Antioxidant amines based on n-(4aniliophenyl) amides antioxidant amines based on n-(4-anilinophenyl) amides
View Patent ↗A composition of matter is disclosed wherein the composition comprises an N-aromatic substituted acid amide compound selected from the group consisting of compounds of formula (I) wherein A and B are independently selected alkylene groups; R 1 is selected from the group consisting of hydrogen, alkyl, alkylether, or ester; R 2 is hydrogen if R 1 is hydrogen; R 2 is an alkyl primary amine if R 1 is alkyl, alkylether, or ester; R 3 and R 4 are independently selected from the group consisting of hydrogen and alkyl; R 5 is a sterically hindered phenolic group of formula (II) or formula (III) wherein X is CH 2 , S, NH, or O; and m, n, and p are independently selected integers equal to 0 or 1. These compositions may be used as such or they may be bound to a polymer backbone via a linking moiety. In either case, they are useful as antioxidants, particularly in lubricating oil compositions
1. A composition of matter comprising an N-aromatic substituted acid amide compound selected from the group consisting of compounds of the formula:
wherein
A and B are independently selected alkylene groups;
R 1 is selected from the group consisting of hydrogen, alkyl, alkylether, or ester;
R 2 is hydrogen if R 1 is hydrogen;
R 2 is an alkyl primary amine if R 1 is alkyl, alkylether, or ester;
R 3 and R 4 are independently selected from the group consisting of hydrogen and alkyl;
R 5 is a sterically hindered phenolic group,
wherein
X is CH 2 , S, NH, or O; and
m, n, and p are independently selected integers equal to 0 or 1.
2. The composition of claim 1 wherein R 5 is
3. The composition of claim 1 wherein n is 0.
4. The composition of claim 1 wherein n is 1 and A is propylene.
5. The composition or claim 1 wherein R 1 and R 2 are both hydrogen.
6. The composition of claim 1 wherein R 1 is not hydrogen and R 2 is an alkyl primary amine.
7. The composition of claim 1 wherein m is 1 and B is methylene.
8. The composition of claim 1 wherein the N-aromatic substituted acid amide compound is 3-amino-N-(4-anilinophenyl)-butanamide, 3-amino-N-(4-anilinophenyl)-N-isopropyl butanamide, or N-(4-anilinophenyl)-3-{(3-aminopropyl)-(cocoalkyl)amino}butanamide.
9. A reaction product comprised of a carboxylic acid material bound to a substantially linear polymer, copolymer, or terpolymer, further reacted with an N-aromatic substituted acid amide moiety selected from the group consisting of compounds of the formula:
wherein
A and B are independently selected alkylene groups;
R 1 is selected from the group consisting of hydrogen, alkyl, alkylether, or ester;
R 2 is hydrogen if R 1 is hydrogen;
R 2 is an alkyl primary amine if R 1 is alkyl, alkylether, or ester;
R 3 and R 4 are independently selected from the group consisting of hydrogen and alkyl;
R 5 is a sterically hindered phenolic group,
wherein
X is CH 2 , S, NH, or O; and
m, n, n, and p are independently selected integers equal to 0 or 1.
10. A lubricating oil composition comprising a major portion of lubricating oil and a minor portion of an additive that is an N-aromatic substituted acid amide compound or the reaction product comprised of a carboxylic acid material bound to a substantially linear polymer, copolymer, or terpolymer, further reacted with an N-aromatic substituted acid amide moiety, wherein said N-aromatic substituted acid amide is selected from the group consisting of compounds of the formula:
wherein
A and B are independently selected alkylene groups;
R 1 is selected from the group consisting of hydrogen, alkyl, alkylether, or ester;
R 2 is hydrogen if R 1 is hydrogen;
R 2 is an alkyl primary amine if R 1 is alkyl, alkylether, or ester;
R 3 and R 4 are independently selected from the group consisting of hydrogen and alkyl;
R 5 is a sterically hindered phenolic group,
wherein
X is CH 2 , S, NH, or O; and
m, n, and p are independently selected integers equal to 0 or 1.
11. The lubricating oil composition of claim 10 further comprising a zinc dialkyldithiophosphate.
12. A composition of matter comprising a solution comprising:
(i) a reaction product comprised of a carboxylic acid material bound to a substantially linear polymer, copolymer, or terpolymer, further reacted with an N-aromatic substituted acid amide moiety selected from the group consisting of compounds of the formula:
wherein
A and B are independently selected alkylene groups;
R 1 is selected from the group consisting or hydrogen, alkyl, alkylether, or ester;
R 2 is hydrogen if R 1 is hydrogen;
R 2 is an alkyl primary amine if R 1 is alkyl, alkylether, or ester;
R 3 and R 4 are independently selected from the group consisting of hydrogen and alkyl;
R 5 is a sterically hindered phenolic group,
wherein
X is CH 2 , S, NH, or O; and
m, n, and p are independently selected integers equal to 0 or 1; and
(ii) an oil solvent.
13. The composition of claim 12 wherein the oil solvent is mineral oil.
14. The composition of claim 12 further comprising a co-solvent.
15. The composition of claim 14 wherein the co-solvent is an alkyl, dialkyl, or mixed dialkyl phenol wherein each alkyl group is selected from the group consisting of alkyls is of from 6 to 22 carbon atoms.
16. A composition of matter comprising a solution comprising:
A) a reaction product comprised of a carboxylic acid material bound to a substantially linear polymer, copolymer, or terpolymer, further reacted with an N-alkyl imidazole;
B) an oil solvent; and
C) a co-solvent comprising an alkyl, dialkyl, or mixed dialkyl phenol, wherein the alkyl group is selected from the group consisting of alkyls of from 6 to 22 carbon atoms.