GB2116966A - Aqueous compositions of N-oxyalkylated quaternary ammonium salt surfactants - Google Patents
Aqueous compositions of N-oxyalkylated quaternary ammonium salt surfactants Download PDFInfo
- Publication number
- GB2116966A GB2116966A GB08304830A GB8304830A GB2116966A GB 2116966 A GB2116966 A GB 2116966A GB 08304830 A GB08304830 A GB 08304830A GB 8304830 A GB8304830 A GB 8304830A GB 2116966 A GB2116966 A GB 2116966A
- Authority
- GB
- United Kingdom
- Prior art keywords
- surfactant
- surfactant composition
- composition according
- carbon atoms
- anion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 150000003242 quaternary ammonium salts Chemical class 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 11
- 239000006185 dispersion Substances 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- 125000005702 oxyalkylene group Chemical group 0.000 claims abstract description 3
- 239000003921 oil Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000010779 crude oil Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000013535 sea water Substances 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 238000011084 recovery Methods 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 description 10
- 239000004576 sand Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000005755 formation reaction Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- -1 glycol halides Chemical class 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/607—Compositions for stimulating production by acting on the underground formation specially adapted for clay formations
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
- C08G65/33306—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group acyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A surfactant composition comprises an aqueous dispersion of a surfactant containing in its molecule an oxyalkylene chain and one or more quaternary nitrogen atoms. The composition is suitable for modifying the wettability of an underground oil-bearing formation and may be used for enhanced oil recovery or injectivity improvement.
Description
SPECIFICATION
Compositions suitable for modifying wettability and their use
This invention relates to surfactant compositions suitable for use in the recovery of crude oil, in particular to surfactant compositions suitable for modifying the wettability of underground formations, and also to a method for employing same.
The use of surfactant compositions to assist in the recovery of crude oil from an underground formation has been previously proposed and several surfactants have been described which modify the wettability of the underground formation.
An improved surfactant composition has now been invented which has improved wetting characteristics compared with those of the prior art.
According to the present invention there is provided a surfactant composition suitable for modifying the wettability of an underground formation which composition comprises an aqueous dispersion of a surfactant compound containing in its molecule an oxyalkylene chain and one or more quaternary nitrogen atoms.
Preferred surfactant compounds are those of formula: X R33 N-R- (ORlJn-HR23 X wherein R is an alkylene group containing 2 to 6 carbon atoms,
R2 and R3 are alkyl or polyalkyleneoxy groups containing 1 to 8 carbon atoms, n is an integer from 1 to 20 and Xis an anion, preferably a halide; or of formula
wherein R4 is an alkylene group containing 1 to 6 carbon atoms,
R6 and R7 are alkyl groups containing 1 to 8 carbon atoms, m is an integer from 1 to 20 and Y is an anion, preferably a halide.
Surfactant compounds which are particularly convenient are those containing two quaternary nitrogen atoms with a polyoxyalkylene chain between them. Alternatively compounds containing only one quaternary nitrogen atom may be used. In either case one or both of the nitrogen atoms can be in a ring, for example a morpholine ring.
The aqueous component of the dispersion is suitably sea water where this is readily available.
The pH of the dispersion is preferably less than 7. Since sea water is usually slightly alkaline, it should be acidified when used as the aqueous component.
The concentration of surfactant in the dispersion is suitably in the range 0.01 to 1.0% by weight.
According to another aspect of the present invention, there is provided a method for treating a formation either to maintain its water wettability in the presence of crude oil or modify its condition to a water wettable state in the presence of crude oil which method comprises contacting the formation with a surfactant composition as hereinbefore described.
The method may involve a flooding operation commonly referred to as enhanced oil recovery or a more localised well treatment, for example to improve the injectivity of a water injection well.
The invention is illustrated by the following Examples.
PREPARATION 1
Reaction ofpolyethylene glycol halides with trimethylamine
A solution of polyoxyethylene dichloride (av.m.w. 637, 18g, 0.03 mol) in dry ethanol (50 ml) was treated with a 33% solution oftrimethylamine in ethanol (10.1 5g, 0.06 mol) and the mixture heated at refluxfor 70h.
A further quantity of trimethylamine soiution (5.07g, 0.03 mol) was added after 24h. The cooled reaction mixture was evaporated under reduced pressure and the residual yellow liquid treated with ether. The solvents were evaporated and the hygroscopic residue freeze dried, 8.2g. (NMR analysis suggested that the product was approximately 2/3 quaternised).
The reaction may be illustrated thus:
n=13.2 Compound (A)
PREPARATION 2
Reaction of tetramethyl(ethylenediamine) with halo gena ted methoxypolyethylene glycols
A mixture of chloro-methoxypolyethylene glycol (av.m.w. 368, lOg, 0.027 mol) and tetramethylethylene diamine (1.58g, 0.014 mol) in dry acetone (50 ml) was heated at refluxfor 48h. The precipitated quaternary salt was filtered, washed with dry ether and dried in vacuo. (2.5g, approx 15%). (NMR confirms the salt formation).
The reaction may be illustrated thus:
n=1.2
Compound (B) PREPARATION 3
Reaction ofpolyoxypropylene amine with methyl iodide
A mixture of a polyoxypropylene amine solid under the Trade Name Jeffamine D-230 (10g, 0.04 mol), sodium bicarbonate (21 .67g, 0.26 mol), methyl iodide (36.62g, 0.26 mol) and methanol (100 ml) was heated under reflux with stirring for 72h. Methyl iodide (9.1 6g) was added after 24 and 48h; The total amount of methyl iodide used was about 0.39 mol. The reaction mixture was evaporated to dryness under reduced pressure and the residue extracted with boiling chloroform (3 x 100 ml). The combined extracts were evaporated under reduced pressure and the residue freeze dried. (5.8g, 23%). (NMR confirmed the product structure).
The reaction may be illustrated thus:
n=2.6 Compound (C)
Example 1
Solutions of the compounds of formulae (A), (B) and (C) prepared as described above were made up with acid adjusted sea water (pH 6.5 - adjusted with HCI) to a concentration of 0.2% by weight.
Forties separator sand (MeOH/toluene extracted) in size fraction < 500 micron was mixed with excess surfactant at 96"C for a minimum of 18 hours. The sand was then filtered with hot (96"C) distilled water several times until no foaming existed; and the sand was then dried in an oven.
Wetting test
Several grains were placed in a bottle and the sea water solution of surfactant (pH 6.5) added. The sand was contacted with a drop of Forties Oil injected from a micrometer syringe and the oil wetting behaviour of the sand in the aqueous environment oil was observed and recorded.
The qualitative results were ranged according to the scale: 1 = Grains not attached to the oil drop
2 = Grains very weakly attached - removed by shaking
3 = Grains moderately attached - removed by shaking
4 = Grains strongly attached - removed by shaking
5 = Grains attached but not removed by shaking
For comparison the wetting test was repeated but in the absence of surfactant employing the sea water, sand and oil only.
The results were as follows:
Structure Wetting by oil Cle ClO Me3N-ICH2-CH2-0}n CH2-CH2-NMe3 Me3 fl:13.2 Compound (A) CLOMe Me CIO 1e 133 Me-N1 -C112-C112-N Nl-Me n=7 2 ICH2-CH2-O)n-CN3 (CHZ-CHZ-O),-EH3 Compound 18) ie Me3N-CN-(112-(O CH-CH),--N Me3 n=2.6 CH3 CH3 Compound (C) No surfactant | 5 *Only 67% conversion to quaternary salt
These results demonstrate that in the absence of the surfactant the sand grains which are normally water wettable quickly take on an oil wet character, but in the presence of the surfactant the surface of the sand can retain its water wettability in the presence of the crude oil. Also demonstrated is that a surfactant with a polyethyleneoxy chain between its nitrogen atoms is more effective than one with the polyethyleneoxy chains attached to the nitrogen atoms as side chains.
Claims (9)
1. A surfactant composition suitable for modifying the wettability of an underground oil-bearing formation, the composition comprising an aqueous dispersion of a surfactant containing in its molecule an oxyalkylene chain and one or more quaternary nitrogen atoms.
2. A surfactant composition according to claim 1 wherein the surfactant is of formula X R33N-R-tSRlXn-NR23 X wherein R is an alkylene group containing 2 to 6 carbon atoms,
R2 and R3 are alkyl or polyalkyleneoxy groups containing 1 to 8 carbon atoms, n is an integer from 1 to 20 and Xis an anion.
3. A surfactant composition according to claim 1 wherein the surfactants is of formula
wherein R4 is an alkylene group containing 1 to 6 carbon atoms,
R6 and R7 are alkyl groups containing 1 to 8 carbon atoms, m is an integer from 1 to 20 and Y is an anion.
4. A surfactant composition according to any of the preceding claims wherein the anion is a halide.
5. A surfactant composition according to any of the preceding claims wherein the aqueous component of the dispersion is sea water.
6. A surfactant composition according to any on the preceding claims wherein the concentration of surfactant in the dispersion is in the range 0.01 to 1.0% by weight.
7. A surfactant composition according to any of the preceding claims wherein the pH of the composition is less than 7.0.
8. A method for treating a formation either to maintain its water wettability in the presence of crude oil or to modify its condition to a water wettable state in the presence of crude oil which method comprises contacting the formation with a surfactant composition according to any of the preceding claims.
9. A surfactant composition as hereinbefore described with reference to Example 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08304830A GB2116966B (en) | 1982-02-26 | 1983-02-22 | N-oxyalkylated aqueous compositions of quaternary ammenium salt surfactants |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8205803 | 1982-02-26 | ||
| GB08304830A GB2116966B (en) | 1982-02-26 | 1983-02-22 | N-oxyalkylated aqueous compositions of quaternary ammenium salt surfactants |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8304830D0 GB8304830D0 (en) | 1983-03-23 |
| GB2116966A true GB2116966A (en) | 1983-10-05 |
| GB2116966B GB2116966B (en) | 1986-01-15 |
Family
ID=26282094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08304830A Expired GB2116966B (en) | 1982-02-26 | 1983-02-22 | N-oxyalkylated aqueous compositions of quaternary ammenium salt surfactants |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2116966B (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2168708A (en) * | 1982-12-23 | 1986-06-25 | Procter & Gamble | Quaternany ammonium compounds |
| EP0296852A3 (en) * | 1987-06-26 | 1990-06-06 | Minnesota Mining And Manufacturing Company | Method of making purely primary diamines |
| WO1991013859A1 (en) * | 1990-03-09 | 1991-09-19 | Henkel Kommanditgesellschaft Auf Aktien | Compounds containing alkylene oxide units and quaternary ammonium groups |
| WO1996010425A1 (en) * | 1994-10-04 | 1996-04-11 | Alcon Laboratories, Inc. | Use of polyethylene oxide-containing polymeric quaternary ammonium compounds in pharmaceutical compositions |
| WO2008084227A1 (en) * | 2007-01-12 | 2008-07-17 | Halliburton Energy Services, Inc. | Surfactant wash treatment fluids and associated methods |
| US7833943B2 (en) | 2008-09-26 | 2010-11-16 | Halliburton Energy Services Inc. | Microemulsifiers and methods of making and using same |
| US7906464B2 (en) | 2008-05-13 | 2011-03-15 | Halliburton Energy Services, Inc. | Compositions and methods for the removal of oil-based filtercakes |
| US8220548B2 (en) | 2007-01-12 | 2012-07-17 | Halliburton Energy Services Inc. | Surfactant wash treatment fluids and associated methods |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4664848A (en) | 1982-12-23 | 1987-05-12 | The Procter & Gamble Company | Detergent compositions containing cationic compounds having clay soil removal/anti-redeposition properties |
Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1213361A (en) * | 1967-05-15 | 1970-11-25 | Cargill Inc | Quaternary ammonium compounds |
| GB1223730A (en) * | 1967-07-31 | 1971-03-03 | Armour Ind Chem Co | Dialkyl polyethoxylated quaternary ammonium compounds, process for their preparation, and use as a fabric softener |
| GB1266534A (en) * | 1968-02-29 | 1972-03-08 | ||
| GB1268746A (en) * | 1969-04-04 | 1972-03-29 | Fmc Corp | Ethers and quaternary salts |
| GB1287199A (en) * | 1969-01-25 | 1972-08-31 | Basf Ag | New quaternary ammonium salts and their use in softening textile fibrous material |
| GB1298099A (en) * | 1969-10-20 | 1972-11-29 | Kendall & Co | Unsaturated quaternary ammonium compounds and copolymers containing them |
| GB1320996A (en) * | 1970-10-24 | 1973-06-20 | Henkel & Cie Gmbh | Quaternary ammonium bases |
| GB1348517A (en) * | 1970-11-11 | 1974-03-20 | Eisai Co Ltd | Quaternary salts of tri- beta-propyloxyethyl amine derivatives and process for producing same |
| GB1351505A (en) * | 1970-07-29 | 1974-05-01 | Berri Balzac | Terpene derivatives method for their preparation and applications thereof |
| GB1402478A (en) * | 1972-10-13 | 1975-08-06 | Cassella Farbwerke Mainkur Ag | Quaternary ammonium chlorides |
| GB1407015A (en) * | 1971-11-19 | 1975-09-24 | Modokemi Ab | Cationic surface active compounds |
| GB1430608A (en) * | 1972-08-08 | 1976-03-31 | Hoechst Ag | Polyquaternary ammonium compounds and their use as petroleum demulsifiers |
| GB1488046A (en) * | 1973-11-20 | 1977-10-05 | Sandoz Ltd | Antistatic treatment of permeable materials |
-
1983
- 1983-02-22 GB GB08304830A patent/GB2116966B/en not_active Expired
Patent Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1213361A (en) * | 1967-05-15 | 1970-11-25 | Cargill Inc | Quaternary ammonium compounds |
| GB1223730A (en) * | 1967-07-31 | 1971-03-03 | Armour Ind Chem Co | Dialkyl polyethoxylated quaternary ammonium compounds, process for their preparation, and use as a fabric softener |
| GB1266534A (en) * | 1968-02-29 | 1972-03-08 | ||
| GB1287199A (en) * | 1969-01-25 | 1972-08-31 | Basf Ag | New quaternary ammonium salts and their use in softening textile fibrous material |
| GB1268746A (en) * | 1969-04-04 | 1972-03-29 | Fmc Corp | Ethers and quaternary salts |
| GB1298099A (en) * | 1969-10-20 | 1972-11-29 | Kendall & Co | Unsaturated quaternary ammonium compounds and copolymers containing them |
| GB1351505A (en) * | 1970-07-29 | 1974-05-01 | Berri Balzac | Terpene derivatives method for their preparation and applications thereof |
| GB1320996A (en) * | 1970-10-24 | 1973-06-20 | Henkel & Cie Gmbh | Quaternary ammonium bases |
| GB1348517A (en) * | 1970-11-11 | 1974-03-20 | Eisai Co Ltd | Quaternary salts of tri- beta-propyloxyethyl amine derivatives and process for producing same |
| GB1407015A (en) * | 1971-11-19 | 1975-09-24 | Modokemi Ab | Cationic surface active compounds |
| GB1430608A (en) * | 1972-08-08 | 1976-03-31 | Hoechst Ag | Polyquaternary ammonium compounds and their use as petroleum demulsifiers |
| GB1402478A (en) * | 1972-10-13 | 1975-08-06 | Cassella Farbwerke Mainkur Ag | Quaternary ammonium chlorides |
| GB1488046A (en) * | 1973-11-20 | 1977-10-05 | Sandoz Ltd | Antistatic treatment of permeable materials |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2168708A (en) * | 1982-12-23 | 1986-06-25 | Procter & Gamble | Quaternany ammonium compounds |
| EP0296852A3 (en) * | 1987-06-26 | 1990-06-06 | Minnesota Mining And Manufacturing Company | Method of making purely primary diamines |
| JP2543954B2 (en) | 1987-06-26 | 1996-10-16 | ミネソタ マイニング アンド アニユフアクチユアリング カンパニー | Method for producing pure primary diamines |
| WO1991013859A1 (en) * | 1990-03-09 | 1991-09-19 | Henkel Kommanditgesellschaft Auf Aktien | Compounds containing alkylene oxide units and quaternary ammonium groups |
| WO1996010425A1 (en) * | 1994-10-04 | 1996-04-11 | Alcon Laboratories, Inc. | Use of polyethylene oxide-containing polymeric quaternary ammonium compounds in pharmaceutical compositions |
| WO2008084227A1 (en) * | 2007-01-12 | 2008-07-17 | Halliburton Energy Services, Inc. | Surfactant wash treatment fluids and associated methods |
| US8220548B2 (en) | 2007-01-12 | 2012-07-17 | Halliburton Energy Services Inc. | Surfactant wash treatment fluids and associated methods |
| US7906464B2 (en) | 2008-05-13 | 2011-03-15 | Halliburton Energy Services, Inc. | Compositions and methods for the removal of oil-based filtercakes |
| US7833943B2 (en) | 2008-09-26 | 2010-11-16 | Halliburton Energy Services Inc. | Microemulsifiers and methods of making and using same |
| US7960314B2 (en) | 2008-09-26 | 2011-06-14 | Halliburton Energy Services Inc. | Microemulsifiers and methods of making and using same |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2116966B (en) | 1986-01-15 |
| GB8304830D0 (en) | 1983-03-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2749520B2 (en) | Silane having hydrophilic group and surfactant in aqueous medium comprising the silane | |
| EP2209836B1 (en) | Alkoxylated polyalkanolamines | |
| US4528106A (en) | Glucoside surfactants | |
| US4439345A (en) | Demulsification of a crude oil middle phase emulsion | |
| US3231619A (en) | Basic primary amino polyether compositions | |
| GB2116966A (en) | Aqueous compositions of N-oxyalkylated quaternary ammonium salt surfactants | |
| KR890003825A (en) | Process for producing epoxy resin with low halogen content | |
| CN109762535B (en) | Shale intercalation inhibitor prepared from hyperbranched polyamine | |
| US2871266A (en) | Tert-carbinamines | |
| US3110732A (en) | Method for preparing basic polyether compositions | |
| US4609478A (en) | Sulfonated alkyl glucosides and use thereof in oil recovery | |
| EP0363094A1 (en) | Fluorochemical surfactants and process for preparing same | |
| KR930021684A (en) | Polysiloxane Stabilizers Containing Hindered Phenolic and Oxamide Groups | |
| CN108165303B (en) | Crude oil demulsifier and preparation method and use method thereof | |
| US4673436A (en) | N, S containing corrosion inhibitors | |
| US4994626A (en) | Method for the preparation of methyl ethers of polyether polyols employing dimethylsulfate as a methylating agent | |
| US6096240A (en) | Composition for the removal of water from a surface | |
| EP0256980A2 (en) | Fluorinated cationic compounds | |
| EP0080855A2 (en) | Compounds and compositions for oil recovery | |
| US2806019A (en) | Quaternary ammonium compounds of polymers of the cumarone-indene class | |
| KR840007578A (en) | Method for preparing substituted nitro and cyanoguanidines | |
| US2991299A (en) | Titanium trialkanolamine derivatives | |
| US4012441A (en) | Sulphonic derivatives having the structure of polyoxapolyfluoroalkanes | |
| CN115872892B (en) | Waterproof drilling locking agent monomer, waterproof drilling locking agent, and preparation method and application thereof | |
| CN116987213B (en) | Compound with surfactant function, surfactant and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |