JPS6053586A - 光互変性有機組成物 - Google Patents
光互変性有機組成物Info
- Publication number
- JPS6053586A JPS6053586A JP59163457A JP16345784A JPS6053586A JP S6053586 A JPS6053586 A JP S6053586A JP 59163457 A JP59163457 A JP 59163457A JP 16345784 A JP16345784 A JP 16345784A JP S6053586 A JPS6053586 A JP S6053586A
- Authority
- JP
- Japan
- Prior art keywords
- photochromic
- indoline
- oxazine
- trifluoromethyl
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 18
- 229920003023 plastic Polymers 0.000 claims abstract description 17
- 239000004033 plastic Substances 0.000 claims abstract description 15
- 239000000326 ultraviolet stabilizing agent Substances 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 16
- 239000012963 UV stabilizer Substances 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229920006217 cellulose acetate butyrate Polymers 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000005281 excited state Effects 0.000 claims description 4
- LNQMUHQVKMATKD-UHFFFAOYSA-N butan-1-amine;nickel Chemical compound [Ni].CCCCN LNQMUHQVKMATKD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 150000004893 oxazines Chemical class 0.000 claims 2
- 229920005668 polycarbonate resin Polymers 0.000 claims 2
- 239000004431 polycarbonate resin Substances 0.000 claims 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims 1
- JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical group C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 claims 1
- -1 5-tert-butyl-4-hydroxybenzyl Chemical group 0.000 claims 1
- 206010041235 Snoring Diseases 0.000 claims 1
- BAGDYXSZQVQPKH-UHFFFAOYSA-M [Ni+].CC(C)OP([O-])(=S)SC(C)C Chemical compound [Ni+].CC(C)OP([O-])(=S)SC(C)C BAGDYXSZQVQPKH-UHFFFAOYSA-M 0.000 claims 1
- ZVRLGOKQDHVWSZ-UHFFFAOYSA-L cobalt(2+);n,n-di(propan-2-yl)carbamodithioate Chemical compound [Co+2].CC(C)N(C(C)C)C([S-])=S.CC(C)N(C(C)C)C([S-])=S ZVRLGOKQDHVWSZ-UHFFFAOYSA-L 0.000 claims 1
- GWXMDJKGVWQLBZ-UHFFFAOYSA-N di(propan-2-yl)carbamodithioic acid Chemical compound CC(C)N(C(C)C)C(S)=S GWXMDJKGVWQLBZ-UHFFFAOYSA-N 0.000 claims 1
- PNDZEEPOYCVIIY-UHFFFAOYSA-N indo-1 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C=2N=C3[CH]C(=CC=C3C=2)C(O)=O)N(CC(O)=O)CC(O)=O)=C1 PNDZEEPOYCVIIY-UHFFFAOYSA-N 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 239000013110 organic ligand Substances 0.000 claims 1
- 230000000149 penetrating effect Effects 0.000 claims 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims 1
- 239000004926 polymethyl methacrylate Substances 0.000 claims 1
- 239000006228 supernatant Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 21
- 238000002834 transmittance Methods 0.000 abstract description 7
- 125000003003 spiro group Chemical group 0.000 abstract description 4
- 230000007935 neutral effect Effects 0.000 abstract description 3
- 239000000463 material Substances 0.000 description 9
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- 150000007514 bases Chemical class 0.000 description 4
- 230000002452 interceptive effect Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 3
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000000411 transmission spectrum Methods 0.000 description 2
- 101100382321 Caenorhabditis elegans cal-1 gene Proteins 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 238000006783 Fischer indole synthesis reaction Methods 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 229920004142 LEXAN™ Polymers 0.000 description 1
- 239000004418 Lexan Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920005372 Plexiglas® Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 230000003601 intercostal effect Effects 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- 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
- G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Eyeglasses (AREA)
- Optical Filters (AREA)
- Dc Digital Transmission (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US52130983A | 1983-08-08 | 1983-08-08 | |
US521309 | 1983-08-08 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP40824190A Division JPH0617990B2 (ja) | 1990-12-27 | 1990-12-27 | 光互変性プラスティック製品 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6053586A true JPS6053586A (ja) | 1985-03-27 |
JPH0365839B2 JPH0365839B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-10-15 |
Family
ID=24076241
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP59163457A Granted JPS6053586A (ja) | 1983-08-08 | 1984-08-02 | 光互変性有機組成物 |
Country Status (6)
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5017698A (en) * | 1988-07-05 | 1991-05-21 | Kureha Kagaku Kogyo Kabushiki Kaisha | Spirooxazine photochromic compounds |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1246565A (en) * | 1984-07-06 | 1988-12-13 | Shinichi Yamamoto | Spiro-oxazine compounds and preparation thereof and photochronic shaped article |
US4720547A (en) * | 1984-07-30 | 1988-01-19 | Ppg Industries, Inc. | Photochromic compound and articles containing the same |
JPS61120558A (ja) * | 1984-11-15 | 1986-06-07 | Nitsuko Ltd | 呼出し信号送出回路 |
GB2184734A (en) * | 1985-12-19 | 1987-07-01 | Pilkington Brothers Plc | Process for manufacturing photochromic articles |
GB8610709D0 (en) * | 1986-05-01 | 1986-06-04 | Plinkington Bros Plc | Photochromic lenses |
AU616650B2 (en) * | 1987-02-02 | 1991-11-07 | Toray Industries, Inc. | Spirooxazine photochromic compounds and resins |
US5171636A (en) * | 1989-12-12 | 1992-12-15 | Enichem Synthesis S.P.A. | Photochromatic and thermochromatic spiro-oxazepin-oxazine compounds and the process for their preparation |
IT1237528B (it) * | 1989-12-12 | 1993-06-08 | Enichem Sintesi | Composti fotocromatici e termocromatici spiro-ossazepin-ossazine e procedimento per la loro preparazione |
IT1250697B (it) * | 1991-07-24 | 1995-04-21 | Enichem Sintesi | Composti fotocromatici e termocromatici e loro applicazione in materiali polimerici. |
US5531940A (en) * | 1993-12-10 | 1996-07-02 | Innotech, Inc. | Method for manufacturing photochromic lenses |
US5789015A (en) * | 1996-06-26 | 1998-08-04 | Innotech, Inc. | Impregnation of plastic substrates with photochromic additives |
US5914174A (en) * | 1996-12-05 | 1999-06-22 | Innotech, Inc. | Lens or semi-finished blank comprising photochromic resin compositions |
IT1292461B1 (it) * | 1997-07-03 | 1999-02-08 | Great Lakes Chemical Italia | Composti fotocromatici,procedimento per la loro preparazione e loro utilizzo in materiali polimerici |
US6084702A (en) | 1998-10-15 | 2000-07-04 | Pleotint, L.L.C. | Thermochromic devices |
US7077985B2 (en) | 2000-05-30 | 2006-07-18 | Vision-Ease Lens | Injection molding of lens |
US7858001B2 (en) | 2003-09-09 | 2010-12-28 | Insight Equity A.P.X., L.P. | Photochromic lens |
US8298671B2 (en) | 2003-09-09 | 2012-10-30 | Insight Equity, A.P.X, LP | Photochromic polyurethane laminate |
US8002935B2 (en) | 2005-03-04 | 2011-08-23 | Insight Equity A.P.X., L.P. | Forming method for polymeric laminated wafers comprising different film materials |
GB2495505A (en) * | 2011-10-11 | 2013-04-17 | Hd Inspiration Holding B V | Visor with photochromatic insert |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4215010A (en) * | 1978-09-08 | 1980-07-29 | American Optical Corporation | Photochromic compounds |
-
1984
- 1984-04-11 AU AU26743/84A patent/AU565392B2/en not_active Ceased
- 1984-06-20 AT AT84304153T patent/ATE35059T1/de not_active IP Right Cessation
- 1984-06-20 EP EP84304153A patent/EP0134633B1/en not_active Expired
- 1984-06-20 DE DE8484304153T patent/DE3472015D1/de not_active Expired
- 1984-07-02 BR BR8403260A patent/BR8403260A/pt not_active IP Right Cessation
- 1984-08-02 JP JP59163457A patent/JPS6053586A/ja active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5017698A (en) * | 1988-07-05 | 1991-05-21 | Kureha Kagaku Kogyo Kabushiki Kaisha | Spirooxazine photochromic compounds |
Also Published As
Publication number | Publication date |
---|---|
EP0134633B1 (en) | 1988-06-08 |
BR8403260A (pt) | 1985-06-11 |
AU2674384A (en) | 1985-02-14 |
JPH0365839B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-10-15 |
AU565392B2 (en) | 1987-09-17 |
EP0134633A3 (en) | 1986-01-22 |
ATE35059T1 (de) | 1988-06-15 |
EP0134633A2 (en) | 1985-03-20 |
DE3472015D1 (en) | 1988-07-14 |
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