CN1017246B - 氨基糖碳酸化剂的制备方法 - Google Patents
氨基糖碳酸化剂的制备方法Info
- Publication number
- CN1017246B CN1017246B CN87101874A CN87101874A CN1017246B CN 1017246 B CN1017246 B CN 1017246B CN 87101874 A CN87101874 A CN 87101874A CN 87101874 A CN87101874 A CN 87101874A CN 1017246 B CN1017246 B CN 1017246B
- Authority
- CN
- China
- Prior art keywords
- supercarbonate
- aqueous solution
- bicarbonate
- solution
- glycosamine
- 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
- 150000002337 glycosamines Chemical class 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 24
- 239000007864 aqueous solution Substances 0.000 claims abstract description 23
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract description 22
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 claims abstract description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims description 35
- 235000011089 carbon dioxide Nutrition 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000005342 ion exchange Methods 0.000 claims description 10
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000003456 ion exchange resin Substances 0.000 claims description 8
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 8
- -1 inorganic acid salt Chemical class 0.000 claims description 7
- 238000004108 freeze drying Methods 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000000203 mixture Substances 0.000 abstract description 17
- 235000013361 beverage Nutrition 0.000 abstract description 10
- 235000019605 sweet taste sensations Nutrition 0.000 abstract description 6
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 abstract description 5
- 235000014171 carbonated beverage Nutrition 0.000 abstract description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 abstract 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 2
- 229960002442 glucosamine Drugs 0.000 abstract 2
- 239000000470 constituent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000008367 deionised water Substances 0.000 description 13
- 229910021641 deionized water Inorganic materials 0.000 description 13
- 239000000047 product Substances 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 239000003513 alkali Substances 0.000 description 7
- CBOJBBMQJBVCMW-BTVCFUMJSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;hydrochloride Chemical compound Cl.O=C[C@H](N)[C@@H](O)[C@H](O)[C@H](O)CO CBOJBBMQJBVCMW-BTVCFUMJSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229960001911 glucosamine hydrochloride Drugs 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920002101 Chitin Polymers 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 235000013355 food flavoring agent Nutrition 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- 239000004278 EU approved seasoning Substances 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002535 acidifier Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000011194 food seasoning agent Nutrition 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 229910052806 inorganic carbonate Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KACXHRCBXDCJQZ-WCCKRBBISA-N (2s)-2-amino-4-methylsulfanylbutanoic acid;carbamic acid Chemical compound NC(O)=O.CSCC[C@H](N)C(O)=O KACXHRCBXDCJQZ-WCCKRBBISA-N 0.000 description 1
- APCLRHPWFCQIMG-UHFFFAOYSA-N 4-(5,6-dimethoxy-1-benzothiophen-2-yl)-4-oxobutanoic acid Chemical compound C1=C(OC)C(OC)=CC2=C1SC(C(=O)CCC(O)=O)=C2 APCLRHPWFCQIMG-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 241000238017 Astacoidea Species 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 241000370738 Chlorion Species 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- 244000307700 Fragaria vesca Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- FZHXIRIBWMQPQF-UHFFFAOYSA-N Glc-NH2 Natural products O=CC(N)C(O)C(O)C(O)CO FZHXIRIBWMQPQF-UHFFFAOYSA-N 0.000 description 1
- 229940125791 MSA-2 Drugs 0.000 description 1
- 101710162106 Merozoite surface antigen 2 Proteins 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- FZHXIRIBWMQPQF-SLPGGIOYSA-N aldehydo-D-glucosamine Chemical compound O=C[C@H](N)[C@@H](O)[C@H](O)[C@H](O)CO FZHXIRIBWMQPQF-SLPGGIOYSA-N 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000012174 carbonated soft drink Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000020344 instant tea Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910000150 monocalcium phosphate Inorganic materials 0.000 description 1
- 235000019691 monocalcium phosphate Nutrition 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Non-Alcoholic Beverages (AREA)
- Saccharide Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- General Preparation And Processing Of Foods (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Carbon And Carbon Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/837,718 US4766209A (en) | 1986-03-10 | 1986-03-10 | Amino sugar carbonating agents and their preparation |
| US837718 | 1986-03-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN87101874A CN87101874A (zh) | 1987-10-14 |
| CN1017246B true CN1017246B (zh) | 1992-07-01 |
Family
ID=25275222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN87101874A Expired CN1017246B (zh) | 1986-03-10 | 1987-03-10 | 氨基糖碳酸化剂的制备方法 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4766209A (enExample) |
| EP (1) | EP0236771B1 (enExample) |
| JP (1) | JPS62216910A (enExample) |
| CN (1) | CN1017246B (enExample) |
| AR (1) | AR242220A1 (enExample) |
| AT (1) | ATE63314T1 (enExample) |
| AU (1) | AU586536B2 (enExample) |
| CA (1) | CA1268457A (enExample) |
| DD (1) | DD284588A5 (enExample) |
| DE (1) | DE3769814D1 (enExample) |
| ES (1) | ES2022171B3 (enExample) |
| FI (1) | FI83879C (enExample) |
| GB (1) | GB2187736B (enExample) |
| GR (1) | GR3001921T3 (enExample) |
| HK (1) | HK21490A (enExample) |
| IN (1) | IN169314B (enExample) |
| MX (1) | MX165470B (enExample) |
| MY (1) | MY101153A (enExample) |
| NO (1) | NO164713C (enExample) |
| NZ (1) | NZ219548A (enExample) |
| OA (1) | OA08677A (enExample) |
| PH (1) | PH23026A (enExample) |
| PT (1) | PT84435B (enExample) |
| ZA (1) | ZA871190B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2316851A (en) * | 1996-09-09 | 1998-03-11 | Timothy John Parsons | Carbonated tea |
| US6391864B1 (en) | 1998-08-19 | 2002-05-21 | Joint Juice, Inc. | Food supplement containing a cartilage supplement |
| US6706309B1 (en) | 1998-11-25 | 2004-03-16 | William F. Aftoora | Liquefied water soluble acidity-reducing formulation for food and beverage products |
| US7851458B2 (en) | 1999-06-22 | 2010-12-14 | Joint Juice, Inc. | Cartilage enhancing food supplements and methods of preparing the same |
| AU2005203619B2 (en) * | 1999-06-22 | 2009-02-26 | Premier Nutrition Corporation | Cartilage enhancing food supplements and methods of preparing the same |
| US20030069202A1 (en) * | 2000-06-02 | 2003-04-10 | Kern Kenneth Norman | Compositions, kits, and methods for promoting defined health benefits |
| MXPA02011940A (es) * | 2000-06-02 | 2003-04-22 | Procter & Gamble | Estuches y metodos para optimizar la eficacia de composiciones condroprotectoras. |
| AU2001268129A1 (en) * | 2000-06-02 | 2001-12-17 | The Procter And Gamble Company | Aqueous chondroprotective compositions having defined dosage requirements for efficacious delivery |
| CA2408023C (en) * | 2002-10-15 | 2012-01-03 | Purepharm Inc. | Glucosamine as a food and beverage additive |
| US20070259094A1 (en) * | 2002-10-21 | 2007-11-08 | Willem Wassenaar | N-acetylglucosamine as a food and beverage additive |
| US9089156B2 (en) * | 2006-06-05 | 2015-07-28 | Stokely-Van Camp, Inc. | Reducing muscle soreness with glucosamine compositions |
| CN102415596A (zh) * | 2011-10-14 | 2012-04-18 | 宁波大学 | 一种碳酸饮料 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2297734A (en) * | 1940-12-26 | 1942-10-06 | Trojan Powder Co | Stabilization of nitrated carbohydrates |
| FR1295343A (fr) * | 1959-08-03 | 1962-06-08 | Chugai Pharmaceutical Co Ltd | Procédé de fabrication de dérivés de glucosamine |
| US3441417A (en) * | 1965-10-05 | 1969-04-29 | Gen Foods Corp | Beverage product and process |
| US3518343A (en) * | 1967-10-02 | 1970-06-30 | Miles Lab | Effervescent tablet and process for making same |
| US3649298A (en) * | 1970-04-16 | 1972-03-14 | Gen Mills Inc | Carbonation concentrates for beverages and process of producing carbonated beverages |
| US4127645A (en) * | 1976-05-21 | 1978-11-28 | Life Savers, Inc. | Effervescent tablet and method |
| US4371616A (en) * | 1981-08-26 | 1983-02-01 | Hydrocarbon Research, Inc. | Process for producing L-sugars |
| NZ207813A (en) * | 1983-06-24 | 1986-12-05 | Dridrinks Nv | Effervescent mixture:component(s)coated with water-soluble polysaccharide composition |
| US4579285A (en) * | 1984-04-19 | 1986-04-01 | Hunter Edwin J | Adjustable sprinkler system |
| EP0185196B1 (en) * | 1984-12-13 | 1992-03-04 | Societe Des Produits Nestle S.A. | Carbonation agent |
| DE3505150A1 (de) * | 1985-02-15 | 1986-08-21 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von zuckerketalen |
| JPS61225280A (ja) * | 1985-03-30 | 1986-10-07 | Agency Of Ind Science & Technol | セルロ−ス含有バイオマスの液化方法 |
-
1986
- 1986-03-10 US US06/837,718 patent/US4766209A/en not_active Expired - Lifetime
-
1987
- 1987-02-12 EP EP87101959A patent/EP0236771B1/en not_active Expired - Lifetime
- 1987-02-12 DE DE8787101959T patent/DE3769814D1/de not_active Expired - Fee Related
- 1987-02-12 ES ES87101959T patent/ES2022171B3/es not_active Expired - Lifetime
- 1987-02-12 AT AT87101959T patent/ATE63314T1/de not_active IP Right Cessation
- 1987-02-18 AU AU69025/87A patent/AU586536B2/en not_active Ceased
- 1987-02-18 IN IN111/MAS/87A patent/IN169314B/en unknown
- 1987-02-18 ZA ZA871190A patent/ZA871190B/xx unknown
- 1987-02-19 FI FI870685A patent/FI83879C/fi not_active IP Right Cessation
- 1987-02-26 MX MX026945A patent/MX165470B/es unknown
- 1987-02-26 GB GB8704548A patent/GB2187736B/en not_active Expired
- 1987-02-27 CA CA000530817A patent/CA1268457A/en not_active Expired - Fee Related
- 1987-03-03 PH PH34947A patent/PH23026A/en unknown
- 1987-03-04 MY MYPI87000229A patent/MY101153A/en unknown
- 1987-03-06 DD DD87300533A patent/DD284588A5/de not_active IP Right Cessation
- 1987-03-09 JP JP62053907A patent/JPS62216910A/ja active Granted
- 1987-03-09 NZ NZ219548A patent/NZ219548A/xx unknown
- 1987-03-09 AR AR87306963A patent/AR242220A1/es active
- 1987-03-09 NO NO870965A patent/NO164713C/no not_active IP Right Cessation
- 1987-03-10 PT PT84435A patent/PT84435B/pt unknown
- 1987-03-10 OA OA59082A patent/OA08677A/xx unknown
- 1987-03-10 CN CN87101874A patent/CN1017246B/zh not_active Expired
-
1990
- 1990-03-22 HK HK214/90A patent/HK21490A/xx not_active IP Right Cessation
-
1991
- 1991-05-09 GR GR91400510T patent/GR3001921T3/el unknown
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