Substituted benzotriazole phenolate salts and antioxidant compositions formed therefrom

Patent metadata

Field	Value
Publication number	US-11078419-B2
Application number	US-202016780323-A
Country	US
Kind code	B2
Filing date	Feb 3, 2020
Priority date	Jul 7, 2015
Publication date	Aug 3, 2021
Grant date	Aug 3, 2021

Abstract

A class of antioxidant compositions include benzotriazole phenolate salts with substituents either ortho to the phenol hydroxide group and/or para to the phenol hydroxide group can be prepared from substituted benzotriazole phenols. The ortho substituent group can be a simple hydrocarbon, alkoxy or amino group, or the ortho substituent group can be a linking group, linking the benzotriazole phenolate to another benzotriazole phenolate group.

First claim

What is claimed is:

1. An antioxidant composition comprising one or more macromolecular salt compositions, the macromolecular salt composition comprising an assembly of metal salts comprising repeat units of the structure:

wherein X comprises a —O—, —S—, —S(O) 2 —, or —NR 10 —linking group where R 10 comprises a hydrogen atom, an alkyl group, or an aryl group;
each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 , independently comprises a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a halogen atom;
m=0.5, 1, or 2;
M is a metal ion with a valency of 2m such that M is lithium sodium or potassium when m=0.5;
M is calcium, magnesium, or cobalt, when m=1; and M is vanadium or titanium when m=2.

2. The antioxidant composition of claim 1 , wherein X comprises a —NR 10 —linking group, where R 10 comprises a hydrogen atom or an alkyl group comprising 1-3 carbon atoms, and R 3 and R 16 each comprises an alkyl group with 1-20 carbon atoms.

3. The antioxidant composition of claim 1 , wherein X comprises a —NR 10 —linking group, where R 10 comprises a hydrogen atom, and R 3 and R 16 each comprises an alkyl group with 8 carbon atoms.

4. The antioxidant composition of claim 1 , wherein X comprises a —NR 10 —linking group, where R 10 comprises a methyl group, and R 3 and R 16 each comprises an alkyl group with 8 carbon atoms.

5. The antioxidant composition of claim 1 , wherein X comprises a —S—linking group, and R 3 and R 16 each comprises an alkyl group with 1-20 carbon atoms.

6. The antioxidant composition of claim 1 , wherein X comprises a —S—linking group, and R 3 and R 16 each comprises an alkyl group with 8 carbon atoms.

7. The antioxidant composition of claim 1 , wherein X comprises a —O—linking group, and R 3 and R 16 each comprises an alkyl group with 1-20 carbon atoms.

8. The antioxidant composition of claim 1 , wherein X comprises a —O—linking group, and R 3 and R 16 each comprises an alkyl group with 8 carbon atoms.

9. A macromolecular salt composition comprising an assembly of metal salts comprising repeat units of a substituted benzotriazole phenolate anion and a metal cation with the structure:

wherein X comprises a —O—, —S—, —S(O)—, —S(O) 2 —, or —NR 10 —linking group where R′° comprises a hydrogen atom, an alkyl group, or an aryl group;
each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 , independently comprises a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a halogen atom;
m=0.5, 1, or 2;
M is a metal ion with a valency of 2m such that M is lithium sodium or potassium when m=0.5;
M is calcium, magnesium, or cobalt, when m=1; and M is vanadium or titanium when m=2.

10. The salt composition of claim 9 , wherein X comprises a —NR 10 —linking group, where R 10 comprises a hydrogen atom or an alkyl group comprising 1-3 carbon atoms, and R 3 and R 16 each comprises an alkyl group with 1-20 carbon atoms.

11. The salt composition of claim 9 , wherein X comprises a —NR 10 —linking group, where R 10 comprises a hydrogen atom, and R 3 and R 16 each comprises an alkyl group with 8 carbon atoms.

12. The salt composition of claim 9 , wherein X comprises a —NR 10 —linking group, where R 10 comprises a methyl group, and R 3 and R 16 each comprises an alkyl group with 8 carbon atoms.

13. The salt composition of claim 9 , wherein X comprises a —S—linking group, and R 3 and R 16 each comprises an alkyl group with 1-20 carbon atoms.

14. The salt composition of claim 9 , wherein X comprises a —S—linking group, and R 3 and R 16 each comprises an alkyl group with 8 carbon atoms.

15. The salt composition of claim 9 , wherein X comprises a —O—linking group, and R 3 and R 16 each comprises an alkyl group with 1-20 carbon atoms.

16. The salt composition of claim 9 , wherein X comprises a —O—linking group, and R 3 and R 16 each comprises an alkyl group with 8 carbon atoms.

Assignees

• 3M Innovative Properties Co

Inventors

• Schultz Nathan E
• Li Fuming B
• Volp Kelly A
• Mccormick Mark

Classifications

• C08K5/3475

  condensed with carbocyclic rings · CPC title

• C08L23/12

  Polypropene · CPC title

• G01R33/46

  NMR spectroscopy · CPC title

• C09K15/326 Primary

  containing only metals · CPC title

• C09K15/24

  containing a phenol or quinone moiety · CPC title