Near infrared absorbing fluorescent compositions

Patent metadata

Field	Value
Publication number	US-10377901-B2
Application number	US-201515503530-A
Country	US
Kind code	B2
Filing date	Aug 12, 2015
Priority date	Aug 12, 2014
Publication date	Aug 13, 2019
Grant date	Aug 13, 2019

Abstract

Provided herein are heterocyclic near infrared compounds, including near IR compounds defined by Formulae I-V described herein. The near infrared compounds can include a cyanine group, a phthalocyanine group, a naphthalocyanine group, a squaraine group, a carbocyanine group, or a combination thereof. In some embodiments, the near infrared compound can be charged. In some embodiments, the near infrared compound can comprise a cationic group. Compositions comprising the near infrared compounds are also disclosed. In some embodiments, the composition can contain the near infrared compound, a polymer, and an acceptable carrier. In some embodiments, the polymer can include an anionic group. The compositions can be used as a coating for marking a surface, such as an ink. The compositions can also be used on articles for detecting, identifying, or authenticating the article. Methods of making the compositions described herein are also disclosed.

First claim

What is claimed is:

1. A compound of Formula I:

or a salt or a hydrate thereof,
wherein R and R′ are independently selected from the group consisting of substituted or unsubstituted alkylaryl; substituted or unsubstituted alkylheteroaryl;
wherein R″ and R′″ are independently selected from the group consisting of hydrogen; halogen; alkyl, —OR 1 ; —NR 1 R 2 ; —NO 2 ; —CF 3 ; —CN; —C 2 R 1 ; —SR 1 ; —N 3 ; C(═O)R 1 ; —C(═O)OR 1 ; —OC(═O)R 1 ; —O(CR 1 R 2 ) r C(═O)R 1 ; —C(═O)NR 1 R 2 ; —NR 1 C(═O)R 2 ; —O(CR 1 R 2 ) r NR 2 C(═O)R 1 ; —O(CR 1 R 2 ) r NR 2 SO 2 R 1 ; —OC(═O)NR 1 R 2 ; —NR 1 C(═O)OR 2 ; —SO 2 R 1 ; —SO 2 NR 1 R 2 ; and —NR 1 SO 2 R 2 ; wherein R 1 and R 2 are individually hydrogen; substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted heterocyclyl; substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroalkyl, or substituted or unsubstituted alkylheteroaryl; and r is an integer from 1 to 6, and
wherein the compound of Formula I has a wavelength of maximum absorbance, λ max , in the near infrared (NIR) region.

2. The compound of claim 1 , wherein R and R′ are independently selected from the group consisting of benzyl, phenyl-ethyl, phenyl-propyl, and phenyl-butyl.

3. The compound of claim 1 , wherein the compound comprises an overall cationic charge.

4. A coating composition comprising a compound of claim 1 , a polymer, and an acceptable carrier.

5. The composition of claim 4 , wherein the compound interacts with the polymer through electrostatic forces, dipole-dipole interactions, hydrogen bonding, hydrophobic interactions, van der Waals forces, or combinations thereof.

6. The composition of claim 4 , wherein the polymer includes a substituted or unsubstituted polyamide, polyimide, polyester, polyacrylate, polyacrylic acid, polyether, vinylic polymer, polyimine, polysiloxane, polyurethane, polythioether, polycarbonate, polyolefin, polyarylalkylene, polysilane, polyesteramide, polyacetal, polysulfone, polystyrene, polyacrylamide, polyvinyl alcohol, polyphosphonite, polyphosphonate, cellulose, derivatives thereof, copolymers thereof, or blends thereof.

7. The composition of claim 6 , wherein the polymer comprises an anionic group.

8. The composition of claim 4 , wherein the compound is in an amount of from about 0.001% to about 5% by weight of the composition.

9. A method of making the composition according to claim 4 , comprising:
a. dissolving the polymer in a first solvent to form a polymer solution,
b. dissolving the compound in a second solvent to form a near infrared solution,
c. combining the near infrared solution and the polymer solution,
d. optionally evaporating the first solvent, the second solvent, or a combination thereof.

10. An article comprising a mark disposed on a first portion of the article, wherein the mark comprises a compound of claim 1 .

11. The compound of claim 1 , wherein R and R′ are independently substituted and independently comprises a cationic quaternary ammonium group or an iminium group.

Assignees

• Univ Georgia State Res Found

Inventors

• Henary Maged
• Patonay Gabor

Classifications

• G01N2021/6439

  with indicators, stains, dyes, tags, labels, marks · CPC title

• C09D7/41

  Organic pigments; Organic dyes · CPC title

• C09B57/007 Primary

  Squaraine dyes · CPC title

• C09B69/105

  containing a methine or polymethine dye · CPC title

• C09D101/10

  Esters of organic acids (of both organic acids and inorganic acids C09D101/20) · CPC title