JP2002534552A - ナフタレンヒドラザムイミド類及びペリレンヒドラザムイミド類 - Google Patents
ナフタレンヒドラザムイミド類及びペリレンヒドラザムイミド類Info
- Publication number
- JP2002534552A JP2002534552A JP2000592358A JP2000592358A JP2002534552A JP 2002534552 A JP2002534552 A JP 2002534552A JP 2000592358 A JP2000592358 A JP 2000592358A JP 2000592358 A JP2000592358 A JP 2000592358A JP 2002534552 A JP2002534552 A JP 2002534552A
- Authority
- JP
- Japan
- Prior art keywords
- chcl
- max
- yield
- mmol
- fluorescence
- 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 title description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title description 10
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 title description 7
- 150000001875 compounds Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000003086 colorant Substances 0.000 claims description 14
- 239000000975 dye Substances 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- 239000000049 pigment Substances 0.000 claims description 10
- 150000008064 anhydrides Chemical class 0.000 claims description 9
- 239000007850 fluorescent dye Substances 0.000 claims description 9
- 150000002429 hydrazines Chemical class 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 150000004985 diamines Chemical class 0.000 claims description 6
- 239000003973 paint Substances 0.000 claims description 6
- 150000003141 primary amines Chemical class 0.000 claims description 6
- 239000004065 semiconductor Substances 0.000 claims description 6
- 239000000976 ink Substances 0.000 claims description 5
- 229910021536 Zeolite Inorganic materials 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000123 paper Substances 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 239000008199 coating composition Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 238000003018 immunoassay Methods 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims description 2
- 238000000504 luminescence detection Methods 0.000 claims description 2
- 238000004020 luminiscence type Methods 0.000 claims description 2
- 239000000983 mordant dye Substances 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 238000010422 painting Methods 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 239000000700 radioactive tracer Substances 0.000 claims description 2
- 238000011896 sensitive detection Methods 0.000 claims description 2
- 238000004611 spectroscopical analysis Methods 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 239000000984 vat dye Substances 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 93
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 90
- 229910052757 nitrogen Inorganic materials 0.000 description 85
- -1 perylene anhydride Chemical class 0.000 description 77
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 48
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 44
- 239000000741 silica gel Substances 0.000 description 44
- 229910002027 silica gel Inorganic materials 0.000 description 44
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 40
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 29
- 238000006862 quantum yield reaction Methods 0.000 description 26
- 239000000203 mixture Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 229910052786 argon Inorganic materials 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000003480 eluent Substances 0.000 description 13
- 239000000843 powder Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WLDRFJDGKMTPPV-UHFFFAOYSA-N 1,2-dimethylhydrazine dihydrochloride Chemical compound Cl.Cl.CNNC WLDRFJDGKMTPPV-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- LFYYDXRFYGNQHQ-UHFFFAOYSA-N 1,2-di(nonyl)hydrazine Chemical compound CCCCCCCCCNNCCCCCCCCC LFYYDXRFYGNQHQ-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- DIWQZSSVXPNKLB-UHFFFAOYSA-N 1,2-diheptylhydrazine Chemical compound CCCCCCCNNCCCCCCC DIWQZSSVXPNKLB-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 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 description 4
