Oxazoline additives useful in oleaginous compositions
AssigneeExxon Research & Engineering Co.
InventorsJack Ryer, James Zielinski, Harold N. Miller, Stanley J. Brois
Life of this patent
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Abstract
Oil soluble oxazoline reaction products of hydrocarbon substituted dicarboxylic acid, ester, or anhydride, for example polyisobutenylsuccinic anhydride, with 2,2-disubstituted-2-amino-1-alkanols, such as tris-hydroxymethylaminomethane (THAM), are useful additives in oleaginous compositions, such as sludge dispersants for lubricating oil or gasoline.
Claims31
A lubricating oil composition comprising:
- a major amount of lubricating oil and 0.01 to 20 wt. % of bis-oxazoline of a molar proportion of a hydrocarbon-substituted C.sub.4 -C.sub.10 dicarboxylic acid material selected from the group consisting of dicarboxylic acid, ester and anhydrides thereof, having more than 50 carbon atoms in said hydrocarbon substituent;
- reacted with about two molar proportions of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbons of the formula:
- ##STR6## wherein X is alkyl or hydroxy alkyl, said alkyl groups having 1 to 3 carbon atoms, and at least one of said X is a hydroxy alkyl group of the structure --(CH.sub.2).sub.n OH where n is 1 to 3;
- at a temperature in the range of about 140.degree. to 240.degree. C for about 1/2 to 24 hours with the removal of about three molar proportions of water.
An additive concentrate comprising:
- a major amount of mineral lubricating oil in the range of 98 to 45 parts by weight, 2 to 45 parts by weight of bis-oxazoline of a molar proportion of a hydrocarbon-substituted C.sub.4 -C.sub.10 dicarboxylic acid material selected from the group consisting of dicarboxylic acid, ester and anhydrides thereof, having more than 50 carbon atoms in said hydrocarbon substituent;
- reacted with about two molar proportions of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbons of the formula:
- ##STR7## wherein X is alkyl or hydroxy alkyl, said alkyl groups having 1 to 3 carbon atoms, and at least one of said X is a hydroxy alkyl group of the structure --(CH.sub.2).sub.n OH where n is 1 to 3;
- at a temperature in the range of about 140.degree. to 240.degree. C for about 1/2 to 24 hours with the removal of about three molar proportions of water.
An oil-soluble, oxazoline reaction product obtained from heating together a molar equivalent of a hydrocarbon substituted C.sub.4 -C.sub.10 dicarboxylic acid material having more than 50 carbon atoms per dicarboxylic acid group, and two molar equivalents of a 2,2-disubstituted-2-amino-1-alkanol having the formula ##STR8## wherein X is alkyl or hydroxy alkyl, said alkyl groups having 1 to 3 carbon atoms, and at least one of said X is a hydroxy alkyl group of the structure --(CH.sub.2).sub.n OH where n is 1 to 3 at a temperature of from 140.degree.-240.degree. C. until cessation of water evolution indicating completion of the oxazoline reaction.
A bisoxazoline reaction product prepared by the reaction of a molar proportion of a hydrocarbon substituted C.sub.4 -C.sub.10 dicarboxylic acid material having more than 50 carbon atoms per dicarboxylic acid group and two molar proportions of a 2,2-disubstituted-2-amino-1-alkanol having the formula ##STR9## wherein X is alkyl or hydroxy alkyl, said alkyl groups having 1 to 3 carbon atoms, and at least one of said X is a hydroxy alkyl group of the structure --(CH.sub.2).sub.n OH where n is 1 to 3 at a temperature of from 140.degree.-240.degree. C. until cessation of water evolution indicating completion of the oxazoline reaction.
A bis-oxazoline of the general formula ##STR10## where X is an alkyl or hydroxy alkyl group said alkyl groups having 1 to 3 carbon atoms with at least one of the X substituents on each ring being a hydroxy alkyl group of the structure --(CH.sub.2).sub.n OH wherein n is 1 to 3 and R is a substantially saturated hydrocarbyl group containing at least 50 carbon atoms and m is from 0 to 6.
A process of preparing a bis-oxazoline comprising reacting a molar proportion of a substantially saturated hydrocarbyl-substituted C.sub.4 -C.sub.10 dicarboxylic acid or anhydride or ester thereof having at least 50 carbon atoms in said hydrocarbyl group with 2 molar proportions of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbons of the formula ##STR11## wherein X is alkyl or hydroxyalkyl, said alkyl groups having 1 to 3 carbon atoms, and at least one of said X is a hydroxy alkyl group of the structure --(CH.sub.2).sub.n OH where n is 1 to 3, at a temperature in the range of 140.degree. to 240.degree. C. for 1/2 to 24 hours with the removal of three molar proportions of water.
Dependencies are inferred from the claim text.