Method of producing hydroxyalkylcarbamate-functional polyamides and uses thereof
A modified drilling fluid comprising a drilling fluid and the reaction product(s) of a polyalkylene polyamine, fatty acid, and alkylene carbonate, and methods of making and using the same.
1. A modified drilling fluid, comprising:
a drilling fluid; and
a hydroxyalkylcarbamate-functional polyamide composition produced by:
reacting a polyalkylene polyamine and a fatty acid to form an amidoamine intermediate product, wherein the molar ratio of the polyalkylene polyamine to fatty acid ranges from 1:1.5 to 1:2.5; and
reacting the amidoamine intermediate product and an alkylene carbonate represented by formula (I) below:
wherein R 2 —R 5 are independently selected from i) hydrogen, ii) an alkyl group, and iii) a moiety comprising a hydroxyl, halide, aldehyde, ether, ester, carboxylic acid, epoxide, or a combination thereof.
2. The method of claim 1 , wherein the polyalkylene polyamine is a polyethylene polyamine selected from the group consisting of diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, and combinations thereof.
3. The modified drilling fluid of claim 1 , wherein the fatty acid is represented by formula (III):
R 1 —C(O)OH (III) wherein R 1 is a saturated or unsaturated, branched or straight chain, substituted or unsubstituted hydrocarbyl group having from 6 to 24 carbon atoms.
4. The modified drilling fluid of claim 1 , wherein the fatty acid is derived from a fatty acid source selected from the group consisting of soybean oil, coconut oil, rapeseed oil, tall oil, and combinations thereof.
5. The modified drilling fluid of claim 1 , wherein the fatty acid is lauric acid, mystic acid, palmilitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, linoleic acid, linolenic acid, or a combination thereof.
6. The modified drilling fluid of claim 1 , wherein the alkylene carbonate is represented by formula (I), wherein R 2 , R 3 , and R 5 are each hydrogen, and R 4 is selected from the group consisting of hydrogen, CH 3 , C 2 H 5 , and CH 3 OH.
7. The modified drilling fluid of claim 1 , wherein the drilling fluid is a water-in-oil invert emulsion drilling mud.
8. A method of producing a modified drilling fluid, comprising:
producing a hydroxylalkylcarbamate-functional polyamide comprising:
reacting a polyalkylene polyamine and a fatty acid to form an amidoamine intermediate product, wherein the molar ratio of the polyalkylene polyamine to fatty acid ranges from 1:1.5 to 1:2.5; and
reacting the amidoamine intermediate product and an alkylene carbonate, wherein the alkylene carbonate is represented by formula (I) below:
wherein R 2 —R 5 are independently selected from i) hydrogen, ii) an alkyl group, and iii) a moiety comprising a hydroxyl, halide, aldehyde, ether, ester, carboxylic acid, epoxide, or combinations thereof; and
mixing the hydroxyalkylcarbamate-functional polyamide with a drilling fluid.
9. The method of claim 8 , wherein the polyalkylene polyamine is a polyethylene polyamine selected from the group consisting of diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA), and combinations thereof.
10. The method of claim 8 , wherein the fatty acid is represented by formula (III):
R 1 —C(O)OH (III)
wherein R 1 is a saturated or unsaturated, branched or straight chain, substituted or unsubstituted hydrocarbyl group having from 6 to 24 carbon atoms.
11. The method of claim 10 , wherein the fatty acid is derived from a fatty acid source selected from the group consisting of soybean oil, coconut oil, rapeseed oil, tall oil, and combinations thereof.
12. The method of claim 10 , wherein the fatty acid is lauric acid, myristic acid, palmilitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, linoleic acid, linolenic acid, or a combination thereof.
13. The method of claim 8 , wherein the alkylene carbonate is represented by formula (I), wherein R 2 , R 3 , and R 5 are each hydrogen, and R 4 is selected from the group consisting of hydrogen, CH 3 , C 2 H 5 , and CH 3 OH.
14. A method of producing a modified drilling fluid, comprising mixing:
a drilling fluid; and
a hydroxyalkylcarbamate-functional polyamide composition produced by:
reacting a polyalkylene polyamine and fatty acid to form an amidoamine intermediate product, wherein the molar ratio of the polyalkylene polyamine to fatty acid ranges from 1:1.5 to 1:2.5; and
reacting the amidoamine intermediate product and an alkylene carbonate represented by formula (I) below:
wherein R 2 — R 5 are independently selected from i) hydrogen, ii) an alkyl group, and iii) a moiety comprising a hydroxyl, halide, aldehyde, ether, ester, carboxylic acid, epoxide, or a combination thereof.
15. A modified drilling fluid, comprising:
a drilling fluid; and
a hydroxyalkylcarbamate-functional polyamide composition comprising at least one compound represented by formula (VII):
wherein R 2 —R 5 are independently selected from i) hydrogen, ii) an alkyl group, and iii) a moiety comprising a hydroxyl, halide, aldehyde, ether, ester, carboxylic acid, epoxide, or a combination thereof; and
wherein R 1 is a saturated or unsaturated, branched or straight chain, substituted or unsubstituted hydrocarbyl group having from 6 to 24 carbon atoms.
16. The method of claim 15 , wherein the alkylene carbonate is represented by formula (I), wherein R 2 , R 3 , and R 5 are each hydrogen, and R 4 is selected from the group consisting of hydrogen, CH 3 , C 2 H 5 , and CH 3 OH.
17. The modified drilling fluid of claim 15 , wherein the drilling fluid is a water-in-oil invert emulsion drilling mud.