IP Library Granted Patent US 10,265,275
Granted Patent B2
US 10,265,275 · App. 14/187,741 · Granted Apr 23, 2019

Phenolic coatings and methods of making and using same

Inventors: Phillip B. Messersmith (Clarendon Hills, IL); Tadas S. Sileika (Northbrook, IL); Ran Zhang (Evanston, IL); Devin G. Barrett (Evanston, IL)
Assignee: Northwestern University
A61K31/05A01N31/16A01N43/16A61K31/192A61K31/353A61K31/7028A61K31/7034B01D15/08C02F1/285C02F1/288C08G65/44C08J7/065C09D4/00C09D5/00A61K36/00C02F2101/20C02F2101/22C02F2305/00C08J2369/00
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Quick Facts
Patent No.
US 10,265,275
App. No.
14/187,741
Granted
Apr 23, 2019
Kind
B2
Abstract

A method of making a facile, surface-independent, polyphenol coating is disclosed. In general, the method includes contacting at least a portion of the substrate to be coated with an aqueous solution containing one or more salts and one or more nitrogen-free phenolic compounds. Substrates of all kinds may be used, and compounds used to make the coating may include epigallocatechin-3-gallate (EGCG), epigallocatechin (EGC) and epicatechin-3-gallate (ECG), tannic acid, gallic acid, pyrogallol, and/or other nitrogen-free phenolic compounds. The coating made using the method, methods of using the coating, and kits comprising the coating precursors are also disclosed.

Claims (16)

1. A method of forming a coating on a substrate surface, the method comprising contacting at least a portion of the substrate surface with an aqueous solution comprising one or more salts selected from the group consisting of NaCl, NaNO 3 , Na 2 SO 4 , KCl, K 2 SO 4 , MgCl 2 , CaCl 2 , CuCl 2 , and ZnCl 2 , and an effective amount of one or more natural or synthetic nitrogen-free phenolic compounds selected from the group consisting of pyrogallol (PG), epigallocatechin-3-gallate (EGCG), epigallocatechin (EGC), epicatechin gallate (ECG), hydroxyhydroquinone (HHQ), catechin, morin, quercetin, naringenin, naringin, rutin, phloroglucinol, phenol, gallic acid, and isomers thereof, comprising 1) preparing the aqueous saline solution comprising the one or more natural or synthetic nitrogen-free phenolic compounds, and 2) applying the aqueous saline solution to the substrate; wherein pH and the salt concentration are such that a coating forms on the substrate surface, which has a thickness greater that a coating formed under identical conditions, in the absence of the salt.

2. The method of claim 1 , wherein the one or more salts are selected from the group consisting of NaCl, NaNO 3 , Na 2 SO 4 , KCl, K 2 SO 4 , MgCl 2 , and CaCl 2 .

3. The method of claim 1 , wherein the aqueous solution comprises more than one salt.

4. The method of claim 1 , wherein the aqueous solution further comprises a buffer.

5. The method of claim 1 , wherein the one or more natural or synthetic nitrogen-free phenolic compounds are selected from the group consisting of pyrogallol (PG), epigallocatechin-3-gallate (EGCG), hydroxyhydroquinone (HHQ), and isomers thereof, and wherein the pH of the aqueous solution is from 6.0 to 9.0.

6. The method of claim 1 , the method further comprising the step of contacting the resulting coating with a reactive moiety, whereby the reactive moiety reacts with and becomes bound to the coating.

7. The method of claim 6 , wherein the reactive moiety comprises a nucleophile or a metal ion.

8. The method of claim 7 , wherein the metal ion is selected from the group consisting of silver and gold ions.

9. The method of claim 7 , wherein the nucleophile is comprised of an amine- or thiol-functionalized poly(ethylene glycol) (PEG).

10. A coating on a substrate surface as produced by the method of claim 1 .

11. A method of providing antioxidant properties to a substrate comprising depositing an antioxidant coating on a substrate surface according to the method of claim 1 , whereby the coated substrate reduces the concentration of radicals and/or reactive oxygen species.

12. A method of providing anti-inflammatory properties to a substrate comprising depositing an anti-inflammatory coating on a substrate surface according to the method of claim 1 , whereby the coated substrate exhibits a attenuated acute inflammatory response through reduction of pro-inflammatory factors.

13. A method of inhibiting microbial growth on a substrate comprising depositing a coating on a substrate surface according to the method of claim 1 , whereby the coated substrate effectively kills microbes on contact or inhibits microbial growth.

14. A method of removing metal ions from a liquid, comprising contacting the liquid with the coating of claim 1 , whereby at least some of the metal ions in the sample are captured by the coating and removed from the liquid sample.

15. The method of claim 14 , wherein the metal ions are selected from the group consisting of lead, cadmium, copper, mercury, and chromium.

16. A method of forming a coating on a substrate surface, the method comprising contacting at least a portion of the substrate surface with an aqueous solution comprising an effective amount of one or more natural or synthetic nitrogen-free phenolic compounds selected from the group consisting of pyrogallol (PG), epigallocatechin-3-gallate (EGCG), tannic acid (TA), hydroxyhydroquinone (HHQ), and isomers thereof, one or more salts selected from the group consisting of NaCl, NaNO 3 , Na 2 SO 4 , KCl, K 2 SO 4 , MgCl 2 , CaCl 2 , CuCl 2 , and ZnCl 2 , wherein the pH of the aqueous solution is from 3.0 to 9.0, comprising 1) preparing the aqueous saline solution comprising the one or more natural or synthetic nitrogen-free phenolic compounds, and 2) applying the aqueous saline solution to the substrate; whereby a coating forms on the substrate surface, wherein pH and the salt concentration are such that a coating forms on the substrate surface, which has a thickness greater that a coating formed under identical conditions, in the absence of the salt.

Assignments (2)
CONFIRMATORY LICENSE Recorded Mar 5, 2014
From: NORTHWESTERN UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 032387/0866 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2014
From: BARRETT, DEVIN G.; MESSERSMITH, PHILLIP B.; SILEIKA, TADAS S.; ZHANG, RAN
To: NORTHWESTERN UNIVERSITY
Reel/Frame 032301/0560 →
Continuity (3)
Continuation 14162253 · Jan 23, 2014
Provisional Application 61756029 · Jan 24, 2013
Related Publication 20140228306A1 · Aug 14, 2014
Cited By (1)
US 12,605,477