CA1177847A - Method for preparing small sized benzoyl peroxide crystals - Google Patents
Method for preparing small sized benzoyl peroxide crystalsInfo
- Publication number
- CA1177847A CA1177847A CA000411660A CA411660A CA1177847A CA 1177847 A CA1177847 A CA 1177847A CA 000411660 A CA000411660 A CA 000411660A CA 411660 A CA411660 A CA 411660A CA 1177847 A CA1177847 A CA 1177847A
- Authority
- CA
- Canada
- Prior art keywords
- benzoyl peroxide
- solution
- separation
- dispersant
- recovered
- 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
- 239000004342 Benzoyl peroxide Substances 0.000 title claims abstract description 99
- 235000019400 benzoyl peroxide Nutrition 0.000 title claims abstract description 99
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 title claims abstract description 98
- 238000000034 method Methods 0.000 title claims abstract description 85
- 239000013078 crystal Substances 0.000 title claims abstract description 42
- 239000000243 solution Substances 0.000 claims abstract description 60
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 28
- 239000002270 dispersing agent Substances 0.000 claims abstract description 27
- 239000002244 precipitate Substances 0.000 claims abstract description 23
- 230000001737 promoting effect Effects 0.000 claims abstract description 21
- 239000002537 cosmetic Substances 0.000 claims abstract description 11
- -1 aliphatic ethers Chemical class 0.000 claims abstract description 10
- 150000002170 ethers Chemical class 0.000 claims abstract description 7
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003945 anionic surfactant Substances 0.000 claims abstract description 3
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 229960003328 benzoyl peroxide Drugs 0.000 claims description 93
- 238000000926 separation method Methods 0.000 claims description 29
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 10
- 238000013019 agitation Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 4
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 4
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 4
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 4
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 4
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 claims description 4
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 4
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 229920003086 cellulose ether Polymers 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- QAHVPNVAAKXGRZ-UHFFFAOYSA-N 8-methyl-2-(2-phenoxyethoxy)nonan-2-ol Chemical compound CC(C)CCCCCC(C)(O)OCCOC1=CC=CC=C1 QAHVPNVAAKXGRZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 2
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000391 magnesium silicate Substances 0.000 claims description 2
- 229910052919 magnesium silicate Inorganic materials 0.000 claims description 2
- 235000019792 magnesium silicate Nutrition 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 2
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 claims description 2
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 claims description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 2
- 239000001488 sodium phosphate Substances 0.000 claims description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 2
- UMEWSJNRBXKWKZ-UHFFFAOYSA-M sodium;1,4-dioxo-1,4-dipentoxybutane-2-sulfonate Chemical compound [Na+].CCCCCOC(=O)CC(S([O-])(=O)=O)C(=O)OCCCCC UMEWSJNRBXKWKZ-UHFFFAOYSA-M 0.000 claims description 2
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 claims 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 claims 1
- 150000008051 alkyl sulfates Chemical class 0.000 claims 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims 1
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims 1
- 229940067741 sodium octyl sulfate Drugs 0.000 claims 1
- WFRKJMRGXGWHBM-UHFFFAOYSA-M sodium;octyl sulfate Chemical compound [Na+].CCCCCCCCOS([O-])(=O)=O WFRKJMRGXGWHBM-UHFFFAOYSA-M 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- BBECRFZLZMRJLF-UHFFFAOYSA-N tetradecyl sulfate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCCCCCCCCOS(O)(=O)=O BBECRFZLZMRJLF-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 12
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 3
- 238000010348 incorporation Methods 0.000 abstract description 2
- 229910010272 inorganic material Inorganic materials 0.000 abstract description 2
- 239000011147 inorganic material Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 150000002978 peroxides Chemical class 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfate Natural products OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- 230000005226 mechanical processes and functions Effects 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 238000009527 percussion Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/32—Peroxy compounds the —O—O— group being bound between two >C=O groups
- C07C409/34—Peroxy compounds the —O—O— group being bound between two >C=O groups both belonging to carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/303,229 US4401835A (en) | 1981-09-17 | 1981-09-17 | Method for preparing small sized benzoyl peroxide crystals |
| US303,229 | 1981-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1177847A true CA1177847A (en) | 1984-11-13 |
Family
ID=23171105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000411660A Expired CA1177847A (en) | 1981-09-17 | 1982-09-17 | Method for preparing small sized benzoyl peroxide crystals |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4401835A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0075442B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5869863A (cg-RX-API-DMAC7.html) |
| AU (1) | AU550984B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1177847A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3264919D1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA826743B (cg-RX-API-DMAC7.html) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5110495A (en) * | 1984-01-03 | 1992-05-05 | Abco Industries, Ltd. | Organic peroxide dispersions |
| US4917816A (en) * | 1984-01-03 | 1990-04-17 | Abco Industries, Inc. | Stabilized peroxide compositions and process for producing same |
| US4923900A (en) * | 1985-01-24 | 1990-05-08 | Board Of Regents, The University Of Texas System | Therapeutic compositions containing benzoyl peroxide |
| DE69009974T2 (de) * | 1990-02-07 | 1994-12-22 | Akzo Nobel Nv | Agglomeration von festen Peroxiden. |
| US5470884A (en) * | 1994-05-19 | 1995-11-28 | Procter & Gamble | Anti-acne compositions |
| ES2143538T3 (es) * | 1994-06-17 | 2000-05-16 | Procter & Gamble | Composiciones blanqueantes. |
| US5880079A (en) * | 1994-06-17 | 1999-03-09 | The Procter & Gamble Company | Bleaching compositions |
| WO2008057411A1 (en) * | 2006-11-02 | 2008-05-15 | Stiefel Laboratories, Inc. | Kits containing benzoyl peroxide pads and another acne-treating composition, and formulations and methods of use therefor |
| WO2008057423A1 (en) * | 2006-11-02 | 2008-05-15 | Stiefel Laboratories, Inc. | Kits containing benzoyl peroxide pads and a barrier repair composition, and formulations and methods of use therefor |
| JP5034505B2 (ja) * | 2007-01-12 | 2012-09-26 | 日油株式会社 | 有機過酸化物組成物の製造方法 |
| AU2009255679B2 (en) | 2008-06-05 | 2015-04-09 | Dow Pharmaceutical Sciences, Inc. | Topical pharmaceutical formulations containing a low concentration of benzoyl peroxide in suspension in water and a water-miscible organic solvent |
| MX2012004211A (es) | 2009-10-07 | 2012-10-03 | Tagra Biotechnologies Ltd | Microcapsulas que comprenden peroxido de benzoilo y composiciones topicas que las comprenden. |
| US9744150B2 (en) * | 2009-10-21 | 2017-08-29 | Dow Pharmaceutical Sciences Inc. | Suspension containing micronized benzoyl peroxide |
| US8697130B1 (en) | 2010-05-25 | 2014-04-15 | Essential Ingredients, Inc. | Non-irritating benzoyl peroxide |
| US20140199397A1 (en) * | 2011-06-10 | 2014-07-17 | Daniel Levin | Benzoyl Peroxide Microparticle Process |
| CN113292471A (zh) * | 2021-06-11 | 2021-08-24 | 山东阳谷华泰化工股份有限公司 | 一种微米级粉末状过氧化二苯甲酰的制备方法 |
| CN115160203A (zh) * | 2022-07-15 | 2022-10-11 | 睦化(上海)流体工程有限公司 | 一种过氧苯甲酰产品连续复配方法及装置 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE934592C (de) * | 1936-07-03 | 1955-10-27 | Hoechst Ag | Verfahren zur Herstellung von Acylsuperoxyden |
| US2453070A (en) * | 1944-08-23 | 1948-11-02 | Buffalo Electrochemical Compan | Organic peroxide composition |
| US3324040A (en) * | 1965-09-17 | 1967-06-06 | Wallace & Tiernan Inc | Homogeneous benzoyl peroxide paste |
| US3535422A (en) * | 1968-03-11 | 1970-10-20 | Stiefel Laboratories | Stable benzoyl peroxide composition |
| US3591540A (en) * | 1969-11-12 | 1971-07-06 | Arras M Praskach | Stable,free flowing peroxide compositions |
| GB1428796A (en) * | 1973-11-19 | 1976-03-17 | Nippon Oils & Fats Co Ltd | Method for purifying dicumyl peroxide |
-
1981
- 1981-09-17 US US06/303,229 patent/US4401835A/en not_active Expired - Fee Related
-
1982
- 1982-09-14 ZA ZA826743A patent/ZA826743B/xx unknown
- 1982-09-14 AU AU88379/82A patent/AU550984B2/en not_active Ceased
- 1982-09-16 DE DE8282304874T patent/DE3264919D1/de not_active Expired
- 1982-09-16 EP EP82304874A patent/EP0075442B1/en not_active Expired
- 1982-09-17 JP JP57161118A patent/JPS5869863A/ja active Granted
- 1982-09-17 CA CA000411660A patent/CA1177847A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6140663B2 (cg-RX-API-DMAC7.html) | 1986-09-10 |
| EP0075442B1 (en) | 1985-07-24 |
| AU8837982A (en) | 1983-03-24 |
| EP0075442A1 (en) | 1983-03-30 |
| DE3264919D1 (en) | 1985-08-29 |
| AU550984B2 (en) | 1986-04-10 |
| US4401835A (en) | 1983-08-30 |
| ZA826743B (en) | 1983-07-27 |
| JPS5869863A (ja) | 1983-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |