DE2104825A1 - Fluoreszenzfarbstoffe - Google Patents
FluoreszenzfarbstoffeInfo
- Publication number
- DE2104825A1 DE2104825A1 DE19712104825 DE2104825A DE2104825A1 DE 2104825 A1 DE2104825 A1 DE 2104825A1 DE 19712104825 DE19712104825 DE 19712104825 DE 2104825 A DE2104825 A DE 2104825A DE 2104825 A1 DE2104825 A1 DE 2104825A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- hydrogen
- bromine
- chlorine
- acid
- 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.)
- Pending
Links
- 239000007850 fluorescent dye Substances 0.000 title claims description 5
- 239000000460 chlorine Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000004033 plastic Substances 0.000 claims description 7
- 229920003023 plastic Polymers 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- -1 Nitro, methyl Chemical group 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000001530 fumaric acid Substances 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 4
- YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 229920000515 polycarbonate Polymers 0.000 claims description 4
- 239000004417 polycarbonate Substances 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 229920000193 polymethacrylate Polymers 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 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 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 2
- PMVSDNDAUGGCCE-TYYBGVCCSA-L Ferrous fumarate Chemical compound [Fe+2].[O-]C(=O)\C=C\C([O-])=O PMVSDNDAUGGCCE-TYYBGVCCSA-L 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 238000001746 injection moulding Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- KCSFGCVDFUCOIJ-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-n-phenylmethanimine Chemical compound C1=C(OC)C(OC)=CC=C1C=NC1=CC=CC=C1 KCSFGCVDFUCOIJ-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- MTDSQGUSTKBGHA-UHFFFAOYSA-N 2-bromobutanedioyl dichloride Chemical compound ClC(=O)CC(Br)C(Cl)=O MTDSQGUSTKBGHA-UHFFFAOYSA-N 0.000 description 1
- 101100286286 Dictyostelium discoideum ipi gene Proteins 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/08—Aza-anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3437—Six-membered rings condensed with carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH146570A CH541609A (de) | 1970-02-03 | 1970-02-03 | Verfahren zur Herstellung von Bi-isochinolinonen und deren Verwendung als Fluoreszenzfarbstoffe in Kunststoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2104825A1 true DE2104825A1 (de) | 1971-08-19 |
Family
ID=4211101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712104825 Pending DE2104825A1 (de) | 1970-02-03 | 1971-02-02 | Fluoreszenzfarbstoffe |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3751419A (OSRAM) |
| CH (1) | CH541609A (OSRAM) |
| DE (1) | DE2104825A1 (OSRAM) |
| FR (1) | FR2079212B1 (OSRAM) |
| GB (1) | GB1279372A (OSRAM) |
| NL (1) | NL7101373A (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3921025A1 (de) * | 1989-06-27 | 1991-01-03 | Langhals Heinz | Ein neues syntheseverfahren zur darstellung von bipyridylen durch arylkopplung und neue bipyridyle |
| EP0594795B1 (en) * | 1991-04-12 | 2002-02-13 | THE UNITED STATES OF AMERICA as represented by the Secretary United States Department of Commerce | Michellamines useful as antiviral agents, composition and method of treatment |
| US6140339A (en) * | 1994-02-14 | 2000-10-31 | The United States Of America As Represented By The Department Of Health And Human Services | Monomeric and dimeric arylisoquinoline alkaloids and derivatives thereof |
| US5639761A (en) | 1994-02-14 | 1997-06-17 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Antimalarial naphthylisoquinoline alkaloids and pharmaceutical compositions and medical uses thereof |
| US5578729A (en) * | 1994-07-22 | 1996-11-26 | The United States Of America As Represented By The Department Of Health And Human Services | Dimeric arylisoquinoline alkaloid compounds |
| JP2012131862A (ja) * | 2010-12-20 | 2012-07-12 | Adeka Corp | 近赤外線吸収性合成樹脂組成物 |
| US10211402B2 (en) * | 2016-05-11 | 2019-02-19 | International Business Machines Corporation | Dibromo-diiodo-dipolycyclic compound and electron acceptor molecules derived therefrom |
-
1970
- 1970-02-03 CH CH146570A patent/CH541609A/de not_active IP Right Cessation
-
1971
- 1971-01-28 US US00110772A patent/US3751419A/en not_active Expired - Lifetime
- 1971-02-02 DE DE19712104825 patent/DE2104825A1/de active Pending
- 1971-02-02 NL NL7101373A patent/NL7101373A/xx unknown
- 1971-02-02 FR FR7103431A patent/FR2079212B1/fr not_active Expired
- 1971-04-19 GB GB20816/71A patent/GB1279372A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2079212A1 (OSRAM) | 1971-11-12 |
| NL7101373A (OSRAM) | 1971-08-05 |
| US3751419A (en) | 1973-08-07 |
| CH541609A (de) | 1973-09-15 |
| FR2079212B1 (OSRAM) | 1975-08-22 |
| GB1279372A (en) | 1972-06-28 |
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