Substituted diarylamines and use of same as antioxidants
A compound of Formula I, Formula IA, Formula IB, or Formula II, or an acid or base addition salt thereof, and use of these compounds as antioxidants. In one embodiment, a compound of Formula II, wherein each of X, Y, and Z are independently a carbon or nitrogen atom; R 1 and R 2 are each independently a hydrogen or an electron donating group, but are not both hydrogen, and wherein R 1 , and R 2 are each bonded to a carbon atom in their own respective aryl ring.
1. 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 compound of claim 1 wherein the electron donating group is:
(i) an aliphatic moiety, an aromatic moiety or a combination thereof;
(ii) OR 3 wherein R 3 is a hydrogen or an aliphatic moiety, an aromatic moiety or a combination thereof; or
(iii) NR 4 R 5 wherein R 4 and R 5 are each independently hydrogen or an aliphatic moiety, an aromatic moiety or a combination thereof.
3. The compound of claim 1 wherein the electron donating group is:
(i) a C 1 to C 20 hydrocarbon group;
(ii) OR 3 wherein R 3 is a hydrogen or a C 1 to C 20 hydrocarbon group; or
(iii) NR 4 R 5 wherein R 4 and R 5 are each independently hydrogen or a C 1 to C 20 hydrocarbon group.
4. The compound according to claim 1 , wherein R 4 and R 5 are not both hydrogen or R 3 is not a hydrogen.
5. The compound according to claim 3 , wherein the electron donating group is a linear or branched C 1 to C 20 hydrocarbon group.
6. The compound of claim 1 , wherein R 1 is:
(i) a C 1 to C 20 hydrocarbon group;
(ii) OR 3 wherein R 3 is a hydrogen or a C 1 to C 20 hydrocarbon group; or
(iii) NR 4 R 5 wherein R 4 and R 5 are each independently hydrogen or a C 1 to C 20 hydrocarbon group.
7. The compound of claim 1 , wherein R 2 is bonded to a carbon atom at position 11 and is:
(i) a hydrogen;
(ii) a C 1 to C 20 hydrocarbon group;
(iii) OR 3 wherein R 3 is a hydrogen or a C 1 to C 20 hydrocarbon group; or
(iv) NR 4 R 5 wherein R 4 and R 5 are each independently hydrogen or a C 1 to C 20 hydrocarbon group.
8. A composition comprising an organic substrate and one or more compounds 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, 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,
wherein when R 2 is OR 3 , R 2 is bonded to the carbon atom at position 11, and
wherein the compound(s) are present in an amount sufficient to reduce the level of degradation of the organic substrate when compared to the level of degradation of the organic substrate in the absence of said compound(s).
9. The composition of claim 8 wherein the electron donating group is:
(i) an aromatic moiety, an aliphatic moiety or a combination thereof;
(ii) OR 3 wherein R 3 is a hydrogen or an aromatic moiety, an aliphatic moiety or a combination thereof; or
(iii) NR 4 R 5 wherein R 4 and R 5 are each independently hydrogen or an aromatic moiety, an aliphatic moiety or a combination thereof.
10. The composition of claim 8 wherein the electron donating group is:
(i) a C 1 to C 20 hydrocarbon group;
(ii) OR 3 wherein R 3 is a hydrogen or a C 1 to C 20 hydrocarbon group; or
(iii) NR 4 R 5 wherein R 4 and R 5 are each independently hydrogen or a C 1 to C 20 hydrocarbon group.
11. The composition according to claim 9 , wherein R 4 and R 5 are not both hydrogen or R 3 is not a hydrogen.
12. The composition according to claim 10 , wherein R 4 and R 5 are not both hydrogen or R 3 is not a hydrogen.
13. The composition according to claim 8 , wherein the organic substrate is selected from the group consisting of: lubricants, biofuels, plastics, rubbers, polymers, elastomers, cosmetic preparations, coatings, dyes, inks, pharmaceutical preparations, food preparations and adhesives.
14. The composition according to claim 8 , wherein the organic substrate is a lubricant, and the compound(s) are present in an amount of about 0.03 to about 2.5 weight percent of said lubricant.
15. The composition according to claim 8 , wherein the composition further comprises one or more additional antioxidants.
16. The composition of claim 15 , wherein the additional antioxidant is a sterically hindered phenol.