Friction reducers, fluid compositions and uses thereof
US-12054669-B2 · Aug 6, 2024 · US
US2016177162A1 · US · A1
| Field | Value |
|---|---|
| Publication number | US-2016177162-A1 |
| Application number | US-201314910511-A |
| Country | US |
| Kind code | A1 |
| Filing date | Oct 16, 2013 |
| Priority date | Oct 16, 2013 |
| Publication date | Jun 23, 2016 |
| Grant date | — |
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Various embodiments disclosed relate to methods of treating subterranean formations, and compositions, systems and methods for performing the methods. In some embodiments, the present invention provides a method of treating a subterranean formation, including obtaining or providing a composition that includes an alkenoate ester. The composition also includes at least one of a dialkenyldihydrocarbylammonium halide and an N,Ndihydrocarbyl-substituted alkenamide. The method also includes placing the composition in a subterranean formation downhole. Various embodiments provide methods of treating a subterranean formation using a composition including a polymer that is a reaction product of a mixture including an alkenoate ester and at least one of a dialkenyldihydrocarbylammonium halide and an N,N-dihydrocarbyl-substituted alkenamide.
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1 - 163 . (canceled) 164 . A method of treating a subterranean formation, the method comprising: obtaining or providing a composition comprising an alkenoate ester; and at least one of a dialkenyldihydrocarbylammonium halide, and an N,N-dihydrocarbyl-substituted alkenamide; and placing the composition in a subterranean formation downhole. 165 . The method of claim 164 , further comprising polymerizing the composition. 166 . The method of claim 164 , wherein the method comprises a method of hydraulic fracturing. 167 . The method of claim 164 , wherein the method comprises a method of drilling. 168 . The method of claim 164 , further comprising, prior to placing the composition in the subterranean formation, mixing the composition with a particulate substrate to form a particulate mixture, wherein placing the composition in the subterranean formation comprises contacting the subterranean material with the particulate mixture. 169 . The method of claim 164 , wherein the composition further comprises a radical initiator. 170 . The method of claim 164 , wherein the composition further comprises a coupling agent comprising at least one of a diol, polyol, diamine, polyamine, and a silane coupling agent. 171 . The method of claim 164 , wherein the composition further comprises at least one of an epoxide-containing resin, a polyepoxide resin, a novolak resin, a polyester resin, phenolaldehyde resin, a urea-aldehyde resin, a furan resin, a urethane resin, and a glycidyl ether resin. 172 . The method of claim 164 , wherein the composition further comprises at least one organic compound comprising at least one of an amine and an amide, wherein the amine is an aromatic amine, an aliphatic amine, a cyclo-aliphatic amine, a polyamine, or a combination thereof, wherein the amide is a mono- or polyamide. 173 . The method of claim 164 , wherein the composition further comprises at least one of piperidine, triethylamine, benzyldimethylamine, N,N-dimethylaminopyridine, 2-(N,N-dimethylaminomethyl)phenol, tris(dimethylaminomethyl)phenol, 4,4′-diaminodiphenyl sulfone, 2-ethyl-4-methyl imidazole, and 1,1,3-trichlorotrifluoroacetone. 174 . The method of claim 164 , wherein the composition further comprises at least one of acrylic acid and acrylamide. 175 . The method of claim 164 , wherein the alkenoate ester is a (C 1 -C 30 )alkyl (C 1 -C 10 )alkenoate ester or a poly((C 2 -C 30 )alkenyene oxide) (C 1 -C 10 )alkenoate ester, wherein the (C 1 -C 30 )alkyl, (C 1 -C 30 )alkenyene, and (C 1 -C 10 )alkenoate are independently substituted or unsubstituted. 176 . The method of claim 164 , wherein the alkenoate ester has the structure wherein R 1 , R 2 , and R 3 are each independently selected from the group consisting of —H and substituted or unsubstituted (C 1 -C 30 )hydrocarbyl interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S, L 1 is independently selected from a bond and substituted or unsubstituted (C 1 -C 30 )hydrocarbylene interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S, and R 4 is independently selected from the group consisting of a substituted or unsubstituted (C 1 -C 30 )hydrocarbyl interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S, and —R—(O—R) n —OH, wherein R is a substituted or unsubstituted (C 2 -C 10 )hydrocarbylene and n is about 0 to about 10,000. 177 . The method of claim 164 , wherein the N,N-dihydrocarbyl-substituted alkenamide is N,N-di((C 1 -C 30 )alkyl)-substituted (C 1 -C 30 )alkenamide, wherein the (C 1 -C 30 )alkyl groups are independently selected and the (C 1 -C 30 )alkyl and (C 1 -C 10 )alkenamide groups are independently substituted or unsubstituted. 178 . The method of claim 164 , wherein the N,N-dihydrocarbyl-substituted alkenamide has the structure wherein R 5 , R 6 , and R 7 are each independently selected from the group consisting of —H and substituted or unsubstituted (C 1 -C 30 )hydrocarbyl interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S, R 8 and R 9 are each independently substituted or unsubstituted (C 1 -C 30 )hydrocarbyl interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S, and L 2 is independently selected from a bond and substituted or unsubstituted (C 1 -C 30 )hydrocarbylene interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S. 179 . The method of claim 164 , wherein the composition comprises the alkenoate ester and the dialkenyldihydrocarbylammonium halide, wherein the alkenoate ester has the structure wherein R 1 , R 2 , and R 3 are each independently selected from the group consisting of —H and substituted or unsubstituted (C 1 -C 30 )hydrocarbyl interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S, L 1 is independently selected from a bond and substituted or unsubstituted (C 1 -C 30 )hydrocarbylene interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S, and R 4 is selected from the group consisting of a substituted or unsubstituted (C 1 -C 30 )hydrocarbyl interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S, and —R—(O—R) n —OH, wherein R is a substituted or unsubstituted (C 2 -C 10 )hydrocarbylene and n is about 0 to about 10,000; and wherein the dialkenyldihydrocarbylammonium halide has the structure wherein X − is selected from the group consisting of I − , Br − , and Cl − , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 are each independently selected from the group consisting of —H and substituted or unsubstituted (C 1 -C 30 )hydrocarbyl interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S, R 10 and R 11 are each independently a substituted or unsubstituted (C 1 -C 30 )hydrocarbyl interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S, and L 3 and L 4 are independently selected from a bond and substituted or unsubstituted (C 1 -C 30 )hydrocarbylene interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S. 180 . The method of claim 164 , wherein the composition comprises the alkenoate ester and the N,N-dihydrocarbyl-substituted alkenamide, wherein the alkenoate ester has the structure wherein R 1 , R 2 , and R 3 are each independently selected from the group consisting of —H and substituted or unsubstituted (C 1 -C 30 )hydrocarbyl interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S, L 1 is independently selected from a bond and substituted or unsubstituted (C 1 -C 30 )hydrocarbylene interrupted or terminated by 0, 1, 2, or 3 atoms selected from the group consisting of O, NH, and S, and R 4 is selected
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