CN103380208A - Compositions comprising alkylalkoxysulfonates for the production of high temperature stable foams - Google Patents
Compositions comprising alkylalkoxysulfonates for the production of high temperature stable foams Download PDFInfo
- Publication number
- CN103380208A CN103380208A CN2012800096268A CN201280009626A CN103380208A CN 103380208 A CN103380208 A CN 103380208A CN 2012800096268 A CN2012800096268 A CN 2012800096268A CN 201280009626 A CN201280009626 A CN 201280009626A CN 103380208 A CN103380208 A CN 103380208A
- Authority
- CN
- China
- Prior art keywords
- aqueous composition
- foam
- hydrogen
- alkoxyl group
- preferred
- 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
- 239000006260 foam Substances 0.000 title claims abstract description 85
- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 40
- -1 steam Substances 0.000 claims description 34
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 25
- 239000000654 additive Substances 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 239000007789 gas Substances 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000004064 cosurfactant Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- 239000006184 cosolvent Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 235000011089 carbon dioxide Nutrition 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003570 air Substances 0.000 claims description 2
- 235000009508 confectionery Nutrition 0.000 claims description 2
- 239000002737 fuel gas Substances 0.000 claims description 2
- 239000004530 micro-emulsion Substances 0.000 claims description 2
- 239000003345 natural gas Substances 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 238000005755 formation reaction Methods 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 35
- 239000011734 sodium Substances 0.000 description 21
- 239000004094 surface-active agent Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 11
- 239000010410 layer Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
- 239000011148 porous material Substances 0.000 description 8
- 238000011084 recovery Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000005553 drilling Methods 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000001737 promoting effect Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000004141 Sodium laurylsulphate Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 2
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002734 clay mineral Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229940094522 laponite Drugs 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000004080 punching Methods 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 1
- JBVOQKNLGSOPNZ-UHFFFAOYSA-N 2-propan-2-ylbenzenesulfonic acid Chemical compound CC(C)C1=CC=CC=C1S(O)(=O)=O JBVOQKNLGSOPNZ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000010796 Steam-assisted gravity drainage Methods 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229940071118 cumenesulfonate Drugs 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004049 embossing Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005242 forging Methods 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000015784 hyperosmotic salinity response Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 208000001491 myopia Diseases 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CTYRPMDGLDAWRQ-UHFFFAOYSA-N phenyl hydrogen sulfate Chemical compound OS(=O)(=O)OC1=CC=CC=C1 CTYRPMDGLDAWRQ-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 238000005491 wire drawing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/143—Sulfonic acid esters
-
- 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
- C09K8/02—Well-drilling compositions
- C09K8/38—Gaseous or foamed well-drilling compositions
-
- 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
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
-
- 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
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/592—Compositions used in combination with generated heat, e.g. by steam injection
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- 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
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/594—Compositions used in combination with injected gas, e.g. CO2 orcarbonated gas
-
- 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
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/70—Compositions for forming crevices or fractures characterised by their form or by the form of their components, e.g. foams
- C09K8/703—Foams
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- 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
- C09K8/92—Compositions for stimulating production by acting on the underground formation characterised by their form or by the form of their components, e.g. encapsulated material
- C09K8/94—Foams
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/40—Specific cleaning or washing processes
- C11D2111/42—Application of foam or a temporary coating on the surface to be cleaned
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- Chemical Kinetics & Catalysis (AREA)
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- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
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Abstract
The present invention is directed to the use of alkylalkoxysulfonates for the production of foams, which are stable at high temperatures, e.g. up to about 250 DEG C. Furthermore, the invention relates to a method for producing of high temperature stable foams by using a foamable aqueous composition comprising at least one linear alkylalkoxysulfonate.
Description
The present invention relates to alkyl alkoxy sulfonate and be created in high temperature, for example purposes in about 250 ℃ of lower stable foams at the most.In addition, the present invention relates to a kind of by use comprise at least a straight chained alkyl alkoxyl group sulfonate can be foaming aqueous composition produce the method for high-temperature stable foam.
Tensio-active agent is generally used in makeup, medicine and the washing composition, and wherein use temperature is usually less than 100 ℃.The known surface promoting agent that is used for washing under about 10-100 ℃ temperature, cleaning and foaming application has at least one C usually
8-
16Alkyl chain is as hydrophobic part.With regard to this purpose, have that often use is little and to have low interface active under these conditions than the tensio-active agent of long alkyl chain.
Some use temperatures are higher than 100 ℃ tensio-active agent and have at least one at least C
18Alkyl chain to improve the residence time at the interface.Especially, the typically used of stable high-temperature stable tensio-active agent is high temperature emulsification, hot wash, oil recovery application and the drilling well additive of for example polymer melt under 150-250 ℃ of temperature.
A kind of important application of tensio-active agent is that it can promote formation of foam as pore forming material (being also referred to as lathering surfactant).Foam is generally the composition of air inclusion and liquid, and it forms by the bubble in the catch liquid (such as water), and wherein said bubble separates by the liquid film (being so-called thin layer) that links to each other.The foam layer that comprises liquid (such as water) is stablized by at least a tensio-active agent that shows into film properties usually.In some cases, described foam can be described as the soliquid of gas in liquid.
When known pore forming material or lathering surfactant are in being dissolved in liquid phase usually, during particularly with a small amount of dissolving, can promote formation of foam and can pass through to suppress the coalescent colloidal stability that improves foam of bubble.Can think that lathering surfactant is at the interface with monolayer adsorption and be gathered into stable foam layer.The interfacial viscosity that improves provides film attenuation and the mechanical resistance of breaking.Be used for the common known lathering surfactant that temperature is lower than 100 ℃ and be for example sodium lauryl sulphate (SDS), Texapon Special (ALS), Zetesol NL (SLES) and betaines.
Pore forming material particularly can be used at the pore forming material of stable foam under the high temperature and high pressure in the various application.The important applied field of high-temperature stable foam is field use, such as the probing, particularly tertiary oil recovery technology of acid volume increase, underground heat reservoir such as hot radical oil recovery technique (SAGD for example, " gravity drainage that steam is auxiliary "; CSS, " steam stimulation "), this need to improve performance under hot conditions.Also will be used for application-specific as being higher than the foam composition that demonstrates high stability under 150 ℃ in the temperature that raises, in metal processing (for example punching press, stretching, shaping, bending, rolling, cutting, grinding, punching, saw, hobbing, fraising, wire drawing, extrude trepanning, embossing, forging), the probing of underground heat reservoir, extraordinary cleaning applications and flame-retardant foam.
Proposed various tensio-active agents and surfactant mixture are used for field use, especially at high temperature used in the field use of foam.
US 4,201, and 678 have described the mixture of a kind of both sexes trimethyl-glycine, linear aliphatic or alkylated aromatic sulfonic acid salt and optional not neutralization of ammonia.This mixture can be used as the pore forming material in the foam drilling and works in temperature is higher than 200 ℃ hot hole.
WO 94/18431 relates to for improving the oil recovery under 38-120 ℃ of temperature and comprising C
10-16Alkene sulfonic acid salt surfactant and solubilize compound are to improve the Efferescent compositions of salt tolerance.
CN-A 1 927 993 has described high-temperature stratum from Efferescent compositions and the application in the viscous oil exploitation thereof.Said composition comprises sulfonated α-olefin or dialkyl diphenyl ether stilbene-4,4'-bis-(1-azo-3, 4-dihydroxy-benzene)-2,2'-disulfonate as pore forming material.
Document US 5,193,618 disclose the method for auxiliary (EOR) technology recovery of hydrocarbons from oil reservoir of recovering the oil of a kind of use steam, and wherein composition comprises foam GO TO table surface-active agent, alkyl aromatic sulfonates particularly, and comprise the dimeric precipitation control of sulfonated α-olefin additive.
US 2005/0137114 has described a kind of foam composition in about 80-160 ℉ (27-70 ℃) temperature range, it comprises at least a anion surfactant, at least a cats product and one or more zwitterionic compounds, and wherein said anion surfactant is selected from pure ether sodium sulfate or pure ether ammonium sulfate, alkylether sulfonate, alkylaryl sulphonate and composition thereof.
Alkyl alkoxy sulfonate and preparation method thereof is that prior art is known.Document DE-A 36 22 439 has described C
8-18The purposes of alkylether sulfonate in cosmetic applications.Document US 4,088,189 have described the poly-alkoxyalkyl sulfonate of the alkyl that is used for the auxiliary oil-extraction method of tensio-active agent and the poly-alkoxyalkyl sulfonate of alkylaryl.
Yet, being starved of excellent lathering surfactant and foam composition with high thermal stability, it can easily prepare and be used under 100-250 ℃ the temperature and forms foam.Need to be used for especially some application such as foam drilling application or thermal recovery oil under being higher than 150 ℃ uses.In addition, common importantly tensio-active agent demonstrates enough stability with the foam that produces to higher salt concentrations and contacts with oil phase in some application.
The purpose of this invention is to provide improved tensio-active agent and preparation in the method for lower stable foam composition, particularly water-based foam of high temperature (for example 150-250 ℃).These foam composition should be in long-time, particularly at the most 1 day, preferably at the most 10 days, usually demonstrates at the most high-temperature stability (for example at the most 100 ℃) in 60 days, and also demonstrate high stability when contacting with hydrocarbon phase.In addition, need tensio-active agent having chemical stability under 250 ℃ of temperature at the most, and at room temperature have good water-solublely, this is as solution being pumped into the prerequisite in the well in some application.Except high thermal resistance, described pore forming material is welding not, should not produce residue and can easily obtain with low cost.
Be surprisingly found out that to contain and have 14-36 carbon atom, particularly 20-30, the linear alkyl chain of preferred 22-28 carbon atom and have 1-20 oxyalkyl units, preferably the specific sulfonate of 1-10 oxyalkyl units is chemically stable and is producing foam under 250 ℃ the temperature at the most.Find that further salt (for example Repone K) improves froth stability.The optimum quantity of stand-by salt depends on surfactant structure.Also the mixture of long and short alkyl chain tensio-active agent can be used for regulate solvability, surfactivity and froth stability.
The straight chained alkyl alkoxyl group sulfonate that the present invention relates at least a formula (I) is used at 100-250 ℃, and preferred 150-250 ℃, usually also be 180-250 ℃, produce the purposes of foam under preferred 200-250 ℃ the temperature:
Wherein:
R
1For having 14-36, preferably 20-30, preferred 22-30, preferred 22-28 is individual, more preferably the linear alkyl chain of 24-28 carbon atom;
R
aBe hydrogen or methyl separately independently for n oxyalkyl units;
R
bBe hydrogen or methyl separately independently for n oxyalkyl units;
Condition is for n oxyalkyl units separately, at least one R
aOr R
bBe not hydrogen;
M is 0-10, the number of preferred 1-8;
N is 0-10, the number of preferred 1-8;
P is 0-20, the number of preferred 1-8;
Condition is m+n+p〉0;
X is selected from Na
+, K
+, Mg
2+And NH
4 +,
Y is 1 or 2 integer.
In addition, the present invention relates to aforesaid formula (I) straight chained alkyl alkoxyl group sulfonate produces the high-temperature stable foam as tensio-active agent purposes.
