NL8004876A - Organische zeldzame aardmetaalzoutfosfor. - Google Patents
Organische zeldzame aardmetaalzoutfosfor. Download PDFInfo
- Publication number
- NL8004876A NL8004876A NL8004876A NL8004876A NL8004876A NL 8004876 A NL8004876 A NL 8004876A NL 8004876 A NL8004876 A NL 8004876A NL 8004876 A NL8004876 A NL 8004876A NL 8004876 A NL8004876 A NL 8004876A
- Authority
- NL
- Netherlands
- Prior art keywords
- acid
- europium
- salt
- carboxylic acid
- phosphorus according
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims description 187
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 60
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 47
- 239000011574 phosphorus Substances 0.000 title claims description 47
- 229910052693 Europium Inorganic materials 0.000 claims description 97
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 94
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 92
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 70
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 64
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 58
- -1 rare earth metal salt Chemical class 0.000 claims description 49
- 229940114081 cinnamate Drugs 0.000 claims description 46
- 229930016911 cinnamic acid Natural products 0.000 claims description 46
- 235000013985 cinnamic acid Nutrition 0.000 claims description 46
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 39
- 229910052771 Terbium Inorganic materials 0.000 claims description 35
- 229910052751 metal Inorganic materials 0.000 claims description 34
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 34
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 33
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 28
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 26
- 229910052727 yttrium Inorganic materials 0.000 claims description 22
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 22
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 21
- 229910052746 lanthanum Inorganic materials 0.000 claims description 21
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 21
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 20
- 239000011575 calcium Substances 0.000 claims description 17
- 229910052712 strontium Inorganic materials 0.000 claims description 17
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 17
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 16
- 229910052791 calcium Inorganic materials 0.000 claims description 16
- 150000002910 rare earth metals Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 229910052788 barium Inorganic materials 0.000 claims description 13
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 13
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 claims description 13
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000000962 organic group Chemical group 0.000 claims description 10
- VLSRUFWCGBMYDJ-ONEGZZNKSA-N (e)-3-(3,5-dimethoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC(OC)=CC(\C=C\C(O)=O)=C1 VLSRUFWCGBMYDJ-ONEGZZNKSA-N 0.000 claims description 8
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 8
- WMXICQUIACARNL-UHFFFAOYSA-K 4-methylbenzoate terbium(3+) Chemical compound C1(=CC=C(C=C1)C(=O)[O-])C.[Tb+3].C1(=CC=C(C=C1)C(=O)[O-])C.C1(=CC=C(C=C1)C(=O)[O-])C WMXICQUIACARNL-UHFFFAOYSA-K 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims description 7
- NRQHBNNTBIDSRK-YRNVUSSQSA-N (4e)-4-[(4-methoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one Chemical compound C1=CC(OC)=CC=C1\C=C\1C(=O)OC(C)=N/1 NRQHBNNTBIDSRK-YRNVUSSQSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
- 230000021615 conjugation Effects 0.000 claims description 6
- 229940081066 picolinic acid Drugs 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- QGOSWKYGLZGCBH-UHFFFAOYSA-H terbium(3+);terephthalate Chemical compound [Tb+3].[Tb+3].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1.[O-]C(=O)C1=CC=C(C([O-])=O)C=C1.[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 QGOSWKYGLZGCBH-UHFFFAOYSA-H 0.000 claims description 6
- 229910052779 Neodymium Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 5
- UVJXTGHHRXRPRO-UHFFFAOYSA-K europium(3+) 4-methylbenzoate Chemical compound C1(=CC=C(C=C1)C(=O)[O-])C.[Eu+3].C1(=CC=C(C=C1)C(=O)[O-])C.C1(=CC=C(C=C1)C(=O)[O-])C UVJXTGHHRXRPRO-UHFFFAOYSA-K 0.000 claims description 5
- ARGCLRFUGIDKBB-UHFFFAOYSA-K 3-(3,5-dimethoxyphenyl)prop-2-enoate europium(3+) Chemical compound COC=1C=C(C=CC(=O)[O-])C=C(C1)OC.[Eu+3].COC=1C=C(C=CC(=O)[O-])C=C(C1)OC.COC=1C=C(C=CC(=O)[O-])C=C(C1)OC ARGCLRFUGIDKBB-UHFFFAOYSA-K 0.000 claims description 4
- 229910052772 Samarium Inorganic materials 0.000 claims description 4
- 229910052769 Ytterbium Inorganic materials 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- MUTGRVRJCJPFCN-UHFFFAOYSA-H benzene-1,3-dicarboxylate;terbium(3+) Chemical compound [Tb+3].[Tb+3].[O-]C(=O)C1=CC=CC(C([O-])=O)=C1.[O-]C(=O)C1=CC=CC(C([O-])=O)=C1.[O-]C(=O)C1=CC=CC(C([O-])=O)=C1 MUTGRVRJCJPFCN-UHFFFAOYSA-H 0.000 claims description 4
- DSPCOFQXGVSEHZ-UHFFFAOYSA-K europium(3+);thiophene-2-carboxylate Chemical compound [Eu+3].[O-]C(=O)C1=CC=CS1.[O-]C(=O)C1=CC=CS1.[O-]C(=O)C1=CC=CS1 DSPCOFQXGVSEHZ-UHFFFAOYSA-K 0.000 claims description 4
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 4
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 4
- VUVORVXMOLQFMO-UHFFFAOYSA-N 3-pyridin-3-ylprop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CN=C1 VUVORVXMOLQFMO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 3
- 229910052691 Erbium Inorganic materials 0.000 claims description 3
- 229910052689 Holmium Inorganic materials 0.000 claims description 3
- 229910052765 Lutetium Inorganic materials 0.000 claims description 3
- 229910052777 Praseodymium Inorganic materials 0.000 claims description 3
- 229910052775 Thulium Inorganic materials 0.000 claims description 3
- BNZDSZFHGLFGPJ-UHFFFAOYSA-K [Tb+3].[O-]C(=O)c1ccccn1.[O-]C(=O)c1ccccn1.[O-]C(=O)c1ccccn1 Chemical compound [Tb+3].[O-]C(=O)c1ccccn1.[O-]C(=O)c1ccccn1.[O-]C(=O)c1ccccn1 BNZDSZFHGLFGPJ-UHFFFAOYSA-K 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 3
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 claims description 3
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 claims description 3
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims description 3
- KYSJBCJXFZJNJT-UHFFFAOYSA-K C1(=CC(=CC=C1)C(=O)[O-])C.[Eu+3].C1(=CC(=CC=C1)C(=O)[O-])C.C1(=CC(=CC=C1)C(=O)[O-])C Chemical compound C1(=CC(=CC=C1)C(=O)[O-])C.[Eu+3].C1(=CC(=CC=C1)C(=O)[O-])C.C1(=CC(=CC=C1)C(=O)[O-])C KYSJBCJXFZJNJT-UHFFFAOYSA-K 0.000 claims description 2
- QCQSIHJAFDLICZ-UHFFFAOYSA-K C1(=CC(=CC=C1)C(=O)[O-])C.[Tb+3].C1(=CC(=CC=C1)C(=O)[O-])C.C1(=CC(=CC=C1)C(=O)[O-])C Chemical compound C1(=CC(=CC=C1)C(=O)[O-])C.[Tb+3].C1(=CC(=CC=C1)C(=O)[O-])C.C1(=CC(=CC=C1)C(=O)[O-])C QCQSIHJAFDLICZ-UHFFFAOYSA-K 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004151 quinonyl group Chemical group 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 description 148
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 74
- 238000000034 method Methods 0.000 description 62
- 239000000243 solution Substances 0.000 description 56
- 230000000052 comparative effect Effects 0.000 description 48
- 239000000562 conjugate Substances 0.000 description 37
- 239000000203 mixture Substances 0.000 description 35
- 238000002441 X-ray diffraction Methods 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000008213 purified water Substances 0.000 description 30
- NNMXSTWQJRPBJZ-UHFFFAOYSA-K europium(iii) chloride Chemical compound Cl[Eu](Cl)Cl NNMXSTWQJRPBJZ-UHFFFAOYSA-K 0.000 description 27
- 239000000843 powder Substances 0.000 description 27
- 239000007864 aqueous solution Substances 0.000 description 25
- 239000002184 metal Substances 0.000 description 25
- 238000012360 testing method Methods 0.000 description 24
- 239000000463 material Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
- 230000005284 excitation Effects 0.000 description 21
- ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 description 19
- 238000003756 stirring Methods 0.000 description 17
- 150000001735 carboxylic acids Chemical class 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- DXIHILNWDOYYCH-UHDJGPCESA-M sodium;(e)-3-phenylprop-2-enoate Chemical compound [Na+].[O-]C(=O)\C=C\C1=CC=CC=C1 DXIHILNWDOYYCH-UHDJGPCESA-M 0.000 description 14
- 239000006069 physical mixture Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 238000000634 powder X-ray diffraction Methods 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- 238000002329 infrared spectrum Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- GFISHBQNVWAVFU-UHFFFAOYSA-K terbium(iii) chloride Chemical compound Cl[Tb](Cl)Cl GFISHBQNVWAVFU-UHFFFAOYSA-K 0.000 description 7
- 238000010894 electron beam technology Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- OBOSXEWFRARQPU-UHFFFAOYSA-N 2-n,2-n-dimethylpyridine-2,5-diamine Chemical compound CN(C)C1=CC=C(N)C=N1 OBOSXEWFRARQPU-UHFFFAOYSA-N 0.000 description 5
- MEANOSLIBWSCIT-UHFFFAOYSA-K gadolinium trichloride Chemical compound Cl[Gd](Cl)Cl MEANOSLIBWSCIT-UHFFFAOYSA-K 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 5
- 238000006862 quantum yield reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- VUVORVXMOLQFMO-ONEGZZNKSA-N (e)-3-pyridin-3-ylprop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CN=C1 VUVORVXMOLQFMO-ONEGZZNKSA-N 0.000 description 4
- XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 4
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000013522 chelant Substances 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 150000004687 hexahydrates Chemical class 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- GPSDUZXPYCFOSQ-UHFFFAOYSA-M m-toluate Chemical compound CC1=CC=CC(C([O-])=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-M 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 4
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 3
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 3
- RURHILYUWQEGOS-VOTSOKGWSA-N 4-Methylcinnamic acid Chemical compound CC1=CC=C(\C=C\C(O)=O)C=C1 RURHILYUWQEGOS-VOTSOKGWSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000006399 behavior Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000008240 homogeneous mixture Substances 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229940075582 sorbic acid Drugs 0.000 description 3
- 235000010199 sorbic acid Nutrition 0.000 description 3
- 239000004334 sorbic acid Substances 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- YEMUSDCFQUBPAL-SNAWJCMRSA-N (e)-3-(3-bromophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(Br)=C1 YEMUSDCFQUBPAL-SNAWJCMRSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- ZQVKTHRQIXSMGY-UHFFFAOYSA-N 4-Ethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C=C1 ZQVKTHRQIXSMGY-UHFFFAOYSA-N 0.000 description 2
- GXLIFJYFGMHYDY-ZZXKWVIFSA-N 4-chlorocinnamic acid Chemical compound OC(=O)\C=C\C1=CC=C(Cl)C=C1 GXLIFJYFGMHYDY-ZZXKWVIFSA-N 0.000 description 2
- SHSGDXCJYVZFTP-UHFFFAOYSA-N 4-ethoxybenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C=C1 SHSGDXCJYVZFTP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- GNHLCRAUMFTBIE-UHFFFAOYSA-K C(C=CC=CC)(=O)[O-].[Eu+3].C(C=CC=CC)(=O)[O-].C(C=CC=CC)(=O)[O-] Chemical compound C(C=CC=CC)(=O)[O-].[Eu+3].C(C=CC=CC)(=O)[O-].C(C=CC=CC)(=O)[O-] GNHLCRAUMFTBIE-UHFFFAOYSA-K 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001734 carboxylic acid salts Chemical class 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000012769 display material Substances 0.000 description 2
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- 229910052731 fluorine Inorganic materials 0.000 description 2
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- IENZCGNHSIMFJE-UHFFFAOYSA-N indole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC=CC2=C1 IENZCGNHSIMFJE-UHFFFAOYSA-N 0.000 description 1
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- 239000011147 inorganic material Substances 0.000 description 1
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- LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 description 1
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- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
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- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11035779 | 1979-08-31 | ||
| JP11035779A JPS5634782A (en) | 1979-08-31 | 1979-08-31 | Novel energy converting substance and illuminant |
| JP9221480 | 1980-07-08 | ||
| JP9221480A JPS5718779A (en) | 1980-07-08 | 1980-07-08 | Novel luminous substance |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8004876A true NL8004876A (nl) | 1981-03-03 |
Family
ID=26433681
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8004876A NL8004876A (nl) | 1979-08-31 | 1980-08-28 | Organische zeldzame aardmetaalzoutfosfor. |
| NL8301295A NL8301295A (nl) | 1979-08-31 | 1983-04-13 | Organische zeldzame aardmetaalzoutfosfor. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8301295A NL8301295A (nl) | 1979-08-31 | 1983-04-13 | Organische zeldzame aardmetaalzoutfosfor. |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US4443380A (OSRAM) |
| DE (2) | DE3032611C2 (OSRAM) |
| FR (2) | FR2464292A1 (OSRAM) |
| GB (2) | GB2061918B (OSRAM) |
| NL (2) | NL8004876A (OSRAM) |
Families Citing this family (91)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN104193770B (zh) * | 2014-08-01 | 2016-09-28 | 浙江大学 | 一种用于生理温度探测的双稀土有机框架材料及其制备方法 |
| KR101735405B1 (ko) * | 2014-08-22 | 2017-05-15 | 나노씨엠에스(주) | 발광 희토류 화합물 및 이를 포함하는 이색성 형광체 조성물 |
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Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR898263A (fr) * | 1942-09-25 | 1945-04-18 | Auergesellschaft Ag | Agent d'enrobage pour couleurs luminescentes |
| US2901496A (en) * | 1949-09-09 | 1959-08-25 | George A Cowan | Salicylate process for thorium separation from rare earths |
| FR1522465A (fr) * | 1967-03-15 | 1968-04-26 | Centre Nat Rech Scient | Compositions de revêtement invisibles à la lumière ordinaire et visibles dans l'ultra-violet |
| DE1717194A1 (de) * | 1968-01-03 | 1971-07-29 | Georg Dr Kallistratos | Leuchtschirm,insbesondere fuer Elektronenstrahlroehren zur Wiedergabe von Farbbildern |
| GB2061918B (en) * | 1979-08-31 | 1984-05-31 | Asahi Dow Ltd | Organic rare-earth salt phosphors |
| JPS5780476A (en) * | 1980-11-07 | 1982-05-20 | Asahi Chem Ind Co Ltd | Radiation calorescent material |
| JPS5783580A (en) * | 1980-11-12 | 1982-05-25 | Asahi Chem Ind Co Ltd | Temperature-light transducing material |
| JPS57108189A (en) * | 1980-12-25 | 1982-07-06 | Asahi Chem Ind Co Ltd | Temperature-light transducer |
-
1980
- 1980-08-22 GB GB8027344A patent/GB2061918B/en not_active Expired
- 1980-08-22 US US06/180,324 patent/US4443380A/en not_active Expired - Lifetime
- 1980-08-28 NL NL8004876A patent/NL8004876A/nl not_active Application Discontinuation
- 1980-08-28 FR FR8018692A patent/FR2464292A1/fr active Granted
- 1980-08-29 DE DE3032611A patent/DE3032611C2/de not_active Expired
- 1980-08-29 DE DE19803050703 patent/DE3050703C2/de not_active Expired
-
1982
- 1982-05-14 FR FR8208445A patent/FR2509319B1/fr not_active Expired
- 1982-06-30 US US06/393,678 patent/US4572803A/en not_active Expired - Fee Related
-
1983
- 1983-04-13 NL NL8301295A patent/NL8301295A/nl not_active Application Discontinuation
- 1983-04-28 GB GB08311562A patent/GB2128985B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3032611C2 (de) | 1983-12-08 |
| FR2464292B1 (OSRAM) | 1984-04-20 |
| DE3050703C2 (de) | 1983-12-01 |
| FR2464292A1 (fr) | 1981-03-06 |
| DE3032611A1 (de) | 1981-03-26 |
| GB2061918A (en) | 1981-05-20 |
| FR2509319B1 (fr) | 1985-06-07 |
| GB2128985B (en) | 1984-11-14 |
| GB2128985A (en) | 1984-05-10 |
| NL8301295A (nl) | 1983-09-01 |
| GB2061918B (en) | 1984-05-31 |
| GB8311562D0 (en) | 1983-06-02 |
| FR2509319A1 (fr) | 1983-01-14 |
| US4572803A (en) | 1986-02-25 |
| US4443380A (en) | 1984-04-17 |
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