JPS6052150B2 - フオトクロ−ム化合物の製造方法 - Google Patents
フオトクロ−ム化合物の製造方法Info
- Publication number
- JPS6052150B2 JPS6052150B2 JP8999575A JP8999575A JPS6052150B2 JP S6052150 B2 JPS6052150 B2 JP S6052150B2 JP 8999575 A JP8999575 A JP 8999575A JP 8999575 A JP8999575 A JP 8999575A JP S6052150 B2 JPS6052150 B2 JP S6052150B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl
- aryl
- tables
- group
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000003158 alcohol group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 17
- 150000003443 succinic acid derivatives Chemical class 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- -1 α-methylbenzyl group Chemical group 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 7
- 239000012346 acetyl chloride Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- FSUBDXPWXDGTBG-UHFFFAOYSA-N diethyl 2-propan-2-ylidenebutanedioate Chemical compound CCOC(=O)CC(=C(C)C)C(=O)OCC FSUBDXPWXDGTBG-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- KBSVBCHYXYXDAG-UHFFFAOYSA-N 3-acetyl-2,5-dimethylfuran Chemical compound CC(=O)C=1C=C(C)OC=1C KBSVBCHYXYXDAG-UHFFFAOYSA-N 0.000 description 3
- BIPOZVSHXBLJEM-UHFFFAOYSA-N 3-propan-2-ylideneoxolane-2,5-dione Chemical compound CC(C)=C1CC(=O)OC1=O BIPOZVSHXBLJEM-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N 2,5-dimethylfuran Chemical compound CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 238000006600 Stobbe condensation reaction Methods 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- ROUMXZWOBYHRDP-UHFFFAOYSA-N 1-(2-benzyl-1-benzofuran-3-yl)ethanone Chemical compound O1C2=CC=CC=C2C(C(=O)C)=C1CC1=CC=CC=C1 ROUMXZWOBYHRDP-UHFFFAOYSA-N 0.000 description 1
- MZVBMFAXOBHFID-UHFFFAOYSA-N 1-(2-methylfuran-3-yl)ethanone Chemical compound CC(=O)C=1C=COC=1C MZVBMFAXOBHFID-UHFFFAOYSA-N 0.000 description 1
- GEWUQBNPISFMAY-UHFFFAOYSA-N 1-phenyl-3-propan-2-ylidenepyrrolidine-2,5-dione Chemical compound O=C1C(=C(C)C)CC(=O)N1C1=CC=CC=C1 GEWUQBNPISFMAY-UHFFFAOYSA-N 0.000 description 1
- WQNHWIYLCRZRLR-UHFFFAOYSA-N 2-(3-hydroxy-2,5-dioxooxolan-3-yl)acetic acid Chemical compound OC(=O)CC1(O)CC(=O)OC1=O WQNHWIYLCRZRLR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- PUSJAEJRDNPYKM-UHFFFAOYSA-N 3-Acetyl-2,5-dimethylthiophene Chemical compound CC(=O)C=1C=C(C)SC=1C PUSJAEJRDNPYKM-UHFFFAOYSA-N 0.000 description 1
- NAFBSTVYWJYRKC-UHFFFAOYSA-N 3-benzhydrylideneoxolane-2,5-dione Chemical compound O=C1OC(=O)CC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 NAFBSTVYWJYRKC-UHFFFAOYSA-N 0.000 description 1
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 1
- LVHYJQFWIQEHID-UHFFFAOYSA-N 4-amino-4-oxobutanoic acid Chemical compound C(CCC(=O)N)(=O)O.C(CCC(=O)O)(=O)N LVHYJQFWIQEHID-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical group CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- NVTWPJFSDSONBX-UHFFFAOYSA-N C(C)(C)=C1C(=O)N(C(C1)=O)C1=CC=C(C=C1)OC Chemical compound C(C)(C)=C1C(=O)N(C(C1)=O)C1=CC=C(C=C1)OC NVTWPJFSDSONBX-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- AQAGLGRUHUYCPH-UHFFFAOYSA-N diethyl 2-benzhydrylidenebutanedioate Chemical compound C=1C=CC=CC=1C(=C(C(=O)OCC)CC(=O)OCC)C1=CC=CC=C1 AQAGLGRUHUYCPH-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
