EP3052579A1 - Polymères séquencés pour le contrôle du filtrat - Google Patents
Polymères séquencés pour le contrôle du filtratInfo
- Publication number
- EP3052579A1 EP3052579A1 EP14780519.6A EP14780519A EP3052579A1 EP 3052579 A1 EP3052579 A1 EP 3052579A1 EP 14780519 A EP14780519 A EP 14780519A EP 3052579 A1 EP3052579 A1 EP 3052579A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- block
- units
- fluid
- particles
- polymer
- 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.)
- Ceased
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 117
- 239000012530 fluid Substances 0.000 claims abstract description 108
- 239000002245 particle Substances 0.000 claims abstract description 83
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 38
- 239000011435 rock Substances 0.000 claims abstract description 19
- 238000002347 injection Methods 0.000 claims abstract description 14
- 239000007924 injection Substances 0.000 claims abstract description 14
- 239000007787 solid Substances 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims description 66
- -1 tetrahydrofurfuryl Chemical group 0.000 claims description 60
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 45
- 230000015572 biosynthetic process Effects 0.000 claims description 31
- 239000004568 cement Substances 0.000 claims description 29
- 239000000706 filtrate Substances 0.000 claims description 21
- 239000003208 petroleum Substances 0.000 claims description 21
- 238000010526 radical polymerization reaction Methods 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 238000005553 drilling Methods 0.000 claims description 9
- 230000002209 hydrophobic effect Effects 0.000 claims description 9
- 239000002002 slurry Substances 0.000 claims description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 4
- 239000011440 grout Substances 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 239000004576 sand Substances 0.000 claims description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
- 239000006229 carbon black Substances 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 3
- DJABNVJZYFGAJE-UHFFFAOYSA-N 1-ethenyl-5-ethylpyrrolidin-2-one Chemical compound CCC1CCC(=O)N1C=C DJABNVJZYFGAJE-UHFFFAOYSA-N 0.000 claims description 2
- HQGPZXPTJWUDQR-UHFFFAOYSA-N 1-ethenyl-5-methylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1C=C HQGPZXPTJWUDQR-UHFFFAOYSA-N 0.000 claims description 2
- GIQLJJKZKUIRIU-UHFFFAOYSA-N 1-ethenyl-6-ethylpiperidin-2-one Chemical compound CCC1CCCC(=O)N1C=C GIQLJJKZKUIRIU-UHFFFAOYSA-N 0.000 claims description 2
- FFDNCQYZAAVSSF-UHFFFAOYSA-N 1-ethenyl-6-methylpiperidin-2-one Chemical compound CC1CCCC(=O)N1C=C FFDNCQYZAAVSSF-UHFFFAOYSA-N 0.000 claims description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims description 2
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical group [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 2
- 150000003335 secondary amines Chemical group 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- QNIRRHUUOQAEPB-UHFFFAOYSA-N 2-(prop-2-enoylamino)butane-2-sulfonic acid Chemical compound CCC(C)(S(O)(=O)=O)NC(=O)C=C QNIRRHUUOQAEPB-UHFFFAOYSA-N 0.000 claims 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 description 19
- 239000007788 liquid Substances 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 12
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000012991 xanthate Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 8
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 8
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 8
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 230000003993 interaction Effects 0.000 description 7
- 238000009472 formulation Methods 0.000 description 6
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- 150000008163 sugars Chemical class 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000005587 bubbling Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 238000002270 exclusion chromatography Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000002355 alkine group Chemical group 0.000 description 3
- 238000004873 anchoring Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 3
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- 229940095095 2-hydroxyethyl acrylate Drugs 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- OIETYYKGJGVJFT-UHFFFAOYSA-N 3-[dimethyl-[3-(2-methylprop-2-enoylamino)propyl]azaniumyl]propane-1-sulfonate Chemical compound CC(=C)C(=O)NCCC[N+](C)(C)CCCS([O-])(=O)=O OIETYYKGJGVJFT-UHFFFAOYSA-N 0.000 description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Chemical class [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920000359 diblock copolymer Polymers 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 159000000014 iron salts Chemical class 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000569 multi-angle light scattering Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000003129 oil well Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 150000002976 peresters Chemical class 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000003340 retarding agent Substances 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- VYGBQXDNOUHIBZ-UHFFFAOYSA-L sodium formaldehyde sulphoxylate Chemical compound [Na+].[Na+].O=C.[O-]S[O-] VYGBQXDNOUHIBZ-UHFFFAOYSA-L 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 239000004296 sodium metabisulphite Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 2
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- CAAIULQYGCAMCD-UHFFFAOYSA-L zinc;hydroxymethanesulfinate Chemical compound [Zn+2].OCS([O-])=O.OCS([O-])=O CAAIULQYGCAMCD-UHFFFAOYSA-L 0.000 description 2
- VWXLCWNPSOUPPE-UHFFFAOYSA-N (1-amino-2-methylpropylidene)azanium;chloride Chemical compound Cl.CC(C)C(N)=N VWXLCWNPSOUPPE-UHFFFAOYSA-N 0.000 description 1
- VGPBTNMZOCCNAK-UHFFFAOYSA-N (2-ethyl-3-hydroxyhexyl) prop-2-enoate Chemical compound CCCC(O)C(CC)COC(=O)C=C VGPBTNMZOCCNAK-UHFFFAOYSA-N 0.000 description 1
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical class O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 description 1
- DOGQRRGVLIGIEG-UHFFFAOYSA-N 1-(prop-2-enoylamino)butane-2-sulfonic acid Chemical group CCC(S(O)(=O)=O)CNC(=O)C=C DOGQRRGVLIGIEG-UHFFFAOYSA-N 0.000 description 1
- HUOBWFKCWUVATL-UHFFFAOYSA-N 1-butyl-2-ethenylbenzene Chemical compound CCCCC1=CC=CC=C1C=C HUOBWFKCWUVATL-UHFFFAOYSA-N 0.000 description 1
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- ADTJPOBHAXXXFS-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]prop-2-enamide Chemical compound CN(C)CCCNC(=O)C=C ADTJPOBHAXXXFS-UHFFFAOYSA-N 0.000 description 1
- QYMUDOWMRHNHHP-UHFFFAOYSA-N n-[4-(dimethylamino)butyl]prop-2-enamide Chemical compound CN(C)CCCCNC(=O)C=C QYMUDOWMRHNHHP-UHFFFAOYSA-N 0.000 description 1
- QJUUSZDOMRLEKH-UHFFFAOYSA-N n-[4-(dimethylamino)cyclohexyl]-2-methylprop-2-enamide Chemical compound CN(C)C1CCC(NC(=O)C(C)=C)CC1 QJUUSZDOMRLEKH-UHFFFAOYSA-N 0.000 description 1
- OPAXUYFLCNSBLZ-UHFFFAOYSA-N n-[4-(dimethylamino)cyclohexyl]prop-2-enamide Chemical compound CN(C)C1CCC(NC(=O)C=C)CC1 OPAXUYFLCNSBLZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001196 nonadecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001236 palmitoleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 229920000233 poly(alkylene oxides) Chemical group 0.000 description 1
- 229920000580 poly(melamine) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- RZKYDQNMAUSEDZ-UHFFFAOYSA-N prop-2-enylphosphonic acid Chemical compound OP(O)(=O)CC=C RZKYDQNMAUSEDZ-UHFFFAOYSA-N 0.000 description 1
- ATLPLEZDTSBZQG-UHFFFAOYSA-N propan-2-ylphosphonic acid Chemical compound CC(C)P(O)(O)=O ATLPLEZDTSBZQG-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 239000012989 trithiocarbonate Substances 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Classifications
-
- 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
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/24—Macromolecular compounds
- C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C04B24/2688—Copolymers containing at least three different monomers
-
- 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
- C04B20/00—Use of materials as fillers for mortars, concrete or artificial stone according to more than one of groups C04B14/00 - C04B18/00 and characterised by shape or grain distribution; Treatment of materials according to more than one of the groups C04B14/00 - C04B18/00 specially adapted to enhance their filling properties in mortars, concrete or artificial stone; Expanding or defibrillating materials
- C04B20/10—Coating or impregnating
- C04B20/1018—Coating or impregnating with organic materials
- C04B20/1029—Macromolecular compounds
- C04B20/1033—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- 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
- C09K8/42—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
- C09K8/487—Fluid loss control additives; Additives for reducing or preventing circulation loss
-
- 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
- C09K8/50—Compositions for plastering borehole walls, i.e. compositions for temporary consolidation of borehole walls
-
- 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
-
- 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
- C09K8/84—Compositions based on water or polar solvents
- C09K8/845—Compositions based on water or polar solvents containing inorganic compounds
-
- 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
- C09K8/84—Compositions based on water or polar solvents
- C09K8/86—Compositions based on water or polar solvents containing organic compounds
- C09K8/88—Compositions based on water or polar solvents containing organic compounds macromolecular compounds
- C09K8/882—Compositions based on water or polar solvents containing organic compounds macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- E—FIXED CONSTRUCTIONS
- E21—EARTH OR ROCK DRILLING; MINING
- E21B—EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- E21B33/00—Sealing or packing boreholes or wells
- E21B33/10—Sealing or packing boreholes or wells in the borehole
- E21B33/13—Methods or devices for cementing, for plugging holes, crevices or the like
- E21B33/14—Methods or devices for cementing, for plugging holes, crevices or the like for cementing casings into boreholes
-
- 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
- C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
- C04B2103/46—Water-loss or fluid-loss reducers, hygroscopic or hydrophilic agents, water retention agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2438/00—Living radical polymerisation
- C08F2438/03—Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]
Definitions
- the present invention relates to the field of petroleum extraction. More specifically, it relates to agents providing a control effect of the filtrate in fluids injected under pressure in underground formations.
- underground formation In the field of petroleum extraction, many stages are conducted by injecting fluids under pressure into underground formations.
- underground formation is understood in its broadest sense and includes both a rock containing hydrocarbons, especially oil, that the different layers of rock crossed to access this oil rock and ensure the extraction of hydrocarbons.
- rock is used to designate any type of material constituting a solid subterranean formation, whether the material constituting it is a rock or not, strictly speaking.
- oil rock is used here as a synonym for "oil reservoir” and refers to any underground formation containing hydrocarbons, especially oil, whatever the nature of the material containing these hydrocarbons (rock or sand by example).
- drilling fluids for completing and reconditioning wells, in particular drilling fluids, whether they are used to access the oil rock or to drill the reservoir itself. the same is true (“drill in”) or the fracturing fluids, or even the completion fluids, the fluids of control or reconditioning ("workover fluids”) or the ring fluids or fluids of "packer”.
- a specific case is that of petroleum cement grouts, which are used for the cementation of the annulus of the oil wells according to a method well known per se, described for example in Le Forage by JP Nguyen (Technip 1993). These oil cement grouts are injected under pressure into the interior of a metal casing (casing) introduced into the borehole of the oil wells and then rise, under the effect of pressure by the so-called “annular” space ( “Annulus”) located between the casing and the borehole then take and harden in this ring, thus ensuring the stability of the well being drilled.
- casing metal casing
- Annulus annulus
- the loss of fluid may further induce a quick setting of the cement, before the annular space is cemented, which can, among other things, weaken the structure of the well and impair its seal.
- agents for controlling the filtrate of the aforementioned type have been proposed, which notably include cellulose derivatives (for example, hydroxyethylcellulose) or else AMPS-based copolymers such as those described, for example, in US 4,632,186 or US 4,515,635.
- cellulose derivatives for example, hydroxyethylcellulose
- AMPS-based copolymers such as those described, for example, in US 4,632,186 or US 4,515,635.
- These additives are not always fully adapted to ensure, in practice, effective limitation of fluid loss.
- the presence of other additives can inhibit the effect of agents used to ensure control of the filtrate.
- the above filtrate control agents generally see their properties degrade.
- An object of the present invention is to provide novel filtrate control agents for pressurized fluids in subterranean formations, which are well suited in practice.
- the present invention proposes the use of particular copolymers, which are capable of ensuring a control effect of the filtrate when they are used with particles with which they associate, these particles possibly being particles present in the within the underground formation; and / or cement particles in the case of a fluid used in cementing; and / or particles injected into subterranean formations with the copolymers.
- the subject of the present invention is the use, as control agent, of the filtrate in a fluid (F) injected under pressure into an underground formation
- said fluid (F) comprises solid particles (p) and / or is contacted with solid particles (p) within the subterranean formation following its injection,
- a block polymer (P) comprising:
- the specific polymer used in the context of the present invention by the presence of the two specific blocks (A) and (B) is found to provide a particularly effective control effect of the fluid: the presence of the block (A) ensures anchoring of the polymer on the particles, and the presence of the long block (B), of high and soluble size, schematically ensures a local increase effect of the viscosity of the fluid (F) around the particles.
- the interaction between the short block (A) and the particles (p) is as strong as possible and, advantageously, that this interaction is irreversible.
- the short block (A) of a polymer (P) useful according to the invention comprises:
- At least one chemical group forming at least one bond of ionic, covalent or iono-covalent type between the polymer and the particle;
- a plurality of chemical groups each forming at least one hydrogen and / or Van der Waals bond between the polymer and the particle, all of these bonds together forming a global binding of force at least in the range of that of an ionic type bond; , covalent, iono-covalent.
- the strong interactions between particles and polymers also make it possible, if necessary, to use the polymer (P) in the presence of additives which usually impair the effectiveness of the filtrate control agents.
- the polymers (P) as employed according to the invention can be used in most fluid formulations intended to be injected into petroleum rocks, in particular petroleum cement slurries comprising dispersant-type additives or retardant agents as well as in drilling and fracturing fluids.
- the fluid (F) injected comprises the polymer (P) but does not comprise solid particles (p), and it encounters said particles (p) within the subterranean formation following its injection .
- the association between particles and polymers is then in situ.
- a fluid may for example be injected during a drilling operation, and rock cuttings formed during drilling then act as particles (p) in situ.
- the injected fluid (F) comprises, before the injection, at least a part, and in general all, of the particles (p) associated with the polymer (P), it being understood that it may possibly meet other particles (p) within the subterranean formation.
- the polymer (P) and the particles (p) are mixed during the formulation of the fluid (F), at the place of operation or upstream, typically by adding the particles (p), to the dry state or optionally in the dispersed state, to a composition comprising the polymer (P) in solution.
- the fluid (F) may for example be a petroleum cement slurry, which is prepared by adding cement powder as particles (p) in an aqueous composition comprising the polymer (P) in solution .
- the fluid (F) is manufactured, advantageously at the place of operation, from a composition (premix) prepared upstream (hereinafter referred to as "blend") comprising the polymer (P) and at least a portion of the particles (p), generally in a dispersing liquid.
- blend a composition (premix) prepared upstream (hereinafter referred to as "blend") comprising the polymer (P) and at least a portion of the particles (p), generally in a dispersing liquid.
- this blend is mixed with the other constituents of the fluid (F).
- the polymer (P) incidentally has the non-negligible advantage of improving the dispersibility and suspension of the particles (p).
- the polymer (P) associated with the particles (p) can be used primarily as dispersant and stabilizer of the dispersion of the particles (p), while at the same time ensuring a carrier effect. filtrate control.
- the subject of the present invention is certain particular block polymers which can be used according to the invention, which have been developed by the inventors specifically for this application.
- the invention also relates to the fluids for injection under pressure in a petroleum rock or a wellbore comprising these specific block polymers, as well as blends for the preparation of these fluids comprising these polymers in combination with particles (p).
- Fluid (F) and long block (B) are also relates to the fluids for injection under pressure in a petroleum rock or a wellbore comprising these specific block polymers, as well as blends for the preparation of these fluids comprising these polymers in combination with particles (p).
- fluid is meant, within the meaning of the description any medium, homogeneous or not, comprising a liquid or viscous carrier optionally carrying a dispersed phase, liquid or gelled, and / or solid particles, said medium being generally pumpable by means pressurized injection devices used in the application under consideration.
- liquid or viscous vector of the fluid (F) is meant the fluid itself; or the solvent in the case where the fluid comprises dissolved compounds and / or the continuous phase in the case where the fluid contains dispersed elements (droplets of liquid or gelled dispersed phase, solid particles, etc.).
- the nature of the fluid (F) and the long block (B) of the polymers (P) used according to the present invention can vary to a large extent, subject to the compatibility of the liquid or viscous fluid medium (F) and the block long (B).
- a long block (B) of hydrophilic nature is used when the liquid or viscous vector present in the fluid (F) is hydrophilic in nature; conversely, when the liquid or viscous fluid vector (F) is hydrophobic, a long block (B) of hydrophobic nature is used.
- the long block (B) of the polymers useful according to the invention is specifically soluble in the fluid (F).
- the long block (B) taken alone can be dissolved in the liquid or viscous fluid vector (F).
- the long block (B) is soluble at 25 ° C. and 1% by weight in the liquid or viscous fluid medium (F).
- the concept of "solubility at 25 ° C” implies only that a more or less viscous or gelled solution can be obtained which, at 25 ° C., does not lead to precipitation. This notion does not exclude that the dissolution of the block (B) may involve preheating above 25 ° C to obtain this solution.
- the concept of "solubility at 25 ° C” implies the possibility of forming a solution that does not precipitate at 25 ° C, and not the possibility of forming at 25 ° C a solution that does not precipitate.
- the long block (B) develops the least possible interaction, or even no interaction, with the particles (p). It is also preferable that the long block (B) of the polymers (P) useful according to the invention develops fewer interactions with the particles than the short block (A). In any case, the block (A) and the block (B) have distinct compositions. This means that:
- Blocks (A) and (B) comprise distinct monomeric units; or
- At least some of the monomers present on the block (A) are not present on the block (B); and / or at least some of the monomers present on the block (B) are not present on the block (A)
- Block (A) and block (B) comprise the same monomer units, but in different proportions.
- the fluid (F) is an aqueous fluid.
- aqueous is meant herein that the fluid comprises as a liquid or viscous carrier water, either as a sole constituent of the liquid or viscous carrier, or in combination with other water-soluble solvents.
- the water advantageously remains the majority solvent in the liquid or viscous vector, advantageously present in a proportion of at least 50% by weight. mass, or even at least 75% by weight relative to the total mass of solvents in the liquid or viscous carrier.
- the block (B) is advantageously a block of hydrophilic nature.
- block of hydrophilic nature is meant here a polymer block which, in the isolated state, is soluble in pure water at a rate of 1% by weight at 25 ° C. (the dissolution may possibly involve heating ), forming a more or less viscous solution, even gelled, but without precipitate formation at 25 ° C.
- the hydrophilic block (B) used when the fluid (F) is an aqueous fluid is constituted at least predominantly by monomer units selected from the group consisting of the monomer units U 1 to U 5 defined below, and the mixtures of these monomeric units: monomeric units U1: monomeric units comprising an acrylamide functional group, especially dimethylacrylamide (DMA) or even (meth) acrylamide, morpholine N-oxide acrylamide, diacetone acrylamide; the block (B) advantageously comprises monomer units of this type monomer units U2: monomeric units comprising a sulphonic acid or sulphonate functional group, including in particular 3-sulphopropyl (meth) acrylate units, 2-propene-1-sulphonic acid, Sodium 1-allyloxy-2-hydroxypropyl sulphonate (COPS1), especially 2-acrylamido-2-methylpropanesulphonic acid (AMPS), (meth) allyl sulphonate, sodium vinyl sulphonate, sodium
- tetrahydrofurfuryl acrylate vinyl acetamide, vinyl pyrrolidone, N-vinylpiperidone, N-vinyl caprolactam, N-vinyl-5-methyl-2-pyrrolidone, N-vinyl-5-ethyl-2-pyrrolidone, N-vinyl-6 -methyl-2-piperidone, N-vinyl-6-ethyl-2-piperidone, N-vinyl-7-methyl-2-caprolactam, N-vinyl-7-ethyl-2-caprolactam.
- monomer units U4 monomer units carrying ammonium groups, especially esters of mono- or dicarboxylic acids [alpha], [beta] -ethylenically unsaturated with amino alcohols, such as N, N-dimethylaminomethyl (meth) acrylate, N N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl acrylate, N, N-dimethylaminopropyl (meth) acrylate, N, N-diethylaminopropyl (meth) acrylate and N, N-dimethylaminocyclohexyl (meth) acrylate;
- amides of [alpha], [beta] -ethylenically unsaturated mono- or di-carboxylic acids with diamines having at least one primary or secondary amine group such as N- [2- (dimethylamino) ethyl] acrylamide, N [ 2- (dimethylamino) ethyl] methacrylamide, N- [3- (dimethylamino) propyl] acrylamide, N- [3- (dimethylamino) propyl] methacrylamide, N- [4- (dimethylamino) butyl] acrylamide, N- [4] [N- [2- (diethylamino) ethyl] acrylamide, N- [4- (dimethylamino) cyclohexyl] acrylamide, N- [4- (dimethylamino) cyclohexyl] methacrylamide
- ⁇ , ⁇ -diallylamines and N, N-diallyl-N-alkylamines including especially 3-sulfopropyldimethyl-3-methacrylamidopropylammonium, N- (2-methacryloyloxyethyl) -N, N-dimethyl-N- (3-sulfopropyl) ammoniumbetaine, N- (2-1- (3-sulfo-propyl) -2-vinylpyridinium-betaine, and N- (2-1- (3-sulfopropyl) -4-vinylpyridinium betaine monomer units U5 monomeric acrylate units, bearing COOH or COO- , including in particular acrylic acid, methacrylic acid, ethacrylic acid, [alpha] -chloroacrylic acid, crotonic acid, maleic acid, itaconic acid, citraconic acid, mesaconic acid, glutaconic acid, aconitic acid, fumaric
- the block (B) of hydrophilic nature used when the fluid (F) is an aqueous fluid consists essentially or even exc monomeric units of the above-mentioned type, in which, in the abovementioned units, the acid groups may be wholly or partly in the form of a free acid and / or in the form of a salt for example of potassium, sodium or ammonium (form neutralized).
- polymer or polymer block consisting at least predominantly of monomeric units refers to a (block) homopolymer or copolymer resulting from the polymerization of a monomer mixture including monomers x, this (block) homopolymer or copolymer comprising less than 25 mol%, preferably less than 15% and even more preferably less than 10 mol% of monomer units other than the 'x' units.
- polymer or polymer block consisting essentially of monomer units 'x' for its part means, within the meaning of the present description, a (block) homopolymer or copolymer consisting at least predominantly of monomer units 'x' of the type above, more specifically comprising less than 5 mol%, preferably less than 2% and even more preferably less than 1 mol% of monomer units other than 'x' units.
- the hydrophilic block (B) used when the fluid (F) is an aqueous fluid may comprise hydrophobic monomers in small proportions, typically at least 0, 05%, including at least 0.1%, or at least 0.5%, where applicable; this content of hydrophobic monomers preferably remains below 10%, for example less than 5%, especially less than 3%, or even 2%, these percentages being expressed by weight relative to the total mass of monomer units in the block (B).
- hydrophobic monomers of this type can typically (but not exclusively) be selected from alkyl acrylates (such as methyl acrylate); styrene; alkyl methacrylates; and / or vinyl acetate.
- the long block (B) present in the polymers employed according to the present invention also has a sufficiently high mass to ensure the control effect of the desired filtrate.
- the block (B) typically has a weight average molecular weight greater than 100,000 g / mol, preferably greater than 150,000 g / mol, for example greater than 200,000 g / mol, especially greater than 250,000 g / mol. g / mol, especially when the block (B) is of one of the aforementioned types.
- this weight average molecular weight is most often less than 3,000,000 g / mol (and typically between 150,000 and 2,000,000 g / mol), but higher masses can be envisaged in absolute terms, except in the particular case of a fluid (F) used in the context of a cementing operation, where it is preferable that the mass
- the weight average molecular weight of the long block (B) remains less than 1,000,000 g / mol, and advantageously less than 800,000 g / mol.
- the block (B) has a weight average molecular weight of between 10,000 and 100,000 g / mol, preferably at least 20,000 g / mol, for example from less than 25,000 g / mol, this weight average molecular weight typically being less than 90,000, for example less than 75,000, or even less than 50,000.
- An estimate of the weight average molecular weight of the long block (B) can be measured by steric exclusion chromatography and mass measurement using external calibration with relative ethylene oxide (CES) standards, which leads to a slightly increased value of the weight average molecular weight designated in the present description by Mw (relative CES).
- CES relative ethylene oxide
- This Mw (relative CES) is typically measured under the following conditions:
- Mobile phase Mixture of 80% by weight of deionized water supplemented with 0.1 M NaNO 3 and 20% by weight of acetonitrile.
- Sample concentration about 0.5% by mass of dry matter in the mobile phase
- the Mw (relative CES) of the long block (B) of the polymers (P) which are useful according to the invention is generally greater than or equal to 125 000 g / mol, preferably greater than or equal to 150 000 g / mol, this Mw (CES relative) being typically between 200,000 and 2,500,000 g / mol, especially between 250,000 and 2,000,000 g / mol. According to a more particular embodiment, it may be less than 125,000 g / mol, for example between 12,500 and 100,000 g / mol.
- the Mw (relative CES) of the long block (B) of the polymers (P) typically (but not exclusively) between 25,000 and 900 000 g / mol, for example between 250,000 and 900,000 g / mol.
- the Mw (relative CES) of the polymer (P) is measured, which, because of the low mass of the block (A) also represents a fairly good approximation, increased, of the mass average molecular weight of the block (B). ).
- the Mw (relative CES) of the polymer (P) is in general greater than or equal to 15,000 g / mol, and for example greater than or equal to 150,000 g / mol, preferably greater than or equal to 200,000 g / mol, example greater than or equal to 300,000 g / mol, in particular greater than or equal to 400,000 g / mol, this Mw (relative CES) of the polymer (P) being typically between 200,000 g / mol and 2,500,000 g / mol, in particular between 250,000 g / mol and 2,000,000 g / mol. It is more particularly between 25,000 and 900,000 g / mol, for example between 250,000 g / mol and 800,000 g / mol in the case of a fluid (F) used in the context of a cementing operation.
- the block (B) is advantageously a block of hydrophilic nature, preferably comprising U1 units of the aforementioned type, in particular dimethylacrylamide DMA units, possibly, but not necessarily, in combination with U2 units, in particular acrylamidomethylpropanesulphonic acid units (AMPS) ), optionally wholly or partly in sulphonate form, for example in the form of its sodium salt.
- U1 units of the aforementioned type in particular dimethylacrylamide DMA units, possibly, but not necessarily, in combination with U2 units, in particular acrylamidomethylpropanesulphonic acid units (AMPS) ), optionally wholly or partly in sulphonate form, for example in the form of its sodium salt.
- AMPS acrylamidomethylpropanesulphonic acid units
- the block (B) consists at least predominantly (for example essentially, or exclusively) of a mixture of DMA and AMPS units, with a DMA AMPS molar ratio, for example between 60/40 and 90/10, especially between 75/25 and 85/15 and typically of the order of 80/20.
- Block (B) typically has a weight average molecular weight of between 150,000 and 750,000 g / mol, preferably between 200,000 and 700,000 g / mol.
- the block (B) may have a weight average molecular weight of between 15,000 and 150,000 g / mol, preferably between 20,000 and 100,000 g / mol.
- the block (B) typically has a Mw (relative GPC) of between 200,000 and 800,000, preferably between 250,000 and 900,000 g / mol, for example 300,000 to 600,000 g / mol, the polymer (P) having in general a Mw (relative CES) included in these ranges.
- the block (B) may alternatively have a Mw (relative GPC) of between 20,000 and 200,000, preferably between 25,000 and 180,000 g / mol, for example 30,000 and 150,000 g / mol, the polymer (P) having in general a Mw (relative CES) included in these ranges.
- the long block (B) used when the fluid (F) is a petroleum cement slurry is typically a DMA / AMPS statistical block, with a DMA / AMPS molar ratio between 75/25 and 85/15 (typically of the order of 80/20), and a Mw (GPC-MALS) of between 20,000 and 7,500,000, in particular between 200,000 and 750,000, for example between 400,000 and 600,000.
- particle in the sense in which it is used in the present description is not confined to that of individualized particles. It refers more generally to solid entities dispersible within a fluid, in the form of objects (individual particles, aggregates, etc.) whose dimensions are less than 5 mm, preferably 2 mm, for example less than 1 mm.
- the nature of the particles (p) and the short block (A) of the polymers (P) used according to the present invention can vary to a large extent, provided that the block (A) interacts with the particles (p) and leads to an immobilization, preferably irreversible, of polymer (P) on the surface of the particles (p).
- the block (A) generally comprises monomer units carrying groups developing with the particles (p) stronger interactions than the long block (B).
- the particles (p) are mineral particles introduced into the fluid (F) or with which the fluid (F) comes into contact following its injection. These particles (p) are then typically particles of cement, calcium carbonate, clay, barite, silica, sand or carbon black.
- the block (A) is preferably constituted at least predominantly (and preferably essentially, if not exclusively) by monomer units chosen from the preferential groups defined below, to be adapted case by case as a function of the nature of the particles (p). :
- the block (A) may in particular consist at least in the majority (and preferably essentially or exclusively) of:
- the block (B) is then typically constituted at least predominantly (and preferably substantially, or even exclusively) by units U1 and / or U2 of the aforementioned type
- the block (A) may in particular be constituted at least predominantly (and preferably substantially, if not exclusively) by:
- the block (B) is then typically constituted at least predominantly (and preferably essentially, if not exclusively) by units U1 and / or U2 and / or U5 of the aforementioned type
- the block (A) may in particular be constituted at least predominantly (and preferably substantially or exclusively) by
- the block (B) is then typically constituted at least predominantly (and preferably essentially, if not exclusively) by units U1 and / or U2 of the aforementioned type for particles (p) of carbon black, the block (A) can in particular be constituted at least predominantly (and preferably essentially or exclusively) by hydrophobic units U8, including in particular
- the block (B) is then typically constituted at least predominantly (and preferably substantially, if not exclusively) by units of units U1 and / or U2 and / or U5 of the aforementioned type
- the short block (A) present in the polymers employed according to the present invention has, in general, a weight average molecular weight of between 500 and 30,000 g / mol, for example between 1000 and 25,000 g. / mol and especially when the block (A) is of one of the aforementioned types.
- the short block (A) is a poly (acrylic acid) homopolymer block of weight average molecular weight ranging from 1 000 to 20,000 g / mol.
- the weight-average molecular mass of the short block (A) can be measured in particular by gel permeation chromatography followed by multi-angle light scattering (GPC-MALS) analysis.
- Polymers useful according to the present invention are particular polymers, which comprise at least two blocks of very different size, including a block (B) of large size.
- the polymers (P) are preferably prepared by controlled radical polymerization, which allows to finely control the size of the two blocks.
- the controlled radical polymerization technique is a well-known technique which, using a polymerization control agent, makes it possible to obtain controlled mass polymers, in particular block polymers which can be controlled at the same time. the architecture and size of each block.
- the polymers (P) useful according to the invention may be polymers of the type prepared according to a process comprising the following steps:
- the ethylenically unsaturated monomers which are identical or different, chosen for the constitution of the block (B) or of the block (A) -;
- step (E1) a source of free radicals adapted to the polymerization of said monomers; and the polymer obtained at the end of step (E1), which acts as a control agent for the radical polymerization and on which the block (B) -respectively the block (A) is grafted.
- the size of the polymer block in formation is controlled by the monomer / control agent molar ratio corresponding to the initial quantity of monomers relative to the amount of control agent: schematically, all the chains grow from each of the present control agents and the monomers are distributed evenly over all the growing chains.
- the monomer / control agent molar ratio thus dictates the degree of polymerization of the block synthesized in each of the steps, and thus makes it possible to define the theoretical average molecular weight expected for each of the blocks.
- the molar monomer / control agent ratios in steps (E1) and (E2) are chosen so that:
- the theoretical number average molecular weight of the block (A) is between 250 and 25,000 g / mol, preferably between 500 and 15,000 g / mol, especially between 1,000 and 10,000 g / mol.
- the theoretical number average molecular weight of the block (B) is between 70,000 and 5,000,000 g / mol, preferably between 80,000 and 3,000,000 g / mol, especially between 90,000 and 2,000,000 g / mol. .
- this theoretical number average molecular weight of the block (B) is more preferably between 90,000 and 1,000,000 g / mol, advantageously between 100,000 and 500,000 g / mol.
- the block (B) can advantageously be prepared in step (E2) by bringing into contact: the ethylenically unsaturated monomers, which are identical or different, chosen for forming the block (B);
- This polymerization technique allows access to blocks (B) of large size.
- the synthesis of the block (B) can be carried out under the polymerization conditions described in the application WO 2012/042167.
- the block (B) when the block (B) is hydrophilic, the block (B) can be synthesized by contacting, within an aqueous medium (M) in which the block (B) formed is not soluble:
- the ethylenically unsaturated monomers which are identical or different, chosen for the constitution of the block (B), chosen to be soluble in the aqueous medium (M)
- a reactive stabilizer which comprises:
- a group (G) ensuring a living character and controlled to the radical polymerization of step (E), such as, for example, a group carrying a thiocarbonylthio group -S (C S) -
- the conditions to be used in the aforementioned polymerization steps can be those typically used in controlled radical polymerizations.
- step (E) of the process of the invention any source of free radicals known per se. It can be for example one of the following initiators:
- hydrogen peroxides such as tertiary butyl hydroperoxide, cumene hydroperoxide, t-butyl peroxyacetate, t-butyl peroxybenzoate, t-butylperoxyoctoate, t-butylperoxynethodecanoate and t-butylperoxyisobutarate; , lauroyl peroxide, t-amylperoxypivalte, t-butylperoxypivalate, dicumyl peroxide, benzoyl peroxide, potassium persulfate, ammonium persulfate, azo compounds such as: 2-2'-azobis (isobutyronitrile), 2,2'-azobis (2-butanenitrile), 4,4'-azobis (4-pentanoic acid), 1,1 ' azobis (cyclohexane-carbonitrile), 2- (t-butylazo) -2-cyanopropane, 2,2'-azo
- alkali metal bisulfite such as sodium metabisulphite
- alkali metal persulfates in combination with an arylphosphinic acid, such as benzene phosphonic acid and the like, and reducing sugars.
- an arylphosphinic acid such as benzene phosphonic acid and the like
- a radical initiator of the redox type which has the advantage of not requiring heating of the reaction medium (no thermal initiation), which allows better still manage the exotherm of the reaction.
- the source of free radicals employed can typically be selected from redox initiators conventionally used in radical polymerization, typically not requiring heating for their thermal initiation. It is typically a mixture of at least one oxidizing agent with at least one reducing agent.
- the oxidizing agent present in the redox system is preferably a water-soluble agent.
- This oxidizing agent may for example be chosen from peroxides, such as: hydrogen peroxide, tertiary butyl hydroperoxide, cumene hydroperoxide, t-butyl peroxyacetate, t-butylperoxybenzoate, t -butylperoxyoctoate, the butylperoxynéodécanoate, t-butylperoxyisobutarate, lauroyl peroxide, t-amylperoxypivalte, t-butylperoxypivalate, dicumyl peroxide, benzoyl peroxide; sodium persulfate, potassium persulfate, ammonium persulfate, or even potassium bromate.
- peroxides such as: hydrogen peroxide, tertiary butyl hydroperoxide, cumene hydroperoxide, t-butyl
- the reducing agent present in the redox system is also preferably a water-soluble agent.
- This reducing agent can typically be selected from sodium formaldehyde sulfoxylate (especially in its dihydrate form, known as Rongalit or in the form of an anhydride), ascorbic acid, erythorbic acid, sulphites, bisulphites or metasulfites (in particular sulphites, bisulphites or metasulfites of alkali metals), nitrilotrispropionamides, and tertiary amines and ethanolamines (preferably water-soluble).
- Possible redox systems include combinations such as:
- alkali metal bisulfite such as sodium metabisulphite
- arylphosphinic acid such as benzene phosphonic acid and the like, and reducing sugars.
- An interesting redox system includes (and preferably consists of), for example, the combination of ammonium persulfate and sodium formaldehyde sulfoxylate.
- reaction medium of step (E) is free of copper.
- a copper complexing agent such as EDTA.
- control agent used in the synthesis steps of the blocks (A) and (B) can vary to a large extent.
- control agent may carry several thiocarbonylthio groups.
- control agent used in step (E2) is a living polymer resulting from step (E1). It can also be envisaged that the control agent of step (E1) is derived from a previous step (E0) in which the radical polymerization of a composition comprising:
- an initiator of radical polymerization source of free radicals.
- control agent adapted to the synthesis of the polymer (P) useful according to the invention advantageously corresponds to the formula (A) below:
- the groups R 1 or Z when substituted, may be substituted with optionally substituted phenyl groups, optionally substituted aromatic groups, saturated or unsaturated carbon rings, saturated or unsaturated heterocycles, or alkyloxycarbonyl or aryloxycarbonyl groups ( -COOR), carboxy (-COOH), acyloxy (-O2CR), carbamoyl (-CONR2), cyano (-CN), alkylcarbonyl, alkylarylcarbonyl, arylcarbonyl, arylalkylcarbonyl, phthalimido, maleimido, succinimido, amidino, guanidimo, hydroxy (-OH ), amino (-NR2), halogen, perfluoroalkyl C n F 2n + 1, allyl, epoxy, alkoxy (-OR), S-alkyl, S-aryl, groups having a hydrophilic or ionic character such as alkali metal salts of carboxylic acids, alkali metal salts
- R 1 is a substituted or unsubstituted alkyl group, preferably substituted.
- the optionally substituted alkyl, acyl, aryl, aralkyl or alkyne groups generally have 1 to 20 carbon atoms, preferably 1 to 12, and more preferably 1 to 9 carbon atoms. They can be linear or branched. They may also be substituted by oxygen atoms, in particular esters, sulfur or nitrogen atoms.
- alkyl radicals mention may especially be made of the methyl, ethyl, propyl, butyl, pentyl, isopropyl, tert-butyl, pentyl, hexyl, octyl, decyl or dodecyl radical.
- the alkyne groups are radicals generally of 2 to 10 carbon atoms, they have at least one acetylenic unsaturation, such as the acetylenyl radical.
- the acyl group is a radical generally having from 1 to 20 carbon atoms with a carbonyl group.
- aryl radicals there may be mentioned the phenyl radical, optionally substituted in particular by a nitro or hydroxyl function.
- aralkyl radicals mention may especially be made of the benzyl or phenethyl radical, optionally substituted in particular by a nitro or hydroxyl function.
- R 1 or Z is a polymer chain
- this polymer chain may be derived from a radical or ionic polymerization or from a polycondensation.
- control agents xanthates, trithiocarbonates, dithiocarbamates, or dithiocarbazates.
- 0ethyl-S- (1-methoxycarbonylethyl) xanthate of formula (CH 3 CH (CO 2 CH 3 )) S (C S) OEt.
- Polymers (P) useful according to the invention generally comprise only blocks (B) and (A). These are typically diblock polymers (A) - (B), but polymers comprising more blocks are possible, in particular copolymers comprising a long block (B) on which are grafted two or more short blocks (triblock polymers of type (A) - (B) - (A) in particular), or else copolymers comprising a block spacer between the block (B) and the block (A) variants that you think are reasonable?
- Some of the useful polymers according to the present invention are polymers which, to the knowledge of the inventors, have never been described in the past.
- These polymers include in particular block polymers containing, preferably as single blocks:
- At least a first block at least predominantly (and preferably substantially, or exclusively) constituted by acrylic acid units, of weight average molecular weight between 500 and 30,000 g / mol, in particular between 1,000 and 20,000; and
- a second p block (DMA / AMPS) at least predominantly (and preferably essentially, if not exclusively) constituted by a statistical mixture of DMA and AMPS units, with a DMA / AMPS molar ratio of between 60/40 and 90/10; having a molecular weight greater than 150 000 g / mol, typically between 200 000 and 2 000 000 g / mol and especially between 250 000 and 750 000 g / mol.
- aqueous fluids for injection under pressure in a petroleum rock in particular drilling fluids and fracturing fluids, comprising them in association with mineral particles, as well as blends for the preparation of these fluids.
- the polymers useful according to the invention can be used in almost all fluids used in petroleum extraction and potentially subject to fluid loss.
- the fluid (F) is a petroleum cement slurry, which comprises the polymer (P) as an additive.
- the polymer (P) associated with the particles present in cement, provides the control effect of the filtrate during cementation.
- the fluid (F) is a drilling fluid or a fracturing fluid, which comprises the polymer (P) associated with particles (p).
- the particles (p) are then most often introduced together with the polymer in the fluid (F) before the injection of the fluid.
- the polymer then generally ensures a stabilization of the dispersion of the particles in the fluid (F), while maintaining in suspension in the fluid at least a portion of the particles (p).
- concentrations of polymer and particles to be employed in these different fluids are to be adapted case by case according to the intended application and the desired rheology.
- the flask was then placed in an oil bath thermostated at 60 ° C, and the reaction medium was stirred for 4 hours at 60 ° C.
- Blocks A1 to A4 prepared as indicated in paragraph 1 .1 were used in their reaction medium obtained, without purification, with a mass of polymer m A reported in Table 2 below.
- the chosen block, in its reaction mixture without purification, was introduced into a 250 ml flask at room temperature, and then NMA (N, N-dimethylacrylamide) was added (in the amounts shown in Table 2 below).
- NMA N, N-dimethylacrylamide
- the mixture was degassed by bubbling nitrogen for 20 minutes.
- To the medium of sodium formaldehyde sulfoxylate was added in the form of a 1.0% by weight aqueous solution, the same mass of this solution being introduced as that of the ammonium persulfate solution (see Table 2).
- the polymerization reaction was allowed to proceed without stirring for 24 hours at room temperature (20 ° C).
- the polymerization reaction was then allowed to proceed without stirring for 24 hours at room temperature (20 ° C).
- diblock polymers P1 to P17 prepared in Examples 1 and the control prepared in Example 2 were used to make petroleum cement slurries having the following formulation:
- Diblock polymer (20% in aqueous solution):
- Dispersing agent polymelamine sulfonate (50% aqueous solution)
- Retarding agent calcium lignosulfonate (48% in aqueous solution)
- the filtrate control agent is mixed with liquid additives and tap water before incorporation of the cement.
- the formulation and the filtration test were carried out according to the American Petroleum Institute standard (API recommended for testing items 10B, 2nd edition April 2013).
- the slurry obtained was conditioned at 88 ° C. for 20 minutes in an atmospheric consistometer (model 1250 supplied by Chandier Engineering Inc.) previously stabilized at this temperature, which allows to simulate the conditions experienced by the cement grout when descending into a well.
- the filtrate control performance was determined by static filtration at 88 ° C in a 175mL double-opening cell equipped with 325meshx60mesh metal grid (supplied by OFITE Inc., reference 170-45).
- the performances of the polymers in the cement formulations are reported in Table 4 below:
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EP20183217.7A Pending EP3770231A1 (fr) | 2013-10-04 | 2014-10-03 | Polymeres sequences pour le controle du filtrat |
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AU (1) | AU2014331058B2 (zh) |
CA (1) | CA2924260C (zh) |
FR (1) | FR3011555A1 (zh) |
WO (1) | WO2015049378A1 (zh) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3025204B1 (fr) * | 2014-08-28 | 2018-08-10 | Chryso | Copolymeres a blocs utilisables comme fluidifiants |
FR3034777A1 (fr) * | 2015-04-07 | 2016-10-14 | Rhodia Operations | Polymeres sequences pour le controle du filtrat et de la rheologie |
FR3037073B1 (fr) * | 2015-06-03 | 2017-07-14 | Rhodia Operations | Polymeres amphiphiles pour le controle du filtrat |
FR3037074B1 (fr) | 2015-06-03 | 2017-07-14 | Rhodia Operations | Agents de suspension obtenus par polymerisation micellaire |
US20180171207A1 (en) | 2015-06-17 | 2018-06-21 | Clariant International Ltd. | Water-Soluble Or Water-Swellable Polymers As Water Loss Reducers In Cement Slurries |
EP3386299B1 (en) * | 2015-12-10 | 2024-04-24 | Adama Makhteshim Ltd. | Polyelectrolyte-layer forming block copolymers and compositions and uses thereof |
CN105694831A (zh) * | 2016-03-17 | 2016-06-22 | 中国石油集团渤海钻探工程有限公司 | 一种抗高温抗盐降粘剂及其制备方法和应用 |
US10331592B2 (en) * | 2016-05-28 | 2019-06-25 | Silicon Laboratories Inc. | Communication apparatus with direct control and associated methods |
JP7050784B2 (ja) | 2016-12-12 | 2022-04-08 | クラリアント・インターナシヨナル・リミテツド | 化粧料組成物、皮膚科学的組成物または医薬組成物におけるバイオベースのポリマーの使用 |
JP7032402B2 (ja) | 2016-12-12 | 2022-03-08 | クラリアント・インターナシヨナル・リミテツド | ある特定のレベルのバイオベース炭素を含むポリマー |
US11401362B2 (en) | 2016-12-15 | 2022-08-02 | Clariant International Ltd | Water-soluble and/or water-swellable hybrid polymer |
WO2018108665A1 (en) | 2016-12-15 | 2018-06-21 | Clariant International Ltd | Water-soluble and/or water-swellable hybrid polymer |
US11339241B2 (en) | 2016-12-15 | 2022-05-24 | Clariant International Ltd. | Water-soluble and/or water-swellable hybrid polymer |
US11306170B2 (en) | 2016-12-15 | 2022-04-19 | Clariant International Ltd. | Water-soluble and/or water-swellable hybrid polymer |
FR3064641A1 (fr) * | 2017-04-03 | 2018-10-05 | Rhodia Operations | Association pour le controle du filtrat et la migration de gaz |
AR114185A1 (es) | 2018-01-23 | 2020-07-29 | Adama Makhteshim Ltd | Síntesis de 5-cloro-2-[(3,4,4-trifluoro-3-buten-1-il)tio]-tiazol |
CN109135700B (zh) * | 2018-10-23 | 2021-05-14 | 中国石油化工股份有限公司 | 乳液悬浮聚合物选择性堵水剂及其制备方法 |
FR3088071B1 (fr) * | 2018-11-06 | 2020-11-13 | S N F Sa | Procede de recuperation assistee de petrole par injection d'une composition aqueuse polymerique |
US11603487B2 (en) * | 2020-05-29 | 2023-03-14 | Halliburton Energy Services, Inc. | Low molecular mass organic gelator wellbore stabilizers |
CN112226216B (zh) * | 2020-11-23 | 2022-09-27 | 扬州工业职业技术学院 | 一种高效石油钻井液及其制备方法 |
US11827732B2 (en) | 2021-02-04 | 2023-11-28 | Saudi Arabian Oil Company | Amphiphilic branched copolymer drilling additive |
US11851615B2 (en) | 2021-02-04 | 2023-12-26 | Saudi Arabian Oil Company | Branched block copolymer for enhanced oil recovery in sandstone formations |
CN115404061A (zh) * | 2021-12-31 | 2022-11-29 | 南京绿界新材料研究院有限公司 | 一种耐高温耐盐降失水剂组合物的制备方法 |
CN114989374B (zh) * | 2022-05-12 | 2023-05-05 | 滨州学院 | 一种交联嵌段共聚物井壁稳定剂、制备方法及应用 |
CN116622353B (zh) * | 2023-07-24 | 2023-09-22 | 大庆永铸石油技术开发有限公司 | 一种包含多糖和复合盐的无固相压井液及其制备方法 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4540498A (en) * | 1983-05-31 | 1985-09-10 | The Standard Oil Company | Block copolymers for enhanced oil recovery |
US4515635A (en) * | 1984-03-23 | 1985-05-07 | Halliburton Company | Hydrolytically stable polymers for use in oil field cementing methods and compositions |
US4632186A (en) | 1985-12-27 | 1986-12-30 | Hughes Tool Company | Well cementing method using an AM/AMPS fluid loss additive blend |
US5763548A (en) | 1995-03-31 | 1998-06-09 | Carnegie-Mellon University | (Co)polymers and a novel polymerization process based on atom (or group) transfer radical polymerization |
US7714075B1 (en) | 1996-07-10 | 2010-05-11 | Commonwealth Scientific And Industrial Research Organisation | Polymerization with living characteristics |
FR2764892B1 (fr) | 1997-06-23 | 2000-03-03 | Rhodia Chimie Sa | Procede de synthese de polymeres a blocs |
KR100589073B1 (ko) | 1997-12-18 | 2006-06-13 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 리빙 특성의 중합 방법 및 이 방법으로 제조된 중합체 |
JP2002500251A (ja) | 1997-12-31 | 2002-01-08 | ロディア・シミ | 制御されたラジカル重合によるジチオカーバメートからのブロックポリマーの合成方法 |
FR2773161B1 (fr) | 1997-12-31 | 2000-01-21 | Rhodia Chimie Sa | Procede de synthese de polymeres a blocs |
FR2794463B1 (fr) | 1999-06-04 | 2005-02-25 | Rhodia Chimie Sa | Procede de synthese de polymeres par polymerisation radicalaire controlee a l'aide de xanthates halogenes |
FR2794464B1 (fr) | 1999-06-04 | 2005-03-04 | Rhodia Chimie Sa | Procede de synthese de polymeres a blocs par polymerisation radicalaire controlee a l'aide de thioether-thiones |
FR2802208B1 (fr) | 1999-12-09 | 2003-02-14 | Rhodia Chimie Sa | Procede de synthese de polymeres par polymerisation radicalaire controlee a l'aide de xanthates |
US6569969B2 (en) | 2000-09-28 | 2003-05-27 | Symyx Technologies, Inc. | Control agents for living-type free radical polymerization, methods of polymerizing and polymers with same |
DE102005051906A1 (de) * | 2005-10-29 | 2007-05-03 | Basf Construction Polymers Gmbh | Mischpolymer auf Basis olefinischer Sulfonsäuren |
MX2010012630A (es) * | 2008-05-21 | 2010-12-14 | Basf Se | Copolimero de injerto, metodo para su produccion y su uso. |
FR2965564B1 (fr) * | 2010-09-30 | 2012-10-26 | Rhodia Operations | Preparation de polymeres hydrophiles de haute masse par polymerisation radicalaire controlee |
-
2013
- 2013-10-04 FR FR1302315A patent/FR3011555A1/fr active Pending
-
2014
- 2014-10-03 CN CN201480054646.6A patent/CN106414657A/zh active Pending
- 2014-10-03 CA CA2924260A patent/CA2924260C/fr active Active
- 2014-10-03 AU AU2014331058A patent/AU2014331058B2/en active Active
- 2014-10-03 EP EP14780519.6A patent/EP3052579A1/fr not_active Ceased
- 2014-10-03 US US15/026,780 patent/US11168026B2/en active Active
- 2014-10-03 WO PCT/EP2014/071253 patent/WO2015049378A1/fr active Application Filing
- 2014-10-03 CN CN202310744364.XA patent/CN116789917A/zh active Pending
- 2014-10-03 EP EP20183217.7A patent/EP3770231A1/fr active Pending
Non-Patent Citations (2)
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---|
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See also references of WO2015049378A1 * |
Also Published As
Publication number | Publication date |
---|---|
US20160214896A1 (en) | 2016-07-28 |
EP3770231A1 (fr) | 2021-01-27 |
FR3011555A1 (fr) | 2015-04-10 |
CN106414657A (zh) | 2017-02-15 |
AU2014331058A1 (en) | 2016-04-07 |
CA2924260C (fr) | 2023-03-21 |
CA2924260A1 (fr) | 2015-04-09 |
WO2015049378A1 (fr) | 2015-04-09 |
US11168026B2 (en) | 2021-11-09 |
CN116789917A (zh) | 2023-09-22 |
AU2014331058B2 (en) | 2018-07-05 |
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