CA1071935A - Method of producing microcapsules with coacervated oil-and-fat as the wall material - Google Patents
Method of producing microcapsules with coacervated oil-and-fat as the wall materialInfo
- Publication number
- CA1071935A CA1071935A CA259,234A CA259234A CA1071935A CA 1071935 A CA1071935 A CA 1071935A CA 259234 A CA259234 A CA 259234A CA 1071935 A CA1071935 A CA 1071935A
- Authority
- CA
- Canada
- Prior art keywords
- oil
- core material
- fat
- hydrogenated
- temperature
- 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
- 238000000034 method Methods 0.000 title claims abstract description 74
- 239000000463 material Substances 0.000 title claims description 24
- 239000003094 microcapsule Substances 0.000 title abstract description 8
- 239000011162 core material Substances 0.000 claims abstract description 69
- 239000003960 organic solvent Substances 0.000 claims abstract description 24
- 238000001816 cooling Methods 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 239000006185 dispersion Substances 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 14
- 238000005354 coacervation Methods 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 13
- 239000003242 anti bacterial agent Substances 0.000 claims description 11
- 238000002844 melting Methods 0.000 claims description 11
- 230000008018 melting Effects 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 11
- 229940088710 antibiotic agent Drugs 0.000 claims description 10
- 238000004090 dissolution Methods 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- -1 glycerin ester Chemical class 0.000 claims description 9
- 102000004190 Enzymes Human genes 0.000 claims description 8
- 108090000790 Enzymes Proteins 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
- 239000003921 oil Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 claims description 6
- 229930182555 Penicillin Natural products 0.000 claims description 6
- 239000003905 agrochemical Substances 0.000 claims description 6
- 239000008173 hydrogenated soybean oil Substances 0.000 claims description 6
- 235000019198 oils Nutrition 0.000 claims description 6
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 6
- 235000015278 beef Nutrition 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 244000005700 microbiome Species 0.000 claims description 5
- 239000003760 tallow Substances 0.000 claims description 5
- 229940088594 vitamin Drugs 0.000 claims description 5
- 229930003231 vitamin Natural products 0.000 claims description 5
- 235000013343 vitamin Nutrition 0.000 claims description 5
- 239000011782 vitamin Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 4
- 239000012051 hydrophobic carrier Substances 0.000 claims description 4
- 229960004592 isopropanol Drugs 0.000 claims description 4
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 4
- 229940041603 vitamin k 3 Drugs 0.000 claims description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004098 Tetracycline Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 230000000202 analgesic effect Effects 0.000 claims description 3
- 239000003674 animal food additive Substances 0.000 claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 235000010323 ascorbic acid Nutrition 0.000 claims description 3
- 239000011668 ascorbic acid Substances 0.000 claims description 3
- 229960005070 ascorbic acid Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 235000013305 food Nutrition 0.000 claims description 3
- 235000013373 food additive Nutrition 0.000 claims description 3
- 239000002778 food additive Substances 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 claims description 3
- 229960004172 pyridoxine hydrochloride Drugs 0.000 claims description 3
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 claims description 3
- 239000011764 pyridoxine hydrochloride Substances 0.000 claims description 3
- 235000019364 tetracycline Nutrition 0.000 claims description 3
- 150000003522 tetracyclines Chemical class 0.000 claims description 3
- 229930186147 Cephalosporin Natural products 0.000 claims description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 2
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 claims description 2
- 235000019482 Palm oil Nutrition 0.000 claims description 2
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 2
- 229920006243 acrylic copolymer Polymers 0.000 claims description 2
- 230000001754 anti-pyretic effect Effects 0.000 claims description 2
- 239000003904 antiprotozoal agent Substances 0.000 claims description 2
- 239000002221 antipyretic Substances 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 229940124587 cephalosporin Drugs 0.000 claims description 2
- 150000001780 cephalosporins Chemical class 0.000 claims description 2
- 235000021323 fish oil Nutrition 0.000 claims description 2
- 235000019152 folic acid Nutrition 0.000 claims description 2
- 239000011724 folic acid Substances 0.000 claims description 2
- 229960000304 folic acid Drugs 0.000 claims description 2
- 125000005456 glyceride group Chemical group 0.000 claims description 2
- 239000010514 hydrogenated cottonseed oil Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 229930182817 methionine Natural products 0.000 claims description 2
- 239000002540 palm oil Substances 0.000 claims description 2
- 150000002960 penicillins Chemical class 0.000 claims description 2
- 239000003910 polypeptide antibiotic agent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229940040944 tetracyclines Drugs 0.000 claims description 2
- 150000003544 thiamines Chemical class 0.000 claims description 2
- 235000012711 vitamin K3 Nutrition 0.000 claims description 2
- 239000011652 vitamin K3 Substances 0.000 claims description 2
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 2
- 239000010698 whale oil Substances 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 238000001035 drying Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 35
- 239000003925 fat Substances 0.000 description 28
- BLORRZQTHNGFTI-ZZMNMWMASA-L calcium-L-ascorbate Chemical compound [Ca+2].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] BLORRZQTHNGFTI-ZZMNMWMASA-L 0.000 description 22
- 235000010376 calcium ascorbate Nutrition 0.000 description 21
- 229940047036 calcium ascorbate Drugs 0.000 description 21
- 239000011692 calcium ascorbate Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 17
- 235000010378 sodium ascorbate Nutrition 0.000 description 12
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 12
- 229960005055 sodium ascorbate Drugs 0.000 description 12
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 10
- 241000235400 Phycomyces Species 0.000 description 8
- 238000005538 encapsulation Methods 0.000 description 8
- 239000003981 vehicle Substances 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 239000004367 Lipase Substances 0.000 description 7
- 102000004882 Lipase Human genes 0.000 description 7
- 108090001060 Lipase Proteins 0.000 description 7
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 7
- 235000014121 butter Nutrition 0.000 description 7
- 235000019421 lipase Nutrition 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- 235000001465 calcium Nutrition 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 229940088598 enzyme Drugs 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
- 244000299461 Theobroma cacao Species 0.000 description 4
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 4
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
- 235000001046 cacaotero Nutrition 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
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- 235000019197 fats Nutrition 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229940049954 penicillin Drugs 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
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- ORVLUIMCZUPAPB-LBTQIPEASA-M sodium (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide dioxido(oxo)phosphanium phosphenic acid Chemical compound [Na+].O[P+]([O-])=O.O[P+]([O-])=O.O[P+]([O-])=O.O[P+]([O-])=O.O[P+]([O-])=O.[O-][P+]([O-])=O.CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)c4c(O)cccc4[C@@]3(C)O)C(=O)[C@]2(O)C(O)=C(C(N)=O)C1=O.CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)c4c(O)cccc4[C@@]3(C)O)C(=O)[C@]2(O)C(O)=C(C(N)=O)C1=O.CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)c4c(O)cccc4[C@@]3(C)O)C(=O)[C@]2(O)C(O)=C(C(N)=O)C1=O.CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)c4c(O)cccc4[C@@]3(C)O)C(=O)[C@]2(O)C(O)=C(C(N)=O)C1=O.CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)c4c(O)cccc4[C@@]3(C)O)C(=O)[C@]2(O)C(O)=C(C(N)=O)C1=O ORVLUIMCZUPAPB-LBTQIPEASA-M 0.000 description 1
- NGIVTUVVBWOTNT-UHFFFAOYSA-N sodium;(4-aminophenyl)sulfonyl-(4,6-dimethylpyrimidin-2-yl)azanide Chemical compound [Na+].CC1=CC(C)=NC([N-]S(=O)(=O)C=2C=CC(N)=CC=2)=N1 NGIVTUVVBWOTNT-UHFFFAOYSA-N 0.000 description 1
- IZJAOWYNDLDRKM-UHFFFAOYSA-N sodium;(4-aminophenyl)sulfonyl-(6-methoxypyrimidin-4-yl)azanide Chemical compound [Na+].C1=NC(OC)=CC([N-]S(=O)(=O)C=2C=CC(N)=CC=2)=N1 IZJAOWYNDLDRKM-UHFFFAOYSA-N 0.000 description 1
- WXUQBKOBXREBBX-UHFFFAOYSA-N sodium;(4-aminophenyl)sulfonyl-quinoxalin-2-ylazanide Chemical compound [Na+].C1=CC(N)=CC=C1S(=O)(=O)[N-]C1=CN=C(C=CC=C2)C2=N1 WXUQBKOBXREBBX-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000019372 spiramycin Nutrition 0.000 description 1
- 229960001294 spiramycin Drugs 0.000 description 1
- 229930191512 spiramycin Natural products 0.000 description 1
- 229950006796 spiramycin ii Drugs 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960000973 sulfadimethoxine Drugs 0.000 description 1
- ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 description 1
- 229960000703 sulfadimethoxine sodium Drugs 0.000 description 1
- 229960002135 sulfadimidine Drugs 0.000 description 1
- ASWVTGNCAZCNNR-UHFFFAOYSA-N sulfamethazine Chemical compound CC1=CC(C)=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ASWVTGNCAZCNNR-UHFFFAOYSA-N 0.000 description 1
- 229940049287 sulfamethazine sodium Drugs 0.000 description 1
- 229960003097 sulfaquinoxaline Drugs 0.000 description 1
- 229960003264 sulfaquinoxaline sodium Drugs 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 229960004989 tetracycline hydrochloride Drugs 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 239000011747 thiamine hydrochloride Substances 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 229960000344 thiamine hydrochloride Drugs 0.000 description 1
- 235000019190 thiamine hydrochloride Nutrition 0.000 description 1
- 239000011748 thiamine mononitrate Substances 0.000 description 1
- 229960004860 thiamine mononitrate Drugs 0.000 description 1
- SRTDKHGZQCTGBY-RVDKCFQWSA-N thiopeptin Chemical compound N1C2C(N=3)=CSC=3C(C(C)OC(=O)C=3N=C4C(O)C(NC(C(C)C)C(=O)NC(C)C(=O)NC(=C)C(=O)NC(C)C(=O)N5)C=CC4=C(C(C)O)C=3)NC(=S)C(N=3)=CSC=3C(C(C)(O)C(C)O)NC(=O)C(N=3)CSC=3C(=C/C)\NC(=O)C(C(C)O)NC(=O)C(N=3)=CSC=3C25CCC1C1=NC(C(N)=O)=CS1 SRTDKHGZQCTGBY-RVDKCFQWSA-N 0.000 description 1
- 108010030742 thiopeptin Proteins 0.000 description 1
- 229940022036 threonate Drugs 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 229960005041 troleandomycin Drugs 0.000 description 1
- LQCLVBQBTUVCEQ-QTFUVMRISA-N troleandomycin Chemical compound O1[C@@H](C)[C@H](OC(C)=O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](OC(C)=O)[C@@H](C)C(=O)[C@@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)OC(C)=O)[C@H]1C LQCLVBQBTUVCEQ-QTFUVMRISA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 229960001322 trypsin Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UCRLQOPRDMGYOA-DFTDUNEMSA-L zinc;(4r)-4-[[(2s)-2-[[(4r)-2-[(1s,2s)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2s,3s)-1-[[(3s,6r,9s,12r,15s,18r,21s)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2s)-butan-2-yl]-6-(carbox Chemical compound [Zn+2].C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC([O-])=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2NC=NC=2)C(=O)N[C@H](CC([O-])=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 UCRLQOPRDMGYOA-DFTDUNEMSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
- C05G5/00—Fertilisers characterised by their form
- C05G5/30—Layered or coated, e.g. dust-preventing coatings
- C05G5/35—Capsules, e.g. core-shell
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
- A01N25/28—Microcapsules or nanocapsules
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K40/00—Shaping or working-up of animal feeding-stuffs
- A23K40/30—Shaping or working-up of animal feeding-stuffs by encapsulating; by coating
-
- 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
- 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
-
- 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
- B01J13/10—Complex coacervation, i.e. interaction of oppositely charged particles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S426/00—Food or edible material: processes, compositions, and products
- Y10S426/805—Pet food for dog, cat, bird, or fish
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2989—Microcapsule with solid core [includes liposome]
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Public Health (AREA)
- Toxicology (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Agronomy & Crop Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Plant Pathology (AREA)
- Epidemiology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Molecular Biology (AREA)
- Environmental Sciences (AREA)
- Dispersion Chemistry (AREA)
- Biophysics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Preparation (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1261077A JPS5323872A (en) | 1976-08-17 | 1977-02-07 | Preparation of microcapsule |
| NL7701554A NL7701554A (nl) | 1976-08-17 | 1977-02-14 | Werkwijze voor het verkrijgen van microcapsules. |
| DK65877A DK65877A (da) | 1976-08-17 | 1977-02-16 | Fremgangsmaade til fremstilling af mikrokapsler |
| DE19772706705 DE2706705A1 (de) | 1976-08-17 | 1977-02-17 | Verfahren zur herstellung von mikrokapseln |
| FR7704624A FR2361935A1 (fr) | 1976-08-17 | 1977-02-17 | Procede pour fabriquer des microcapsules |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50100363A JPS5231981A (en) | 1975-08-18 | 1975-08-18 | Microcapsule preparation method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1071935A true CA1071935A (en) | 1980-02-19 |
Family
ID=14271979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA259,234A Expired CA1071935A (en) | 1975-08-18 | 1976-08-17 | Method of producing microcapsules with coacervated oil-and-fat as the wall material |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4102806A (show.php) |
| JP (1) | JPS5231981A (show.php) |
| CA (1) | CA1071935A (show.php) |
| GB (1) | GB1528419A (show.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2406517A (en) * | 2003-09-30 | 2005-04-06 | Alpharma Ltd | Controlled release micropellets of tetracyclines |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4464434A (en) * | 1978-03-13 | 1984-08-07 | Celanese Corporation | Microencapsulated alkaloidal material and method of producing same |
| JPS5580394U (show.php) * | 1978-11-24 | 1980-06-03 | ||
| CH637297A5 (fr) * | 1978-12-05 | 1983-07-29 | Nestle Sa | Microbille comprenant un microorganisme et son procede de fabrication. |
| JPS5646807A (en) * | 1979-09-27 | 1981-04-28 | Japan Atom Energy Res Inst | Production of composition of complex gradually releasing physiologically active substance |
| JPS56140915A (en) * | 1980-04-07 | 1981-11-04 | Yamanouchi Pharmaceut Co Ltd | Pharmaceutical preparation for solid drug |
| IT1148784B (it) * | 1980-04-09 | 1986-12-03 | Eurand Spa | Procedimento per la preparazione di microcapsule in un veicolo liquido |
| JPS6029682B2 (ja) * | 1980-07-11 | 1985-07-12 | 山之内製薬株式会社 | 苦味のない製剤用組成物およびその製造法 |
| WO1983000799A1 (en) * | 1981-08-31 | 1983-03-17 | Sierra Chem | Slow release pesticide and composite granules and method for making the same |
| US5082351A (en) * | 1981-09-16 | 1992-01-21 | Manchester R & D Partnership | Encapsulated liquid crystal material, apparatus and method |
| US5089904A (en) * | 1981-09-16 | 1992-02-18 | Fergason James L | Encapsulated liquid crystal material, apparatus and method |
| US4884873A (en) * | 1981-09-16 | 1989-12-05 | Manchester R & D Partnership | Encapsulated liquid crystal material, apparatus and method having interconnected capsules |
| FR2515035A1 (fr) * | 1981-10-26 | 1983-04-29 | Rhone Poulenc Sante | Nouvelle forme galenique solide pour administration par voie orale et son procede de fabrication |
| US4428951A (en) | 1982-04-22 | 1984-01-31 | Fujisawa Pharmaceutical Co., Ltd. | Long acting pharmaceutical composition |
| IT1159074B (it) * | 1982-06-24 | 1987-02-25 | Stoppani Luigi Spa | Composto di addizione fra menadione e tiamina a reciproca stabilizzazione |
| US4525339A (en) * | 1982-10-15 | 1985-06-25 | Hoffmann-La Roche Inc. | Enteric coated oral dosage form |
| US4597960A (en) * | 1983-04-19 | 1986-07-01 | Cohen Edgar C | Microencapsulated astringent hemostatic agents and methods of use |
| GB2141023B (en) * | 1983-06-06 | 1986-09-03 | Robins Co Inc A H | Delayed release formulations |
| CA1237671A (en) * | 1983-08-01 | 1988-06-07 | Michael W. Fountain | Enhancement of pharmaceutical activity |
| US4749575A (en) * | 1983-10-03 | 1988-06-07 | Bio-Dar Ltd. | Microencapsulated medicament in sweet matrix |
| US4713245A (en) * | 1984-06-04 | 1987-12-15 | Mitsui Toatsu Chemicals, Incorporated | Granule containing physiologically-active substance, method for preparing same and use thereof |
| EP0169398B1 (de) * | 1984-07-24 | 1990-08-29 | R.P. Scherer GmbH | Oxytetracyclin-HC1-Weichgelatinekapseln und Verfahren zu ihrer Herstellung |
| JPS61174940A (ja) * | 1985-01-29 | 1986-08-06 | Oogawara Kakoki Kk | ワックス類コーテイング単核状マイクロカプセルおよびその製造方法 |
| US4818521A (en) * | 1985-04-18 | 1989-04-04 | Sunstar Kabushiki Kaisha | Emulsion cosmetic stably containing vitamin C |
| JPS6277320A (ja) * | 1985-09-28 | 1987-04-09 | Kyowa Hakko Kogyo Co Ltd | Ｌ−アスコルビン酸製剤およびその製造法 |
| JPS63151353A (ja) * | 1986-12-15 | 1988-06-23 | Oogawara Kakoki Kk | ワツクスコ−テイングマイクロカプセルの製造方法 |
| SE463674B (sv) * | 1987-01-15 | 1991-01-07 | Lejus Medical Ab | Foerfarande foer behandling i fluidiserad baedd av amfotaera aminosyror och amfotaera derivat av aminosyror |
| US4948586A (en) * | 1987-11-02 | 1990-08-14 | Lim Technology Laboratories, Inc. | Microencapsulated insecticidal pathogens |
| US4844896A (en) * | 1987-11-02 | 1989-07-04 | Lim Technology Laboratories, Inc. | Microencapsulated insecticidal pathogens |
| DE69025480T2 (de) * | 1989-01-25 | 1996-07-11 | Pfizer | Kalorienarmer Fettersatz |
| NZ232238A (en) * | 1989-02-16 | 1991-07-26 | Wrigley W M Jun Co | Food products containing porous polymeric beads impregnated with a vitamin |
| US5098725A (en) * | 1989-06-30 | 1992-03-24 | Bio-Dar, Ltd. | Heat stabilized flavoring agents coated with hydrogenated castor oil |
| US5089271A (en) * | 1989-09-18 | 1992-02-18 | Smithkline Beecham Corporation | Stabilized antibiotic compositions for animal feeding |
| JPH03164140A (ja) * | 1989-11-21 | 1991-07-16 | Sanyo Kokusaku Pulp Co Ltd | 養魚用飼料組成物 |
| GB9107628D0 (en) * | 1991-04-10 | 1991-05-29 | Moonbrook Limited | Preparation of diagnostic agents |
| GB9221329D0 (en) | 1992-10-10 | 1992-11-25 | Delta Biotechnology Ltd | Preparation of further diagnostic agents |
| WO1994009636A1 (en) * | 1992-10-26 | 1994-05-11 | Mars, Inc. | Competitive organism preservation |
| DE69331001D1 (de) * | 1993-05-28 | 2001-11-29 | Ascor Chimici Srl | Tierärztliche Zusammensetzung für die Behandlung und/oder Verhütung von Infektionen und Krankheiten |
| US5589194A (en) * | 1993-09-20 | 1996-12-31 | Minnesota Mining And Manufacturing Company | Method of encapsulation and microcapsules produced thereby |
| US6818229B1 (en) | 1993-09-20 | 2004-11-16 | Kos Pharmaceuticals, Inc. | Intermediate release nicotinic acid compositions for treating hyperlipidemia |
| US6746691B2 (en) | 1993-09-20 | 2004-06-08 | Kos Pharmaceuticals, Inc. | Intermediate release nicotinic acid compositions for treating hyperlipidemia having unique biopharmaceutical characteristics |
| US6129930A (en) * | 1993-09-20 | 2000-10-10 | Bova; David J. | Methods and sustained release nicotinic acid compositions for treating hyperlipidemia at night |
| US20080045573A1 (en) * | 1993-09-20 | 2008-02-21 | Bova David J | Methods and Sustained Release Nicotinic Acid Compositions for Treating Hyperlipidemia |
| US6080428A (en) * | 1993-09-20 | 2000-06-27 | Bova; David J. | Nicotinic acid compositions for treating hyperlipidemia and related methods therefor |
| US6676967B1 (en) | 1993-09-20 | 2004-01-13 | Kos Pharmaceuticals, Inc. | Methods for reducing flushing in individuals being treated with nicotinic acid for hyperlipidemia |
| EP0772395A1 (en) * | 1994-07-22 | 1997-05-14 | Novartis AG | Spherical microparticles having an inner wax coating deposited around biologically active compounds |
| GB9423419D0 (en) * | 1994-11-19 | 1995-01-11 | Andaris Ltd | Preparation of hollow microcapsules |
| BE1009257A3 (nl) * | 1995-03-21 | 1997-01-07 | Universiteit Gent Lab Voor Far | Farmaceutische matrix. |
| JP5038552B2 (ja) * | 1995-10-17 | 2012-10-03 | オバン・エナジー・リミテッド | 不溶性薬物の送達 |
| US7255877B2 (en) * | 1996-08-22 | 2007-08-14 | Jagotec Ag | Fenofibrate microparticles |
| US6465016B2 (en) | 1996-08-22 | 2002-10-15 | Research Triangle Pharmaceuticals | Cyclosporiine particles |
| US6017310A (en) * | 1996-09-07 | 2000-01-25 | Andaris Limited | Use of hollow microcapsules |
| US6068600A (en) * | 1996-12-06 | 2000-05-30 | Quadrant Healthcare (Uk) Limited | Use of hollow microcapsules |
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| US5891476A (en) * | 1997-12-22 | 1999-04-06 | Reo; Joe P. | Tastemasked pharmaceutical system |
| DE69908304T2 (de) * | 1998-02-11 | 2004-02-19 | Rtp Pharma Corp. | Ungesättigte fettsäure und steroide enthaltende kombinationspräparate zur behandlung von entzündungen |
| US6979456B1 (en) | 1998-04-01 | 2005-12-27 | Jagotec Ag | Anticancer compositions |
| AU764001B2 (en) | 1998-05-29 | 2003-08-07 | Skyepharma Canada Inc. | Thermoprotected microparticle compositions and process for terminal steam sterilization thereof |
| AU759641B2 (en) | 1998-08-19 | 2003-04-17 | Skyepharma Canada Inc. | Injectable aqueous dispersions of propofol |
| HUP0105089A3 (en) | 1998-11-20 | 2002-09-30 | Skyepharma Canada Inc | Compositions containing the active ingredient in form dispersible phospholipid stabilized microparticles |
| ATE296091T1 (de) * | 1999-09-21 | 2005-06-15 | Skyepharma Canada Inc | Oberflächenmodifizierte teilchenförmige zusammensetzungen biologisch aktiver stoffe |
| US6251478B1 (en) * | 1999-12-22 | 2001-06-26 | Balchem Corporation | Sensitive substance encapsulation |
| ES2469642T3 (es) | 2000-04-20 | 2014-06-18 | Jagotec Ag | Procedimiento mejorado para partículas de fármaco insoluble en agua |
| WO2002017883A2 (en) | 2000-08-31 | 2002-03-07 | Rtp Pharma Inc. | Milled particles |
| US8586094B2 (en) | 2000-09-20 | 2013-11-19 | Jagotec Ag | Coated tablets |
| NZ527408A (en) * | 2001-02-22 | 2005-04-29 | Skyepharma Canada Inc | Hydroxymethylglutarylcoenzyme A (HMG CoA) reductase inhibitor (or a statin) and a fibrate in a single effective oral dosage form to treat dyslipidaemia and dyslipoproteinaemia |
| US6773733B2 (en) * | 2001-03-26 | 2004-08-10 | Loders Croklaan Usa Llc | Structured particulate systems |
| US20030232091A1 (en) * | 2002-06-17 | 2003-12-18 | Adi Shefer | Stabilized retinol for cosmetic dermatological, and pharmaceutical compositions, and use thereof |
| US20050003070A1 (en) * | 2003-07-03 | 2005-01-06 | Foster David V. | Shelf stable vitamin C in oatmeal products |
| DE102004002732B4 (de) * | 2004-01-20 | 2006-11-16 | Dr. Paul Lohmann Gmbh Kg | Herstellungsverfahren für mikroverkapselte Eisen-II-Sulfat enthaltende Partikel sowie Eisen-II-Sulfat enthaltende Partikel mit Mikroverkapselungen |
| GB0600913D0 (en) | 2006-01-17 | 2006-02-22 | Syngenta Ltd | Improvements in or relating to organic compounds |
| CN101466273A (zh) * | 2006-06-16 | 2009-06-24 | 古木林科有限公司 | 包含疏水酶制剂的口香糖 |
| US9186640B2 (en) * | 2007-08-28 | 2015-11-17 | Pepsico, Inc. | Delivery and controlled release of encapsulated lipophilic nutrients |
| US20100272859A1 (en) * | 2007-08-28 | 2010-10-28 | Pepsico, Inc. | Delivery and controlled release of encapsulated water-insoluble flavorants |
| US20100229282A1 (en) * | 2009-03-11 | 2010-09-16 | Ansell Limited | Powder-Free Anti-Blocking Coated Glove |
| US9149567B2 (en) * | 2009-03-11 | 2015-10-06 | Ansell Limited | Powder-free antimicrobial coated glove |
| FR3030227B1 (fr) * | 2014-12-17 | 2018-01-26 | L'oreal | Emulsion stabilisees par des particules composites amphiphiles |
| CN105503475B (zh) * | 2016-01-01 | 2019-03-29 | 江苏新汉菱生物工程股份有限公司 | 一种微囊包裹的氨基酸液体矿物肥 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2805977A (en) * | 1955-01-04 | 1957-09-10 | Smith Kline French Lab | Sustained release pharmaceutical preparation |
| US2875130A (en) * | 1956-11-20 | 1959-02-24 | Smith Kline French Lab | Method of preparing sustained release particles and the product of the method |
| US2967177A (en) * | 1958-03-31 | 1961-01-03 | Bristol Myers Co | Process of antibiotic purification |
| US3415758A (en) * | 1960-03-09 | 1968-12-10 | Ncr Co | Process of forming minute capsules en masse |
| NL263733A (show.php) * | 1960-04-19 | 1900-01-01 | ||
| US3196018A (en) * | 1960-08-08 | 1965-07-20 | Galler William | Coated menadione bisulfite adduct |
| US3584114A (en) * | 1968-05-22 | 1971-06-08 | Hoffmann La Roche | Free-flowing powders |
| US3541204A (en) * | 1968-12-02 | 1970-11-17 | Ian Ramsay Sibbald | Encapsulated biologically active materials for feeding to ruminants and process for the production thereof |
| GB1413186A (en) * | 1973-06-27 | 1975-11-12 | Toyo Jozo Kk | Process for encapsulation of medicaments |
-
1975
- 1975-08-18 JP JP50100363A patent/JPS5231981A/ja active Granted
-
1976
- 1976-08-17 CA CA259,234A patent/CA1071935A/en not_active Expired
- 1976-08-17 US US05/715,192 patent/US4102806A/en not_active Expired - Lifetime
- 1976-08-17 GB GB34193/76A patent/GB1528419A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2406517A (en) * | 2003-09-30 | 2005-04-06 | Alpharma Ltd | Controlled release micropellets of tetracyclines |
| GB2420708A (en) * | 2003-09-30 | 2006-06-07 | Alpharma Ltd | Tetracycline controlled release pharmaceutical composition |
| GB2406517B (en) * | 2003-09-30 | 2006-07-12 | Alpharma Ltd | Minocycline controlled release pharmaceutical composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS537149B2 (show.php) | 1978-03-15 |
| JPS5231981A (en) | 1977-03-10 |
| GB1528419A (en) | 1978-10-11 |
| US4102806A (en) | 1978-07-25 |
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