Cyclic phosphate additives and their use in oleaginous compositions
AssigneeExxon Chemical Patents Inc.
InventorsJack Ryer, Antonio Gutierrez, Harold E. Deen
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Abstract
The present invention provides a novel cyclic phosphate such as 1,3-dioxa-2-phospha-6-thia-cyclooctane-2-(dodecylthiodi(ethyleneoxy)-2-oxi de, and its use as an anti-wear, anti-oxidant, and/or friction modifying agent for oleaginous compositions such as fuels, and lubricating oils particularly automatic transmission fluids. A new use of overbased metal phenates and/or sulfonates as friction stability promoters for conventional friction modifying agents is also provided.
Claims85
A cyclic phosphate represented by the structural formula:
- ##STR21## wherein R can represent alkyl, alkenyl, cycloalkyl, aralkyl, alkaryl;
- n is a number which can vary from 1 to about 3, R.sub.1 is alkylene, n' is a number which can vary from about 1 to about 12;
- X' which may be the same or different can independently represent --O--, --NH-- or --S--;
- R.sub.2 and R.sub.3 which may be the same or different can independently represent substituted or unsubstituted alkylene;
- n" can represent the number 0 or 1;
- and Y can represent --O--, --NH--, --S--, --S--S--, or --CH.sub.2 -- when n" is 1;
- said R.sub.2 and R.sub.3 being joined together and constituting part of a cyclic hetero ring structure when n" is 0.
An oil soluble reaction product of:
- (1) an organo phosphorus oxydichloride represented by formula:
- ##STR22## wherein R can represent alkyl, alkenyl, cycloalkyl, aralkyl, and alkaryl;
- n is a number which can vary from about 1 to about 12;
- and
- (2) a cyclizing agent represented by the formula:
- ##STR23## wherein X and X' which may be the same or different can independently represent --O--, --NH--, --S--;
- R2 and R3 which may be the same or different can independently represent substituted or unsubstituted alkylene;
- n" can represent the number 0 or 1;
- and Y can represent --O--, --NH--, --S--, --S--S--, or --CH.sub.2 -- when n" is 1;
- wherein said reactive components 1 and 2 are reacted at about a 1:1 molar ratio and under reaction conditions effective to produce said product, and liberated HCl is removed from the product produced thereby.
A lubricating oil composition adaptable for use as an automatic transmission fluid which comprises mineral oil and an amount of a cyclic phosphate effective to impart at least one of the properties of anti-wear, friction modification, and anti-oxidation, to said fluid, said cyclic phosphate being represented by the formula:
- ##STR24## wherein R represents alkyl, alkenyl, cycloalkyl, aralkyl, and alkaryl;
- n is a number which can vary from 1 to about 3, R.sub.1 is alkylene, n' is a number which can vary from about 1 to about 12;
- X and X' which may be the same or different can independently represent --O--, --NH-- or --S--;
- R.sub.2 and R.sub.3 which may be the same or different can independently represent substituted or unsubstituted alkylene;
- n" can represent the number 0 or 1;
- and Y can represent --O--, --NH--, --S--, --S--S--, or --CH.sub.2 -- when n" is 1;
- said R.sub.2 and R.sub.3 being joined together and constituting part of a cyclic hetero ring structure when n" is 0.
A lubricating oil composition adaptable for use as a power transmitting fluid which comprises a lubricating oil having dissolved therein at least one cyclic phosphate, at least one succinate ester or metal salt thereof, and at least one overbased friction stability promoter wherein:
- (1) said cyclic phosphate is represented by the structural formula:
- ##STR27## wherein R can represent alkyl, alkenyl, cycloalkyl, aralkyl, and alkaryl;
- n is a number which can vary from 1 to about 3, R.sub.1 is alkylene, n' is a number which can vary from about 1 to about 12;
- X and X' which may be the same or different can independently represent --O--, --NH-- or --S--;
- R.sub.2 and R.sub.3 which may be the same or different can independently represent substituted or unsubstituted alkylene;
- n" can represent the number 0 or 1 and Y can represent --O--, --NH--, --S--, --S--S--, or --CH.sub.2 -- when n" is 1;
- said R.sub.2 and R.sub.3 being joined together and constituting part of a cyclic hetero ring structure when n" is 0;
- (2) said succinate ester is the reaction product of:
- (A) an alcohol represented by the structural formula:
- ##STR28## wherein R.sub.4 and R.sub.5 each independently can represent hydrogen or C.sub.1 to C.sub.6 alkyl;
- (a), (b), (c), and (d) each independently represent a number which can vary from 1 to about 3;
- and Z represents a linking group selected from --S--, --S--S--, --O--, and NR.sub.6 wherein R.sub.6 can represent hydrogen, C.sub.1 to about C.sub.4 alkyl, or C.sub.1 to about C.sub.4 monohydroxy substituted alkyl;
- and
- (B) from about 1 to about 2 moles per mole of alcohol of an acid or anhydride represented by the respective structural formulas:
- ##STR29## wherein R.sub.7 is an aliphatic hydrocarbon group containing from about 12 to about 50 carbons;
- said metal of the metal salt when employed being selected from the group consisting of Mg, Ca, Ba, Zn, Ni, Cu, Mo and mixtures thereof;
- and
- (3) said overbased friction stability promoter is selected from the group consisting of (a) metal phenate derived from the reaction of a phenol or substituted phenol and an alkali or alkaline earth metal base;
- (b) sulfurized metal phenate;
- (c) metal sulfonate derived from the reaction of at least one aliphatic or aromatic sulfonic acid with an alkali or alkaline earth metal base;
- and (d) mixtures thereof.
A process for improving at least one of the properties of anti-wear, friction modification, and anti-oxidation of an oleaginous composition which comprises admixing at least an amount effective to improve at least one of said properties of a cyclic phosphate with an oleaginous material selected from the group consisting of fuels and lubricating oils, said cyclic phosphate being represented by the formula:
- ##STR30## wherein R can represent alkyl, alkenyl, cycloalkyl, aralkyl, and alkaryl;
- n is a number which can vary from 1 to about 3, R.sub.1 is alkylene, n' is a number which can vary from about 1 to about 12;
- X and X' which may be the same or different can independently represent --O--, --NH--, or --S--;
- R.sub.2 and R.sub.3 which may be the same or different can independently represent substituted or unsubstituted alkylene;
- n" can represent the number 0 or 1;
- and Y can represent --O--, --NH--, --S--, --S--S--, or --CH.sub.2 -- when n' is 1;
- and said R.sub.2 and R.sub.3 being joined together and constituting part of a cyclic hetero ring structure when n" is O.
A process for improving the friction stability of a lubricating oil composition which when adapted for use as an automatic transmission fluid contains a friction modifying effective amount of a friction modifier comprising a cyclic phosphate represented by the formula:
- ##STR31## wherein R represents alkyl, alkenyl, cycloalkyl, aralkyl, and alkaryl;
- n is a number which can vary from 1 to about 3, R.sub.1 is alkylene, n' is a number which can vary from about 1 to about 12;
- X and X' which may be the same or different independently represent --O--, --NH--, or --S--' R.sub.2 and R.sub.3 which may be the same or different independently represent substituted or unsubstituted alkylene;
- n" represents the number 0 or 1;
- and Y represents --O--, --NH--, --S--, --S--S-- or --CH.sub.2 when n' is 1;
- and said R.sub.2 and R.sub.3 being joined together and constituting part of a cyclic hetero ring structure when n" is o;
- which comprises adding to said lubricating oil composition a friction stability improving effective amount of at least one overbased friction stability promoter selected from the group consisting of (a) metal phenate, (b) sulfurized metal phenate, and (c) metal sulfonate, wherein said metal is selected from the group consisting of alkali metal, alkaline earth metal and mixtures thereof.
Dependencies are inferred from the claim text.