CA3038464A1 - Emulsions ou micro-emulsions comprenant un agent de surface anionique, un solvant et de l'eau, et procedes relatifs a leur utilisation dans un puits de petrole et/ou un puits de gaz - Google Patents
Emulsions ou micro-emulsions comprenant un agent de surface anionique, un solvant et de l'eau, et procedes relatifs a leur utilisation dans un puits de petrole et/ou un puits de gaz Download PDFInfo
- Publication number
- CA3038464A1 CA3038464A1 CA3038464A CA3038464A CA3038464A1 CA 3038464 A1 CA3038464 A1 CA 3038464A1 CA 3038464 A CA3038464 A CA 3038464A CA 3038464 A CA3038464 A CA 3038464A CA 3038464 A1 CA3038464 A1 CA 3038464A1
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- CA
- Canada
- Prior art keywords
- microemulsion
- emulsion
- composition
- versus
- total
- 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
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- 239000004530 micro-emulsion Substances 0.000 title claims abstract description 607
- 239000000839 emulsion Substances 0.000 title claims abstract description 478
- 238000000034 method Methods 0.000 title claims abstract description 350
- 239000002904 solvent Substances 0.000 title claims abstract description 154
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 123
- 239000003945 anionic surfactant Substances 0.000 title description 4
- 239000012530 fluid Substances 0.000 claims abstract description 393
- 239000000203 mixture Substances 0.000 claims abstract description 333
- 239000004094 surface-active agent Substances 0.000 claims abstract description 205
- 239000007789 gas Substances 0.000 claims abstract description 120
- 239000001257 hydrogen Substances 0.000 claims abstract description 102
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 102
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 50
- 125000003118 aryl group Chemical group 0.000 claims abstract description 36
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 25
- 125000002091 cationic group Chemical group 0.000 claims abstract description 14
- 125000000129 anionic group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 160
- 239000003921 oil Substances 0.000 claims description 125
- 125000002015 acyclic group Chemical group 0.000 claims description 118
- 125000004122 cyclic group Chemical group 0.000 claims description 113
- 150000003505 terpenes Chemical class 0.000 claims description 107
- 235000007586 terpenes Nutrition 0.000 claims description 104
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 99
- 238000007710 freezing Methods 0.000 claims description 97
- 230000008014 freezing Effects 0.000 claims description 97
- 239000003795 chemical substances by application Substances 0.000 claims description 94
- 239000000654 additive Substances 0.000 claims description 74
- -1 alkylene glycol Chemical compound 0.000 claims description 67
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
- 230000000638 stimulation Effects 0.000 claims description 59
- 238000005553 drilling Methods 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 239000002253 acid Substances 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 39
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
- 238000006073 displacement reaction Methods 0.000 claims description 35
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 32
- 150000001408 amides Chemical class 0.000 claims description 29
- 150000001412 amines Chemical class 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 22
- 239000008346 aqueous phase Substances 0.000 claims description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
- XMGQYMWWDOXHJM-JTQLQIEISA-N D-limonene Natural products CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 claims description 15
- 239000004927 clay Substances 0.000 claims description 15
- 239000006260 foam Substances 0.000 claims description 15
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 150000007513 acids Chemical class 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical compound C=1C=CC=CC=1C=CC1=C(C=CC=2C=CC=CC=2)C(O)=CC=C1C=CC1=CC=CC=C1 TVFWYUWNQVRQRG-UHFFFAOYSA-N 0.000 claims description 13
- 230000000996 additive effect Effects 0.000 claims description 13
- 238000012856 packing Methods 0.000 claims description 13
- 239000003112 inhibitor Substances 0.000 claims description 12
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Natural products CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 241000207199 Citrus Species 0.000 claims description 10
- 235000020971 citrus fruits Nutrition 0.000 claims description 10
- 239000003381 stabilizer Substances 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 230000008961 swelling Effects 0.000 claims description 8
- 230000007797 corrosion Effects 0.000 claims description 7
- 238000005260 corrosion Methods 0.000 claims description 7
- 229940123973 Oxygen scavenger Drugs 0.000 claims description 6
- 239000003139 biocide Substances 0.000 claims description 6
- 239000000872 buffer Substances 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 239000002455 scale inhibitor Substances 0.000 claims description 6
- 239000003595 mist Substances 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 230000003115 biocidal effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000000545 (4R)-limonene group Chemical group 0.000 claims 7
- 125000000396 limonene group Chemical group 0.000 claims 7
- 238000007865 diluting Methods 0.000 claims 4
- 235000019198 oils Nutrition 0.000 description 82
- 230000015572 biosynthetic process Effects 0.000 description 49
- 238000005755 formation reaction Methods 0.000 description 49
- 150000001875 compounds Chemical class 0.000 description 41
- 125000004432 carbon atom Chemical group C* 0.000 description 36
- 230000001965 increasing effect Effects 0.000 description 25
- 229930195733 hydrocarbon Natural products 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 24
- 238000011084 recovery Methods 0.000 description 24
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 23
- 230000008901 benefit Effects 0.000 description 23
- 150000002430 hydrocarbons Chemical class 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 19
- 150000001335 aliphatic alkanes Chemical class 0.000 description 19
- 206010017076 Fracture Diseases 0.000 description 18
- 239000000463 material Substances 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- 230000008569 process Effects 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000004576 sand Substances 0.000 description 15
- 208000010392 Bone Fractures Diseases 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 150000001336 alkenes Chemical class 0.000 description 13
- 239000010779 crude oil Substances 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- 239000004568 cement Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 230000035699 permeability Effects 0.000 description 11
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- 239000001569 carbon dioxide Substances 0.000 description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 238000005213 imbibition Methods 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 7
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical class CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 229920001400 block copolymer Polymers 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 5
- ROKSAUSPJGWCSM-UHFFFAOYSA-N 2-(7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)ethanol Chemical compound C1C2C(C)(C)C1CC=C2CCO ROKSAUSPJGWCSM-UHFFFAOYSA-N 0.000 description 5
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical class CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- 229960005233 cineole Drugs 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- NMRPBPVERJPACX-UHFFFAOYSA-N octan-3-ol Chemical compound CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical class CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical class CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 4
- WGECXQBGLLYSFP-UHFFFAOYSA-N 2,3-dimethylpentane Chemical compound CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical class CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 description 4
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical class CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical class CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical class CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 description 4
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical class CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical class CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229930003658 monoterpene Natural products 0.000 description 4
- 150000002773 monoterpene derivatives Chemical class 0.000 description 4
- 235000002577 monoterpenes Nutrition 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- MEKULSCNDYBJBL-UHFFFAOYSA-N n-decyl-n-methyldodecan-1-amine Chemical class CCCCCCCCCCCCN(C)CCCCCCCCCC MEKULSCNDYBJBL-UHFFFAOYSA-N 0.000 description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical class CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- WOFPPJOZXUTRAU-UHFFFAOYSA-N octan-4-ol Chemical compound CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- BEKZXQKGTDVSKX-UHFFFAOYSA-N propyl hexadecanoate Chemical class CCCCCCCCCCCCCCCC(=O)OCCC BEKZXQKGTDVSKX-UHFFFAOYSA-N 0.000 description 4
- DEDZSLCZHWTGOR-UHFFFAOYSA-N propylcyclohexane Chemical compound CCCC1CCCCC1 DEDZSLCZHWTGOR-UHFFFAOYSA-N 0.000 description 4
- 239000011435 rock Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 3
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 3
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 3
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- FLTJDUOFAQWHDF-UHFFFAOYSA-N 2,2-dimethylhexane Chemical compound CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 3
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical class CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 3
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,3-dimethylpentane Natural products CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 3
- AEXMKKGTQYQZCS-UHFFFAOYSA-N 3,3-dimethylpentane Chemical compound CCC(C)(C)CC AEXMKKGTQYQZCS-UHFFFAOYSA-N 0.000 description 3
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005792 Geraniol Substances 0.000 description 3
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical class CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical compound CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 description 3
- SBOKAKRQSCBWOU-UHFFFAOYSA-N N-methyl-N-octylhexadecan-1-amine Chemical class CCCCCCCCCCCCCCCCN(C)CCCCCCCC SBOKAKRQSCBWOU-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 208000013201 Stress fracture Diseases 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000002280 amphoteric surfactant Substances 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
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- MWVPQZRIWVPJCA-UHFFFAOYSA-N propylcyclopropane Chemical compound CCCC1CC1 MWVPQZRIWVPJCA-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000246 remedial effect Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 125000003003 spiro group Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229930006978 terpinene Natural products 0.000 description 1
- 150000003507 terpinene derivatives Chemical class 0.000 description 1
- 150000003508 terpinolene derivatives Chemical class 0.000 description 1
- YIEDHPBKGZGLIK-UHFFFAOYSA-L tetrakis(hydroxymethyl)phosphanium;sulfate Chemical compound [O-]S([O-])(=O)=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO YIEDHPBKGZGLIK-UHFFFAOYSA-L 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- AKUNSPZHHSNFFX-UHFFFAOYSA-M tributyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC AKUNSPZHHSNFFX-UHFFFAOYSA-M 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical class CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- BNJRHNHQYFVXTP-UHFFFAOYSA-N undecyl undecanoate Chemical class CCCCCCCCCCCOC(=O)CCCCCCCCCC BNJRHNHQYFVXTP-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003180 well treatment fluid Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/66—Compositions based on water or polar solvents
- C09K8/68—Compositions based on water or polar solvents containing organic compounds
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B28/00—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements
- C04B28/02—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements containing hydraulic cements other than calcium sulfates
-
- 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
- C09K8/03—Specific additives for general use in well-drilling compositions
- C09K8/035—Organic additives
-
- 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
- C09K8/04—Aqueous well-drilling compositions
- C09K8/26—Oil-in-water emulsions
-
- 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
- C09K8/42—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells
- C09K8/46—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells containing inorganic binders, e.g. Portland cement
- C09K8/467—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells containing inorganic binders, e.g. Portland cement containing additives for specific purposes
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- Ceramic Engineering (AREA)
- Structural Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Colloid Chemistry (AREA)
- Detergent Compositions (AREA)
- Lubricants (AREA)
Abstract
Il est décrit une composition et une méthode servant à traiter un puits de pétrole et/ou de gaz. La composition en question comprend un fluide ainsi quune émulsion ou une microémulsion comportant de leau, un solvant et un agent de surface ayant une structure de la Formule II :
Applications Claiming Priority (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/829,495 US9428683B2 (en) | 2013-03-14 | 2013-03-14 | Methods and compositions for stimulating the production of hydrocarbons from subterranean formations |
US13/829,434 | 2013-03-14 | ||
US13/829,495 | 2013-03-14 | ||
US13/829,434 US9068108B2 (en) | 2013-03-14 | 2013-03-14 | Methods and compositions for stimulating the production of hydrocarbons from subterranean formations |
US13/918,155 US9321955B2 (en) | 2013-06-14 | 2013-06-14 | Methods and compositions for stimulating the production of hydrocarbons from subterranean formations |
US13/918,166 | 2013-06-14 | ||
US13/918,155 | 2013-06-14 | ||
US13/918,166 US20140371115A1 (en) | 2013-06-14 | 2013-06-14 | Methods and compositions for stimulating the production of hydrocarbons from subterranean formations |
US201461946176P | 2014-02-28 | 2014-02-28 | |
US61/946,176 | 2014-02-28 | ||
CA2906165A CA2906165C (fr) | 2013-03-14 | 2014-03-14 | Procedes et compositions en vue d'une utilisation dans des puits de petrole et/ou de gaz |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2906165A Division CA2906165C (fr) | 2013-03-14 | 2014-03-14 | Procedes et compositions en vue d'une utilisation dans des puits de petrole et/ou de gaz |
Publications (2)
Publication Number | Publication Date |
---|---|
CA3038464A1 true CA3038464A1 (fr) | 2014-09-25 |
CA3038464C CA3038464C (fr) | 2022-05-17 |
Family
ID=51581418
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA3038464A Active CA3038464C (fr) | 2013-03-14 | 2014-03-14 | Emulsions ou micro-emulsions comprenant un agent de surface anionique, un solvant et de l'eau, et procedes relatifs a leur utilisation dans un puits de petrole et/ou un puits de gaz |
CA2906165A Active CA2906165C (fr) | 2013-03-14 | 2014-03-14 | Procedes et compositions en vue d'une utilisation dans des puits de petrole et/ou de gaz |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2906165A Active CA2906165C (fr) | 2013-03-14 | 2014-03-14 | Procedes et compositions en vue d'une utilisation dans des puits de petrole et/ou de gaz |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP2970753A4 (fr) |
CN (1) | CN105492572A (fr) |
AU (2) | AU2014236272B2 (fr) |
CA (2) | CA3038464C (fr) |
WO (1) | WO2014153102A1 (fr) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20180002590A1 (en) * | 2015-02-25 | 2018-01-04 | Halliburton Energy Services, Inc. | In situ swelling of water-swellable polymers downhole |
JP2017105946A (ja) * | 2015-12-10 | 2017-06-15 | 株式会社クレハ | 重質油用低粘度化剤、重質油の低粘度化方法、及び重質油の回収方法 |
CN106000657B (zh) * | 2016-06-22 | 2018-10-30 | 太原理工大学 | 一种煤泥浮选捕收剂及其制备方法 |
CN110691835B (zh) | 2017-04-06 | 2022-12-09 | 日产化学美国公司 | 耐盐水性二氧化硅溶胶 |
CN107033867B (zh) * | 2017-04-12 | 2020-09-08 | 西安石油大学 | 纳米纤维素与粘弹性表面活性剂复合压裂液及其制备方法及其应用 |
JP2021006595A (ja) | 2017-09-13 | 2021-01-21 | 日産化学株式会社 | 原油回収用薬液 |
US10801310B2 (en) | 2017-09-26 | 2020-10-13 | Nissan Chemcial America Corporation | Using gases and hydrocarbon recovery fluids containing nanoparticles to enhance hydrocarbon recovery |
MX2020004470A (es) | 2017-11-03 | 2020-09-03 | Nissan Chemical America Corp | Uso de dispersiones de nanoparticulas de dioxido de silicio resistentes a la salmuera para mejorar la recuperacion de petroleo. |
MX2021005001A (es) | 2018-11-02 | 2021-06-15 | Nissan Chemical America Corp | Recuperacion de petroleo mejorada utilizando liquidos de tratamiento que comprenden silice coloidal con un apuntalante. |
CN112302588A (zh) * | 2019-07-15 | 2021-02-02 | 中国石油化工股份有限公司 | 采用咪唑啉化合物降低co2驱最小混相压力的方法 |
US20210355369A1 (en) * | 2020-05-13 | 2021-11-18 | Saudi Arabian Oil Company | Enhancing foam rheological properties using water-soluble thickener |
CN114381282B (zh) * | 2021-12-17 | 2024-05-28 | 中国石油大学(华东) | 表面活性剂及其制备方法、微乳液封堵剂及其制备方法和水基钻井液 |
CN114320292B (zh) * | 2022-01-07 | 2024-03-08 | 辽宁工程技术大学 | 一种基于溶液改性作用的煤层冲击地压防治方法 |
CN115288647B (zh) * | 2022-07-22 | 2023-05-19 | 捷贝通石油技术集团股份有限公司 | 一种用于提高油井采收率的复合扩容方法 |
US20240159131A1 (en) * | 2022-11-01 | 2024-05-16 | Baker Hughes Oilfield Operations Llc | Method of Enhancing Foam Stability for Stimulation of Low Pressure Reservoirs |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4005020A (en) * | 1973-07-19 | 1977-01-25 | Petrolite Corporation | Paraffin removing compositions |
US4207193A (en) * | 1978-03-24 | 1980-06-10 | Halliburton Company | Methods and compositions for removing asphaltenic and paraffinic containing deposits |
US5567675A (en) * | 1994-02-16 | 1996-10-22 | Buckman Laboratories Of Canada, Ltd. | Application of N,N-dialkylamides to control the formation of emulsions or sludge during drilling or workover of producing oil wells |
GB9915214D0 (en) * | 1999-06-29 | 1999-09-01 | Bp Exploration Operating | Microemulsions |
US7380606B2 (en) * | 2002-03-01 | 2008-06-03 | Cesi Chemical, A Flotek Company | Composition and process for well cleaning |
DE10343390A1 (de) * | 2003-09-19 | 2005-04-14 | Bayer Cropscience Gmbh | Tensid/Lösungsmittelgemische |
US20080248955A1 (en) * | 2003-11-17 | 2008-10-09 | Jeffrey David Fowler | Emulsifiable Concentrates Containing Adjuvants |
AU2009203757A1 (en) * | 2008-01-09 | 2009-07-16 | Akzo Nobel N.V. | Stable emulsion and process for preparing the same |
US20110021386A1 (en) * | 2009-07-27 | 2011-01-27 | Ali Syed A | Microemulsion to improve shale gas production by controlling water imbibition |
AU2011210837B2 (en) * | 2010-01-28 | 2014-06-05 | Board Of Regents, The University Of Texas System | Styrylphenol alkoxylate sulfate as a new surfactant composition for enhanced oil recovery applications |
CN102277152B (zh) * | 2011-05-16 | 2013-03-13 | 陕西科技大学 | 一种酸触发增稠剂及其制备方法 |
CN102618228B (zh) * | 2012-02-23 | 2014-04-16 | 中国石油化工股份有限公司 | 用于碎屑岩油藏水平井的堵剂、制备方法及堵水方法 |
WO2014004968A1 (fr) * | 2012-06-28 | 2014-01-03 | Rhodia Operations | Systèmes de solvants/systèmes tensioactifs respectueux de l'environnement pour fluides de forage |
US10000693B2 (en) * | 2013-03-14 | 2018-06-19 | Flotek Chemistry, Llc | Methods and compositions for use in oil and/or gas wells |
US9464223B2 (en) * | 2013-03-14 | 2016-10-11 | Flotek Chemistry, Llc | Methods and compositions for use in oil and/or gas wells |
-
2014
- 2014-03-14 WO PCT/US2014/029079 patent/WO2014153102A1/fr active Application Filing
- 2014-03-14 CA CA3038464A patent/CA3038464C/fr active Active
- 2014-03-14 CA CA2906165A patent/CA2906165C/fr active Active
- 2014-03-14 CN CN201480026902.0A patent/CN105492572A/zh active Pending
- 2014-03-14 EP EP14768919.4A patent/EP2970753A4/fr not_active Withdrawn
- 2014-03-14 AU AU2014236272A patent/AU2014236272B2/en not_active Ceased
-
2018
- 2018-02-26 AU AU2018201361A patent/AU2018201361B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
CN105492572A (zh) | 2016-04-13 |
EP2970753A4 (fr) | 2017-03-29 |
AU2018201361B2 (en) | 2019-05-16 |
AU2018201361A1 (en) | 2018-03-15 |
WO2014153102A1 (fr) | 2014-09-25 |
CA2906165C (fr) | 2019-04-02 |
AU2014236272A1 (en) | 2015-10-29 |
CA2906165A1 (fr) | 2014-09-25 |
EP2970753A1 (fr) | 2016-01-20 |
AU2014236272B2 (en) | 2017-11-30 |
CA3038464C (fr) | 2022-05-17 |
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Legal Events
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EEER | Examination request |
Effective date: 20190329 |