Ketone diarylamine condensates
View Patent ↗Disclosed herein is a composition comprising: A) a lubricant; and B) a mixture of antioxidants, wherein said mixture is prepared by the partial condensation of an alkylated diphenylamine with an aldehyde or ketone in the presence of an acidic catalyst to yield at least one acridan of the general formula: wherein: R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, C 3 to C 32 alkyl, and C 3 to C 32 alkenyl, provided that at least one of R 1 , R 2 , R 3 , and R 4 is not hydrogen, and R 5 and R 6 are independently selected from the group consisting of C 1 to C 20 hydrocarbyl and hydrogen; wherein, at the termination of said condensation, residual alkylated diphenylamine is not separated from the acridan product.
1. A composition comprising:
A) a lubricant; and
B) a mixture of antioxidants, wherein said mixture is prepared by the partial condensation of an alkylated diphenylamine comprising a tri-nonylated diphenylamine with an aldehyde or ketone in the presence of an acidic catalyst to yield at least one acridan of the general formula:
along with residual alkylated diphenylamine remaining after said partial condensation;
wherein:
R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen and nonyl, provided that at least three of R 1 , R 2 , R 3 , and R 4 are not hydrogen, and R 4 , and R 5 are independently selected from the group consisting of C 1 to C 20 hydrocarbyl and hydrogen; wherein, at the termination of said condensation, residual alkylated diphenylamine is not separated from the acridan product and remains in said mixture with said antioxidants.
2. The composition of claim 1 wherein the alkylated diphenylamine is condensed with a ketone.
3. The composition of claim 2 wherein the ketone is acetone.
4. The composition of claim 1 wherein the composition further comprises at least one antioxidant in addition to that provided by the mixture of acridan and residual alkylated diphenylamine.
5. The composition of claim 4 wherein the additional antioxidant is selected from the group consisting of amine antioxidants, hindered phenol antioxidants, and mixtures thereof.
6. The composition of claim 5 wherein the hindered phenol antioxidant is selected from the group consisting of 2,4-dimethyl-6-octyl-phenol; 2,6-di-t-butyl-4-methyl phenol; 2,6-di-t-butyl-4-ethyl phenol; 2,6-di-t-butyl-4-n-butyl phenol; 2,2′-methylenebis(4-methyl-6-t-butyl phenol); 2,2′-methylenebis(4-ethyl-6-t-butyl-phenol); 2,4-dimethyl-6-t-butyl phenol; 4-hydroxymethyl-2,6-di-t-butyl phenol; n-octadecyl-beta(3,5-di-t-butyl-4-hydroxyphenyl)propionate; 2,6-dioctadecyl-4-methyl phenol; 2,4,6-trimethyl phenol; 2,4,6-triisopropyl phenol; 2,4,6-tri-t-butyl phenol; 2-t-butyl-4,6-dimethyl phenol; 2,6-methyl-4didodecyl phenol; tris(3,5-di-t-butyl-4-hydroxy isocyanurate; tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane; 3,5-di-t-butyl-4-hydroxy hydrocinnamate; octadecyl-3,5-di-t-butyl-4-hydroxy hydrocinnamate; tetrakis{methylene(3,5-di-t-butyl-4-hydroxyhydrocinnamate)}methane; 1,2-bis(3,5-di-t-butyl-4-hydroxyhydrocinnamoyl)hydrazine; 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl)-s-triazine-2,4,6(1H,3H,5H)trione; 2,2′-oxamido bis-{ethyl-3-(3,5-di-t-butyl-4-hydroxyphen-yl)}propionate; 1,3,5-tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl)-s-triaz-ine-2,4,6-(1H,3H,5H)trione; 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hy-droxybenzyl)benzene; 3,5-di-t-butyl-4-hydroxyhydrocinnamic acid triester with 1,3,5-tris(2-hydroxyethyl)-5-triazine-2,4,6(1H,3H,5H)-trione; bis(3,3-bis(4-hydroxy-3-t-butylphenyl)butanoic acid)glycolester; tetrakis{methylene (3,5-di-t-butyl-4-hydroxyhydrocinnamate)}methane; 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene; and 3,5-di-t-butyl-4-hydroxy-hydrocinnamic acid C 7 -C 9 branched alkyl ester.
