JP2015537061A - 発光性ランタニド錯体並びに該発光性錯体を含有する物品及びインク - Google Patents
発光性ランタニド錯体並びに該発光性錯体を含有する物品及びインク Download PDFInfo
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- JP2015537061A JP2015537061A JP2015533515A JP2015533515A JP2015537061A JP 2015537061 A JP2015537061 A JP 2015537061A JP 2015533515 A JP2015533515 A JP 2015533515A JP 2015533515 A JP2015533515 A JP 2015533515A JP 2015537061 A JP2015537061 A JP 2015537061A
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- inkjet ink
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- 229910052747 lanthanoid Inorganic materials 0.000 title claims abstract description 50
- 150000002602 lanthanoids Chemical class 0.000 title claims abstract description 50
- 239000000203 mixture Substances 0.000 claims abstract description 86
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 22
- -1 rare earth cations Chemical class 0.000 claims abstract description 15
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 15
- 229910052693 Europium Inorganic materials 0.000 claims abstract description 12
- 229910052771 Terbium Inorganic materials 0.000 claims abstract description 11
- 229910052684 Cerium Inorganic materials 0.000 claims abstract description 7
- 229910052692 Dysprosium Inorganic materials 0.000 claims abstract description 7
- 229910052691 Erbium Inorganic materials 0.000 claims abstract description 7
- 229910052688 Gadolinium Inorganic materials 0.000 claims abstract description 7
- 229910052689 Holmium Inorganic materials 0.000 claims abstract description 7
- 229910052779 Neodymium Inorganic materials 0.000 claims abstract description 7
- 229910052777 Praseodymium Inorganic materials 0.000 claims abstract description 7
- 229910052772 Samarium Inorganic materials 0.000 claims abstract description 7
- 229910052775 Thulium Inorganic materials 0.000 claims abstract description 7
- 229910052769 Ytterbium Inorganic materials 0.000 claims abstract description 7
- 239000000975 dye Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 239000000049 pigment Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 229910001868 water Inorganic materials 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- 238000004806 packaging method and process Methods 0.000 claims description 8
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 8
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical group CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 7
- 229910021644 lanthanide ion Inorganic materials 0.000 claims description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 6
- XTLJJHGQACAZMS-UHFFFAOYSA-N 4-oxo-1h-pyridine-2,6-dicarboxylic acid Chemical compound OC(=O)C1=CC(=O)C=C(C(O)=O)N1 XTLJJHGQACAZMS-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 6
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 5
- 229940015975 1,2-hexanediol Drugs 0.000 claims description 4
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims description 4
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical group C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- IMWUREPEYPRYOR-UHFFFAOYSA-N pyrrolidine-2-thione Chemical compound S=C1CCCN1 IMWUREPEYPRYOR-UHFFFAOYSA-N 0.000 claims description 4
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 4
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 4
- 150000003852 triazoles Chemical group 0.000 claims description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 239000011888 foil Substances 0.000 claims description 3
- 150000002334 glycols Chemical class 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 150000003138 primary alcohols Chemical group 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- 150000003333 secondary alcohols Chemical class 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 3
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 69
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000243 solution Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 11
- 238000001035 drying Methods 0.000 description 9
- 238000007639 printing Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000004020 luminiscence type Methods 0.000 description 6
- 238000007641 inkjet printing Methods 0.000 description 5
- 150000002910 rare earth metals Chemical class 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- IYUMNONNHYADBU-UHFFFAOYSA-N 4-chloropyridine-2,6-dicarboxylic acid Chemical compound OC(=O)C1=CC(Cl)=CC(C(O)=O)=N1 IYUMNONNHYADBU-UHFFFAOYSA-N 0.000 description 3
- HEUCIBREYIIVAV-UHFFFAOYSA-N 4-morpholin-4-ylpyridine-2,6-dicarboxylic acid Chemical compound OC(=O)C1=NC(C(=O)O)=CC(N2CCOCC2)=C1 HEUCIBREYIIVAV-UHFFFAOYSA-N 0.000 description 3
- LJFOMJKDLGQMEO-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine-2,6-dicarboxylic acid Chemical compound OC(=O)C1=NC(C(=O)O)=CC(N2CCCC2)=C1 LJFOMJKDLGQMEO-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000002028 premature Effects 0.000 description 3
- 230000009993 protective function Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000872198 Serjania polyphylla Species 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- IHEBMGYEECNNJH-UHFFFAOYSA-N 4-aminopyridine-2,6-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=NC(C(O)=O)=C1 IHEBMGYEECNNJH-UHFFFAOYSA-N 0.000 description 1
- JQEWFUITIOXUCQ-UHFFFAOYSA-N 4-ethoxypyridine-2,6-dicarboxylic acid Chemical compound CCOC1=CC(C(O)=O)=NC(C(O)=O)=C1 JQEWFUITIOXUCQ-UHFFFAOYSA-N 0.000 description 1
- INGKNNWONGEVCL-UHFFFAOYSA-N 4-methoxypyridine-2,6-dicarboxylic acid Chemical compound COC1=CC(C(O)=O)=NC(C(O)=O)=C1 INGKNNWONGEVCL-UHFFFAOYSA-N 0.000 description 1
- VIKMWFUHLRRONF-UHFFFAOYSA-N 4-propan-2-yloxypyridine-2,6-dicarboxylic acid Chemical compound CC(C)OC1=CC(C(O)=O)=NC(C(O)=O)=C1 VIKMWFUHLRRONF-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000002223 garnet Substances 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007644 letterpress printing Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/50—Sympathetic, colour changing or similar inks
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B44—DECORATIVE ARTS
- B44F—SPECIAL DESIGNS OR PICTURES
- B44F1/00—Designs or pictures characterised by special or unusual light effects
- B44F1/08—Designs or pictures characterised by special or unusual light effects characterised by colour effects
- B44F1/10—Changing, amusing, or secret pictures
-
- 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
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M3/00—Printing processes to produce particular kinds of printed work, e.g. patterns
- B41M3/14—Security printing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M3/00—Printing processes to produce particular kinds of printed work, e.g. patterns
- B41M3/14—Security printing
- B41M3/144—Security printing using fluorescent, luminescent or iridescent effects
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261707282P | 2012-09-28 | 2012-09-28 | |
| US61/707,282 | 2012-09-28 | ||
| EPPCT/EP2012/069666 | 2012-10-04 | ||
| EP2012069666 | 2012-10-04 | ||
| PCT/EP2013/068570 WO2014048702A1 (en) | 2012-09-28 | 2013-09-09 | Luminescent lanthanide complex, and articles and inks containing the luminescent complex |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2015537061A true JP2015537061A (ja) | 2015-12-24 |
Family
ID=49223730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015533515A Pending JP2015537061A (ja) | 2012-09-28 | 2013-09-09 | 発光性ランタニド錯体並びに該発光性錯体を含有する物品及びインク |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9163155B2 (enExample) |
| JP (1) | JP2015537061A (enExample) |
| KR (1) | KR20150065714A (enExample) |
| CN (1) | CN104703805B (enExample) |
| AR (1) | AR092708A1 (enExample) |
| AU (1) | AU2013323027B2 (enExample) |
| CA (1) | CA2881728A1 (enExample) |
| ES (1) | ES2598053T3 (enExample) |
| HK (1) | HK1211265A1 (enExample) |
| IL (1) | IL237094A (enExample) |
| IN (1) | IN2015DN01013A (enExample) |
| MX (1) | MX347496B (enExample) |
| PH (1) | PH12015500484A1 (enExample) |
| RU (1) | RU2632030C2 (enExample) |
| WO (1) | WO2014048702A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2019509496A (ja) * | 2016-01-12 | 2019-04-04 | エコラブ ユーエスエイ インク | 酸化剤及び酸化組成物中のピコリン酸塩及び他の化合物の定量化のための蛍光アッセイ |
| JP2020097671A (ja) * | 2018-12-18 | 2020-06-25 | 紀州技研工業株式会社 | インクジェットインク、判定方法及び印刷物 |
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| EP2993214A1 (de) * | 2014-09-03 | 2016-03-09 | Julius-Maximilians-Universität Würzburg | Verwendung einer Zusammensetzung für ein Packmittel |
| FR3031697B1 (fr) | 2015-01-16 | 2020-12-18 | Hologram Ind | Composant optique de securite. |
| DE102015006753A1 (de) | 2015-05-26 | 2016-12-01 | Giesecke & Devrient Gmbh | Tintenzusammensetzung, Verwendung derselben und Druckerzeugnis |
| DE102015109637B4 (de) | 2015-06-16 | 2019-05-09 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Superparamagnetische Mikropartikel, die mit feuchtigkeitsempfindlichen lumineszierenden Verbindungen belegt sind, Verfahren zur Herstellung, Verwendung und Arbeitsverfahren zur Detektion von Feuchtigkeit |
| DE102016008804A1 (de) | 2016-07-20 | 2018-01-25 | Giesecke+Devrient Currency Technology Gmbh | Sicherheitsmerkmal und Wertdokument |
| JP7081603B2 (ja) * | 2017-09-15 | 2022-06-07 | 大日本印刷株式会社 | インキ組成物、印刷物、及び、真贋判定方法 |
| CN112457719B (zh) * | 2020-11-24 | 2022-07-19 | 陕西科技大学 | 一种光致变色的荧光油性墨水及其制备方法 |
| CN112409846B (zh) * | 2020-11-24 | 2022-07-12 | 陕西科技大学 | 一种光致变色可喷墨打印水性荧光墨水及其制备方法 |
| AR130228A1 (es) | 2022-08-23 | 2024-11-20 | Sicpa Holding Sa | Composición de tinta de seguridad y característica de seguridad legible por máquina derivada de la misma |
| CN119019889B (zh) * | 2024-10-29 | 2025-02-14 | 当纳利(成都)印刷有限公司 | 可见长余辉-近红外双通荧光防伪油墨及其制备方法 |
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2013
- 2013-09-09 WO PCT/EP2013/068570 patent/WO2014048702A1/en not_active Ceased
- 2013-09-09 AU AU2013323027A patent/AU2013323027B2/en active Active
- 2013-09-09 CA CA2881728A patent/CA2881728A1/en not_active Abandoned
- 2013-09-09 RU RU2015115877A patent/RU2632030C2/ru active
- 2013-09-09 MX MX2013010950A patent/MX347496B/es active IP Right Grant
- 2013-09-09 ES ES13765299.6T patent/ES2598053T3/es active Active
- 2013-09-09 IN IN1013DEN2015 patent/IN2015DN01013A/en unknown
- 2013-09-09 JP JP2015533515A patent/JP2015537061A/ja active Pending
- 2013-09-09 KR KR1020157008952A patent/KR20150065714A/ko not_active Withdrawn
- 2013-09-09 HK HK15112089.0A patent/HK1211265A1/xx unknown
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- 2013-09-27 US US14/040,020 patent/US9163155B2/en active Active
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2015
- 2015-02-04 IL IL237094A patent/IL237094A/en not_active IP Right Cessation
- 2015-03-05 PH PH12015500484A patent/PH12015500484A1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019509496A (ja) * | 2016-01-12 | 2019-04-04 | エコラブ ユーエスエイ インク | 酸化剤及び酸化組成物中のピコリン酸塩及び他の化合物の定量化のための蛍光アッセイ |
| JP2020097671A (ja) * | 2018-12-18 | 2020-06-25 | 紀州技研工業株式会社 | インクジェットインク、判定方法及び印刷物 |
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| US20140093664A1 (en) | 2014-04-03 |
| WO2014048702A1 (en) | 2014-04-03 |
| AU2013323027A1 (en) | 2015-02-26 |
| AU2013323027B2 (en) | 2017-03-02 |
| KR20150065714A (ko) | 2015-06-15 |
| US9163155B2 (en) | 2015-10-20 |
| HK1211265A1 (en) | 2016-05-20 |
| ES2598053T3 (es) | 2017-01-25 |
| CN104703805B (zh) | 2016-12-28 |
| CA2881728A1 (en) | 2014-04-03 |
| MX347496B (es) | 2017-04-28 |
| RU2632030C2 (ru) | 2017-10-02 |
| MX2013010950A (es) | 2014-09-02 |
| CN104703805A (zh) | 2015-06-10 |
| PH12015500484A1 (en) | 2015-04-20 |
| AR092708A1 (es) | 2015-04-29 |
| IL237094A (en) | 2015-11-30 |
| RU2015115877A (ru) | 2016-11-20 |
| IN2015DN01013A (enExample) | 2015-06-26 |
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