FI73962C - Foerfarande foer framstaellning av vanillin. - Google Patents
Foerfarande foer framstaellning av vanillin. Download PDFInfo
- Publication number
- FI73962C FI73962C FI850858A FI850858A FI73962C FI 73962 C FI73962 C FI 73962C FI 850858 A FI850858 A FI 850858A FI 850858 A FI850858 A FI 850858A FI 73962 C FI73962 C FI 73962C
- Authority
- FI
- Finland
- Prior art keywords
- vanillin
- carbon dioxide
- extraction
- oxidized
- pressure
- Prior art date
Links
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 title claims description 88
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 title claims description 88
- 235000012141 vanillin Nutrition 0.000 title claims description 88
- 238000000034 method Methods 0.000 title claims description 21
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 72
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 35
- 239000001569 carbon dioxide Substances 0.000 claims description 35
- 238000000605 extraction Methods 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 12
- 239000007789 gas Substances 0.000 claims description 11
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 239000003546 flue gas Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002002 slurry Substances 0.000 claims description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002699 waste material Substances 0.000 description 14
- 239000000284 extract Substances 0.000 description 12
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 12
- 229920005610 lignin Polymers 0.000 description 9
- 239000012535 impurity Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 6
- 229960001867 guaiacol Drugs 0.000 description 6
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 6
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- 238000000194 supercritical-fluid extraction Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010411 cooking Methods 0.000 description 3
- 239000007857 degradation product Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- NSTQUZVZBUTVPY-UHFFFAOYSA-N 3-(5-formyl-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(C=2C(=C(OC)C=C(C=O)C=2)O)=C1O NSTQUZVZBUTVPY-UHFFFAOYSA-N 0.000 description 2
- -1 4-hydroxy-3-methoxyphenyl Chemical group 0.000 description 2
- YVNRFQCFZVYDRO-UHFFFAOYSA-N 4-hydroxy-5-methoxybenzene-1,3-dicarbaldehyde Chemical compound COC1=CC(C=O)=CC(C=O)=C1O YVNRFQCFZVYDRO-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920002201 Oxidized cellulose Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- 229940107304 oxidized cellulose Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 238000003815 supercritical carbon dioxide extraction Methods 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 239000004117 Lignosulphonate Substances 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/783—Separation; Purification; Stabilisation; Use of additives by gas-liquid treatment, e.g. by gas-liquid absorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
- Manufacture Of Tobacco Products (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI850858A FI73962C (fi) | 1985-03-01 | 1985-03-01 | Foerfarande foer framstaellning av vanillin. |
| FR8602670A FR2578246B1 (fr) | 1985-03-01 | 1986-02-26 | Procede de preparation de la vanilline |
| DE19863606398 DE3606398A1 (de) | 1985-03-01 | 1986-02-27 | Verfahren zur herstellung von vanillin |
| BR8600882A BR8600882A (pt) | 1985-03-01 | 1986-02-28 | Processo para a producao de vanilina |
| CN86101165.1A CN1004807B (zh) | 1985-03-01 | 1986-02-28 | 生产香草醛的方法 |
| JP61042024A JPS61225149A (ja) | 1985-03-01 | 1986-02-28 | バニリンの製造方法 |
| NO860745A NO163565C (no) | 1985-03-01 | 1986-02-28 | Fremgangsmaate ved fremstilling av vanillin. |
| SE8600952A SE8600952L (sv) | 1985-03-01 | 1986-03-03 | Forfarande for framstellning av vanillin |
| US07/105,579 US4847422A (en) | 1985-03-01 | 1987-10-08 | Method for the production of vanillin |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI850858A FI73962C (fi) | 1985-03-01 | 1985-03-01 | Foerfarande foer framstaellning av vanillin. |
| FI850858 | 1985-03-01 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI850858A0 FI850858A0 (fi) | 1985-03-01 |
| FI850858L FI850858L (fi) | 1986-09-02 |
| FI73962B FI73962B (fi) | 1987-08-31 |
| FI73962C true FI73962C (fi) | 1987-12-10 |
Family
ID=8520456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI850858A FI73962C (fi) | 1985-03-01 | 1985-03-01 | Foerfarande foer framstaellning av vanillin. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4847422A (d) |
| JP (1) | JPS61225149A (d) |
| CN (1) | CN1004807B (d) |
| BR (1) | BR8600882A (d) |
| DE (1) | DE3606398A1 (d) |
| FI (1) | FI73962C (d) |
| FR (1) | FR2578246B1 (d) |
| NO (1) | NO163565C (d) |
| SE (1) | SE8600952L (d) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI73962C (fi) * | 1985-03-01 | 1987-12-10 | Yhtyneet Paperitehtaat Oy | Foerfarande foer framstaellning av vanillin. |
| DE3533562A1 (de) * | 1985-09-20 | 1987-04-02 | Krupp Gmbh | Verfahren zur gewinnung von vanillin |
| DE4202657C2 (de) * | 1992-01-31 | 1995-10-12 | Schaper & Bruemmer Gmbh | Pharmazeutisch wirksame Zusammensetzung aus Tanacetum parthenium sowie Verfahren zu deren Extraktion und mit der pharmazeutisch wirksamen Zusammensetzung hergestelltes Arzneimittel |
| DE19649655A1 (de) * | 1996-11-29 | 1998-06-04 | Haarmann & Reimer Gmbh | Syntheseenzyme für die Herstellung von Coniferylalkohol, Coniferylaldehyd, Ferulasäure, Vanillin und Vanillinsäure und deren Verwendung |
| EP1127101B1 (en) * | 2000-05-31 | 2006-08-09 | Shiseido Co., Ltd. | Method of collection of fragrance ingredient, perfume composition and cosmetics containing same |
| RU2178405C1 (ru) * | 2000-07-11 | 2002-01-20 | Институт химии и химической технологии СО РАН | Способ переработки древесины мелколиственных пород |
| JP4398867B2 (ja) * | 2002-10-30 | 2010-01-13 | サントリーホールディングス株式会社 | 植物加工品の製造方法 |
| GB0307232D0 (en) * | 2003-03-28 | 2003-04-30 | Zylepsis Ltd | Production of vanillin |
| US20050074519A1 (en) * | 2003-10-01 | 2005-04-07 | Sensient Flavors Inc. | Method for the production of natural botanical extracts |
| US20050074521A1 (en) * | 2003-10-01 | 2005-04-07 | Sensient Flavors Inc. | Method for the production of natural botanical extracts |
| US20050074520A1 (en) * | 2003-10-01 | 2005-04-07 | Sensient Flavors Inc. | Method for the production of natural botanical extracts |
| US20060088627A1 (en) * | 2004-10-25 | 2006-04-27 | Sensient Flavors Inc. | Methods for the production of food grade extracts |
| CN101386570B (zh) * | 2007-09-10 | 2010-09-29 | 中国石油天然气集团公司 | 二氧化碳超临界萃取香兰素或乙基香兰素粗制品的方法 |
| CN101386571B (zh) * | 2007-09-10 | 2011-05-25 | 中国石油天然气集团公司 | 二氧化碳超临界连续萃取酸性水溶液中香兰素及其衍生物的方法 |
| US8969534B2 (en) * | 2013-02-20 | 2015-03-03 | Wisconsin Alumni Research Foundataion | Selective aerobic alcohol oxidation method for conversion of lignin into simple aromatic compounds |
| JP2016516676A (ja) * | 2013-03-08 | 2016-06-09 | ユニバーシティ オブ セントラル フロリダ リサーチ ファウンデーション，インコーポレイテッド | ポリマー含有物質を機械触媒的に酸化解重合させるための触媒およびそれを用いて酸化反応生成物を製造する方法 |
| CN103626642A (zh) * | 2013-11-28 | 2014-03-12 | 上海应用技术学院 | 一种制备香兰素的方法 |
| US20170172184A1 (en) * | 2014-02-12 | 2017-06-22 | Evolva Sa | Methods of Improving Production of Vanillin |
| CN107986950A (zh) * | 2017-11-27 | 2018-05-04 | 昆山亚香香料股份有限公司 | 一种利用木质素化学提取高纯度香兰素的工艺方法 |
| CN110078877B (zh) * | 2019-04-26 | 2021-07-27 | 福州大学 | 一种利用木质素降解产物制备分散剂的方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB318939A (en) * | 1928-05-11 | 1929-09-11 | Graesser Monsanto Chemical Wor | Improvements in and relating to the separation, isolation, and purification of aromatic hydroxy aldehydes |
| US2069185A (en) * | 1934-12-27 | 1937-01-26 | Howard Smith Chemicals Ltd | Manufacture of vanillin from waste sulphite pulp liquor |
| US4198432A (en) * | 1971-06-03 | 1980-04-15 | Studiengesellschaft Kohle Mbh | Process for the production of spice extracts |
| US4075248A (en) * | 1976-09-07 | 1978-02-21 | Domtar Limited | Production of syringealdehyde from hardwood waste pulping liquors |
| DE3137230A1 (de) * | 1981-09-18 | 1983-04-21 | Haarmann & Reimer Gmbh, 3450 Holzminden | Verfahren zur extraktion der aromastoffe der vanillekapsel |
| US4474994A (en) * | 1982-09-13 | 1984-10-02 | Monsanto Company | Purification of vanillin |
| FI73962C (fi) * | 1985-03-01 | 1987-12-10 | Yhtyneet Paperitehtaat Oy | Foerfarande foer framstaellning av vanillin. |
| DE3533562A1 (de) * | 1985-09-20 | 1987-04-02 | Krupp Gmbh | Verfahren zur gewinnung von vanillin |
-
1985
- 1985-03-01 FI FI850858A patent/FI73962C/fi not_active IP Right Cessation
-
1986
- 1986-02-26 FR FR8602670A patent/FR2578246B1/fr not_active Expired
- 1986-02-27 DE DE19863606398 patent/DE3606398A1/de active Granted
- 1986-02-28 NO NO860745A patent/NO163565C/no unknown
- 1986-02-28 BR BR8600882A patent/BR8600882A/pt unknown
- 1986-02-28 CN CN86101165.1A patent/CN1004807B/zh not_active Expired
- 1986-02-28 JP JP61042024A patent/JPS61225149A/ja active Granted
- 1986-03-03 SE SE8600952A patent/SE8600952L/xx not_active Application Discontinuation
-
1987
- 1987-10-08 US US07/105,579 patent/US4847422A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3606398A1 (de) | 1986-10-30 |
| FR2578246A1 (fr) | 1986-09-05 |
| US4847422A (en) | 1989-07-11 |
| NO163565B (no) | 1990-03-12 |
| DE3606398C2 (d) | 1988-12-22 |
| JPH0129780B2 (d) | 1989-06-14 |
| FI73962B (fi) | 1987-08-31 |
| NO860745L (d) | 1986-09-02 |
| NO163565C (no) | 1990-06-20 |
| FI850858L (fi) | 1986-09-02 |
| JPS61225149A (ja) | 1986-10-06 |
| CN1004807B (zh) | 1989-07-19 |
| CN86101165A (zh) | 1986-08-27 |
| SE8600952D0 (sv) | 1986-03-03 |
| BR8600882A (pt) | 1986-11-11 |
| SE8600952L (sv) | 1986-09-02 |
| FI850858A0 (fi) | 1985-03-01 |
| FR2578246B1 (fr) | 1989-07-21 |
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