CA1063908A - Process for the production of dispersions of lipidic droplets in water and new compositions based on same - Google Patents
Process for the production of dispersions of lipidic droplets in water and new compositions based on sameInfo
- Publication number
- CA1063908A CA1063908A CA255,929A CA255929A CA1063908A CA 1063908 A CA1063908 A CA 1063908A CA 255929 A CA255929 A CA 255929A CA 1063908 A CA1063908 A CA 1063908A
- Authority
- CA
- Canada
- Prior art keywords
- phase
- dispersion
- fact
- spherules
- encapsulated
- 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.)
- Expired
Links
- 239000006185 dispersion Substances 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 230000008569 process Effects 0.000 title claims abstract description 14
- 239000000203 mixture Substances 0.000 title abstract description 28
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000002632 lipids Chemical class 0.000 claims abstract description 57
- 239000012071 phase Substances 0.000 claims abstract description 49
- 239000008346 aqueous phase Substances 0.000 claims abstract description 34
- -1 lipid compounds Chemical class 0.000 claims abstract description 24
- 239000013543 active substance Substances 0.000 claims abstract description 10
- 239000002537 cosmetic Substances 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 235000013305 food Nutrition 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 35
- 150000002500 ions Chemical class 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 7
- 238000002604 ultrasonography Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- 229920005862 polyol Polymers 0.000 claims description 6
- 150000003077 polyols Chemical class 0.000 claims description 6
- 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 5
- 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 5
- 229930186217 Glycolipid Natural products 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000002191 fatty alcohols Chemical class 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000000600 sorbitol Substances 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 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 claims description 4
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 4
- 229920000223 polyglycerol Polymers 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000004166 Lanolin Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 125000003010 ionic group Chemical group 0.000 claims description 3
- 229940039717 lanolin Drugs 0.000 claims description 3
- 235000019388 lanolin Nutrition 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 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
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 229940124091 Keratolytic Drugs 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 230000001166 anti-perspirative effect Effects 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 239000003213 antiperspirant Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 235000012000 cholesterol Nutrition 0.000 claims description 2
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 229940120503 dihydroxyacetone Drugs 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 239000003349 gelling agent Substances 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- 239000003906 humectant Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 230000001530 keratinolytic effect Effects 0.000 claims description 2
- 239000003410 keratolytic agent Substances 0.000 claims description 2
- 229940099367 lanolin alcohols Drugs 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
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 230000001256 tonic effect Effects 0.000 claims description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- 229930182558 Sterol Natural products 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 150000008051 alkyl sulfates Chemical class 0.000 claims 2
- 229930183167 cerebroside Natural products 0.000 claims 2
- 150000001784 cerebrosides Chemical class 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- 150000003432 sterols Chemical class 0.000 claims 2
- 235000003702 sterols Nutrition 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000001840 Dandruff Diseases 0.000 claims 1
- 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 1
- 210000004381 amniotic fluid Anatomy 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 239000003212 astringent agent Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003899 bactericide agent Substances 0.000 claims 1
- 230000002951 depilatory effect Effects 0.000 claims 1
- 229940088598 enzyme Drugs 0.000 claims 1
- UQPHVQVXLPRNCX-UHFFFAOYSA-N erythrulose Chemical compound OCC(O)C(=O)CO UQPHVQVXLPRNCX-UHFFFAOYSA-N 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 235000019634 flavors Nutrition 0.000 claims 1
- 150000004676 glycans Chemical class 0.000 claims 1
- 230000035876 healing Effects 0.000 claims 1
- 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 1
- 229960000367 inositol Drugs 0.000 claims 1
- 239000002608 ionic liquid Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000002304 perfume Substances 0.000 claims 1
- 229920001184 polypeptide Polymers 0.000 claims 1
- 229920001282 polysaccharide Polymers 0.000 claims 1
- 239000005017 polysaccharide Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 claims 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical group [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 claims 1
- 239000000516 sunscreening agent Substances 0.000 claims 1
- 229960005486 vaccine Drugs 0.000 claims 1
- 229940088594 vitamin Drugs 0.000 claims 1
- 239000011782 vitamin Substances 0.000 claims 1
- 229930003231 vitamin Natural products 0.000 claims 1
- 235000013343 vitamin Nutrition 0.000 claims 1
- 239000003643 water by type Substances 0.000 claims 1
- 238000005538 encapsulation Methods 0.000 abstract description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
- 239000011780 sodium chloride Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 6
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 5
- 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 5
- 229920005654 Sephadex Polymers 0.000 description 5
- 239000012507 Sephadex™ Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000002502 liposome Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 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
- 230000007794 irritation Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000002353 niosome Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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 2
- 230000008961 swelling Effects 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- PVPBBTJXIKFICP-UHFFFAOYSA-N (7-aminophenothiazin-3-ylidene)azanium;chloride Chemical compound [Cl-].C1=CC(=[NH2+])C=C2SC3=CC(N)=CC=C3N=C21 PVPBBTJXIKFICP-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000532370 Atla Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000655872 Puia Species 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
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 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
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
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- 238000005461 lubrication Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification 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
- 230000008520 organization Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 206010037833 rales Diseases 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010583 slow cooling Methods 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
- 239000010409 thin film Substances 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000006200 vaporizer Substances 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
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Abstract
La présente invention a pour objet un procédé d'obtention d'une dispersion de sphérules constituées de couches moléculaires organisées renfermant une phase aqueuse à encapsuler, caractérisé par le fait que l'on met en contact, d'une part, au moins un lipide liquide dispersible dans l'eau et ayant pour formule générale: X - Y formule dans laquelle X représente un groupe hydrophile ionique ou non-ionique et Y représente un groupe lipophile, et d'autre part la phase aqueuse à encapsuler dans les sphérules, le rapport lipophile/hydrophile du lipide étant tel que ce dernier gonfle dans la phase aqueuse à encapsuler, pour former une phase lamellaire; que l'on agite pour assurer le mélange et obtenir une phase lamellaire; que l'on ajoute ensuite un liquide de dispersion en quantité supérieure à la quantité de phase lamellaire obtenue et que l'on secoue énergiquement pendant un temps variant de 15mn à 4 heures environ, 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, étant compris entre 0.1 environ et 3 environ, et le rapport pondéral de la quantité de phase de dispersion, que l'on ajoute, à la quantité de phase lamellaire, que l'on disperse, étant compris entre 2 et 100 environ. L'invention a aussi pour objet des dispersions de sphérules résultant de ce procédé, qui sont constituées de composés lipidiques non-ioniques et qui, de ce fait, forment des compositions nouvelles permettant un encapsulage de substances actives, utilisables par exemple en pharmacie, en alimentation ou en cosmétique.The subject of the present invention is a process for obtaining a dispersion of spherules consisting of organized molecular layers containing an aqueous phase to be encapsulated, characterized in that at least one lipid is brought into contact liquid dispersible in water and having the general formula: X - Y formula in which X represents an ionic or nonionic hydrophilic group and Y represents a lipophilic group, and on the other hand the aqueous phase to be encapsulated in the spherules, the lipophilic / hydrophilic ratio of the lipid being such that the latter swells in the aqueous phase to be encapsulated, to form a lamellar phase; that is stirred to ensure mixing and to obtain a lamellar phase; that a dispersion liquid is then added in an amount greater than the amount of lamellar phase obtained and that it is vigorously shaken for a time varying from 15 minutes to approximately 4 hours, the weight ratio between the amount of aqueous phase to be encapsulated put in contact with the lipids and the quantity of lipids forming the lamellar phase, being between approximately 0.1 and approximately 3, and the weight ratio of the quantity of dispersion phase, which is added to the quantity of lamellar phase, that it is dispersed, being between 2 and 100 approximately. The subject of the invention is also dispersions of spherules resulting from this process, which consist of nonionic lipid compounds and which, therefore, form novel compositions allowing encapsulation of active substances, usable for example in pharmacy, in food or cosmetics.
Description
~ a pr~sente invention a pour ob~et un procéd~ d'obten-tion d~une disperslon aqueuse de sph~rules de diametre in~érleur ou supérieur ~ 1,000 ~ a dee concentrations élev~e~, le~dites sph~rules pouvant encapouler des sub~tances actlve~ ~Yec un fort rendement d~encspsulation. ~'invention a aussi pour objet une ais-perYion de sph~rule~ conatitu~e~ de couche~ mol~¢ulaire~ organi~ées de ¢omposés lipidiques non-ioniques ~ n salt que oertains lipldes po~sadent 18 propri~té de former, en pré~ence d~eau? des phases m~somorphe~ dont l'~tst d'organisation est intermédiaire entre l'~tat cristallin et ~ l'état liquide. Parmi le~ lipides qui donnent nais~ance à de~
: pha~e~ mésomorphes, il a dé~ ét~ indiqué que certains peuvent gonfler en solution aqueu~e pour former des ~phérules disper~ées dans le milieu aqueux, ce~ sphérules étant constitu~es par de~
couches multl~ moléculsiree et de préférence par de~
oouohes bimol~culaire~ aysnt une ~pai~ur approximative de 30 à
100 ~ (volr, en particulier, ltarticle de Bangham~ Standish et Watkins, J. Mol. ~iol.~ 13, 238 ~1965).
Jusqu'~ présent, il n's été pos~ible d'obtenir de~
sph~rules lipidiques constituées de feuillets con¢entrique~ qu'en utilisant des lipides comportant un groupe hydrophile ionique et un groupe lipophile et les procédéa de préparstion, qui ont été
d~crits, entrainant l'obtention de sphérules ayant un diam~tre moyen inf~rleur ~ 1,000 ~ . Ie procédé d'obtention de ces ~ph~rules consi~te ~ r~aliser une dispersion, dont la phase di~per3~e contient la substance lipidique susceptible de former les sph~rules, et à soumettre cette disper~ion ~ un traitement par ultra-~on~; pour r~ali~er la dispersion que l'on ~oumet aus ultra-aons~ on peut, en premier lieu, r~ali~er ~ur une paroi, par 3~ ~aporation, un film mince de la sub~tance lipidique ~ di~perser, pUi8 en second lieu, mettre en contact avec la paroi ain~i re~êtue, la phase continue de la di~persion ~ r~ali~er et enfin~ en troi~ième lieu, agiter pour obte~ir la dispersion a soumettre aux ultra-~on~. Dans un autre proc~d~ décrit dans la demande de brevet français 2,221,122, on peut ~galement, pour obtenir la di~persion ~ soumettre aux ultrs-sons, a~outer le lipide destiné
à form~r le~ paroi~ de ~ph~rules à une pha~e squeuse, pUi9 chauffer légarement et agiter énergiquement par ~ecousses. Les sphérule~
constitu~e~ de feuillets concentriques que l'on obtient ainei et qui ont un dlsmatre maximNm de 1,000 g environ, sont en gén~ral appelées des lipo~ome~.
On 8 dé~a propoeé d'utiliser les liposomea pour enfermer de~ ~oluté~ aqueux comportant des sub~tances active~ dan~ les compartimente aqueux compris entre le 8 double 8 couches lipidiquea et pour protéger ainsi les ~ub~tances encap~ulées contre le~
conditions ext~rieure~ (voir, en particulier, l'article Sessa et ~elsmann, J. Lipid Res , 9, 310 (1968) et l'article ~agee et ~iller? Nature, Vol 2~5 (1972). Les lipoeomee pouvant avoir de~
tsille~ variables dans la gsmme inférieure ~ 1,000 A , on peut faire varier leur pouvoir de p~nétration dan~ le oo~pe humain~
oe qui a permi~ d'envieager de nombreu~e~ utili~ation~ eur le pla~
pharmsoeutique, d'autant plue que leur oharge électrique extérieure peut permettre de choisir leur ~ite de fixation (Biochem J. (1971), 124 p. 58 P~. Cependant, sur le plan co$métique, l'utilisation de sphérules de diamètre inférieur ~ 1,000 ~ e~t su~ceptible d'engendrer quelques inconvénients en raison du risque de pénétra-tion des produits ~ travers 1~ peau. Il est donc clair, qu'au moin~ pour ce type d'application, il ~erait souhaitable de pouvoir réali~er des ~phérule~ ~ feuillets lipidiques concentriquea ayant un diamètre supérieur à 1,000 ~.
De plu~, les procédé~ actuellement connua pour l'obten-tion ~es liposomes renfermant de~ sub~tsnce~ actives entre leur~
feuillets lipidiquee concentriques, ont des inconv~nient~ considé-rables : en p~emier lieu, la ~ubstsnce active plac~e dans la 1063gO8 phase continue de la dispersion que l'on soumet aux ultr~-~ons, n'e~t encapsulée entre les feuillet~ lipldique~ des l$posome~ que pour une tre~ faible partie, car une trè~ faible partie de la phase continue de la disper~ion ~e trouve emprisonnée entre lesdits feuillets. ~orsque l'on dé~ire isoler les liposomes d'encapsula-tion, il e~t n~ca~saire de faire passer la disperaion, que l'on ~ aoumi~e au~ ultra-sons, ~ur une colonne de ~ép~ration du type Sephadex , ~uquel oa~ les lipo~ome~ ~e retrouvent sou~ forme d'une disper~ion e~trêmement diluée. Il en résulte que, d'une part, il n'est pratiquement pa~ possible, avec le~ procéd~s oonnu~, d'obtenir une forte concentration de liposomes et que, d'autre part, la substance active n'est encsp~ulée ~ue dan~ une faible proportion et se trouve perdue dans l'élution de la colonne de séparation s~ns qu'il ~oit partiquement pO9 sible de la r~cupérer de fsçon ~imple, ce qui entraine une augment~tion importante du priY de revient de~ ~ubstance~ aotives encapsulées dans le~ lipo-aomes. Il e~t donc ~ouhaitable de disposer d'un proc~dé de fabri-¢ation de sphérule~ ~ feuillet~ ¢oncentrique~ qui permette llob-tention d'une di~per~lon ~ forte ooncentration de sph~rules avec une perte réduite du produit enoapsulé entre les feuillets des ~ph~rule 8.
Enfin, le~ procédé~ de fabrication de liposome~ qui ont ét~ décrit~ ju~qu'à ce jour, msntionnent que l'on ne peut utiliser ~ue certaine~ catégories bien détermin~e~ de lipide~ : dans l'état de la technique précédemm~nt citée, on a mentlonn~ l'utilisation de phospholipide~, de lipidss comportant un groupe hydrophile ionlque et un groupe lipophile, et d'acides gr~s insaturés.
Ia pr~sente invention a pour but de décrire un proc~dé
d'obtent~on d'une dispersion aqueuse de sph~rules de diamètre inf~ri~ur ou ~upérieur ~ 1,000 A ~ des concentr~tions ~levées, les-dite~ sph~rule~ pouv~nt enc~psuler des substances actives avec un fort rendement d'encspsulation. Au sens de la pr~sente descrip-* marque de c~mmerce designant le gel disposé à l'intérieur d'une colonne dans laquelle est filtree la dispersion de sphéruleS
tion, 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. Le procédé selon l'invention peut s'appliquer à des lipides ioniques ou non-ioniques et permet donc d'inclure, parmi les lipides susceptibles de constituer des sphérules, des composés lipidiques non-ioniques.
La présente invention a donc pour objet un nouveau procédé d'obtention d'une dispersion de sphérules constituées de couches moléculaires organisées enfermant une phase aqueuse à
encapsuler, caractérisé par le fait que l'on met en contact, d'une part, au moins un lipide liquide dispersible dans l'eau et ayant pour formule générale:
X Y
formule dans laquelle X représente un groupe hydrophile ionique ou non-ionique et Y représente un groupe lipophile, et d'autre part la phase aqueuse à encapsuler dans les sphérules, le rapport lipophile/hydrophile du lipide étant tel que ce dernier gonfle dans la phase aqueuse a encapsuler, pour former une phase lamellaire;
que l'on agite pour assurer le mélange et obtenir une phase lamel-laire; que l'on ajoute ensuite un liquide de dispersion en quantité
supérieure à la quantité de phase lamellaire obtenue et que l'on secoue énergiquement pendant un temps variant de 15 mn à 4 heures environ, le rapport pondéral entre la quantité de phase aqueuse a encapsuler mise en contact avec les lipides et la quantité de lipides formant la phase lamellaire étant compris entre 0.1 et 3 environ, et le rapport pondéral de la quantité de phase de dispersion, que l'on ajoute, a la quantité de phase lamellaire, que l'on disperse, étant compris entre 2 et 100 environ.
~: La phase aqueuse a encapsuler peut être de l'eau ou une solution aqueuse de produit actif. La phase de dispersion et la phase aqueuse a encapsuler sont, de préférence isoosmotiques;
la phase de dispersion peut avantageusement ~' t 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 oeuvre à température ambiante ou à une tempé- -rature plus élevée si le lipide est solide à température ambiante;
dans le cas où l'on désire que les sphérules obtenues aient un dia-; mètre moyen inférieur à 1,000 A, on peut soumettre la dispersion de sphérules à un traitement aux ultra-sons.
Pour former la phase lamellaire, on peut utiliser un seul lipide ou un mélange de lipides. Le (ou les) lipides(s), que l'on utilise, comporte(nt) une cha~ne lipophile longue comportant de 12 à 30 atomes de carbone, saturée ou insaturée, ramifiée ou linéaire;
on peut, en particulier, choisir des cha~nes oléique, lanolique, tétradécylique, hexadécylique, isostéarylique, laurique ou alcoyl-phényl. Lorsque le groupement hydrophile du lipide formant la phase lamellaire est un groupement non-ionique, on peut avantageusement choisir, comme groupement hydrophile, un polyoxyéthylène, un poly-glycérol, un ester de polyol oxyéthyléné ou non, et, par exemple, un ester de sorbitol polyoxyéthyléné. Lorsque le groupement hydrophile du lipide formant la phase lamellaire est un groupement ionique, on peu~ avantageusement choisir, comme groupement hydrophile, un com-posé amphotère comportant deux chaines lipophiles ou une association de deux ions organiques à longue chalne de signes opposés. On a obtenu des résultats très satisfaisants en utilisant comme lipides formant la phase lamellaire des éthers de polyglycérol, tels que ceux qui sont décrits dans les brevets français n 1,477,048 et ~ a pr ~ present invention has ob ~ and a procedure ~ of obtaining tion of an aqueous disperslon of sph ~ rules of diameter in ~ erector or higher ~ 1,000 ~ at high concentrations, say sph ~ rules that can encapoulate substances actlve ~ ~ Yec un fort encspsulation efficiency. ~ The invention also relates to an ais-perYion of sph ~ rule ~ conatitu ~ e ~ of layer ~ mol ~ ¢ ulaire ~ organi ~ ed of nonionic lipid components ~ n salt that some lipldes po ~ sadent 18 property ~ t to train, in the presence of water? m ~ somorphous ~ phases including ~ tst of organization is intermediate between the crystalline state and ~ liquid state. Among the ~ lipids that give birth ~ ance to ~
: pha ~ e ~ mesomorphic, it has been ~ indicated ~ that some may swell in aqueous solution to form ~ dispersed pherules in the aqueous medium, this ~ spherules being constituted ~ es by of ~
multl ~ molecular layers and preferably by ~
oouohes bimol ~ ring ~ has an approximate ~ 30 ~ ur 100 ~ (volr, in particular, the article by Bangham ~ Standish and Watkins, J. Mol. ~ iol. ~ 13, 238 ~ 1965).
Up to now, it has not been possible to obtain from ~
sph ~ lipid rules made up of concentric sheets ~ that using lipids having an ionic hydrophilic group and a lipophilic group and the preparation processes, which have been described, resulting in the production of spherules having a diameter medium inf ~ rleur ~ 1,000 ~. The process for obtaining these ~ ph ~ rules consi ~ te ~ r ~ achieve a dispersion, whose phase di ~ per3 ~ e contains the lipid substance capable of forming the sph ~ rules, and to submit this disper ~ ion ~ treatment by ultra- ~ on ~; to achieve the dispersion that we are leaving ultra-aons ~ we can, first, r ~ ali ~ er ~ ur a wall, by 3 ~ ~ incorporation, a thin film of the lipid sub ~ tance ~ di ~ perser, pUi8 second, put in contact with the wall ain ~ i re ~ éttue, the continuous phase of the di ~ persion ~ r ~ ali ~ er and finally ~ en third place, shake to obtain the dispersion to be submitted to ultra- ~ on ~. In another proc ~ d ~ described in the request for French patent 2,221,122, we can also ~, to obtain the di ~ persion ~ submit to ultrasound, a ~ outer lipid intended to form ~ r the ~ wall ~ of ~ ph ~ rules to a pha ~ e squeuse, pUi9 heat lightly and shake vigorously by ~ foam. The spherule ~
made up of concentric sheets which are obtained ainei and which have a maximum diameter of about 1,000 g, are generally called lipo ~ ome ~.
We 8 die ~ proposed to use the liposomea to enclose of ~ ~ olute ~ aqueous containing sub ~ tances active ~ dan ~
aqueous compartment between the 8 double 8 lipid layersa and to thus protect the ~ ub ~ encaps tances ~ ulées against the ~
external conditions (see, in particular, the article Sessa and ~ elsmann, J. Lipid Res, 9, 310 (1968) and the article ~ agee et ~ iller? Nature, Vol 2 ~ 5 (1972). Lipoeomee can have ~
tsille ~ variables in the lower range ~ 1,000 A, we can vary their power of penetration into the human oo pe oe which allowed ~ envieager many ~ e ~ utili ~ ation ~ eur le pla ~
pharmsoeutique, all the more as their external electric charge can allow to choose their fixation ite (Biochem J. (1971), 124 p. 58 P ~. However, in terms of cost, the use of spherules of smaller diameter ~ 1,000 ~ e ~ t su ~ ceptible cause some inconvenience due to the risk of tion of products ~ through 1 ~ skin. It is therefore clear that less ~ for this type of application, it would be desirable to be able realize ~ pherule ~ ~ concentric lipid sheets having a diameter greater than 1,000 ~.
More ~, the processes currently known for obtaining tion ~ es liposomes containing ~ sub ~ tsnce ~ active between their ~
concentric lipid sheets, have disadvantages ~ consider-rables: in the first place, the active ubstsnce placed in the 1063gO8 continuous phase of the dispersion which is subjected to ultr ~ - ~ ons, is not encapsulated between the sheets ~ lipldique ~ of the $ posome ~ that for a very low part, because a very low part of the phase continues to disper ~ ion ~ e found trapped between said leaflets. ~ when we want to isolate the liposomes from encapsula-tion, it is ~ tn ~ ca ~ saire to pass the disperaion, that one ~ aoumi ~ e au ~ ultrasounds, ~ ur a column of ~ ép ~ ration of the type Sephadex, ~ uquel oa ~ lipo ~ ome ~ ~ e find sou ~ form of a disper ~ ion e ~ very diluted. It follows that, from a apart, it is practically not possible with the procedure known ~, to obtain a high concentration of liposomes and that, on the other hand, the active substance is encsp ~ ulée ~ ue dan ~ a low proportion and is lost in the elution of the column of separation s ~ ns that it ~ oit partially pO9 sible to recover it ~
of fsçon ~ imple, which leads to a significant increase ~ tion of priY returns from ~ ~ ubstance ~ aotives encapsulated in ~ lipo-atoms. It is therefore ~ ouhaitable to have a process of manufacturing ¢ spherule ation ~ ~ sheet ~ ¢ oncentric ~ which allows llob-retention of a di ~ per ~ lon ~ strong ooncentration of sph ~ rules with a reduced loss of the product encapsulated between the sheets of the ~ ph ~ rule 8.
Finally, the ~ process ~ for manufacturing liposomes ~ which have ét ~ described ~ ju ~ that to date, msntionnent that one cannot use ~ a certain ~ definite categories ~ e ~ of lipid ~: in the state of the previously mentioned technique, we have mentlonn the use of phospholipid ~, of lipids containing a hydrophilic group ionlque and a lipophilic group, and unsaturated fatty acids.
The purpose of the present invention is to describe a process get ~ an aqueous dispersion of sph ~ rules of diameter inf ~ ri ~ ur or ~ higher ~ 1,000 A ~ concentrations ~ tions ~ lifted, said ~ sph ~ rule ~ can ~ nt enc ~ psulate active substances with a high encsulation efficiency. Within the meaning of this description * trade mark designating the gel placed inside a column in which the dispersion of spherules is filtered tion, the word "encapsulate" is used to indicate that one has an aqueous phase inside a capsule made up - by lipid spherules. The method according to the invention can apply to ionic or non-ionic lipids and allows therefore to include, among the lipids liable to constitute spherules, non-ionic lipid compounds.
The present invention therefore relates to a new process for obtaining a dispersion of formed spherules of organized molecular layers enclosing an aqueous phase to encapsulate, characterized by the fact that, in contact, hand, at least one liquid lipid dispersible in water and having for general formula:
XY
formula in which X represents an ionic hydrophilic group or nonionic and Y represents a lipophilic group, and other the aqueous phase to be encapsulated in the spherules, the ratio lipophilic / hydrophilic of the lipid being such that the latter swells in the aqueous phase to be encapsulated, to form a lamellar phase;
shake to ensure mixing and obtain a lamel phase laire; that we then add a dispersion liquid in quantity greater than the quantity of lamellar phase obtained and which shakes vigorously for a time varying from 15 min to 4 hours approximately, the weight ratio between the quantity of aqueous phase to encapsulate contact with lipids and the amount of lipids forming the lamellar phase being between 0.1 and 3 approximately, and the weight ratio of the amount of phase of dispersion, which is added, to the quantity of lamellar phase, which is dispersed, being between 2 and 100 approximately.
~: The aqueous phase to be encapsulated can be water or a aqueous solution of active product. The dispersion phase and the aqueous phase to be encapsulated are, preferably isoosmotic;
the dispersion phase can advantageously ~ ' t be an aqueous solution; the agitation carried out as last phase of the process is obtained by means of a shaker;
the process is carried out at room temperature or at a temperature -higher rature if the lipid is solid at room temperature;
in the case where it is desired that the spherules obtained have a diameter ; average meter less than 1,000 A, the dispersion of spherules in an ultrasound treatment.
To form the lamellar phase, one can use a single lipid or a mixture of lipids. The lipid (s), which one uses, comprises (nt) a long lipophilic chain comprising of 12 with 30 carbon atoms, saturated or unsaturated, branched or linear;
we can, in particular, choose chains ~ oleic, lanolic, tetradecylic, hexadecylic, isostearyl, lauric or alkyl-phenyl. When the hydrophilic grouping of the lipid forming the phase lamellar is a nonionic group, it is advantageously possible choose, as hydrophilic group, a polyoxyethylene, a poly-glycerol, an ester of polyol oxyethylenated or not, and, for example, a polyoxyethylenated sorbitol ester. When the hydrophilic group of the lipid forming the lamellar phase is an ionic group, we little ~ advantageously choose, as hydrophilic group, a com-amphoteric pose comprising two lipophilic chains or a combination of two long-chain organic ions of opposite signs. We have obtained very satisfactory results using as lipids forming the lamellar phase of polyglycerol ethers, such as those described in French patents n 1,477,048 and
2,091,516 et dans le certificat d'addition 94,928.
On peut utiliser une phase aqueuse à encapsuler compor-tant des substances actives de toutes sortes et, en particulier, des substances ayant un intérêt pharmaceutique, ou alimentaire, ou des substances ayant une activité cosmétique. Les substances acti-ves peuvent ~tre par exemple, en ce qui concerne la substance cosmétique; les produits destinés aux soins de la peau et du cheveu, par e~emple des humectants, tels que la glycérine, le ~orbitol, le pentsérythritol, l'ino~itol, l'acide pyrrolidone-carbo~ylique et ses sels; des agents de bruni~sage artificiel tel3 que 18 dihydroxyacétone, l'érythrulo~e, la glycéraldéhyde, le~
~-dialdéhydes tels que l'aldéhyde tartrique (ce~ prQduits pouvant ~tre éventuellement associés ~ dee colorant~)t de~ agents anti~olai-re~ hydro~oluble~; de~ antiperspirants, de~ déodorants, des a3trin-gents~ des produit~ r~frai¢hlcoant~ toniques, ci¢atrisants, kératolytiques, dépila~oire~5 des eaus parfumées~ de~ extraits de tissu~ animaux ou végétaux; tel~ que prot~ine~, polgsaccharide~, liquide amniotique; des colorants hydrosolublesf de~ agents snti-pelli¢ulaires, des agent~ antiséborrhéiques, des oxydants (agents de décoloration) comme l'eau osygén~e, de~ reducteurs tels que l'acide thioglycolique et ae~ sel~. Comme ~ubstance~ sctives pharmaceutiques on peut citer : lee vita~ines, le~ hormones, les enzymes, (par eYemple, le superoxyde dismuta~e), le~ vac¢ins, les antl-inflammatoires (hydrocortisone, par exemple), les antibioti-que~, les bsct~rioide~, Il e~t olair que l'on ohoi~ira, en fonotion de la subs-tance aotive contenue dan3 la phase aqueuse ~ encapauler, des lipide~ susceptible~ d'encap~uler de façon stable la phase aqueu~e consid~ré. Pour que les lipide~ constituant la pha~e lamellaire donnent des sphérule~ stables, il e~t néce~saire ~util y ait une interaction lst~rale suffisante entre les chaines de lipides qui, placées c8te ~ cote, constituent lee couches ou feuillets des sphérules, c'eot-~-dire que le~ forces de Van der Waals entre les chaine~ as~urent une cohesion suffisante des feuillets. Cette con-dition est satisfaite pour le~ lipides ayant les caractéristiques indiquée~ dan~ la définition gén~rale du procéd~ c~-dessus donné.
~es lipides pouvant 8tre utilis~ dans le procéd~ ~elon l'inven-tion appartiennent ~ la cla~se des ~mulsionnants du type eau dan~
l'huile.
~ - `
Le procédé ~elon l'invention permet d'obtenir des dis-persion~ de aphérules qui sont constltu~es de composés lipldique~ . .
non-ioniques et qui, de ce falt, forment des composition~ nouvelles permettant un encapsulage de substan¢es actives, utili~ables par e~emple en pharmacie, en alimentation ou en co~métique. ~'utili-~ation de composés non-ionlques pour constituer les sphérules d'en-capsulage préaente un intérèt non négligeable dans le ca3 où l'on déslre éviter que les sph~rules aient une surface extérleure chargée électriquement, 0 ~8 prése~te invention a donc pour obJet le produit indu~triel nouveau que constitue une dispersion de ~phérules ¢onstituées de couches moléculaires organisées de composés lipidi-ques, caractéri~ée par le fait que les compo~és lipidiques sont de 8 composés amphiphiles non-ionique 8 ~ ~ su~¢eptibles d'être dispersés dans l'eau et que les ~phérule~ ont un diamètre compris entre 100 et 50,000 ~ environ, Dans un mode préféré de réslieation, les sphérules de la di~persion selon l'invention enferment une phsse ~queuse ~
: encapsuler5 le~ ¢ompos~s lipidiques non-ionique~ ont un rapport 20 llpophile/hgdrophile tel que le compos~ gon~le dans la phsse . aqueuse ~ encap~uler en formant une phase lamellaire; le~ groupes : hydrophiles de~ composés lipidiques non-ioniques sont des groupes polyo~yéthylén~s, polyglycérolé~, de~ ester~ de polyols oxyéthyle-! né~:ou non et, par e~emple, - ~ de~ esters de ~orbitol poly-oxy~thyléné~; le~ compo~és lipidique~ non-ionique~ ~ont pris, de préf~rence, dans le groupe formé par :
- le~ éther~ de polygly~érol lin~aire~ ou ramifi~ de formule3 re~pectives :
R - (OCH2 CH OH CH2)n OH
et ` R~ 0 CH2 CH ~ - ~H
n étant un entier compri~ entre 1 et 6, R étant une chaine ali-phatique lin~aire ou ramifiée, saturée ou insaturée de 12 ~ 30 atome~ de carbone; le3 radicaux hydrocarboné~ de~ alcool~ de lanoline; le~ re~tes hydroxy-2-alkyle de~ -diol~ ~ longue cha~ne;
- les alcool~ gras polyoxyéthyl~nés;
- les e~ters de polyols oxyéthyléné~ ou no~ et, en particuller, le~ estera de sorbltol polyoxyéthyléné;
- le~ glycolipides d~origine naturelle ou synthétique, psr e~em-ple les c~rébrosides.
~a pha9e continue de la disper~ion, qui entoure le~
~ph~rules, est une pha~e aqueuse; la phase aqueuse encapsulée dan~ les ~phérule 8 e~t une solution aqueuse de sub~tance active, de préférence isoosmotique par rapport ~ la pha~e continue de la di~per~ion.
Diver~ additif~ peuvent être as~oci~s aux compos~
lipidique~ non-ioniqu~ en vue de modifier la perm~abilité ou la charge ~uperficielle des sph~rules. On citera a cet égard l'addi-tion éventuelle de~ aloool~ et diol~ ~ longue cha~ne, de~ ~érola, par exemple le ohole~térol, de~ amine~ a longue chaine et de leurs dérivé~ ammonium-quaternaire~, de~ dihydroxyalkyl-smine 8, des emine~ gra~se~ polyoxyéthylénée~, de~ ester~ d~amino-alcools longue chaine, de leurs sels et dérivé3 ammonium-quaternaires, des e3ter~ phosphoriques d'alcools gras, par exemple le dic~thyl-pho~phate de sodium, de~ alkylsulfstes, par e~emple le c~tyl-sulfzte de sodium, de certains polym~re~, tel~ que le~ polypep-tide~ et les protéines.
Ia pré~ente invention ~ également pour ob~et le produit indu~triel nouveau que oon~titue une di~persion de ~ph~rules con~titu~e~ de couches mol~culaire~ orgsnisée~ enfermant une phase aqueuse ~ encap~uler, ces couchec étant con~tituées d~au moins un compo3~ lipidique de formule X Y, X désignant un groupe hydroph~le ionique et Y un groupe lipophile, caract~ri~ée par le fait que le~ ~ph~rule~ ont un diamatre compris entre 1,000 ~ et 50,000 ~ environ.
Dans un mode préféré de réali~tion, la pha~e aqueuse a encapsuler eat une solution aqueuse de substance active ; le~
substan¢es actives de la phase aqueuse a encsp~uler sont des produits ~ action co métique; 18 phase continue de la dispersion e~t une pnase squeuse; la proportion du poids des ~phérule 9 par rapport aù poida de la phase continue de le disper~ion est comprise entre 0,01 et 0.5 environ; la phase continue de ~ dlspersion e~t avanta-geusement iaoo~motique par rapport ~ la phase aqueu~e en¢ap~ul~eaans le 9 sphérule~.
~ es ~ubstance~ actives, qui peuvent être encapsulées dans les ~ph~rules de3 deux types de disper~ion ¢i-dessus aéfinis, sont extrêmement vari~es et corre~pondent a celles ~ui ont été indiqu~es pr~cédemment pour la mise en oeuvre du procédé selon l'invention.
Il en r~sulte que les compositions peuvent ~tre utilisées dan~
des domsines vsri~s et, en particulier, en pharmscie et en cosméti-que.
Les di~persions aqueu~e~, qui viennent d'etre d~finies en dernier lieu, ont un int~rêt tout particulier en cosm~tique en raison du fait que l'utiliaation de ~phérules de grandes dimensions permet de r~duire les risque~ de passage de ces prép~ration~
travers la peau.
Il convient de noter que l'utilisation des dispersion~
aqueuses selon l'invention en cosm~tique, qu'il ~'agisse des di~persions contenant dea compos~s lipidiques non-ioniques ou des di~per~ion~ contenant des compos~s lipidiques ioniques, pr~sente un avantage consid~rable par rspport ~ l'utilisation bien connue des ~mul~ions. En effet, lorsque l'on d~a~re utili~er des pr~pars-tion~ contenant ~ la fois des corps gra~ et de l'eau, il e~tné~essaire, pour assurer 1~ stsbilité de l'~mul~ion, d'utili~er des compo~é~ amphiphiles ~mulsionnant~ pour a~surer la ~tabilité de~
dispersions. Il e~t connu que certains émulsionnant~ peuvent 8tre relati~ement irritant~ lorsqu'il~ sont appliqués sur la peau.
On 8 découvert, au cours des travau~ relatifs a 19 pr~ente invention, que cet ef~et des ~mul3ionnant~, pour une ~truoture chimique donn~e~ d~pend considérsblement de la forme 30U9 laquelle ils ~ont appliqués. Ainsl, on a pu mettre en ~vidence le fait qu'une énulsion eau/huile compo~e de 42% de perhydrosqualène, de 8% d'émulsionn~nt et de 50% d'eau est fortement irritante, alors qu'une di~per~ion aqueu~e ~ 8~o du m~me ~mul~ionnant a un indice d'irritation pratlquement inslgniflant et que le perhydrosqualane est ab~olument inoffensif. Il en r~sulte qu'il y a une synergie d'irritation, loraque l'on a en pr~ence un émul~ionnant et une phase huile. Ie~ disper~ion~ aqueuses selon l'invention permettent d'é~lter l'utili~ation simultan~e a'un ~mulsionnant et d'une huile ce qui con~titue un progr`es important dans le domaine de~ cosméti-que~.
Il convie~t de noter que l'on peut ajouter aux aisper-aions de aph~rules ~elon l'invention différents produits au~iliaires ayant pour but d'en modifier la pr~entation ou les oaractares organoleptiques, tels que de~ opacifiants, des gélifiants, de~
Drômes~ de 8 parfUm9 OU des colorants.
De façon g~n~rale, l'int~rêt des disper~ion~ selon l'ln-vention ré~ide dans le fait qu'elles permettent d'introduire des substances hydrophile3 dans un milieu e~sentiellement lipophile.
Il en r~ulte que, dans ce~ conditions~ celles-ci se trouvent masqu~e3, d'où un effet de protection vis-à-vis des diff~rents age~ts d'altération possibles: oxydant3, ~UC8 digeatif~ et plu9 g~néralement, compo3é~ r~actif~ vis-~-vis des ~ubstances encapsu-lée~. ~a p~n~tration et/ou 18 fixation des 3ub~tancea sctives peuvent être moaul~es par variation de la taille de~ globules et de leur charge ~lectrique. Ieur action peut également ~tre différée (effet retard). En outre, le fait qu'elles ~oient masqu~es, ~ermet ` - ` ` 1063908 de supprimer ou d'altérer sensiblement leurs caract~re~ orgsno-leptiques, en particulier le goût. Enfin, les lipides utilis~s dans ces pr~parations po~sèdent, par eu~-mêmes, une action bén~flque, par eYemple ~mollience, lubrification, lu~trage.
Pour mieux faire comprendre l'ob~et de l'invention, on va en décrire maintenant à tltre d'esemple~ purement illustratif~
et non limitatif~, plusieurs modes de mise en oeuvre.
E~EYPI~ 1 Dans un bsllon rond de 50 ml, on met en contact 500 ~g de trioléate de sorbitol o~yéthyl~né ~ 20 mole~ d'oYyde d'éthylène (produit Tween 85 commercialisé par la Sociét~ IaI Atla~) avec 0.335 ml d'une solution 0,7M de sorbitol et on homogénéi~e le m~lange, ~'o~périence e~t faite à la température amblante.
On ajoute ensuite 3 ml d'une ~olution aqueuse à 1% du produit connu 80U~ le nom commercial de Carbopol 934 (acide polya¢rylique r~ticulé psr le polyallyl~ucro~e, vendu par la Société "Goodrich"), ~e ballon, placé ~ur une 3ecoueuse, est sgité
énergi-quement pendant une heure.
La disper~lon obtenue e~t gélifiée le diamatre de~
~phérule~ e~t supérieur à 1 mioron.
EXE~PIE 2 Dans un ballon rond de 50 ml, on mélange intimement 250 mg d'alcool oléique oYy~thyléné ~ 10 mole~ (produit Bri~ 96 commer-ciali3~ par la Société ICI Atl~s), et 250 mg d'alcool oléique o~y-~thylén~ ~ 2 molee (produit Bri~ 92 comm~rciali~ par ln Soci~té
ICI Atlss); on met ensuite en contact le méla~ge obtenu avec 1 ml d'une solution 0.5M de glyc~rol, et on homog~n~ise le mélange.
~'e~p~rience est faite ~ temp~rature ambiante.
On a~oute en~uite 20 ml d'une ~olution 0.245 M (NaCl, KCl) Le ballon, plsc~ ~ur une secoueuse, eflt agité énergiquement pend~nt l heure.
~a disperYion obtenue est fluide e~ laiteu~e; le diam~tre * marque de commerce.
de~ sphérules est d'environ 1 micron.
Dan~ un ballon rond de 50 ml, on met en contact 500 mg du produit de formule générale:
R ~ ~2-CN ~ ON
~H2 R étant le r~dical alcoyle a~ 9 aloool~ de lanoline hydrogén~e et n ayant une ~aleur ~tati~tique moyenne de 3, avec 0.220 ml d'une ~olution 0,5M de pentaérythritol, et on homogénéise la mélange.
L'exp~rience e~t faite à temp~rature smbiante.
On s~oute eneuite 4 ml d'sau, le ballon, placé ~ur unQ
secoueu~e, est agité énergiquement pendant 30 minutes.
~a diapersion obtenue est d'aspect laiteux; le diamètre de~ sphérule~ eet 3upérieur ~ 1 micron.
Dan~ un ballon rond de 50 ml, on met en contact 500 mg du produit de ~ormule générale:
R ; OCH2-C~ ~ OH
~ ~H20H~n R étant le radlcal tétradécyle et n étant égal ~ 2, avec 0.75 ml ; d'une solution 0.4M de ~orbitol, et on homogénéise le mélange.
~'exp~rience est faite ~ 40C.
On a~oute ensuite 4 m- d'eau. Le ballon, placé sur une ~ecoueuse, est agité ~nergiquement pendant 30 mn.
La dispersion obtenue est claire, après pa~age aus ultra~ons~ le diamètre de~ ~phérules e~t inf~rieur ~ 1 mi¢ron.
Dan~ un ballon rond de 50 ml9 on met en contact 500 mg du produit de formule g~n~rale:
- 12 _ f R ~ OCH2-CH ~ OH
R étant le radical hexad~cyle et n étant égsl ~ 2, avec 0.335 ml d'une 301ution 0.3M de chlorhydrate de cy~téine, et on homog~néise le mélange. L'eYpérience e~t faite ~ 55C.
; Cn ajoute ensuite 4.1 ml d'une ~olution 0,145 M (NaCl, KCl). ~e b~llon, plac~ ~ur une ~eooueuse, e~t aglt~ ~nergiquement pendant 3 heures, La di~persion obtenue e~t pratiquement limp~de ~ 55C;
le diamatre des sphérule~ e~t d'environ 2 micron~. En refroidi~ssnt lentement la di~persion ~ la temp~rature ambiante, on obtient un gel opaque, blan¢.
La disper~ion pr~lev~e a 55C peut être diluée avec une ~olution i~oo~motique ou non, contenant un ~pai~3issant tel que des gomme~ ou polym~res; on obtient une solution légarçment opaque:
le r~pport de dilution étant choi~i ~uivant l'aapect de la solution ~ue l'on d~ire obtenir.
~XEMPIE 6 Dans un ballon rond de 50 ml, pla¢~ dan~ un bain-marie a 55C, on met en contact 500 mg du produit de formule générale:
R t CH2 CH toH
~ CH20H/n R étant le r~dical hesad~cyle et n ~tant égal ~ 2, avec 10 ml d'une ~olution 0.3~ de m~thionine, et on homogénéi~e le m~lange. ~'eYp~-rience e~t faite ~ 55C.
Le ballon, placé ~ur une secoueu3e, est agité énergique-2,091,516 and in the certificate of addition 94,928.
It is possible to use an aqueous phase to be encapsulated comprising both active substances of all kinds and, in particular, substances of pharmaceutical or food interest, or substances with cosmetic activity. Active substances for example, with regard to the substance cosmetic; skin and skin care products hair, for example humectants such as glycerin, ~ orbitol, pentserythritol, ino ~ itol, pyrrolidone acid-carbo ~ ylique and its salts; browning agents ~ artificial sage tel3 that 18 dihydroxyacetone, erythrulo ~ e, glyceraldehyde, the ~
~ -dialdehydes such as tartaric aldehyde (this ~ prQduits can ~ be possibly associated ~ dye ~) t of ~ anti agents ~ olai-re ~ hydro ~ soluble ~; ~ antiperspirants, ~ deodorants, a3trin-gents ~ products ~ r ~ hcoatant ~ tonics, atritizers, keratolytics, depila ~ oire ~ 5 scented eaus ~ of ~ extracts of tissue ~ animals or plants; such as prot ~ ine ~, polgsaccharide ~, amniotic liquid; water-soluble dyes from ~ snti- agents pelli ¢ ulaires, agents ~ antiseborrhoeic, oxidants (agents discoloration) like osygenic water ~ e, ~ reducers such as thioglycolic acid and ae ~ salt ~. Like ~ ubstance ~ sctives pharmaceutical include: lee vita ~ ines, the ~ hormones, enzymes, (for example, superoxide dismuta ~ e), vacins, anti-inflammatory drugs (hydrocortisone, for example), antibiotics, that ~, the bsct ~ rioide ~, It is a good idea that we will go, according to the sub-totive aotive contained dan3 the aqueous phase ~ encapauler, lipid ~ susceptible ~ to encap ~ uler stably the aqueous phase ~ e considered. So that the lipid ~ constituting the pha ~ e lamellar give spherule ~ stable, it is ~ necessary ~ saire ~ util there is a sufficient lst ~ rale interaction between the lipid chains which, placed c8te ~ cote, constitute lee layers or sheets of spherules, that is to say that the Van der Waals forces between the chain ~ as ~ urent sufficient cohesion of the sheets. This con-dition is satisfied for the ~ lipids with the characteristics indicated ~ dan ~ the general definition of the procedure ~ c ~ above.
~ es lipids can be used ~ in the process ~ ~ according to the invention-tion belong to the class of emulsifiers of the water type dan oil.
~ - `
The process according to the invention makes it possible to obtain dis-persion ~ of aphérules which are constltu ~ es of lipldique compounds ~. .
non-ionic and which, from this falt, form ~ new compositions allowing encapsulation of active substances, usable by e ~ example in pharmacy, food or cosmetics. ~ 'useful ~ ation of non-ionic compounds to constitute the spherules of-encapsulation has a significant interest in the ca3 where deslre avoid that the sph ~ rules have a charged exterior surface electrically, 0 ~ 8 presents ~ te invention therefore aims the product indu ~ triel new that constitutes a dispersion of ~ pherules ¢ made up of organized molecular layers of lipidi-ques, caractéri ~ ée by the fact that the lipid compo ~ és are of 8 non-ionic amphiphilic compounds 8 ~ ~ su ~ ¢ eptibles to be dispersed in water and that the ~ pherule ~ have a diameter between 100 and 50,000 ~ approximately, In a preferred mode of resolution, the spherules of the di ~ persion according to the invention enclose a phsse ~ queuse ~
: encapsulate5 the ~ ¢ ompos ~ s non-ionic lipids ~ have a relationship 20 llpophile / hgdrophile such as the compound ~ gon ~ le in the phsse . aqueous ~ encap ~ uler by forming a lamellar phase; the ~ groups : hydrophilic ~ non-ionic lipid compounds are groups polyo ~ yéthylén ~ s, polyglycérolé ~, de ~ ester ~ de oxyéthyl polyols-! born ~: or not and, for example, - ~ of ~ esters of ~ orbitol poly-oxy ~ thylenated ~; the ~ compo ~ és lipidique ~ non-ionic ~ ~ took, of preferably in the group formed by:
- the ~ ether ~ of polygly ~ erol lin ~ area ~ or ramifi ~ of formula3 re ~ pective:
R - (OCH2 CH OH CH2) n OH
and `R ~ 0 CH2 CH ~ - ~ H
n being an integer compri ~ between 1 and 6, R being a chain ali-phatic flax ~ area or branched, saturated or unsaturated from 12 ~ 30 carbon atom; le3 hydrocarbon radicals ~ of ~ alcohol ~ of lanolin; the ~ re ~ your hydroxy-2-alkyl of ~ -diol ~ ~ long cha ~ ne;
- alcohol ~ fatty polyoxyethyl ~ born;
- e ~ ters of oxyethylenated polyols ~ or no ~ and, in particular, the ~ polyoxyethylenated sorbltol ester;
- the ~ glycolipids of natural or synthetic origin, psr e ~ em-ple c ~ rebrosides.
~ a pha9e continues to disper ~ ion, which surrounds the ~
~ ph ~ rules, is an aqueous pha ~ e; the encapsulated aqueous phase dan ~ les ~ pherule 8 e ~ t an aqueous solution of active sub ~ tance, preferably isoosmotic compared to ~ the pha ~ e continues the di ~ per ~ ion.
Diver ~ additive ~ can be as ~ oci ~ s to the compos ~
lipid ~ non-ionic ~ to change the permeability or charge ~ uperficiel des sph ~ rules. In this regard, the addi-possible tion of ~ aloool ~ and diol ~ ~ long chain ~ ne, of ~ ~ erola, for example the ohole ~ terol, of ~ long chain ~ amine ~ and their derivative ~ quaternary ammonium ~, of ~ dihydroxyalkyl-smine 8, emine ~ gra ~ se ~ polyoxyethylenated ~, de ~ ester ~ d ~ amino-alcohols long chain, their salts and ammonium-quaternary derivatives3, e3ter ~ phosphoric fatty alcohols, for example dic ~ thyl-pho ~ phate de sodium, de ~ alkylsulfstes, e ~ example c ~ tyl-sodium sulfzte, some polym ~ re ~, such as ~ polypep-tide ~ and proteins.
Ia pre ~ ente invention ~ also for ob ~ and the product industrial new that oon ~ tituates a di ~ persion of ~ ph ~ rules con ~ titu ~ e ~ of soft layers ~ circular ~ organized ~ enclosing a phase aqueous ~ encap ~ uler, these couchec being con ~ constituted of ~ at least one lipidic compound of formula XY, X denoting a group hydroph ~ ionic and Y a lipophilic group, caract ~ ri ~ ée by the fact that the ~ ~ ph ~ rule ~ have a diameter between 1,000 ~ and 50,000 ~ approx.
In a preferred embodiment of ~ tion, the aqueous pha ~ e has encapsulate an aqueous solution of active substance; the ~
active substances of the aqueous phase to be encapsulated are products ~ cosmetic action; 18 continuous phase of the dispersion e ~ t a scaly penis; the proportion of the weight of ~ pherule 9 compared aida poida of the continuous phase of the disper ~ ion is between 0.01 and 0.5 approximately; the continuous phase of ~ dlspersion e ~ t avanta-giously iaoo ~ motique compared to ~ the aqueous phase ~ e in ap ~ ul ~ eaans the 9 spherule ~.
~ es ~ ubstance ~ active, which can be encapsulated in the ~ ph ~ rules of 3 two types of disper ~ ion ¢ above defined, are extremely varied and correspond to those which have been indicated pr ~ previously for the implementation of the method according to the invention.
As a result, the compositions can be used in domsines vsri ~ s and, in particular, in pharmscie and cosmeti-than.
The aqueous dispersions which have just been defined in last place, have a very special interest in cosmetics due to the fact that the use of ~ large pherules reduces the risk ~ of passage of these prep ~ ration ~
through the skin.
It should be noted that the use of dispersions ~
aqueous according to the invention in cosm ~ tick, it ~ 'acts di ~ persions containing non-ionic lipid compounds or di ~ per ~ ion ~ containing ionic lipid compounds, present a considerable advantage compared to the well-known use ~ mul ~ ions. Indeed, when one d ~ a ~ re utili ~ pr ~ pars-tion ~ containing ~ both gra ~ bodies and water, it e ~ tné ~ essaire, to ensure 1 ~ stsibility of ~ mul ~ ion, to use ~ er compo ~ é ~ amphiphiles ~ emulsifying ~ to a ~ secure the ~ tability of ~
dispersions. It is known that certain emulsifiers can 8tre relati ~ ement irritant ~ when ~ are applied to the skin.
We discovered 8, during the work related to 19 present invention, that this ef ~ and ~ mul3ionnant ~, for a ~ truoture chemical given ~ hangs considerably from the form 30U9 which they ~ applied. So we were able to highlight the fact that a water / oil enulsion composed of 42% perhydrosqualene, 8% emulsion and 50% water is highly irritating, so that a di ~ per ~ ion aqueu ~ e ~ 8 ~ o of the same ~ mul ~ ionnant has an index practically insignificant irritation and that perhydrosqualane is absolutely harmless. As a result, there is a synergy irritation, loraque we have in pr ~ ence an emulsifier and a oil phase. Ie ~ disper ~ ion ~ aqueous according to the invention allow é ~ lter the utility ~ simultaneous ation ~ e a'un emulsifier and an oil which constitutes significant progress in the field of ~ cosmeti-that ~.
It should be noted that one can add to the aisper-aions of aph ~ rules ~ according to the invention different products in ~ ilaries intended to modify the presentation or the oaractares organoleptics, such as ~ opacifiers, gelling agents, ~
Dromes ~ of 8 parfUm9 OR dyes.
In general, the int ~ stop disper ~ ion ~ according to ln-vention re ~ ide in the fact that they allow to introduce hydrophilic substances3 in a medium e ~ substantially lipophilic.
As a result, under these conditions these are found.
mask ~ e3, hence a protective effect vis-à-vis diff ~ rents age ~ possible alteration ts: oxidant3, ~ UC8 digestive ~ and plu9 g ~ generally, compo3é ~ r ~ active ~ vis- ~ -vis des ~ ubstances encapsu-lée ~. ~ ap ~ n ~ tration and / or 18 fixation of 3ub ~ tancea sctives can be moaul ~ es by varying the size of ~ globules and of their electrical charge. Their action can also be deferred (delay effect). In addition, the fact that they are hidden, allows `` - '' 1063908 to remove or significantly alter their characteristics ~ re ~ orgsno-leptics, especially the taste. Finally, the lipids used in these pr ~ preparations po ~ sede, by eu ~ -same, a ben ~ flque action, by eYemple ~ mollience, lubrication, lu ~ trage.
To better understand the ob ~ and the invention, we will now describe it to your example ~ purely illustrative ~
and not limiting ~, several modes of implementation.
E ~ EYPI ~ 1 In a round bsllon of 50 ml, contact 500 ~ g sorbitol trioleate o ~ yethyl ~ born ~ 20 mole ~ ethylene oxide (Tween 85 product marketed by the company ~ IaI Atla ~) with 0.335 ml of a 0.7M solution of sorbitol and homogenized ~ e m ~ diaper, ~ 'o ~ e ~ t experience made at the amblante temperature.
Then added 3 ml of a ~ 1% aqueous solution of known product 80U ~ the trade name of Carbopol 934 (acid polyaryl r ~ crosslinked psr polyallyl ~ ucro ~ e, sold by "Goodrich" company), ~ e balloon, placed ~ on a 3coueuse, is sgited energetically for an hour.
The disper ~ lon obtained e ~ t gelled the diameter of ~
~ pherule ~ e ~ t greater than 1 mioron.
EXE ~ PIE 2 Intimately mix 250 mg in a 50 ml round flask oYy oleic alcohol ~ thylenated ~ 10 mole ~ (Bri product ~ 96 commercial-ciali3 ~ by the company ICI Atl ~ s), and 250 mg of oleic alcohol o ~ y-~ thylén ~ ~ 2 molee (Bri product ~ 92 comm ~ rciali ~ by ln Soci ~ té
HERE Atlss); then the mela ~ ge obtained with 1 ml is brought into contact of a 0.5M solution of glyc ~ rol, and the mixture is homog ~ n ~ ed.
~ 'e ~ p ~ rience is made at room temperature.
We have ~ 20 ml of ~ 0.245 M solution (NaCl, KCl) The balloon, plsc ~ ~ ur a shaker, was vigorously agitated during the hour.
~ A disperYion obtained is fluid e ~ mileu ~ e; the diameter * trademark.
of ~ spherules is approximately 1 micron.
Dan ~ a 50 ml round flask, 500 mg of product of general formula:
R ~ ~ 2-CN ~ ON
~ H2 R being the r ~ dical alkyl a ~ 9 aloool ~ of hydrogenated lanolin ~ e and n having an average ~ tat ~ value of 3, with 0.220 ml of a ~ 0.5M pentaerythritol solution, and the mixture is homogenized.
The experience is made at room temperature.
We are left with 4 ml of water, the flask placed on our side shaker ~ e, is stirred vigorously for 30 minutes.
~ A diaphragm obtained is milky in appearance; the diameter of ~ spherule ~ eet 3upérieur ~ 1 micron.
Dan ~ a 50 ml round flask, put 500 mg in contact of the product of ~ general formula:
R; OCH2-C ~ ~ OH
~ ~ H20H ~ n R being the tetradecyl radlcal and n being equal to 2, with 0.75 ml ; of a 0.4M solution of ~ orbitol, and the mixture is homogenized.
~ 'experience is made ~ 40C.
We then have ~ 4 m of water. The ball, placed on a ~ stripper, is agitated ~ energetically for 30 minutes.
The dispersion obtained is clear, after pa ~ age aus ultra ~ ons ~ the diameter of ~ pherules e ~ t ~ lower ~ 1 mi ¢ ron.
Dan ~ a 50 ml round flask9 we put 500 mg in contact of the product of general formula:
- 12 _ f R ~ OCH2-CH ~ OH
R being the hexad ~ cyle radical and n being ésl ~ 2, with 0.335 ml of a 0.3M 301ution of cy ~ tine hydrochloride, and we homog ~ neise The mixture. The eYperience was ~ 55C.
; Then add 4.1 ml of a 0.145 M solution (NaCl, KCl). ~ eb ~ llon, place ~ ~ ur a ~ eooueuse, e ~ t aglt ~ ~ energetically during 3 hours, The di ~ persion obtained is almost limp ~ ~ 55C;
the diameter of the spherule ~ e ~ t of about 2 micron ~. While cooled ~ ssnt the dispersion slowly at room temperature, we obtain a opaque, white gel.
The disper ~ ion pr ~ lev ~ ea 55C can be diluted with a ~ olution i ~ oo ~ motique or not, containing a ~ pai ~ 3issant such as gum ~ or polym ~ res; we obtain a slightly opaque solution:
the r ~ dilution report being chosen ~ i ~ following the aapect of the solution ~ ue we d ~ ire get.
~ XEMPIE 6 In a 50 ml round flask, placed in a water bath at 55C, 500 mg of the product of general formula is brought into contact:
R t CH2 CH toH
~ CH20H / n R being the hesad ~ cyle rdical and not being equal to 2, with 10 ml of a ~ 0.3 ~ solution of m ~ thionine, and homogeni ~ e the m ~ lange. ~ 'eYp ~ -rience was made ~ 55C.
The ball, placed on a shaker, is energetically agitated.
3 ment pendant 3 heures ~ 55C.
Ia dispersion obtenue est limpide; le diamatr~ de~
~phé~ule3 e~t d'environ 1 micron. Par refroidiseement ~ la .
_ 13 -tempér~ture ambisnte~ on obtient une gel~e blanche.
Dana un ballon rond de 50 ~1, on met en contact 500 mg du produit de formule générale:
R t OCH2-CH
CH20H/n R ~tant le radicsl alkyle de l~alcool isoatéarylique, n syant une valeur ~tati~tique moyenne de 2, avec 5 ml d'eau, et on homogén~ise le m~lange. ~'expérience est faite ~ température ambi~nte.
Ie ballon, plac~ ~ur une ~ecoueuse, eat agité énergique-ment pendant 4 hQures.
Ia di~persion obtenue e~t laiteu~e; le diamatre de~
~phérule~ est d'environ 5 micron~.
Ia disper~ion peut ~tre soumise auY ultra-sons, afin de r~duire notablement 18 taille de 8 ~phérules.
Dsns un ballon rond de 50 ml, on disaout 83.2 mg (200 ~-moles) du produit de formule générsle:
R ~ CH2- ~ ~ OH
R 6tant le radical alkyle de l'alcool~oléique et n ~tant égal à 2, dan~ 2 ml d'un mélange chloroforme-m~thanol dan~ le rapport 2:1.
On ~vapore le ~olvant ~ l'aide d'un ~vaporateur rotatif, et on ~limlne le~ dernière~ trace~ de solvsnt par passage ~ la pompe à palette pendant une heure.
Qn m~t en contact 10 ml d'une solution 0.3M de gluco~e avec le lipide. Ie ballon, mis sur une aecoueuse, e~t agité
fortement dursnt 4 heure~. ~'e~périence est ~aite ~ température ambiante.
La di~per~ion e~t soumise auY ultra-son~ durant 20 minutes, afin de réduire le diamètre de~ sphérules ~ une valeur inf~rieure ~ 0.5 micron. On filtre alors la dispers$on sur colonne de gel "Sephadez G 50 coarse" gonflé dans une solution 0.145M
(NaCl~ KCl). La solution obtenue est légère~ent bleut~e.
Dans un ballon rond de 50 ml, on mélange intimement 58 mg du produit de formule g~nérale:
R ~ OCH2_CH ~ OH
~ ~ 2~ Jn R étant le radlcal alkyle de l'alcool i~ost~arylique, n étant égal ~ 2, avec 58 mg du produit de formule générale :
R - ( OC~2_CH ~ OH
~ CH2H n R étant le radlcal alcoyle de l'alcool "ieo~t~arglique", n étant ~gal ~ 6, et on met en conta¢t le m~lange obtenu ave¢ 10 ml d~une solution IM de glucose. Llexp~rience est faite ~ la température ambiante. Le bsllon, placé sur une secoueuse, est fortement agité
durant 4 heure 9, ~ a disper~ion obtenue est très fine; les sphérules ont un diamètre d'environ 1 micron. On peut ~oumettre 1~ disper~ion au~
ultra-sons durant 30 mn, afin d'abaisser la taille des sphérules une valeur inf~rieure à 0.5 micron.
Ie~ dispersions ayant, soit de~ sphérules d'un diamètre 3upérieur ~ 1 micron, ~oit de~ sph~rule~ d'un diamatre inf~rieur ~ 0,5 micron, sont filtrées eur colonne de gel "Sephadex G 50 coarse" gonfl~ dan~ une solution 0.475 M (NaCl, KCl).
Dan~ un ballon rond de 50 ml, on met en contact 500 mg :
monolauryl-~ther de t6tra~thylane-glycol, avec 0.4 ml d'une ~olu-tion 0.3M de glucose~ et on homogén~ise le mélunge. ~'eYpérlence est faite ~ température ~mbiante.
On s~oute enauite 5 ml d'une ~olution 0~145 M (NaCl~ KCl~.
Le ballon, placé sur une secoueu3e, est agit~ énergique-ment pendant 15 minutes.
La disper~ion obtenue est limpide; le diam~tre dea sphé-rulea e~t d'environ 1 micron, EXE~PIE 11 Dan~ un ballon rond de 50 ml, on met en contact 500 mg du produit de *ormule gén~rale:
R t OCH2-lH ~ OH
CH20H/ n ' .
R étant le radioal heYad~cyle ~t n ayant une valeur ~tati~tique moyenne de 3, svec 0.5 ml d'une ~olution à 50 mg/ml ae Crotéine C (protéine de poid~ moléculaire d'environ 10,000, commercialis~e par la So¢i~té 'ICRODAll), On homogén~ise le mélange. ~'expérien¢e e~t faite ~ 60C.
On a~oute en~uite 4 ml d'une ~olution 0.145 M (NaCl~ KCl).
~e bsllon, plac~ ~ur une ~ecoueuse, est agité ~nergique-ment pendant 3 heures.
IB di~persion obtenue est limpide; le diam~tre de 9 ~phé-rules est d'environ 1 micron. Par refroidiasement lent ~ la tempé-rature ambiante, on obtient un gel op~que blanc.
-Dan~ un ballon rond de 50 ml, on met en contact 300 mg de sphingomyéline, avec 0.350 ml d'une aolution 0.3 M de glucose, et on homogénéise le m~lange. ~'e~p~rience est faite ~ la tempéra-ture ambisnte.
On a~oute en~uite 5 ml d'une solution 0.145 M (NaCl,KCl) * marque de commerce.
B~ - 16 -Le ballon, pl9c~ ~ur une ~ecoueuse, e~t agit~ énergiquement pen-dant 2 heure~.
~ a dispersion obtenue est laiteu~eS le diam~tre des ~phérule~ est d'environ 2 micron~.
IB di~persion peut être ~oumise aux ultra-~on~ durant 1 heure afin de diminuer le diamatre des sphérules.
Dan~ un ballon rond de 50 ml, on mélange intimement 300 mg du produit obtenu par distillation moléculaire~ de formul~
générale:
R { OCH2-CH ~ 0 CH2 n R ~tant le rsdicsl alkyle de l'alcool oléique et n étant ~gal ~
2; 150 mg de cholest~rol; 50 mg d'une amine de ~ormule gén~rale:
Rcoo(cH2cH2o)ncH2c ~ \ C H
RCOO ~tant le re~te du ooprah et n étsnt un nombre camprie entre 2 et 5, et on met en contact le mélange obtenu avec 0.5 ml d'une ~olution 0.3 M de ~orbitol; on homogén~ise le m~lange. ~'expérience est faite ~ la température smbiante.
`~ On a~oute ensuite 4 ml d'une ~olution 0.145 M (NaCl, KCl).
~e ballon, placé ~ur une secoueu~e, est agit~ énergi~ue-ment pendant 4 heures.
~a di~per~ion obtenue e~t opalescente; le diamatre des -~ sphérules est d'environ 2 microns.
Dans un ballon rond ae 50 ml, on met en contact 425 mg du produit, deformule générale:
lOb3908 R _ ( OCH2_CH ~ - OH
R étant le radical slkyle de l'alcool oléique et n ~tant un nombre égal ~ 2, et 75 mg d'une amine de ~ormule suivante :
R _ ~ OCH2-~H ~ -OCH2CHOH _CH2N~
R étant le radical ol~yl et n ayant une valeur ststistique moyenne de 1, avec 0.5 ml d'une sol~tion 0.3 M de glucose, et on homogé-néi~e le mélange. ~'e~périence e~t faite ~ température ambiante.
Cn ajoute en~uite 4 ml d'une solution 0.145 M (NaCl~KCl).
Ie ballon, placé eur une ~ecoueu~e, est agité ~nergique-ment pendant 4 heure~.
~a disper~ion obtenue est op~queS le diamètre de~ ~ph~-rules est ~upérleur ~ 2 micron~.
Ia di~peraion peut 8tre soumise aux ultra-~ons, la taille de~ ~phérule~ devenant alor~ inf~rieure au mi¢ron.
Dans un ballon rond de 50 ml, 300 mg de ~phingomyéline ~ont mi~ en contact a~ec 0.350 ml d'une ~olution 0.3M d'scide a~cor-bique, et on homogé~éi~e le mélange. L'e~périence e~t faite temp~rature ambiante.
On ajoute ensuite 2,650 ml d'-me solution 0.145M
(NaCl,~Cl). ~e ballon, pl~c~ ~ur une ~e¢oueu~e, e~t agité ~nergi-quement pendant 4 heure~.
Ia di~per~ion obtenue e~t laiteu~e; le diamatre de~
aph~rule~ e~t d'en~iron 2 microns.
Si on 1~ d~sire, la di~per~ion peut 8tre filtr~e sur colonne de gel "Sephadex G 50 coar~e" gonfl~ dan~ une solution 0.145 M (NaCl,KCl).
- 18 _ E ~IE 16 Dans un ballon rond de 50 ml, 142 mg du sel de Na de la I~2(alcoyl_suif)_N dodécyl-N(N', N'_diéthylaminoéthyl)-asparagine 80nt dissous dan~ 2 ml d'un m~lange chloroforme-méthanol dans le rapport 2sl~ On évapore le solvant ~ ide d'un évsporateur rota-tif, pui~ on élimine le~ derniares traces de sol~nt en soumettant le produit pendant une heure ~ la pression réduite donnée par une pompe ~ palettes, On met en contsct 10 ml d'une solution 0 3M de glucose ave¢ le lipide.
~ e ballon mis sur une secoueu~e, est fortement agit~
durant 4 heurea. ~'expérience e~t faite ~ la température ambiante ~a taille de~ ~phérule~ e~t d'environ 1 micron. Ia aispersion est alors flltr~e ~ur colonne de gel "Sephadex G 50 coarse" gonflé
dans une solution 0.145 ~ (NaCl,KCl).
Dan~ un ballon de 50 ml, on dis~out 80 mg du produit de for~ule g~nérale:
R ~ CH2-PH ~ OH
CH20H/n R ~tant le radical he~décyle et n étant égal à 2, 10 mg de cholest~rol et lO mg de dicétyl-phosphate dans 2 ml d'un m~lange chloroforme/méthanol dans le rapport 2/1.
5n évapore le solvant à l'~ide d'un évaporateur rotatif et on ~limine le~ derni~re~ trace~ de sol~ant par pa~3age ~ la pompe . ~
pslette~ pendant 1 heure.
On met en contact 10 ml d'une solution 0.15 M du sel de sodium de l'acide pyroglutamique avec le~ lipide~. ~e ballon, mi~
sur une secoueuae, e~t agité fortement durant 2 heure~ BU bsin-marie ~ 55C pUi3 en refroidissant progre~sivement jusqu'~ revenir ~ 18 temp~rature ambiante.
~a di~persion est ~oumise auy ultrason~ pendant l heure une temp~rsture maintenue pr~s de 19 température ambiante. Cn filtre ~lors la di~per3ion sur une colonne de gel "Sephadex G 50 coarse" gonflé d~ns l'eau distillée. r ~a di~persion obtenue e~t fluide et clslre aprac pas~age auY ultrasons ; le diamatre des sphérules est inférieur ~ 1 micron.
Dan~ un ballon rond de 50 ml, on m~lange intimement 240 mg du produit de formule génér~le :
~
R t OCH2-qH ~ OH
2 n R étant le radical alcoyle de~ alcools de lanoline hydrogénée et n aysnt une valeur statistique moyenne de 3, et 60 mg de cholesté-rol.
On met en contact le mélange obtenu avec 0.4 ml d'une ~olution 0.15 M du ~el de sodium de l'acide pyroglytamique et on homogéné~se le m~lange. ~'espérience est faite à 45C On ajoute en~uite 4 6 ml d'une ~olution de chlorure de sodlum ~ 9 /oo.
~e ballon, plac~ dans u~ bain-marie, est agité énergique-ment ~ l'aide d'une ~ecoueu~e pendant 2 heures à 45C puia en refroidissant progre~sivement ~u~qu'~ revenir ~ la température smbiante.
~a dispersion obtenue est fluide et laiteu3e; le diamètre des sphérules est supérieur ~ un micron EXEMPIE l9 Dan~ un ballon rond de 50 ml, on mélan6e intimement 200 mg du produit de formule générale :
~0 R
C~2 ~ - .
R ~tant le radi~sl he~adécyle et n étant ~gal ~ 2, 25 mg de cholest~rol et 25 ~g de dlcétyl-phonphate; on m2t en contact le m~lange obtenu svec 0.3 ml d'une ~olution d'aldéhyde tartrique ~
10 % et on homogénise le mélange. ~'eYpérience est faite ~ 55C.
On ajoute en~uite 4.7 ml d'~ne solution 0.145 M (NaCl~KCl).
Ie ballon, placé dan~ un bain-mzrie, est agit~ énergique-ment ~ l'aide d'une ~ecoueu~e pendant 2 heures ~ 55C pui~ en refroidissant progres~ivement jusqu'~ revenir à 1~ température ambiante.
La di~per~ion obtenue e~t g~lifi~e et d'a~pect légèrement bleuté, ~ 'spplication ~imultan~e sur la peau de oette di~persion de niosome~ et d'une solution aqueu~e à même concentration finale en aldéhydetartrique, permet d'appr~cier deuY effets de~ niosome~
le~quel~, renforçant considérablement la coloration développ~e, améliorent nettement la tenue de cette coloration au~ lavage~
l'eau et aux détergent~.
Il e~t bien entendu que le~ mode~ de réali~ation ci-des~u~
deorit~ ne sont auounem~nt limitatifs et pourront donner lieu a toute~ modifications désirable~, ssns aortir pour cela du cadre de l'invention.
. ' .
.--;
. 3 times for 3 hours ~ 55C.
The dispersion obtained is clear; the diamatr ~ of ~
~ phe ~ ule3 e ~ t of about 1 micron. By cooling ~ the .
_ 13 -tempér ~ ture ambisnte ~ we get a white gel ~ e.
In a 50 ~ 1 round flask, 500 mg are brought into contact of the product of general formula:
R t OCH2-CH
CH20H / n R ~ as the alkyl radicsl of isoatearyl alcohol, n being a value ~ tati ~ tick average of 2, with 5 ml of water, and we homogenize the mixture. ~ the experiment is made ~ ambient temperature ~ nte.
Ie balloon, placed ~ ~ a ~ listener, eat energetic agitated-lie for 4 hours.
Ia di ~ persion obtained e ~ t mileu ~ e; the diameter of ~
~ pherule ~ is about 5 micron ~.
Ia disper ~ ion can ~ be subjected to ultrasound Y, in order to significantly reduce 18 size of 8 ~ pherules.
In a 50 ml round flask, we say 83.2 mg (200 ~ -moles) of the product of formula genersle:
R ~ CH2- ~ ~ OH
R being the alkyl radical of the oleic alcohol and n ~ being equal to 2, dan ~ 2 ml of a chloroform-m ~ thanol dan ~ mixture 2: 1.
We ~ vaporize the ~ olvant ~ using a ~ rotary vaporizer, and we ~ limlne the ~ last ~ trace ~ of solvsnt per pass ~ the pump palette for one hour.
Qn m ~ t in contact 10 ml of a 0.3M solution of gluco ~ e with lipid. Ie balloon, put on a seamer, was agitated strongly lasts 4 hours ~. ~ 'e ~ experience is ~ aite ~ temperature ambient.
The di ~ per ~ ion e ~ t subject to ultra-sonYY during 20 minutes, in order to reduce the diameter of ~ spherules ~ a value lower ~ 0.5 micron. We then filter the dispersion $ on on column of gel "Sephadez G 50 coarse" swollen in a 0.145M solution (NaCl ~ KCl). The solution obtained is light ~ ent blue ~ e.
Intimately mix 58 mg in a 50 ml round flask of the product of general formula:
R ~ OCH2_CH ~ OH
~ ~ 2 ~ Jn R being the radlcal alkyl of alcohol i ~ ost ~ aryl, n being equal ~ 2, with 58 mg of the product of general formula:
R - (OC ~ 2_CH ~ OH
~ CH2H n R being the alkyl radlcal of alcohol "ieo ~ t ~ arglique", n being ~ gal ~ 6, and the mixture obtained is contaminated with 10 ml of a IM glucose solution. Llexp ~ rience is made at temperature ambient. The bsllon, placed on a shaker, is strongly agitated for 4 hours 9, ~ a disper ~ ion obtained is very fine; the spherules have a diameter of about 1 micron. We can ~ oumettre 1 ~ disper ~ ion to ~
ultrasound for 30 min, in order to reduce the size of the spherules a value lower than 0.5 micron.
Ie ~ dispersions having either of spherules of a diameter 3uperior ~ 1 micron, ~ eye of ~ sph ~ rule ~ of a lower diameter ~
~ 0.5 micron, are filtered eur "Sephadex G 50 gel column coarse "swelling ~ dan ~ 0.475 M solution (NaCl, KCl).
Dan ~ a 50 ml round flask, put 500 mg in contact :
monolauryl- ~ ther of tetra ~ thylane-glycol, with 0.4 ml of a ~ olu-tion 0.3M of glucose ~ and we homogenize the melunge. ~ 'eYpérlence is made ~ temperature ~ mbiante.
We enauite 5 ml of a ~ 0 ~ 145 M solution (NaCl ~ KCl ~.
The ball, placed on a shaker, is acted ~ energetic-lie for 15 minutes.
The disper ~ ion obtained is clear; the diameter of the sphere rulea e ~ t of about 1 micron, EXE ~ PIE 11 Dan ~ a 50 ml round flask, put 500 mg in contact of the product of * general formula:
R t OCH2-1H ~ OH
CH20H / n '.
R being the radioal heYad ~ cyle ~ tn having a value ~ tati ~ tick average of 3, with 0.5 ml of a ~ 50 mg / ml solution of Crotein C (molecular weight protein of about 10,000, marketed by So ¢ i ~ té 'ICRODAll), The mixture is homogenized. ~ 'experiment ~ t made ~ 60C.
We have ~ ute en ~ uite 4 ml of a 0.145 M solution (NaCl ~ KCl).
~ e bsllon, place ~ ~ ur a ~ peeler, is agitated ~ energetic-lie for 3 hours.
IB di ~ persion obtained is clear; the diameter of 9 ~ phe-rules is about 1 micron. By slow cooling ~ temperature-rature ambient, an op ~ white gel is obtained.
-Dan ~ a 50 ml round flask, put in contact 300 mg sphingomyelin, with 0.350 ml of a 0.3 M glucose solution, and homogenize the m ~ mixture. ~ 'e ~ p ~ rience is made ~ the tempera-ambient ture.
We have ~ everything in ~ 5 ml of a 0.145 M solution (NaCl, KCl) * trademark.
B ~ - 16 -The balloon, pl9c ~ ~ ur ~ a skinning machine, e ~ t acts ~ energetically thought-for 2 hours ~.
~ A dispersion obtained is milky ~ eS the diam ~ tre ~ pherule ~ is about 2 micron ~.
IB di ~ persion can be ~ omitted to ultra- ~ on ~ during 1 hour to reduce the diameter of the spherules.
Dan ~ a 50 ml round flask, we mix intimately 300 mg of the product obtained by molecular distillation ~ of formula ~
general:
R {OCH2-CH ~ 0 CH2 n R ~ both the rsdicsl alkyl of oleic alcohol and n being ~ gal ~
2; 150 mg cholest ~ rol; 50 mg of an amine of general ormule:
Rcoo (cH2cH2o) ncH2c ~ \ CH
RCOO ~ being the re ~ te of ooprah and n is not a number plotted between 2 and 5, and the mixture obtained is brought into contact with 0.5 ml of a ~ 0.3 M solution of ~ orbitol; we homogenize the mixture. ~ 'experience is made at ambient temperature.
`~ We then have ~ 4 ml of a 0.145 M solution (NaCl, KCl).
~ e ball, placed ~ ur shaker ~ e, is act ~ energi ~ ue-lie for 4 hours.
~ a di ~ per ~ ion obtained e ~ opalescent; the diameter of - ~ spherules is approximately 2 microns.
In a 50 ml round flask, 425 mg are brought into contact of the product, general formula:
lOb3908 R _ (OCH2_CH ~ - OH
R being the slkyle radical of oleic alcohol and n ~ being a number equal to ~ 2, and 75 mg of an amine of the following formula:
R _ ~ OCH2- ~ H ~ -OCH2CHOH _CH2N ~
R being the radical ol ~ yl and n having a mean statistic value of 1, with 0.5 ml of a solution ~ 0.3 M of glucose, and we homogeneous nei ~ e the mixture. ~ 'e ~ experience e ~ t made ~ room temperature.
Cn then added ~ 4 ml of a 0.145 M solution (NaCl ~ KCl).
Ie ball, placed eur a ~ ecoueu ~ e, is agitated ~ energetic-lie for 4 hours ~.
~ a disper ~ ion obtained is op ~ queS the diameter of ~ ~ ph ~ -rules is ~ upérleur ~ 2 micron ~.
Ia di ~ peraion can 8tre subjected to ultra ~ ~ ons, the size of ~ ~ pherule ~ becoming alor ~ inf ~ lower than the mi ¢ ron.
In a 50 ml round flask, 300 mg of ~ phingomyelin ~ have mi ~ in contact with ~ ec 0.350 ml of a ~ olution 0.3M from asevid to ~ cor-bique, and homogé ~ éi ~ e the mixture. The experience was made room temperature.
2.650 ml of 0.145M solution is then added.
(NaCl, ~ Cl). ~ e ball, pl ~ c ~ ~ ur a ~ e ¢ oueu ~ e, e ~ t agitated ~ nergi-only for 4 hours ~.
Ia di ~ per ~ ion obtained e ~ t mileu ~ e; the diameter of ~
aph ~ rule ~ e ~ t en ~ iron 2 microns.
If 1 ~ desired, the di ~ per ~ ion can be filtered on column of gel "Sephadex G 50 coar ~ e" swelling ~ dan ~ a solution 0.145 M (NaCl, KCl).
- 18 _ E ~ IE 16 In a 50 ml round flask, 142 mg of the Na salt of the I ~ 2 (alkyl_suif) _N dodecyl-N (N ', N'_diethylaminoethyl) -asparagine 80nt dissolved in ~ 2 ml of a mixture of chloroform-methanol in the 2sl ratio ~ The solvent is evaporated ~ ide of a rotary evaporator tif, pui ~ we eliminate the ~ last traces of soil ~ nt by submitting the product for one hour ~ the reduced pressure given by a pump ~ vanes, 10 ml of a 3M solution of glucose are put in contact.
with lipid.
~ e balloon put on a shaker ~ e, is strongly acted ~
for 4 hours. ~ 'experiment was done ~ at room temperature ~ a size of ~ ~ pherule ~ e ~ t of about 1 micron. The dispersion is then flltr ~ e ~ ur column of gel "Sephadex G 50 coarse" swollen in a 0.145 ~ solution (NaCl, KCl).
Dan ~ a 50 ml flask, we say ~ out 80 mg of the product general ~ ule:
R ~ CH2-PH ~ OH
CH20H / n R ~ as the radical he ~ decyl and n being equal to 2.10 mg cholest ~ rol and 10 mg of diketyl phosphate in 2 ml of a mixture chloroform / methanol in the ratio 2/1.
5n evaporates the solvent with the idea of a rotary evaporator and on ~ eliminate the ~ last ~ re ~ trace ~ of soil ~ ant by pa ~ 3age ~ the pump . ~
pslette ~ for 1 hour.
10 ml of a 0.15 M solution of the salt are brought into contact sodium of pyroglutamic acid with the ~ lipid ~. ~ e balloon, mid ~
on a shake, stirred strongly for 2 hours ~ BU bsin-marie ~ 55C pUi3 while cooling progressively ~ until returning to ~ 18 room temperature.
~ a di ~ persion is ~ oumise auy ultrasound ~ during the hour a temperature maintained near 19 ambient temperature. Cn filter ~ during the di ~ per3ion on a column of gel "Sephadex G 50 coarse "swollen in distilled water. r ~ a di ~ persion obtained e ~ t fluid and clslre aprac not ~ age auY ultrasound; the diameter of the spherules is less than ~ 1 micron.
Dan ~ a 50 ml round flask, we mix 240 mg intimately of the product of formula gener ~ le:
~
R t OCH2-qH ~ OH
2 n R being the alkyl radical of ~ hydrogenated lanolin alcohols and n has an average statistical value of 3, and 60 mg of cholesterol rol.
The mixture obtained is brought into contact with 0.4 ml of a ~ 0.15 M solution of ~ el sodium pyroglytamic acid and homogeneous ~ se the m ~ diaper. ~ the experiment is made at 45C We add en ~ uite 4 6 ml of ~ a solution of sodlum chloride ~ 9 / oo.
~ e ball, placed ~ in u ~ bain-marie, is energetic agitated-ment ~ using a ~ ecoueu ~ e for 2 hours at 45C puia en cooling progressively ~ u ~ that ~ return to temperature roomy.
~ A dispersion obtained is fluid and laiteu3e; the diameter spherules is greater ~ one micron In a 50 ml round flask, we mix intimately 200 mg of the product of general formula:
~ 0 R
C ~ 2 ~ -.
R ~ both the radi ~ sl he ~ adecyle and n being ~ gal ~ 2, 25 mg of cholest ~ rol and 25 ~ g of dlcétyl-phonphate; we are in contact on mixture obtained with 0.3 ml of a tartaric aldehyde solution 10% and the mixture is homogenized. ~ 'eYperience is done ~ 55C.
Then added ~ uite 4.7 ml of ~ ne 0.145 M solution (NaCl ~ KCl).
Ie balloon, placed dan ~ a bain-mzrie, is acted ~ energetic-ment ~ using a ~ ecoueu ~ e for 2 hours ~ 55C pui ~ en cooling progressively ~ until ~ return to 1 ~ temperature ambient.
The di ~ per ~ ion obtained e ~ tg ~ lifi ~ e and a ~ pect slightly bluish, ~ 'spplication ~ imultan ~ e on the skin of oette di ~ persion of niosome ~ and an aqueous solution ~ e at the same final concentration in aldehydetartaric, allows to appreciate ~ deuY effects of ~ niosome ~
the ~ which ~, considerably reinforcing the developed coloration ~ e, markedly improve the resistance of this coloration to ~ washing ~
water and detergent ~.
It e ~ t of course that the ~ mode ~ of realization ~ ation below ~ u ~
deorit ~ are auounem ~ nt limiting and may give rise to any ~ desirable modifications ~, except for the framework of the invention.
. '.
-;
.
Claims (32)
X - Y
formule dans laquelle X représente un groupe hydrophile ionique ou non-ionique et Y représente un groupe lipophile, et d'autre part la phase aqueuse à encapsuler dans les sphérules, le rapport lipophile/hydrophile du lipide étant tel que ce dernier gonfle dans la phase aqueuse à encapsuler, pour former une phase lamellaire; que l'on agite pour assurer le mélange et obtenir une phase lamellaire; que l'on ajoute ensuite un liquide de dispersion en quantité supérieure à la quantité
de phase lamellaire obtenue et que l'on secoue énergiquement pendant un temps variant de 15 mn à 4 heures environ, 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, étant compris entre 0.1 environ et 3 environ, et le rapport pondéral de la quantité de phase de dispersion, que l'on ajoute à la quantité de phase lamellaire, que l'on disperse, étant compris entre 2 et 100 environ. 1. Method for obtaining a dispersion of spherules made up of organized molecular layers containing a aqueous phase to be encapsulated, characterized in that one brings into contact, on the one hand, at least one liquid lipid dispersible in water and having the general formula:
X - Y
formula in which X represents an ionic hydrophilic group or nonionic and Y represents a lipophilic group, and other the aqueous phase to be encapsulated in the spherules, the lipophilic / hydrophilic ratio of the lipid being such that the latter swells in the aqueous phase to be encapsulated, to form a lamellar phase; shake to ensure mixing and obtain a lamellar phase; which we then add a dispersion liquid in quantity greater than the quantity of lamellar phase obtained and shaken vigorously for a time varying from 15 minutes to approximately 4 hours, the weight ratio between the quantity of aqueous phase to encapsulate contact with lipids and quantity of lipids forming the lamellar phase, being between 0.1 about and about 3, and the weight ratio of the amount of dispersion phase, which is added to the quantity of phase lamellar, which is dispersed, being between 2 and 100 approximately.
par le fait que la phase aqueuse à encapsuler est une solution aqueuse de produit actif. 3. Method according to claim 1, characterized by the fact that the aqueous phase to be encapsulated is a solution aqueous active product.
par le fait que la phase de dispersion et la phase aqueuse à encapsuler sont isoosmotiques. 4. Method according to claim 1, characterized by the fact that the dispersion phase and the aqueous phase to be encapsulated are isoosmotic.
par le fait que la phase de dispersion est une solution aqueuse. 5. Method according to claim 1, characterized by the fact that the dispersion phase is a solution aqueous.
par le fait qu'il est mis en oeuvre à une température au moins égale à la température de fusion du lipide. 6. Process according to claim 1, characterized by the fact that it is implemented at a temperature at less equal to the melting temperature of the lipid.
par le fait que le (ou les) lipide (s) utilisé (s) comporte (nt) une chaîne lipophile comportant de 12 à 30 atomes de carbone. 8. Method according to claim 1, characterized by the fact that the lipid (s) used contains (nt) a lipophilic chain containing from 12 to 30 atoms of carbon.
par le fait que le (ou les) lipide (s) utilisé (s) sont choisis dans le groupe formé par les lipides comportant une chaîne oléique, lanolique, tétradécylique, hexadécylique, isostéarylique, laurique ou alcoylphényl. 9. Method according to claim 8, characterized by the fact that the lipid (s) used are chosen from the group formed by lipids comprising a oleic, lanolic, tetradecylic, hexadecylic chain, isostearyl, lauric or alkylphenyl.
par le fait que le groupement non-ionique est un ester de sorbitol polyoxyéthyléné. 11. Method according to claim 10, characterized by the fact that the nonionic group is an ester of polyoxyethylenated sorbitol.
par le fait que ledit groupement hydrophile est un composé
amphotère comportant deux chaînes lipophiles ou une association de deux ions organiques à longue chaîne de signes opposés. 12. Method according to one of claims 8 or 9, in which the hydrophilic group of the lipid forming the lamellar phase is an ionic group, characterized by the fact that said hydrophilic group is a compound amphoteric comprising two lipophilic chains or one association of two long chain organic ions opposite signs.
par le fait que l'on utilise, comme lipides formant la phase lamellaire, au moins un composé non-ionique pris dans le groupe formé par:
- les éthers de polyglycérol linéaires ou ramifiés de formules respectives:
et n étant un entier compris entre 1 et 6, R étant une chaîne aliphatique linéaire ou ramifiée, saturée ou insaturée, com-prenant de 12 à 30 atomes de carbone; les radicaux hydrocar-bonés des alcools de lanoline; les restes hydroxy-2-alkyle des .alpha.-diols à longue chaîne;
- les alcools gras polyoxyéthylénés;
- les esters de polyols oxyéthylénés ou non ;
- les glycolipides d'origine naturelle ou synthétique. 13. Method according to claim 1, characterized by the fact that we use, as lipids forming the phase lamellar, at least one nonionic compound taken from the group formed by:
- linear or branched polyglycerol ethers of formulas respective:
and n being an integer between 1 and 6, R being a chain aliphatic linear or branched, saturated or unsaturated, com-taking from 12 to 30 carbon atoms; hydrocarbon radicals lanolin alcohol sweeties; hydroxy-2-alkyl radicals long chain .alpha.-diols;
- polyoxyethylenated fatty alcohols;
- esters of polyols, oxyethylenated or not;
- glycolipids of natural or synthetic origin.
encapsuler, que les composés lipidiques sont des composés amphiphiles non-ioniques à chaîne liquide susceptibles d'être dispersés dans l'eau, que les sphérules ont un diamètre compris entre 100 et 50,000 .ANG. environ, que les composés lipidiques non-ioniques ont un rapport lipophile/hydrophile tel que le composé gonfle dans la phase aqueuse à encapsuler en formant une phase lamellaire. 15. Dispersion of spherules made up of layers organized molecules of lipid compounds, characterized by the fact that the spherules enclose an aqueous phase at encapsulate, that lipid compounds are compounds non-ionic liquid chain amphiphiles likely to be dispersed in water, that the spherules have a diameter between 100 and 50,000 .ANG. approximately, that the compounds non-ionic lipids have a lipophilic / hydrophilic ratio such that the compound swells in the aqueous phase to be encapsulated by forming a lamellar phase.
- les éthers de polyglycérol linéaires ou ramifiés de formules respectives et n étant un entier compris entre 1 et 6, R étant une chaîne aliphatique linéaire ou ramifiée, saturée ou insaturée, comprenant de 12 à 30 atomes de carbone; les radicaux hydro-carbonés des alcools de lanoline; les restes hydroxy-2-alkyle des .alpha.-diols à longue chaîne;
- les alcools gras polyoxyéthylénés;
- les esters de polyols oxyéthylénés ou non;
- les glycolipides d'origine naturelle ou synthétique. 18. Dispersion according to claim 15, characterized by the fact that non-ionic lipid compounds are taken in the group formed by:
- linear or branched polyglycerol ethers of Respective formulas and n being an integer between 1 and 6, R being a chain aliphatic linear or branched, saturated or unsaturated, comprising from 12 to 30 carbon atoms; hydro- radicals carbonated lanolin alcohols; hydroxy-2-alkyl radicals long chain .alpha.-diols;
- polyoxyethylenated fatty alcohols;
- esters of polyols, oxyethylenated or not;
- glycolipids of natural or synthetic origin.
un groupe lipophile, caractérisée par le fait que les sphérules ont un diamètre compris entre 1,000 .ANG. et 50,000 .ANG. environ, les composés lipidiques ayant un rapport lipophile/hydrophile tel que le composé gonfle dans la phase aqueuse à encapsuler en formant une phase lamellaire. 24. Dispersion of spherules made up of layers organized molecules enclosing an aqueous phase to be encapsulated, these layers being made up of at least one lipid compound of formula XY, X denoting an ionic hydrophilic group and Y
a lipophilic group, characterized in that the spherules have a diameter between 1,000 .ANG. and 50,000 .ANG. about, the lipid compounds having a lipophilic / hydrophilic ratio such that the compound swells in the aqueous phase to be encapsulated in forming a lamellar phase.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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FR7520456A FR2315991A1 (en) | 1975-06-30 | 1975-06-30 | METHOD OF MANUFACTURING AQUEOUS DISPERSIONS OF LIPID SPHERULES AND CORRESPONDING NEW COMPOSITIONS |
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Publication Number | Publication Date |
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CA1063908A true CA1063908A (en) | 1979-10-09 |
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ID=9157266
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA255,929A Expired CA1063908A (en) | 1975-06-30 | 1976-06-29 | Process for the production of dispersions of lipidic droplets in water and new compositions based on same |
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) | DE2661108C2 (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) |
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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 |
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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 |
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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 DE2661108A patent/DE2661108C2/en not_active Expired - Lifetime
- 1976-06-29 DE DE2660069A patent/DE2660069C2/de not_active Expired - Lifetime
- 1976-06-29 CA CA255,929A patent/CA1063908A/en not_active Expired
- 1976-06-29 GB GB27094/76A patent/GB1539625A/en not_active Expired
- 1976-06-29 DE DE2629100A patent/DE2629100C3/en not_active Expired
- 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
- 1976-06-30 NL NLAANVRAGE7607210,A patent/NL168715C/en not_active IP Right Cessation
- 1976-06-30 JP JP51076601A patent/JPS588287B2/en not_active Expired
- 1976-06-30 IT IT68608/76A patent/IT1062389B/en active
- 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 |
---|---|---|---|---|
US4456586A (en) * | 1980-10-24 | 1984-06-26 | L'oreal | Non-ionic surface-active agents derived from glucose, process for their preparation and compositions containing them |
Also Published As
Publication number | Publication date |
---|---|
IT1062389B (en) | 1984-10-10 |
BE843300A (en) | 1976-12-23 |
AU505843B2 (en) | 1979-12-06 |
CH616087A5 (en) | 1980-03-14 |
AU1539376A (en) | 1978-01-05 |
DE2660069C2 (en) | 1990-09-13 |
DE2629100C3 (en) | 1980-08-14 |
DE2661108C2 (en) | 1993-12-16 |
DK291376A (en) | 1976-12-31 |
JPS56108528A (en) | 1981-08-28 |
DE2629100A1 (en) | 1977-01-20 |
FR2315991B1 (en) | 1977-12-02 |
BR7604270A (en) | 1977-04-05 |
DK150967C (en) | 1988-02-15 |
JPS6156016B2 (en) | 1986-12-01 |
DE2629100B2 (en) | 1979-11-29 |
NL7607210A (en) | 1977-01-03 |
JPS526375A (en) | 1977-01-18 |
GB1539625A (en) | 1979-01-31 |
CH623236A5 (en) | 1981-05-29 |
NL168715C (en) | 1982-05-17 |
DK150967B (en) | 1987-10-05 |
AT361893B (en) | 1981-04-10 |
ATA470376A (en) | 1980-09-15 |
ES449312A1 (en) | 1977-08-16 |
JPS588287B2 (en) | 1983-02-15 |
FR2315991A1 (en) | 1977-01-28 |
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