal | COSMETIC OR PHARMACEUTICAL AGENT BASED ON AN AQUEOUS DISPERSION OF LIPID BALLS |
Also Published As
| Publication number | Publication date |
|---|---|
| ES449312A1 (en) | 1977-08-16 |
| FR2315991A1 (en) | 1977-01-28 |
| DK291376A (en) | 1976-12-31 |
| DE2629100B2 (en) | 1979-11-29 |
| DK150967B (en) | 1987-10-05 |
| FR2315991B1 (en) | 1977-12-02 |
| JPS6156016B2 (en) | 1986-12-01 |
| CA1063908A (en) | 1979-10-09 |
| DE2629100A1 (en) | 1977-01-20 |
| BE843300A (en) | 1976-12-23 |
| NL168715C (en) | 1982-05-17 |
| GB1539625A (en) | 1979-01-31 |
| DE2629100C3 (en) | 1980-08-14 |
| AU1539376A (en) | 1978-01-05 |
| IT1062389B (en) | 1984-10-10 |
| JPS588287B2 (en) | 1983-02-15 |
| DE2661108C2 (en) | 1993-12-16 |
| JPS56108528A (en) | 1981-08-28 |
| NL7607210A (en) | 1977-01-03 |
| ATA470376A (en) | 1980-09-15 |
| DK150967C (en) | 1988-02-15 |
| AU505843B2 (en) | 1979-12-06 |
| AT361893B (en) | 1981-04-10 |
| CH616087A5 (en) | 1980-03-14 |
| JPS526375A (en) | 1977-01-18 |
| DE2660069C2 (en) | 1990-09-13 |
| BR7604270A (en) | 1977-04-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |