JPS58205538A - マイクロカプセル及びその製造方法 - Google Patents
マイクロカプセル及びその製造方法Info
- Publication number
- JPS58205538A JPS58205538A JP58078856A JP7885683A JPS58205538A JP S58205538 A JPS58205538 A JP S58205538A JP 58078856 A JP58078856 A JP 58078856A JP 7885683 A JP7885683 A JP 7885683A JP S58205538 A JPS58205538 A JP S58205538A
- Authority
- JP
- Japan
- Prior art keywords
- microcapsules
- milk
- crosslinking agent
- crosslinking
- microcapsule
- 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.)
- Pending
Links
- 239000003094 microcapsule Substances 0.000 title claims abstract description 80
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000008267 milk Substances 0.000 claims abstract description 34
- 235000013336 milk Nutrition 0.000 claims abstract description 33
- 210000004080 milk Anatomy 0.000 claims abstract description 33
- 239000013543 active substance Substances 0.000 claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 3
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 33
- 238000003756 stirring Methods 0.000 claims description 17
- 239000003431 cross linking reagent Substances 0.000 claims description 15
- 238000004945 emulsification Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000004132 cross linking Methods 0.000 claims description 13
- 239000000843 powder Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 239000003995 emulsifying agent Substances 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 8
- 239000002775 capsule Substances 0.000 claims description 7
- -1 dicarboxylic acid halides Chemical class 0.000 claims description 7
- 239000000839 emulsion Substances 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 235000020183 skimmed milk Nutrition 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000003921 oil Substances 0.000 claims description 6
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 5
- 239000010419 fine particle Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000005119 centrifugation Methods 0.000 claims description 4
- 238000010908 decantation Methods 0.000 claims description 4
- 238000005192 partition Methods 0.000 claims description 4
- 239000011877 solvent mixture Substances 0.000 claims description 4
- 102000014171 Milk Proteins Human genes 0.000 claims description 3
- 108010011756 Milk Proteins Proteins 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000010775 animal oil Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 235000021239 milk protein Nutrition 0.000 claims description 3
- 239000008158 vegetable oil Substances 0.000 claims description 3
- 235000008939 whole milk Nutrition 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
- IRXBNHGNHKNOJI-UHFFFAOYSA-N butanedioyl dichloride Chemical compound ClC(=O)CCC(Cl)=O IRXBNHGNHKNOJI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- 238000004108 freeze drying Methods 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- 235000020603 homogenised milk Nutrition 0.000 claims description 2
- 235000008476 powdered milk Nutrition 0.000 claims description 2
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
- 241000908656 Vestiaria coccinea Species 0.000 claims 1
- 238000002679 ablation Methods 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
- 230000010933 acylation Effects 0.000 abstract description 2
- 238000005917 acylation reaction Methods 0.000 abstract description 2
- 102000004169 proteins and genes Human genes 0.000 abstract description 2
- 108090000623 proteins and genes Proteins 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- 235000008390 olive oil Nutrition 0.000 description 7
- 239000004006 olive oil Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 229920000136 polysorbate Polymers 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 229950008882 polysorbate Drugs 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 4
- 229960001214 clofibrate Drugs 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229960004025 sodium salicylate Drugs 0.000 description 3
- ZPXGNBIFHQKREO-UHFFFAOYSA-N 2-chloroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(Cl)=C1 ZPXGNBIFHQKREO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- XXEPPPIWZFICOJ-UHFFFAOYSA-N diethylpropion Chemical compound CCN(CC)C(C)C(=O)C1=CC=CC=C1 XXEPPPIWZFICOJ-UHFFFAOYSA-N 0.000 description 2
- 229960004890 diethylpropion Drugs 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000001000 micrograph Methods 0.000 description 2
- 238000000879 optical micrograph Methods 0.000 description 2
- 238000000399 optical microscopy Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
- 239000000592 Artificial Cell Substances 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- ZYZWOSIRFVIBRH-UHFFFAOYSA-N chloroform;cyclohexane Chemical compound ClC(Cl)Cl.C1CCCCC1 ZYZWOSIRFVIBRH-UHFFFAOYSA-N 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 235000020247 cow milk Nutrition 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 102000038379 digestive enzymes Human genes 0.000 description 1
- 108091007734 digestive enzymes Proteins 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 235000020122 reconstituted milk Nutrition 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- 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
- 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
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5052—Proteins, e.g. albumin
-
- 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
- A61K9/5005—Wall or coating material
- A61K9/5063—Compounds of unknown constitution, e.g. material from plants or animals
-
- 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
- A61K9/5089—Processes
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Botany (AREA)
- Zoology (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8207735 | 1982-05-04 | ||
| FR8207735A FR2526328A1 (fr) | 1982-05-04 | 1982-05-04 | Microcapsules a paroi obtenue par reticulation des proteines du lait, et leur procede de preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS58205538A true JPS58205538A (ja) | 1983-11-30 |
Family
ID=9273705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58078856A Pending JPS58205538A (ja) | 1982-05-04 | 1983-05-04 | マイクロカプセル及びその製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0093668B2 (enExample) |
| JP (1) | JPS58205538A (enExample) |
| AT (1) | ATE16152T1 (enExample) |
| DE (1) | DE3361057D1 (enExample) |
| FR (1) | FR2526328A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6133112A (ja) * | 1984-06-05 | 1986-02-17 | ユニヴエルシテ・パリ−シユド （パリ・オンズ） | 生物学的に劣化可能なマイクロカプセルとその製造方法 |
| JP2014051435A (ja) * | 2012-09-04 | 2014-03-20 | Kyushu Univ | 新規イオン液体およびその用途 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU614537B2 (en) * | 1987-09-09 | 1991-09-05 | Richard B. Bankert | Use of milk fat globules as carriers for drugs and as microflotation devices in immunoassays and cell molecular fractionation |
| US6022501A (en) | 1996-08-15 | 2000-02-08 | American Cyanamid Company | pH-sensitive microcapsules |
| ES2395553B1 (es) * | 2011-06-22 | 2013-12-26 | Consejo Superior De Investigaciones Científicas (Csic) | Procedimiento de obtención de micro-, submicro- y nanocápsulas basado en proteínas del suero de la leche. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55109443A (en) * | 1978-12-19 | 1980-08-22 | Mars Inc | Microocapsulizing process |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3137631A (en) * | 1959-12-01 | 1964-06-16 | Faberge Inc | Encapsulation in natural products |
| DE2453852A1 (de) * | 1973-11-16 | 1975-05-28 | Ciba Geigy Ag | Verfahren zur einkapselung von mit wasser nicht mischbaren substanzen |
| IL58965A (en) * | 1978-12-19 | 1982-08-31 | Mars Inc | Production of microcapsules |
-
1982
- 1982-05-04 FR FR8207735A patent/FR2526328A1/fr active Granted
-
1983
- 1983-04-29 DE DE8383400862T patent/DE3361057D1/de not_active Expired
- 1983-04-29 EP EP83400862A patent/EP0093668B2/fr not_active Expired - Lifetime
- 1983-04-29 AT AT83400862T patent/ATE16152T1/de not_active IP Right Cessation
- 1983-05-04 JP JP58078856A patent/JPS58205538A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55109443A (en) * | 1978-12-19 | 1980-08-22 | Mars Inc | Microocapsulizing process |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6133112A (ja) * | 1984-06-05 | 1986-02-17 | ユニヴエルシテ・パリ−シユド （パリ・オンズ） | 生物学的に劣化可能なマイクロカプセルとその製造方法 |
| JP2014051435A (ja) * | 2012-09-04 | 2014-03-20 | Kyushu Univ | 新規イオン液体およびその用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0093668B2 (fr) | 1990-06-20 |
| EP0093668A1 (fr) | 1983-11-09 |
| EP0093668B1 (fr) | 1985-10-23 |
| ATE16152T1 (de) | 1985-11-15 |
| DE3361057D1 (en) | 1985-11-28 |
| FR2526328B1 (enExample) | 1984-10-19 |
| FR2526328A1 (fr) | 1983-11-10 |
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