Antioxidants and methods to maximize performance

Patent metadata

Field	Value
Publication number	US-10323017-B2
Application number	US-201615548512-A
Country	US
Kind code	B2
Filing date	Feb 5, 2016
Priority date	Feb 6, 2015
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

A method of preventing or reducing the level of degradation of an organic substrate is described, wherein a composition is formed that includes the organic substrate together with an effective amount of a sacrificial base and a diarylamine antioxidant.

First claim

We claim:

1. A composition comprising a base and an antioxidant, wherein the base is 2,4,6-tri-tert-butylpyridine (TTBP), cesium carbonate, tert-alkylated primary amine, a metal oxide, metal hydroxide, or metal carbonate, wherein the metal of the metal oxide, metal hydroxide or metal carbonate is sodium, potassium, magnesium, calcium, or barium and the antioxidant comprises a compound of Formula II, or a salt thereof,

wherein each of X, Y, and Z are independently a carbon or nitrogen atom, and at least one of X, Y, or Z are nitrogen,
wherein R 1 is an electron donating group, and R 2 is a hydrogen or an electron donating group bonded to a carbon atom in its aryl ring,
wherein an electron donating group comprises a hydrocarbon group, an alkoxy group (OR 3 ), an amine group (NH 2 ), a monosubstituted amine (NHR 4 ) group, or a disubstituted amine (NR 4 R 5 ) group,
wherein R 3 , R 4 and R 5 are independently hydrogen, saturated or unsaturated branched or straight chain hydrocarbon moiety, cycloaliphatic group, aromatic hydrocarbon, or a combination thereof,
wherein the carbon atoms at positions 9 and 13 bear hydrogens, and
wherein when R 2 is OR 3 , R 2 is bonded to the carbon atom at position 11.

2. The composition of claim 1 , wherein the electron donating group is an amine or a tert-butyl group.

3. The composition of claim 2 , wherein the amine is a dialkylamine.

4. The composition of claim 1 , wherein the compound of Formula II, is compound 1, 2, 4, 5, 6, 20, 22-23, 26, or any salt thereof

5. The composition according to claim 1 , further comprising an organic substrate, wherein the organic substrate is a lubricant, biofuel, plastic, rubber, polymer, elastomer, cosmetic preparation, coating, dye, ink, pharmaceutical preparation, food preparation or adhesive.

6. The composition according to claim 1 , further comprising an organic substrate, wherein the organic substrate is a lubricant, and the compound(s) are present in an amount of about 0.01 to about 6 weight percent of said lubricant.

7. The composition according to claim 1 , wherein the composition further comprises one or more additional antioxidants.

8. The composition of claim 7 , wherein the additional antioxidant is a sterically hindered phenol.

9. The composition according to claim 7 , wherein the one or more additional antioxidants is selected from the group consisting of: traditional anti-oxidants, anti-wear agents, zinc salts, anti-deposition agents, hydrolytic stabilizers, friction modifiers, seal swell agents, anti-rust agents, foam suppressing agents, and pour point depressants.

10. A kit comprising a base selected from 2,4,6-tri-tert-butylpyridine (TTBP), cesium carbonate, tert-alkylated primary amine, a metal oxide, metal hydroxide, or metal carbonate, wherein the metal of the metal oxide, metal hydroxide or metal carbonate is sodium, potassium, magnesium, calcium, or barium and an antioxidant of Formula II, or any salt thereof,

wherein each of X, Y, and Z are independently a carbon or nitrogen atom, and at least one of X, Y, or Z are nitrogen,
wherein R 1 is an electron donating group, and R 2 is a hydrogen or an electron donating group bonded to a carbon atom in its aryl ring,
wherein an electron donating group comprises a hydrocarbon group, an alkoxy group (OR 3 ), an amine group (NH 2 ), a monosubstituted amine (NHR 4 ) group, or a disubstituted amine (NR 4 R 5 ) group,
wherein R 3 , R 4 and R 5 are independently hydrogen, saturated or unsaturated branched or straight chain hydrocarbon moiety, cycloaliphatic group, aromatic hydrocarbon, or a combination thereof,
wherein the carbon atoms at positions 9 and 13 bear hydrogens, and
wherein when R 2 is OR 3 , R 2 is bonded to the carbon atom at position 11, and
instructions to prevent or reduce degradation of the organic substrate by scavenging at least one free radical species from within a composition containing an organic substrate.

11. The kit of claim 10 , wherein the compound of Formula II, is compound 1, 2, 4, 5, 6, 20, 22-23, 26, or any salt thereof

12. The composition of claim 1 , further comprising an organic substrate,
wherein the organic substrate is an engine oil, automatic transmission fluid, crank case lubricant, industrial utility grade oil, compressor oil, gear oil, hydraulic oil, biodiesel, plastic, rubber, rubber-like substance, unsaturated monomer, elastomer, adhesive, cosmetic preparation, coating, dye, ink, pharmaceutical preparation, or combustion engine lubricating oil.

13. The composition of claim 1 , further comprising an organic substrate,
wherein the organic substrate is an oil, fat, or wax used in the cosmetic and/or pharmaceutical industry, including those oils, fats or waxes that comprise esters of fatty acids, oil, fat, or wax used in manufacturing of food or food ingredients, almond oil, apricot oil, castor oil, corn oil, macadamia nut oil, olive oil, sesame oil, soybean oil, fish oil, bird oil, jojoba oil, bees wax, lanolin, oleic acid, linoleic acid, linolenic acid, or esters thereof.

14. A method of preventing or reducing the level of degradation of an organic substrate, the method comprising:
adding to a composition that comprises an organic substrate, effective amounts of a composition of claim 1 .

15. The method of claim 14 , wherein the organic substrate is engine oil, automatic transmission fluid, crank case lubricant, industrial utility grade oil, compressor oil, gear oil, hydraulic oil, biodiesel, plastic, rubber, rubber-like substance, unsaturated monomer, elastomer, adhesive, cosmetic preparation, coating, dye, ink, pharmaceutical preparation, or combustion engine lubricating oil.

Assignees

• Univ Ottawa
• Alma Mater Studiorum—Universita di Bologna

Inventors

• Pratt Derek A
• Shah Ronak Mayankbhai
• Haidasz Evan Anthony
• Valgimigli Luca

Classifications

• C10M2215/221

  Six-membered rings containing nitrogen and carbon only · CPC title

• C10M2215/064

  Di- and triaryl amines · CPC title

• C10M2207/402

  Castor oils · CPC title

• C10M2207/026

  with tertiary alkyl groups · CPC title

• C10M2201/062

  Oxides; Hydroxides; Carbonates or bicarbonates · CPC title