Hydroxy-group containing acylated nitrogen compounds useful as additives for lubricating oil and fuel compositions
AssigneeThe Lubrizol Corporation
InventorsPaul E. Adams, Mark R. Baker, Jeffry G. Dietz
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Abstract
Compositions comprising hydroxyl group containing acylated nitrogen compounds, a process for reacting certain carboxylic reactants with olefinic compounds then reacting the product prepared thereby with ammonia, a hydrazine or an amine, products prepared thereby and lubricating oil and fuel compositions.
Claims85
A composition comprising a compound of the formula ##STR21## wherein each of R.sup.1 and R.sup.2 is H or a hydrocarbon based group, R.sup.3 is H or hydrocarbyl;
- R.sup.4 is a divalent hydrocarbylene group;
- n=0 or 1;
- y is an integer ranging from 1 to about 200;
- A is a hydrocarbyl group or a hydroxy-substituted hydrocarbyl group selected from groups of the formula ##STR22## wherein z=0 or 1;
- wherein X is a divalent hydrocarbyl group selected from the group consisting of ##STR23## when z=0, and ##STR24## when z=1:
- wherein each of R.sup.5, R.sup.6, R.sup.7 and R.sup.8 is independently H or a hydrocarbon based group;
- and each of R.sup.9 and R.sup.10 is independently H, alkoxyhydrocarbyl, hydroxyhydrocarbyl, hydrocarbyl, aminohydrocarbyl, N-alkoxyalkyl- or hydroxyalkyl-substituted aminohydrocarbyl, or a group of the formula .paren open-st.Y.paren close-st..sub.a R.sup.11 --B, wherein each Y is a group of the formula ##STR25## or
- R.sup.11 --O--,
- each R.sup.11 is a divalent hydrocarbyl group, R.sup.12 is as defined above for R.sup.9 and R.sup.10, and B is H, hydrocarbyl, amino, hydroxyhydrocarbyl, an amide group, an amide-containing group, an acylamino group, an imide group, or an imide-containing group, and a is 0 or a number ranging from 1 to about 100, provided that no more than three R.sup.9, R.sup.10, and R.sup.12 contain amide groups, imide-containing groups, acylamino groups or amide-containing groups;
- or
- R.sup.9 and R.sup.10 taken together with the adjacent N constitute a nitrogen-containing heterocyclic group, optionally further containing one or more additional heteroatoms selected from the group consisting of N, O and S;
- or
- one of R.sup.9 and R.sup.10 taken together with the adjacent N constitute a N--N group.
A process comprising first reacting, optionally in the presence of an acidic catalyst selected from the group consisting of organic sulfonic acids, heteropolyacids, Lewis acids, and mineral acids,
- (A) at least one olefinic compound containing at least one group of the formula ##STR32## and (B) at least one carboxylic reactant selected from the group consisting of compounds of the formula
- R.sup.3 C(O)(R.sup.4).sub.a C(O)OR.sup.5 (IV)
- and compounds of the formula ##STR33## wherein each of R.sup.3, R.sup.5 and R.sup.9 is independently H or a hydrocarbyl group, R.sup.4 is a divalent hydrocarbylene group, and n is 0 or 1;
- wherein (A) and (B) are reacted in amounts ranging from 0.6 moles (B) per mole of (A) to 1.5 moles (B) per equivalent of (A);
- then reacting the product formed thereby with from about 0.5 equivalents up to about 2 moles, per mole of (B) of at least one of
- (C) ammonia or a hydrazine or an amine characterized by the presence within its structure of at least one H--N group.
Dependencies are inferred from the claim text.