JP4086920B2 - ナフタレンラクタムイミド蛍光染料 - Google Patents
ナフタレンラクタムイミド蛍光染料 Download PDFInfo
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- JP4086920B2 JP4086920B2 JP27015896A JP27015896A JP4086920B2 JP 4086920 B2 JP4086920 B2 JP 4086920B2 JP 27015896 A JP27015896 A JP 27015896A JP 27015896 A JP27015896 A JP 27015896A JP 4086920 B2 JP4086920 B2 JP 4086920B2
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- Prior art keywords
- naphthalene
- reaction
- product
- hours
- mmol
- Prior art date
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title description 29
- 239000007850 fluorescent dye Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000004040 coloring Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000011368 organic material Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000000990 laser dye Substances 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 230000001548 androgenic effect Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- -1 aminonaphthalene tricarboxylic acid imide Chemical class 0.000 description 87
- 229910052757 nitrogen Inorganic materials 0.000 description 87
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 76
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
- 239000000243 solution Substances 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
- 238000006243 chemical reaction Methods 0.000 description 45
- 239000000203 mixture Substances 0.000 description 43
- 239000000047 product Substances 0.000 description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
- 239000002244 precipitate Substances 0.000 description 35
- 239000011521 glass Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 239000012153 distilled water Substances 0.000 description 29
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 28
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- 239000007795 chemical reaction product Substances 0.000 description 25
- 239000000843 powder Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- 238000004440 column chromatography Methods 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000009835 boiling Methods 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 19
- 239000012043 crude product Substances 0.000 description 19
- 239000012362 glacial acetic acid Substances 0.000 description 19
- 239000000975 dye Substances 0.000 description 18
- 238000001556 precipitation Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 239000007858 starting material Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 150000008064 anhydrides Chemical class 0.000 description 8
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- 229940126214 compound 3 Drugs 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 229910003460 diamond Inorganic materials 0.000 description 5
- 239000010432 diamond Substances 0.000 description 5
- 150000003949 imides Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 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
- 239000002994 raw material Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 150000003951 lactams Chemical group 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- 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 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001643 poly(ether ketone) Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 238000007157 ring contraction reaction Methods 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- CNPQVEJSVQNWMV-UHFFFAOYSA-N (1-ethylcyclohexyl)methanamine Chemical compound CCC1(CN)CCCCC1 CNPQVEJSVQNWMV-UHFFFAOYSA-N 0.000 description 1
- FBXQBTBVSJWIHD-UHFFFAOYSA-N (1-propylcyclohexyl)methanamine Chemical compound CCCC1(CN)CCCCC1 FBXQBTBVSJWIHD-UHFFFAOYSA-N 0.000 description 1
- JAFHWOGMKFOVFF-UHFFFAOYSA-N 1-amino-2h-naphthalene-1,2,3-tricarboxylic acid Chemical class C1=CC=C2C(N)(C(O)=O)C(C(O)=O)C(C(O)=O)=CC2=C1 JAFHWOGMKFOVFF-UHFFFAOYSA-N 0.000 description 1
- NDLQGVXBUFZFIX-UHFFFAOYSA-N 1-butan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)CC)=CC=CC2=C1 NDLQGVXBUFZFIX-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SZXBDTIPTMLHFY-UHFFFAOYSA-N 2,2-dihexyloctan-1-amine Chemical compound CCCCCCC(CN)(CCCCCC)CCCCCC SZXBDTIPTMLHFY-UHFFFAOYSA-N 0.000 description 1
- AFYUBCQPUVSMBC-UHFFFAOYSA-N 2,2-dimethylheptan-1-amine Chemical compound CCCCCC(C)(C)CN AFYUBCQPUVSMBC-UHFFFAOYSA-N 0.000 description 1
- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
- NUZVLYNISQOZOW-UHFFFAOYSA-N 2,5-ditert-butylaniline Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(N)=C1 NUZVLYNISQOZOW-UHFFFAOYSA-N 0.000 description 1
- NMBHEXMIESBYJQ-UHFFFAOYSA-N 2-methyl-2-propylhexan-1-amine Chemical compound CCCCC(C)(CN)CCC NMBHEXMIESBYJQ-UHFFFAOYSA-N 0.000 description 1
- AEIOZWYBDBVCGW-UHFFFAOYSA-N 2-tert-butylaniline Chemical compound CC(C)(C)C1=CC=CC=C1N AEIOZWYBDBVCGW-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- FBZRBACMKYTOJR-UHFFFAOYSA-N C(C)(CC)C1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45 Chemical group C(C)(CC)C1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45 FBZRBACMKYTOJR-UHFFFAOYSA-N 0.000 description 1
- GPFZHLJPBRAOEN-UHFFFAOYSA-N C(CCC)C(CC1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)(CCCC)C4=CC=CC=C4 Chemical group C(CCC)C(CC1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)(CCCC)C4=CC=CC=C4 GPFZHLJPBRAOEN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- 239000000986 disperse dye Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
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- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Luminescent Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Hybrid Cells (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH02882/95 | 1995-10-12 | ||
| CH288295 | 1995-10-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH09124960A JPH09124960A (ja) | 1997-05-13 |
| JPH09124960A5 JPH09124960A5 (enExample) | 2004-10-14 |
| JP4086920B2 true JP4086920B2 (ja) | 2008-05-14 |
Family
ID=4243716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27015896A Expired - Fee Related JP4086920B2 (ja) | 1995-10-12 | 1996-10-11 | ナフタレンラクタムイミド蛍光染料 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5886183A (enExample) |
| EP (1) | EP0769532B1 (enExample) |
| JP (1) | JP4086920B2 (enExample) |
| CA (1) | CA2187593A1 (enExample) |
| DE (1) | DE59608872D1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0630802U (ja) * | 1992-09-11 | 1994-04-22 | 光洋電子工業株式会社 | Ｐｃのユニット間の接続構造 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19900063A1 (de) * | 1999-01-04 | 2000-07-27 | Heinz Langhals | Naphthalin- und Perylenhydrazamimide - eine neue Klasse von Farbstoffen |
| JPWO2002040479A1 (ja) * | 2000-11-14 | 2004-03-25 | 塩野義製薬株式会社 | 抗ヘリコバクター剤 |
| KR20040045903A (ko) * | 2001-10-22 | 2004-06-02 | 미쓰이 가가쿠 가부시키가이샤 | 이미드 화합물 및 그 화합물을 사용하는 광기록 매체 |
| AU2003235908A1 (en) * | 2002-05-13 | 2003-11-11 | Shionogi And Co., Ltd. | Compounds against helicobacter activity |
| KR100513700B1 (ko) * | 2003-07-04 | 2005-09-09 | 삼성전자주식회사 | 나프탈렌테트라카르복시디이미드 유도체 및 이를 포함하는전자사진감광체 |
| KR100622371B1 (ko) * | 2003-12-15 | 2006-09-18 | 삼성전자주식회사 | 전자흡인기를 갖는 신규한페닐아조메틸렌-사이클로헥사디에논 유도체 및 이를함유하는 전자사진감광체 |
| DE102004006143A1 (de) | 2004-02-07 | 2005-08-25 | Wella Ag | Neue Naphthalinderivate und diese Verbindungen enthaltende Färbemittel für Keratinfasern |
| DE102004006142A1 (de) | 2004-02-07 | 2005-08-25 | Wella Ag | Neutrale und kationische Naphthalinderivate und diese Verbindungen enthaltende Färbemittel für Keratinfasern |
| JP4407435B2 (ja) | 2004-09-02 | 2010-02-03 | 富士ゼロックス株式会社 | 電子写真用トナー、その製造方法及び画像形成方法 |
| EP1655359A1 (de) * | 2004-11-06 | 2006-05-10 | Covion Organic Semiconductors GmbH | Organische Elektrolumineszenzvorrichtung |
| DE102005034685A1 (de) * | 2005-07-25 | 2007-02-08 | Langhals, Heinz, Prof. Dr. | Naphthalinamidinimide und Piperazino-Bisimide |
| US7629605B2 (en) * | 2005-10-31 | 2009-12-08 | Eastman Kodak Company | N-type semiconductor materials for thin film transistors |
| WO2010052287A1 (en) * | 2008-11-07 | 2010-05-14 | Basf Se | Organic semiconducting polymers |
| BR112013004585B1 (pt) * | 2010-09-20 | 2021-09-08 | Merck Sharp & Dohme Corp | Lipídeo catiônico, composição de lnp, e, uso de um lipídeo catiônico |
| CN103382313B (zh) * | 2013-05-03 | 2015-04-08 | 大连理工大学 | 一种萘酰亚胺荧光染料及其制备和应用 |
| US9812645B2 (en) | 2015-02-13 | 2017-11-07 | Flexterra, Inc. | Perylene-based semiconductors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1126074A (en) * | 1966-02-17 | 1968-09-05 | Ici Ltd | Mass colouration of linear polyesters |
| IT1026778B (it) * | 1973-12-06 | 1978-10-20 | Hoechst Ag | Pigmenti luminescenti alla luce diurna processo per la loro preparazione e loro impiego |
| GB1495296A (en) * | 1974-12-31 | 1977-12-14 | Hoechst Ag | 4-amino-1,8-naphthalimide dyestuffs |
| SU559557A1 (ru) * | 1975-09-01 | 1979-01-05 | Предприятие П/Я В-8611 | Замещенные имиды нафтостирил-5,6дикарбоновой кислоты в качестве красителей дл синтетических волокон и способ их получени |
| DE3016764A1 (de) * | 1980-04-30 | 1981-11-05 | Heinz Dr. 5880 Lüdenscheid Langhals | Verfahren zur erhoehung der loeslichkeit aromatischer systeme |
-
1996
- 1996-10-02 EP EP96810656A patent/EP0769532B1/de not_active Expired - Lifetime
- 1996-10-02 DE DE59608872T patent/DE59608872D1/de not_active Expired - Lifetime
- 1996-10-10 CA CA002187593A patent/CA2187593A1/en not_active Abandoned
- 1996-10-11 US US08/729,124 patent/US5886183A/en not_active Expired - Fee Related
- 1996-10-11 JP JP27015896A patent/JP4086920B2/ja not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0630802U (ja) * | 1992-09-11 | 1994-04-22 | 光洋電子工業株式会社 | Ｐｃのユニット間の接続構造 |
Also Published As
| Publication number | Publication date |
|---|---|
| US5886183A (en) | 1999-03-23 |
| JPH09124960A (ja) | 1997-05-13 |
| DE59608872D1 (de) | 2002-04-18 |
| CA2187593A1 (en) | 1997-04-13 |
| EP0769532A1 (de) | 1997-04-23 |
| EP0769532B1 (de) | 2002-03-13 |
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