DE69725607T2 - Polymethin-komplex-farbstoffe und ihre verwendung - Google Patents
Polymethin-komplex-farbstoffe und ihre verwendung Download PDFInfo
- Publication number
- DE69725607T2 DE69725607T2 DE69725607T DE69725607T DE69725607T2 DE 69725607 T2 DE69725607 T2 DE 69725607T2 DE 69725607 T DE69725607 T DE 69725607T DE 69725607 T DE69725607 T DE 69725607T DE 69725607 T2 DE69725607 T2 DE 69725607T2
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- Germany
- Prior art keywords
- alkyl
- unsubstituted
- independently
- halogen
- alkoxy
- 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.)
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- -1 nitro, cyano, hydroxy, amino Chemical group 0.000 claims description 91
- 239000000975 dye Substances 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical group 0.000 claims description 42
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 28
- 230000003287 optical effect Effects 0.000 claims description 28
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052751 metal Chemical class 0.000 claims description 16
- 239000002184 metal Chemical class 0.000 claims description 16
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 14
- 239000003446 ligand Substances 0.000 claims description 14
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 10
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 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
- 229910052723 transition metal Inorganic materials 0.000 claims description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 4
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 150000002902 organometallic compounds Chemical class 0.000 claims description 4
- 229950000688 phenothiazine Drugs 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 3
- 229940031826 phenolate Drugs 0.000 claims description 3
- 238000003860 storage Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 claims description 2
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 claims description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 2
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 claims description 2
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims description 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims description 2
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 239000010410 layer Substances 0.000 description 67
- 238000010521 absorption reaction Methods 0.000 description 34
- 239000000203 mixture Substances 0.000 description 26
- 239000000463 material Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 230000005855 radiation Effects 0.000 description 11
- 239000011241 protective layer Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 7
- 150000001768 cations Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 4
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- BNDRWEVUODOUDW-UHFFFAOYSA-N 3-Hydroxy-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)O BNDRWEVUODOUDW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Chemical group 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000002310 reflectometry Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UNBOSJFEZZJZLR-UHFFFAOYSA-N 4-(4-nitrophenylazo)aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 UNBOSJFEZZJZLR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- 241001589086 Bellapiscis medius Species 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- 229910052689 Holmium Inorganic materials 0.000 description 1
- 229910052765 Lutetium Inorganic materials 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
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- G11B2007/25705—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials
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- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
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- G11B7/257—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers
- G11B2007/25705—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials
- G11B2007/25716—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 layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials containing sulfur
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- 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
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- 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
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- G11—INFORMATION STORAGE
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- 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]
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- 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
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- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
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- 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
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- G11B7/2542—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 protective topcoat layers consisting essentially of organic resins
-
- G—PHYSICS
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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
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- G11B7/258—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 reflective layers
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- 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
- G11B7/258—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 reflective layers
- G11B7/2595—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 reflective layers based on gold
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- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH314096 | 1996-12-20 | ||
| CH314096 | 1996-12-20 | ||
| PCT/EP1997/006912 WO1998028737A1 (en) | 1996-12-20 | 1997-12-11 | Complex polymethine dyes and their use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69725607D1 DE69725607D1 (de) | 2003-11-20 |
| DE69725607T2 true DE69725607T2 (de) | 2004-08-05 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69725607T Expired - Fee Related DE69725607T2 (de) | 1996-12-20 | 1997-12-11 | Polymethin-komplex-farbstoffe und ihre verwendung |
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| Country | Link |
|---|---|
| US (2) | US5958650A (enExample) |
| EP (1) | EP0946941B1 (enExample) |
| JP (1) | JP2001506933A (enExample) |
| KR (2) | KR100468941B1 (enExample) |
| CN (1) | CN1147846C (enExample) |
| AU (1) | AU5561198A (enExample) |
| BR (1) | BR9714232A (enExample) |
| CA (1) | CA2271079A1 (enExample) |
| DE (1) | DE69725607T2 (enExample) |
| TW (1) | TW503342B (enExample) |
| WO (1) | WO1998028737A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2000043420A (ja) * | 1998-08-03 | 2000-02-15 | Ricoh Co Ltd | 光記録媒体 |
| DE19932902A1 (de) | 1999-07-12 | 2001-01-25 | Beiersdorf Ag | Datenspeicher |
| WO2001019923A1 (en) * | 1999-09-14 | 2001-03-22 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Styryl dye |
| US6500510B1 (en) | 1999-11-04 | 2002-12-31 | Molecular Storage Technologies, Inc. | Molecular level optical information storage devices |
| JP4754698B2 (ja) * | 2000-02-10 | 2011-08-24 | 株式会社林原生物化学研究所 | シアニン色素 |
| JP4666869B2 (ja) * | 2000-02-23 | 2011-04-06 | 株式会社林原生物化学研究所 | シアニン色素 |
| DE10008328A1 (de) * | 2000-02-23 | 2002-01-31 | Tesa Ag | Datenspeicher |
| DE10028113A1 (de) * | 2000-06-07 | 2001-12-20 | Beiersdorf Ag | Datenspeicher |
| DE10039370A1 (de) * | 2000-08-11 | 2002-02-28 | Eml Europ Media Lab Gmbh | Holographischer Datenspeicher |
| DE10039372C2 (de) * | 2000-08-11 | 2003-05-15 | Tesa Scribos Gmbh | Holographischer Datenspeicher |
| DE10039374A1 (de) * | 2000-08-11 | 2002-02-21 | Eml Europ Media Lab Gmbh | Holographischer Datenspeicher |
| DE10060235A1 (de) * | 2000-12-05 | 2002-06-13 | Tesa Ag | Verwendung eines Packbands als holographischer Datenträger |
| JP4173735B2 (ja) * | 2000-12-19 | 2008-10-29 | 株式会社林原生物化学研究所 | 光吸収剤 |
| KR100766474B1 (ko) * | 2000-12-20 | 2007-10-15 | 교와 핫꼬 케미칼 가부시키가이샤 | 금속착체형 스쿠아리리움 화합물 및 이를 이용한 광기록매체 |
| JP3989846B2 (ja) * | 2001-03-21 | 2007-10-10 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 高い記憶密度を有する光学記録材料 |
| DE10128902A1 (de) * | 2001-06-15 | 2003-10-16 | Tesa Scribos Gmbh | Holographischer Datenspeicher |
| DE10128901A1 (de) * | 2001-06-15 | 2002-12-19 | Tesa Ag | Verfahren zum Eingeben von Information in einen optisch beschreibbaren und auslesbaren Datenspeicher |
| TW200406466A (en) * | 2001-11-13 | 2004-05-01 | Ciba Sc Holding Ag | Compositions comprising at least one oxonol dye and at least one metal complex |
| DE10156793A1 (de) * | 2001-11-19 | 2003-10-09 | Tesa Scribos Gmbh | Sicherheitsklebeband |
| CA2483836A1 (en) * | 2002-04-29 | 2003-11-13 | Ciba Specialty Chemicals Holding Inc. | Compositions and methods for imparting improved rheology on pigment based inks and paints |
| WO2004079732A1 (en) * | 2003-03-03 | 2004-09-16 | Ciba Specialty Chemicals Holding Inc. | Optical recording materials having high storage density |
| CN100388017C (zh) * | 2003-06-30 | 2008-05-14 | 富士电机控股株式会社 | 蓝色滤色器及使用该蓝色滤色器的有机电致发光元件 |
| EP1514906A1 (en) * | 2003-09-11 | 2005-03-16 | Clariant International Ltd. | Lightfast cyanine dye compositions for optical data recording |
| EP1719126A1 (en) * | 2004-02-23 | 2006-11-08 | CIBA SPECIALTY CHEMICALS HOLDING INC. Patent Departement | Optical recording materials having high storage density |
| US8350015B2 (en) * | 2004-02-27 | 2013-01-08 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Cyanine dye |
| JP4393236B2 (ja) * | 2004-03-15 | 2010-01-06 | 富士フイルム株式会社 | 硬化性組成物及びそれを用いた画像形成材料 |
| JP4482701B2 (ja) * | 2004-04-13 | 2010-06-16 | 株式会社東芝 | 追記型情報記録媒体 |
| JP2005297406A (ja) * | 2004-04-13 | 2005-10-27 | Toshiba Corp | 媒体用記録材料 |
| ATE352587T1 (de) * | 2004-07-29 | 2007-02-15 | Clariant Finance Bvi Ltd | Azoliganden auf der basis von aminoantipyrine und ihre metallkomplexe zur verwendung als optische aufzeichnungsmedien |
| EP1624029A1 (en) * | 2004-08-05 | 2006-02-08 | Clariant International Ltd. | New Pyridinium imine based dyes and their use in optical layers for optical data recording |
| 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 |
| US7430158B1 (en) | 2004-12-13 | 2008-09-30 | Chris Tanner | Music player with adjustable pitch controller |
| KR100756166B1 (ko) * | 2005-03-17 | 2007-09-05 | 주식회사 엘지화학 | 피롤 유도체를 함유하는 시아닌계 색소 |
| 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 |
| WO2007128691A1 (en) * | 2006-05-05 | 2007-11-15 | Ciba Holding Inc. | High capacity optical storage media comprising organometallic ion pairs |
| CN101443197B (zh) * | 2006-05-23 | 2012-03-07 | 株式会社艾迪科 | 光学记录材料及花青化合物 |
| JP2007323719A (ja) * | 2006-05-31 | 2007-12-13 | Toshiba Corp | 光ディスク、情報記録方法、情報再生方法 |
| JP2008012884A (ja) * | 2006-07-10 | 2008-01-24 | Taiyo Yuden Co Ltd | 光情報記録媒体およびその製造方法 |
| US20100047509A1 (en) * | 2008-07-30 | 2010-02-25 | Industrial Technology Research Institute | Organic dye compound and high density optical recording medium including the same |
| TWI518143B (zh) * | 2011-03-31 | 2016-01-21 | Sumitomo Chemical Co | Dye with salt |
| JP2015063631A (ja) * | 2013-09-26 | 2015-04-09 | 日本化薬株式会社 | アゾ化合物 |
| EP2944326B1 (en) * | 2014-05-16 | 2018-11-21 | Cyanagen Srl | Tricarbocyanine-cyclodextrin-conjugates and their use for the diagnosis of kidney diseases |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH316749A (de) * | 1953-04-02 | 1956-10-31 | Ciba Geigy | Verfahren zur Herstellung neuer Umwandlungsprodukte komplex gebundenes Metall enthaltender Azofarbstoffe |
| CH430942A (de) * | 1961-10-16 | 1967-02-28 | Ciba Geigy | Metallhaltige Farbstoffpräparate und Verfahren zu deren Herstellung |
| NL129233C (enExample) * | 1965-01-15 | |||
| US5219707A (en) * | 1983-01-12 | 1993-06-15 | Tdk Corporation | Photostable cyanine dye and optical recording medium |
| DE3467379D1 (en) * | 1983-01-13 | 1987-12-17 | Ciba Geigy Ag | Process for dyeing or printing polyamide fibres |
| US4626496A (en) * | 1984-06-19 | 1986-12-02 | Ricoh Co., Ltd. | Optical information recording medium |
| JPH0255189A (ja) * | 1988-08-18 | 1990-02-23 | Matsushita Electric Ind Co Ltd | 光記録媒体 |
| JPH0351182A (ja) * | 1989-07-19 | 1991-03-05 | Matsushita Electric Ind Co Ltd | 光記録媒体 |
| JPH03150189A (ja) * | 1989-11-08 | 1991-06-26 | Fuji Photo Film Co Ltd | 情報記録媒体及び光情報記録方法 |
| JP2699120B2 (ja) * | 1989-12-22 | 1998-01-19 | 富士写真フイルム株式会社 | 情報記録媒体および光情報記録方法 |
| WO1991018950A1 (en) * | 1990-05-25 | 1991-12-12 | Mitsubishi Kasei Corporation | Dye composition and optical recording medium |
| JP3026358B2 (ja) * | 1990-10-09 | 2000-03-27 | パイオニア株式会社 | 光記録媒体 |
| JP3168469B2 (ja) * | 1991-04-05 | 2001-05-21 | 三菱化学株式会社 | 光学記録媒体 |
| EP0528512A1 (en) * | 1991-08-20 | 1993-02-24 | Pioneer Electronic Corporation | Recording medium |
| JPH05147356A (ja) * | 1991-11-28 | 1993-06-15 | Ricoh Co Ltd | 光記録媒体 |
| JP3481620B2 (ja) * | 1992-04-23 | 2003-12-22 | イーストマン コダック カンパニー | シアニンir染料用安定剤 |
| US5426015A (en) * | 1993-10-18 | 1995-06-20 | Eastman Kodak Company | Metallized azo dianion with two cationic dye counter ions for optical information recording medium |
| JPH07186547A (ja) * | 1993-10-21 | 1995-07-25 | Eastman Kodak Co | 光学記録層用色素混合物 |
| US5633106A (en) * | 1994-04-08 | 1997-05-27 | Mitsui Toatsu Chemicals, Inc. | Optical recording media and a method of recording and reproducing information |
| US5547728A (en) * | 1994-09-23 | 1996-08-20 | Eastman Kodak Company | Optical recording elements having recording layers containing mixtures of formazan and cyanine dyes |
| US5547727A (en) * | 1994-12-13 | 1996-08-20 | Eastman Kodak Company | Optical recording elements having recording layers containing cationic azo dyes |
| JPH091934A (ja) * | 1995-06-16 | 1997-01-07 | Ricoh Co Ltd | 光情報記録媒体 |
| US6361922B1 (en) * | 1996-10-16 | 2002-03-26 | Eastman Kodak Company | Thicker optical recording layers comprising a tetra dye having a metallized azo dianionic dye with cationic dye counterions |
| US5821029A (en) * | 1997-06-25 | 1998-10-13 | Eastman Kodak Company | Optical recording elements containing mixtures of metallized carbamoylazo and cyanine dyes |
| JP3051182U (ja) | 1998-02-05 | 1998-08-11 | 有限会社誉商事 | アイロン用装着カバー |
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1997
- 1997-12-11 DE DE69725607T patent/DE69725607T2/de not_active Expired - Fee Related
- 1997-12-11 KR KR10-2004-7014893A patent/KR100468941B1/ko not_active Expired - Fee Related
- 1997-12-11 EP EP97952050A patent/EP0946941B1/en not_active Expired - Lifetime
- 1997-12-11 KR KR10-1999-7005536A patent/KR100479369B1/ko not_active Expired - Fee Related
- 1997-12-11 JP JP52830798A patent/JP2001506933A/ja not_active Ceased
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- 1997-12-11 AU AU55611/98A patent/AU5561198A/en not_active Abandoned
- 1997-12-11 CN CNB971807159A patent/CN1147846C/zh not_active Expired - Fee Related
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1999
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Also Published As
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|---|---|
| CA2271079A1 (en) | 1998-07-02 |
| US5962657A (en) | 1999-10-05 |
| KR20000069578A (ko) | 2000-11-25 |
| JP2001506933A (ja) | 2001-05-29 |
| EP0946941B1 (en) | 2003-10-15 |
| BR9714232A (pt) | 2000-04-18 |
| EP0946941A1 (en) | 1999-10-06 |
| DE69725607D1 (de) | 2003-11-20 |
| CN1147846C (zh) | 2004-04-28 |
| US5958650A (en) | 1999-09-28 |
| WO1998028737A1 (en) | 1998-07-02 |
| TW503342B (en) | 2002-09-21 |
| KR20040097197A (ko) | 2004-11-17 |
| KR100468941B1 (ko) | 2005-02-07 |
| AU5561198A (en) | 1998-07-17 |
| CN1240530A (zh) | 2000-01-05 |
| KR100479369B1 (ko) | 2005-03-30 |
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