Hydroxyalkyldithiocarbamate borate esters
View Patent ↗A novel hydroxyalkyldithiocarbamate borate ester compound is presented according to the formula: where R=alkyl C 1 to C 25 ; R′=H or CO 2 R; R″=(CH 2 ) m OH where m=1 to 8, or alkyl C 1 to C 25 ; n=1 to 8. The borate ester compound is prepared by reacting boric acid with a novel hydroxyalkyldithiocarbamate ester compound according to the formula, and optionally with an alcohol: where R, R′, R″ and n are as above. The hydroxyalkyldithiocarbamate ester is prepared by reacting a hydroxyalkylamine with CS 2 , and an acrylate or maleate compound. A lubricating composition is based on a major amount of lubricating oil and a minor amount of the hydroxyalkyldithiocarbamate borate ester.
1. A method for preparing a hydroxyalkyldithiocarbamate borate ester, comprising the step of reacting boric acid with a hydroxyalkyldithiocarbamate ester.
2. The method according to claim 1 , further comprising the step of preparing the hydroxyalkyldithiocarbamate ester by reacting a hydroxyalkylamine with CS 2 , and an acrylate or maleate compound.
3. The method according to claim 2 wherein the alkyl chain length between the hydroxyl and amine functionalities in the hydroxyalkylamine is between 1 and 8 carbon atoms.
4. The method according to claim 2 wherein the hydroxyalkylamine is an N-alkyl ethanolamine with the alkyl group containing between 1 and 25 carbon atoms.
5. The method according to claim 2 wherein the hydroxyalkylamine is N-butylethanolamine or N-ethylcthanolamine.
6. The method according to claim 2 wherein the hydroxyalkylamine is diethanolamine.
7. The method according to claim 2 wherein the acrylate or maleate used contains alkyl group(s) between 1 and 25 carbon atoms.
8. The method according to claim 2 wherein the acrylate or maleate is chosen from the group consisting of dodecylacrylate, di-2-ethylhexylmaleate and dibutylmaleate.
9. The method according to claim 1 , wherein the resulting borate ester comprises about 0.5 to 5% by weight boron and about 0.5 to 30% by weight sulfur.
10. The method according to claim 1 , wherein the hydroxyalkyldithiocarbamate ester is chosen according to the formula, wherein R=alkyl C 1 to C 25 ; R′=H or CO 2 R; R″=(CH 2 ) m OH where m=1 to 8, or alkyl C 1 to C 25 ; n=1 to 8:
11. The method according to claim 1 , wherein the reaction of a hydroxyalkyldithiocarbamate and boric acid further includes reacting with an alcohol.
12. The method according to claim 11 , wherein the alcohol contains between 1 and 25 carbon atoms.
13. A composition of matter being a hydroxyalkyldithiocarbamate borate ester according to the formula:
wherein R=alkyl C 1 to C 25 ; R′=H or CO 2 R; R″=(CH 2 ) m OH where m=1 to 8, or alkyl C 1 to C 25 ; n=1 to 8.
14. The composition of matter according to claim 13 , comprising about 0.5 to 5% by weight boron and about 0.5 to 30% by weight sulfur.
15. A composition of matter being the reaction product of boric acid with a hydroxyalkyldithiocarbamate ester.
16. The composition according to claim 15 , comprising the reaction product of boric acid with a hydroxyalkyldithiocarbamate ester, and an alcohol.
17. The composition according to claim 15 , wherein the reaction product comprises about 0.5 to 5% by weight boron and about 0.5 to 30% by weight sulfur.
18. The composition according to claim 15 , wherein the hydroxyalkyldithiocarbamate ester is chosen according to the formula, wherein R=alkyl C 1 to C 25 ; R′=H or CO 2 R; R″=(CH 2 ) m OH where m=1 to 8, or alkyl C 1 to C 25 ; n=1 to 8:
19. A lubricant composition comprising a major amount of lubricating oil and an additive being a hydroxyalkyldithiocarbamate borate ester of claim 13 at between 0.01 to 10 mass %.
20. The lubricant composition of claim 19 , wherein the additive is present at between 0.1 and 5 mass %.
21. The lubricant composition of claim 20 , wherein the additive is present at between 1 and 3 mass %.
22. The lubricant composition of claim 19 , wherein the additive is a mixture of alkoxy and hydroxyalkyldithiocarbamate borate ester.