JPS6261582B2 - - Google Patents
Info
- Publication number
- JPS6261582B2 JPS6261582B2 JP59266545A JP26654584A JPS6261582B2 JP S6261582 B2 JPS6261582 B2 JP S6261582B2 JP 59266545 A JP59266545 A JP 59266545A JP 26654584 A JP26654584 A JP 26654584A JP S6261582 B2 JPS6261582 B2 JP S6261582B2
- Authority
- JP
- Japan
- Prior art keywords
- groups
- carbonates
- catalyst
- carbonate
- monovalent
- 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
- -1 aliphatic aromatic carbonates Chemical class 0.000 claims description 46
- 239000003054 catalyst Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 29
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000001931 aliphatic group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 230000003197 catalytic effect Effects 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 150000003606 tin compounds Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 32
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- 238000005809 transesterification reaction Methods 0.000 description 10
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000011968 lewis acid catalyst Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 3
- YCNSGSUGQPDYTK-UHFFFAOYSA-N ethyl phenyl carbonate Chemical compound CCOC(=O)OC1=CC=CC=C1 YCNSGSUGQPDYTK-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- KPJSPBQYZLWYAM-UHFFFAOYSA-N (2,6-dimethylphenyl) ethyl carbonate Chemical compound CCOC(=O)OC1=C(C)C=CC=C1C KPJSPBQYZLWYAM-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- MUCRFDZUHPMASM-UHFFFAOYSA-N bis(2-chlorophenyl) carbonate Chemical compound ClC1=CC=CC=C1OC(=O)OC1=CC=CC=C1Cl MUCRFDZUHPMASM-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 2
- 150000005677 organic carbonates Chemical class 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QRZPLIREDJPIHE-UHFFFAOYSA-N (2-chlorophenyl) ethyl carbonate Chemical compound CCOC(=O)OC1=CC=CC=C1Cl QRZPLIREDJPIHE-UHFFFAOYSA-N 0.000 description 1
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RGCPMRIOBZXXBR-UHFFFAOYSA-N butan-1-olate;dibutyltin(2+) Chemical compound CCCCO[Sn](CCCC)(CCCC)OCCCC RGCPMRIOBZXXBR-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- WSEFLELUOFMQAM-UHFFFAOYSA-N chloro phenyl carbonate Chemical compound ClOC(=O)OC1=CC=CC=C1 WSEFLELUOFMQAM-UHFFFAOYSA-N 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/565,888 US4554110A (en) | 1983-12-27 | 1983-12-27 | Process for the preparation of aromatic carbonates |
| US565888 | 1983-12-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60169444A JPS60169444A (ja) | 1985-09-02 |
| JPS6261582B2 true JPS6261582B2 (https=) | 1987-12-22 |
Family
ID=24260535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59266545A Granted JPS60169444A (ja) | 1983-12-27 | 1984-12-19 | 芳香族カ−ボネ−トの改良製造方法 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4554110A (https=) |
| JP (1) | JPS60169444A (https=) |
| DE (1) | DE3445552A1 (https=) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5166393A (en) * | 1987-10-05 | 1992-11-24 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing diaryl carbonate |
| JP2569351B2 (ja) * | 1988-04-16 | 1997-01-08 | 三井石油化学工業株式会社 | 芳香族カーボネート化合物を製造する方法 |
| US5034557A (en) * | 1988-04-16 | 1991-07-23 | Mitsui Petrochemical Industries, Ltd. | Process for production of aromatic carbonate compound |
| JP2540590B2 (ja) * | 1988-04-16 | 1996-10-02 | 三井石油化学工業株式会社 | 芳香族カ―ボネ―ト化合物を製造する方法 |
| DE4006520A1 (de) * | 1990-03-02 | 1991-09-05 | Bayer Ag | Verfahren zur herstellung von mindestens eine aromatische estergruppe enthaltenden kohlensaeurediestern |
| US5221761A (en) * | 1992-04-29 | 1993-06-22 | Instituto Guido Donegani | Melt transesterification process for the production of polycarbonates |
| DE4226756A1 (de) * | 1992-08-13 | 1994-02-17 | Bayer Ag | Verfahren zur Herstellung von Dicarbonaten |
| IT1282363B1 (it) | 1996-01-16 | 1998-03-20 | Enichem Spa | Procedimento continuo per la preparazione di fenil metil carbonato |
| US5770672A (en) * | 1997-04-03 | 1998-06-23 | Elf Atochem North America, Inc. | Catalyst for low temperature cure of blocked isocyanates |
| CA2207146A1 (en) * | 1996-05-28 | 1997-11-28 | Atofina Chemicals, Inc. | Catalyst for low temperature cure of blocked isocyanates |
| US6093842A (en) * | 1998-09-25 | 2000-07-25 | General Electric Company | Process for continuous production of carbonate esters |
| US6600061B1 (en) | 2000-11-15 | 2003-07-29 | General Electric Company | Method for the continuous production of aromatic carbonates |
| CN1628090A (zh) * | 2002-02-05 | 2005-06-15 | Lg化学株式会社 | 使用非均相催化剂制备芳香族碳酸酯的连续方法及其反应设备 |
| CA2566880C (en) * | 2004-05-19 | 2012-04-24 | Asahi Kasei Chemicals Corporation | Process for production of alkyltin alkoxides |
| EA011129B1 (ru) | 2004-06-14 | 2008-12-30 | Асахи Касеи Кемикалз Корпорейшн | Способ получения высококачественного ароматического поликарбоната |
| JP5014787B2 (ja) | 2004-06-17 | 2012-08-29 | 旭化成ケミカルズ株式会社 | 芳香族カーボネートの製造方法 |
| EP1762560A4 (en) * | 2004-06-25 | 2008-05-07 | Asahi Kasei Chemicals Corp | PROCESS FOR PRODUCING AROMATIC CARBONATE AT THE INDUSTRIAL SCALE |
| US20080221348A1 (en) * | 2004-06-25 | 2008-09-11 | Asahi Kasei Chemicals Corporation | Industrial Process for Production of Aromatic Carbonate |
| WO2006006566A1 (ja) * | 2004-07-13 | 2006-01-19 | Asahi Kasei Chemicals Corporation | 芳香族カーボネート類の工業的製造法 |
| CN100543006C (zh) * | 2004-07-14 | 2009-09-23 | 旭化成化学株式会社 | 芳香族碳酸酯类的工业制备方法 |
| JP4292210B2 (ja) * | 2004-08-25 | 2009-07-08 | 旭化成ケミカルズ株式会社 | 高純度ジフェニルカーボネートの工業的製造方法 |
| EP1787977A4 (en) * | 2004-09-02 | 2008-08-06 | Asahi Kasei Chemicals Corp | METHOD FOR THE PRODUCTION OF HIGH-PURITY DIPHENYLCARBONATE IN INDUSTRIAL STANDARD |
| JP4292211B2 (ja) * | 2004-09-03 | 2009-07-08 | 旭化成ケミカルズ株式会社 | 高純度ジアリールカーボネートの工業的製造方法 |
| EA009624B1 (ru) | 2004-09-17 | 2008-02-28 | Асахи Касеи Кемикалз Корпорейшн | Промышленный способ выделения побочно полученных спиртов |
| CN100554242C (zh) * | 2004-09-21 | 2009-10-28 | 旭化成化学株式会社 | 醇类副产物的工业分离方法 |
| JP4229395B2 (ja) * | 2004-09-27 | 2009-02-25 | 旭化成ケミカルズ株式会社 | 芳香族カーボネートの工業的製造方法 |
| US7622601B2 (en) | 2004-10-14 | 2009-11-24 | Asahi Kasei Chemicals Corporation | Process for production of high-purity diaryl carbonate |
| TWI321561B (en) * | 2004-12-21 | 2010-03-11 | Asahi Kasei Chemicals Corp | Method for producing aromatic carbonate |
| BRPI0519103B1 (pt) * | 2004-12-24 | 2015-09-22 | Asahi Kasei Chemicals Corp | Processo para a produção de um carbonato aromático |
