CA2135556A1 - Process for preparing perylene-3-4-dicarboxylic acid derivatives, the derivatives thus prepared and their use - Google Patents
Process for preparing perylene-3-4-dicarboxylic acid derivatives, the derivatives thus prepared and their useInfo
- Publication number
- CA2135556A1 CA2135556A1 CA002135556A CA2135556A CA2135556A1 CA 2135556 A1 CA2135556 A1 CA 2135556A1 CA 002135556 A CA002135556 A CA 002135556A CA 2135556 A CA2135556 A CA 2135556A CA 2135556 A1 CA2135556 A1 CA 2135556A1
- Authority
- CA
- Canada
- Prior art keywords
- perylene
- dicarboximide
- formula
- dicarboxylic
- preparing
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- -1 perylene-3,4-dicarboxylic diesters Chemical class 0.000 claims abstract description 74
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 40
- SXMCIQXYGMZFMH-UHFFFAOYSA-N perylene-3,4-dicarboxylic anhydride Chemical compound C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 SXMCIQXYGMZFMH-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 27
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 claims abstract description 13
- JVURVJHBFHCOQX-UHFFFAOYSA-N perylene-3,4-dicarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O JVURVJHBFHCOQX-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000007062 hydrolysis Effects 0.000 claims abstract description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 8
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 6
- 239000011368 organic material Substances 0.000 claims abstract description 5
- QFYJXRHWJYLMCX-UHFFFAOYSA-N perylene-3,4-dicarboximidamide Chemical class C=12C3=CC=CC2=CC=CC=1C1=CC=C(C(N)=N)C2=C1C3=CC=C2C(=N)N QFYJXRHWJYLMCX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000518 rheometry Methods 0.000 claims abstract description 4
- 238000005401 electroluminescence Methods 0.000 claims abstract description 3
- 239000000990 laser dye Substances 0.000 claims abstract description 3
- 108091008695 photoreceptors Proteins 0.000 claims abstract description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 58
- LBOJSACZVLWUHN-UHFFFAOYSA-N perylene-3,4-dicarboximide Chemical compound C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)NC(=O)C4=CC=C3C1=C42 LBOJSACZVLWUHN-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000002837 carbocyclic group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 159000000007 calcium salts Chemical class 0.000 claims description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 5
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 150000003751 zinc Chemical class 0.000 claims description 4
- 239000004246 zinc acetate Substances 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 159000000003 magnesium salts Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000005837 1,2-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([*:2])C1([H])[H] 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 238000006254 arylation reaction Methods 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 229940046892 lead acetate Drugs 0.000 claims description 2
- 150000002696 manganese Chemical class 0.000 claims description 2
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 239000012038 nucleophile Substances 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- XQOWMZUKZHRNDV-UHFFFAOYSA-N perylene-3,4-dicarboxamide Chemical compound C=12C3=CC=CC2=CC=CC=1C1=CC=C(C(N)=O)C2=C1C3=CC=C2C(=O)N XQOWMZUKZHRNDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 230000003381 solubilizing effect Effects 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 13
