FR2973388A1 - Derives de tetrazine bichromophoriques fluorescents, composition polymere fluorescente les contenant, leur procede de preparation et leurs applications - Google Patents
Derives de tetrazine bichromophoriques fluorescents, composition polymere fluorescente les contenant, leur procede de preparation et leurs applications Download PDFInfo
- Publication number
- FR2973388A1 FR2973388A1 FR1154792A FR1154792A FR2973388A1 FR 2973388 A1 FR2973388 A1 FR 2973388A1 FR 1154792 A FR1154792 A FR 1154792A FR 1154792 A FR1154792 A FR 1154792A FR 2973388 A1 FR2973388 A1 FR 2973388A1
- Authority
- FR
- France
- Prior art keywords
- fluorescent
- bichromophoric
- polymer
- formula
- composition
- 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
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- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 150000004905 tetrazines Chemical class 0.000 title claims abstract description 19
- 229920001109 fluorescent polymer Polymers 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229920000642 polymer Polymers 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000000835 fiber Substances 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 41
- 239000002904 solvent Substances 0.000 claims description 17
- 229920000515 polycarbonate Polymers 0.000 claims description 15
- 239000004417 polycarbonate Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- -1 polyethylene Polymers 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 4
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 4
- MZCNCJNOOWONIO-UHFFFAOYSA-N 5-chlorotetrazine Chemical compound ClC1=CN=NN=N1 MZCNCJNOOWONIO-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 238000007493 shaping process Methods 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229920003235 aromatic polyamide Polymers 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 2
- 229920000193 polymethacrylate Polymers 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 230000002745 absorbent Effects 0.000 claims 1
- 239000002250 absorbent Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000011550 stock solution Substances 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229920006254 polymer film Polymers 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 4
- YJDGCKQTFGITHQ-UHFFFAOYSA-N 2-[2-(trifluoromethyl)benzimidazol-1-yl]ethanol Chemical compound C1=CC=C2N(CCO)C(C(F)(F)F)=NC2=C1 YJDGCKQTFGITHQ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- PJBDTFYJRYBUKR-UHFFFAOYSA-N 5,6-dichlorotetrazine Chemical compound ClC1=NN=NN=C1Cl PJBDTFYJRYBUKR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000005893 naphthalimidyl group Chemical group 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DKLWRIQKXIBVIS-UHFFFAOYSA-N 1,1-diiodooctane Chemical compound CCCCCCCC(I)I DKLWRIQKXIBVIS-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- MXFMPTXDHSDMTI-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=CC=C2NC(C(F)(F)F)=NC2=C1 MXFMPTXDHSDMTI-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 229940075397 calomel Drugs 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
- 238000003475 lamination Methods 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 238000010147 laser engraving Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 125000005545 phthalimidyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B42—BOOKBINDING; ALBUMS; FILES; SPECIAL PRINTED MATTER
- B42D—BOOKS; BOOK COVERS; LOOSE LEAVES; PRINTED MATTER CHARACTERISED BY IDENTIFICATION OR SECURITY FEATURES; PRINTED MATTER OF SPECIAL FORMAT OR STYLE NOT OTHERWISE PROVIDED FOR; DEVICES FOR USE THEREWITH AND NOT OTHERWISE PROVIDED FOR; MOVABLE-STRIP WRITING OR READING APPARATUS
- B42D25/00—Information-bearing cards or sheet-like structures characterised by identification or security features; Manufacture thereof
- B42D25/30—Identification or security features, e.g. for preventing forgery
- B42D25/36—Identification or security features, e.g. for preventing forgery comprising special materials
- B42D25/378—Special inks
- B42D25/387—Special inks absorbing or reflecting ultraviolet light
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B42—BOOKBINDING; ALBUMS; FILES; SPECIAL PRINTED MATTER
- B42D—BOOKS; BOOK COVERS; LOOSE LEAVES; PRINTED MATTER CHARACTERISED BY IDENTIFICATION OR SECURITY FEATURES; PRINTED MATTER OF SPECIAL FORMAT OR STYLE NOT OTHERWISE PROVIDED FOR; DEVICES FOR USE THEREWITH AND NOT OTHERWISE PROVIDED FOR; MOVABLE-STRIP WRITING OR READING APPARATUS
- B42D25/00—Information-bearing cards or sheet-like structures characterised by identification or security features; Manufacture thereof
- B42D25/20—Information-bearing cards or sheet-like structures characterised by identification or security features; Manufacture thereof characterised by a particular use or purpose
- B42D25/23—Identity cards
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
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- 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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
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- 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
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- B42D2033/04—
-
- B42D2033/30—
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B42—BOOKBINDING; ALBUMS; FILES; SPECIAL PRINTED MATTER
- B42D—BOOKS; BOOK COVERS; LOOSE LEAVES; PRINTED MATTER CHARACTERISED BY IDENTIFICATION OR SECURITY FEATURES; PRINTED MATTER OF SPECIAL FORMAT OR STYLE NOT OTHERWISE PROVIDED FOR; DEVICES FOR USE THEREWITH AND NOT OTHERWISE PROVIDED FOR; MOVABLE-STRIP WRITING OR READING APPARATUS
- B42D25/00—Information-bearing cards or sheet-like structures characterised by identification or security features; Manufacture thereof
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- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
Abstract
Description
Claims (12)
- REVENDICATIONS1. Dérivé de tétrazine bichromophorique fluorescent de formule (1) ci-dessous: N -N Y (1) N ===N dans laquelle: - X représente un atome d'oxygène ou de soufre; - n est un nombre entier compris entre 0 et 5, de préférence entre 0 et 3, plus préférentiellement encore égal à 2; - Y est un groupe électroattracteur choisi dans le groupe comprenant les halogènes, les groupes neutres constitués à partir d'un hétéroatome bi- ou trivalent comme l'oxygène, notamment -O-A-R où A représente une liaison simple ou un alkylidènyle en C1-C4 et R est alkyle, alcényle, alcynyle, cycloalkyle, aryle, époxyalkyle, mono-, di- ou trifluoroalkyle ou perfluoroalkyle, et les électroattracteurs ioniques de type « onium » notamment pyridinium, imidazolium, phosphonium et composés analogues; - Z est un absorbant UV électrodéficitaire choisi dans le groupe comprenant les groupes suivants:
- 2. Dérivé de tétrazine bichromophorique fluorescent selon la revendication 1, caractérisé par le fait qu'il présente l'une des formules suivantes: O N=N N~O \ >Cl N-N , OU
- 3. Procédé de préparation d'un dérivé de tetrazine bichromophorique fluorescent de formule (1) tel que défini à la revendication 1 ou 2 comprenant le couplage d' une chlorotétrazine de formule (2) avec un alcool ou un thiol de formule (3): Cl N-N NN Y (2) z X H (3) dans lesquelles X, n, Y et Z sont tels que définis à la revendication 1.
- 4. Composition polymère comprenant un polymère et un dérivé de tétrazine bichromophorique fluorescent de formule (1) tel que 20 défini à la revendication 1 ou 2.
- 5. Composition selon la revendication 4, caractérisée par le fait qu'elle comprend un solvant.
- 6. Composition selon la revendication 4 ou 5, caractérisée par le fait que le polymère est choisi dans le groupe comprenant un polycarbonate, un polystyrène, un polyéthylène, un polyéthylène téréphtalate, un polyacrylate, un polyméthacrylate, un poly(chlorure de vinyle), un polyamide, un polyaramide, et leurs mélanges.
- 7. Composition selon l'une quelconque des revendications 5 et 6, caractérisée par le fait que le solvant est un solvant non nucléophile, choisi dans le groupe comprenant les cétones, les sulfoxydes, les nitriles, les esters, les hétérocycles azotés, les éthers, les solvants chlorés, et leurs mélanges.
- 8. Composition selon l'une quelconque des revendications 4 à 7, caractérisée par le fait qu'elle comprend un polycarbonate, un dérivé de tétrazine bichromophorique fluorescent de formule >cl ou de formule >cIet du dichlorométhane.
- 9. Film, fil ou fibre polymère fluorescent, caractérisé par le fait qu'il comprend un dérivé de tétrazine bichromophorique de formule (1) tel que défini à l'une la revendication 1 ou 2 ou une composition telle que définie à l'une quelconque des revendications 4 à 8.
- 10. Procédé de sécurisation de documents comprenant la 10 formation d'un film, un fil ou de fibre polymère fluorescent tel que défini à la revendication 9.
- 11. Utilisation d'un dérivé de tétrazine bichromophorique selon la revendication 1 ou 2, une composition selon l'une 15 quelconque des revendications 4 à 8, ou d'un film, un fil ou de fibre polymère selon la revendication 9, pour le marquage de produits polymères, la sécurisation de documents, notamment de cartes, badges, etc., et pour la réalisation d'élément de décoration. 20
- 12. Procédé de traçage de matériau polymère comprenant la préparation d'une composition polymère telle que définie à l'une quelconque des revendications 4 à 8, puis la mise en forme de cette composition polymère, de préférence sous forme 25 de film, de fil ou de fibre. 22
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1154792A FR2973388B1 (fr) | 2011-03-31 | 2011-05-31 | Derives de tetrazine bichromophoriques fluorescents, composition polymere fluorescente les contenant, leur procede de preparation et leurs applications |
PCT/FR2012/050703 WO2012131278A1 (fr) | 2011-03-31 | 2012-03-30 | Composition polymere fluorescente, derives de tetrazine bichromophoriques fluorescents, leur procede de preparation et leurs applications |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1152751A FR2973392A1 (fr) | 2011-03-31 | 2011-03-31 | Composition polymere fluorescente, films comprenant ladite composition, leur procede de preparation et leurs applications |
FR1154792A FR2973388B1 (fr) | 2011-03-31 | 2011-05-31 | Derives de tetrazine bichromophoriques fluorescents, composition polymere fluorescente les contenant, leur procede de preparation et leurs applications |
Publications (2)
Publication Number | Publication Date |
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FR2973388A1 true FR2973388A1 (fr) | 2012-10-05 |
FR2973388B1 FR2973388B1 (fr) | 2015-01-16 |
Family
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Family Applications (2)
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FR1152751A Withdrawn FR2973392A1 (fr) | 2011-03-31 | 2011-03-31 | Composition polymere fluorescente, films comprenant ladite composition, leur procede de preparation et leurs applications |
FR1154792A Active FR2973388B1 (fr) | 2011-03-31 | 2011-05-31 | Derives de tetrazine bichromophoriques fluorescents, composition polymere fluorescente les contenant, leur procede de preparation et leurs applications |
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FR1152751A Withdrawn FR2973392A1 (fr) | 2011-03-31 | 2011-03-31 | Composition polymere fluorescente, films comprenant ladite composition, leur procede de preparation et leurs applications |
Country Status (2)
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FR (2) | FR2973392A1 (fr) |
WO (1) | WO2012131278A1 (fr) |
Families Citing this family (4)
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FR3038322B1 (fr) | 2015-07-01 | 2018-10-19 | Universite De Montpellier (Universite Montpellier 2 Sciences Et Techniques) | Materiaux reticules thermodurcissables a basse tg et thermostables a base d'unites fluoroethers |
CN111333641B (zh) * | 2018-12-18 | 2022-05-31 | 中国科学院大连化学物理研究所 | 一种用于四嗪类生物正交标记的增强型荧光探针及其合成 |
WO2022077052A1 (fr) * | 2020-10-12 | 2022-04-21 | The University Of Sydney | Composés sondes pour imagerie de membrane mitochondriale |
CN114671851B (zh) * | 2020-12-24 | 2024-03-26 | 中国医学科学院药物研究所 | 萘二甲酰亚胺-四嗪类化合物及其制备方法与应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4756557A (en) * | 1984-12-21 | 1988-07-12 | G.A.O. Gesellschaft Fuer Automation Und Organisation Mbh | Security document having a security thread embedded therein and methods for producing and testing the authenticity of the security document |
WO2002046528A1 (fr) * | 2000-12-05 | 2002-06-13 | Spectra Systems Corporation | Revetement fluorescent pigmente a microparticules fluorescentes integrees pour la securite de document optique |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5658494A (en) * | 1992-02-14 | 1997-08-19 | Amersham International Plc | Fluorescent compounds |
AT403967B (de) * | 1992-11-18 | 1998-07-27 | Oesterr Nationalbank | Dokument und folienaufbau zur herstellung eines dokumentes |
-
2011
- 2011-03-31 FR FR1152751A patent/FR2973392A1/fr not_active Withdrawn
- 2011-05-31 FR FR1154792A patent/FR2973388B1/fr active Active
-
2012
- 2012-03-30 WO PCT/FR2012/050703 patent/WO2012131278A1/fr active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4756557A (en) * | 1984-12-21 | 1988-07-12 | G.A.O. Gesellschaft Fuer Automation Und Organisation Mbh | Security document having a security thread embedded therein and methods for producing and testing the authenticity of the security document |
WO2002046528A1 (fr) * | 2000-12-05 | 2002-06-13 | Spectra Systems Corporation | Revetement fluorescent pigmente a microparticules fluorescentes integrees pour la securite de document optique |
Non-Patent Citations (4)
Title |
---|
E. CUELLAR, G. CASTRO: "Photochemical and nonphotochemical hole burning in dimethyl-s-tetrazine in a polyvinyl carbazole film", CHEMICAL PHYSICS, vol. 54, 1981, pages 217 - 225, XP002657293 * |
G. CLAVIER, P. AUDEBERT: "s-Tetrazines as building blocks for new functional molecules and molecular materials", CHEM. REV., vol. 110, 22 March 2010 (2010-03-22), pages 3299 - 3314, XP002657292 * |
YUNA KIM ET.AL.: "New tetrazine-based fluororelectrochromic window; modulation of the fluorescence through applied potential", CHEM. COMMUN., 2006, pages 3612 - 3614, XP002657294 * |
YUNA KIM ET.AL.: "Tetrazine-based electrofluorochromic windows: modulation of the fluorescence through applied potential", JOURNAL OF ELECTROANALYTICAL CHEMISTRY, vol. 632, 2009, pages 201 - 205, XP002657295 * |
Also Published As
Publication number | Publication date |
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FR2973388B1 (fr) | 2015-01-16 |
WO2012131278A1 (fr) | 2012-10-04 |
FR2973392A1 (fr) | 2012-10-05 |
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