Leuco compounds

Patent metadata

Field	Value
Publication number	US-11236235-B2
Application number	US-201816157903-A
Country	US
Kind code	B2
Filing date	Oct 11, 2018
Priority date	Oct 12, 2017
Publication date	Feb 1, 2022
Grant date	Feb 1, 2022

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.

First claim

We claim:

1. 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 R o , R m and R p group on each of rings A, B and C is independently selected from the group consisting of hydrogen, deuterium and R 5 ; wherein each R 5 is independently selected from the group consisting of halogens, nitro, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, —(CH 2 ) n —O—R 1 , —(CH 2 ) n —NR 1 R 2 , —C(O)R 1 , —C(O)OR 1 , —C(O)O − , —C(O)NR 1 R 2 , —OC(O)R 1 , —OC(O)OR 1 , —OC(O)NR 1 R 2 , —S(O) 2 R 1 , —S(O) 2 OR 1 , —S(O) 2 O − , —S(O) 2 NR 1 R 2 , —NR 1 C(O)R 2 , —NR 1 C(O)OR 2 , —NR 1 C(O)SR 2 , —NR 1 C(O)NR 2 R 3 , —P(O) 2 R 1 , —P(O)(OR 1 ) 2 , —P(O)(OR 1 )O − , and —P(O)(O − ) 2 , wherein the index n is an integer from 0 to 4, wherein any two of R 1 , R 2 and R 3 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—, —NR 15 —, and —S—; wherein at least one of the R o and R m groups on at least one of the three rings A, B or C is hydrogen; each R p is independently selected from hydrogen, —OR 1 and —NR 1 R 2 ;
wherein G is independently selected from the group consisting of hydrogen, deuterium, C 1 -C 16 alkoxide, phenoxide, bisphenoxide, nitrite, and nitrile;
wherein R 1 , R 2 , R 3 , and R 15 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, and R 4 ; wherein R 4 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 R 131 and R 137 are independently selected from the group consisting of —C(O)O—, —C(O)—, —S(O) 2 O—, and —S(O) 2 —; wherein R 132 and R 138 are independently selected from hydrogen, charge balancing counterions and R 143 wherein R 133 , R 134 , R 135 , R 136 , R 139 , R 140 , R 141 , R 142 and R 143 are independently selected from the group consisting of hydrogen, deuterium and R 5 ; wherein each R 5 is independently selected from the group consisting of halogens, nitro, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, —(CH 2 ) n —O—R 1 , —(CH 2 ) n —NR 1 R 2 , —C(O)R 1 , —C(O)OR 1 , —C(O)O − , —C(O)NR 1 R 2 , —OC(O)R 1 , —OC(O)OR 1 , —OC(O)NR 1 R 2 , —S(O) 2 R 1 , —S(O) 2 OR 1 , —S(O) 2 O—, —S(O) 2 NR 1 R 2 , —NR 1 C(O)R 2 , —NR 1 C(O)OR 2 , —NR 1 C(O)SR 2 , —NR 1 C(O)NR 2 R 3 , —P(O) 2 R 1 , P(O)(OR 1 ) 2 —P(O)(OR 1 )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 R 1 , R 2 and R 3 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—, —NR 15 —, and —S—; wherein R 1 , R 2 , R 3 , and R 15 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, and R 4 ; wherein R 4 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 R 121 and R 122 are independently selected from the group consisting of triarylmethane leuco moieties of Formula (I).

Assignees

• Milliken & Co

Inventors

• Valenti Dominick J
• Dey Sanjeev K
• Qin Haihu
• Freund Wesley A
• Miracle Gregory S

Classifications

• C09B23/148 Primary

  Stilbene dyes containing the moiety -C6H5-CH=CH-C6H5 (stilbene azo dyes C09B29/00) · CPC title

• C09B17/02

  of the benzene series · CPC title

• C09B21/00

  Thiazine dyes · CPC title

• C09B67/0034 Primary

  Mixtures of two or more pigments or dyes of the same type · CPC title

• C09B19/00

  Oxazine dyes · CPC title