CA1286447C - Synthese de polyacrylamide a forte masse moleculaire - Google Patents

Synthese de polyacrylamide a forte masse moleculaire

Info

Publication number: CA1286447C
Authority: CA; Canada
Prior art keywords: hydroperoxide; ferrous; reaction medium; aqueous reaction; weight percent
Prior art date: 1984-09-12
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.): Expired - Fee Related

Application number

CA000484133A

Other languages

English (en)

Inventor

Robert Allan Smith

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Goodyear Tire and Rubber Co

Original Assignee

Goodyear Tire and Rubber Co

Priority date (The priority date 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 date listed.)

1984-09-12

Filing date

1985-06-17

Publication date

1991-07-16

1985-06-17 Application filed by Goodyear Tire and Rubber Co filed Critical Goodyear Tire and Rubber Co

1991-07-16 Application granted granted Critical

1991-07-16 Publication of CA1286447C publication Critical patent/CA1286447C/fr

2008-07-16 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920002401 polyacrylamide Polymers 0.000 title abstract description 27
230000015572 biosynthetic process Effects 0.000 title abstract description 13
238000003786 synthesis reaction Methods 0.000 title abstract description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 55
239000000178 monomer Substances 0.000 claims abstract description 46
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 39
238000006116 polymerization reaction Methods 0.000 claims abstract description 37
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims abstract description 33
238000000034 method Methods 0.000 claims abstract description 29
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 20
239000012966 redox initiator Substances 0.000 claims abstract description 18
230000008569 process Effects 0.000 claims abstract description 13
238000007334 copolymerization reaction Methods 0.000 claims abstract description 11
239000012431 aqueous reaction media Substances 0.000 claims description 38
229920002554 vinyl polymer Polymers 0.000 claims description 20
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 18
-1 ferrous compound Chemical class 0.000 claims description 16
229920001577 copolymer Polymers 0.000 claims description 9
229910002651 NO3 Inorganic materials 0.000 claims description 5
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 4
QGWKRYREOQNOCC-UHFFFAOYSA-N hydrogen peroxide;1-methyl-4-propan-2-ylbenzene Chemical compound OO.CC(C)C1=CC=C(C)C=C1 QGWKRYREOQNOCC-UHFFFAOYSA-N 0.000 claims description 4
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 4
229910000359 iron(II) sulfate Inorganic materials 0.000 claims description 4
OHZCFWMJMWFNFP-ZVGUSBNCSA-L (2r,3r)-2,3-dihydroxybutanedioate;iron(2+) Chemical compound [Fe+2].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O OHZCFWMJMWFNFP-ZVGUSBNCSA-L 0.000 claims description 3
IQDYJTRQXOFUGA-UHFFFAOYSA-N 1,2-ditert-butyl-3-propan-2-ylbenzene hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC(C(C)(C)C)=C1C(C)(C)C IQDYJTRQXOFUGA-UHFFFAOYSA-N 0.000 claims description 3
BQZWVZYVMFUEOC-UHFFFAOYSA-N 1-chloro-2,3-di(propan-2-yl)benzene hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC(Cl)=C1C(C)C BQZWVZYVMFUEOC-UHFFFAOYSA-N 0.000 claims description 3
UXKSAKWJCASQBU-UHFFFAOYSA-N 1-chloro-2-propan-2-ylbenzene hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC=C1Cl UXKSAKWJCASQBU-UHFFFAOYSA-N 0.000 claims description 3
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 3
239000004277 Ferrous carbonate Substances 0.000 claims description 3
JXXRCDTYFYLOQH-UHFFFAOYSA-N OO.C(C)(C)C(C1=CC=CC=C1)C(C)C Chemical compound OO.C(C)(C)C(C1=CC=CC=C1)C(C)C JXXRCDTYFYLOQH-UHFFFAOYSA-N 0.000 claims description 3
KHADDDTZDWSVIZ-UHFFFAOYSA-N butan-2-ylbenzene;hydrogen peroxide Chemical compound OO.CCC(C)C1=CC=CC=C1 KHADDDTZDWSVIZ-UHFFFAOYSA-N 0.000 claims description 3
SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 claims description 3
RAQDACVRFCEPDA-UHFFFAOYSA-L ferrous carbonate Chemical compound [Fe+2].[O-]C([O-])=O RAQDACVRFCEPDA-UHFFFAOYSA-L 0.000 claims description 3
229960004652 ferrous carbonate Drugs 0.000 claims description 3
235000019268 ferrous carbonate Nutrition 0.000 claims description 3
229940062993 ferrous oxalate Drugs 0.000 claims description 3
229940057006 ferrous tartrate Drugs 0.000 claims description 3
KINLCXPYQDYVNG-UHFFFAOYSA-N hydrogen peroxide 1-phenylbutan-2-ylbenzene Chemical compound OO.C=1C=CC=CC=1C(CC)CC1=CC=CC=C1 KINLCXPYQDYVNG-UHFFFAOYSA-N 0.000 claims description 3
PERHPCPROKAJEC-UHFFFAOYSA-N hydrogen peroxide;methylcyclohexane Chemical compound OO.CC1CCCCC1 PERHPCPROKAJEC-UHFFFAOYSA-N 0.000 claims description 3
230000000977 initiatory effect Effects 0.000 claims description 3
OWZIYWAUNZMLRT-UHFFFAOYSA-L iron(2+);oxalate Chemical compound [Fe+2].[O-]C(=O)C([O-])=O OWZIYWAUNZMLRT-UHFFFAOYSA-L 0.000 claims description 3
229910000015 iron(II) carbonate Inorganic materials 0.000 claims description 3
LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 claims description 2
HIRMTFZGECHTFD-UHFFFAOYSA-N 1-[1-(2,3-dimethylphenyl)butan-2-yl]-2,3-dimethylbenzene;hydrogen peroxide Chemical compound OO.C=1C=CC(C)=C(C)C=1C(CC)CC1=CC=CC(C)=C1C HIRMTFZGECHTFD-UHFFFAOYSA-N 0.000 claims description 2
QABUFWQCKDRYGJ-UHFFFAOYSA-N 1-tert-butyl-2-propan-2-ylbenzene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC=C1C(C)(C)C QABUFWQCKDRYGJ-UHFFFAOYSA-N 0.000 claims description 2
UQLNYIHBLIXCHB-UHFFFAOYSA-N 2,3-dimethylbutane;hydrogen peroxide Chemical compound OO.CC(C)C(C)C UQLNYIHBLIXCHB-UHFFFAOYSA-N 0.000 claims description 2
XKGUZGHMWUIYDR-UHFFFAOYSA-N benzyl n-(3-fluoro-4-morpholin-4-ylphenyl)carbamate Chemical compound C=1C=C(N2CCOCC2)C(F)=CC=1NC(=O)OCC1=CC=CC=C1 XKGUZGHMWUIYDR-UHFFFAOYSA-N 0.000 claims description 2
OECMNLAWCROQEE-UHFFFAOYSA-N cyclohexylbenzene;hydrogen peroxide Chemical compound OO.C1CCCCC1C1=CC=CC=C1 OECMNLAWCROQEE-UHFFFAOYSA-N 0.000 claims description 2
229940076136 ferrous iodide Drugs 0.000 claims description 2
239000011790 ferrous sulphate Substances 0.000 claims description 2
235000003891 ferrous sulphate Nutrition 0.000 claims description 2
WJSJYDADTYOYSV-UHFFFAOYSA-N hydrogen peroxide 1-pentan-2-yl-2-propan-2-ylbenzene Chemical compound OO.CCCC(C)C1=CC=CC=C1C(C)C WJSJYDADTYOYSV-UHFFFAOYSA-N 0.000 claims description 2
ZMVKPQNVENMZPP-UHFFFAOYSA-N hydrogen peroxide 2,2,5-trimethylhexane Chemical compound OO.CC(C)CCC(C)(C)C ZMVKPQNVENMZPP-UHFFFAOYSA-N 0.000 claims description 2
TWNQSCQMNSSPFZ-UHFFFAOYSA-N hydrogen peroxide;1,2,3,4-tetrahydronaphthalene Chemical compound OO.C1=CC=C2CCCCC2=C1 TWNQSCQMNSSPFZ-UHFFFAOYSA-N 0.000 claims description 2
DXTCFKRAUYBHRC-UHFFFAOYSA-L iron(2+);dithiocyanate Chemical compound [Fe+2].[S-]C#N.[S-]C#N DXTCFKRAUYBHRC-UHFFFAOYSA-L 0.000 claims description 2
BQZGVMWPHXIKEQ-UHFFFAOYSA-L iron(ii) iodide Chemical compound [Fe+2].[I-].[I-] BQZGVMWPHXIKEQ-UHFFFAOYSA-L 0.000 claims description 2
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 claims description 2
PXOLVKVBWZSKDB-UHFFFAOYSA-N 1-dodecan-2-yl-2-propan-2-ylbenzene hydrogen peroxide Chemical compound OO.CCCCCCCCCCC(C)C1=CC=CC=C1C(C)C PXOLVKVBWZSKDB-UHFFFAOYSA-N 0.000 claims 1
229910021575 Iron(II) bromide Inorganic materials 0.000 claims 1
PQELHMOATLVQJL-UHFFFAOYSA-N OO.CC=CCCC1=CC=C(C(C)C)C=C1 Chemical compound OO.CC=CCCC1=CC=C(C(C)C)C=C1 PQELHMOATLVQJL-UHFFFAOYSA-N 0.000 claims 1
229940046149 ferrous bromide Drugs 0.000 claims 1
GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 claims 1
FZGIHSNZYGFUGM-UHFFFAOYSA-L iron(ii) fluoride Chemical compound [F-].[F-].[Fe+2] FZGIHSNZYGFUGM-UHFFFAOYSA-L 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 29
238000002347 injection Methods 0.000 abstract description 13
239000007924 injection Substances 0.000 abstract description 13
238000011084 recovery Methods 0.000 abstract description 12
230000008901 benefit Effects 0.000 abstract description 2
239000003921 oil Substances 0.000 description 29
229920006322 acrylamide copolymer Polymers 0.000 description 16
239000011734 sodium Substances 0.000 description 16
229910052708 sodium Inorganic materials 0.000 description 14
125000004432 carbon atom Chemical group C* 0.000 description 13
239000003208 petroleum Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000004533 oil dispersion Substances 0.000 description 11
238000012674 dispersion polymerization Methods 0.000 description 9
229910052700 potassium Inorganic materials 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000012530 fluid Substances 0.000 description 8
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 7
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 7
125000005011 alkyl ether group Chemical group 0.000 description 7
125000000217 alkyl group Chemical group 0.000 description 7
125000005013 aryl ether group Chemical group 0.000 description 7
239000012429 reaction media Substances 0.000 description 7
239000002270 dispersing agent Substances 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
230000035484 reaction time Effects 0.000 description 6
229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000003999 initiator Substances 0.000 description 5
229910003202 NH4 Inorganic materials 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
BQMNFPBUAQPINY-UHFFFAOYSA-N azane;2-methyl-2-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound [NH4+].[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C BQMNFPBUAQPINY-UHFFFAOYSA-N 0.000 description 4
239000011575 calcium Substances 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000012736 aqueous medium Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
239000012267 brine Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
238000009826 distribution Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 3
239000007788 liquid 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
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
QUPCNWFFTANZPX-UHFFFAOYSA-M paramenthane hydroperoxide Chemical compound [O-]O.CC(C)C1CCC(C)CC1 QUPCNWFFTANZPX-UHFFFAOYSA-M 0.000 description 3
238000005086 pumping Methods 0.000 description 3
239000011435 rock Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
HDGQICNBXPAKLR-UHFFFAOYSA-N 2,4-dimethylhexane Chemical compound CCC(C)CC(C)C HDGQICNBXPAKLR-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
BEBLEPZOMMWNIF-UHFFFAOYSA-L calcium;2-methyl-2-(prop-2-enoylamino)propane-1-sulfonate Chemical compound [Ca+2].[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C.[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C BEBLEPZOMMWNIF-UHFFFAOYSA-L 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
150000002432 hydroperoxides Chemical class 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000002736 nonionic surfactant Substances 0.000 description 2
YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 2
229920000223 polyglycerol Polymers 0.000 description 2
239000011414 polymer cement Substances 0.000 description 2
239000011591 potassium Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
XZPVPNZTYPUODG-UHFFFAOYSA-M sodium;chloride;dihydrate Chemical compound O.O.[Na+].[Cl-] XZPVPNZTYPUODG-UHFFFAOYSA-M 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 2
229920003169 water-soluble polymer Polymers 0.000 description 2
OEFMIXKESOQKBU-UHFFFAOYSA-N 1-dodecan-2-yl-2-propan-2-ylbenzene Chemical compound CCCCCCCCCCC(C)C1=CC=CC=C1C(C)C OEFMIXKESOQKBU-UHFFFAOYSA-N 0.000 description 1
OEYGTUAKNZFCDJ-UHFFFAOYSA-N 3-ethyloctane Chemical compound CCCCCC(CC)CC OEYGTUAKNZFCDJ-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
KNJRVOWGRUCFAD-UHFFFAOYSA-N OO.CC(CCCCCCCCCC)CC1=CC=CC=C1 Chemical compound OO.CC(CCCCCCCCCC)CC1=CC=CC=C1 KNJRVOWGRUCFAD-UHFFFAOYSA-N 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
229910001870 ammonium persulfate Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
KGQLBLGDIQNGSB-UHFFFAOYSA-N benzene-1,4-diol;methoxymethane Chemical compound COC.OC1=CC=C(O)C=C1 KGQLBLGDIQNGSB-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000013043 chemical agent Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000002283 diesel fuel Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229960002089 ferrous chloride Drugs 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000006872 improvement Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
230000035699 permeability Effects 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
238000004391 petroleum recovery Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
238000010008 shearing Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000012749 thinning agent Substances 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

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Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000484133A 1984-09-12 1985-06-17 Synthese de polyacrylamide a forte masse moleculaire Expired - Fee Related CA1286447C (fr)

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US64962284A	1984-09-12	1984-09-12
US649,622		1991-01-31

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CA000484133A Expired - Fee Related CA1286447C (fr)	1984-09-12	1985-06-17	Synthese de polyacrylamide a forte masse moleculaire

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
LT6239B (lt)	2015-04-17	2016-01-11	Valstybinis moksliniÅ³ tyrimÅ³ institutas FiziniÅ³ ir technologijos mokslÅ³ centras	Pirolo bio-polimerizacija naudojant redokso tarpininką

1985
- 1985-06-17 CA CA000484133A patent/CA1286447C/fr not_active Expired - Fee Related

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
LT6239B (lt)	2015-04-17	2016-01-11	Valstybinis moksliniÅ³ tyrimÅ³ institutas FiziniÅ³ ir technologijos mokslÅ³ centras	Pirolo bio-polimerizacija naudojant redokso tarpininką

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Date	Code	Title	Description
1997-07-16	MKLA	Lapsed

Publication	Publication Date	Title
US4592850A (en)	1986-06-03	Injection water viscosifier for enhanced oil recovery
US4736005A (en)	1988-04-05	Injection water viscosifier for enhanced oil recovery
US3002960A (en)	1961-10-03	Polyacrylamide preparation
US5883210A (en)	1999-03-16	Compositions and processes for treating subterranean formations
EP0206489B1 (fr)	1991-03-13	Acrylamides N-substitués tolérants au calcium comme agents épaississants pour systèmes aqueux
US4563290A (en)	1986-01-07	Water-soluble copolymers useful for enhanced oil recovery
US5708107A (en)	1998-01-13	Compositions and processes for treating subterranean formations
US4526947A (en)	1985-07-02	N,N-Dimethylacrylamide copolymer injection water viscosifier for enhanced oil recovery
US5922653A (en)	1999-07-13	Compositions and processes for treating subterranean formations
CN102702424A (zh)	2012-10-03	两性离子聚合物、其制备方法及在盐酸基压裂液中的应用
EP0106529A1 (fr)	1984-04-25	Fluides de forage à base de polymères élastomériques sulfonates
US4690219A (en)	1987-09-01	Acidizing using n-vinyl lactum/unsaturated amide copolymers
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US5650633A (en)	1997-07-22	Compositions and processes for treating subterranean formations
US4163476A (en)	1979-08-07	Secondary recovery process utilizing an acrylamido alkanesulfonic acid polymer
US4617359A (en)	1986-10-14	High molecular weight polyacrylamide synthesis
US4485224A (en)	1984-11-27	Acrylamide polymerization
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US4016086A (en)	1977-04-05	Polyacrylamide polymers derived from acrylonitrile without intermediate isolation
US4200151A (en)	1980-04-29	Secondary recovery process
CA1286447C (fr)	1991-07-16	Synthese de polyacrylamide a forte masse moleculaire
CN111925477A (zh)	2020-11-13	一种可增稠盐酸溶液的含氟稠化剂的制备方法
US4206058A (en)	1980-06-03	Method for stimulating well production
US4610305A (en)	1986-09-09	Oilfield flooding polymer
GB2340832A (en)	2000-03-01	Compositions and processes for treating subterranean formations

CA1286447C - Synthese de polyacrylamide a forte masse moleculaire - Google Patents

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ID=24605578

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