Wellbore Servicing Fluids and Methods of Making and Using Same

1 . A method of servicing a wellbore comprising placing an invert emulsion drilling fluid having an oleaginous continuous phase, a non-oleaginous discontinuous phase, and a fluid loss additive into a wellbore wherein the fluid loss additive comprises a quaternary ammonium compound containing at least one ester linkage.

2 . The method of claim 1 wherein the drilling fluid is substantially free from organophilic clay.

3 . The method of claim 1 wherein the quaternary ammonium compound comprising at least one ester linkage is characterized by the general formula:

wherein R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of hydrogen; hydroxyl groups; saturated or unsaturated alkyl groups; aromatic groups; cyclic alkyl groups; alkyl-aryl groups; heterocyclic groups; and sugar groups containing from about 1 to about 36 carbon atoms;

wherein at least two of the R groups each comprise more than 12 carbon atoms;

wherein A − is selected from the group consisting of halide ions, sulfate ions, sulfonate ions, nitrate ions, carboxylate ions, hydroxyl ions and phosphate ions; and

wherein x 1 , x 2 , x 3 , and x 4 each have a value from about 0 to about 1 and n 1 , n 2 , n 3 , and n 4 each have a value of from about 0 to about 18.

4 . The method of claim 3 wherein when any, but not more than two of, n 1 , n 2 , n 3 , or n 4 is zero at any one time, then a corresponding x 1 , x 2 , x 3 , or x 4 is zero and wherein when any of R 1 , R 2 , R 3 or R 4 is a hydrogen and a corresponding x 1 -n 1 , x 2 -n 2 , x 3 -n 3 , or x 4 -n 4 pair is zero the nitrogen is directly bonded to hydrogen.

5 . The method of claim 3 wherein any, but not all of x 1 , x 2 , x 3 , or x 4 is zero at the same time and a corresponding R 1 , R 2 , R 3 or R 4 each independently bonds directly to the carbon of a corresponding (CH 2 ) n .

6 . The method of claim 1 wherein the quaternary ammonium compound comprising at least one ester linkage is characterized by the general formula:

wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen; hydroxyl groups; saturated or unsaturated alkyl groups; cyclic alkyl groups; aromatic groups; alkyl-aryl groups; heterocyclic groups; and sugar groups containing from about 1 to about 36 carbon atoms;

wherein at least two of the R groups each comprise more than 12 carbon atoms;

wherein A− is selected from the group consisting of halide ions sulfate ions, sulfonate ions, nitrate ions, carboxylate ions, hydroxyl ions and phosphate ions;

wherein each F is independently selected from the group consisting of an ester group, an ether group, an amide group, an imide group, an amine group, a ketonic group, heterocyclic group, a cyclic alkyl group, an unsaturated alkyl group, an aryl group, or a sugar group;

and wherein x 1 , x 2 , x 3 , x 4 , x 5 , and x 6 each have a value from about 0 to about 1; and n 1 , n 2 , n 3 , n 4 , n 5 , n 6 , or m each have a value of from about 0 to about 18.

7 . The method of claim 6 wherein when any, but not more than four of, n 1 , n 2 , n 3 , n 4 , n 5 , or n 6 is zero at any one time then a corresponding x 1 , x 2 , x 3 , x 4 , x 5 , or x 6 is zero and wherein when any of R 1 , R 2 , R 3 , R 4 , R 5 or R 6 is a hydrogen and a corresponding x 1 -n 1 , x 2 -n 2 , x 3 -n 3 , x 4 -n 4 , x 5 -n 5 , or x 6 -n 6 pair is zero the nitrogen is directly bonded to hydrogen.

8 . The method of claim 6 wherein any, but not all of, x 1 , x 2 , x 3 , x 4 , x 5 , or x 6 is zero at the same time and a corresponding R 1 , R 2 , R 3 , R 4 , or R 5 independently bonds directly to the carbon of a corresponding (CH 2 ) n .

9 . The method of claim 1 wherein the quaternary ammonium compound comprising at least one ester linkage is characterized by the general formula:

where R 1 , R 2 , R 3 R 4 , R 5 , R 6 , R 7 and R 8 are each independently selected from the group consisting of hydrogen; hydroxyl groups; saturated or unsaturated alkyl groups; cyclic alkyl groups; aromatic groups; alkyl-aryl groups; heterocyclic groups; and sugar groups containing from about 1 to about 36 carbon atoms;

wherein at least three of the R groups each comprise more than 12 carbon atoms;

wherein A− is selected from the group consisting of halide ions sulfate ions, sulfonate ions, nitrate ions, carboxylate ions, hydroxyl ions and phosphate ions;

each F is independently selected from the group consisting of an ester group, an ether group, an amide group, an imide group, an amine group, a ketonic group, heterocyclic group, a cyclic alkyl group, an unsaturated alkyl group, an aryl group, and a sugar group;

and wherein x 1 , x 2 , x 3 , x 4 , x 5 , x 6 , x 7 and x 8 each have a value from about 0 to about 1; and n 1 , n 2 , n 3 , n 4 , n 5 , n 6 , n 7 , n 8 , m and m 1 each have a value of from about 0 to about 18.

10 . The method of claim 9 wherein when any, but not more than five of, n 1 , n 2 , n 3 , n 4 , n 5 , n 6 , n 7 , or n 8 is zero at any one time then a corresponding x 1 , x 2 , x 3 , x 4 , x 5 , x 6 , x 7 or x 8 is zero and wherein when any of R 1 , R 2 , R 3 R 4 , R 5 , R 6 , R 7 or R 8 is a hydrogen and a corresponding x 1 -n 1 , x 2 -n 2 , x 3 -n 3 , x 4 -n 4 , x 5 -n 5 , x 6 -n 6 , x 7 -n 7 , or x 8 -n 8 pair is zero the nitrogen is directly bonded to hydrogen.

11 . The method of claim 9 wherein any, but not all of, x 1 , x 2 , x 3 , x 4 , x 5 , x 6 , x 7 or x 8 is zero at the same time and a corresponding R 1 , R 2 , R 3 R 4 , R 5 , R 6 , R 7 or R 8 independently bonds directly to the carbon of a corresponding (CH 2 )n.

12 . The method of claim 1 wherein the esterquat provides at least 60% biodegradability in 28 days as determined in accordance with OECD 301B.

13 . The method of claim 1 wherein the esterquat is present in the composition in an amount of from about 0.5 ppb to about 20 ppb.

14 . The method of claim 1 wherein the invert emulsion drilling fluid has a density from about 9 to about 18 ppg.

15 . The method of claim 1 wherein the oleaginous continuous phase comprises petroleum oil, natural oil, synthetically derived oil, an alpha olefin, an internal olefin, an ester, a diester of carbonic acid, a paraffin, kerosene oil, diesel oil, mineral oil or combinations thereof.

16 . The method of claim 1 wherein invert emulsion drilling fluid has an oil water ratio from about 50:50 to about 95:5.

17 . The method of claim 1 wherein the non-oleaginous discontinuous phase comprises an aqueous solution of a water activity lowering material selected from the group consisting of sugar; glycerol; salts selected from the group consisting of calcium chloride, calcium bromide, sodium chloride, sodium bromide, formate, and combinations thereof.

18 . A method of servicing a wellbore comprising introducing a clay-free invert emulsion drilling fluid comprising distearoylethyl dimonium chloride to the wellbore.

19 . The method of claim 18 wherein the invert emulsion fluid comprises petroleum oil, natural oil, synthetically derived oil, an alpha olefin, an internal olefin, an ester, a diester of carbonic acid, a paraffin, kerosene oil, diesel oil, mineral oil or combinations thereof.

20 . The method of claim 18 wherein the aqueous solution contains a water activity lowering material selected from the group consisting of sugar; glycerol; salts selected from the group consisting of calcium chloride, calcium bromide, sodium chloride, sodium bromide, formate, and combinations thereof.

21 . The method of claim 18 wherein the invert emulsion drilling fluid has an oil:water ratio of from about 60:40 to about 90:10.

22 . A wellbore servicing fluid comprising an invert emulsion drilling fluid having an oleaginous continuous phase, a non-oleaginous discontinuous phase, and a fluid loss additive into a wellbore wherein the fluid loss additive comprises an esterquat characterized by Structure A: