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US 8,236,737 B2Granted
Particles comprising a fluorinated siloxane and methods of making and using the same
Assignee3M Innovative Properties Company
InventorsWayne W. Fan, John D. Skildum
Life of this patent
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Abstract
Particles, including proppants, comprising a fluorinated siloxane. The particles are useful as proppants in fractured a subterranean geological formation comprising hydrocarbons.
Claims23
A particle treated with at least one fluorinated siloxane, the particle being at least 500 micrometers in size, wherein the fluorinated siloxane comprises a condensation product of at least one reactive fluorinated silane selected from the group consisting of:
- Rf{-Q-[SiY3−x(R)x]y}z;
- a polymeric fluorinated composition comprising:
- at least one divalent unit represented by the formula:
- and
- at least one of
- at least one divalent unit represented by the formula:
- or
- a chain-terminating group represented by the formula:
- —S—W—SiY3−x(R)x;
- and
- a fluorinated urethane oligomer of at least two repeat units comprising:
- at least one end group represented by the formula —O—Z—Rf2, and
- at least one end group represented by the formula —X1—W—SiY3−x(R)x;
- wherein
- Rf is a monovalent or multivalent perfluoroalkyl group optionally interrupted by at least one —O—;
- Rf2 is a monovalent perfluoroalkyl group optionally interrupted by at least one —O—;
- each R is independently selected from the group consisting of alkyl having one to six carbon atoms and aryl;
- Q is a divalent or trivalent organic linking group containing from 1 to 4 functional groups selected from the group consisting of ester, amide, sulfonamide, carbonyl, carbonate, urea, and carbamate;
- each Y is independently selected from the group consisting of hydroxyl, alkoxy, acyloxy, and halogen;
- each R1 is independently selected from the group consisting of hydrogen and alkyl having one to four carbon atoms;
- each W is independently selected from the group consisting of alkylene, arylalkylene, and arylene, wherein alkylene is optionally interrupted or substituted by at least one heteroatom;
- each X is independently selected from the group consisting of —NH—, —O—, and —S—;
- X1 is selected from the group consisting of —N(H)—, —O—, —O—C(O)—NH—, and —O-alkylene-O—C(O)—NH—;
- Z is a divalent organic linking group;
- x is 0, 1, or 2;
- y is 1 or 2;
- and
- z is 1, 2, 3, or 4.
25 more elements
A particle treated with at least one fluorinated siloxane, wherein the particle is a ceramic particle having a plurality of pores or an engineered proppant, wherein the fluorinated siloxane comprises a condensation product of at least one reactive fluorinated silane selected from the group consisting of:
- Rf{-Q-[SiY3−x(R)x]y}z;
- a polymeric fluorinated composition comprising:
- at least one divalent unit represented by the formula:
- and
- at least one of
- at least one divalent unit represented by the formula:
- or
- a chain-terminating group represented by the formula:
- —S—W—SiY3−x(R)x;
- and
- a fluorinated urethane oligomer of at least two repeat units comprising:
- at least one end group represented by the formula —O—Z—Rf2, and
- at least one end group represented by the formula —X1—W—SiY3−x(R)x;
- wherein
- Rf is a monovalent or multivalent perfluoroalkyl group optionally interrupted by at least one —O—;
- Rf2 is a monovalent perfluoroalkyl group optionally interrupted by at least one —O—;
- each R is independently selected from the group consisting of alkyl having one to six carbon atoms and aryl;
- Q is a divalent or trivalent organic linking-group containing from 1 to 4 functional groups selected from the group consisting of ester, amide, sulfonamide, carbonyl, carbonate, urea, and carbamate;
- each Y is independently selected from the group consisting of hydroxyl, alkoxy, acyloxy, and halogen;
- each R1 is independently selected from the group consisting of hydrogen and alkyl having one to four carbon atoms;
- each W is independently selected from the group consisting of alkylene, arylalkylene, and arylene, wherein alkylene is optionally interrupted or substituted by at least one heteroatom;
- each X is independently selected from the group consisting of —NH—, —O—, and —S—;
- X1 is selected from the group consisting of —N(H)—, —S—, —O—, —O—C(O)—NH—, and —O-alkylene-O—C(O)—NH—;
- Z is a divalent organic linking group;
- x is 0, 1, or 2;
- y is 1 or 2;
- and
- z is 1, 2, 3, or 4.
25 more elements
A method of fracturing a subterranean geological formation comprising hydrocarbons, the method comprising:
- injecting a hydraulic fluid into a subterranean geological formation comprising hydrocarbons at a rate and pressure sufficient to open a fracture therein;
- and
- injecting into the fracture a fluid comprising a plurality of particles treated with at least one fluorinated siloxane, wherein the fluorinated siloxane comprises a condensation product of at least one reactive fluorinated silane selected from the group consisting of:
- Rf{-Q-[SiY3−x(R)x]y}z;
- a polymeric fluorinated composition comprising:
- at least one divalent unit represented by the formula:
- and
- at least one of
- at least one divalent unit represented by the formula:
- or
- a chain-terminating group represented by the formula:
- —S—W—SiY3−x(R)x;
- and
- a fluorinated urethane oligomer of at least two repeat units comprising:
- at least one end group represented by the formula —O—Z—Rf2, and
- at least one end group represented by the formula —X1—W—SiY3−x(R)x;
- wherein
- Rf is a monovalent or multivalent perfluoroalkyl group optionally interrupted by at least one —O—;
- Rf2 is a monovalent perfluoroalkyl group optionally interrupted by at least one —O—;
- each R is independently selected from the group consisting of alkyl having one to six carbon atoms and aryl;
- Q is a divalent or trivalent organic linking group containing from 1 to 4 functional groups selected from the group consisting of ester, amide, sulfonamide, carbonyl, carbonate, urea, and carbamate;
- each Y is independently selected from the group consisting of hydroxyl, alkoxy, acyloxy, and halogen;
- each R1 is independently selected from the group consisting of hydrogen and alkyl having one to four carbon atoms;
- each W is independently selected from the group consisting of alkylene, arylalkylene, and arylene, wherein alkylene is optionally interrupted or substituted by at least one heteroatom;
- each X is independently selected from the group consisting of —NH—, —O—, and —S—;
- X1 is selected from the group consisting of —N(H)—, —S—, —O—, —O—C(O)—NH—, and —O-alkylene-O—C(O)—NH—;
- Z is a divalent organic linking group;
- x is 0, 1, or 2;
- y is 1 or 2;
- and
- z is 1, 2, 3, or 4.
28 more elements
Dependencies are inferred from the claim text.