Dihydropyridazine-based antioxidants and uses thereof

Patent metadata

Field	Value
Publication number	US-10851192-B2
Application number	US-201815969608-A
Country	US
Kind code	B2
Filing date	May 2, 2018
Priority date	Aug 11, 2015
Publication date	Dec 1, 2020
Grant date	Dec 1, 2020

Abstract

Dihydropyridazines compounds having antioxidant properties and uses thereof are described herein. These compounds can function as antioxidants that prevent oxidation of materials, including polymers, and as free radical inhibitors to stabilize reactive chemicals, such as monomers against free radical reactions. The dihydropyridazines can be added as small molecule additives or they can be incorporated into molecules bearing dienophilic C═C double bonds through a Carboni Lindsey reaction, which can reduce environmental and health exposure to antioxidants in plastics and allow for a greater quantity of the antioxidants to be used.

First claim

What is claimed is:

1. A method for inhibiting or delaying oxidation of an oxidizable material, comprising adding an antioxidant to the oxidizable material, wherein the antioxidant comprises a dihydropyridazine compound, wherein the dihydropyridazine compound is a 1,4-dihydropyridazine according to the formula:

wherein R is an H, Cl, Br, F, alkyl, aryl, O-alkyl, S-alkyl, S-aryl, NH 2 , NH-Alkyl, NH-Aryl, N-(Alkyl) 2 , N-(Aryl) 2 , NHNH 2 , N═CRR′, vinyl, alkenyl, CO 2 -Alkyl, CO 2 -Aryl, CONH 2 , CONH-Alkyl, CONH-Aryl, CON-(Alkyl) 2 , CON-(Aryl) 2 , or CN, and
wherein R′ and R″ are each independently an alkyl, aryl, alkenyl, an oligomer, or a polymer,
wherein when the dihydropyridazine compound and oxidizable material are exposed to an oxidizing species, the dihydropyridazine compound is oxidized to consume the oxidizing species, thereby preventing or hindering the oxidizing species from oxidizing the oxidizable material wherein an amount of said dihydropyridazine compound is sufficient to inhibit or delay oxidation of said oxidizable material,
wherein the oxidizable material is an unsaturated compound, wherein the unsaturated compound is an unsaturated oil, an unsaturated lipid, an unsaturated fat, or an unsaturated monomer.

2. The method of claim 1 , wherein the unsaturated compound is an unsaturated monomer, wherein the dihydropyridazine compound inhibits or delays polymerization of the unsaturated monomer.

3. The method of claim 2 , wherein the unsaturated monomer is a styrenic monomer, an ethylene monomer, a propylene monomer, a vinylic monomer, a diene monomer, an acrylate monomer, or a monomer having one or more double bonds.

4. A method for inhibiting or delaying oxidation of an oxidizable material, comprising adding an antioxidant to the oxidizable material, wherein the antioxidant comprises a dihydropyridazine compound, wherein adding the antioxidant to the oxidizable material comprises dissolving the dihydropyridazine compound in the oxidizable material,
wherein the dihydropyridazine compound is a 1,4-dihydropyridazine according to the formula:

wherein R is an H, Cl, Br, F, alkyl, aryl, O-alkyl, S-alkyl, S-aryl, NH 2 , NH-Alkyl, NH-Aryl, N-(Alkyl) 2 , N-(Aryl) 2 , NHNH 2 , N═CRR′, vinyl, alkenyl, CO 2 -Alkyl, CO 2 -Aryl, CONH 2 , CONH-Alkyl, CONH-Aryl, CON-(Alkyl) 2 , CON-(Aryl) 2 , or CN, and
wherein R′ and R″ are each independently an alkyl, aryl, alkenyl, an oligomer, or a polymer,
wherein when the dihydropyridazine compound and oxidizable material are exposed to an oxidizing species, the dihydropyridazine compound is oxidized to consume the oxidizing species, thereby preventing or hindering the oxidizing species from oxidizing the oxidizable material, wherein an amount of said dihydropyridazine compound is sufficient to inhibit or delay oxidation of said oxidizable material.

5. A method for inhibiting or delaying oxidation of an oxidizable material, comprising adding an antioxidant to the oxidizable material, wherein the antioxidant comprises a dihydropyridazine compound, wherein adding the antioxidant to the oxidizable material comprises coating the oxidizable material with a film comprising said antioxidant,
wherein the dihydropyridazine compound is a 1,4-dihydropyridazine according to the formula:

wherein R is an H, Cl, Br, F, alkyl, aryl, O-alkyl, S-alkyl, S-aryl, NH 2 , NH-Alkyl, NH-Aryl, N-(Alkyl) 2 , N-(Aryl) 2 , NHNH 2 , N═CRR′, vinyl, alkenyl, CO 2 -Alkyl, CO 2 -Aryl, CONH 2 , CONH-Alkyl, CONH-Aryl, CON-(Alkyl) 2 , CON-(Aryl) 2 , or CN, and
wherein R′ and R″ are each independently an alkyl, aryl, alkenyl, an oligomer, or a polymer,
wherein when the dihydropyridazine compound and oxidizable material are exposed to an oxidizing species, the dihydropyridazine compound is oxidized to consume the oxidizing species, thereby preventing or hindering the oxidizing species from oxidizing the oxidizable material, wherein an amount of said dihydropyridazine compound is sufficient to inhibit or delay oxidation of said oxidizable material.

6. The method of claim 5 , wherein the oxidizable material is a metallic substrate, wherein adding the antioxidant to the oxidizable material comprises coating the metallic substrate with the film comprising the dihydropyridazine compound, wherein the dihydropyridazine compound inhibits or delays corrosion of the metallic substrate.

Assignees

• Univ Arizona

Inventors

• Loy Douglas A
• Bagge Robb E

Classifications

• C07D237/04 Primary

  having less than three double bonds between ring members or between ring members and non-ring members · CPC title

• C08F236/20 Primary

  unconjugated · CPC title