US 12,180,378 B2Granted

Colorimetric sensor formulation and use thereof

OwnerRachel Evans, Steve Combyinventors

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Abstract

The invention relates to a luminescence-based colorimetric sensor formulation and method of use thereof. The sensor formulation can be used to assess oxygen concentration, particularly in controlled oxygen atmospheres such as food packaging. In embodiments, the invention also relates to sensor-containing laminate films for food packaging, and methods of their preparation.

Claims13

Dependent claims

A colorimetric oxygen sensor formulation comprising a first lumophore and a second lumophore directly dispersed in a polymer matrix, wherein:

(i) the first lumophore is platinum 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin (PtTFPP) and the second lumophore is 2,3,6,7-tetrahydro-9-trifluoromethyl-1H,5H-quinolizino(9,1-gh) coumarin (C153);
(ii) the first lumophore is platinum octaethylporphyrin (PtOEP) and the second lumophore is 2,3,6,7-tetrahydro-9-trifluoromethyl-1H,5H-quinolizino(9,1-gh) coumarin (C153);
iii) the first lumophore is platinum octaethylporphyrin (PtOEP) and the second lumophore is 7-benzylamino-4-nitrobenz-2-oxa-1,3-diazole (BBD);
(iv) the first lumophore is platinum octaethylporphyrin (PtOEP) and the second lumophore is rhodamine 6G (R6G);
(v) the first lumophore is ruthenium (II) 4,7-diphenyl-1, 10′-phenanthroline [Ru(dpp)3]2+ and the second lumophore is 3-(2-benzothiazolyl)-7-(diethylamino) coumarin (C6);
(vi) the first lumophore is ruthenium (II) 4,7-diphenyl-1, 10′-phenanthroline [Ru(dpp)3]2+ and the second lumophore is 2,3,6,7-tetrahydro-9-trifluoromethyl-1H,5H-quinolizino(9,1-gh) coumarin (C153);
(vii) the first lumophore is ruthenium (II) 4,7-diphenyl-1, 10′-phenanthroline [Ru(dpp)3]2+ and the second lumophore is rhodamine 6G (R6G);
(viii) the first lumophore is platinum meso-tetraphenylporphyrin (PtTPP) and the second lumophore is 3-(2-benzothiazolyl)-7-(diethylamino) coumarin (C6);
(ix) the first lumophore is platinum meso-tetraphenylporphyrin (PtTPP) and the second lumophore is 2,3,6,7-tetrahydro-9-trifluoromethyl-1H,5H-quinolizino(9,1-gh) coumarin (C153);
(x) the first lumophore is platinum meso-tetraphenylporphyrin (PtTPP) and the second lumophore is 7-benzylamino-4-nitrobenz-2-oxa-1,3-diazole (BBD);
(xi) the first lumophore is platinum meso-tetraphenylporphyrin (PtTPP) and the second lumophore is rhodamine 6G (R6G);
(xii) the first lumophore is palladium 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin (PdTFPP) and the second lumophore is 3-(2-benzothiazolyl)-7-(diethylamino) coumarin (C6);
(xiii) the first lumophore is palladium 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin (PdTFPP) and the second lumophore is 2,3,6,7-tetrahydro-9-trifluoromethyl-1H,5H-quinolizino(9,1-gh) coumarin (C153);
(xiv) the first lumophore is 4,7-diphenyl-1,10′-phenanthroline ([Ru(dpp)3]2+) and the second lumophore is 7-benzylamino-4-nitrobenz-2-oxa-1,3-diazole (BBD);
(xv) the first lumophore is platinum 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin (PtTFPP) and the second lumophore is 7-benzylamino-4-nitrobenz-2-oxa-1,3-diazole (BBD);
or
(xvi) the first lumophore is palladium 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin (PdTFPP) and the second lumophore is 7-benzylamino-4-nitrobenz-2-oxa-1,3-diazole (BBD).

14 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/271,218Filed 31 Aug 2019
Priority: EP 181923293 Sep 2018
Published: US 2021/0246326 A112 Aug 2021
Granted: 31 Dec 2024
Term ends: Not estimatedThe source records don’t support an estimate.

Classification12 codes

C09D 11/50
Inks: sympathetic, colour changing or similar inks
C09K 11/06
Luminescent materials, e.g. electroluminescent or chemiluminescent: containing organic luminescent materials
C09K 11/07
Containing organic luminescent materials: having chemically-interreactive components, e.g. reactive chemiluminescent compositions
G01N 21/29
Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands: using…

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US 2021/0246326 A1Pre-grant publication · published 12 Aug 2021
US 12,180,378 B2This patent

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Abstract

A colorimetric oxygen sensor formulation comprising a first lumophore and a second lumophore directly dispersed in a polymer matrix, wherein:

(i) the first lumophore is platinum 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin (PtTFPP) and the second lumophore is 2,3,6,7-tetrahydro-9-trifluoromethyl-1H,5H-quinolizino(9,1-gh) coumarin (C153);
(ii) the first lumophore is platinum octaethylporphyrin (PtOEP) and the second lumophore is 2,3,6,7-tetrahydro-9-trifluoromethyl-1H,5H-quinolizino(9,1-gh) coumarin (C153);
iii) the first lumophore is platinum octaethylporphyrin (PtOEP) and the second lumophore is 7-benzylamino-4-nitrobenz-2-oxa-1,3-diazole (BBD);
(iv) the first lumophore is platinum octaethylporphyrin (PtOEP) and the second lumophore is rhodamine 6G (R6G);
(v) the first lumophore is ruthenium (II) 4,7-diphenyl-1, 10′-phenanthroline [Ru(dpp)3]2+ and the second lumophore is 3-(2-benzothiazolyl)-7-(diethylamino) coumarin (C6);
(vi) the first lumophore is ruthenium (II) 4,7-diphenyl-1, 10′-phenanthroline [Ru(dpp)3]2+ and the second lumophore is 2,3,6,7-tetrahydro-9-trifluoromethyl-1H,5H-quinolizino(9,1-gh) coumarin (C153);
(vii) the first lumophore is ruthenium (II) 4,7-diphenyl-1, 10′-phenanthroline [Ru(dpp)3]2+ and the second lumophore is rhodamine 6G (R6G);
(viii) the first lumophore is platinum meso-tetraphenylporphyrin (PtTPP) and the second lumophore is 3-(2-benzothiazolyl)-7-(diethylamino) coumarin (C6);
(ix) the first lumophore is platinum meso-tetraphenylporphyrin (PtTPP) and the second lumophore is 2,3,6,7-tetrahydro-9-trifluoromethyl-1H,5H-quinolizino(9,1-gh) coumarin (C153);
(x) the first lumophore is platinum meso-tetraphenylporphyrin (PtTPP) and the second lumophore is 7-benzylamino-4-nitrobenz-2-oxa-1,3-diazole (BBD);
(xi) the first lumophore is platinum meso-tetraphenylporphyrin (PtTPP) and the second lumophore is rhodamine 6G (R6G);
(xii) the first lumophore is palladium 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin (PdTFPP) and the second lumophore is 3-(2-benzothiazolyl)-7-(diethylamino) coumarin (C6);
(xiii) the first lumophore is palladium 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin (PdTFPP) and the second lumophore is 2,3,6,7-tetrahydro-9-trifluoromethyl-1H,5H-quinolizino(9,1-gh) coumarin (C153);
(xiv) the first lumophore is 4,7-diphenyl-1,10′-phenanthroline ([Ru(dpp)3]2+) and the second lumophore is 7-benzylamino-4-nitrobenz-2-oxa-1,3-diazole (BBD);
(xv) the first lumophore is platinum 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin (PtTFPP) and the second lumophore is 7-benzylamino-4-nitrobenz-2-oxa-1,3-diazole (BBD);
or
(xvi) the first lumophore is palladium 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin (PdTFPP) and the second lumophore is 7-benzylamino-4-nitrobenz-2-oxa-1,3-diazole (BBD).

14 more elements

Facts

Application

17/271,218Filed 31 Aug 2019

Priority

EP 181923293 Sep 2018

Published

US 2021/0246326 A112 Aug 2021

Granted

31 Dec 2024

Term ends

Not estimatedThe source records don’t support an estimate.

Classification12 codes

C09D 11/50
Inks: sympathetic, colour changing or similar inks
C09K 11/06
Luminescent materials, e.g. electroluminescent or chemiluminescent: containing organic luminescent materials
C09K 11/07
Containing organic luminescent materials: having chemically-interreactive components, e.g. reactive chemiluminescent compositions
G01N 21/29
Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands: using…