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US 11,236,235 B2Granted
Leuco compounds
AssigneeMilliken & Company
InventorsDominick J. Valenti, Sanjeev K. Dey, Haihu Qin, Wesley A. Freund, Gregory S. Miracle
Life of this patent
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Abstract
A compound comprises at least one fluorescent moiety covalently bound to at least one second moiety selected from the group consisting of leuco moieties and chromophore moieties.
Claims1
A compound comprising at least one fluorescent moiety covalently bound to at least one second moiety selected from the group consisting of triarylmethane leuco moieties derived by removal of one or more hydrogen atoms from a structure of Formula (I)
- wherein each individual Ro, Rm and Rp group on each of rings A, B and C is independently selected from the group consisting of hydrogen, deuterium and R5;
- wherein each R5 is independently selected from the group consisting of halogens, nitro, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, —(CH2)n—O—R1, —(CH2)n—NR1R2, —C(O)R1, —C(O)OR1, —C(O)O−, —C(O)NR1R2, —OC(O)R1, —OC(O)OR1, —OC(O)NR1R2, —S(O)2R1, —S(O)2OR1, —S(O)2O−, —S(O)2NR1R2, —NR1C(O)R2, —NR1C(O)OR2, —NR1C(O)SR2, —NR1C(O)NR2R3, —P(O)2R1, —P(O)(OR1)2, —P(O)(OR1)O−, and —P(O)(O−)2, wherein the index n is an integer from 0 to 4, wherein any two of R1, R2 and R3 attached to the same heteroatom can combine to form a ring of five or more members optionally comprising one or more additional heteroatoms selected from the group consisting of —O—, —NR15—, and —S—;
- wherein at least one of the Ro and Rm groups on at least one of the three rings A, B or C is hydrogen;
- each Rp is independently selected from hydrogen, —OR1 and —NR1R2;
- wherein G is independently selected from the group consisting of hydrogen, deuterium, C1-C16 alkoxide, phenoxide, bisphenoxide, nitrite, and nitrile;
- wherein R1, R2, R3, and R15 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, and R4;
- wherein R4 is a organic group composed of one or more organic monomers with said monomer molecular weights ranging from 28 to 500;
- wherein any charge present in any of the structures is balanced with a suitable independently selected internal or external counterion;
- wherein the fluorescent moiety is selected from the group consisting of stilbene moieties and distyrylbiphenyl moieties;
- wherein, when the fluorescent moiety is a distyrylbiphenyl moiety, the fluorescent moiety is a univalent or polyvalent moiety derived by removal of one or more hydrogen atoms from a structure of Formula (CXXX)
- wherein R131 and R137 are independently selected from the group consisting of —C(O)O—, —C(O)—, —S(O)2O—, and —S(O)2—;
- wherein R132 and R138 are independently selected from hydrogen, charge balancing counterions and R143 wherein R133, R134, R135, R136, R139, R140, R141, R142 and R143 are independently selected from the group consisting of hydrogen, deuterium and R5;
- wherein each R5 is independently selected from the group consisting of halogens, nitro, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, —(CH2)n—O—R1, —(CH2)n—NR1R2, —C(O)R1, —C(O)OR1, —C(O)O−, —C(O)NR1R2, —OC(O)R1, —OC(O)OR1, —OC(O)NR1R2, —S(O)2R1, —S(O)2OR1, —S(O)2O—, —S(O)2NR1R2, —NR1C(O)R2, —NR1C(O)OR2, —NR1C(O)SR2, —NR1C(O)NR2R3, —P(O)2R1, P(O)(OR1)2—P(O)(OR1)O−, and —P(O)(O−)2, wherein the index n is an integer from 0 to 4, preferably from 0 to 1, most preferably 0;
- wherein any two of R1, R2 and R3 attached to the same heteroatom can combine to form a ring of five or more members optionally comprising one or more additional heteroatoms selected from the group consisting of —O—, —NR15—, and —S—;
- wherein R1, R2, R3, and R15 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, and R4;
- wherein R4 is an organic group composed of one or more organic monomers with said monomer molecular weights ranging from 28 to 500;
- and
- wherein, when the fluorescent moiety is a stilbene moiety, the compound has the structure of Formula (CXX)
- wherein each M is independently selected from the group consisting of hydrogen and charge balancing counterions, and R121 and R122 are independently selected from the group consisting of triarylmethane leuco moieties of Formula (I).
16 more elements
Dependencies are inferred from the claim text.