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US 2006/0079431 A1Published application
2-Hydroxy-3-alkoxypropyl sulfides, sulfones, and sulfoxides: new surface active agents
AssigneeAir Products and Chemicals, Inc.
InventorsGauri Lal, Williams Raymond, Khalil Yacoub, Evelyn Paulsen
Life of this patent
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Abstract
Compositions containing surfactant compounds according to formula (I) R4OCH2CH(OH)CR2R3ZR1 (I) wherein Z is S, SO, or SO2, can have a range of equilibrium and/or dynamic surface tensions and a range of foaming performance attributes, depending upon the particular values of Z, R1, R2, R3, and R4. The compounds of formula (I) may be prepared by a process that includes reaction of a thiol with a glycidyl ether.
Claims40
A composition comprising a compound according to formula (I)
- R4OCH2CH(OH)CR2R3ZR1 (I)
- wherein R4 is selected from the group consisting of C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties;
- C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties bearing a carbonyl group or one or more heteroatoms selected from O, S, and N;
- glycol ether moieties of the formula R5(OCH2CH2)q—;
- aminoethylene moieties of the formula R5(NHCH2CH2)q—;
- and thioether moieties of the formula R5S(CH2)q—;
- wherein R5 is H or linear C1-C12 alkyl;
- R2 and R3 are each independently selected from the group consisting of H and linear or branched Cl-C3 alkyl and alkenyl groups;
- R1 is selected from the group consisting of C3-C16 linear, cyclic, and branched alkyl, alkenyl, aryl, aralkyl, and alkaryl moieties, and any of these moieties substituted with carboxy, sulfo, or phospho substituents;
- —CH2(CHOH)nCH2OH;
- —(CH2)2O(CH2)2T;
- —(CH2)mT;
- and
- —CH2CH(OH)CH2(C3H6O)pO—R(O(C3H6O)pCH2CHOHCH2T)2;
- wherein m is an integer from 2 to 4, n is an integer from 0 to 5, p is 1 or 2;
- q is an integer from 1 to 15, T is SH or ZCR2R3CH(OH)CH2OR4, R is a trimethylolpropane- or glycerol-based segment, and Z is S, SO, or SO2, provided that Z is not S when R1 is —CH2(CHOH)nCH2OH.
13 more elements
A method of preparing a compound according to formula (I),
- R4OCH2CH(OH)CR2R3ZR1 (I)
- the method comprising contacting at least one compound according to formula (II)
- with a mercaptan R1—SH;
- wherein R4 is selected from the group consisting of C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties;
- C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties bearing a carbonyl group or one or more heteroatoms selected from O, S, and N;
- glycol ether moieties of the formula R5(OCH2CH2)q—;
- aminoethylene moieties of the formula R5(NHCH2CH2)q—;
- and thioether moieties of the formula R5S(CH2)q—;
- wherein R5 is H or linear C1-C12 alkyl;
- R2 and R3 are each independently selected from the group consisting of H and linear or branched C1-C3 alkyl and alkenyl groups;
- R1 is selected from the group consisting of C3-C16 linear, cyclic, and branched alkyl, alkenyl, aryl, aralkyl, and alkaryl moieties, and any of these moieties substituted with carboxy, sulfo, or phospho substituents;
- —CH2(CHOH)nCH2OH;
- —(CH2)2O(CH2)2T;
- —(CH2)mT;
- and
- —CH2CH(OH)CH2(C3H6O)pO—R(O(C3H6O)pCH2CHOHCH2T)2;
- wherein m is an integer from 2 to 4, n is an integer from 0 to 5, p is 1 or 2;
- q is an integer from 1 to 15, T is SH or ZCR2R3CH(OH)CH2OR4, R is a trimethylolpropane- or glycerol-based segment, and Z is S, SO, or SO2, provided that Z is not S when R1 is —CH2(CHOH)nCH2OH.
15 more elements
In a formulation comprising between 0.1 and 99.9 wt % in total of one or more ingredients selected from the group consisting of surfactants and wetting agents other than according to formula (I);
- solvents;
- alkali metal hydroxides;
- water-borne, water-dispersible, or water-soluble resins;
- flow agents;
- leveling agents;
- pigments;
- processing aids;
- defoamers;
- solubilizing agents;
- pesticides;
- plant growth modifying agents;
- water-soluble film-forming macromolecules;
- water-soluble alcohols, glycols, or polyols;
- water-soluble acids or salts thereof;
- tetramethylammonium hydroxide;
- emulsifying agents;
- alkanolamines;
- organic monoacids;
- biocides;
- chelants;
- detergent builders;
- detergent co-builders;
- dyes;
- fragrances;
- anti-redeposition aids;
- sunscreen agents;
- solubilizing agents;
- polymers;
- oligomers;
- functional cement additives;
- sodium chloride;
- sodium bromide;
- calcium chloride;
- calcium bromide;
- zinc chloride;
- zinc bromide;
- cesium formate;
- hydrochloric acid;
- hydrofluoric acid;
- acetic acid;
- formic acid;
- and water;
- the improvement comprising including in the formulation between 0.001 and 45 wt % of one or more compounds according to formula (I)
- R4OCH2CH(OH)CR2R3ZR1 (I)
- wherein R4 is selected from the group consisting of C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties;
- C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties bearing a carbonyl group or one or more heteroatoms selected from O, S, and N;
- glycol ether moieties of the formula R5(OCH2CH2)q—;
- aminoethylene moieties of the formula R5(NHCH2CH2)q—;
- and thioether moieties of the formula R5S(CH2)q—;
- wherein R5 is H or linear C1-C12 alkyl;
- R2 and R3 are each independently selected from the group consisting of H and linear or branched C1-C3 alkyl and alkenyl groups;
- R1 is selected from the group consisting of C3-C16 linear, cyclic, and branched alkyl, alkenyl, aryl, aralkyl, and alkaryl moieties, and any of these moieties substituted with carboxy, sulfo, or phospho substituents;
- —CH2(CHOH)nCH2OH;
- —(CH2)2O(CH2)2T;
- —(CH2)mT;
- and
- —CH2CH(OH)CH2(C3H6O)pO—R(O(C3H6O)pCH2CHOHCH2T)2;
- wherein m is an integer from 2 to 4, n is an integer from 0 to 5, p is 1 or 2;
- q is an integer from 1 to 15, T is SH or ZCR2R3CH(OH)CH2OR4, R is a trimethylolpropane- or glycerol-based segment, and Z is S, SO, or SO2;
- and
- wherein said one or more ingredients does not include any component of a pre- or post-preparation synthesis reaction mixture for preparation of any of the one or more compounds according to formula (I).
58 more elements
In a fluid for drilling, completing, cementing, stimulating, fracturing, acidizing, or working over a subterranean gas or oil well, or for treating or enhancing the production of oil or gas from an oil or gas bearing formation;
- the fluid comprising between 5 and 99.85 wt % in total of at least one of an organic liquid and water and further comprising between 0.1 and 80 wt % in total of one or more ingredients selected from the group consisting of weighting agents, viscosifiers, dispersants, drilling mud base oils, emulsifiers, soluble salts, cements, proppants, mineral acids, organic acids, biocides, defoamers, demulsifiers, corrosion inhibitors, friction reducers, gas hydrate inhibitors, hydrogen sulfide removal or control additives, asphaltene control additives, paraffin control additives, and scale control additives;
- the improvement comprising including in the fluid between 0.05 and 10 wt % of one or more compounds according to formula (I)
- R4OCH2CH(OH)CR2R3ZR1 (I)
- wherein R4 is selected from the group consisting of C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties;
- C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties bearing a carbonyl group or one or more heteroatoms selected from O, S, and N;
- glycol ether moieties of the formula R5(OCH2CH2)q—;
- aminoethylene moieties of the formula R5(NHCH2CH2)q—;
- and thioether moieties of the formula R5S(CH2)q—;
- wherein R5 is H or linear C1-C12 alkyl;
- R2 and R3 are each independently selected from the group consisting of H and linear or branched C1-C3 alkyl and alkenyl groups;
- R1 is selected from the group consisting of C3-C16 linear, cyclic, and branched alkyl, alkenyl, aryl, aralkyl, and alkaryl moieties, and any of these moieties substituted with carboxy, sulfo, or phospho substituents;
- —CH2(CHOH)nCH2OH;
- —(CH2)2O(CH2)2T;
- —(CH2)mT;
- and
- —CH2CH(OH)CH2(C3H6O)pO—R(O(C3H6O)pCH2CHOHCH2T)2;
- wherein m is an integer from 2 to 4, n is an integer from 0 to 5, p is 1 or 2;
- q is an integer from 1 to 15, T is SH or ZCR2R3CH(OH)CH2OR4, R is a trimethylolpropane- or glycerol-based segment, and Z is S, SO, or SO2;
- and
- wherein said one or more ingredients does not include any component of a pre- or post-preparation synthesis reaction mixture for preparation of any of the one or more compounds according to formula (I).
17 more elements
In a method for drilling, completing, cementing, stimulating, fracturing, acidizing, working over, or treating a subterranean well, the improvement comprising injecting into the well a fluid comprising one or more compounds according to formula (I)
- R4OCH2CH(OH)CR2R3ZR1 (I)
- wherein R4 is selected from the group consisting of C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties;
- C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties bearing a carbonyl group or one or more heteroatoms selected from O, S, and N;
- glycol ether moieties of the formula R5(OCH2CH2)q—;
- aminoethylene moieties of the formula R5(NHCH2CH2)q—;
- and thioether moieties of the formula R5S(CH2)q—;
- wherein R5 is H or linear C1-C12 alkyl;
- R2 and R3 are each independently selected from the group consisting of H and linear or branched C1-C3 alkyl and alkenyl groups;
- R1 is selected from the group consisting of C3-C16 linear, cyclic, and branched alkyl, alkenyl, aryl, aralkyl, and alkaryl moieties, and any of these moieties substituted with carboxy, sulfo, or phospho substituents;
- —CH2(CHOH)nCH2OH;
- —(CH2)2O(CH2)2T;
- —(CH2)mT;
- and
- —CH2CH(OH)CH2(C3H6O)pO—R(O(C3H6O)pCH2CHOHCH2T)2;
- wherein m is an integer from 2 to 4, n is an integer from 0 to 5, p is 1 or 2;
- q is an integer from 1 to 15, T is SH or ZCR2R3CH(OH)CH2OR4, R is a trimethylolpropane- or glycerol-based segment, and Z is S, SO, or SO2.
13 more elements
In a method for treating a produced stream of oil or gas from an oil and gas bearing formation, the improvement comprising injecting into the produced stream a fluid comprising one or more compounds according to formula (I)
- R4OCH2CH(OH)CR2R3ZR1 (I)
- wherein R4 is selected from the group consisting of C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties;
- C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties bearing a carbonyl group or one or more heteroatoms selected from O, S, and N;
- glycol ether moieties of the formula R5(OCH2CH2)q—;
- aminoethylene moieties of the formula R5(NHCH2CH2)q—;
- and thioether moieties of the formula R5S(CH2)q—;
- wherein R5 is H or linear C1-C12 alkyl;
- R2 and R3 are each independently selected from the group consisting of H and linear or branched C1-C3 alkyl and alkenyl groups;
- R1 is selected from the group consisting of C3-C16 linear, cyclic, and branched alkyl, alkenyl, aryl, aralkyl, and alkaryl moieties, and any of these moieties substituted with carboxy, sulfo, or phospho substituents;
- —CH2(CHOH)nCH2OH;
- —(CH2)2O(CH2)2T;
- —(CH2)mT;
- and
- —CH2CH(OH)CH2(C3H6O)pO—R(O(C3H6O)pCH2CHOHCH2T)2;
- wherein m is an integer from 2 to 4, n is an integer from 0 to 5, p is 1 or 2;
- q is an integer from 1 to 15, T is SH or ZCR2R3CH(OH)CH2OR4, R is a trimethylolpropane- or glycerol-based segment, and Z is S, SO, or SO2.
13 more elements
A formulation comprising:
- i) a first component corisisting of one or more compounds according to formula (I)
- R4OCH2CH(OH)CR2R3ZR1 (I)
- wherein R4 is selected from the group consisting of C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties;
- C3-C30 branched, linear, and cyclic alkyl, alkenyl, aryl, and aralkyl moieties bearing a carbonyl group or one or more heteroatoms selected from O, S, and N;
- glycol ether moieties of the formula R5(OCH2CH2)q—;
- aminoethylene moieties of the formula R5(NHCH2CH2)q—;
- and thioether moieties of the formula R5S(CH2)q—;
- wherein R5 is H or linear C1-C12 alkyl;
- R2 and R3 are each independently selected from the group consisting of H and linear or branched C1-C3 alkyl and alkenyl groups;
- R1 is selected from the group consisting of C3-C16 linear, cyclic, and branched alkyl, alkenyl, aryl, aralkyl, and alkaryl moieties, and any of these moieties substituted with carboxy, sulfo, or phospho substituents;
- —CH2(CHOH)nCH2OH;
- —(CH2)2O(CH2)2T;
- —(CH2)mT;
- and
- —CH2CH(OH)CH2(C3H6O)pO—R(O(C3H6O)pCH2CHOHCH2T)2;
- wherein m is an integer from 2 to 4, n is an integer from 0 to 5, p is 1 or 2;
- q is an integer from 1 to 15, T is SH or ZCR2R3CH(OH)CH2OR4, R is a trimethylolpropane- or glycerol-based segment, and Z is S, SO, or SO2;
- and
- ii) a second component consisting of one or more materials selected from the group consisting of nonvolatile organic and nonvolatile inorganic materials and mixtures of these, said second component not including any component of a pre- or post-preparation synthesis reaction mixture for preparation of any of the one or more compounds according to formula (I);
- wherein the formulation is fluid at 25° C.
17 more elements
Dependencies are inferred from the claim text.