Alkylated iminodibenzyls as antioxidants

• US 6,930,183 B2
• Filed: 04/17/2003
• Issued: 08/16/2005
• Est. Priority Date: 04/17/2003
• Status: Expired due to Term

• Current Assignee: Chemtura Corporation (Lanxess AG)
• Original Assignee: Crompton Corporation (Lanxess AG)
• Inventors: Nalesnik, Theodore E., Duyck, Karl J.
• Primary Examiner(s): Kifle, Bruck
• Application Number:
  US10/417,861
• Publication Number:
  US 20040214813A1
• Time in Patent Office: 852 Days
• Field of Search: 540/588
• US Class Current: 540/588
• CPC Class Codes: C07D 223/22 Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines

Abstract

Disclosed herein is an antioxidant that is an alkylated iminodibenzyl of the general formula:
wherein:

• • R₁, R₂, R₃, and R₄ are independently selected from the group consisting of hydrogen, alkyl moieties, and alkenyl moieties; and
  • R₅, R₆, R₇, and R₈ are independently selected from the group consisting of hydrocarbyl moieties and hydrogen.

Claims

1. A compound of the formula:

wherein;

R₁ is selected from the group consisting of alkenyl moieties of from 3 to 32 carbon atoms;

R₂, R₃, and R₄ are independently selected from the group consisting of hydrogen, alkyl moieties of from 3 to 32 carbon atoms, and alkenyl moieties of from 3 to 32 carbon atoms; and

R₅, R₆, R₇, and R₈ are independently selected from the group consisting of hydrogen;

unsubstituted phenyl;

phenyl substituted with one or more alkyl groups;

phenyl substituted with one or more alkoxy groups;

phenyl substituted with one or more alkyl amino or aryl amino groups;

naphthyl and alkyl substituted naphthyl;

straight chain or branched chain alkyl or alkenyl groups containing from one to twenty carbon atoms; and

cyclic alkyl groups.

2. The compound of claim 1 wherein R₅, R₆, R₇, and R₈ are independently selected from the group consisting of hydrogen;

unsubstituted phenyl;

phenyl substituted with one or more alkyl groups;

phenyl substituted with one or more alkoxy groups;

phenyl substituted with one or more alkyl amino or aryl amino groups;

naphthyl and alkyl substituted naphthyl;

straight chain or branched chain alkyl or alkenyl groups; and

cyclic alkyl groups;

wherein said alkyl, alkoxy, alkyl amino, alkyl substituted naphthyl and alkenyl groups are of from 1 to 20 carbon atoms.

7. The compound of claim 1 wherein at least one of R₂, R₃, and R₄ is an alkyl moiety selected from the group consisting of pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetrdecyl, pentacyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, hentriacontyl, dontriacontyl, and isomers of the foregoing.

8. The compound of claim 7 wherein at least one of R₂, R₃, and R₄ is nonyl.

9. The compound of claim 1 wherein at least one of R₂, R₃, and R₄ is an alkenyl moiety of from 3 to 32 carbon atoms.

3. A composition comprising:

A) an organic product selected from the group consisting of lubricants, hydraulic fluids, metal-working fluids, fuels, and polymers; and

B) a stabilizing amount of a compound of the formula;

wherein;

R₁ is selected from the group consisting of alkenyl moieties of from 3 to 32 carbon atoms;

R₂, R₃, and R₄ are independently selected from the group consisting of hydrogen, alkyl moieties of from 3 to 32 carbon atoms, and alkenyl moieties of from 3 to 32 carbon atoms; and

R₅, R₆, R₇, and R₈ are independently selected from the group consisting of hydrogen;

unsubstituted phenyl;

phenyl substituted with one or more alkyl groups;

phenyl substituted with one or more alkoxy groups;

phenyl substituted with one or more alkyl amino or aryl amino groups;

naphthyl and alkyl substituted naplthyl;

straight chain or branched chain alkyl or alkenyl groups containing from one to twenty carbon atoms; and

cyclic alkyl groups.

4. The composition of claim 3 wherein R₅, R₆, R₇, and R₈ are independently selected from the group consisting of hydrogen;

unsubstituted phenyl;

phenyl substituted with one or more alkyl groups;

phenyl substituted with one or more alkoxy groups;

phenyl substituted with one or more alkyl amino or aryl amino groups;

naphthyl and alkyl substituted naphthyl;

straight chain or branched chain alkyl or alkenyl groups; and

cyclic alkyl groups;

wherein said alkyl alkoxy, alkyl amino, alkyl substituted naphthyl and alkenyl groups are of from 1 to 20 carbon atoms.

5. A method for inhibiting the oxidation of an organic product selected from the group consisting of lubricants, hydraulic fluids, metal-working fluids, fuels, and polymers comprising adding to said product a stabilizing amount of a compound of the formula:

wherein;

R₁ is selected from the group consisting of alkenyl moieties of from 3 to 32 carbon atoms;

R₂, R₃, and R₄ are independently selected from the group consisting of hydrogen, alkyl moieties of from 3 to 32 carbon atoms, and alkenyl moieties of from 3 to 32 carbon atoms; and

R₅, R₆, R₇, and R₈ are independently selected from the group consisting of hydrogen;

unsubstituted phenyl;

phenyl substituted with one or more alkyl groups;

phenyl substituted with one or more alkoxy groups;

phenyl substituted with one or more alkyl amino or aryl amino groups;

naphthyl and alkyl substituted naphthyl;

straight chain or branched chain alkyl or alkenyl groups containing from one to twenty carbon atoms; and

cyclic alkyl groups.

6. The method of claim 5 wherein R₅, R₆, R₇, and R₈ are independently selected from the group consisting of hydrogen;

unsubstituted phenyl;

phenyl substituted with one or more alkyl groups;

phenyl substituted with one or more alkoxy groups;

phenyl substituted with one or more alkyl amino or aryl amino groups;

naphthyl and alkyl substituted naphthyl;

straight chain or branched chain alkyl or alkenyl groups; and

cyclic alkyl groups;

wherein said alkyl, alkoxy, alkyl amino, alkyl substituted naphthyl and alkenyl groups are of from 1 to 20 carbon atoms.