CA2325554A1 - Microcapsules a action retardee - Google Patents
Microcapsules a action retardee Download PDFInfo
- Publication number
- CA2325554A1 CA2325554A1 CA002325554A CA2325554A CA2325554A1 CA 2325554 A1 CA2325554 A1 CA 2325554A1 CA 002325554 A CA002325554 A CA 002325554A CA 2325554 A CA2325554 A CA 2325554A CA 2325554 A1 CA2325554 A1 CA 2325554A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- solution
- microcapsules
- chitosan
- group
- 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
- 239000003094 microcapsule Substances 0.000 title claims abstract description 49
- 230000003111 delayed effect Effects 0.000 title description 7
- 239000000243 solution Substances 0.000 claims abstract description 34
- 229920001661 Chitosan Polymers 0.000 claims abstract description 31
- -1 calcium cations Chemical class 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 229920000447 polyanionic polymer Polymers 0.000 claims abstract description 7
- 230000007062 hydrolysis Effects 0.000 claims abstract description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 6
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 3
- 239000011575 calcium Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229920001282 polysaccharide Polymers 0.000 claims description 11
- 239000005017 polysaccharide Substances 0.000 claims description 11
- 150000004804 polysaccharides Chemical class 0.000 claims description 11
- 229940072056 alginate Drugs 0.000 claims description 10
- 229920000615 alginic acid Polymers 0.000 claims description 10
- 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 claims description 9
- 235000010443 alginic acid Nutrition 0.000 claims description 9
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 239000001205 polyphosphate Substances 0.000 claims description 6
- 235000011176 polyphosphates Nutrition 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 229920000388 Polyphosphate Polymers 0.000 claims description 5
- 229920002307 Dextran Polymers 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 claims description 4
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 claims description 4
- 229940015043 glyoxal Drugs 0.000 claims description 4
- 235000019698 starch Nutrition 0.000 claims description 4
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 claims description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 4
- 108010039918 Polylysine Proteins 0.000 claims description 3
- 229920000656 polylysine Polymers 0.000 claims description 3
- DSLBDPPHINVUID-REOHCLBHSA-N (2s)-2-aminobutanediamide Chemical compound NC(=O)[C@@H](N)CC(N)=O DSLBDPPHINVUID-REOHCLBHSA-N 0.000 claims description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 claims description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- JDTUPLBMGDDPJS-UHFFFAOYSA-N 2-methoxy-2-phenylethanol Chemical compound COC(CO)C1=CC=CC=C1 JDTUPLBMGDDPJS-UHFFFAOYSA-N 0.000 claims description 2
- 229920001817 Agar Polymers 0.000 claims description 2
- 239000004971 Cross linker Substances 0.000 claims description 2
- 229920000858 Cyclodextrin Polymers 0.000 claims description 2
- AEMOLEFTQBMNLQ-BZINKQHNSA-N D-Guluronic Acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@@H](O)[C@H]1O AEMOLEFTQBMNLQ-BZINKQHNSA-N 0.000 claims description 2
- 108010010803 Gelatin Proteins 0.000 claims description 2
- 241000206672 Gelidium Species 0.000 claims description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 2
- 229920001612 Hydroxyethyl starch Polymers 0.000 claims description 2
- 229920001202 Inulin Polymers 0.000 claims description 2
- 229920000805 Polyaspartic acid Polymers 0.000 claims description 2
- 108010020346 Polyglutamic Acid Proteins 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 claims description 2
- 235000010419 agar Nutrition 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 239000003899 bactericide agent Substances 0.000 claims description 2
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N beta-D-galactopyranuronic acid Natural products OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 235000010418 carrageenan Nutrition 0.000 claims description 2
- 239000000679 carrageenan Substances 0.000 claims description 2
- 229920001525 carrageenan Polymers 0.000 claims description 2
- 229940113118 carrageenan Drugs 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 229920003086 cellulose ether Polymers 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 229940097362 cyclodextrins Drugs 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 239000008273 gelatin Substances 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 claims description 2
- 229940050526 hydroxyethylstarch Drugs 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 claims description 2
- 229940029339 inulin Drugs 0.000 claims description 2
- 239000001630 malic acid Substances 0.000 claims description 2
- 235000011090 malic acid Nutrition 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 239000001814 pectin Substances 0.000 claims description 2
- 229920001277 pectin Polymers 0.000 claims description 2
- 235000010987 pectin Nutrition 0.000 claims description 2
- YVOFTMXWTWHRBH-UHFFFAOYSA-N pentanedioyl dichloride Chemical compound ClC(=O)CCCC(Cl)=O YVOFTMXWTWHRBH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
- 229920001308 poly(aminoacid) Polymers 0.000 claims description 2
- 108010064470 polyaspartate Proteins 0.000 claims description 2
- 229920002643 polyglutamic acid Polymers 0.000 claims description 2
- 235000019830 sodium polyphosphate Nutrition 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 2
- 229920001221 xylan Polymers 0.000 claims description 2
- 150000004823 xylans Chemical class 0.000 claims description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 claims description 2
- 239000002775 capsule Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 235000010413 sodium alginate Nutrition 0.000 description 3
- 239000000661 sodium alginate Substances 0.000 description 3
- 229940005550 sodium alginate Drugs 0.000 description 3
- 108010088751 Albumins Proteins 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 235000011148 calcium chloride Nutrition 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000011859 microparticle Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- FLEAADSSUQORCN-WBQOVJPJSA-N N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide Chemical compound CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO.CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O FLEAADSSUQORCN-WBQOVJPJSA-N 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000008384 inner phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- 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
- A61K8/73—Polysaccharides
- A61K8/736—Chitin; Chitosan; Derivatives thereof
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Birds (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Preparation (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Abstract
L'invention concerne un procédé de production de microcapsules. Ce procédé consiste a) à ajouter, en une opération, des gouttelettes d'une solution aqueuse (1) contenant au moins un polyanion soluble dans l'eau, dans une solution aqueuse (2) qui contient 0,1 à 5 % en poids de cations de calcium; et 0,1 à 5 % en poids de chitosane hydrolysé ayant un poids moléculaire moyen compris entre 2.200 et 40.000 g/mol, cette substance pouvant être obtenue par hydrolyse partielle d'un chitosane ayant un poids moléculaire moyen de plus de 50.000 g/mol dans une solution aqueuse contenant 0,1 à 4 N HCl à une température comprise entre 50 et 95 ·C pendant un temps compris entre 0,5 et 8 heures, le rapport du poids de la solution contenant le HCl par rapport au poids de chitosane courant dans le commerce est compris entre 1 et 50 et le produit de normalité de la solution HCl et la durée d'hydrolyse est compris entre 0,1 et 7 heure. Une fois la solution (1) ajoutée, ce procédé consiste b) à laisser les microcapsules ainsi obtenues dans la solution (2) pendant 15 à 360 minutes, notamment pendant 60 à 180 minutes.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813010.4 | 1998-03-25 | ||
| DE1998113010 DE19813010A1 (de) | 1998-03-25 | 1998-03-25 | Mikrokapseln mit verzögertem Release |
| PCT/EP1999/001625 WO1999048479A1 (fr) | 1998-03-25 | 1999-03-12 | Microcapsules a liberation retardee |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2325554A1 true CA2325554A1 (fr) | 1999-09-30 |
Family
ID=7862189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002325554A Abandoned CA2325554A1 (fr) | 1998-03-25 | 1999-03-12 | Microcapsules a action retardee |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1063970A1 (fr) |
| JP (1) | JP2002507472A (fr) |
| AU (1) | AU736941B2 (fr) |
| CA (1) | CA2325554A1 (fr) |
| DE (1) | DE19813010A1 (fr) |
| WO (1) | WO1999048479A1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8067020B2 (en) | 2001-06-21 | 2011-11-29 | Genetech, Inc. | Sustained release formulation |
| CN102960599A (zh) * | 2012-11-19 | 2013-03-13 | 陕西科技大学 | 一种含益生元的双歧杆菌微胶囊的制备方法 |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6458387B1 (en) | 1999-10-18 | 2002-10-01 | Epic Therapeutics, Inc. | Sustained release microspheres |
| DE19962350A1 (de) * | 1999-12-23 | 2001-06-28 | Henkel Kgaa | Gefärbte Chitosan-Kapseln |
| DE19962348A1 (de) * | 1999-12-23 | 2001-07-05 | Henkel Kgaa | Pigmentierte Chitosan-Kapseln |
| EP1167618A1 (fr) * | 2000-06-20 | 2002-01-02 | Primacare S.A. | Agent auxiliaire pour textiles |
| EP1243319A1 (fr) * | 2001-03-22 | 2002-09-25 | Primacare S.L., c/o Cognis Iberica S.L. | Microcapsules (XI) |
| EP1243324B1 (fr) * | 2001-03-22 | 2005-03-02 | Primacare S.L., c/o Cognis Iberica S.L. | Microcapsules (XII) |
| US6723359B2 (en) * | 2001-10-18 | 2004-04-20 | Firmenich Sa | Spray-dried compositions and method for their preparation |
| DE10164137B4 (de) * | 2001-12-30 | 2016-04-28 | Henkel Ag & Co. Kgaa | Wasch-, Reinigungs- und/oder Pflegemittel-Formulierung enthaltender Formkörper mit erhöhter Lagerstabilität sowie Verfahren zu seiner Herstellung |
| AU2003230320A1 (en) * | 2002-05-09 | 2003-11-11 | Peptron Co., Ltd | Sustained release formulation of protein and preparation method thereof |
| EP1837074A1 (fr) * | 2006-03-20 | 2007-09-26 | Cognis IP Management GmbH | Procédé de préparation de microcapsules à dureté contrôlée |
| WO2008037576A1 (fr) * | 2006-09-29 | 2008-04-03 | Unilever Plc | Procédé de production de composés constitués de particules contenant de l'amidon, enrobées, intégrées ou encapsulées dans au moins un biopolymère |
| WO2008037578A1 (fr) * | 2006-09-29 | 2008-04-03 | Unilever Plc | Composés, qui sont des particules contenant de l'amidon revêtues, intégrées ou encapsulées dans au moins un biopolymère dans un arrangement multicouche |
| WO2008157514A2 (fr) * | 2007-06-14 | 2008-12-24 | Genesegues, Inc. | Polymères biocompatibles traités par ion métallique utiles pour des nanoparticules |
| CN111700877A (zh) | 2014-09-03 | 2020-09-25 | 吉倪塞思公司 | 治疗性纳米粒子和相关的组合物、方法和系统 |
| WO2016108234A1 (fr) * | 2014-12-30 | 2016-07-07 | Yissum Research Develoment Company Of The Hebrew University Of Jerusalem Ltd. | Capsules à cœur liquide comprenant un alginate non réticulé |
| US10385296B2 (en) | 2017-03-16 | 2019-08-20 | The Procter & Gamble Company | Methods for making encapsulate-containing product compositions |
| US10611988B2 (en) | 2017-03-16 | 2020-04-07 | The Procter & Gamble Company | Methods for making encapsulate-containing product compositions |
| US10385297B2 (en) | 2017-03-16 | 2019-08-20 | The Procter & Gamble Company | Methods for making encapsulate-containing product compositions |
| CN107712543B (zh) * | 2017-09-20 | 2021-04-16 | 徐宝军 | 一种抗絮凝姜黄素微胶囊、制备方法及其应用 |
| JP2023543578A (ja) | 2020-10-16 | 2023-10-17 | ザ プロクター アンド ギャンブル カンパニー | 少なくとも２つの封入体集団を有する消費者製品組成物 |
| US12398348B2 (en) | 2020-10-16 | 2025-08-26 | The Procter & Gamble Company | Consumer product compositions comprising a population of encapsulates |
| US12486478B2 (en) | 2020-10-16 | 2025-12-02 | The Procter & Gamble Company | Consumer products comprising delivery particles with high core:wall ratios |
| CN119280103B (zh) * | 2024-10-16 | 2025-09-02 | 北京青颜博识健康管理有限公司 | 一种含有胶原蛋白的微胶囊乳液及其制备方法 |
| CN121136213B (zh) * | 2025-11-19 | 2026-02-10 | 武汉理工大学 | 一种氯盐控释型沥青自愈合胶囊及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5974984A (ja) * | 1982-10-21 | 1984-04-27 | Sumitomo Chem Co Ltd | 固定化酵素もしくは固定化微生物の製造方法 |
| JP2511612B2 (ja) * | 1992-02-28 | 1996-07-03 | 株式会社紀文フードケミファ | 徐放性組成物 |
-
1998
- 1998-03-25 DE DE1998113010 patent/DE19813010A1/de not_active Withdrawn
-
1999
- 1999-03-12 JP JP2000537529A patent/JP2002507472A/ja active Pending
- 1999-03-12 WO PCT/EP1999/001625 patent/WO1999048479A1/fr not_active Ceased
- 1999-03-12 CA CA002325554A patent/CA2325554A1/fr not_active Abandoned
- 1999-03-12 AU AU28365/99A patent/AU736941B2/en not_active Ceased
- 1999-03-12 EP EP99908958A patent/EP1063970A1/fr not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8067020B2 (en) | 2001-06-21 | 2011-11-29 | Genetech, Inc. | Sustained release formulation |
| CN102960599A (zh) * | 2012-11-19 | 2013-03-13 | 陕西科技大学 | 一种含益生元的双歧杆菌微胶囊的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2836599A (en) | 1999-10-18 |
| WO1999048479A1 (fr) | 1999-09-30 |
| DE19813010A1 (de) | 1999-10-14 |
| EP1063970A1 (fr) | 2001-01-03 |
| JP2002507472A (ja) | 2002-03-12 |
| AU736941B2 (en) | 2001-08-09 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |