FR2464292A1 - Luminophore a base de sel organique de metal de terre rare - Google Patents
Luminophore a base de sel organique de metal de terre rare Download PDFInfo
- Publication number
- FR2464292A1 FR2464292A1 FR8018692A FR8018692A FR2464292A1 FR 2464292 A1 FR2464292 A1 FR 2464292A1 FR 8018692 A FR8018692 A FR 8018692A FR 8018692 A FR8018692 A FR 8018692A FR 2464292 A1 FR2464292 A1 FR 2464292A1
- Authority
- FR
- France
- Prior art keywords
- acid
- salt
- europium
- terbium
- carboxylic acid
- 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.)
- Granted
Links
- 229910052761 rare earth metal Inorganic materials 0.000 title claims abstract description 69
- 150000002910 rare earth metals Chemical class 0.000 title claims abstract description 40
- 150000003839 salts Chemical class 0.000 title claims description 201
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 30
- 229910052712 strontium Inorganic materials 0.000 claims abstract description 19
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims abstract description 19
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052788 barium Inorganic materials 0.000 claims abstract description 17
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 17
- 239000011575 calcium Substances 0.000 claims abstract description 17
- 229910052693 Europium Inorganic materials 0.000 claims description 100
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 99
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 85
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 57
- 229940114081 cinnamate Drugs 0.000 claims description 50
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 42
- 235000013985 cinnamic acid Nutrition 0.000 claims description 39
- 229910052771 Terbium Inorganic materials 0.000 claims description 38
- 229930016911 cinnamic acid Natural products 0.000 claims description 38
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 37
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 37
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 35
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 35
- -1 rare earth metal salt Chemical class 0.000 claims description 34
- 229910052751 metal Inorganic materials 0.000 claims description 33
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 32
- 229910052746 lanthanum Inorganic materials 0.000 claims description 26
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 26
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 claims description 24
- 239000002184 metal Substances 0.000 claims description 24
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 23
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 22
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 22
- 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
- 150000007524 organic acids Chemical class 0.000 claims description 14
- 125000000962 organic group Chemical group 0.000 claims description 12
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 11
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 10
- GPSDUZXPYCFOSQ-UHFFFAOYSA-M m-toluate Chemical compound CC1=CC=CC(C([O-])=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-M 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 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 6
- 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 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052779 Neodymium Inorganic materials 0.000 claims description 5
- 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 5
- 229940081066 picolinic acid Drugs 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052692 Dysprosium 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
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 4
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Chemical group 0.000 claims description 4
- 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 3
- 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 3
- 229910052684 Cerium 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
- 229910052772 Samarium 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 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
- 229910052799 carbon Inorganic materials 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
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 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 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- BFHKYHMIVDBCPC-UHFFFAOYSA-N 1,3,5,7-tetrahydro-[1,3]oxazolo[3,4-c][1,3]oxazol-7a-ylmethanol Chemical compound C1OCN2COCC21CO BFHKYHMIVDBCPC-UHFFFAOYSA-N 0.000 claims 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-M p-toluate Chemical compound CC1=CC=C(C([O-])=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-M 0.000 claims 1
- 125000004151 quinonyl group Chemical group 0.000 claims 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 15
- 230000005693 optoelectronics Effects 0.000 abstract description 3
- 230000000295 complement effect Effects 0.000 abstract 1
- 238000004020 luminiscence type Methods 0.000 description 140
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
- 238000000034 method Methods 0.000 description 66
- 238000012360 testing method Methods 0.000 description 64
- 239000007864 aqueous solution Substances 0.000 description 56
- 230000000052 comparative effect Effects 0.000 description 46
- 239000000203 mixture Substances 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 238000000634 powder X-ray diffraction Methods 0.000 description 32
- 230000021615 conjugation Effects 0.000 description 30
- NNMXSTWQJRPBJZ-UHFFFAOYSA-K europium(iii) chloride Chemical compound Cl[Eu](Cl)Cl NNMXSTWQJRPBJZ-UHFFFAOYSA-K 0.000 description 30
- 239000008213 purified water Substances 0.000 description 30
- 230000008569 process Effects 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 23
- 230000005284 excitation Effects 0.000 description 19
- 239000000843 powder Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 18
- ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 description 17
- 238000000113 differential scanning calorimetry Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 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
- 239000000463 material Substances 0.000 description 13
- 239000006069 physical mixture Substances 0.000 description 11
- 239000000470 constituent Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 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 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 230000006870 function Effects 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000919 ceramic Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- 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 description 5
- GFISHBQNVWAVFU-UHFFFAOYSA-K terbium(iii) chloride Chemical compound Cl[Tb](Cl)Cl GFISHBQNVWAVFU-UHFFFAOYSA-K 0.000 description 5
- SHSGDXCJYVZFTP-UHFFFAOYSA-N 4-ethoxybenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C=C1 SHSGDXCJYVZFTP-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 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 description 4
- MEANOSLIBWSCIT-UHFFFAOYSA-K gadolinium trichloride Chemical compound Cl[Gd](Cl)Cl MEANOSLIBWSCIT-UHFFFAOYSA-K 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 230000005855 radiation Effects 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
- ZQVKTHRQIXSMGY-UHFFFAOYSA-N 4-Ethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C=C1 ZQVKTHRQIXSMGY-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229910052783 alkali metal Inorganic materials 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
- 238000007707 calorimetry Methods 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 3
- HQWUQSSKOBTIHZ-UHFFFAOYSA-N gadolinium terbium Chemical compound [Gd][Tb] HQWUQSSKOBTIHZ-UHFFFAOYSA-N 0.000 description 3
- 150000004687 hexahydrates Chemical class 0.000 description 3
- 239000008240 homogeneous mixture Substances 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- CKMXAIVXVKGGFM-UHFFFAOYSA-N p-cumic acid Chemical compound CC(C)C1=CC=C(C(O)=O)C=C1 CKMXAIVXVKGGFM-UHFFFAOYSA-N 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000006862 quantum yield reaction Methods 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 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
- 238000006467 substitution reaction Methods 0.000 description 3
- QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-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
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- JLWMMYZWEHHTFF-UHFFFAOYSA-N 2-[6-(3-carbamimidoylphenoxy)-4-[di(propan-2-yl)amino]-3,5-difluoropyridin-2-yl]oxy-5-(2-methylpropylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC(C(=O)NCC(C)C)=CC=C1OC1=NC(OC=2C=C(C=CC=2)C(N)=N)=C(F)C(N(C(C)C)C(C)C)=C1F JLWMMYZWEHHTFF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VLSRUFWCGBMYDJ-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC(OC)=CC(C=CC(O)=O)=C1 VLSRUFWCGBMYDJ-UHFFFAOYSA-N 0.000 description 2
- XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 2
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 2
- RURHILYUWQEGOS-VOTSOKGWSA-N 4-Methylcinnamic acid Chemical compound CC1=CC=C(\C=C\C(O)=O)C=C1 RURHILYUWQEGOS-VOTSOKGWSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- VVNLENFYCXOLPC-UHFFFAOYSA-N pyridin-3-yl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CN=C1 VVNLENFYCXOLPC-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 238000005395 radioluminescence Methods 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- GNCGTEQGBYYYBX-UHFFFAOYSA-M sodium;4-methylbenzoate Chemical compound [Na+].CC1=CC=C(C([O-])=O)C=C1 GNCGTEQGBYYYBX-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- TXBBUSUXYMIVOS-UHFFFAOYSA-N thenoyltrifluoroacetone Chemical compound FC(F)(F)C(=O)CC(=O)C1=CC=CS1 TXBBUSUXYMIVOS-UHFFFAOYSA-N 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N urocanic acid Chemical compound OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229910052844 willemite Inorganic materials 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-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
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11035779A JPS5634782A (en) | 1979-08-31 | 1979-08-31 | Novel energy converting substance and illuminant |
| JP9221480A JPS5718779A (en) | 1980-07-08 | 1980-07-08 | Novel luminous substance |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2464292A1 true FR2464292A1 (fr) | 1981-03-06 |
| FR2464292B1 FR2464292B1 (enExample) | 1984-04-20 |
Family
ID=26433681
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8018692A Granted FR2464292A1 (fr) | 1979-08-31 | 1980-08-28 | Luminophore a base de sel organique de metal de terre rare |
| FR8208445A Expired FR2509319B1 (fr) | 1979-08-31 | 1982-05-14 | Luminophore a base de sel organique d'europium |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8208445A Expired FR2509319B1 (fr) | 1979-08-31 | 1982-05-14 | Luminophore a base de sel organique d'europium |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US4443380A (enExample) |
| DE (2) | DE3032611C2 (enExample) |
| FR (2) | FR2464292A1 (enExample) |
| GB (2) | GB2061918B (enExample) |
| NL (2) | NL8004876A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0333162A3 (en) * | 1988-03-16 | 1991-01-23 | Mitsubishi Rayon Co., Ltd. | Phosphor paste compositions and phosphor coatings obtained therefrom |
| EP0700980A4 (en) * | 1994-03-17 | 1996-12-18 | Hitachi Maxell | LUMINOPHORE, LUMINOPHORE COMPOSITION, FLUORESCENT BRAND CARRIER AND OPTICAL CHARACTER |
Families Citing this family (89)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2061918B (en) * | 1979-08-31 | 1984-05-31 | Asahi Dow Ltd | Organic rare-earth salt phosphors |
| US4957939A (en) * | 1981-07-24 | 1990-09-18 | Schering Aktiengesellschaft | Sterile pharmaceutical compositions of gadolinium chelates useful enhancing NMR imaging |
| DE3525994A1 (de) * | 1985-07-20 | 1987-01-29 | Philips Patentverwaltung | Elektronenstrahl-aufzeichnungstraeger |
| US4752424A (en) * | 1986-01-30 | 1988-06-21 | Kabushiki Kaisha Toshiba | Method of manufacturing a rare earth oxysulfide ceramic |
| GB8602304D0 (en) * | 1986-01-30 | 1986-03-05 | Dakubu S | Dihydropyridine condensation products |
| US5154764A (en) * | 1990-04-10 | 1992-10-13 | Mooney Chemicals, Inc. | Neodymium carboxylates as driers in high-solids coating compositions |
| US5095099A (en) * | 1990-12-10 | 1992-03-10 | E. I. Du Pont De Nemours And Company | Fluorescent compounds for absorption and re-emission of radiation |
| US5415151A (en) * | 1993-09-20 | 1995-05-16 | Jcf Research Associates, Inc. | Phosphor-containing projectile and launcher therefor |
| US5693693A (en) * | 1994-12-01 | 1997-12-02 | Pitney Bowes, Inc. | Bar code printing and scanning using wax based invisible fluorescent inks |
| US5502304A (en) * | 1994-12-01 | 1996-03-26 | Pitney Bowes Inc. | Bar code scanner for reading a visible ink and a luminescent invisible ink |
| US5525798A (en) * | 1994-12-01 | 1996-06-11 | Pitney Bowes Inc. | Bar code scanner for reading a lower layer luminescent invisible ink that is printed below a upper layer luminescent invisible ink |
| US5542971A (en) * | 1994-12-01 | 1996-08-06 | Pitney Bowes | Bar codes using luminescent invisible inks |
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| US5876960A (en) * | 1997-08-11 | 1999-03-02 | The United States Of America As Represented By The Secretary Of The Army | Bacterial spore detection and quantification methods |
| CA2393794A1 (en) * | 1999-12-07 | 2001-06-14 | Robert H. Miller | Long persistent phosphor incorporated within a fabric material |
| FR2814737B1 (fr) * | 2000-10-03 | 2003-08-29 | Rhodia Terres Rares | Compose anhydre a base d'un halogenure de terre rare ou de gallium, son procede de preparation et son utilisation comme catalyseur |
| GB0109758D0 (en) * | 2001-04-20 | 2001-06-13 | Elam T Ltd | Mixed metal organic complexes |
| DE20119574U1 (de) * | 2001-12-03 | 2002-10-02 | Kynast, Ulrich, Prof. Dr., 48565 Steinfurt | Darstellung von Polyurethanen mit Komplexen der Seltenen Erden zur Erzeugung von Lumineszenzeffekten |
| DE10163295B4 (de) | 2001-12-21 | 2004-03-25 | Honeywell Specialty Chemicals Seelze Gmbh | Seltenerdmetall-Verbindungen und Gemische von diesen, Verfahren zu deren Herstellung sowie deren Verwendung |
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| CN101067079B (zh) * | 2007-05-25 | 2010-05-19 | 上海师范大学 | 核-壳结构杂化纳米荧光粉体及其制备方法 |
| FR2917226B1 (fr) * | 2007-06-06 | 2009-09-11 | Inst Nat Sciences Appliq | Procede de marquage de materiaux a base de matrices organiques polymeriques thermoplastiques ou thermodurcissables |
| RU2373211C2 (ru) * | 2007-10-05 | 2009-11-20 | Самсунг Электроникс Ко., Лтд | Соединение ди(нитрато)ацетилацетонатобис (1,10-фенантролин) лантаноид (iii), пригодное для использования в качестве люминесцентной добавки в чернила, и чернила для скрытой маркировки ценных материальных объектов |
| DE102008058177A1 (de) * | 2008-11-20 | 2010-06-24 | Eos Gmbh Electro Optical Systems | Verfahren zur Identifizierung von Lasersinterpulvern |
| US7762329B1 (en) | 2009-01-27 | 2010-07-27 | Halliburton Energy Services, Inc. | Methods for servicing well bores with hardenable resin compositions |
| CN102766356B (zh) * | 2012-07-31 | 2013-12-04 | 武汉大学 | 一种紫外线复合吸收材料及其制备方法 |
| EP3090032A1 (en) * | 2013-12-04 | 2016-11-09 | Merck Patent GmbH | Eu2 -activated phosphors |
| 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 |
| RU2643966C1 (ru) * | 2017-05-29 | 2018-02-06 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Кубанский государственный университет" (ФГБОУ ВО "КубГУ") | Способ получения ацетилсалицилата тербия(iii) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR898263A (fr) * | 1942-09-25 | 1945-04-18 | Auergesellschaft Ag | Agent d'enrobage pour couleurs luminescentes |
| DE1717194A1 (de) * | 1968-01-03 | 1971-07-29 | Georg Dr Kallistratos | Leuchtschirm,insbesondere fuer Elektronenstrahlroehren zur Wiedergabe von Farbbildern |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR898263A (fr) * | 1942-09-25 | 1945-04-18 | Auergesellschaft Ag | Agent d'enrobage pour couleurs luminescentes |
| DE1717194A1 (de) * | 1968-01-03 | 1971-07-29 | Georg Dr Kallistratos | Leuchtschirm,insbesondere fuer Elektronenstrahlroehren zur Wiedergabe von Farbbildern |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/72 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0333162A3 (en) * | 1988-03-16 | 1991-01-23 | Mitsubishi Rayon Co., Ltd. | Phosphor paste compositions and phosphor coatings obtained therefrom |
| US5277840A (en) * | 1988-03-16 | 1994-01-11 | Mitsubishi Rayon Co., Ltd. | Phosphor paste compositions and phosphor coatings obtained therefrom |
| EP0700980A4 (en) * | 1994-03-17 | 1996-12-18 | Hitachi Maxell | LUMINOPHORE, LUMINOPHORE COMPOSITION, FLUORESCENT BRAND CARRIER AND OPTICAL CHARACTER |
| US5932139A (en) * | 1994-03-17 | 1999-08-03 | Hitachi Maxell, Ltd. | Fluorescent substance, fluorescent composition, fluorescent mark carrier and optical reader thereof |
| US6303929B1 (en) | 1994-03-17 | 2001-10-16 | Hitachi Maxell, Ltd. | Fluorescent substance, fluorescent composition, fluorescent mark carrier and optical reader therefor |
| US6436314B1 (en) | 1994-03-17 | 2002-08-20 | Hitachi Maxell, Ltd. | Particulate fluorescent substance |
| US6458294B2 (en) | 1994-03-17 | 2002-10-01 | Hitachi Maxell, Ltd. | Fluorescent ink compositions |
| US6471887B2 (en) | 1994-03-17 | 2002-10-29 | Hitachi Maxell, Ltd. | Neodymium, ytterbium and/or erbium containing organic fluorescent compositions |
| US6688789B2 (en) | 1994-03-17 | 2004-02-10 | Hitachi Maxell, Ltd. | Fluorescent substance, fluorescent composition, fluorescent mark carrier and optical reader therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| NL8004876A (nl) | 1981-03-03 |
| DE3032611C2 (de) | 1983-12-08 |
| FR2464292B1 (enExample) | 1984-04-20 |
| DE3050703C2 (de) | 1983-12-01 |
| 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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