Classifications
-
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Furan Compounds (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33719/74 | 1974-07-31 | ||
| GB3371974A GB1464603A (en) | 1974-07-31 | 1974-07-31 | Substituted organic photochromic compounds and processes for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5136449A JPS5136449A (ja) | 1976-03-27 |
| JPS6052150B2 true JPS6052150B2 (ja) | 1985-11-18 |
Family
ID=10356577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8999575A Expired JPS6052150B2 (ja) | 1974-07-31 | 1975-07-23 | フオトクロ−ム化合物の製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS6052150B2 (enExample) |
| DE (1) | DE2532224C2 (enExample) |
| FR (1) | FR2280637A1 (enExample) |
| GB (1) | GB1464603A (enExample) |
| IT (1) | IT1046887B (enExample) |
| NL (1) | NL7508987A (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220708A (en) * | 1977-07-22 | 1980-09-02 | Heller Harold G | Photochromic compounds |
| GB1600615A (en) * | 1977-10-28 | 1981-10-21 | Plessey Co Ltd | Photochromic compounds |
| GB2104504B (en) * | 1981-07-16 | 1985-05-09 | English Clays Lovering Pochin | Stabilisation of photochromic fulgides and fulgimides |
| KR850002328A (ko) * | 1983-09-07 | 1985-05-10 | 알. 니콜슨 | 가변색 화합물과 그 제조방법 및 이를 이용한 가변색 렌즈 |
| JPS60160563A (ja) * | 1984-01-18 | 1985-08-22 | Toshiba Battery Co Ltd | 非水電解液電池用正極の製造法 |
| JPS60198053A (ja) * | 1984-02-23 | 1985-10-07 | Toshiba Battery Co Ltd | 非水電解液電池用正極の製造方法 |
| GB8501779D0 (en) * | 1985-01-24 | 1985-02-27 | Plessey Co Plc | Photochromic 3-pyrryl fulgides |
| GB8613420D0 (en) * | 1986-06-03 | 1986-07-09 | Plessey Co Plc | Photochromic gamma butyrolactones |
| EP0239376A3 (en) * | 1986-03-27 | 1988-05-11 | Gec-Marconi Limited | Contrast enhanced photolithography |
| JPS62242677A (ja) * | 1986-04-16 | 1987-10-23 | Agency Of Ind Science & Technol | フォトクロミック材料 |
| JPS63101374A (ja) * | 1986-10-17 | 1988-05-06 | Agency Of Ind Science & Technol | フオトクロミツク材料の中間物 |
| GB8620430D0 (en) * | 1986-08-22 | 1986-10-01 | Plessey Co Plc | Marking of articles |
| DE4007636A1 (de) * | 1990-03-10 | 1991-09-12 | Basf Ag | Photochrome monomere und hieraus hergestellte photochrome polymerisate |
| US9164480B2 (en) * | 2006-12-14 | 2015-10-20 | General Electric Company | Holographic data storage device and method of making |
-
1974
- 1974-07-31 GB GB3371974A patent/GB1464603A/en not_active Expired
-
1975
- 1975-07-18 DE DE19752532224 patent/DE2532224C2/de not_active Expired
- 1975-07-23 JP JP8999575A patent/JPS6052150B2/ja not_active Expired
- 1975-07-23 IT IT2569275A patent/IT1046887B/it active
- 1975-07-24 FR FR7523123A patent/FR2280637A1/fr active Granted
- 1975-07-28 NL NL7508987A patent/NL7508987A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5136449A (ja) | 1976-03-27 |
| FR2280637B1 (enExample) | 1980-03-07 |
| FR2280637A1 (fr) | 1976-02-27 |
| DE2532224C2 (de) | 1986-03-06 |
| DE2532224A1 (de) | 1976-02-12 |
| GB1464603A (en) | 1977-02-16 |
| IT1046887B (it) | 1980-07-31 |
| NL7508987A (nl) | 1976-02-03 |
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