NL8503286A - Werkwijze voor het afscheiden en zuiveren van l-fenylalanine. - Google Patents
Werkwijze voor het afscheiden en zuiveren van l-fenylalanine. Download PDFInfo
- Publication number
- NL8503286A NL8503286A NL8503286A NL8503286A NL8503286A NL 8503286 A NL8503286 A NL 8503286A NL 8503286 A NL8503286 A NL 8503286A NL 8503286 A NL8503286 A NL 8503286A NL 8503286 A NL8503286 A NL 8503286A
- Authority
- NL
- Netherlands
- Prior art keywords
- phenylalanine
- activated carbon
- solution
- ion exchanger
- process according
- Prior art date
Links
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 title claims description 158
- 229960005190 phenylalanine Drugs 0.000 title claims description 141
- 238000000034 method Methods 0.000 title claims description 49
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 149
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 121
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 39
- 239000000243 solution Substances 0.000 claims description 39
- 150000002500 ions Chemical class 0.000 claims description 36
- 238000001179 sorption measurement Methods 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000003480 eluent Substances 0.000 claims description 21
- 239000007864 aqueous solution Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 229910021529 ammonia Inorganic materials 0.000 claims description 16
- 239000012535 impurity Substances 0.000 claims description 16
- 238000002425 crystallisation Methods 0.000 claims description 15
- 230000008025 crystallization Effects 0.000 claims description 15
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- 239000011347 resin Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 238000011068 loading method Methods 0.000 claims description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
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- 239000000203 mixture Substances 0.000 claims description 2
- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
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- 235000008729 phenylalanine Nutrition 0.000 description 115
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- 239000002904 solvent Substances 0.000 description 11
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- 238000000746 purification Methods 0.000 description 9
- -1 alkali metal salts Chemical class 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
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- JLNTWVDSQRNWFU-UHFFFAOYSA-N OOOOOOO Chemical compound OOOOOOO JLNTWVDSQRNWFU-UHFFFAOYSA-N 0.000 description 7
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- 238000000108 ultra-filtration Methods 0.000 description 7
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- 239000000706 filtrate Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
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- 239000002245 particle Substances 0.000 description 6
- 239000002243 precursor Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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- 239000003245 coal Substances 0.000 description 4
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 239000012531 culture fluid Substances 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 150000002994 phenylalanines Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- DEDGUGJNLNLJSR-UHFFFAOYSA-N alpha-hydroxycinnamic acid Natural products OC(=O)C(O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
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- 238000004809 thin layer chromatography Methods 0.000 description 2
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- 238000010626 work up procedure Methods 0.000 description 2
- VWTFNYVAFGYEKI-QMMMGPOBSA-N (2s)-2-azaniumyl-3-(3,4-dimethoxyphenyl)propanoate Chemical compound COC1=CC=C(C[C@H](N)C(O)=O)C=C1OC VWTFNYVAFGYEKI-QMMMGPOBSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 108050001049 Extracellular proteins Proteins 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
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- 235000004279 alanine Nutrition 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
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- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
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- 238000011069 regeneration method Methods 0.000 description 1
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- 235000009566 rice Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- MQGYVGKMCRDEAF-UHFFFAOYSA-M sodium;2-oxo-3-phenylpropanoate Chemical compound [Na+].[O-]C(=O)C(=O)CC1=CC=CC=C1 MQGYVGKMCRDEAF-UHFFFAOYSA-M 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
