JPS58128328A - ビス（ｐ−アルキルフエニルエチニル）アントラセン - Google Patents
ビス（ｐ−アルキルフエニルエチニル）アントラセンInfo
- Publication number
- JPS58128328A JPS58128328A JP58004277A JP427783A JPS58128328A JP S58128328 A JPS58128328 A JP S58128328A JP 58004277 A JP58004277 A JP 58004277A JP 427783 A JP427783 A JP 427783A JP S58128328 A JPS58128328 A JP S58128328A
- Authority
- JP
- Japan
- Prior art keywords
- chemiluminescence
- peroxide
- compound
- bis
- 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.)
- Granted
Links
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title claims description 12
- 239000000203 mixture Substances 0.000 claims description 36
- 150000002978 peroxides Chemical class 0.000 claims description 26
- 239000000376 reactant Substances 0.000 claims description 16
- 239000007850 fluorescent dye Substances 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Substances OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 11
- -1 phenylethynyl Chemical group 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- DYZYNUQMTZWZAO-UHFFFAOYSA-N 1-(2-phenylethynyl)anthracene Chemical compound C1=CC=CC=C1C#CC1=CC=CC2=CC3=CC=CC=C3C=C12 DYZYNUQMTZWZAO-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical class [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006862 quantum yield reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 2
- 229960001826 dimethylphthalate Drugs 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229960004025 sodium salicylate Drugs 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 102100022717 Atypical chemokine receptor 1 Human genes 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101100130497 Drosophila melanogaster Mical gene Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101000678879 Homo sapiens Atypical chemokine receptor 1 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
- 241001474791 Proboscis Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- PEYVWSJAZONVQK-UHFFFAOYSA-N hydroperoxy(oxo)borane Chemical compound OOB=O PEYVWSJAZONVQK-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C09K11/07—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials having chemically interreactive components, e.g. reactive chemiluminescent compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
- C07C15/60—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing three rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Luminescent Compositions (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/341,390 US4401585A (en) | 1982-01-21 | 1982-01-21 | Bis(p-alkylphenylethynyl)anthracene |
| US341390 | 1982-01-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58128328A true JPS58128328A (ja) | 1983-07-30 |
| JPH0322852B2 JPH0322852B2 (enExample) | 1991-03-27 |
Family
ID=23337350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58004277A Granted JPS58128328A (ja) | 1982-01-21 | 1983-01-17 | ビス（ｐ−アルキルフエニルエチニル）アントラセン |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4401585A (enExample) |
| EP (1) | EP0084599B1 (enExample) |
| JP (1) | JPS58128328A (enExample) |
| KR (1) | KR900003429B1 (enExample) |
| AT (1) | ATE13313T1 (enExample) |
| CA (1) | CA1173864A (enExample) |
| DE (1) | DE3263554D1 (enExample) |
| ES (1) | ES519044A0 (enExample) |
| GB (1) | GB2113709B (enExample) |
| HK (1) | HK39089A (enExample) |
| IL (1) | IL66948A0 (enExample) |
| NO (1) | NO155879C (enExample) |
| SG (1) | SG86688G (enExample) |
| ZA (1) | ZA83397B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01124397A (ja) * | 1987-11-09 | 1989-05-17 | Teijin Ltd | アスペルギルスに対するヒト・モノクローナル抗体とその製造法 |
| JPH04164038A (ja) * | 1990-10-29 | 1992-06-09 | Yamamoto Chem Inc | アントラセン誘導体 |
| JP2004083481A (ja) * | 2002-08-27 | 2004-03-18 | Canon Inc | フルオレン化合物及びそれを用いた有機発光素子 |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3362697D1 (de) * | 1982-10-25 | 1986-04-30 | American Cyanamid Co | 9,10-bis(phenylethynyl)-anthracenes |
| US4655969A (en) * | 1985-04-03 | 1987-04-07 | Richter Herbert P | Chemiluminescent systems |
| US4626383A (en) * | 1985-04-03 | 1986-12-02 | The United States Of America As Represented By The Secretary Of The Navy | Chemiluminescent system catalysts |
| US4717511A (en) * | 1985-12-26 | 1988-01-05 | American Cyanamid Company | Chemiluminescent composition |
| US4698183A (en) * | 1986-02-04 | 1987-10-06 | American Cyanamid Company | High light output-short duration chemiluminescent compositions |
| US5597517A (en) * | 1996-04-30 | 1997-01-28 | Jame Fine Chemicals, Inc. | Two-component chemiluminescent composition |
| US6852429B1 (en) | 2003-08-06 | 2005-02-08 | Canon Kabushiki Kaisha | Organic electroluminescent device based on pyrene derivatives |
| US7195829B2 (en) | 2004-03-30 | 2007-03-27 | Eastman Kodak Company | Organic element for electroluminescent devices |
| US20060214141A1 (en) * | 2005-03-23 | 2006-09-28 | Yankielun Norbert E | Luminescent illumination adjunct for night vision |
| US20080128666A1 (en) * | 2005-12-13 | 2008-06-05 | Crayola, Llc | Chemiluminescent system |
| US20070134513A1 (en) * | 2005-12-13 | 2007-06-14 | Binney & Smith | Chemiluminescent system |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3729426A (en) * | 1970-04-20 | 1973-04-24 | American Cyanamid Co | Chemiluminescent fluorescer comprising phenylethynyl substituted organic compounds |
| US3888786A (en) * | 1972-06-12 | 1975-06-10 | American Cyanamid Co | Chlorinated bis(phenylethynyl)anthracenes as fluorescers in chemiluminescent systems |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3557233A (en) * | 1968-03-14 | 1971-01-19 | American Cyanamid Co | Aromatic hydrocarbons substituted by phenylethynyl groups |
| SE369187B (enExample) * | 1969-04-07 | 1974-08-12 | American Cyanamid Co | |
| CA1015555A (en) * | 1972-06-12 | 1977-08-16 | American Cyanamid Company | Chlorinated bis(phenylethynyl)anthracenes as fluorescers in chemiluminescent systems |
| US4076645A (en) * | 1977-01-10 | 1978-02-28 | American Cyanamid Company | Chemical lighting process and composition |
-
1982
- 1982-01-21 US US06/341,390 patent/US4401585A/en not_active Expired - Fee Related
- 1982-09-30 DE DE8282109051T patent/DE3263554D1/de not_active Expired
- 1982-09-30 AT AT82109051T patent/ATE13313T1/de active
- 1982-09-30 EP EP82109051A patent/EP0084599B1/en not_active Expired
- 1982-10-07 CA CA000413070A patent/CA1173864A/en not_active Expired
- 1982-10-08 IL IL66948A patent/IL66948A0/xx not_active IP Right Cessation
- 1982-10-22 GB GB08230188A patent/GB2113709B/en not_active Expired
- 1982-12-24 KR KR8205797A patent/KR900003429B1/ko not_active Expired
-
1983
- 1983-01-17 ES ES519044A patent/ES519044A0/es active Granted
- 1983-01-17 JP JP58004277A patent/JPS58128328A/ja active Granted
- 1983-01-20 NO NO830181A patent/NO155879C/no unknown
- 1983-01-20 ZA ZA83397A patent/ZA83397B/xx unknown
-
1988
- 1988-12-08 SG SG866/88A patent/SG86688G/en unknown
-
1989
- 1989-05-11 HK HK390/89A patent/HK39089A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3729426A (en) * | 1970-04-20 | 1973-04-24 | American Cyanamid Co | Chemiluminescent fluorescer comprising phenylethynyl substituted organic compounds |
| US3888786A (en) * | 1972-06-12 | 1975-06-10 | American Cyanamid Co | Chlorinated bis(phenylethynyl)anthracenes as fluorescers in chemiluminescent systems |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01124397A (ja) * | 1987-11-09 | 1989-05-17 | Teijin Ltd | アスペルギルスに対するヒト・モノクローナル抗体とその製造法 |
| JPH04164038A (ja) * | 1990-10-29 | 1992-06-09 | Yamamoto Chem Inc | アントラセン誘導体 |
| JP2004083481A (ja) * | 2002-08-27 | 2004-03-18 | Canon Inc | フルオレン化合物及びそれを用いた有機発光素子 |
| US7241513B2 (en) | 2002-08-27 | 2007-07-10 | Canon Kabushiki Kaisha | Fluorene compound and organic luminescent device using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8501431A1 (es) | 1984-12-16 |
| KR840002887A (ko) | 1984-07-21 |
| GB2113709B (en) | 1986-06-11 |
| KR900003429B1 (ko) | 1990-05-18 |
| HK39089A (en) | 1989-05-19 |
| ZA83397B (en) | 1983-10-26 |
| ES519044A0 (es) | 1984-12-16 |
| ATE13313T1 (de) | 1985-06-15 |
| SG86688G (en) | 1989-05-26 |
| EP0084599B1 (en) | 1985-05-15 |
| US4401585A (en) | 1983-08-30 |
| NO155879C (no) | 1987-06-17 |
| JPH0322852B2 (enExample) | 1991-03-27 |
| DE3263554D1 (en) | 1985-06-20 |
| IL66948A0 (en) | 1983-02-23 |
| NO830181L (no) | 1983-07-22 |
| GB2113709A (en) | 1983-08-10 |
| CA1173864A (en) | 1984-09-04 |
| EP0084599A1 (en) | 1983-08-03 |
| NO155879B (no) | 1987-03-09 |
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