" foam " of the present invention or " foam composition " are the composition of the tensio-active agent of air inclusion, liquid and conduct layer stablizer, it is by the bubble formation in the catch liquid (for example water), and wherein said bubble separates by the liquid film (so-called thin layer) that links to each other.The foam thin layer that comprises liquid such as water is usually stable by at least a tensio-active agent, and it shows into film properties.In some cases, described foam can be described as the soliquid of gas in liquid.Described thin layer is via the intersection connection and form the network that intersects.Described bubble can be spherical and have weak interaction-particularly gas volume fraction less than about 74% situation under.
In other situations of higher gas volume fraction, bubble shape can be polyhedron distortion.In actual foam, bubble normally unordered and have various foam sizes (polydispersion foam).
Especially, for the present invention, tensio-active agent (lathering surfactant) promotes the tensio-active agent of formation of foam in being dissolved in liquid phase when particularly dissolving on a small quantity.Pore forming material or lathering surfactant can be by suppressing the coalescent colloidal stability that improves foam of bubble.
" foam of high-temperature stable " of the present invention mean lather volume at 100 ℃ at the most (especially at 150 ℃ at the most, usually at 150-250 ℃) temperature under at 100 seconds or longer (preferably above 200 seconds, preferably above 300 seconds) reduce afterwards less than 10% (preferably less than 5%, being more preferably less than 2%).Froth stability can be described by can be observed foam (foam layer fracture) the front time that begins to cave in.
Preferably, the radicals R in the formula (I)
1Individual for having 14-36, preferred 20-30, also preferred 22-30, preferred 22-28 is individual, more preferably the linear alkyl chain of 24-28 carbon atom.Generally speaking, straight chained alkyl alkoxyl group sulfonate of the present invention preferably can prepare by commercially available alcohol (for example Fatty Alcohol(C12-C14 and C12-C18)) or the alkoxylate of alcohol mixture in known in principle mode.Therefore, radicals R herein
1Carbonatoms can represent in known manner the mean number of existing carbon atom in the described alkyl alkoxy sulfonate, represent respectively the maximum distribution of carbonatoms in the alkyl chain.
The used straight chained alkyl alkoxyl group sulfonate of the present invention usually demonstrate have formula (I) to the block structure of general structure.The used straight chained alkyl alkoxyl group sulfonate of the present invention comprises m general formula-O-(C usually
4H
8) butoxy, n general formula-O-CH
2-CH (CH
3)-propoxy-and p general formula-O-CH
2CH
2-oxyethyl group.
Herein, propoxy-formula-O-CH
2-CH (CH
3)-clearly is intended to also comprise formula-O-CH (CH
3)-CH
2)-the unit, therefore contain reverse alkoxyl group in the described straight chained alkyl alkoxyl group sulfonate.These two kinds of orientations can be present in the surfactant molecule usually.Depend on reaction conditions (for example alkali or acid catalysis), usually mainly oxyalkyl units (for example propoxy-) is introduced in one of above-mentioned orientation.In addition, after the oxybutylene polymerization for example, described butoxy can be straight chain or branching.Preferred described butoxy is branching.
The used straight chained alkyl alkoxyl group sulfonate of the present invention can prepare in the known mode of those skilled in the art in principle.Usually use alkoxylating catalyst to make pure R
1-OH and oxyalkylene (for example ethylene oxide, propylene oxide, oxybutylene) reaction.Described synthetic also can be initial by having an alkyl alcohol mixture that certain alkyl chain length distributes, wherein usually mention maximum chain length distribution (C for example
24/
26Alkyl alcohol or C
16/
18Alkyl alcohol).The method of implementing alkoxylation is that those skilled in the art are known.Those skilled in the art are known that equally the molecular weight distribution of alcoxylates can be subjected to reaction conditions, particularly the impact of catalyzer selection.Subsequently, can make alcohol alcoxylates and for example thionyl chloride (for example in chlorobenzene) react to obtain the muriate product.Subsequently, can react with for example S-WAT, this obtains required sulfonate.
Number m, n, p refer to the mean value of existing alkoxyl group in the described alkyl alkoxy sulfonate (for example butoxy, propoxy-, oxyethyl group), and wherein this mean value is not to be necessary for natural number, but also can be arbitrarily required rational number.
The sum of oxyalkyl units (m+n+p) is in particular 1-20, the number of preferred 1-10.In preferred embodiments, m=0, n=0, and p is 1-20, preferred 1-10, the number of preferred 1-8.In another preferred embodiment, m=0, n are 1-10, and the preferably number of 1-8, and p is 1-10, the number of preferred 1-8.In another preferred embodiment, m is the number of 1-8, and n is the number of 1-8, and n is the number of 1-8.
In another embodiment of the present invention, use formula (I) the straight chained alkyl alkoxyl group sulfonate that comprises than the more ethoxy unit in propoxy-unit, wherein the propoxy-unit is in particular 0-1 with the ratio (n/p) of ethoxy unit.
In one embodiment of the invention, use the straight chained alkyl alkoxyl group sulfonate of at least a formula (I), wherein R
1Individual for having 20-30, the straight chained alkyl of preferred 22-28 carbon atom, and wherein m+n+p is 1-20, the number of preferred 1-10.
In one embodiment, can use at least a aforesaid formula (I) straight chained alkyl alkoxyl group sulfonate, wherein R
1Individual for having 20-30, the linear alkyl chain of preferred 22-28 carbon atom, m=0, n=0, and p is the number of 2-8.
In one embodiment, can use at least a aforesaid formula (I) straight chained alkyl alkoxyl group sulfonate, wherein R
1Individual for having 20-30, the linear alkyl chain of preferred 22-28 carbon atom, m=0, n are the number of 2-8, and p is the number of 2-8.
Preferably, the present invention relates to comprise the aqueous composition of at least a aforesaid formula (I) straight chained alkyl alkoxyl group sulfonate for generation of the purposes of aforesaid foam.
In embodiments, the aqueous composition that the present invention relates to comprise at least a formula (I) straight chained alkyl alkoxyl group sulfonate is used at 100-250 ℃, preferred 150-250 ℃, preferred 180-250 ℃, more preferably produce the purposes of foam under the pressure of 200-250 ℃ temperature and 1-100 bar.
Especially, the used aqueous composition of the present invention can comprise following material (or be comprised of following material):
10-99.99% (w/w), the water of preferred 90-99.99% (w/w),
0.01-10% (w/w), preferred 0.01-5% (w/w), more preferably 0.01-1% (w/w), more preferably at least a aforesaid formula (I) the straight chained alkyl alkoxyl group sulfonate of 0.05-0.5% (w/w),
At least a other additives of 0-25% (w/w).
Unless definition is hereinafter arranged in addition, otherwise all amount % (w/w) that give all relate to whole compositions.
Described composition is usually by 90-99% (w/w) water, and at least a alkyl alkoxy sulfonate of 0.01-10% (w/w) consists of.Can add other additives (at the most 25%) in the said composition.
Unless otherwise defined, otherwise give all the amount % (w/w) all relate to whole aqueous compositions.
In embodiments, above-mentioned aqueous composition comprises 0.01-10% (w/w), preferred 0.01-5% (w/w), more preferably 0.01-1% (w/w), more preferably at least a aforesaid formula (I) the straight chained alkyl alkoxyl group sulfonate of 0.05-0.5% (w/w).
In one embodiment, above-mentioned aqueous composition can comprise the mixture of at least two kinds of aforesaid formulas (I) straight chained alkyl alkoxyl group sulfonate.
Other additives of the aqueous composition that the present invention is used can for example be selected from:
I) water-soluble inorganic salt (for example sodium-chlor, Repone K, magnesium chloride);
Ii) cosolvent, it is selected from alcohol, ethoxylated alcohol, for example butyldiglycol, ether and ester;
Iii) other tensio-active agents (cosurfactant);
Iv) thickening material, for example stratiform silicon-dioxide.
Especially, the amount of other additives is 0.01-25% (w/w), preferred 0.01-10% (w/w), preferred 0.1-5% (w/w).
In embodiments of the invention, above-mentioned aqueous composition comprises its amount and is 0.01-25% (w/w), and at least a water-soluble inorganic salt of preferred 0.01-10% (w/w) is as other additives.Especially, described water-soluble inorganic salt is selected from sodium-chlor, Repone K and magnesium chloride.For the present invention, " water-soluble cpds " means the compound that under standard temperature (for example 25 ℃) solubleness in water is higher than 10g/l.
Especially, above-mentioned aqueous composition can further comprise cosolvent, and it can be selected from polar water-miscible solvent.Especially, described cosolvent can be selected from alcohol, particular methanol, ethanol, Virahol, butanols, butyl one glycol, butyldiglycol, butyl triglycol; Ether, preferred dme, diethyl ether, dipropyl ether, methyl ethyl ether, methyl-propyl ether, ethyl propyl ether; Glycol ethers and ester, ethyl acetate, n-butyl acetate, propylidene base diol ester.Suitable cosolvent also can be mixture or the combination of above-mentioned solvent.
In embodiments of the invention, above-mentioned aqueous composition can comprise 0.01-25% (w/w), preferred 0.01-10% (w/w), and the preferred at least a cosolvent of alcohol, ether and ester that is selected from of 0.1-5% (w/w) is as other additives.
Above-mentioned aqueous composition can further comprise the tensio-active agent (cosurfactant) except the described straight chained alkyl alkoxyl group of formula (I) sulfonate as other additives, this cosurfactant is compared with the described straight chained alkyl alkoxyl group of formula (I) sulfonate especially, demonstrates more hydrophilic character.Especially, described cosurfactant can be at least a alkylsulfonate (cumene sulfonate for example that is selected from, dodecane sulfonate), alkyl-sulphate (dodecyl sulfate for example, myristyl vitriol, palmityl vitriol, stearin-based sulfate), alkylaryl sulphonate, alkyl aryl sulfate, alkyl alkoxy sulfonate, alkyl alkoxy sulfate, alkylaryl alkoxyl group sulfonate, the alkylaryl alkoxy sulfate, alcohol ethoxylate, alkyl phosphate, the alkyl acid phosphate alkoxy ester, the tensio-active agent of alkyl polyglucoside and sorbitan fatty acid ester.Except than the more hydrophilic cosurfactant of described straight chained alkyl alkoxyl group sulfonate, more not hydrophilic tensio-active agent also can be the part of described aqueous composition, such as saturated or unsaturated C
5-20Alcohol (for example amylalcohol, hexanol, decyl alcohol, dodecanol, oleyl alcohol, C
16/18Alcohol), has C
8-C
18The salt (for example stearic sodium salt) of the alkylamine of alkyl chain length, lipid acid (for example oleic acid and stearic acid) and lipid acid.Especially, above-mentioned cosurfactant comprises C
8-20Alkyl chain.Above-mentioned tensio-active agent can be preferably with for example its basic metal or the interpolation of alkaline-earth metal salt form of its salt.
In preferred embodiments, the used aqueous composition of the present invention comprises at least a cosurfactant of following material that is selected from as other additives: C
8-20Alkylsulfonate, C
8-20Alkyl-sulphate, C
8-20Alkylaryl sulphonate, C
8-20Alkyl aryl sulfate, C
8-20Alkyl alkoxy sulfonate, C
8-20Alkyl alkoxy sulfate, C
8-20Alkylaryl alkoxyl group sulfonate, C
8-20Alkylaryl alkoxy sulfate, more preferably at least a C
8-20Alkylaryl sulphonate or C
8-20Alkylaryl alkoxyl group sulfonate.
Especially, the used aqueous composition of the present invention comprises its amount and is 0.01-10% (w/w), preferred 0.01-1% (w/w), at least a cosurfactant of preferred 0.1-0.9% (w/w).
In another embodiment, described aqueous composition comprises the alkyl alkoxy sulfonate of described formula (I) as unique tensio-active agent.
In preferred embodiments, the present invention relates to such use, wherein said foam is used for washing and cleaning, forms microemulsion, and Metal Production or oil recovery are used.
In addition, the present invention relates to a kind of generation foam, the particularly method of high-temperature stable foam, it comprises the steps:
A) by preparing aqueous composition in straight chained alkyl alkoxyl group sulfonate adding (for example being dissolved in) water with at least a formula (I):
Wherein:
R
1For having 14-36 carbon atom, preferably 20-30, preferred 22-30, preferred 22-28 is individual, more preferably the linear alkyl chain of 24-28 carbon atom;
R
aBe hydrogen or methyl separately independently for n oxyalkyl units;
R
bBe hydrogen or methyl separately independently for n oxyalkyl units;
Condition is for n oxyalkyl units separately, R
aOr R
bIn at least one is not hydrogen;
M is 0-10, preferred 0-8, the number of preferred 1-8;
N is 0-10, the number of preferred 1-8;
P is 0-20, the number of preferred 1-8;
Condition is m+n+p〉0;
X is selected from Na
+, K
+, Mg
2+And NH
4 +,
Y is 1 or 2 integer;
B) optional at least a other additives are added in the described aqueous composition;
C) described aqueous composition (if at step a or suitablely obtain in step b) is contacted with gas;
Wherein said method preferred 150-250 ℃, usually at 180-250 ℃, is more preferably carried out under 200-250 ℃ temperature at 100-250 ℃.
At least one step of aforesaid method, preferred steps c preferred 150-250 ℃, usually at 180-250 ℃, more preferably carries out under 200-250 ℃ temperature usually at 100-250 ℃.
In another embodiment, step c) can under 15-30 ℃ temperature, carry out, then described aqueous composition (respectively, described foam) be risen to 100-250 ℃, preferred 150-250 ℃, 180-250 ℃ usually, more preferably 200-250 ℃ temperature.
In a preferred embodiment of the invention, described aqueous composition (if step a) in or suitable for step b) in obtain) carry out in by the described aqueous composition with gas inject with the contacting of gas (step c).
Aforesaid method, preferred steps c can implement under the pressure of 1-100 bar especially.
Preferably, the method for described generation foam preferred 150-250 ℃, is carried out under 180-250 ℃ temperature usually at 100-250 ℃.More preferably, described aqueous composition contacts (step c) at 100-250 ℃ with gas, preferred 150-250 ℃, usually at 180-250 ℃, more preferably carries out under 200-250 ℃ temperature.
Described other additives can be selected from water-soluble inorganic salt and cosolvent, cosurfactant and thickening material.With regard to used other additives of the inventive method, also applicable and straight chained alkyl alkoxyl group sulfonate are for generation of the relevant above-mentioned preferred embodiment of the purposes of foam.
Used gas is preferably selected from nitrogen, carbonic acid gas, steam, water vapour, Sweet natural gas, methane, ethane, propane, fuel gas, air and composition thereof among the step c, is preferably selected from air, steam, carbonic acid gas, nitrogen and composition thereof.Described gas more preferably is selected from air, steam, carbonic acid gas, nitrogen and composition thereof.
Especially, can preferably the method for generation foam of the present invention will just be used for for generation of the described at least a formula of the purposes of foam (I) straight chained alkyl alkoxyl group sulfonate above.
Especially, above can be used in the method for generation foam of the present invention with regard to the preferred embodiment of the described aqueous composition of purposes of formula (I) straight chained alkyl alkoxyl group sulfonate in producing foam.
Preferably, the present invention relates to a kind of method of above-mentioned generation foam, wherein at least a cosurfactant of 0.01-10% (w/w) is added in the described aqueous composition as other additives.Suitable cosurfactant as mentioned above.
In embodiments, the present invention relates to a kind of method that produces foam, it comprises the steps:
A) by preparing aqueous composition at least a formula (I) straight chained alkyl alkoxyl group sulfonate adding (for example being dissolved in) water with 0.01-10% (w/w):
Wherein:
R
1For having 20-30, preferred 22-30, preferred 22-28 is individual, more preferably the linear alkyl chain of 24-28 carbon atom;
R
aBe hydrogen or methyl separately independently for n oxyalkyl units;
R
bBe hydrogen or methyl separately independently for n oxyalkyl units;
Condition is for n oxyalkyl units separately, at least one R
aOr R
bBe not hydrogen;
M is 0-10, preferred 0-8, the number of preferred 1-8;
N is 0-10, the number of preferred 1-8;
P is 0-20, the number of preferred 1-8;
Condition is m+n+p〉0;
X is selected from Na
+, K
+, Mg
2+And NH
4 +,
Y is 1 or 2 integer;
B) its amount is 0.01-10% (w/w), preferred 0.01-1% (w/w), at least a cosurfactant of preferred 0.1-0.9% (w/w) adds in the described aqueous composition;
C) at 100-250 ℃, preferred 150-250 ℃, preferred 180-250 ℃, more preferably under 200-250 ℃ the temperature and preferably under the pressure of 1-100 bar, in the described aqueous composition of gas inject (at step a, in step b, obtaining if appropriate).
In another aspect, the present invention relates to a kind of aqueous composition that bubbles, it comprises:
10-99.99% (w/w), the water of preferred 90-99.9% (w/w),
At least a formula (I) the straight chained alkyl alkoxyl group sulfonate of 0.01-10% (w/w):
Wherein:
R
1For having the 20-36 of containing, preferred 22-30, preferred 24-30 is individual, and preferred 25-30, the linear alkyl chain of preferred 25-28 carbon atom;
R
aBe hydrogen or methyl separately independently for n oxyalkyl units;
R
bBe hydrogen or methyl separately independently for n oxyalkyl units;
Condition is for n oxyalkyl units separately, at least one R
aOr R
bBe not hydrogen;
M is 0-10, preferred 0-8, the number of preferred 1-8;
N is 0-10, the number of preferred 1-8;
P is 0-20, the number of preferred 1-8;
Condition is m+n+p〉0;
X is selected from Na
+, K
+, Mg
2+And NH
4 +,
Y is 1 or 2 integer;
At least a other additives of 0-25% (w/w).
Described composition is made of 90-99% (w/w) water, at least a alkyl alkoxy sulfonate of 0.01-10% (w/w) usually.Can add other additives (at the most 25%) in the said composition.
Unless otherwise defined, otherwise give all the amount % (w/w) all relate to whole aqueous compositions.
Preferably, the above-mentioned aqueous composition that bubbles comprises 0.01-10% (w/w), preferred 0.01-5% (w/w), more preferably 0.01-1% (w/w), more preferably at least a formula (I) the straight chained alkyl alkoxyl group sulfonate of 0.05-0.5% (w/w).
In addition, above just be used at high temperature producing foam aqueous composition the described preferred embodiment of purposes also applicable to the invention described above can foaming aqueous composition.
Further elaborate the present invention by embodiment hereinafter.
Embodiment 1: forming foams 200 ℃ times at the most
Use front and the back side have the autoclave of window, thereby by whipability, foamy structure and the froth stability of pick up camera observation as the temperature and time function.Temperature is regulated by electric heater unit.Use photo and short-sighted frequency to carry out record.Thereby the peak pressure that uses nitrogen to apply 80 bar makes solution keep liquid.Foam produces by the water phase surfactant mixture (50ml) that nitrogen is injected mechanical stirring (1300rpm).The concentration of tensio-active agent is 1g/l.Be that the frit of 2 μ m places the jet pipe end to produce small bubbles with the aperture.After nitrogen injection, stop to stir and detecting froth stability.
Under 200 ℃ differing temps at the most, the time (referring to the y axle of Fig. 1) when record can be observed the first sign of foam collapses.
Fig. 1 has shown the time t (in second) when observing the first foam collapses (y axle) under the temperature T at 120-200 ℃ (in ℃) (x axle), wherein:
Open squares () expression C16/C18-6PO-2EO-SO
3Na,
Black triangle (▲) expression C12 phenol-6PO-2EO-SO
3Na, and
Solid diamond (◆) expression iC17-6PO-2EO-SO
3The Na tensio-active agent.
EO represents ethoxy unit, and PO represents that propoxy-unit and BO represent the butoxy unit.With the alkyl chain of the C description surface promoting agent of numeral, for example C16 means to have the alkyl chain of 16 carbon atoms, and iC17 means to have the iso-alkyl chain of 17 carbon atoms.
Result by Fig. 1 can find out, compares with the different surfaces active agent structures that has almost identical C atomicity in the hydrophobic molecule part, and the performance of linear alkyl chain is very good.Expection branching causes air/water tensio-active agent tap density at the interface to reduce, and this is so that the foam layer unstability.
As seen from Figure 1, comprise C16/C18-6PO-2EO-SO
3The foam of Na is stablized about 400 seconds under 150 ℃, and comprises contrast surface promoting agent C12 phenol-6PO-2EO-SO
3Na and iC17-6PO-2EO-SO
3The foam of Na was caving in after 2 and 5 seconds under 150 ℃ the temperature.Under 120 ℃ temperature, comprise C16/C18-6PO-2EO-SO
3The foam of Na caved in after 500 seconds, comprised C12 phenol-6PO-2EO-SO
3The foam of Na caved in after 35 seconds, and comprised iC17-6PO-2EO-SO
3The foam of Na caved in after 3 seconds.
Embodiment 2: at 250 ℃ of lower foams that form
Under 250 ℃ temperature, sodium salt and the foaming behavior under different Repone K (KCI) concentration with the several straight chain C 24/26 polyethoxye sulfonate of different ethoxy units (EO) compared.Foam is to produce with embodiment 1 described same way as.Froth stability (time before foam begins to cave in) is measured according to the described mode of embodiment.The concentration of tensio-active agent is 1g/l.The results are shown in the table 1.
Table 1: begin to cave at 250 ℃ of lower foams
Result by table 1 can find out that froth stability depends on the quantity (EO number) of ethoxy unit.Add salt and can protect the electric charge of anion sulfoacid root, this causes piling up more closely at the interface in air/water.It is lower to be expected at the salt existence, and the froth stability of foam is improved.
At C22-2EO-SO
3In the situation of Na, find that froth stability continues to raise along with the increase of KCl amount, and reach the maximum of about 100g/l.Yet, at certain situation such as C22-5EO-SO
3Na or C24/26-4EO-SO
3Under the Na, find that froth stability experiences maximum value along with the increase of salt amount.This effect may be relevant with salting-out effect, and this depends on that EO unit, alkyl chain length and potential coordination phenomenon are (at C22-5EO-SO
3In the situation of Na).
Embodiment 3: alkyl chain length is on the impact of froth stability
As described in Example 2, measure the froth stability of the foam that comprises the alkyl alkoxy sulfonate with different alkyl chain lengths under 200-250 ℃ of temperature, wherein the concentration of tensio-active agent is 1g/l.The results are summarized in the table 2.
Table 2: begin to cave at 200 ℃ and 250 ℃ of lower foams
Find that froth stability is along with the alkyl chain length of tensio-active agent increases and improves.
Embodiment 4: the froth stability of using surfactant mixture
Under 200-250 ℃ of temperature, as described in Example 2, measure in varing proportions and alkylaryl alkoxyl group sulfonate (C12 phenol-6PO-2EO-SO
3Na) C of combination
24/26-4EO-SO
3The froth stability of Na, wherein the total concn of tensio-active agent is 1g/l.The weight ratio of tensio-active agent is 9:1 and 8:2.The results are summarized in the table 3.
Table 3: foam begins to cave under 200 ℃ and 250 ℃
The result shows that the foam stabilization effect also can contain alkyl alkoxy sulfonate and at least a surfactant mixture acquisition with other tensio-active agents of shorter hydrophobic chain by use.
Embodiment 5: the impact of additive
Under 200-250 ℃ of temperature, as described in Example 2, measure the C22-2EO-SO with stratiform silica clays mineral and salt combination
3The froth stability of Na tensio-active agent, wherein the concentration of tensio-active agent is 1g/l.With at the T=200 ℃ of composition relevant with T=250 ℃ of lower froth stability with the results are summarized in the table 4.As stratiform silicon-dioxide, Repone K (KCl) is as salt with Laponite RD.
Table 4: foam begins to cave under 200 ℃ and 250 ℃
But thereby the water between the clay mineral thickening foam layer reduces drainage and improves froth stability.Clay mineral (Laponite RD) demonstrates the foam stabilization effect.
Embodiment 6: chemical stability
Under the pressure of 250 ℃ and 62 bar, store 12 hours 1g/l C22-2EO-SO
3The Na aqueous solution is on not impact of foaming behavior.
Claims (14)
1. the straight chained alkyl alkoxyl group sulfonate of at least a formula (I) is used for producing the purposes of foam under the temperature of 100-250 ° of C:
Wherein:
R
1For having the linear alkyl chain of 14-36 carbon atom;
R
aBe hydrogen or methyl separately independently for n oxyalkyl units;
R
bBe hydrogen or methyl separately independently for n oxyalkyl units;
Condition is for n oxyalkyl units separately, at least one R
aOr R
bBe not hydrogen;
M is the number of 0-10;
N is the number of 0-10;
P is the number of 0-20;
Condition is m+n+p〉0;
X is selected from Na
+, K
+, Mg
2+And NH
4 +,
Y is 1 or 2 integer.
2. according to claim 1 purposes, wherein R
1For having the linear alkyl chain of 20-30 carbon atom.
3. according to claim 1 and 2 purposes wherein will comprise the aqueous composition of straight chained alkyl alkoxyl group sulfonate of at least a formula (I) for generation of foam.
4. each purposes according to claim 1-3, wherein use the aqueous composition that comprises following component:
The water of 10-99.99% (w/w),
The straight chained alkyl alkoxyl group sulfonate of at least a formula (I) of 0.01-10% (w/w),
At least a other additives of 0-25% (w/w).
5. at least a water-soluble inorganic salt that it is 0.01-25% (w/w) that each purposes according to claim 1-4, wherein said aqueous composition comprise its amount is as other additives.
6. each purposes according to claim 1-5, wherein said aqueous composition comprise at least a cosolvent of alcohol, ether and ester that is selected from of 0.01-25% (w/w) as other additives.
7. each purposes according to claim 1-6, the aqueous composition that wherein will comprise the straight chained alkyl alkoxyl group sulfonate of at least a formula (I) are used for producing foam under the pressure of 150-250 ℃ temperature and 1-100 bar.
8. each purposes according to claim 1-7, wherein said foam are used for washing and cleaning, formation microemulsion, Metal Production or recover the oil and use.
9. produce the method for foam, it comprises the steps:
A) be added to the water by the straight chained alkyl alkoxyl group sulfonate with at least a formula (I) and prepare aqueous composition:
Wherein:
R
1For having the linear alkyl chain of 14-36 carbon atom;
R
aBe hydrogen or methyl separately independently for n oxyalkyl units;
R
bBe hydrogen or methyl separately independently for n oxyalkyl units;
Condition is for n oxyalkyl units separately, at least one R
aOr R
bBe not hydrogen;
M is the number of 0-1;
N is the number of 0-10;
P is the number of 0-20;
Condition is m+n+p〉0;
X is selected from Na
+, K
+, Mg
2+And NH
4 +,
Y is 1 or 2 integer;
B) optional at least a other additives are added in the described aqueous composition;
C) described aqueous composition is contacted with gas;
Wherein said method is carried out under 100-250 ℃ temperature.
10. according to claim 9 method, wherein said aqueous composition contacts (step c) by carrying out in the described aqueous composition of gas inject with gas.
11. according to claim 9 or 10 method, wherein used gas is selected from nitrogen, carbonic acid gas, steam, water vapour, Sweet natural gas, methane, ethane, propane, fuel gas, air and composition thereof among the step c.
12. each method according to claim 9-11, wherein at least a cosurfactant with 0.01-10% (w/w) adds in the described aqueous composition as other additives.
13. each method according to claim 9-12, wherein said aqueous composition carries out with contacting under 150-250 ℃ temperature of gas.
14. the aqueous composition that can bubble, it comprises:
The water of 10-99.99% (w/w),
The straight chained alkyl alkoxyl group sulfonate of at least a formula (I) of 0.01-10% (w/w),
Wherein:
R
1For having the linear alkyl chain of 20-36 carbon atom;
R
aBe hydrogen or methyl separately independently for n oxyalkyl units;
R
bBe hydrogen or methyl separately independently for n oxyalkyl units;
Condition is for n oxyalkyl units separately, at least one R
aOr R
bBe not hydrogen;
M is the number of 0-10;
N is the number of 0-10;
P is the number of 0-20;
Condition is m+n+p〉0;
X is selected from Na
+, K
+, Mg
2+And NH
4 +,
Y is 1 or 2 integer;
One or more other additives of 0-25% (w/w).
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP111557260 | 2011-02-24 | ||
| EP11155726.0 | 2011-02-24 | ||
| EP11155726 | 2011-02-24 | ||
| PCT/EP2012/053063 WO2012113861A1 (en) | 2011-02-24 | 2012-02-23 | Compositions comprising alkylalkoxysulfonates for the production of high temperature stable foams |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103380208A true CN103380208A (en) | 2013-10-30 |
| CN103380208B CN103380208B (en) | 2015-12-09 |
Family
ID=45688526
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|---|---|---|---|
| CN201280009626.8A Expired - Fee Related CN103380208B (en) | 2011-02-24 | 2012-02-23 | For generation of the composition comprising alkyl alkoxy sulfonate of high-temperature stable foam |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP2678414A1 (en) |
| CN (1) | CN103380208B (en) |
| AU (1) | AU2012219554A1 (en) |
| BR (1) | BR112013021063A2 (en) |
| CA (1) | CA2827323A1 (en) |
| EA (1) | EA201391214A1 (en) |
| MX (1) | MX2013009598A (en) |
| WO (1) | WO2012113861A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104857662A (en) * | 2015-05-26 | 2015-08-26 | 厦门安港消防科技有限公司 | Foam extinguishing agent |
| CN106590576A (en) * | 2015-10-20 | 2017-04-26 | 中国石油化工股份有限公司 | Steam foam compound flooding composition and preparation method thereof |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY165866A (en) | 2011-03-18 | 2018-05-18 | Basf Se | Method for manufacturing integrated circuit devices, optical devices, micromachines and mechanical precision devices having patterned material layers with line-space dimensions of 50 nm and less |
| CA2913048A1 (en) * | 2013-05-31 | 2014-12-04 | Dow Global Technologies Llc | Enhanced oil recovery method employing a biodegradable brine tolerant foam-forming composition |
| FR3053690B1 (en) * | 2016-07-08 | 2019-12-06 | Rhodia Operations | STABILIZATION OF FOAMS BY CLAY PARTICLES |
| MX2020006887A (en) * | 2018-01-03 | 2020-09-07 | Unilever Ip Holdings B V | Method for demonstrating cleansing efficacy. |
| CN115058238B (en) * | 2022-06-20 | 2024-02-06 | 中国石油大学(华东) | Surface modified nanoparticle high-temperature foam stabilizer and preparation method and application thereof |
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| CN101351539A (en) * | 2006-01-03 | 2009-01-21 | 巴斯夫欧洲公司 | Powder or granulate based on glutamic-n,n,diacetic acid and its salts |
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| CA1096153A (en) * | 1978-02-13 | 1981-02-24 | Russell D. Shupe | Surfactant oil recovery process usable in high temperature, high salinity formations |
| US4201678A (en) | 1978-03-17 | 1980-05-06 | Union Oil Company Of California | Foam drilling and workover in high temperature wells |
| US4502538A (en) * | 1984-01-09 | 1985-03-05 | Shell Oil Company | Polyalkoxy sulfonate, CO2 and brine drive process for oil recovery |
| US4577688A (en) * | 1984-02-03 | 1986-03-25 | Texaco Inc. | Injection of steam foaming agents into producing wells |
| DE3622439A1 (en) | 1986-07-04 | 1988-01-07 | Henkel Kgaa | HAIR TREATMENT |
| US5193618A (en) | 1991-09-12 | 1993-03-16 | Chevron Research And Technology Company | Multivalent ion tolerant steam-foaming surfactant composition for use in enhanced oil recovery operations |
| US5358045A (en) | 1993-02-12 | 1994-10-25 | Chevron Research And Technology Company, A Division Of Chevron U.S.A. Inc. | Enhanced oil recovery method employing a high temperature brine tolerant foam-forming composition |
| US5996693A (en) * | 1998-09-15 | 1999-12-07 | Halliburton Energy Services, Inc. | Methods and compositions for cementing pipe in well bores |
| US9018145B2 (en) | 2003-12-23 | 2015-04-28 | Lubrizol Oilfield Solutions, Inc. | Foamer composition and methods for making and using same |
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-
2012
- 2012-02-23 MX MX2013009598A patent/MX2013009598A/en unknown
- 2012-02-23 CN CN201280009626.8A patent/CN103380208B/en not_active Expired - Fee Related
- 2012-02-23 WO PCT/EP2012/053063 patent/WO2012113861A1/en active Application Filing
- 2012-02-23 AU AU2012219554A patent/AU2012219554A1/en not_active Abandoned
- 2012-02-23 CA CA2827323A patent/CA2827323A1/en not_active Abandoned
- 2012-02-23 EA EA201391214A patent/EA201391214A1/en unknown
- 2012-02-23 BR BR112013021063A patent/BR112013021063A2/en not_active IP Right Cessation
- 2012-02-23 EP EP12704847.8A patent/EP2678414A1/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101351539A (en) * | 2006-01-03 | 2009-01-21 | 巴斯夫欧洲公司 | Powder or granulate based on glutamic-n,n,diacetic acid and its salts |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104857662A (en) * | 2015-05-26 | 2015-08-26 | 厦门安港消防科技有限公司 | Foam extinguishing agent |
| CN106590576A (en) * | 2015-10-20 | 2017-04-26 | 中国石油化工股份有限公司 | Steam foam compound flooding composition and preparation method thereof |
| CN106590576B (en) * | 2015-10-20 | 2019-04-12 | 中国石油化工股份有限公司 | Steam combination flooding foam compositions and preparation method |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103380208B (en) | 2015-12-09 |
| EP2678414A1 (en) | 2014-01-01 |
| CA2827323A1 (en) | 2012-08-30 |
| WO2012113861A1 (en) | 2012-08-30 |
| BR112013021063A2 (en) | 2019-09-24 |
| AU2012219554A1 (en) | 2013-08-29 |
| MX2013009598A (en) | 2013-11-04 |
| EA201391214A1 (en) | 2014-02-28 |
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