| US7378540B2 (en) * | 2005-10-21 | 2008-05-27 | Catalytic Distillation Technologies | Process for producing organic carbonates |
| KR101527236B1 (ko) * | 2007-01-23 | 2015-06-16 | 셀 인터나쵸나아레 레사아치 마아츠샤피 비이부이 | 디아릴 카보네이트의 제조방법 |
| EP1995233A3 (de) * | 2007-05-25 | 2010-06-02 | Bayer MaterialScience AG | Verfahren zur Herstellung von Diaryl- oder Arylalkylcarbonaten aus Dialkylcarbonaten |
| DE102007044033A1 (de) | 2007-09-14 | 2009-03-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diaryl- oder Alkylarylcarbonaten aus Dialkylcarbonaten |
| DE102007055266A1 (de) | 2007-11-20 | 2009-05-28 | Bayer Materialscience Ag | Verfahren zur Reinigung von Diarylcarbonaten |
| US8110698B2 (en) * | 2008-02-11 | 2012-02-07 | Shell Oil Company | Process for producing diphenyl carbonate |
| US7851645B2 (en) | 2008-02-11 | 2010-12-14 | Catalytic Distillation Technologies | Process for continuous production of organic carbonates or organic carbamates and solid catalysts therefore |
| DE102008029514A1 (de) * | 2008-06-21 | 2009-12-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diarylcarbonaten aus Dialkylcarbonaten |
| DE102009016853A1 (de) * | 2009-04-08 | 2010-10-14 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diaryl- oder Alkylarylcarbonaten aus Dialkylcarbonaten |
| DE102009030680A1 (de) * | 2009-06-26 | 2010-12-30 | Bayer Materialscience Ag | Verfahren zur Herstellung von Dialkylcarbonaten aus Alkylencarbonaten und Alkoholen |
| DE102009053370A1 (de) | 2009-11-14 | 2011-05-19 | Bayer Materialscience Ag | Verfahren zur Reinigung von Dialkylcarbonaten |
| DE102010042937A1 (de) | 2010-10-08 | 2012-04-12 | Bayer Materialscience Aktiengesellschaft | Verfahren zur Herstellung von Diarylcarbonaten aus Dialkylcarbonaten |
| EP2650278A1 (de) | 2012-04-11 | 2013-10-16 | Bayer MaterialScience AG | Verfahren zur Herstellung von Diarylcarbonaten aus Dialkylcarbonaten |
| EP2711353B1 (en) | 2012-09-20 | 2018-10-31 | SABIC Global Technologies B.V. | Process for the continuous manufacture of aryl alkyl carbonate and diaryl carbonate using vapor recompression |
| EP2935197B1 (de) | 2012-12-18 | 2017-07-12 | Covestro Deutschland AG | Verfahren zur herstellung von diarylcarbonat |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3376329A (en) * | 1965-03-31 | 1968-04-02 | Ethyl Corp | Preparation of dialkyltin oxides |
| US3466311A (en) * | 1966-07-18 | 1969-09-09 | Nitto Kasei Co Ltd | Preparation of dialkyltin oxides |
| US3493592A (en) * | 1968-01-15 | 1970-02-03 | Ethyl Corp | Preparation of dialkyltins and dialkyltin oxides |
| US3853960A (en) * | 1970-07-13 | 1974-12-10 | Proctor Chem Co Inc | Process for the manufacture of penthaerythritol tetracarbamate |
| US4182726A (en) * | 1974-06-25 | 1980-01-08 | Snamprogetti, S.P.A. | Process for the preparation of aromatic carbonates |
-
1983
- 1983-12-27 US US06/565,888 patent/US4554110A/en not_active Expired - Fee Related
-
1984
- 1984-12-14 DE DE19843445552 patent/DE3445552A1/de not_active Withdrawn
- 1984-12-19 JP JP59266545A patent/JPS60169444A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60169444A (ja) | 1985-09-02 |
| US4554110A (en) | 1985-11-19 |
| DE3445552A1 (de) | 1985-07-04 |
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