CA2699802A1 - Aqueous-core lipid nanocapsules for encapsulating hydrophilic and/or lipophilic molecules - Google Patents
Aqueous-core lipid nanocapsules for encapsulating hydrophilic and/or lipophilic molecules Download PDFInfo
- Publication number
- CA2699802A1 CA2699802A1 CA2699802A CA2699802A CA2699802A1 CA 2699802 A1 CA2699802 A1 CA 2699802A1 CA 2699802 A CA2699802 A CA 2699802A CA 2699802 A CA2699802 A CA 2699802A CA 2699802 A1 CA2699802 A1 CA 2699802A1
- Authority
- CA
- Canada
- Prior art keywords
- oil
- surfactant
- water
- volatile oil
- aqueous
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000002088 nanocapsule Substances 0.000 title claims abstract description 85
- 150000002632 lipids Chemical class 0.000 title description 9
- 150000002433 hydrophilic molecules Chemical class 0.000 title description 8
- 150000002634 lipophilic molecules Chemical class 0.000 title description 6
- 239000012071 phase Substances 0.000 claims abstract description 68
- 239000004094 surface-active agent Substances 0.000 claims abstract description 68
- 239000000203 mixture Substances 0.000 claims abstract description 61
- 239000002245 particle Substances 0.000 claims abstract description 43
- 239000000126 substance Substances 0.000 claims abstract description 39
- 239000008346 aqueous phase Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 90
- 238000000034 method Methods 0.000 claims description 76
- 239000003921 oil Substances 0.000 claims description 69
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 55
- 239000000178 monomer Substances 0.000 claims description 51
- 238000005538 encapsulation Methods 0.000 claims description 35
- 239000000341 volatile oil Substances 0.000 claims description 29
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 27
- 239000000346 nonvolatile oil Substances 0.000 claims description 27
- 239000000839 emulsion Substances 0.000 claims description 25
- 239000007762 w/o emulsion Substances 0.000 claims description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 14
- 230000001351 cycling effect Effects 0.000 claims description 13
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 12
- -1 polyoxyethylene moiety Polymers 0.000 claims description 10
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 10
- 229920002396 Polyurea Polymers 0.000 claims description 8
- 239000005662 Paraffin oil Substances 0.000 claims description 7
- 239000002736 nonionic surfactant Substances 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 229940059904 light mineral oil Drugs 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- 239000011258 core-shell material Substances 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 2
- 229920000136 polysorbate Polymers 0.000 claims description 2
- 229950008882 polysorbate Drugs 0.000 claims description 2
- 239000007908 nanoemulsion Substances 0.000 description 40
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 38
- 229920000642 polymer Polymers 0.000 description 26
- 230000008569 process Effects 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 19
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 17
- 229960000907 methylthioninium chloride Drugs 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 15
- 239000004530 micro-emulsion Substances 0.000 description 13
- 239000002480 mineral oil Substances 0.000 description 12
- 235000010446 mineral oil Nutrition 0.000 description 12
- 238000010790 dilution Methods 0.000 description 11
- 239000012895 dilution Substances 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 10
- 238000006068 polycondensation reaction Methods 0.000 description 10
- 241000894007 species Species 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000004627 transmission electron microscopy Methods 0.000 description 9
- 229940079593 drug Drugs 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000000604 cryogenic transmission electron microscopy Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 230000006641 stabilisation Effects 0.000 description 7
- 238000011105 stabilization Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
- 238000004220 aggregation Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000012696 Interfacial polycondensation Methods 0.000 description 4
- 238000012695 Interfacial polymerization Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 229960004679 doxorubicin Drugs 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- COQLPRJCUIATTQ-UHFFFAOYSA-N Uranyl acetate Chemical compound O.O.O=[U]=O.CC(O)=O.CC(O)=O COQLPRJCUIATTQ-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000001427 coherent effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000265 homogenisation Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- 229920006254 polymer film Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000011002 quantification Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 229920001059 synthetic polymer Polymers 0.000 description 3
- 239000004907 Macro-emulsion Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 230000003013 cytotoxicity Effects 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001493 electron microscopy Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 239000002077 nanosphere Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002773 nucleotide Substances 0.000 description 2
- 125000003729 nucleotide group Chemical group 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- JVKUCNQGESRUCL-UHFFFAOYSA-N 2-Hydroxyethyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCCO JVKUCNQGESRUCL-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- SHBUUTHKGIVMJT-UHFFFAOYSA-N Hydroxystearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OO SHBUUTHKGIVMJT-UHFFFAOYSA-N 0.000 description 1
- 229910025794 LaB6 Inorganic materials 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 229920001304 Solutol HS 15 Polymers 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- QYZIDAZFCCVJNS-UHFFFAOYSA-M [6-(dimethylamino)thioxanthen-3-ylidene]-dimethylazanium;chloride Chemical compound [Cl-].C1=CC(=[N+](C)C)C=C2SC3=CC(N(C)C)=CC=C3C=C21 QYZIDAZFCCVJNS-UHFFFAOYSA-M 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 239000012888 bovine serum Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000007771 core particle Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- CPBQJMYROZQQJC-UHFFFAOYSA-N helium neon Chemical compound [He].[Ne] CPBQJMYROZQQJC-UHFFFAOYSA-N 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229940072106 hydroxystearate Drugs 0.000 description 1
- 238000005184 irreversible process Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000010420 shell particle Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
Classifications
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/513—Organic macromolecular compounds; Dendrimers
- A61K9/5146—Organic macromolecular compounds; Dendrimers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyamines, polyanhydrides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P10/00—Shaping or working of foodstuffs characterised by the products
- A23P10/30—Encapsulation of particles, e.g. foodstuff additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P10/00—Shaping or working of foodstuffs characterised by the products
- A23P10/30—Encapsulation of particles, e.g. foodstuff additives
- A23P10/35—Encapsulation of particles, e.g. foodstuff additives with oils, lipids, monoglycerides or diglycerides
-
- 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
- A61K8/11—Encapsulated compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/87—Polyurethanes
-
- 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
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
- B01J13/16—Interfacial polymerisation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/413—Nanosized, i.e. having sizes below 100 nm
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Physics & Mathematics (AREA)
- Nanotechnology (AREA)
- Optics & Photonics (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Colloid Chemistry (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07291109.2 | 2007-09-18 | ||
| EP07291109A EP2039352A1 (en) | 2007-09-18 | 2007-09-18 | Aqueous-core lipid nanocapsules for encapsulating hydrophilic and/or lipophilic molecules |
| PCT/EP2008/062435 WO2009037310A2 (en) | 2007-09-18 | 2008-09-18 | Aqueous-core lipid nanocapsules for encapsulating hydrophilic and/or lipophilic molecules |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2699802A1 true CA2699802A1 (en) | 2009-03-26 |
Family
ID=38785137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2699802A Abandoned CA2699802A1 (en) | 2007-09-18 | 2008-09-18 | Aqueous-core lipid nanocapsules for encapsulating hydrophilic and/or lipophilic molecules |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9522121B2 (cg-RX-API-DMAC7.html) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US9393315B2 (en) | 2011-06-08 | 2016-07-19 | Nitto Denko Corporation | Compounds for targeting drug delivery and enhancing siRNA activity |
| FR2950253B1 (fr) * | 2009-09-24 | 2011-09-23 | Ethypharm Sa | Nanocapsules lipidiques, procede de preparation et utilisation comme medicament |
| JP4834775B2 (ja) | 2010-03-04 | 2011-12-14 | 株式会社 資生堂 | 日焼け止め用組成物 |
| US10196637B2 (en) | 2011-06-08 | 2019-02-05 | Nitto Denko Corporation | Retinoid-lipid drug carrier |
| CN102441355B (zh) * | 2011-08-29 | 2013-10-30 | 华南理工大学 | 一种嵌段离聚体水相自组装纳米胶囊及其制备方法 |
| US20130251855A1 (en) * | 2012-03-21 | 2013-09-26 | Pepsico, Inc. | Aqueous product comprising oil-containing microcapsules and method for the manufacture thereof |
| WO2014003370A1 (ko) | 2012-06-25 | 2014-01-03 | 주식회사 엘지화학 | 폴리알킬렌 카보네이트 성형품 제조용 에멀젼 조성물 및 이를 사용하여 제조된 수지 성형품 |
| EP3135276B1 (en) | 2013-03-12 | 2019-05-08 | Cephalon, Inc. | Nanoparticulate and macroparticulate formulations |
| JP6377913B2 (ja) * | 2013-04-16 | 2018-08-22 | 積水化学工業株式会社 | マイクロカプセルの製造方法及びマイクロカプセル |
| TWI482782B (zh) * | 2013-05-31 | 2015-05-01 | Univ Nat Chiao Tung | 架接抗體之雙乳化核殼奈米結構 |
| CN103271406B (zh) * | 2013-06-08 | 2014-07-16 | 吉林大学 | 一种复合型两亲性芯材微胶囊冲剂及其制备方法 |
| FR3008900B1 (fr) * | 2013-07-25 | 2018-03-30 | Centre Nat Rech Scient | Nanoparticules lipidiques multicompartimentees |
| GB2520370B (en) | 2014-05-01 | 2016-09-14 | Frito Lay Trading Co Gmbh | Snack food seasoning |
| GB2520371B (en) * | 2014-05-01 | 2016-09-14 | Frito Lay Trading Co Gmbh | Snack food seasoning |
| WO2015181346A1 (en) * | 2014-05-30 | 2015-12-03 | AbbVie Deutschland GmbH & Co. KG | Highly drug-loaded poly(alkyl 2-cyanoacrylate) nanocapsules |
| JP6572598B2 (ja) * | 2015-04-02 | 2019-09-11 | 日本製鉄株式会社 | ナノ粒子の粒径測定方法 |
| WO2016164773A1 (en) * | 2015-04-09 | 2016-10-13 | Saudi Arabian Oil Company | Encapsulated nanocompositions for increasing hydrocarbon recovery |
| KR102692648B1 (ko) * | 2015-12-04 | 2024-08-06 | (주)아모레퍼시픽 | 변성 단백질 수상 분산입자를 포함하는 화장료 조성물 및 이의 제조방법 |
| CN106942771A (zh) * | 2017-04-06 | 2017-07-14 | 贝因美婴童食品股份有限公司 | 一种用于制备营养品的胶囊 |
| EP3797279A4 (en) * | 2018-07-11 | 2022-08-03 | The University of Hong Kong | Automatic microfluidic system for continuous and quantitive collection of droplets |
| FR3092833B1 (fr) * | 2019-02-18 | 2021-07-16 | Commissariat Energie Atomique | Procede de fabrication de nanoparticules hybrides metal/polymere a faible distribution de tailles par polymerisation en mini-emulsion |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB9414318D0 (en) * | 1994-07-15 | 1994-09-07 | Dowelanco Ltd | Preparation of aqueous emulsions |
| FR2725369B1 (fr) * | 1994-10-07 | 1997-01-03 | Oreal | Composition cosmetique ou dermatologique constituee d'une emulsion huile dans eau a base de globules huileux pourvus d'un enrobage cristal liquide lamellaire |
