CA2187593A1 - Naphthalenelactamimide fluorescence dyes - Google Patents
Naphthalenelactamimide fluorescence dyesInfo
- Publication number
- CA2187593A1 CA2187593A1 CA002187593A CA2187593A CA2187593A1 CA 2187593 A1 CA2187593 A1 CA 2187593A1 CA 002187593 A CA002187593 A CA 002187593A CA 2187593 A CA2187593 A CA 2187593A CA 2187593 A1 CA2187593 A1 CA 2187593A1
- Authority
- CA
- Canada
- Prior art keywords
- tert
- reaction
- formula
- naphthalenelactamimide
- butylphenyl
- 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.)
- Abandoned
Links
- 239000000975 dye Substances 0.000 title abstract description 25
- -1 2,5-di-tert-butylphenyl Chemical group 0.000 claims abstract description 65
- 238000006243 chemical reaction Methods 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 9
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011368 organic material Substances 0.000 claims abstract description 5
- 239000000990 laser dye Substances 0.000 claims abstract description 3
- 230000003287 optical effect Effects 0.000 claims abstract description 3
- 238000003860 storage Methods 0.000 claims abstract description 3
- 108091008695 photoreceptors Proteins 0.000 claims abstract 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 58
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000004040 coloring Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000002704 decyl group Chemical group [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])* 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000007850 fluorescent dye Substances 0.000 claims description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- JAFHWOGMKFOVFF-UHFFFAOYSA-N 1-amino-2h-naphthalene-1,2,3-tricarboxylic acid Chemical class C1=CC=C2C(N)(C(O)=O)C(C(O)=O)C(C(O)=O)=CC2=C1 JAFHWOGMKFOVFF-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000004043 dyeing Methods 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
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- 239000000243 solution Substances 0.000 description 46
- 229910052757 nitrogen Inorganic materials 0.000 description 44
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- 239000000843 powder Substances 0.000 description 40
- 239000000047 product Substances 0.000 description 35
- 239000011521 glass Substances 0.000 description 32
- 229960000583 acetic acid Drugs 0.000 description 31
- 239000012362 glacial acetic acid Substances 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
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- 238000002844 melting Methods 0.000 description 24
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- 230000008018 melting Effects 0.000 description 22
- 238000009835 boiling Methods 0.000 description 20
- 239000002244 precipitate Substances 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 12
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 241001237728 Precis Species 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000007937 lozenge Substances 0.000 description 9
- 150000003951 lactams Chemical group 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 150000003949 imides Chemical class 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000012505 colouration Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- NUZVLYNISQOZOW-UHFFFAOYSA-N 2,5-ditert-butylaniline Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(N)=C1 NUZVLYNISQOZOW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229920001577 copolymer Polymers 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
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- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- CNPQVEJSVQNWMV-UHFFFAOYSA-N (1-ethylcyclohexyl)methanamine Chemical compound CCC1(CN)CCCCC1 CNPQVEJSVQNWMV-UHFFFAOYSA-N 0.000 description 1
- FBXQBTBVSJWIHD-UHFFFAOYSA-N (1-propylcyclohexyl)methanamine Chemical compound CCCC1(CN)CCCCC1 FBXQBTBVSJWIHD-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SZXBDTIPTMLHFY-UHFFFAOYSA-N 2,2-dihexyloctan-1-amine Chemical compound CCCCCCC(CN)(CCCCCC)CCCCCC SZXBDTIPTMLHFY-UHFFFAOYSA-N 0.000 description 1
- AFYUBCQPUVSMBC-UHFFFAOYSA-N 2,2-dimethylheptan-1-amine Chemical compound CCCCCC(C)(C)CN AFYUBCQPUVSMBC-UHFFFAOYSA-N 0.000 description 1
- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
- KYZMGJACRIPURT-UHFFFAOYSA-N 2-butyl-2-phenylhexan-1-amine Chemical compound CCCCC(CN)(CCCC)C1=CC=CC=C1 KYZMGJACRIPURT-UHFFFAOYSA-N 0.000 description 1
- NQHLVVJKVNCGHU-UHFFFAOYSA-N 2-ethyl-2-phenylbutan-1-amine Chemical compound CCC(CC)(CN)C1=CC=CC=C1 NQHLVVJKVNCGHU-UHFFFAOYSA-N 0.000 description 1
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- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 1
- AEIOZWYBDBVCGW-UHFFFAOYSA-N 2-tert-butylaniline Chemical compound CC(C)(C)C1=CC=CC=C1N AEIOZWYBDBVCGW-UHFFFAOYSA-N 0.000 description 1
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- NCIRWDIUZFVVQQ-UHFFFAOYSA-N 6-tert-butyl-6-methylcyclohexa-2,4-dien-1-amine Chemical compound CC(C)(C)C1(C)C=CC=CC1N NCIRWDIUZFVVQQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Luminescent Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Hybrid Cells (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH288295 | 1995-10-12 | ||
| CH2882/95 | 1995-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2187593A1 true CA2187593A1 (en) | 1997-04-13 |
Family
ID=4243716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002187593A Abandoned CA2187593A1 (en) | 1995-10-12 | 1996-10-10 | Naphthalenelactamimide fluorescence dyes |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5886183A (enExample) |
| EP (1) | EP0769532B1 (enExample) |
| JP (1) | JP4086920B2 (enExample) |
| CA (1) | CA2187593A1 (enExample) |
| DE (1) | DE59608872D1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0630802U (ja) * | 1992-09-11 | 1994-04-22 | 光洋電子工業株式会社 | Ｐｃのユニット間の接続構造 |
| DE19900063A1 (de) * | 1999-01-04 | 2000-07-27 | Heinz Langhals | Naphthalin- und Perylenhydrazamimide - eine neue Klasse von Farbstoffen |
| EP1340755A4 (en) * | 2000-11-14 | 2004-03-17 | Shionogi & Co | AGENT WITH EFFECT AGAINST HELICOBACTER |
| EP1445115A4 (en) * | 2001-10-22 | 2005-02-23 | Mitsui Chemicals Inc | IMIDENCES AND OPTICAL RECORDING MEDIA MANUFACTURED THEREOF |
| WO2003095453A1 (en) * | 2002-05-13 | 2003-11-20 | Shionogi & Co., Ltd. | Compounds against helicobacter activity |
| KR100513700B1 (ko) * | 2003-07-04 | 2005-09-09 | 삼성전자주식회사 | 나프탈렌테트라카르복시디이미드 유도체 및 이를 포함하는전자사진감광체 |
| KR100622371B1 (ko) * | 2003-12-15 | 2006-09-18 | 삼성전자주식회사 | 전자흡인기를 갖는 신규한페닐아조메틸렌-사이클로헥사디에논 유도체 및 이를함유하는 전자사진감광체 |
| DE102004006143A1 (de) * | 2004-02-07 | 2005-08-25 | Wella Ag | Neue Naphthalinderivate und diese Verbindungen enthaltende Färbemittel für Keratinfasern |
| DE102004006142A1 (de) | 2004-02-07 | 2005-08-25 | Wella Ag | Neutrale und kationische Naphthalinderivate und diese Verbindungen enthaltende Färbemittel für Keratinfasern |
| JP4407435B2 (ja) | 2004-09-02 | 2010-02-03 | 富士ゼロックス株式会社 | 電子写真用トナー、その製造方法及び画像形成方法 |
| EP1655359A1 (de) * | 2004-11-06 | 2006-05-10 | Covion Organic Semiconductors GmbH | Organische Elektrolumineszenzvorrichtung |
| DE102005034685A1 (de) * | 2005-07-25 | 2007-02-08 | Langhals, Heinz, Prof. Dr. | Naphthalinamidinimide und Piperazino-Bisimide |
| US7629605B2 (en) * | 2005-10-31 | 2009-12-08 | Eastman Kodak Company | N-type semiconductor materials for thin film transistors |
| TW201026740A (en) * | 2008-11-07 | 2010-07-16 | Basf Se | Organic semiconducting polymers |
| ES2888231T3 (es) * | 2010-09-20 | 2022-01-03 | Sirna Therapeutics Inc | Lípidos catiónicos de bajo peso molecular para el suministro de oligonucleótidos |
| CN103382313B (zh) * | 2013-05-03 | 2015-04-08 | 大连理工大学 | 一种萘酰亚胺荧光染料及其制备和应用 |
| US9812645B2 (en) | 2015-02-13 | 2017-11-07 | Flexterra, Inc. | Perylene-based semiconductors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1126074A (en) * | 1966-02-17 | 1968-09-05 | Ici Ltd | Mass colouration of linear polyesters |
| CH611330A5 (enExample) * | 1973-12-06 | 1979-05-31 | Hoechst Ag | |
| GB1495296A (en) * | 1974-12-31 | 1977-12-14 | Hoechst Ag | 4-amino-1,8-naphthalimide dyestuffs |
| SU559557A1 (ru) * | 1975-09-01 | 1979-01-05 | Предприятие П/Я В-8611 | Замещенные имиды нафтостирил-5,6дикарбоновой кислоты в качестве красителей дл синтетических волокон и способ их получени |
| DE3016764A1 (de) * | 1980-04-30 | 1981-11-05 | Heinz Dr. 5880 Lüdenscheid Langhals | Verfahren zur erhoehung der loeslichkeit aromatischer systeme |
-
1996
- 1996-10-02 EP EP96810656A patent/EP0769532B1/de not_active Expired - Lifetime
- 1996-10-02 DE DE59608872T patent/DE59608872D1/de not_active Expired - Lifetime
- 1996-10-10 CA CA002187593A patent/CA2187593A1/en not_active Abandoned
- 1996-10-11 US US08/729,124 patent/US5886183A/en not_active Expired - Fee Related
- 1996-10-11 JP JP27015896A patent/JP4086920B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH09124960A (ja) | 1997-05-13 |
| DE59608872D1 (de) | 2002-04-18 |
| US5886183A (en) | 1999-03-23 |
| EP0769532A1 (de) | 1997-04-23 |
| JP4086920B2 (ja) | 2008-05-14 |
| EP0769532B1 (de) | 2002-03-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20021010 |