TWI360563B - - Google Patents
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- TWI360563B TWI360563B TW094119716A TW94119716A TWI360563B TW I360563 B TWI360563 B TW I360563B TW 094119716 A TW094119716 A TW 094119716A TW 94119716 A TW94119716 A TW 94119716A TW I360563 B TWI360563 B TW I360563B
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- -1 cyanine compound Chemical class 0.000 claims description 111
- 230000003287 optical effect Effects 0.000 claims description 82
- 239000000463 material Substances 0.000 claims description 46
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 150000001450 anions Chemical class 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000962 organic group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 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
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 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 claims description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 3
- 239000004575 stone Substances 0.000 claims description 3
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
- 239000010437 gem Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000013078 crystal Substances 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 23
- 150000003839 salts Chemical class 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 238000002425 crystallisation Methods 0.000 description 14
- 230000008025 crystallization Effects 0.000 description 14
- 239000007789 gas Substances 0.000 description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 8
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- FZNQGWYPRJCGRN-UHFFFAOYSA-N F.F.F.F.F.F.P.P Chemical compound F.F.F.F.F.F.P.P FZNQGWYPRJCGRN-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- ZORYZEVTIVPMPO-UHFFFAOYSA-H hexapotassium hexafluoride Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].[K+].[K+].[K+].[K+].[K+].[K+] ZORYZEVTIVPMPO-UHFFFAOYSA-H 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 150000002923 oximes Chemical group 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical class CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000005979 thermal decomposition reaction Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229930182558 Sterol Natural products 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 150000003432 sterols Chemical class 0.000 description 3
- 235000003702 sterols Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FMYDJINDOVUENM-UHFFFAOYSA-N CC1(C(C(=CC=C1)C)C)NN Chemical compound CC1(C(C(=CC=C1)C)C)NN FMYDJINDOVUENM-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 206010036790 Productive cough Diseases 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 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
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 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
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 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 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000021453 onion ring Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 210000003802 sputum Anatomy 0.000 description 2
- 208000024794 sputum Diseases 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- JMFWKUHUEUMQGW-LBPRGKRZSA-N (2S)-6-amino-2-(N-methylanilino)hexanoic acid Chemical group C1(=CC=CC=C1)N([C@@H](CCCCN)C(=O)O)C JMFWKUHUEUMQGW-LBPRGKRZSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- QAWYYDMAJXVMFW-UHFFFAOYSA-N 1-(10-bromodecyl)naphthalene Chemical compound C1(=CC=CC2=CC=CC=C12)CCCCCCCCCCBr QAWYYDMAJXVMFW-UHFFFAOYSA-N 0.000 description 1
- ODCMOZLVFHHLMY-UHFFFAOYSA-N 1-(2-hydroxyethoxy)hexan-2-ol Chemical compound CCCCC(O)COCCO ODCMOZLVFHHLMY-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- WSXIDSNEEOYBFA-UHFFFAOYSA-N 1-bromopent-1-ene Chemical compound CCCC=CBr WSXIDSNEEOYBFA-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- ZABMHLDQFJHDSC-UHFFFAOYSA-N 2,3-dihydro-1,3-oxazole Chemical group C1NC=CO1 ZABMHLDQFJHDSC-UHFFFAOYSA-N 0.000 description 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- VTWDKFNVVLAELH-UHFFFAOYSA-N 2-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical group C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- QMDFJHAAWUGVKQ-UHFFFAOYSA-N 2h-thiopyran Chemical group C1SC=CC=C1 QMDFJHAAWUGVKQ-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- TVWODOZDAKZGTA-UHFFFAOYSA-N C1(CCC1)C1C=CC2=CC=CC=C12 Chemical compound C1(CCC1)C1C=CC2=CC=CC=C12 TVWODOZDAKZGTA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 102000009123 Fibrin Human genes 0.000 description 1
- 108010073385 Fibrin Proteins 0.000 description 1
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 241000545744 Hirudinea Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
- G11B7/2534—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polycarbonates [PC]
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
- G11B7/2535—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polyesters, e.g. PET, PETG or PEN
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/146—Laser beam
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004222239 | 2004-07-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200613409A TW200613409A (en) | 2006-05-01 |
| TWI360563B true TWI360563B (OSRAM) | 2012-03-21 |
Family
ID=35786060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094119716A TW200613409A (en) | 2004-07-29 | 2005-06-14 | Optical recording material and optical recording medium |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7674569B2 (OSRAM) |
| EP (1) | EP1772282B1 (OSRAM) |
| JP (1) | JP4679520B2 (OSRAM) |
| KR (1) | KR101099292B1 (OSRAM) |
| CN (1) | CN100581837C (OSRAM) |
| TW (1) | TW200613409A (OSRAM) |
| WO (1) | WO2006011306A1 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9467134B2 (en) | 2014-05-28 | 2016-10-11 | Nuvoton Technology Corporation | Pulse width modulation control unit, voltage regulator and control method thereof |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3698708B2 (ja) * | 2003-08-07 | 2005-09-21 | 旭電化工業株式会社 | シアニン化合物、光学記録材料及び光学記録媒体 |
| JP3708094B2 (ja) * | 2003-08-07 | 2005-10-19 | 旭電化工業株式会社 | シアニン化合物、光学記録材料及び光学記録媒体 |
| KR101099292B1 (ko) * | 2004-07-29 | 2011-12-26 | 가부시키가이샤 아데카 | 광학 기록 재료 및 광학 기록 매체 |
| JP4640769B2 (ja) * | 2004-10-07 | 2011-03-02 | 株式会社Adeka | シアニン化合物及び光学記録材料 |
| JP4381958B2 (ja) * | 2004-10-27 | 2009-12-09 | ソニー株式会社 | 光記録媒体及びこれを用いた光記録再生方法 |
| JP4688480B2 (ja) * | 2004-11-25 | 2011-05-25 | 株式会社Adeka | シアニン化合物、該化合物を用いた光学記録材料、及び光学記録媒体 |
| JP2006305920A (ja) * | 2005-04-28 | 2006-11-09 | Tdk Corp | 光記録材料、光記録材料溶液並びに光記録媒体及びその製造方法 |
| JP2007090576A (ja) * | 2005-09-27 | 2007-04-12 | Tdk Corp | 光記録材料及び光記録媒体 |
| JP4953645B2 (ja) * | 2006-01-27 | 2012-06-13 | ソニー株式会社 | 光記録媒体及びその製造方法 |
| JP5078877B2 (ja) * | 2006-03-31 | 2012-11-21 | 株式会社Ａｄｅｋａ | シアニン化合物及び光学記録材料 |
| JP5100635B2 (ja) * | 2006-03-31 | 2012-12-19 | 株式会社Ａｄｅｋａ | インドリウム化合物及び光学記録材料 |
| JP4808085B2 (ja) * | 2006-06-09 | 2011-11-02 | 株式会社Ａｄｅｋａ | 光学記録材料 |
| AU2007305269A1 (en) * | 2006-10-04 | 2008-04-10 | Schering Corporation | Bicyclic and tricyclic derivatives as thrombin receptor antagonists |
| JP5086027B2 (ja) * | 2007-10-15 | 2012-11-28 | 株式会社Ａｄｅｋａ | インドリウム化合物及び該化合物を用いた光学記録材料 |
| JP5551089B2 (ja) | 2008-12-25 | 2014-07-16 | 株式会社Ａｄｅｋａ | シアニン化合物を用いた近赤外線吸収材料及びシアニン化合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2233511A (en) * | 1937-11-20 | 1941-03-04 | Eastman Kodak Co | 1,1'-diaralkyl-4,4'-carbocyanine salts |
| US2535995A (en) * | 1949-04-30 | 1950-12-26 | Gen Aniline & Film Corp | Photographic emulsions containing trinuclear cyanine dyes |
| NL129568C (OSRAM) * | 1964-04-20 | |||
| US3970461A (en) * | 1970-10-01 | 1976-07-20 | Fuji Photo Film Co., Ltd. | Fogged, direct-positive silver halide emulsion containing carbocyanine dye having indolenine nucleus |
| JPS526617B1 (OSRAM) * | 1970-12-29 | 1977-02-23 | ||
| US5246814A (en) * | 1982-04-06 | 1993-09-21 | Canon Kabushiki Kaisha | Process for recording on optical recording medium |
| US4490463A (en) * | 1983-03-03 | 1984-12-25 | Eastman Kodak Company | Alkanediyl bridged benzimidazolo monomethine cyanine dyes, processes for their preparation, and photographic emulsions and elements containing such dyes |
| JPS60118833A (ja) * | 1983-11-30 | 1985-06-26 | Fuji Photo Film Co Ltd | ハロゲン化銀写真乳剤 |
| JPS60234892A (ja) | 1984-05-08 | 1985-11-21 | Tdk Corp | 光記録媒体 |
| US4735839A (en) * | 1985-07-10 | 1988-04-05 | Ricoh Co., Ltd. | Optical information recording medium |
| US4889410A (en) | 1988-09-06 | 1989-12-26 | Eastman Kodak Company | Magenta filters |
| US5268478A (en) | 1990-11-30 | 1993-12-07 | Teijin Limited | Sulfur compound-coordinate bonded organic coloring matter, compositions of same, and photorecording media containing same |
| JPH05173282A (ja) * | 1991-12-24 | 1993-07-13 | Oji Paper Co Ltd | シート状光記録材料 |
| JPH06239028A (ja) | 1993-02-17 | 1994-08-30 | Canon Inc | 光記録媒体およびその製造方法 |
| JP3485227B2 (ja) | 1996-03-21 | 2004-01-13 | 住友精化株式会社 | 置換ベンゼンジチオール金属錯体およびその製造方法 |
| US6063467A (en) * | 1997-02-24 | 2000-05-16 | Fuji Electric Co., Ltd. | Optical recording medium |
| JP2000033775A (ja) * | 1998-07-17 | 2000-02-02 | Taiyo Yuden Co Ltd | 光情報記録媒体 |
| US20030224293A1 (en) * | 1999-08-04 | 2003-12-04 | Asahi Denka Kogyo Kabushiki Kaisha | Optical recording material |
| JP4467206B2 (ja) | 2000-06-01 | 2010-05-26 | 株式会社Ａｄｅｋａ | 光学記録材料 |
| JP2002293844A (ja) * | 2001-03-29 | 2002-10-09 | Fuji Photo Film Co Ltd | 光重合性組成物及び記録材料 |
| JP3659922B2 (ja) * | 2002-02-12 | 2005-06-15 | 旭電化工業株式会社 | 光学記録材料 |
| JP4056295B2 (ja) * | 2002-05-20 | 2008-03-05 | 株式会社Ａｄｅｋａ | 光学記録材料 |
| JP4173699B2 (ja) * | 2002-07-18 | 2008-10-29 | 株式会社Ａｄｅｋａ | 光学フィルター用光吸収剤及び光学フィルター |
| JP3708094B2 (ja) * | 2003-08-07 | 2005-10-19 | 旭電化工業株式会社 | シアニン化合物、光学記録材料及び光学記録媒体 |
| JP3698708B2 (ja) | 2003-08-07 | 2005-09-21 | 旭電化工業株式会社 | シアニン化合物、光学記録材料及び光学記録媒体 |
| JP4255359B2 (ja) * | 2003-10-31 | 2009-04-15 | ソニー株式会社 | 光記録媒体及び光記録再生方法 |
| KR101099292B1 (ko) * | 2004-07-29 | 2011-12-26 | 가부시키가이샤 아데카 | 광학 기록 재료 및 광학 기록 매체 |
| JP4640769B2 (ja) * | 2004-10-07 | 2011-03-02 | 株式会社Adeka | シアニン化合物及び光学記録材料 |
| JP4986457B2 (ja) * | 2005-04-05 | 2012-07-25 | 株式会社Ａｄｅｋａ | シアニン化合物、光学フィルター及び光学記録材料 |
| JP5078877B2 (ja) * | 2006-03-31 | 2012-11-21 | 株式会社Ａｄｅｋａ | シアニン化合物及び光学記録材料 |
-
2005
- 2005-06-07 KR KR1020077000702A patent/KR101099292B1/ko not_active Expired - Fee Related
- 2005-06-07 JP JP2006528449A patent/JP4679520B2/ja not_active Expired - Fee Related
- 2005-06-07 US US11/632,643 patent/US7674569B2/en not_active Expired - Fee Related
- 2005-06-07 CN CN200580025474A patent/CN100581837C/zh not_active Expired - Fee Related
- 2005-06-07 WO PCT/JP2005/010391 patent/WO2006011306A1/ja not_active Ceased
- 2005-06-07 EP EP05749072A patent/EP1772282B1/en not_active Expired - Lifetime
- 2005-06-14 TW TW094119716A patent/TW200613409A/zh not_active IP Right Cessation
-
2009
- 2009-12-03 US US12/630,285 patent/US20100080947A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9467134B2 (en) | 2014-05-28 | 2016-10-11 | Nuvoton Technology Corporation | Pulse width modulation control unit, voltage regulator and control method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| US7674569B2 (en) | 2010-03-09 |
| EP1772282A1 (en) | 2007-04-11 |
| TW200613409A (en) | 2006-05-01 |
| US20100080947A1 (en) | 2010-04-01 |
| EP1772282B1 (en) | 2012-02-01 |
| JPWO2006011306A1 (ja) | 2008-05-01 |
| CN1993234A (zh) | 2007-07-04 |
| US20080033179A1 (en) | 2008-02-07 |
| CN100581837C (zh) | 2010-01-20 |
| KR20070044431A (ko) | 2007-04-27 |
| EP1772282A4 (en) | 2009-08-12 |
| KR101099292B1 (ko) | 2011-12-26 |
| JP4679520B2 (ja) | 2011-04-27 |
| WO2006011306A1 (ja) | 2006-02-02 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |