CA1302003C - Compositions pour epaissir une solution acide - Google Patents

Compositions pour epaissir une solution acide

Info

Publication number: CA1302003C
Authority: CA; Canada
Prior art keywords: mole percent; acrylamide; iii; carbon atoms; viscosified
Prior art date: 1986-05-19
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 - Lifetime

Application number

CA000536061A

Other languages

English (en)

Inventor

George Lewis Brode

You-Ling Fan

James Preston Stanley

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.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

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.)

1986-05-19

Filing date

1987-04-30

Publication date

1992-05-26

1987-04-30 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1992-05-26 Application granted granted Critical

1992-05-26 Publication of CA1302003C publication Critical patent/CA1302003C/fr

2009-05-26 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 55
239000002253 acid Substances 0.000 title claims abstract description 51
229920000642 polymer Polymers 0.000 claims abstract description 89
239000000178 monomer Substances 0.000 claims abstract description 82
-1 acrylyl Chemical group 0.000 claims abstract description 26
230000015572 biosynthetic process Effects 0.000 claims abstract description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
125000002091 cationic group Chemical group 0.000 claims abstract description 17
125000000129 anionic group Chemical group 0.000 claims abstract description 15
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 39
125000004432 carbon atom Chemical group C* 0.000 claims description 30
UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 claims description 23
230000002378 acidificating effect Effects 0.000 claims description 22
229920006318 anionic polymer Polymers 0.000 claims description 21
229920006317 cationic polymer Polymers 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 15
AWDYCSUWSUENQK-UHFFFAOYSA-N n-decylprop-2-enamide Chemical group CCCCCCCCCCNC(=O)C=C AWDYCSUWSUENQK-UHFFFAOYSA-N 0.000 claims description 10
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical group CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 8
125000002877 alkyl aryl group Chemical group 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical group CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
CEBFLGHPYLIZSC-UHFFFAOYSA-N n-benzyl-2-methylprop-2-enamide Chemical group CC(=C)C(=O)NCC1=CC=CC=C1 CEBFLGHPYLIZSC-UHFFFAOYSA-N 0.000 claims description 5
QQZXAODFGRZKJT-UHFFFAOYSA-N n-tert-butyl-2-methylprop-2-enamide Chemical group CC(=C)C(=O)NC(C)(C)C QQZXAODFGRZKJT-UHFFFAOYSA-N 0.000 claims description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
JGLVHRXGNNRXJI-UHFFFAOYSA-N dimethyl-[1-(2-methylprop-2-enoylamino)dodecyl]-propylazanium;chloride Chemical group [Cl-].CCCCCCCCCCCC(NC(=O)C(C)=C)[N+](C)(C)CCC JGLVHRXGNNRXJI-UHFFFAOYSA-N 0.000 claims description 2
FWFUWXVFYKCSQA-UHFFFAOYSA-M sodium;2-methyl-2-(prop-2-enoylamino)propane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C FWFUWXVFYKCSQA-UHFFFAOYSA-M 0.000 claims 14
150000008051 alkyl sulfates Chemical class 0.000 claims 4
229910052794 bromium Inorganic materials 0.000 claims 4
229910052740 iodine Inorganic materials 0.000 claims 4
JMWGZSWSTCGVLX-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methylprop-2-enoic acid Chemical group CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CCC(CO)(CO)CO JMWGZSWSTCGVLX-UHFFFAOYSA-N 0.000 claims 2
PTFJVMWIGQVPLR-UHFFFAOYSA-N dodecyl-dimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical group [Cl-].CCCCCCCCCCCC[N+](C)(C)CCCNC(=O)C(C)=C PTFJVMWIGQVPLR-UHFFFAOYSA-N 0.000 claims 2
125000005210 alkyl ammonium group Chemical group 0.000 claims 1
LBZCDAUUCOWSNH-UHFFFAOYSA-N hexadecyl-dimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical group [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CCCNC(=O)C(C)=C LBZCDAUUCOWSNH-UHFFFAOYSA-N 0.000 claims 1
238000005755 formation reaction Methods 0.000 abstract description 19
238000002360 preparation method Methods 0.000 abstract description 3
238000011084 recovery Methods 0.000 abstract description 2
239000000243 solution Substances 0.000 description 51
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
239000000839 emulsion Substances 0.000 description 20
238000006116 polymerization reaction Methods 0.000 description 20
238000000034 method Methods 0.000 description 19
239000007864 aqueous solution Substances 0.000 description 17
230000002209 hydrophobic effect Effects 0.000 description 17