7. A method for reducing the susceptibility of a lubricant to oxidation comprising adding to said lubricant a mixture of antioxidants, wherein said mixture is prepared by the partial condensation of an alkylated diphenylamine with an aldehyde or ketone in the presence of an acidic catalyst to yield at least one acridan of the general formula:
along with residual alkylated diphenylamine remaining after said partial condensation;
wherein:
R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen and nonyl, provided that at least three of R 1 , R 2 , R 3 , and R 4 are not hydrogen, and R 4 , and R 5 are independently selected from the group consisting of C 1 to C 20 hydrocarbyl and hydrogen; wherein, at the termination of said condensation, residual alkylated diphenylamine is not separated from the acridan product and remains in said mixture with said antioxidants.
8. The method of claim 7 wherein the alkylated diphenylamine comprises mono-, di-, and tri-nonylated diphenylamine.
9. The method of claim 7 wherein the alkylated diphenylamine is condensed with a ketone.
10. The method of claim 9 wherein the ketone is acetone.
11. The method of claim 8 wherein the alkylated diphenylamine is condensed with a ketone.
12. The method of claim 11 wherein the ketone is acetone.
13. The method of claim 7 wherein the composition further comprises at least one antioxidant in addition to that provided by the mixture.
14. The method of claim 13 wherein the additional antioxidant is selected from the group consisting of amine antioxidants, hindered phenol antioxidants, and mixtures thereof.
15. The method of claim 14 wherein the hindered phenol antioxidant is selected from the group consisting of 2,4-dimethyl-6-octyl-phenol; 2,6-di-t-butyl-4-methyl phenol; 2,6-di-t-butyl-4-ethyl phenol; 2,6-di-t-butyl-4-n-butyl phenol; 2,2′-methylenebis(4-methyl-6-t-butyl phenol); 2,2′-methylenebis(4-ethyl-6-t-butyl-phenol); 2,4-dimethyl-6-t-butyl phenol; 4-hydroxymethyl-2,6-di-t-butyl phenol; n-octadecyl-beta(3,5-di-t-butyl-4-hydroxyphenyl)propionate; 2,6-dioctadecyl-4-methyl phenol; 2,4,6-trimethyl phenol; 2,4,6-triisopropyl phenol; 2,4,6-tri-t-butyl phenol; 2-t-butyl-4,6-dimethyl phenol; 2,6-methyl-4-didodecyl phenol; tris(3,5-di-t-butyl-4-hydroxy isocyanurate; tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane; 3,5-di-t-butyl-4-hydroxy hydrocinnamate; octadecyl-3,5-di-t-butyl-4-hydroxy hydrocinnamate; tetrakis{methylene(3,5-di-t-butyl-4-hydroxyhydrocinnamate)}methane; 1,2-bis(3,5-di-t-butyl-4-hydroxyhydrocinnamoyl)hydrazine; 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl)-s-triazine-2,4,6(1H,3H,5H)trione; 2,2′-oxamido bis-{ethyl-3-(3,5-di-t-butyl-4-hydroxyphen-yl)}propionate; 1,3,5-tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl)-s-triaz-ine-2,4,6-(1H,3H,5H)trione; 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hy-droxybenzyl)benzene; 3,5-di-t-butyl-4-hydroxyhydrocinnamic acid triester with 1,3,5-tris(2-hydroxyethyl)-5-triazine-2,4,6(1H,3H,5H)-trione; bis(3,3-bis(4-hydroxy-3-t-butylphenyl)butanoic acid)glycolester; tetrakis{methylene(3,5-di-t-butyl-4-hydroxyhydrocinnamate)}methane; 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene; and 3,5-di-t-butyl-4-hydroxy-hydrocinnamic acid C 7 -C 9 branched alkyl ester.
16. A composition according to claim 1 comprising:
A) a lubricant; and
B) a mixture of antioxidants, wherein said mixture is prepared by the partial condensation of an alkylated diphenylamine comprising mono-, di-, and tri-nonylated diphenylamine with an aldehyde or ketone in the presence of an acidic catalyst to yield at least one acridan of the general formula:
along with residual alkylated diphenylamine remaining after said partial condensation;
wherein:
R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen and nonyl, provided that at least three of is R 1 , R 2 , R 3 , and R 4 not hydrogen, and R 4 , and R 5 are independently selected from the group consisting of C 1 to C 20 hydrocarbyl and hydrogen; wherein, at the termination of said condensation, residual alkylated diphenylamine is not separated from the acridan product and remains in said mixture with said antioxidants.