KR830007611A - 1,4-부탄디올 및 테트라하이드로푸란의 제조방법 - Google Patents
1,4-부탄디올 및 테트라하이드로푸란의 제조방법 Download PDFInfo
- Publication number
- KR830007611A KR830007611A KR1019810005041A KR810005041A KR830007611A KR 830007611 A KR830007611 A KR 830007611A KR 1019810005041 A KR1019810005041 A KR 1019810005041A KR 810005041 A KR810005041 A KR 810005041A KR 830007611 A KR830007611 A KR 830007611A
- Authority
- KR
- South Korea
- Prior art keywords
- butyrolactone
- weight
- psi
- oxygenated
- maleic anhydride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 title claims 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 229910017052 cobalt Inorganic materials 0.000 claims 5
- 239000010941 cobalt Substances 0.000 claims 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 5
- 229930195733 hydrocarbon Natural products 0.000 claims 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 5
- 229910052742 iron Inorganic materials 0.000 claims 4
- 229910052759 nickel Inorganic materials 0.000 claims 4
- 229910052703 rhodium Inorganic materials 0.000 claims 4
- 239000010948 rhodium Substances 0.000 claims 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 4
- -1 C 4 hydrocarbons Chemical class 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 229910052793 cadmium Inorganic materials 0.000 claims 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims 1
- OYAKWDCOQQBJTJ-UHFFFAOYSA-N furan-2,5-dione;oxolan-2-one Chemical compound O=C1CCCO1.O=C1OC(=O)C=C1 OYAKWDCOQQBJTJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052741 iridium Inorganic materials 0.000 claims 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052762 osmium Inorganic materials 0.000 claims 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 229940014800 succinic anhydride Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/60—Platinum group metals with zinc, cadmium or mercury
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8933—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/8953—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/177—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of a carboxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D307/08—Preparation of tetrahydrofuran
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 말레산 무수물, 말레산, 썩신산 무수물, 썩신산, γ-부티로락톤 및 이들을 2이상 함유하는 혼합물 중에서 선택된 산소화 C4탄화수소를, 약 175℃ 내지 약 275℃의 온도 및 약 750psi내지 약 1500psi의 압력에서, 약 25중량% (산소화 탄화수소의 중량에 대한 비율임) 이하의 물 및 하기 구조식(I)의 촉매 존재하에, 수소와 접촉시켜 산소화 C4탄화수소로 부터 테트라하이드로푸란 및 1,4-부탄디올중 적어도 어느 하나를 제조하는 방법.(상기 구조식에서,M은 니켈과 팔라듐중 적어도 어느 하나이고,M′는 철, 코발트, 로듐, 오스뮴, 이리듐 및 백금중 적어도 어느 하나이고,M″는 아연과 카드뮴중 적어도 어느 하나이며x는 포함된 다른 원소들의 원자가 요구에 알맞는 숫자이다).
- γ-부티로락톤에 용해시킨 말레산 무수물 약 1내지 약 20중량% (혼합물의 총중량에 대한 비율)의 혼합물을, 약 230℃내지 약 250℃의 온도 및 약 1000psi내지 약 1300psi의 압력에서, 약 10중량%(산소화 탄화수소 혼합물의 총중량에 대한 비율) 이하의 물 및 하기 구조식(Ⅳ)의 촉매 존재하에, 수소와 접촉시켜 말레산 무수물로부터 1,4-부탄디올을 제조하는 방법.(상기 구조식에서,M은 니켈과 팔라듐 중 적어도 어느 하나이고,M′는 철, 코발트 및 로듐중 적어도 어느 하나이며,x는 포함된 다른 원소들의 원자가 요구에 알맞는 숫자이다).
- γ-부티로락톤을, 약 175℃ 내지 약 230℃의 온도 및 약 750psi 내지 약 1300psi의 압력에서 약 10중량% (γ-부티로락톤의 총중량에 대한 비율) 이하의 물 및 하기 구조식(V)의 촉매 존재하에 수소와 접촉시켜 γ-부티로 락톤으로 부터 테트라하이드로푸란을 제조하는 방법.(상기 구조식에서, M은 니켈과 팔라듐중 적어도 어느 하나이고,M′는 철, 코발트 및 로듐중 적어도 어느 하나이며x는 포함된 다른 원소들의 원자가 요구에 알맞는 숫자이다.)
- 특허청구범위 제1항에서, 루테늄의 몰비가 약 0.01내지 1.5이고, M 및 M′의 몰비가 약 0.1내지 1.5이며 M″의 몰비가 약 0.05내지 0.8인 제조방법.
- 특허청구범위 제4항에서, M′이 철, 코발트 또는 로듐인 제조방법.
- 특허청구범위 제5항에서 M″가 아연인 제조방법.
- 특허청구범위 제6항에서, M이 니켈인 제조방법.
- 특허청구범위 제7항에서, M′가 코발트인 제조방법.
- 특허청구범위 제8항에서, 산소화 C4탄화수소가 말레산 무수물, γ-부티로락톤 또는 말레산 무수물과 γ-부티로 락톤의 혼합물인 제조방법.
- 특허청구범위 제9항에서, 산소화 C4가γ-부티로락톤에 용해시킨 약 1내지 약 20중량%(혼합물의 중량에 대한 비율임)의 말레산 무수물인 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/218,856 US4301077A (en) | 1980-12-22 | 1980-12-22 | Process for the manufacture of 1-4-butanediol and tetrahydrofuran |
US218856 | 1980-12-22 | ||
US218,856 | 1980-12-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR830007611A true KR830007611A (ko) | 1983-11-04 |
KR880000544B1 KR880000544B1 (ko) | 1988-04-13 |
Family
ID=22816767
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019810005041A KR880000544B1 (ko) | 1980-12-22 | 1981-12-21 | 1,4-부탄디올 및 테트라하이드로푸란의 제조방법 |
Country Status (6)
Country | Link |
---|---|
US (1) | US4301077A (ko) |
EP (1) | EP0055512B1 (ko) |
JP (1) | JPS57109736A (ko) |
KR (1) | KR880000544B1 (ko) |
CA (1) | CA1157031A (ko) |
DE (1) | DE3166724D1 (ko) |
Families Citing this family (64)
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US4863890A (en) * | 1983-09-09 | 1989-09-05 | Berol Kemi Ab | Process for preparing a ruthenium-promoted, halogen-containing nickel and/or cobalt catalyst and a catalyst prepared by the process |
SE461095B (sv) * | 1983-09-09 | 1990-01-08 | Berol Kemi Ab | Amineringsfoerfarande med anvaendning av en ruteniumdopad nickel och/eller kovoltkatalysator |
SE457608B (sv) * | 1986-07-11 | 1989-01-16 | Berol Kemi Ab | Foerfarande foer framstaellning av en ruteniumdopad nickel- och/eller koboltkatalysator paa en poroes metalloxidbaerare samt anvaendning av katalysatorn i en hydrerings- och/eller dehydreringsreaktion |
US4656297A (en) * | 1985-03-11 | 1987-04-07 | Amoco Corporation | Coproduction of butanediol and tetrahydrofuran and their subsequent separation from the reaction product mixture |
US4652685A (en) * | 1985-11-15 | 1987-03-24 | General Electric Company | Hydrogenation of lactones to glycols |
DE3610698A1 (de) * | 1986-03-29 | 1987-10-01 | Henkel Kgaa | Katalysator und verfahren zur katalytischen hydrierung von fettsaeuremethylestern im festbett |
GB8623233D0 (en) * | 1986-09-26 | 1986-10-29 | British Petroleum Co Plc | Syngas conversion catalyst |
US5149680A (en) * | 1987-03-31 | 1992-09-22 | The British Petroleum Company P.L.C. | Platinum group metal alloy catalysts for hydrogenation of carboxylic acids and their anhydrides to alcohols and/or esters |
US4810807A (en) * | 1987-10-13 | 1989-03-07 | The Standard Oil Company | Hydrogenation of maleic anhydride to tetrahydrofuran |
US4827001A (en) * | 1987-11-02 | 1989-05-02 | The Standard Oil Company | Preparation of γ-butyrolactone and 1,4-butanediol by catalytic hydrogenation of maleic acid |
US4885411A (en) * | 1987-11-27 | 1989-12-05 | Gaf Corporation | Hydrogenation process for converting lactones to diols |
GB8811009D0 (en) * | 1988-05-10 | 1988-06-15 | Bp Chem Int Ltd | Chemical process |
JPH075489B2 (ja) * | 1988-05-17 | 1995-01-25 | 三菱化学株式会社 | ジオール及び/又は環状エーテルの製造法 |
JP2596604B2 (ja) * | 1988-12-14 | 1997-04-02 | 東燃株式会社 | 1,4−ブタンジオールおよびテトラヒドロフランの製造方法 |
US5030773A (en) * | 1990-07-25 | 1991-07-09 | General Electric Company | Process for the production of butanediol |
WO1992002298A1 (en) * | 1990-07-27 | 1992-02-20 | E.I. Du Pont De Nemours Company | Hydrogenation catalyst and method for preparing tetrahydrofuran |
US5196602A (en) * | 1991-12-30 | 1993-03-23 | The Standard Oil Company | Two-stage maleic anhydride hydrogenation process for 1,4-butanediol synthesis |
DE4228884A1 (de) * | 1992-08-29 | 1994-03-03 | Basf Ag | Verfahren zur Herstellung von Reduktionsprodukten von Derivaten der 4-Hydroxybuttersäure |
DE10061558A1 (de) * | 2000-12-11 | 2002-06-13 | Basf Ag | Verfahren zur Hydrierung von Maleinsäureanhydrid und verwandten Verbindungen in einem Wirbelschichtreaktor |
US20040030199A1 (en) * | 2002-01-29 | 2004-02-12 | Maughon Robert R. | Process for reducing alpha-haloketones to secondary alpha-haloalcohols |
GB0210143D0 (en) * | 2002-05-02 | 2002-06-12 | Davy Process Techn Ltd | Process |
DE10225927A1 (de) * | 2002-06-11 | 2003-12-24 | Basf Ag | Verfahren zur Herstellung von Butandiol durch kombinierte Gasphasen- und Flüssigphasensynthese |
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DE10225929A1 (de) * | 2002-06-11 | 2003-12-24 | Basf Ag | Zweistufiges Verfahren zur Herstellung von Butandiol mit Zwischenabtrennung von Bernsteinsäureanhydrid |
GB0325526D0 (en) * | 2003-10-31 | 2003-12-03 | Davy Process Techn Ltd | Process |
WO2006067171A1 (en) * | 2004-12-23 | 2006-06-29 | Shell Internationale Research Maatschappij B.V. | A process for the hydrogenation of a lactone or of a carboxylic acid or an ester having a gamma-carbonyl group |
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LT2821494T (lt) | 2007-03-16 | 2017-04-25 | Genomatica, Inc. | 1,4-butandiolio ir jo pirmtakų biosintezės būdai ir kompozicijos |
WO2009045637A2 (en) * | 2007-08-10 | 2009-04-09 | Genomatica, Inc. | Methods for the synthesis of acrylic acid and derivatives from fumaric acid |
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Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2607807A (en) * | 1950-02-24 | 1952-08-19 | Du Pont | Preparation of alcohols from carboxylic acids |
US2772292A (en) * | 1953-07-13 | 1956-11-27 | Du Pont | Hydrogenation of maleic anhydride |
US3055840A (en) * | 1958-01-13 | 1962-09-25 | Engelhard Ind Inc | Ruthenium-containing catalysts and methods of making said catalysts and increasing their activity |
US3370067A (en) * | 1967-04-07 | 1968-02-20 | Shell Oil Co | Hydrogenolysis of butyrolactone and gamma-valerolactone to the corresponding cyclic ethers |
DE1939882A1 (de) * | 1968-08-10 | 1970-02-19 | Mitsubishi Chem Ind | Verfahren zur Herstellung von Ta?rahydrofuran |
DE2715667A1 (de) * | 1977-04-07 | 1978-10-12 | Hoechst Ag | Verfahren zur herstellung von butandiol-(1.4) |
NL7704658A (nl) * | 1977-04-28 | 1978-10-31 | Shell Int Research | Werkwijze voor de bereiding van koolwaterstoffen. |
-
1980
- 1980-12-22 US US06/218,856 patent/US4301077A/en not_active Expired - Fee Related
-
1981
- 1981-08-24 CA CA000384444A patent/CA1157031A/en not_active Expired
- 1981-10-14 JP JP56164882A patent/JPS57109736A/ja active Granted
- 1981-10-29 DE DE8181305152T patent/DE3166724D1/de not_active Expired
- 1981-10-29 EP EP81305152A patent/EP0055512B1/en not_active Expired
- 1981-12-21 KR KR1019810005041A patent/KR880000544B1/ko active
Also Published As
Publication number | Publication date |
---|---|
JPS57109736A (en) | 1982-07-08 |
CA1157031A (en) | 1983-11-15 |
EP0055512B1 (en) | 1984-10-17 |
KR880000544B1 (ko) | 1988-04-13 |
US4301077A (en) | 1981-11-17 |
JPH0459303B2 (ko) | 1992-09-21 |
DE3166724D1 (en) | 1984-11-22 |
EP0055512A1 (en) | 1982-07-07 |
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