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 4
- 239000001054 red pigment Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 3
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000292 calcium oxide Substances 0.000 description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- KDXQVJZMNHNQDK-UHFFFAOYSA-N 1,2-di(heptan-4-yl)hydrazine;dihydrochloride Chemical compound Cl.Cl.CCCC(CCC)NNC(CCC)CCC KDXQVJZMNHNQDK-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- CXUGAWWYKSOLEL-UHFFFAOYSA-N 2h-cinnolin-3-one Chemical compound C1=CC=C2N=NC(O)=CC2=C1 CXUGAWWYKSOLEL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000243251 Hydra Species 0.000 description 2
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PFLUPZGCTVGDLV-UHFFFAOYSA-N acetone azine Chemical compound CC(C)=NN=C(C)C PFLUPZGCTVGDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000001055 blue pigment Substances 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000000407 epitaxy Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 210000004209 hair Anatomy 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 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 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 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 description 2
- 239000002964 rayon Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- JEHCGAMWUNPVOI-UHFFFAOYSA-M st50974807 Chemical compound [K+].C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C(C([O-])=O)C2=C1C3=CC=C2C(=O)O JEHCGAMWUNPVOI-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- IFZHGQSUNAKKSN-UHFFFAOYSA-N 1,1-diethylhydrazine Chemical compound CCN(N)CC IFZHGQSUNAKKSN-UHFFFAOYSA-N 0.000 description 1
- FEBRIAPYLGMZSR-UHFFFAOYSA-N 1,2-dibutylhydrazine Chemical compound CCCCNNCCCC FEBRIAPYLGMZSR-UHFFFAOYSA-N 0.000 description 1
- MJLIHWWXDNNKON-UHFFFAOYSA-N 1,2-dihexylhydrazine Chemical compound CCCCCCNNCCCCCC MJLIHWWXDNNKON-UHFFFAOYSA-N 0.000 description 1
- FTBODWYOSACVAV-UHFFFAOYSA-N 1,2-dioctylhydrazine Chemical compound CCCCCCCCNNCCCCCCCC FTBODWYOSACVAV-UHFFFAOYSA-N 0.000 description 1
- ISCDRGSIMZGUFJ-UHFFFAOYSA-N 1,2-dipentylhydrazine Chemical compound CCCCCNNCCCCC ISCDRGSIMZGUFJ-UHFFFAOYSA-N 0.000 description 1
- BOOQVRGRSDTZRZ-UHFFFAOYSA-N 1,2-dipropylhydrazine Chemical compound CCCNNCCC BOOQVRGRSDTZRZ-UHFFFAOYSA-N 0.000 description 1
- ATKSXVJFUPVUCV-UHFFFAOYSA-N 17-methyl-3,10,17-triazahexacyclo[13.6.2.02,10.04,9.012,22.019,23]tricosa-1(22),2,4,6,8,12,14,19(23),20-nonaene-11,16,18-trione Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C(=O)N(C)C(=O)C4=CC=C1C2=C43 ATKSXVJFUPVUCV-UHFFFAOYSA-N 0.000 description 1
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- LKOZHLXUWUBRDK-UHFFFAOYSA-N 4-nitro-1,8-naphthalic anhydride Chemical compound O=C1OC(=O)C2=CC=CC3=C2C1=CC=C3[N+](=O)[O-] LKOZHLXUWUBRDK-UHFFFAOYSA-N 0.000 description 1
- 244000198134 Agave sisalana Species 0.000 description 1
- VHIDZOIKPWVLTP-UHFFFAOYSA-N C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)N(NCCCCCCC)C(=O)C4=CC=C3C1=C42 Chemical compound C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)N(NCCCCCCC)C(=O)C4=CC=C3C1=C42 VHIDZOIKPWVLTP-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 101001018064 Homo sapiens Lysosomal-trafficking regulator Proteins 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 102100033472 Lysosomal-trafficking regulator Human genes 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 244000038561 Modiola caroliniana Species 0.000 description 1
- 235000010703 Modiola caroliniana Nutrition 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004693 Polybenzimidazole Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical compound N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 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 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 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 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 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
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane 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
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- DDPWVABNMBRBFI-UHFFFAOYSA-N tert-butylhydrazine;hydron;chloride Chemical compound Cl.CC(C)(C)NN DDPWVABNMBRBFI-UHFFFAOYSA-N 0.000 description 1
- FXNJNGMYIZRQRG-UHFFFAOYSA-N tridecan-7-amine Chemical compound CCCCCCC(N)CCCCCC FXNJNGMYIZRQRG-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000001052 yellow pigment Substances 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
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/36—Benzo-cinnolines
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-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
- 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
- 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Indole Compounds (AREA)
- Paper (AREA)
- Paints Or Removers (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19900063.8 | 1999-01-04 | ||
| DE19900063A DE19900063A1 (de) | 1999-01-04 | 1999-01-04 | Naphthalin- und Perylenhydrazamimide - eine neue Klasse von Farbstoffen |
| PCT/EP1999/010367 WO2000040657A1 (en) | 1999-01-04 | 1999-12-24 | Naphthalenehydrazamimides and perylenehydrazamimides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002534552A true JP2002534552A (ja) | 2002-10-15 |
| JP2002534552A5 JP2002534552A5 (enExample) | 2007-02-15 |
Family
ID=7893563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000592358A Pending JP2002534552A (ja) | 1999-01-04 | 1999-12-24 | ナフタレンヒドラザムイミド類及びペリレンヒドラザムイミド類 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6143890A (enExample) |
| EP (1) | EP1141140B1 (enExample) |
| JP (1) | JP2002534552A (enExample) |
| AT (1) | ATE223462T1 (enExample) |
| AU (1) | AU2102400A (enExample) |
| DE (2) | DE19900063A1 (enExample) |
| TW (1) | TW589350B (enExample) |
| WO (1) | WO2000040657A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009515846A (ja) * | 2005-11-10 | 2009-04-16 | ビーエーエスエフ ソシエタス・ヨーロピア | 太陽電池中での光増感剤としてのリレン誘導体の使用 |
| US8232031B2 (en) | 2007-09-10 | 2012-07-31 | Ricoh Company, Ltd. | Naphthalenetetracarboxylic acid diimide derivative and electrophotographic photoconductor having the same |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001245643A1 (en) * | 2000-03-14 | 2001-09-24 | Genigma Corporation | Biomarkers for the labeling, visual detection and quantification of biomolecules |
| US6391104B1 (en) | 2000-12-01 | 2002-05-21 | Bayer Corporation | Perylene pigment compositions |
| US6692562B2 (en) | 2002-03-08 | 2004-02-17 | Sun Chemical Corporation | Process for making perylene pigment compositions |
| DE102004006143A1 (de) | 2004-02-07 | 2005-08-25 | Wella Ag | Neue Naphthalinderivate und diese Verbindungen enthaltende Färbemittel für Keratinfasern |
| DE102004008480B4 (de) * | 2004-02-20 | 2011-06-22 | Theodor Heimeier Metallwerk GmbH, 59597 | Dichtigkeitsprüfung geschlossener Systeme mit Hilfe von Fluoreszenzfarbstoffen |
| EP2166040A1 (en) * | 2008-09-22 | 2010-03-24 | Radiant Color N.V. | Novel lipophilic fluorescent dyes and a process for their production |
| CN102841066A (zh) * | 2012-08-24 | 2012-12-26 | 深圳市谱尼测试科技有限公司 | 一种reach高度关注物质肼含量的测定方法 |
| 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 |
|---|---|---|---|---|
| US2992220A (en) * | 1956-12-05 | 1961-07-11 | Ici Ltd | New anthra-1':9'(n):10'(n):5'-dipyridazones and anthra-1':9'(n):10'(n):4'-dipyridazones chemical compounds |
| DE4035009A1 (de) * | 1990-11-03 | 1992-05-07 | Hoechst Ag | Schwarze perylen-3,4,9,10-tetracarbonsaeurediimide, ihre herstellung und verwendung |
| EP0769532B1 (de) * | 1995-10-12 | 2002-03-13 | Ciba SC Holding AG | Naphthalinlactamimid-Fluoreszenzfarbstoffe |
| DE19701009A1 (de) * | 1997-01-14 | 1998-07-16 | Leonhard Feiler | Verfahren zur Herstellung von Perylen-3,4-dicarbonsäureanhydriden |
| EP0896964B1 (de) * | 1997-07-24 | 2006-03-08 | Ciba SC Holding AG | Perylenhydrazidimide als Carbonylderivatisierungsreagenzien |
-
1999
- 1999-01-04 DE DE19900063A patent/DE19900063A1/de not_active Withdrawn
- 1999-12-16 US US09/465,869 patent/US6143890A/en not_active Expired - Fee Related
- 1999-12-24 JP JP2000592358A patent/JP2002534552A/ja active Pending
- 1999-12-24 EP EP99965553A patent/EP1141140B1/en not_active Expired - Lifetime
- 1999-12-24 AU AU21024/00A patent/AU2102400A/en not_active Abandoned
- 1999-12-24 DE DE69902818T patent/DE69902818T2/de not_active Expired - Fee Related
- 1999-12-24 AT AT99965553T patent/ATE223462T1/de not_active IP Right Cessation
- 1999-12-24 WO PCT/EP1999/010367 patent/WO2000040657A1/en not_active Ceased
-
2000
- 2000-01-03 TW TW089100015A patent/TW589350B/zh not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009515846A (ja) * | 2005-11-10 | 2009-04-16 | ビーエーエスエフ ソシエタス・ヨーロピア | 太陽電池中での光増感剤としてのリレン誘導体の使用 |
| US8232031B2 (en) | 2007-09-10 | 2012-07-31 | Ricoh Company, Ltd. | Naphthalenetetracarboxylic acid diimide derivative and electrophotographic photoconductor having the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE19900063A1 (de) | 2000-07-27 |
| DE69902818D1 (de) | 2002-10-10 |
| DE69902818T2 (de) | 2003-07-31 |
| US6143890A (en) | 2000-11-07 |
| EP1141140A1 (en) | 2001-10-10 |
| ATE223462T1 (de) | 2002-09-15 |
| TW589350B (en) | 2004-06-01 |
| AU2102400A (en) | 2000-07-24 |
| WO2000040657A1 (en) | 2000-07-13 |
| EP1141140B1 (en) | 2002-09-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3634415B2 (ja) | ペリレン−３，４−ジカルボン酸誘導体の製造方法 | |
| US7662308B2 (en) | Polyhedral oligomeric silsesquioxane (POSS) based fluorescent colorants | |
| US7326793B2 (en) | Process for the preparation of diketopyrrolopyrroles | |
| US6491749B1 (en) | Core-extended perylene bisimides | |
| US6060601A (en) | Fluorescence-derivatisation of carbonyl compounds-novel carbonyl reagents | |
| US6166210A (en) | Perylene imide monocarboxylic acids | |
| DE4338784A1 (de) | Perylen-3,4-dicarbonsäureimide - neue hoch lichtechte Fluoreszenzfarbstoffe | |
| JP3609454B2 (ja) | ペリレンアミジンイミド染料、その製造方法及びその使用 | |
| JP3856859B2 (ja) | ペリレンイミド、新規な二、三および四発色団ペリレン染料の製造方法ならびにその用法 | |
| US5981773A (en) | Preparation of perylene-3,4-dicarboxylic anhydrides | |
| JP2002534552A (ja) | ナフタレンヒドラザムイミド類及びペリレンヒドラザムイミド類 | |
| US6093834A (en) | Preparation of perylene-3,4-dicarboxylic acid anhydrides | |
| JP4962812B2 (ja) | フタロシアニン化合物およびその製造方法、ならびに該フタロシアニン化合物を含有する着色組成物 | |
| DE102007063051A1 (de) | Fluoreszenzmarkierungen durch die "Click-Reaktion". Anwendung der 1,3-dipolaren Cycloaddition | |
| JP2001518078A (ja) | クラウンエーテル誘導化ペリレン | |
| US4166181A (en) | N,n'-diphenyldiimides of 6,12, dialkyl-3,4,9,10-anthanthrene-tetracarboxylic acid | |
| RU1816787C (ru) | N-карбоксиметилимид 4-карбоксиметиламинонафталевой кислоты в качестве люминофора зеленого свечени и способ его получени | |
| JPS5838467B2 (ja) | シンキビスアゾメチンガンリヨウノ セイホウ | |
| GB2048926A (en) | Oxime compounds | |
| JPH064771B2 (ja) | イソインドリン色素 | |
| KR101842344B1 (ko) | 신규한 화합물, 이의 제조 방법, 및 이를 포함하는 액정표시장치용 컬러필터 | |
| Crawford et al. | Azabenz [a] anthracenes | |
| JPH03170458A (ja) | 複素環化合物とそれから得られるポルフイリン化合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20061218 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20061218 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20091117 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20100413 |