- 150000008064 anhydrides Chemical class 0.000 abstract description 9
- 150000003141 primary amines Chemical class 0.000 abstract description 7
- 150000003949 imides Chemical class 0.000 abstract description 4
- 238000009833 condensation Methods 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract description 3
- 238000005424 photoluminescence Methods 0.000 abstract description 2
- 239000003086 colorant Substances 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 117
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 77
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 74
- 239000000741 silica gel Substances 0.000 description 74
- 229910002027 silica gel Inorganic materials 0.000 description 74
- 229960001866 silicon dioxide Drugs 0.000 description 74
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 239000000047 product Substances 0.000 description 46
- 239000000203 mixture Substances 0.000 description 42
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 235000019441 ethanol Nutrition 0.000 description 27
- 239000007787 solid Substances 0.000 description 24
- 238000001035 drying Methods 0.000 description 22
- 238000000605 extraction Methods 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 239000000843 powder Substances 0.000 description 19
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- WPVHXFPEBJZDPS-UHFFFAOYSA-N n-(2,5-di-t-butylphenyl)perylene-3,4-dicarboximide Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(N2C(C3=CC=C4C=5C=CC=C6C=CC=C(C=56)C5=CC=C(C3=C54)C2=O)=O)=C1 WPVHXFPEBJZDPS-UHFFFAOYSA-N 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 15
- 238000004587 chromatography analysis Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- GBEWPQKPCMZPBX-UHFFFAOYSA-N n-(1-hexylheptyl)perylene-3,4-dicarboximide Chemical compound C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)N(C(CCCCCC)CCCCCC)C(=O)C4=CC=C3C1=C42 GBEWPQKPCMZPBX-UHFFFAOYSA-N 0.000 description 13
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 12
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 8
- 238000006396 nitration reaction Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 244000309464 bull Species 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- TXJMKHFGXLRLJG-UHFFFAOYSA-N 16-hexyl-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(21),2,4,6(23),7,9,11,13,18(22),19-decaene-15,17-dione Chemical compound C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)N(CCCCCC)C(=O)C4=CC=C3C1=C42 TXJMKHFGXLRLJG-UHFFFAOYSA-N 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000005100 correlation spectroscopy Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 4
- PUARYHPMEVSYOG-UHFFFAOYSA-N 9-nitro-n-(1-hexylheptyl)perylene-3,4-dicarboximide Chemical compound C=12C3=CC=CC2=C([N+]([O-])=O)C=CC=1C1=CC=C2C(=O)N(C(CCCCCC)CCCCCC)C(=O)C4=CC=C3C1=C42 PUARYHPMEVSYOG-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000004791 1D NOESY Methods 0.000 description 3
- CKANBDWCPAUNHI-UHFFFAOYSA-N 5-bromo-16-(2,5-ditert-butylphenyl)-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(20),2,4,6,8,10(23),11(21),12,14(22),18-decaene-15,17-dione Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(N2C(C3=CC=C4C=5C=CC(Br)=C6C=CC=C(C=56)C5=CC=C(C3=C54)C2=O)=O)=C1 CKANBDWCPAUNHI-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- HEYMYXXTAWBRDO-UHFFFAOYSA-N n-(4-t-butylphenyl)perylene-3,4-dicarboximide Chemical compound C1=CC(C(C)(C)C)=CC=C1N(C(=O)C=1C2=C3C4=CC=1)C(=O)C2=CC=C3C1=C2C4=CC=CC2=CC=C1 HEYMYXXTAWBRDO-UHFFFAOYSA-N 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- WRJVRADLDBPLIA-UHFFFAOYSA-N 16-cyclooctyl-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(21),2,4,6(23),7,9,11,13,18(22),19-decaene-15,17-dione Chemical compound O=C1C(C2=C34)=CC=C3C(C=35)=CC=CC5=CC=CC=3C4=CC=C2C(=O)N1C1CCCCCCC1 WRJVRADLDBPLIA-UHFFFAOYSA-N 0.000 description 2
- RGTIOMVTXAIXGG-UHFFFAOYSA-N 16-octyl-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(21),2,4,6(23),7,9,11,13,18(22),19-decaene-15,17-dione Chemical compound C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)N(CCCCCCCC)C(=O)C4=CC=C3C1=C42 RGTIOMVTXAIXGG-UHFFFAOYSA-N 0.000 description 2
- WQMGXXJWVZLFOB-UHFFFAOYSA-N 16-tetradecyl-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(21),2,4,6(23),7,9,11,13,18(22),19-decaene-15,17-dione Chemical compound C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)N(CCCCCCCCCCCCCC)C(=O)C4=CC=C3C1=C42 WQMGXXJWVZLFOB-UHFFFAOYSA-N 0.000 description 2
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 2
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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
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- 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
- C07D221/18—Ring systems of four or more rings
-
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH340193 | 1993-11-12 | ||
| CH3401/93-6 | 1993-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2135556A1 true CA2135556A1 (en) | 1995-05-13 |
Family
ID=4255191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002135556A Abandoned CA2135556A1 (en) | 1993-11-12 | 1994-11-10 | Process for preparing perylene-3-4-dicarboxylic acid derivatives, the derivatives thus prepared and their use |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5650513A (enExample) |
| EP (1) | EP0657436B1 (enExample) |
| JP (2) | JP3634415B2 (enExample) |
| CA (1) | CA2135556A1 (enExample) |
| DE (1) | DE59410008D1 (enExample) |
| TW (1) | TW279860B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114315717A (zh) * | 2022-01-02 | 2022-04-12 | 桂林理工大学 | 一种苝单酰亚胺二甲酸二酯-柔性桥-苯并菲树枝状化合物及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0698649A1 (de) * | 1994-08-26 | 1996-02-28 | Basf Aktiengesellschaft | Verwendung von thermoplastisch verarbeitbaren, langzeitstabilen elektrolumineszenten Materialien |
| DE19501737A1 (de) * | 1995-01-20 | 1996-07-25 | Basf Ag | Verfahren zur Herstellung und Reinigung von Perylen-3,4-dicarbonsäureimiden |
| DE19622673A1 (de) * | 1996-06-05 | 1997-12-11 | Basf Ag | Verfahren zur Herstellung von Perylen-3,4-dicarbonsäureimiden |
| DE19701009A1 (de) * | 1997-01-14 | 1998-07-16 | Leonhard Feiler | Verfahren zur Herstellung von Perylen-3,4-dicarbonsäureanhydriden |
| DE19700990A1 (de) * | 1997-01-14 | 1998-07-16 | Langhals Heinz | Die ausbalancierte Decarboxylierung von aromatischen Polycarbonsäuren - eine einstufige Synthese von Perylen-3,4-dicarbonsäureanhydrid |
| DE19940708A1 (de) * | 1999-08-27 | 2001-03-01 | Basf Ag | Thermochrome Rylenfarbstoffe |
| DE19949382A1 (de) | 1999-10-13 | 2001-04-19 | Basf Ag | Verwendung feinteiliger, farbstoffhaltiger Polymerisate PF als farbgebenden Bestandteil in kosmetischen Mitteln |
| JP2001348494A (ja) * | 2000-06-09 | 2001-12-18 | Teijin Chem Ltd | 光学用樹脂組成物および光記録媒体基板 |
| US6462128B1 (en) * | 2000-07-14 | 2002-10-08 | Clariant International Ltd. | Process of making finely divided opaque particles |
| US6391104B1 (en) | 2000-12-01 | 2002-05-21 | Bayer Corporation | Perylene pigment compositions |
| DE10108601A1 (de) * | 2001-02-22 | 2002-09-05 | Basf Ag | Thermochrome Rylenfarbstoffe |
| JP4544757B2 (ja) * | 2001-02-23 | 2010-09-15 | 三井化学株式会社 | 有機電界発光素子 |
| US6692562B2 (en) | 2002-03-08 | 2004-02-17 | Sun Chemical Corporation | Process for making perylene pigment compositions |
| DE10243906A1 (de) | 2002-09-20 | 2004-04-01 | Basf Ag | 9-Cyanosubstituierte Perylen-3,4-dicarbonsäuremonoimide |
| WO2005089094A2 (en) * | 2003-11-21 | 2005-09-29 | The Board Of Regents Of The University And Community College System Of Nevada | Materials and methods for the preparation of anisotropically-ordered solids |
| US7416601B2 (en) † | 2004-02-11 | 2008-08-26 | Basf Aktiengesellschaft | Black perylene pigments |
| FR2868776B1 (fr) * | 2004-04-13 | 2008-04-18 | Servier Lab | Nouveau procede de synthese de derives de la 1,3-dihydro- 2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| DE102004029385A1 (de) * | 2004-06-17 | 2006-06-08 | Wella Ag | Verwendung von fluoreszierenden Perylenverbindungen zur Behandlung menschlicher Haare |
| EP1802623A1 (en) * | 2004-10-12 | 2007-07-04 | Novo Nordisk A/S | 11beta-hydroxysteroid dehydrogenase type 1 active spiro compounds |
| DE102004054303A1 (de) | 2004-11-09 | 2006-05-11 | Basf Ag | Verfahren zur Herstellung von Perylen-3,4-dicarbonsäureimiden |
| US20090124598A1 (en) * | 2005-11-01 | 2009-05-14 | Henrik Sune Andersen | Pharmaceutical use of substituted amides |
| KR20080069189A (ko) * | 2005-11-01 | 2008-07-25 | 트랜스테크 파르마, 인크. | 치환된 아미드의 약학적 사용 |
| CA2646588A1 (en) * | 2006-03-21 | 2007-09-27 | High Point Pharmaceuticals, Llc | Adamantane derivatives for the treatment of the metabolic syndrome |
| AU2007236049A1 (en) | 2006-04-07 | 2007-10-18 | High Point Pharmaceuticals, Llc | 11beta-hydroxysteroid dehydrogenase type 1 active compounds |
| WO2007144394A2 (en) * | 2006-06-16 | 2007-12-21 | High Point Pharmaceuticals, Llc. | Pharmaceutical use of substituted piperidine carboxamides |
| WO2008006702A1 (en) * | 2006-07-13 | 2008-01-17 | High Point Pharmaceuticals, Llc. | 11beta-hydroxysteroid dehydrogenase type 1 active compounds |
| EP1878721A1 (en) * | 2006-07-13 | 2008-01-16 | Novo Nordisk A/S | 4-Piperidylbenzamides as 11-beta-hydroxysteroid dehydrogenase type 1 inhibitors |
| BRPI0806537A2 (pt) * | 2007-01-10 | 2014-04-22 | Albany Molecular Res Inc | Indazóis substituídos por 5-piridinona |
| ES2390187T3 (es) | 2007-02-19 | 2012-11-07 | Basf Se | Método para la producción de pigmento rojo 149 |
| WO2008101885A1 (en) * | 2007-02-23 | 2008-08-28 | High Point Pharmaceuticals, Llc | N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase |
| CA2675669C (en) | 2007-02-23 | 2015-05-26 | High Point Pharmaceuticals, Llc | Novel compounds |
| EP2129652A2 (en) * | 2007-02-23 | 2009-12-09 | High Point Pharmaceuticals, LLC | N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase |
| JP2010519240A (ja) * | 2007-02-23 | 2010-06-03 | ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー | １１−ベータ−ヒドロキシステロイドデヒドロゲナーゼの阻害剤としての、ｎ−アダマンチルベンズアミド |
| BRPI0721430A2 (pt) * | 2007-03-09 | 2013-01-08 | High Point Pharmaceuticals Llc | amidas indol e benzimidazol como inibidoras de hidroxiesteràide deidrogenase |
| US20100056600A1 (en) * | 2007-03-28 | 2010-03-04 | Soren Ebdrup | 11beta-hsd1 active compounds |
| JP2010523692A (ja) * | 2007-04-11 | 2010-07-15 | ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー | 新規合成物 |
| ES2393230T3 (es) * | 2007-04-24 | 2012-12-19 | High Point Pharmaceuticals, Llc | Uso farmacéutico de amidas sustituidas |
| ATE544759T1 (de) * | 2007-07-21 | 2012-02-15 | Albany Molecular Res Inc | 5-pyridinon-substituierte indazole und pharmazeutische zusammensetzungen davon |
| EP2110237A1 (de) * | 2008-04-16 | 2009-10-21 | Kuraray Europe GmbH | Photoluminiszierende Zwischenschichtfolien für Verbundverglasungen |
| ATE544753T1 (de) * | 2008-05-23 | 2012-02-15 | Basf Se | Chinoide rylendicarboximide als ir-absorber |
| US8314325B2 (en) * | 2008-08-19 | 2012-11-20 | Sabic Innovative Plastics Ip B.V. | Luminescent solar collector |
| US8304647B2 (en) * | 2008-08-19 | 2012-11-06 | Sabic Innovative Plastics Ip B.V. | Luminescent solar collector |
| US8304645B2 (en) * | 2008-08-19 | 2012-11-06 | Sabic Innovative Plastics Ip B.V. | Luminescent solar collector |
| US8299354B2 (en) * | 2008-08-19 | 2012-10-30 | Sabic Innovative Plastics Ip B.V. | Luminescent solar collector |
| US8404892B2 (en) * | 2010-05-27 | 2013-03-26 | Eastman Kodak Company | Aromatic amic acid salts and compositions |
| CN105399631A (zh) * | 2015-12-17 | 2016-03-16 | 山东师范大学 | 3,4-苝二羧酸酯类化合物及其合成方法和应用 |
| US20200332184A1 (en) | 2017-01-18 | 2020-10-22 | Basf Se | Fluorescent colorants based on cyanoaryl-substituted naphthoylenebenzimidazole compounds |
| KR102718070B1 (ko) | 2017-12-19 | 2024-10-17 | 바스프 에스이 | 시아노아릴 치환된 벤즈(오티)오크산텐 화합물 |
| CN112384593A (zh) | 2018-06-22 | 2021-02-19 | 巴斯夫欧洲公司 | 作为用于显示器和照明应用的绿色发射体的光稳定氰基取代硼二吡咯亚甲基染料 |
| CN112778137A (zh) * | 2021-01-08 | 2021-05-11 | 山东师范大学 | 一种端位硝化的3，4-苝二羧酸酯类化合物及其合成方法与应用 |
| CN115466392B (zh) * | 2022-09-13 | 2023-07-14 | 中国科学技术大学 | 一种苝酰亚胺笼型聚倍半硅氧烷聚合物材料及其制备和荧光调控方法 |
| WO2025237878A1 (en) | 2024-05-13 | 2025-11-20 | Sun Chemical B.V. | Low bleeding perylene black pigments and process for producing the same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB272528A (enExample) * | 1900-01-01 | |||
| DE486491C (de) * | 1926-06-10 | 1929-11-18 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von Perylen und Abkoemmlingen desselben |
| US3557233A (en) * | 1968-03-14 | 1971-01-19 | American Cyanamid Co | Aromatic hydrocarbons substituted by phenylethynyl groups |
| BE795035A (fr) * | 1972-02-07 | 1973-08-06 | Ugine Kuhlmann | Pigments amino-imidiques |
| DE2512516C2 (de) * | 1975-03-21 | 1985-01-03 | Basf Ag, 6700 Ludwigshafen | Perylen-3,4,9,10-tetracarbonsäureester |
| DE3526249A1 (de) * | 1985-07-23 | 1987-01-29 | Hoechst Ag | Elektrophotographisches aufzeichnungsmaterial |
| DE9214577U1 (de) * | 1992-10-28 | 1993-12-16 | Mayer, Herbert, 87700 Memmingen | Dampferzeuger |
| DE4236885A1 (de) * | 1992-10-31 | 1994-05-05 | Basf Ag | Quaterrylentetracarbonsäureimide |
-
1994
- 1994-11-02 TW TW083110094A patent/TW279860B/zh active
- 1994-11-03 EP EP94810637A patent/EP0657436B1/de not_active Expired - Lifetime
- 1994-11-03 DE DE59410008T patent/DE59410008D1/de not_active Expired - Lifetime
- 1994-11-10 CA CA002135556A patent/CA2135556A1/en not_active Abandoned
- 1994-11-10 US US08/337,917 patent/US5650513A/en not_active Expired - Lifetime
- 1994-11-11 JP JP27688294A patent/JP3634415B2/ja not_active Expired - Fee Related
-
2004
- 2004-08-03 JP JP2004226562A patent/JP3784816B2/ja not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114315717A (zh) * | 2022-01-02 | 2022-04-12 | 桂林理工大学 | 一种苝单酰亚胺二甲酸二酯-柔性桥-苯并菲树枝状化合物及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW279860B (enExample) | 1996-07-01 |
| JPH07188178A (ja) | 1995-07-25 |
| DE59410008D1 (de) | 2002-01-24 |
| EP0657436A3 (enExample) | 1995-07-19 |
| JP3634415B2 (ja) | 2005-03-30 |
| JP2004323534A (ja) | 2004-11-18 |
| JP3784816B2 (ja) | 2006-06-14 |
| EP0657436A2 (de) | 1995-06-14 |
| EP0657436B1 (de) | 2001-12-12 |
| US5650513A (en) | 1997-07-22 |
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