239000003921 oil Substances 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
229920001577 copolymer Polymers 0.000 description 12
239000011780 sodium chloride Substances 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
238000007792 addition Methods 0.000 description 10
239000003999 initiator Substances 0.000 description 10
239000004094 surface-active agent Substances 0.000 description 10
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
230000014759 maintenance of location Effects 0.000 description 9
239000008096 xylene Substances 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 8
229920001897 terpolymer Polymers 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 6
XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 6
KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 6
FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000012530 fluid Substances 0.000 description 6
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
239000008367 deionised water Substances 0.000 description 5
229910021641 deionized water Inorganic materials 0.000 description 5
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 5
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
229940048053 acrylate Drugs 0.000 description 4
239000003963 antioxidant agent Substances 0.000 description 4
230000008901 benefit Effects 0.000 description 4
230000015556 catabolic process Effects 0.000 description 4
238000006731 degradation reaction Methods 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
239000005297 pyrex Substances 0.000 description 4
FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007762 w/o emulsion Substances 0.000 description 4
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 3
HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 3
VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 description 3
125000005396 acrylic acid ester group Chemical group 0.000 description 3
239000000654 additive Substances 0.000 description 3
229910001424 calcium ion Inorganic materials 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
230000001804 emulsifying effect Effects 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 3
125000001183 hydrocarbyl group Chemical group 0.000 description 3
125000005397 methacrylic acid ester group Chemical group 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000001593 sorbitan monooleate Substances 0.000 description 3
229940035049 sorbitan monooleate Drugs 0.000 description 3
235000011069 sorbitan monooleate Nutrition 0.000 description 3
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 2
HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 2
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-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
235000019738 Limestone Nutrition 0.000 description 2
JJFQHXBBKXGQGL-UHFFFAOYSA-N [Na].CC(C)(C)NC(=O)C=C Chemical compound [Na].CC(C)(C)NC(=O)C=C JJFQHXBBKXGQGL-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical class CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
229920006037 cross link polymer Polymers 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical class CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 2
JASXUJYZFNBTMF-UHFFFAOYSA-N dimethyl-[3-(2-methylprop-2-enoylamino)propyl]-octylazanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(C)CCCNC(=O)C(C)=C JASXUJYZFNBTMF-UHFFFAOYSA-N 0.000 description 2
UJKWLAZYSLJTKA-UHFFFAOYSA-N edma Chemical compound O1CCOC2=CC(CC(C)NC)=CC=C21 UJKWLAZYSLJTKA-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000006028 limestone Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229940088644 n,n-dimethylacrylamide Drugs 0.000 description 2
RULNGIPWAOXQFQ-UHFFFAOYSA-N n-(2-methylphenyl)prop-2-enamide Chemical compound CC1=CC=CC=C1NC(=O)C=C RULNGIPWAOXQFQ-UHFFFAOYSA-N 0.000 description 2
OHLHOLGYGRKZMU-UHFFFAOYSA-N n-benzylprop-2-enamide Chemical compound C=CC(=O)NCC1=CC=CC=C1 OHLHOLGYGRKZMU-UHFFFAOYSA-N 0.000 description 2
VQGWOOIHSXNRPW-UHFFFAOYSA-N n-butyl-2-methylprop-2-enamide Chemical compound CCCCNC(=O)C(C)=C VQGWOOIHSXNRPW-UHFFFAOYSA-N 0.000 description 2
YRVUCYWJQFRCOB-UHFFFAOYSA-N n-butylprop-2-enamide Chemical compound CCCCNC(=O)C=C YRVUCYWJQFRCOB-UHFFFAOYSA-N 0.000 description 2
YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 2
CNWVYEGPPMQTKA-UHFFFAOYSA-N n-octadecylprop-2-enamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)C=C CNWVYEGPPMQTKA-UHFFFAOYSA-N 0.000 description 2
GLVMTPQMPUWELB-UHFFFAOYSA-N n-pentylprop-2-enamide Chemical class CCCCCNC(=O)C=C GLVMTPQMPUWELB-UHFFFAOYSA-N 0.000 description 2
XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 2
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
230000035515 penetration Effects 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 2
WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229940047670 sodium acrylate Drugs 0.000 description 2
ROGLHGQOQFXWFW-UHFFFAOYSA-M sodium;2-(prop-2-enoylamino)ethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCNC(=O)C=C ROGLHGQOQFXWFW-UHFFFAOYSA-M 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 2
229920006029 tetra-polymer Polymers 0.000 description 2
JNYAEWCLZODPBN-KVTDHHQDSA-N (2r,3r,4r)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@@H](O)[C@H]1O JNYAEWCLZODPBN-KVTDHHQDSA-N 0.000 description 1
KFYRJJBUHYILSO-YFKPBYRVSA-N (2s)-2-amino-3-dimethylarsanylsulfanyl-3-methylbutanoic acid Chemical compound C[As](C)SC(C)(C)[C@@H](N)C(O)=O KFYRJJBUHYILSO-YFKPBYRVSA-N 0.000 description 1
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 1
FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 1
SMXYYZINIZFWMS-UHFFFAOYSA-M 1-prop-2-enylpyridin-1-ium;chloride Chemical compound [Cl-].C=CC[N+]1=CC=CC=C1 SMXYYZINIZFWMS-UHFFFAOYSA-M 0.000 description 1
BBZUXCYZFFZSRN-UHFFFAOYSA-N 18-methylnonadecyl-(4-methyl-3-oxopent-4-enyl)azanium;chloride Chemical compound [Cl-].CC(C)CCCCCCCCCCCCCCCCC[NH2+]CCC(=O)C(C)=C BBZUXCYZFFZSRN-UHFFFAOYSA-N 0.000 description 1
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
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LKZHPWDNRHKIQF-UHFFFAOYSA-M ethyl-dimethyl-(4-methyl-3-oxopent-4-enyl)azanium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CC[N+](C)(C)CCC(=O)C(C)=C LKZHPWDNRHKIQF-UHFFFAOYSA-M 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
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KUIRZTXKQKILAB-UHFFFAOYSA-M hexadecyl-dimethyl-(4-methyl-3-oxopent-4-enyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CCC(=O)C(C)=C KUIRZTXKQKILAB-UHFFFAOYSA-M 0.000 description 1
ZWGTVKDEOPDFGW-UHFFFAOYSA-N hexadecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[NH3+] ZWGTVKDEOPDFGW-UHFFFAOYSA-N 0.000 description 1
229920006158 high molecular weight polymer Polymers 0.000 description 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
229920000831 ionic polymer Polymers 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
HOEWZJZIQNSKPT-UHFFFAOYSA-M methyl sulfate;trimethyl-(4-methyl-3-oxopent-4-enyl)azanium Chemical compound COS([O-])(=O)=O.CC(=C)C(=O)CC[N+](C)(C)C HOEWZJZIQNSKPT-UHFFFAOYSA-M 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000003607 modifier Substances 0.000 description 1
WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 description 1
YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
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 1
SNPAMTGUOWHTMN-UHFFFAOYSA-N n-decyl-2-methylprop-2-enamide Chemical compound CCCCCCCCCCNC(=O)C(C)=C SNPAMTGUOWHTMN-UHFFFAOYSA-N 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
239000003129 oil well Substances 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
229960003330 pentetic acid Drugs 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
238000000710 polymer precipitation Methods 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229940096992 potassium oleate Drugs 0.000 description 1
MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
LLLCSBYSPJHDJX-UHFFFAOYSA-M potassium;2-methylprop-2-enoate Chemical compound [K+].CC(=C)C([O-])=O LLLCSBYSPJHDJX-UHFFFAOYSA-M 0.000 description 1
LRBUPFSFZKFAGU-UHFFFAOYSA-M potassium;3-(2-methylprop-2-enoylamino)propane-1-sulfonate Chemical compound [K+].CC(=C)C(=O)NCCCS([O-])(=O)=O LRBUPFSFZKFAGU-UHFFFAOYSA-M 0.000 description 1
FUDYQOGFKNNAAX-UHFFFAOYSA-M potassium;6-(prop-2-enoylamino)naphthalene-1-sulfonate Chemical compound [K+].C=CC(=O)NC1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 FUDYQOGFKNNAAX-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 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
229940035044 sorbitan monolaurate Drugs 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
238000003878 thermal aging Methods 0.000 description 1
230000008719 thickening Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000003567 thiocyanates Chemical class 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
ICKIMNNCJKMGAT-UHFFFAOYSA-M trimethyl(3-oxopent-4-enyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCC(=O)C=C ICKIMNNCJKMGAT-UHFFFAOYSA-M 0.000 description 1
VZTGWJFIMGVKSN-UHFFFAOYSA-O trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium Chemical compound CC(=C)C(=O)NCCC[N+](C)(C)C VZTGWJFIMGVKSN-UHFFFAOYSA-O 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1

Landscapes

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

CA000536061A 1986-05-19 1987-04-30 Compositions pour epaissir une solution acide Expired - Lifetime CA1302003C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US86420486A	1986-05-19	1986-05-19
US864,204		1986-05-19

Publications (1)

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CA1302003C true CA1302003C (fr)	1992-05-26

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Application Number	Title	Priority Date	Filing Date
CA000536061A Expired - Lifetime CA1302003C (fr)	1986-05-19	1987-04-30	Compositions pour epaissir une solution acide

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CA (1)	CA1302003C (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN109562042A (zh) *	2016-03-14	2019-04-02	Isp投资有限公司	一种用于角蛋白基质的包含调理、护色和定型聚合物的个人护理组合物
CN114181676A (zh) *	2021-06-30	2022-03-15	中国石油天然气集团有限公司	一种流型调节剂及其制备方法与深水水基恒流变钻井液

1987
- 1987-04-30 CA CA000536061A patent/CA1302003C/fr not_active Expired - Lifetime

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN109562042A (zh) *	2016-03-14	2019-04-02	Isp投资有限公司	一种用于角蛋白基质的包含调理、护色和定型聚合物的个人护理组合物
EP3522859A4 (fr) *	2016-03-14	2020-01-15	ISP Investments LLC	Composition de soin personnel pour substrat kératinique comprenant un polymère d'après-shampooing, de protection des couleurs et de coiffage
CN109562042B (zh) *	2016-03-14	2023-02-21	Isp投资有限公司	一种用于角蛋白基质的包含调理、护色和定型聚合物的个人护理组合物
CN114181676A (zh) *	2021-06-30	2022-03-15	中国石油天然气集团有限公司	一种流型调节剂及其制备方法与深水水基恒流变钻井液

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2003-05-26	MKLA	Lapsed

Publication	Publication Date	Title
US4959432A (en)	1990-09-25	Acid viscosifier compositions
EP0206489B1 (fr)	1991-03-13	Acrylamides N-substitués tolérants au calcium comme agents épaississants pour systèmes aqueux
US5089578A (en)	1992-02-18	Hydrophobically associating terpolymers containing sulfonate functionality
US4730028A (en)	1988-03-08	Process for preparing hydrophobically associating terpolymers containing sulfonate functionality
US4709759A (en)	1987-12-01	Enhanced oil recovery with hydrophobically associating polymers containing N-vinyl-pyrrolidone functionality
US4702319A (en)	1987-10-27	Enhanced oil recovery with hydrophobically associating polymers containing sulfonate functionality
US4889887A (en)	1989-12-26	Gelable acid viscosifiers
CA1267483A (fr)	1990-04-03	Production d'un melange de polymere soluble a l'eau
EP0226097B1 (fr)	1990-05-09	Composition hydrophobe associative contenant un polymère d'un monomère soluble dans l'eau et d'un monomère amphiphilique
US10526525B2 (en)	2020-01-07	Method for diverting an underground formation
US4463151A (en)	1984-07-31	Process for the formation of novel acrylamide acrylate copolymers
US4563290A (en)	1986-01-07	Water-soluble copolymers useful for enhanced oil recovery
CN1125094C (zh)	2003-10-22	一种耐温耐盐共聚物增稠剂
JPS61500444A (ja)	1986-03-13	疎水性に会合するポリマ−の油中水形エマルジョン及びその製造方法
US7696304B2 (en)	2010-04-13	Thermally stable water-soluble polymer which is crosslinkable at high temperatures
US4650848A (en)	1987-03-17	Terpolymers of acrylamide, alkylacrylamide and betaine monomers
WO2002102917A2 (fr)	2002-12-27	Solutions de polymeres presentant des proprietes de cisaillement reversible
US4690219A (en)	1987-09-01	Acidizing using n-vinyl lactum/unsaturated amide copolymers
US5100953A (en)	1992-03-31	Solutions of hydrophobically associating terpolymers containing sulfonate functionality
US4742135A (en)	1988-05-03	Terpolymers of acrylamide, alkylacrylamide and betaine monomers
US4463152A (en)	1984-07-31	Acrylamide acrylate copolymers
US4584358A (en)	1986-04-22	Calcium-tolerant N-substituted acrylamides as thickeners for aqueous systems
CA1326731C (fr)	1994-02-01	Terpolymeres a poids moleculaire eleve d'acrylamide, d'acide acrylique ou d'alkylacrylamide
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