| DE19630176C2 (de) * | 1996-07-26 | 2000-11-02 | Babor Gmbh & Co Dr | Kosmetische und pharmazeutische Mittel, gebildet durch eine nach dem Phaseninversionsverfahren erzeugte W/O/W-Emulsion |
| JP2002520120A (ja) * | 1998-07-17 | 2002-07-09 | スカイファーマ インコーポレーテッド | 封入物質の制御放出のための生分解性組成物 |
| FR2805761B1 (fr) * | 2000-03-02 | 2002-08-30 | Mainelab | Nanocapsules lipidiques, procede de preparation et utilisation comme medicament |
| GB0009735D0 (en) * | 2000-04-19 | 2000-06-07 | Zeneca Ltd | Formulation |
| US20020155084A1 (en) * | 2000-06-02 | 2002-10-24 | The Regents Of The University Of The Michigan | Nanoemulsion formulations |
| WO2003086609A1 (en) * | 2002-04-05 | 2003-10-23 | University Of Florida | Oil-filled nanocapsules from microemulsions utilizing cross-linkable surfactants |
| US20040115254A1 (en) * | 2002-09-06 | 2004-06-17 | Genteric, Inc. | Microcapsules and methods of use |
| WO2005007080A2 (en) * | 2003-05-20 | 2005-01-27 | Johns Hopkins University | Methods and compositions for delivery of catecholic butanes for treatment of tumors |
| CN1460468A (zh) * | 2003-06-05 | 2003-12-10 | 浙江大学 | 改进的包埋蛋白类药物和疫苗的高分子微球的制备方法 |
| WO2005003543A1 (en) * | 2003-07-02 | 2005-01-13 | Tiax Llc | Free piston stirling engine control |
| CN100402109C (zh) * | 2003-08-01 | 2008-07-16 | 卡拉科科学公司 | 经颅电刺激设备和方法 |
| JP4747534B2 (ja) * | 2003-09-01 | 2011-08-17 | 大正製薬株式会社 | Ｗ／ｏ／ｗ型複合エマルション |
| DE10351644A1 (de) * | 2003-11-05 | 2005-06-09 | Bayer Technology Services Gmbh | Verfahren zur Herstellung von lagerstabilen multiplen Emulsionen |
| AU2003292763A1 (en) * | 2003-12-24 | 2005-07-14 | Amato Pharmaceutical Products, Ltd. | Process for producing microsphere and apparatus for producing the same |
| JP2005263647A (ja) * | 2004-03-16 | 2005-09-29 | Konica Minolta Medical & Graphic Inc | エマルション粒子含有造影剤 |
| US20110135734A1 (en) * | 2004-04-20 | 2011-06-09 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Method For the Preparation of Nanoparticles From Nanoemulsions |
| US8211415B2 (en) * | 2004-10-13 | 2012-07-03 | L'oreal | Easily removable waterproof cosmetic care and/or makeup composition comprising at least one latex or pseudolatex |
| US8029709B2 (en) * | 2004-10-29 | 2011-10-04 | The University Of Cincinnati | Liquid core capsules and methods of synthesis thereof through interfacial polymerization |
| ATE477792T1 (de) * | 2005-11-22 | 2010-09-15 | Nestec Sa | Öl-in-wasser-emulsion und ihre verwendung zur abgabe einer funktionalität |
| EP2026771B1 (en) * | 2006-01-23 | 2009-10-21 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Microspheres comprising nanocapsules containing a lipophilic drug |
| CN100999656A (zh) * | 2006-12-22 | 2007-07-18 | 华南理工大学 | 潜热型纳米流体传热工质及其制备方法 |
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- 2007-09-18 EP EP07291109A patent/EP2039352A1/en not_active Ceased
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2008
- 2008-09-18 CN CN201410049011.9A patent/CN103800304A/zh active Pending
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- 2008-09-18 JP JP2010525348A patent/JP5989964B2/ja not_active Expired - Fee Related
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- 2008-09-18 EP EP08804375A patent/EP2187877A2/en not_active Withdrawn
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Also Published As
| Publication number | Publication date |
|---|---|
| CN103800304A (zh) | 2014-05-21 |
| JP5989964B2 (ja) | 2016-09-07 |
| WO2009037310A2 (en) | 2009-03-26 |
| JP2010539221A (ja) | 2010-12-16 |
| US20100297247A1 (en) | 2010-11-25 |
| CN101842088A (zh) | 2010-09-22 |
| EP2039352A1 (en) | 2009-03-25 |
| WO2009037310A3 (en) | 2010-02-18 |
| KR20100074196A (ko) | 2010-07-01 |
| US9522121B2 (en) | 2016-12-20 |
| JP2014221802A (ja) | 2014-11-27 |
| EP2187877A2 (en) | 2010-05-26 |
| CN101842088B (zh) | 2014-03-12 |
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