Lubricating oil and fuel compositions
View Patent ↗Disclosed herein are reaction products of an acidic organic compound, a boron compound, and an alkoxylated amine and/or alkoxylated amide. Also disclosed are lubricating oil compositions and fuel compositions containing the reaction products.
1. A reaction product of an acidic organic compound, a boron compound, and an amine, wherein the reaction product is a metal free detergent and wherein the amine is selected from the group consisting of
(a) an alkoxylated amine represented by general formula:
wherein R 18 is hydrogen or a substituted or unsubstituted hydrocarbyl having from 1 to about 30 carbon atoms; R 19 in each of the x (R 19 O) groups is independently a straight or branched C 2 -C 4 alkylene; R 20 is a bond or a substituted or unsubstituted hydrocarbylene having from 2 to about 6 carbon atoms; R 21 and R 22 are each independently hydrogen, substituted or unsubstituted hydrocarbyl having from 1 to about 30 carbon atoms, —(R 23 ) n —(R 19 O) y R 24 , or R 21 and R 22 together with the nitrogen atom to which they are bonded are joined together to form a heterocyclic group; R 23 is substituted or unsubstituted hydrocarbylene containing from 1 to about 6 carbon atoms, R 24 is hydrogen or a linear or branched alkyl group having 1 to about 4 carbon atoms, n is 0 or 1, and x and y are independently an average number from 1 to about 60;
(b) an alkoxylated amine represented by general formula:
wherein R 25 is a substituted or unsubstituted hydrocarbyl having from 1 to about 30 carbon atoms and preferably from about 8 to about 30 carbon atoms; R 26 in each of the x (R 26 O) groups is independently a straight or branched C 2 -C 4 alkylene; R 27 is hydrogen or a straight or branched alkyl group having from 1 to about 6 carbon atoms; R 28 is a substituted or unsubstituted hydrocarbyl having from 1 to about 30 carbon atoms, and x is an average number from 1 to about 60;
(c) a dialkoxylated amine represented by general formula:
wherein R 29 is a linear or branched alkyl, linear or branched alkenyl, linear or branched alkynyl, aryl, or aralkyl group having from about 6 to about 30 carbon atoms, R 30 in each of the x (R 30 O) and the y (R 30 O) groups is independently a straight or branched C 2 -C 4 alkylene, R 31 is independently hydrogen, or a linear or branched alkyl group having from 1 to about 4 carbon atoms and x and y are independently an average number from 1 to about 40; and mixtures thereof, wherein the acidic organic compound is selected from the group consisting of:
(A) alkyl substituted salicylic acids,
(B) di-substituted salicylic acids,
(C) oil soluble hydroxy carboxylic acids,
(D) salicylic acid calixarenes,
(E) sulfur-containing calixarenes,
(F) acids of the formula:
wherein R 11 is hydrocarbon or halogen, R 12 is hydrocarbon, and Ar is substituted or unsubstituted aryl,
(G) acids of the formula:
wherein X and X′ are independently selected from the group consisting of hydrogen, hydrocarbyl, and halogen, R 13 is polymethylene or branched or unbranched alkylene, x is 0 or 1, and R 14 is hydrogen or hydrocarbyl,
(H) acids of the formula:
wherein
R 15 and R 16 are independently selected from the group consisting of hydrogen, hydrocarbyl groups, tertiary alkyl groups, and tertiary aralkyl groups, provided that both R 15 and R 16 are not hydrogen,
each R 17 are independently selected from the group consisting of hydrogen, hydrocarbyl groups, aralkyl groups, and cycloalkyl groups, and
x is from 0 to 24, inclusive; and
(I) salts of the foregoing acids.
2. The reaction product of claim 1 , wherein the acidic organic compound is selected from the group consisting of:
(A) alkyl substituted salicylic acids, and
(B) di-substituted salicylic acids.
3. The reaction product of claim 1 , wherein the boron compound is selected from the group consisting of boric acid, trialkyl borates, alkyl boric acids, dialkyl boric acids, boric oxide, boric acid complex, cycloalkyl boric acids, aryl boric acids, dicycloalkyl boric acids, diaryl boric acids, and substitution products of the foregoing with alkoxy groups, alkyl groups, alkyl groups, and combinations thereof.
4. The reaction product of claim 1 , wherein the amine is selected from the group consisting of saturated or unsaturated monoalkoxylated alkylamines, saturated or unsaturated monoalkoxylated arylamines, saturated or unsaturated polyalkoxylated alkylamines, saturated or unsaturated polyalkoxylated arylamines and mixtures thereof.
5. The reaction product of claim 1 , wherein the alkoxylated amine comprises an alkoxylated derivative of a reaction product of an alkanolamine with a C 4 -C 75 fatty acid ester.
6. The reaction product of claim 1 , wherein the amine comprises an ethoxylated fatty acid amine.
7. A reaction product of an acidic organic compound, a boron compound, and an amide selected from the group consisting of monoalkoxylated amides, polyalkoxylated amides and mixtures thereof, wherein the reaction product is a metal free detergent.
8. The reaction product of claim 7 , wherein the acidic organic compound is selected from the group consisting of:
(A) alkyl substituted salicylic acids,
(B) di-substituted salicylic acids,
(C) oil soluble hydroxy carboxylic acids,
(D) salicylic acid calixarenes,
(E) sulfur-containing calixarenes,
(F) acids of the formula:
wherein R 11 is hydrocarbon or halogen, R 12 is hydrocarbon, and Ar is substituted or unsubstituted aryl,
(G) acids of the formula:
wherein X and X′ are independently selected from the group consisting of hydrogen, hydrocarbyl, and halogen, R 13 is polymethylene or branched or unbranched alkylene, x is 0 or 1, and R 14 is hydrogen or hydrocarbyl,
(H) acids of the formula:
wherein
R 15 and R 16 are independently selected from the group consisting of hydrogen, hydrocarbyl groups, tertiary alkyl groups, and tertiary aralkyl groups, provided that both R 15 and R 16 are not hydrogen,
each R 17 are independently selected from the group consisting of hydrogen, hydrocarbyl groups, aralkyl groups, and cycloalkyl groups, and
x is from 0 to 24, inclusive; and
(I) salts of the foregoing acids.
9. The reaction product of claim 7 , wherein the boron compound is selected from the group consisting of boric acid, trialkyl borates, alkyl boric acids, dialkyl boric acids, boric oxide, boric acid complex, cycloalkyl boric acids, aryl boric acids, dicycloalkyl boric acids, diaryl boric acids, and substitution products of the foregoing with alkoxy groups, alkyl groups, alkyl groups, and combinations thereof.
10. The reaction product of claim 7 , wherein the alkoxylated amide comprises an ethoxylated fatty acid amide.