JPH0430386B2 - - Google Patents
Info
- Publication number
- JPH0430386B2 JPH0430386B2 JP59009856A JP985684A JPH0430386B2 JP H0430386 B2 JPH0430386 B2 JP H0430386B2 JP 59009856 A JP59009856 A JP 59009856A JP 985684 A JP985684 A JP 985684A JP H0430386 B2 JPH0430386 B2 JP H0430386B2
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- reaction
- stirring
- added
- reaction mixture
- 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
- 150000001639 boron compounds Chemical class 0.000 claims description 12
- 239000005749 Copper compound Substances 0.000 claims description 9
- 150000001880 copper compounds Chemical class 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000006471 dimerization reaction Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 description 31
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 27
- 238000000034 method Methods 0.000 description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
- 239000001301 oxygen Substances 0.000 description 15
- 229910052760 oxygen Inorganic materials 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 14
- 239000007789 gas Substances 0.000 description 14
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 13
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- -1 copper amine Chemical class 0.000 description 9
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 7
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 229940076286 cupric acetate Drugs 0.000 description 6
- 229910021538 borax Inorganic materials 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000010813 internal standard method Methods 0.000 description 5
- 239000004328 sodium tetraborate Substances 0.000 description 5
- 235000010339 sodium tetraborate Nutrition 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229920006380 polyphenylene oxide Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000002798 spectrophotometry method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- WCUDDVOHXLKLQN-UHFFFAOYSA-N 2,3,6-triethylphenol Chemical compound CCC1=CC=C(CC)C(CC)=C1O WCUDDVOHXLKLQN-UHFFFAOYSA-N 0.000 description 1
- JRPBSTGRRSTANR-UHFFFAOYSA-N 2,6-bis(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=CC(CC(C)C)=C1O JRPBSTGRRSTANR-UHFFFAOYSA-N 0.000 description 1
- FHTGJZOULSYEOB-UHFFFAOYSA-N 2,6-di(butan-2-yl)phenol Chemical compound CCC(C)C1=CC=CC(C(C)CC)=C1O FHTGJZOULSYEOB-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- METWAQRCMRWDAW-UHFFFAOYSA-N 2,6-diethylphenol Chemical compound CCC1=CC=CC(CC)=C1O METWAQRCMRWDAW-UHFFFAOYSA-N 0.000 description 1
- UHZLTTPUIQXNPO-UHFFFAOYSA-N 2,6-ditert-butyl-3-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1C(C)(C)C UHZLTTPUIQXNPO-UHFFFAOYSA-N 0.000 description 1
- KUNNUNBSGQSGDY-UHFFFAOYSA-N 2-butyl-6-methylphenol Chemical compound CCCCC1=CC=CC(C)=C1O KUNNUNBSGQSGDY-UHFFFAOYSA-N 0.000 description 1
- YCUALLYXPZGZFN-UHFFFAOYSA-N 2-cyclohexyl-6-methylphenol Chemical compound CC1=CC=CC(C2CCCCC2)=C1O YCUALLYXPZGZFN-UHFFFAOYSA-N 0.000 description 1
- LQIUMIRFHFVMRI-UHFFFAOYSA-N 2-dodecyl-6-(2-methylpropyl)phenol Chemical compound CCCCCCCCCCCCC1=CC=CC(CC(C)C)=C1O LQIUMIRFHFVMRI-UHFFFAOYSA-N 0.000 description 1
- ULLJOEOHPLSIJP-UHFFFAOYSA-N 2-methyl-6-octylphenol Chemical compound CCCCCCCCC1=CC=CC(C)=C1O ULLJOEOHPLSIJP-UHFFFAOYSA-N 0.000 description 1
- NNJLCFALHMMXIR-UHFFFAOYSA-N 6-tert-butyl-2,3-diethylphenol Chemical compound CCC1=CC=C(C(C)(C)C)C(O)=C1CC NNJLCFALHMMXIR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- PSHMSSXLYVAENJ-UHFFFAOYSA-N dilithium;[oxido(oxoboranyloxy)boranyl]oxy-oxoboranyloxyborinate Chemical compound [Li+].[Li+].O=BOB([O-])OB([O-])OB=O PSHMSSXLYVAENJ-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052731 fluorine Chemical group 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- HZRMTWQRDMYLNW-UHFFFAOYSA-N lithium metaborate Chemical compound [Li+].[O-]B=O HZRMTWQRDMYLNW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59009856A JPS60152433A (ja) | 1984-01-23 | 1984-01-23 | ４，４′−ジヒドロキシジフエニル類の製造法 |
| US06/690,614 US4564713A (en) | 1984-01-23 | 1985-01-11 | Process for producing 4,4'-dihydroxydiphenyls |
| DE8585300393T DE3569366D1 (en) | 1984-01-23 | 1985-01-21 | Process for producing 4,4'-dihydroxydiphenyls |
| EP85300393A EP0150967B1 (en) | 1984-01-23 | 1985-01-21 | Process for producing 4,4'-dihydroxydiphenyls |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59009856A JPS60152433A (ja) | 1984-01-23 | 1984-01-23 | ４，４′−ジヒドロキシジフエニル類の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60152433A JPS60152433A (ja) | 1985-08-10 |
| JPH0430386B2 true JPH0430386B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-05-21 |
Family
ID=11731773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59009856A Granted JPS60152433A (ja) | 1984-01-23 | 1984-01-23 | ４，４′−ジヒドロキシジフエニル類の製造法 |
Country Status (4)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63119432A (ja) * | 1986-11-07 | 1988-05-24 | Kureha Chem Ind Co Ltd | ４，４′−ジヒドロキシビフエニルの製造方法 |
| JP2003096009A (ja) * | 2001-09-27 | 2003-04-03 | Sumitomo Chem Co Ltd | ビフェニル化合物の製造法 |
| KR100914020B1 (ko) * | 2001-10-17 | 2009-08-28 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 이작용성 바이페닐 및 이를 이용한 이작용성 페닐렌에테르올리고머 화합물의 제조방법 |
| JP2005002351A (ja) * | 2004-08-13 | 2005-01-06 | Japan Epoxy Resin Kk | 半導体封止用硬化性エポキシ樹脂組成物 |
| CN106831350A (zh) * | 2017-02-12 | 2017-06-13 | 湘潭大学 | 一种合成高纯3,3’,5,5’‑四甲基‑4,4’‑联苯二酚的方法 |
| CN110105176B (zh) * | 2019-05-30 | 2022-03-25 | 甘肃泰升化工科技有限公司 | 一种tmbp工业合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4130504A (en) * | 1974-08-23 | 1978-12-19 | Ici Americas Inc. | Oxidative coupling of phenols and naphthols |
| US4085124A (en) * | 1975-11-24 | 1978-04-18 | Ici Americas Inc. | Oxidative coupling of alkylphenols, alkoxyphenols and 1-naphthols catalyzed by metal complexes of amino compounds |
| US4132722A (en) * | 1976-11-26 | 1979-01-02 | Ici Americas Inc. | Oxidative coupling of alkylphenols catalyzed by metal complexes of diimino acid |
| US4100205A (en) * | 1977-02-18 | 1978-07-11 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of aminoketo compounds |
| US4256596A (en) * | 1978-08-07 | 1981-03-17 | The Lubrizol Corporation | Oxidatively coupled hydroxyaromatic compounds and fuels and lubricants containing them |
| US4238627A (en) * | 1978-11-16 | 1980-12-09 | Union Carbide Corporation | Oxidative process for preparing substituted biphenols |
| US4180686A (en) * | 1979-01-25 | 1979-12-25 | Conoco, Inc. | Oxidative coupling of alkylphenols |
| US4195189A (en) * | 1979-02-15 | 1980-03-25 | Ici Americas Inc. | Preparation of biphenols by the oxidative coupling of alkylphenols |
| US4438284A (en) * | 1981-03-09 | 1984-03-20 | The Dow Chemical Company | Catalysts for oxidative coupling of phenols |
| US4354048A (en) * | 1981-05-22 | 1982-10-12 | The Dow Chemical Company | Copper chromite catalysts for oxidative coupling of phenols |
-
1984
- 1984-01-23 JP JP59009856A patent/JPS60152433A/ja active Granted
-
1985
- 1985-01-11 US US06/690,614 patent/US4564713A/en not_active Expired - Lifetime
- 1985-01-21 DE DE8585300393T patent/DE3569366D1/de not_active Expired
- 1985-01-21 EP EP85300393A patent/EP0150967B1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3569366D1 (en) | 1989-05-18 |
| EP0150967A2 (en) | 1985-08-07 |
| JPS60152433A (ja) | 1985-08-10 |
| US4564713A (en) | 1986-01-14 |
| EP0150967B1 (en) | 1989-04-12 |
| EP0150967A3 (en) | 1987-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |