JPS6253745A - 芳香族ニトロ化合物の気相還元用触媒の再生法 - Google Patents
芳香族ニトロ化合物の気相還元用触媒の再生法Info
- Publication number
- JPS6253745A JPS6253745A JP61194108A JP19410886A JPS6253745A JP S6253745 A JPS6253745 A JP S6253745A JP 61194108 A JP61194108 A JP 61194108A JP 19410886 A JP19410886 A JP 19410886A JP S6253745 A JPS6253745 A JP S6253745A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- regeneration
- nitrobenzene
- hours
- nitrogen
- 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.)
- Pending
Links
- 239000003054 catalyst Substances 0.000 title claims description 77
- -1 aromatic nitro compound Chemical class 0.000 title claims description 9
- 238000011069 regeneration method Methods 0.000 title description 54
- 230000008929 regeneration Effects 0.000 title description 49
- 239000007792 gaseous phase Substances 0.000 title 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 91
- 238000000034 method Methods 0.000 claims description 64
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 45
- 238000004519 manufacturing process Methods 0.000 claims description 35
- 239000007789 gas Substances 0.000 claims description 29
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 29
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 13
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 150000001875 compounds Chemical group 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 150000004982 aromatic amines Chemical class 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 150000002429 hydrazines Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 230000001172 regenerating effect Effects 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002443 hydroxylamines Chemical class 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 13
- 235000011114 ammonium hydroxide Nutrition 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 230000003247 decreasing effect Effects 0.000 description 11
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 6
- 239000003345 natural gas Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 150000004992 toluidines Chemical class 0.000 description 3
- QZYHIOPPLUPUJF-UHFFFAOYSA-N 3-nitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1 QZYHIOPPLUPUJF-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101100081489 Drosophila melanogaster Obp83a gene Proteins 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229960003753 nitric oxide Drugs 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000000629 steam reforming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/04—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst
- B01J38/12—Treating with free oxygen-containing gas
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/90—Regeneration or reactivation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853530820 DE3530820A1 (de) | 1985-08-29 | 1985-08-29 | Verfahren zur regeneration von katalysatoren fuer die gasphasenreduktion von aromatischen nitroverbindungen |
| DE3530820.6 | 1985-08-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6253745A true JPS6253745A (ja) | 1987-03-09 |
Family
ID=6279627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61194108A Pending JPS6253745A (ja) | 1985-08-29 | 1986-08-21 | 芳香族ニトロ化合物の気相還元用触媒の再生法 |
Country Status (5)
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06103721A (ja) * | 1992-09-22 | 1994-04-15 | Inoac Corp | ディスクカートリッジ |
| JP2008207147A (ja) * | 2007-02-28 | 2008-09-11 | Tosoh Corp | 水素化触媒の再生方法 |
| JP2010526791A (ja) * | 2007-05-10 | 2010-08-05 | ビーエーエスエフ ソシエタス・ヨーロピア | アミンの製造方法 |
| JP2015519310A (ja) * | 2012-04-16 | 2015-07-09 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフトＢａｙｅｒ ＭａｔｅｒｉａｌＳｃｉｅｎｃｅ ＡＧ | 芳香族ニトロ化合物から芳香族アミンを製造する間に反応を開始するための改良方法 |
| JP2022512758A (ja) * | 2018-10-17 | 2022-02-07 | 中国石油化工股▲ふん▼有限公司 | ニトロ化合物の水素化反応プロセス、および水素化反応装置 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5183821A (en) * | 1983-09-19 | 1993-02-02 | Laboratories Knoll, S.A. | Method for treating leukemias using N-(2-dimethylaminoethyl)-3-amino-1,8-naphthalimide for treating leukemias and solid tumors |
| WO1993024224A1 (en) * | 1992-05-28 | 1993-12-09 | Imperial Chemical Industries Plc | Treatment of hydrogenation catalysts |
| US5849662A (en) * | 1993-10-21 | 1998-12-15 | Chulalongkorn University | Catalyst comprising of element from group 1B and VIIIB activated by oxygen or oxygen containing compound |
| FR2771949B1 (fr) * | 1997-12-08 | 2000-01-14 | Inst Francais Du Petrole | Procede de regeneration de catalyseur utilise pour la transformation des hydrocarbures |
| FR2771950B1 (fr) * | 1997-12-08 | 2000-01-14 | Inst Francais Du Petrole | Procede de regeneration de catalyseurs et d'adsorbants |
| CN1080593C (zh) * | 1998-08-06 | 2002-03-13 | 南京四力化工有限公司 | 流化床气相催化加氢催化剂无氮再生活化新方法 |
| US6521791B1 (en) * | 2001-11-09 | 2003-02-18 | Air Products And Chemicals, Inc. | Process for regenerating a monolith hydrogenation catalytic reactor |
| DE102009019436A1 (de) * | 2009-04-29 | 2010-11-04 | Bayer Materialscience Ag | Verfahren zur Herstellung von aromatischen Aminen |
| PT2598241E (pt) * | 2010-07-30 | 2014-07-09 | Bayer Ip Gmbh | Processo para restaurar a actividade de um catalisador |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB337348A (en) * | 1929-07-23 | 1930-10-23 | Cecil Howard Lander | Improved method of treating activated charcoals |
| US2292879A (en) * | 1939-08-05 | 1942-08-11 | Solvay Process Co | Production of aromatic amines |
| US2891094A (en) * | 1955-02-17 | 1959-06-16 | American Cyanamid Co | New catalyst for reducing nitrobenzene and the process of reducing nitrobenzene thereover |
| US2822397A (en) * | 1955-08-18 | 1958-02-04 | Allied Chem & Dye Corp | Catalytic hydrogenation of aromatic nitro compounds to amines |
| US2963443A (en) * | 1958-05-29 | 1960-12-06 | Universal Oil Prod Co | Reactivation of molybdenum containing catalysts |
| US3243383A (en) * | 1963-11-07 | 1966-03-29 | Monsanto Co | Process for regenerating catalysts |
| US3451942A (en) * | 1965-12-06 | 1969-06-24 | Standard Oil Co | Catalyst-rejuvenation process |
| NL7114406A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1970-10-22 | 1972-04-25 | ||
| DE2459761A1 (de) * | 1974-12-18 | 1976-07-01 | Hoechst Ag | Verfahren zur reaktivierung kupfer bzw. kupfer und chrom enthaltender hydrierkontakte |
| US4164481A (en) * | 1978-01-27 | 1979-08-14 | The Dow Chemical Company | Process of regenerating a noble metal catalyst used in the reduction of organic nitro compounds |
-
1985
- 1985-08-29 DE DE19853530820 patent/DE3530820A1/de active Granted
-
1986
- 1986-08-07 US US06/894,581 patent/US4714689A/en not_active Expired - Fee Related
- 1986-08-18 DE DE8686111377T patent/DE3660746D1/de not_active Expired
- 1986-08-18 EP EP86111377A patent/EP0212602B1/de not_active Expired
- 1986-08-21 JP JP61194108A patent/JPS6253745A/ja active Pending
- 1986-08-28 BR BR8604109A patent/BR8604109A/pt unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06103721A (ja) * | 1992-09-22 | 1994-04-15 | Inoac Corp | ディスクカートリッジ |
| JP2008207147A (ja) * | 2007-02-28 | 2008-09-11 | Tosoh Corp | 水素化触媒の再生方法 |
| JP2010526791A (ja) * | 2007-05-10 | 2010-08-05 | ビーエーエスエフ ソシエタス・ヨーロピア | アミンの製造方法 |
| JP2015519310A (ja) * | 2012-04-16 | 2015-07-09 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフトＢａｙｅｒ ＭａｔｅｒｉａｌＳｃｉｅｎｃｅ ＡＧ | 芳香族ニトロ化合物から芳香族アミンを製造する間に反応を開始するための改良方法 |
| JP2022512758A (ja) * | 2018-10-17 | 2022-02-07 | 中国石油化工股▲ふん▼有限公司 | ニトロ化合物の水素化反応プロセス、および水素化反応装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR8604109A (pt) | 1987-04-22 |
| EP0212602A1 (de) | 1987-03-04 |
| DE3530820C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-07-21 |
| DE3660746D1 (en) | 1988-10-27 |
| DE3530820A1 (de) | 1987-03-05 |
| EP0212602B1 (de) | 1988-09-21 |
| US4714689A (en) | 1987-12-22 |
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