CA1177827A - Process for preparing alkali metal salt of carboxymethyl cellulose - Google Patents
Process for preparing alkali metal salt of carboxymethyl celluloseInfo
- Publication number
- CA1177827A CA1177827A CA000412531A CA412531A CA1177827A CA 1177827 A CA1177827 A CA 1177827A CA 000412531 A CA000412531 A CA 000412531A CA 412531 A CA412531 A CA 412531A CA 1177827 A CA1177827 A CA 1177827A
- Authority
- CA
- Canada
- Prior art keywords
- cellulose
- isopropanol
- alkali metal
- weight
- solution
- 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
- 229920002134 Carboxymethyl cellulose Polymers 0.000 title claims abstract description 83
- 235000010948 carboxy methyl cellulose Nutrition 0.000 title claims abstract description 83
- 239000001768 carboxy methyl cellulose Substances 0.000 title claims abstract description 9
- 239000008112 carboxymethyl-cellulose Substances 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 229910052783 alkali metal Inorganic materials 0.000 title claims description 14
- -1 alkali metal salt Chemical class 0.000 title claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 99
- 239000001913 cellulose Substances 0.000 claims abstract description 69
- 229920002678 cellulose Polymers 0.000 claims abstract description 64
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 48
- 229910001868 water Inorganic materials 0.000 claims abstract description 48
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 22
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003513 alkali Substances 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 229960005215 dichloroacetic acid Drugs 0.000 claims abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 87
- 239000000243 solution Substances 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 239000007864 aqueous solution Substances 0.000 claims description 12
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 6
- 238000010008 shearing Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 238000010298 pulverizing process Methods 0.000 claims description 2
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 abstract description 16
- 239000001110 calcium chloride Substances 0.000 abstract description 12
- 229910001628 calcium chloride Inorganic materials 0.000 abstract description 12
- 238000006266 etherification reaction Methods 0.000 abstract description 5
- 235000010980 cellulose Nutrition 0.000 description 50
- 229960004592 isopropanol Drugs 0.000 description 30
- 239000012530 fluid Substances 0.000 description 23
- 238000005553 drilling Methods 0.000 description 14
- 238000002156 mixing Methods 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 9
- 229910001424 calcium ion Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 229940106135 cellulose Drugs 0.000 description 5
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 229940023144 sodium glycolate Drugs 0.000 description 4
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 4
- 241000157282 Aesculus Species 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 229960005069 calcium Drugs 0.000 description 3
- 235000001465 calcium Nutrition 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000010181 horse chestnut Nutrition 0.000 description 3
- 230000009974 thixotropic effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000448280 Elates Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SQMCFUSVGSBKFK-UHFFFAOYSA-M sodium;5-(cyclohexen-1-yl)-1,5-dimethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].O=C1N(C)C(=O)[N-]C(=O)C1(C)C1=CCCCC1 SQMCFUSVGSBKFK-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
- C08B11/10—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals
- C08B11/12—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals substituted with carboxylic radicals, e.g. carboxymethylcellulose [CMC]
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/331,299 US4401813A (en) | 1981-12-10 | 1981-12-10 | Process for preparing alkali metal salt of carboxymethyl cellulose |
| US331,299 | 1981-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1177827A true CA1177827A (en) | 1984-11-13 |
Family
ID=23293377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000412531A Expired CA1177827A (en) | 1981-12-10 | 1982-09-30 | Process for preparing alkali metal salt of carboxymethyl cellulose |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4401813A (enExample) |
| BR (1) | BR8207090A (enExample) |
| CA (1) | CA1177827A (enExample) |
| DE (1) | DE3245794A1 (enExample) |
| ES (1) | ES8404378A1 (enExample) |
| FR (1) | FR2518551B1 (enExample) |
| GB (1) | GB2111058B (enExample) |
| IT (1) | IT1155077B (enExample) |
| MX (1) | MX159764A (enExample) |
| NL (1) | NL186637C (enExample) |
| NO (1) | NO159020C (enExample) |
| SG (1) | SG26286G (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3236158A1 (de) * | 1982-09-30 | 1984-04-05 | Hoechst Ag, 6230 Frankfurt | Verfahren zur veretherung von cellulose mit monochloressigsaeurealkylestern |
| JPS6037121B2 (ja) * | 1982-10-04 | 1985-08-24 | ダイセル化学工業株式会社 | カルボキシメチルセルロ−スナトリウム塩 |
| USRE32976E (en) * | 1982-10-04 | 1989-07-04 | Daicel Chemical Industries, Ltd. | Sodium carboxymethylcellulose |
| US4726912A (en) * | 1986-08-27 | 1988-02-23 | Phillips Petroleum Company | Stable suspensions of carboxymethyl cellulose and their preparation |
| US6413362B1 (en) | 1999-11-24 | 2002-07-02 | Kimberly-Clark Worldwide, Inc. | Method of steam treating low yield papermaking fibers to produce a permanent curl |
| BR9916641A (pt) | 1998-12-30 | 2001-09-25 | Kimberly Clark Co | Processo de reciclagem por explosão a vapor de fibras e tecidos fabricados a partir das fibras recicladas |
| JP2002078733A (ja) * | 2000-06-28 | 2002-03-19 | Uni Charm Corp | 吸収性物品 |
| CN101240035B (zh) * | 2008-03-14 | 2010-05-12 | 山东一滕化工有限公司 | 特高取代纤维素羧甲基钠及其制备方法和应用 |
| BR112014028085B1 (pt) | 2012-05-09 | 2021-04-13 | Vale S.A. | Processo para obtenção de carboximetilcelulose a partir de resíduos agroindustriais, uso da carboximetilcelulose, composição de ligante e uso de uma composição de ligante |
| CN104844715A (zh) * | 2015-05-08 | 2015-08-19 | 郝军元 | 一种羧甲基纤维素的制备方法 |
| WO2022216789A1 (en) * | 2021-04-06 | 2022-10-13 | Isp Investments Llc | Aqueous personal care compositions comprising carboxymethyl cellulose (cmc) having an optimized degree of substitution |
| EP4393960A1 (en) | 2022-12-29 | 2024-07-03 | CMC Spolka Akcyjna | Method for manufacturing sodium carboxymethyl cellulose |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2148952A (en) * | 1937-04-15 | 1939-02-28 | Du Pont | Process for preparing cellulose ethers and products |
| US2425768A (en) * | 1944-08-12 | 1947-08-19 | Phillips Petroleum Co | Drilling fluids and method of use |
| US2512338A (en) * | 1947-04-29 | 1950-06-20 | Hercules Powder Co Ltd | Preparation of cellulose ethers |
| US2536113A (en) * | 1947-08-15 | 1951-01-02 | Phillips Petroleum Co | Well drilling fluids and methods of use |
| US2513807A (en) * | 1948-06-04 | 1950-07-04 | Hercules Powder Co Ltd | Manufacture of carboxyalkyl cellulose |
| US2607772A (en) * | 1949-12-21 | 1952-08-19 | Ici Ltd | Production of powdery products comprising carboxymethyl cellulose |
| US2715124A (en) * | 1953-06-29 | 1955-08-09 | Hercules Powder Co Ltd | Manufacture of free-flowing watersoluble carboxyalkyl cellulose ethers |
| US2839526A (en) * | 1954-12-30 | 1958-06-17 | Hercules Powder Co Ltd | Water-soluble carboxyalkyl cellulose derivative and method of manufacture |
| US3085087A (en) * | 1956-09-13 | 1963-04-09 | Hercules Powder Co Ltd | Preparation of carboxyalkyl cellulose ethers |
| US3069409A (en) * | 1958-06-12 | 1962-12-18 | Hercules Powder Co Ltd | Process of preparing carboxyalkyl cellulose ethers |
| US3088943A (en) * | 1960-10-21 | 1963-05-07 | Du Pont | Process for making alkali metal salt of carboxymethylcellulose |
| US3374224A (en) * | 1964-12-28 | 1968-03-19 | Du Pont | Novel preparation of carboxymethyl cellulose |
| US3284441A (en) * | 1965-07-26 | 1966-11-08 | Hercules Inc | Process of preparing carboxymethyl-cellulose |
| US3498971A (en) * | 1967-02-13 | 1970-03-03 | Allied Chem | Process for the preparation of sodium carboxymethylcellulose |
| US3954628A (en) * | 1973-11-26 | 1976-05-04 | Phillips Petroleum Company | Preparation of sea water muds useful for earth drilling operations |
| US4063018A (en) * | 1975-04-07 | 1977-12-13 | Daicel Ltd. | Process for preparing alkali metal salt of carboxymethyl cellulose ether |
| US4254258A (en) * | 1979-03-28 | 1981-03-03 | Texas A & M University System | Process for the preparation of cellulose ether derivatives |
| DE2929002A1 (de) * | 1979-07-18 | 1981-02-12 | Henkel Kgaa | Verfahren zur herstellung von cellulosederivaten mittels besonders reaktiver alkalicellulose |
| DE3010464A1 (de) * | 1980-03-19 | 1981-10-01 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von wasserarmer alkalicellulose |
-
1981
- 1981-12-10 US US06/331,299 patent/US4401813A/en not_active Expired - Fee Related
-
1982
- 1982-09-30 CA CA000412531A patent/CA1177827A/en not_active Expired
- 1982-10-11 NL NLAANVRAGE8203929,A patent/NL186637C/xx not_active IP Right Cessation
- 1982-10-18 ES ES516609A patent/ES8404378A1/es not_active Expired
- 1982-10-27 NO NO823583A patent/NO159020C/no unknown
- 1982-11-18 MX MX195245A patent/MX159764A/es unknown
- 1982-11-23 GB GB08233389A patent/GB2111058B/en not_active Expired
- 1982-11-25 IT IT24442/82A patent/IT1155077B/it active
- 1982-12-07 BR BR8207090A patent/BR8207090A/pt not_active IP Right Cessation
- 1982-12-07 FR FR8220510A patent/FR2518551B1/fr not_active Expired
- 1982-12-10 DE DE19823245794 patent/DE3245794A1/de active Granted
-
1986
- 1986-03-18 SG SG262/86A patent/SG26286G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO823583L (no) | 1983-06-13 |
| US4401813A (en) | 1983-08-30 |
| NL186637C (nl) | 1991-01-16 |
| BR8207090A (pt) | 1983-10-11 |
| FR2518551B1 (fr) | 1986-09-26 |
| FR2518551A1 (fr) | 1983-06-24 |
| NL8203929A (nl) | 1983-07-01 |
| MX159764A (es) | 1989-08-17 |
| ES516609A0 (es) | 1984-04-16 |
| ES8404378A1 (es) | 1984-04-16 |
| IT8224442A0 (it) | 1982-11-25 |
| IT1155077B (it) | 1987-01-21 |
| NL186637B (nl) | 1990-08-16 |
| NO159020B (no) | 1988-08-15 |
| GB2111058B (en) | 1985-06-12 |
| SG26286G (en) | 1987-03-27 |
| GB2111058A (en) | 1983-06-29 |
| IT8224442A1 (it) | 1984-05-25 |
| DE3245794A1 (de) | 1983-06-23 |
| DE3245794C2 (enExample) | 1988-04-28 |
| NO159020C (no) | 1988-11-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |