RU2632030C2 - Люминесцентный комплекс лантанида и изделия и чернила, содержащие такой люминесцентный комплекс - Google Patents
Люминесцентный комплекс лантанида и изделия и чернила, содержащие такой люминесцентный комплекс Download PDFInfo
- Publication number
- RU2632030C2 RU2632030C2 RU2015115877A RU2015115877A RU2632030C2 RU 2632030 C2 RU2632030 C2 RU 2632030C2 RU 2015115877 A RU2015115877 A RU 2015115877A RU 2015115877 A RU2015115877 A RU 2015115877A RU 2632030 C2 RU2632030 C2 RU 2632030C2
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- Russia
- Prior art keywords
- complex
- paragraphs
- ink composition
- aqueous ink
- lanthanide
- Prior art date
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- 239000000203 mixture Substances 0.000 claims abstract description 87
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 20
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 14
- 229910052693 Europium Inorganic materials 0.000 claims abstract description 12
- 150000001768 cations Chemical class 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000000126 substance Substances 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
- 239000012634 fragment Substances 0.000 claims abstract description 6
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 54
- 150000002602 lanthanoids Chemical class 0.000 claims description 54
- 239000000047 product Substances 0.000 claims description 27
- -1 alkali metal cations Chemical group 0.000 claims description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 21
- 239000000975 dye Substances 0.000 claims description 21
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 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
- 239000000049 pigment Substances 0.000 claims description 12
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 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
- 238000007641 inkjet printing Methods 0.000 claims description 8
- 238000004806 packaging method and process Methods 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
- 150000003839 salts Chemical class 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
- 239000002253 acid Substances 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 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 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
- 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
- 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 compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 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
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 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
- 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
- 150000003841 chloride salts Chemical class 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 238000001748 luminescence spectrum Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000001681 protective effect Effects 0.000 abstract description 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 62
- 239000000243 solution Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 238000007639 printing Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 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
- 238000005345 coagulation Methods 0.000 description 4
- 230000015271 coagulation Effects 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 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
- 239000011230 binding agent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910021644 lanthanide ion Inorganic materials 0.000 description 3
- 230000002028 premature Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum 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
- 241000219991 Lythraceae Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000014360 Punica granatum Nutrition 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000000354 decomposition 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
- 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
- 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
- 238000005187 foaming Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 238000007644 letterpress printing Methods 0.000 description 1
- 239000000463 material Substances 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
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052566 spinel group Inorganic materials 0.000 description 1
- 238000013112 stability test 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
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical class [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 (2)
| Publication Number | Publication Date |
|---|---|
| RU2015115877A RU2015115877A (ru) | 2016-11-20 |
| RU2632030C2 true RU2632030C2 (ru) | 2017-10-02 |
Family
ID=49223730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015115877A RU2632030C2 (ru) | 2012-09-28 | 2013-09-09 | Люминесцентный комплекс лантанида и изделия и чернила, содержащие такой люминесцентный комплекс |
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) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US10107756B2 (en) * | 2016-01-12 | 2018-10-23 | Ecolab Usa Inc. | Fluorescence assay for quantification of picolinate and other compounds in oxidizers and oxidizing compositions |
| DE102016008804A1 (de) * | 2016-07-20 | 2018-01-25 | Giesecke+Devrient Currency Technology Gmbh | Sicherheitsmerkmal und Wertdokument |
| WO2019053963A1 (ja) * | 2017-09-15 | 2019-03-21 | 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 |
| 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 |
| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6402986B1 (en) * | 1999-07-16 | 2002-06-11 | The Trustees Of Boston University | Compositions and methods for luminescence lifetime comparison |
| EP2096499A1 (en) * | 2008-02-26 | 2009-09-02 | Xerox Corporation | Toner compositions |
| WO2010130681A1 (en) * | 2009-05-12 | 2010-11-18 | Sicpa Holding Sa | Secure document comprising luminescent chelates |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE136925T1 (de) * | 1992-02-14 | 1996-05-15 | Amersham Int Plc | Fluoreszente verbindungen |
| US5542971A (en) | 1994-12-01 | 1996-08-06 | Pitney Bowes | Bar codes using luminescent invisible inks |
| JP3949163B2 (ja) * | 1995-01-06 | 2007-07-25 | 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 | 摩擦ルミネセンスランタニド▲上ｉｉｉ▼錯塩 |
| AU714019B2 (en) | 1995-09-15 | 1999-12-16 | Videojet Systems International, Inc. | Invisible fluorescent jet ink |
| JP2000109734A (ja) * | 1998-10-06 | 2000-04-18 | Ricoh Co Ltd | 水性インクおよびそれを用いたインクジェット記録方法 |
| JP4065617B2 (ja) * | 1998-12-01 | 2008-03-26 | 株式会社リコー | 記録用インクおよび該インクを使用した記録方法 |
| US6565770B1 (en) | 2000-11-17 | 2003-05-20 | Flex Products, Inc. | Color-shifting pigments and foils with luminescent coatings |
| EP1288265A1 (en) | 2001-08-28 | 2003-03-05 | Sicpa Holding S.A. | Ink composition comprising optically variable pigments, use of the composition, optically variable pigment and method of treating said pigment |
| US7108742B2 (en) | 2002-02-26 | 2006-09-19 | Ciba Specialty Chemicals Corporation | Ink compositions containing lanthanide complexes |
| US6905538B2 (en) | 2002-12-30 | 2005-06-14 | Pitney Bowes Inc. | Invisible ink jet inks |
| TW200639854A (en) * | 2003-03-24 | 2006-11-16 | Mitsubishi Kagaku Media Co Ltd | Phase-change recording material and information recording medium |
| KR100601641B1 (ko) | 2003-08-08 | 2006-07-14 | 삼성전자주식회사 | 비피리딘계 금속 착화합물 및 이를 포함하는 잉크 조성물 |
| CN1839417A (zh) | 2003-08-22 | 2006-09-27 | 纳幕尔杜邦公司 | 利用透明发光聚合物验证身份的方法 |
| US8916692B2 (en) | 2003-11-07 | 2014-12-23 | Robert C. Leif | Reagent system and method for modifying the luminescence of lanthanide(III) macrocyclic complexes |
| KR100744351B1 (ko) | 2006-03-24 | 2007-07-30 | 삼성전자주식회사 | 자외선 발광 잉크 및 이를 이용한 보안장치 |
| RU2323955C1 (ru) | 2006-09-15 | 2008-05-10 | Андриевский Александр Михайлович | Водостойкий люминесцентный пигмент и люминесцентная печатная краска на его основе |
| US7922936B2 (en) | 2006-10-26 | 2011-04-12 | Cabot Corporation | Luminescent compositions, methods for making luminescent compositions and inks incorporating the same |
| FR2909095B1 (fr) | 2006-11-28 | 2009-02-20 | Imaje Sa Sa | Composition d'encre liquide fluorescente pour l'impression par jet d'encre. |
| DE102007005646A1 (de) | 2007-01-31 | 2008-08-07 | Henkel Ag & Co. Kgaa | Färbemittel, enthaltend durch sichtbares Licht anregbare Lumineszenzpigmente |
| US20080221328A1 (en) * | 2007-03-05 | 2008-09-11 | Jan Reedijk | Luminescent lanthanide complexes |
| JP2008239660A (ja) * | 2007-03-26 | 2008-10-09 | Seiko Epson Corp | インクジェット記録用インク |
| US20080306250A1 (en) | 2007-06-08 | 2008-12-11 | Reardon Damien F | Rare-earth amidate chelates |
| US9834660B2 (en) | 2007-06-28 | 2017-12-05 | Honeywell International Inc. | Rare earth metal complexes that excite in the long UV wavelength range |
| US8889839B2 (en) * | 2008-05-07 | 2014-11-18 | Syracuse University | Pyridine-bis (oxazoline)(“pybox”) moiety as a chelator and sensitizer for lanthanide ion (Ln (III)) Luminescence |
-
2013
- 2013-09-09 JP JP2015533515A patent/JP2015537061A/ja active Pending
- 2013-09-09 HK HK15112089.0A patent/HK1211265A1/xx unknown
- 2013-09-09 IN IN1013DEN2015 patent/IN2015DN01013A/en unknown
- 2013-09-09 CA CA2881728A patent/CA2881728A1/en not_active Abandoned
- 2013-09-09 WO PCT/EP2013/068570 patent/WO2014048702A1/en not_active Ceased
- 2013-09-09 RU RU2015115877A patent/RU2632030C2/ru active
- 2013-09-09 AU AU2013323027A patent/AU2013323027B2/en active Active
- 2013-09-09 CN CN201380050154.5A patent/CN104703805B/zh active 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 KR KR1020157008952A patent/KR20150065714A/ko not_active Withdrawn
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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
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6402986B1 (en) * | 1999-07-16 | 2002-06-11 | The Trustees Of Boston University | Compositions and methods for luminescence lifetime comparison |
| EP2096499A1 (en) * | 2008-02-26 | 2009-09-02 | Xerox Corporation | Toner compositions |
| WO2010130681A1 (en) * | 2009-05-12 | 2010-11-18 | Sicpa Holding Sa | Secure document comprising luminescent chelates |
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| AU2013323027B2 (en) | 2017-03-02 |
| AU2013323027A1 (en) | 2015-02-26 |
| WO2014048702A1 (en) | 2014-04-03 |
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| US20140093664A1 (en) | 2014-04-03 |
| AR092708A1 (es) | 2015-04-29 |
| PH12015500484A1 (en) | 2015-04-20 |
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| JP2015537061A (ja) | 2015-12-24 |
| MX347496B (es) | 2017-04-28 |
| CN104703805B (zh) | 2016-12-28 |
| US9163155B2 (en) | 2015-10-20 |
| IL237094A (en) | 2015-11-30 |
| MX2013010950A (es) | 2014-09-02 |
| ES2598053T3 (es) | 2017-01-25 |
| HK1211265A1 (en) | 2016-05-20 |
| CA2881728A1 (en) | 2014-04-03 |
| KR20150065714A (ko) | 2015-06-15 |
| IN2015DN01013A (enExample) | 2015-06-26 |
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