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- 239000011721 thiamine Substances 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
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- 229930003231 vitamin Natural products 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/22—Tryptophan; Tyrosine; Phenylalanine; 3,4-Dihydroxyphenylalanine
- C12P13/222—Phenylalanine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/28—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US67536884 | 1984-11-27 | ||
US06/675,368 US4584399A (en) | 1984-11-27 | 1984-11-27 | Purification of L-phenylalanine |
Publications (1)
Publication Number | Publication Date |
---|---|
NL8503286A true NL8503286A (nl) | 1986-06-16 |
Family
ID=24710168
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NL8503286A NL8503286A (nl) | 1984-11-27 | 1985-11-27 | Werkwijze voor het afscheiden en zuiveren van l-fenylalanine. |
Country Status (11)
Country | Link |
---|---|
US (1) | US4584399A (ja) |
JP (1) | JPS61148147A (ja) |
AU (1) | AU578573B2 (ja) |
CA (1) | CA1228601A (ja) |
CH (1) | CH671221A5 (ja) |
DE (1) | DE3541807A1 (ja) |
FR (1) | FR2573757B1 (ja) |
GB (1) | GB2167418B (ja) |
IT (1) | IT1186769B (ja) |
NL (1) | NL8503286A (ja) |
SE (1) | SE8505451L (ja) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4661629A (en) * | 1985-12-02 | 1987-04-28 | The Standard Oil Company | Separation of phenylalanine from phenylalanine ethyl ester |
US4886889A (en) * | 1986-05-16 | 1989-12-12 | Henkel Corporation | Process for recovery of an amino acid from aqueous mixtures thereof |
US4731469A (en) * | 1986-08-06 | 1988-03-15 | Synthetech, Inc. | Process for recovery and purification of L-phenylalanine |
US4740615A (en) * | 1986-10-29 | 1988-04-26 | Merck & Co., Inc. | Process for purified amino acids |
DE3702689A1 (de) * | 1987-01-30 | 1988-08-11 | Degussa | Verfahren zur isolierung von l-aminosaeuren |
US4912228A (en) * | 1988-08-04 | 1990-03-27 | Henkel Research Corporation | Process of extraction of amino acids from aqueous solutions thereof |
US4910336A (en) * | 1988-11-25 | 1990-03-20 | Uop | Process for separating phenylalanine from salts |
US4960930A (en) * | 1989-10-19 | 1990-10-02 | Miwon Co., Ltd. | Process for purification and recovery of L-phenylalanine |
DE4006402A1 (de) * | 1990-03-01 | 1991-09-05 | Wolff Walsrode Ag | Hochgleitfaehige, gereckte polypropylenfolien |
CN106631852A (zh) * | 2016-09-30 | 2017-05-10 | 南京工业大学 | 一种从l‑鸟氨酸发酵液中提取l‑鸟氨酸盐酸盐的方法 |
CA3149377A1 (en) * | 2019-08-02 | 2021-02-11 | Ajinomoto Co., Inc. | Method for producing glycomacropeptide |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3917511A (en) * | 1970-07-29 | 1975-11-04 | Kyowa Hakko Kogyo Kk | Process for preparing L-phenylalanine |
JPS5610035B1 (ja) * | 1970-07-29 | 1981-03-05 | ||
JPS4818475B1 (ja) * | 1970-09-30 | 1973-06-06 | ||
SU960163A1 (ru) * | 1980-07-28 | 1982-09-23 | Предприятие П/Я Г-4740 | Способ очистки L-пролина |
DD211337A1 (de) * | 1982-11-12 | 1984-07-11 | Berlin Chemie Veb | Verbessertes verfahren zur entfernung von phenylalanin aus proteinhydrolysaten mittels aktivkohle |
-
1984
- 1984-11-27 US US06/675,368 patent/US4584399A/en not_active Expired - Fee Related
-
1985
- 1985-06-18 CA CA000484296A patent/CA1228601A/en not_active Expired
- 1985-11-18 SE SE8505451A patent/SE8505451L/xx not_active Application Discontinuation
- 1985-11-20 JP JP60258793A patent/JPS61148147A/ja active Pending
- 1985-11-21 GB GB08528736A patent/GB2167418B/en not_active Expired
- 1985-11-21 CH CH4970/85A patent/CH671221A5/de not_active IP Right Cessation
- 1985-11-23 DE DE19853541807 patent/DE3541807A1/de not_active Withdrawn
- 1985-11-25 AU AU50309/85A patent/AU578573B2/en not_active Ceased
- 1985-11-25 IT IT22977/85A patent/IT1186769B/it active
- 1985-11-26 FR FR858517467A patent/FR2573757B1/fr not_active Expired
- 1985-11-27 NL NL8503286A patent/NL8503286A/nl not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
JPS61148147A (ja) | 1986-07-05 |
IT8522977A0 (it) | 1985-11-25 |
FR2573757B1 (fr) | 1989-06-16 |
GB2167418A (en) | 1986-05-29 |
DE3541807A1 (de) | 1986-06-05 |
FR2573757A1 (fr) | 1986-05-30 |
IT1186769B (it) | 1987-12-16 |
US4584399A (en) | 1986-04-22 |
GB2167418B (en) | 1989-01-25 |
SE8505451L (sv) | 1986-05-28 |
AU578573B2 (en) | 1988-10-27 |
CA1228601A (en) | 1987-10-27 |
GB8528736D0 (en) | 1985-12-24 |
CH671221A5 (ja) | 1989-08-15 |
AU5030985A (en) | 1986-06-05 |
SE8505451D0 (sv) | 1985-11-18 |
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