Novel diamide and lubricants containing same

Abstract

Carboxylic acid terminated diamides and alkali metal, ammonium or amine salts thereof are provided which are derived from the reaction of organic polycarboxylic acids and polyoxyalkylene diamines. The diamides have lubricating properties and are especially useful in aqueous metal working fluids.

What is claimed is: 
     
       1. A carboxylic acid group terminated polyoxyalkylene diamide and the alkali metal, ammonium or organic amine salt thereof having the following formula ##STR3## wherein R is the divalent polyoxyalkylene chain radical residue of an amine terminated polyoxyalkylene diamine absent the terminal amine groups, R 1  and R 2  are the same or different and are selected from the group consisting of aliphatic, aromatic, cycloaliphatic, arylaliphatic, alkyl aromatic, thiodialiphatic.[.,.]. .Iadd.or .Iaddend.halogen substituted aliphatic .[.or halogen substituted aromatic.]. radicals and having a free valence of a+n+1 and b+m+1 respectively,   Z is an organic amine cation, ammonium ion or alkali metal ion,   a is 0 to 3,   b is 0 to 3,   n is 0 to 3,   m is 0 to 3,   a+n is 0 to 3,   b+m is 0 to 3 and   a+b+m+n is 1 to 6.   
     
     
       2. A carboxylic acid group terminated polyoxyalkylene diamide and alkali metal, ammonium or organic amine salt thereof according to claim 1 wherein R 1  and R 2  are hydrocarbon radicals. 
     
     
       3. A carboxylic acid group terminated polyoxyalkylene diamide and alkali metal, ammonium or organic amine salt thereof according to claim 1 wherein R 1  and R 2  are selected from the group consisting of aliphatic, aromatic, cycloaliphatic, thiodialiphatic.[.,.]. .Iadd.or .Iaddend.halogen substituted aliphatic .[.or halogen substituted aromatic.].  radicals. 
     
     
       4. A carboxylic acid group terminated polyoxyalkylene diamide and alkali metal, ammonium or organic amine salt thereof according to claim 3 wherein R 1  and R 2  are selected from the group consisting of C 2  to C 18  saturated or unsaturated aliphatic, C 6  aromatic, C 6  cycloaliphatic and thio di (C 2  to C 3  aliphatic) hydrocarbon radicals. 
     
     
       5. A carboxylic acid group terminated polyoxyalkylene diamide and alkali metal, ammonium or organic amine salt thereof according to claim 1, 2, 3 or 4 wherein R is a divalent poly(oxy C 2  C 4  alkylene) homopolymer or copolymer chain radical residue. 
     
     
       6. A carboxylic acid group terminated polyoxyalkylene diamide and alkali metal, ammonium or organic amine salt thereof according to claim 5 wherein R is a divalent poly(oxy C 2  to C 4  alkylene) homopolymer chain radical residue. 
     
     
       7. A carboxylic acid group terminated polyoxyalkylene diamide and alkali metal, ammonium or organic amine salt thereof according to claim 5 wherein R is a divalent poly(oxy C 2  to C 4  alkylene) copolymer chain radical residue. 
     
     
       8. The alkali metal, ammonium or organic amine salt of the carboxylic acid group terminated polyoxyalkylene diamide according to claim 5. 
     
     
       9. The organic amine salt of the carboxylic acid group terminated polyoxyalkylene diamide according to claim 5. 
     
     
       10. The salt according to claim 9 wherein the organic amine is a monoalkanol amine, dialkanol amine or trialkanol amine. 
     
     
       11. The salt according to claim 10 wherein the organic amine is a trialkanol amine. 
     
     
       12. The salt according to claim 11 wherein the trialkanol amine is a tri(C 1  to C 3  alkanol) amine. 
     
     
       13. The carboxylic acid group terminated polyoxyalkylene diamide and the alkali metal, ammonium or organic amine salt thereof according to claim 5 wherein a+n is 1 or 2 and b+m is 1 or 2. 
     
     
       14. A metal working composition comprising (a) a substance selected from the group consisting of natural oil, synthetic oil and water and (b) from 0.01% to 99% by weight based on the total weight of the composition of a carboxylic acid group terminated polyoxyalkylene diamide or the alkali metal, ammonium or organic amine salt thereof according to claim 1. 
     
     
       15. A metal working composition comprising (a) a substance selected from the group consisting of natural oil, synthetic oil and water and (b) from 0.01% to 99% by weight based on the total weight of the composition of a carboxylic acid group terminated polyoxyalkylene diamide or the alkali metal, ammonium or organic amine salt in accordance with claim 5. 
     
     
       16. A metal working composition comprising (a) a substance selected from the group consisting of natural oil, synthetic oil and water and (b) from 0.01% to 99% by weight based on the total weight of the composition of a carboxylic acid terminated polyoxyalkylene diamide or the alkali metal, ammonium or organic amine salt thereof according to claim 6. 
     
     
       17. A metal working composition comprising (a) a substance selected from the group consisting of natural oil, .[.synthetic oil,.]. synthetic oil and water and (b) from 0.01% to 99% by weight based on the total weight of the composition of a carboxylic acid group terminated polyoxyalkylene diamide or the alkali metal, ammonium or organic amine salt thereof according to claim 7. 
     
     
       18. A metal working composition comprising (a) a substance selected from the group consisting of natural oil, synthetic oil and water and (b) from 0.01% to 99% by weight based on the total weight of the composition of a salt according to claim 10. 
     
     
       19. A metal working composition comprising (a) a substance selected from the group consisting of natural oil, synthetic oil and water and (b) from 0.01% to 99% by weight based on the total weight of the composition of a salt according to claim 12. 
     
     
       20. A metal working composition comprising (a) a substance selected from the group consisting of natural oil, synthetic oil and water and (b) from 0.01% to 99% by weight based on the total weight of the composition of a carboxylic acid group terminated polyoxyalkylene diamide or the alkali metal, ammonium or organic amine salt thereof according to claim 13. 
     
     
       21. A metal working composition according to claim 15 wherein (a) is water. 
     
     
       22. A metal working composition according to claim 18 wherein (a) is water. 
     
     
       23. A metal working composition according to claim 19 wherein (a) is water. 
     
     
       24. A metal working composition according to claim 20 wherein (a) is water. 
     
     
       25. A metal working composition according to claim 21 wherein (b) is present in an amount of from 0.01% to 25% by weight based on the total weight of the composition.