CN118085844A - Preparation method of cross-linking agent for high-temperature-resistant cross-linking acid - Google Patents
Preparation method of cross-linking agent for high-temperature-resistant cross-linking acid Download PDFInfo
- Publication number
- CN118085844A CN118085844A CN202211491730.7A CN202211491730A CN118085844A CN 118085844 A CN118085844 A CN 118085844A CN 202211491730 A CN202211491730 A CN 202211491730A CN 118085844 A CN118085844 A CN 118085844A
- Authority
- CN
- China
- Prior art keywords
- acid
- cross
- temperature
- cucurbituril
- ligand
- 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.)
- Pending
Links
- 239000002253 acid Substances 0.000 title claims abstract description 62
- 238000004132 cross linking Methods 0.000 title claims abstract description 53
- 239000003431 cross linking reagent Substances 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title claims abstract description 33
- 239000003446 ligand Substances 0.000 claims abstract description 37
- 239000000178 monomer Substances 0.000 claims abstract description 33
- MSBXTPRURXJCPF-DQWIULQBSA-N cucurbit[6]uril Chemical group N1([C@@H]2[C@@H]3N(C1=O)CN1[C@@H]4[C@@H]5N(C1=O)CN1[C@@H]6[C@@H]7N(C1=O)CN1[C@@H]8[C@@H]9N(C1=O)CN([C@H]1N(C%10=O)CN9C(=O)N8CN7C(=O)N6CN5C(=O)N4CN3C(=O)N2C2)C3=O)CN4C(=O)N5[C@@H]6[C@H]4N2C(=O)N6CN%10[C@H]1N3C5 MSBXTPRURXJCPF-DQWIULQBSA-N 0.000 claims abstract description 22
- 229920000642 polymer Polymers 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000008367 deionised water Substances 0.000 claims description 19
- 229910021641 deionized water Inorganic materials 0.000 claims description 19
- 125000000129 anionic group Chemical group 0.000 claims description 17
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
- 239000002994 raw material Substances 0.000 claims description 11
- 239000011521 glass Substances 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 8
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 8
- 150000003755 zirconium compounds Chemical class 0.000 claims description 8
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 7
- 239000004310 lactic acid Substances 0.000 claims description 7
- 235000014655 lactic acid Nutrition 0.000 claims description 7
- CMOAHYOGLLEOGO-UHFFFAOYSA-N oxozirconium;dihydrochloride Chemical compound Cl.Cl.[Zr]=O CMOAHYOGLLEOGO-UHFFFAOYSA-N 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000174 gluconic acid Substances 0.000 claims description 4
- 235000012208 gluconic acid Nutrition 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- 239000004971 Cross linker Substances 0.000 claims description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 3
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- MSBXTPRURXJCPF-UHFFFAOYSA-N cucurbituril Chemical compound O=C1N(CN2C(=O)N3CN4C(=O)N5CN6C(=O)N7CN8C(=O)N9C%10)C%11N(C%12=O)CN(C%13=O)C2C3N%13CN(C2=O)C4C5N2CN(C2=O)C6C7N2CN(C2=O)C8C9N2CN2C(=O)N3C4C2N%10C(=O)N4CN1C%11N%12C3 MSBXTPRURXJCPF-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims description 3
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 2
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- ZDOBFUIMGBWEAB-UHFFFAOYSA-N cucurbit[7]uril Chemical compound O=C1N(CN2C(=O)N3CN4C(=O)N5CN6C(=O)N7CN8C(=O)N9CN%10C(=O)N%11C%12)C%13N(C%14=O)CN(C%15=O)C2C3N%15CN(C2=O)C4C5N2CN(C2=O)C6C7N2CN(C2=O)C8C9N2CN(C2=O)C%10C%11N2CN2C(=O)N3C4C2N%12C(=O)N4CN1C%13N%14C3 ZDOBFUIMGBWEAB-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 claims description 2
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims description 2
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 2
- 229960003330 pentetic acid Drugs 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 11
- 239000002562 thickening agent Substances 0.000 abstract description 16
- 229910021645 metal ion Inorganic materials 0.000 abstract description 12
- 230000009471 action Effects 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- 230000020477 pH reduction Effects 0.000 abstract description 4
- 238000010008 shearing Methods 0.000 abstract description 4
- 238000012360 testing method Methods 0.000 abstract description 2
- 150000002978 peroxides Chemical class 0.000 abstract 1
- -1 zirconium ions Chemical class 0.000 description 7
- 238000011161 development Methods 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000013110 organic ligand Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000010276 construction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- VYJWAACGBWHAEO-UHFFFAOYSA-L P(OC(CO)OP([O-])=O)([O-])=O.[Na+].[Na+] Chemical compound P(OC(CO)OP([O-])=O)([O-])=O.[Na+].[Na+] VYJWAACGBWHAEO-UHFFFAOYSA-L 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 229960001484 edetic acid Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 230000000979 retarding effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 150000003754 zirconium Chemical class 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- DZSVIVLGBJKQAP-UHFFFAOYSA-N 1-(2-methyl-5-propan-2-ylcyclohex-2-en-1-yl)propan-1-one Chemical compound CCC(=O)C1CC(C(C)C)CC=C1C DZSVIVLGBJKQAP-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical group [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 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
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention provides a preparation method of a cross-linking agent for high-temperature-resistant cross-linking acid, and relates to the technical field of oilfield chemistry. The polymer containing cucurbituril units is prepared by copolymerizing cucurbituril with water-soluble monomers under the action of peroxide to form free radicals, and the free radicals are used as high-valence metal ion polymer ligands. Through tests, the product has good crosslinking effect on the conventional crosslinking acid thickener, and the formed crosslinking acid system can still keep good viscosity under the high-temperature and shearing effects, so that the product can be suitable for the high-temperature acidification operation at 180 ℃.
Description
Technical Field
The invention relates to the technical field of oilfield chemistry, in particular to a preparation method of a cross-linking agent for high-temperature-resistant cross-linking acid.
Background
Petroleum is the most widely used energy source in the world at present, and the use advantages and basic effects of petroleum are still not replaced in a future period. The carbonate strata in China are widely distributed, so that the development of carbonate reservoirs is enlarged, and the supply of oil and gas resources can be effectively ensured. For carbonate reservoir development, acidizing fracturing has unique advantages, and the acid fracturing technology can not only be used for connecting natural cracks of a reservoir through fracturing, but also form acid etching cracks, so that the heterogeneity of the reservoir is effectively improved, and high-diversion cracks of oil gas are formed. Therefore, the acidification technology is widely applied to carbonate reservoirs, and a good effect is achieved.
The cross-linking acid is one of important working fluids in acid fracturing construction, and refers to a system with an intermolecular three-dimensional network structure formed by the action of a cross-linking agent of a thickener in acid liquor. The formation of the cross-linking structure can effectively improve the viscosity of an acid liquor system, and enhance the performances of the acid liquor system such as temperature resistance, shearing resistance, sand carrying, retarding and the like, thereby realizing the purposes of reducing formation damage, increasing the acid etching action distance, realizing deep acidification of the formation and improving the oil gas yield. In a conventional cross-linking acid system, the thickener is usually an acrylamide polymer, the cross-linking agent is usually an organic metal ion compound, and high-valence metal ions in the cross-linking agent realize cross-linking through forming coordination with carboxyl groups, amide groups and other groups in the thickener. The cross-linking agent plays a decisive role in the formation and strength of the intermolecular network structure of the thickener, so that the performance of a cross-linking acid system can be improved by improving the molecular structure of the cross-linking agent.
As petroleum development proceeds deeper, the requirements of the mine for the temperature resistance of the crosslinked acid system are continuously raised. However, the current commercial cross-linking acid systems are often only suitable for reservoir conditions of 140 ℃ and below, and lack cross-linking acid systems which can be used at 160-180 ℃ in field construction. The temperature is increased, so that on one hand, the thickener molecules are curled, the size of the molecules is reduced, and the distance between the molecules is increased, and therefore intermolecular crosslinking is more difficult to occur; on the other hand, the hydrated structure of the crosslinking agent may be destroyed, and the coordination between the crosslinking agent and the thickener becomes weaker, resulting in weakening of the crosslinked structure. Therefore, developing a multi-site and multi-size cross-linking agent, improving the stability of the coordination structure of the cross-linking agent and the thickener at high temperature, is one of the important ways to improve the high temperature resistance of the cross-linking acid.
In the prior art, a complex formed by high-valence metal ions, typically zirconium ions and titanium ions, and organic ligands, typically polyalcohols, polyacids, polyphosphonic acids and other compounds, are generally used as a crosslinking agent of crosslinking acid. The organic ligand is added mainly to control the concentration of free metal ions in the crosslinking acid system, so as to realize uniform crosslinking and delayed crosslinking.
For example, chinese patent CN111500274 a discloses an organozirconium cross-linking agent, cross-linking acid sand-carrying fluid and preparation method, which is prepared from inorganic zirconium salt (6% -9%), organic acid (3% -6%), and organic ligand (10% -15%) as raw materials, wherein the inorganic zirconium salt is zirconium oxychloride and zirconium chloride, the organic acid is sulfamic acid, oxalic acid, sulfamic acid, and the organic ligand is disodium hydroxyethylidene bisphosphonate, sodium hydroxyethylidene bisphosphonate, or tetrasodium hydroxyethylidene bisphosphonate. Chinese patent CN111117593 a discloses a cross-linking agent and its preparation method, which is prepared from zirconium oxychloride (10% -15%), organic carboxylic acid (15% -30%), anionic surfactant (3% -15%), polyalcohol/polyalcohol amine (15% -30%), wherein the organic carboxylic acid is lactic acid, citric acid, tartaric acid, gluconic acid, malic acid, oxalic acid, the anionic surfactant is sodium dodecyl benzene sulfonate, sodium dodecyl sulfate, sodium dodecyl sulfonate, sodium dodecyl alcohol polyoxyethylene ether sulfate, ammonium dodecyl sulfate, and the polyalcohol/polyalcohol amine is glycerol, ethylene glycol, triethanolamine, diethanolamine, xylitol, sorbitol, pentaerythritol. Literature (Luo Mingliang. Performance of environmentally friendly crosslinked acid and reaction kinetics [ J ]. Fine chemical engineering, 2020,37 (4): 834-840), which adopts lactic acid, gluconic acid, polyethyleneimine and polyacrylamide thickener as main raw materials, and adopts a solution blending method to prepare the environmentally friendly high temperature resistant crosslinked acid. The three-dimensional network structure formed by the cross-linking agent and the thickening agent ensures that the system has good temperature resistance and shearing resistance, the cross-linking acid is even in gel breaking, no residue exists, the cross-linking acid has good retarding performance, and the effective acting distance of the acid liquor is prolonged. Literature (good house. Development of novel high temperature resistant cross-linked acid and performance evaluation [ J ]. Broken block oil and gas field, 201825 (6): 815-818), takes acrylamide, acrylic acid, vinyl pyrrolidone, 2-acrylamide-2-methylpropanesulfonic acid and the like as raw materials, and synthesizes a thickening agent; zirconium oxychloride, isopropanol, polyalcohol, sodium polyhydroxycarboxylate and the like are taken as raw materials to synthesize an organozirconium crosslinking agent; and optimizing and obtaining the formula of the high-temperature-resistant cross-linked acid system.
In summary, the crosslinking agents for crosslinking acids are reported to be mostly prepared from organic small molecule ligands and high-valence metal ions, and the coordination strength of the ligands and the metal ions is improved by the combination of different small molecule ligands through the change of the types, the number and the combination of the functional groups of the small molecule ligands. Although the changes can control the concentration of free metal ions in the cross-linked acid system and change the interaction mode between the metal ions and thickener molecules, under the high temperature condition, the coordination action between small molecule ligands and the metal ions is greatly weakened, and stable network structures are difficult to form through the cross-linking action of the metal ions among different thickener molecules, so that the finally formed cross-linked acid system is difficult to meet the requirements of high temperature oil reservoir acidizing construction.
Therefore, the existing crosslinking agent still has a larger improvement space in performance, and development of high-temperature-resistant crosslinking acid is developed, so that positive effects are certainly generated on development of high-temperature carbonate reservoirs.
Disclosure of Invention
Based on the large dosage of the organic ligand in the prior art, the effective content of high-valence metal ions in the cross-linking agent is low; the application aims to provide a preparation method of a crosslinking agent for high-temperature-resistant crosslinking acid, which grafts a water-soluble monomer on cucurbiturils to form a polymer and improves the temperature resistance of a crosslinking acid system from 140 ℃ to 180 ℃.
In order to achieve the above purpose, the application is realized by adopting the following technical scheme:
a preparation method of a cross-linking agent for high-temperature-resistant cross-linking acid comprises the following steps:
(1) Preparation of polymeric ligands
(1.1) Dissolving nonionic water-soluble monomers and anionic water-soluble monomers in deionized water to prepare a monomer solution with the concentration of 200 g/L;
(1.2) adding cucurbituril, persulfate and deionized water into a three-necked glass bottle provided with a stirrer, a nitrogen pipe and a thermometer, stirring until all raw materials are dissolved, introducing nitrogen for 30min, raising the temperature to 50-100 ℃, and reacting for 0.5-6h;
(1.3) then adding the monomer solution prepared in the step (1.1) into a three-necked glass bottle prepared in the step (1.2), reacting for 3-24 hours at the temperature of 70-100 ℃, drying and crushing the product to obtain the catalyst;
(2) Preparation of the crosslinker
Adding inorganic zirconium compound, nonionic ligand, anionic ligand, macromolecular ligand and deionized water into a three-necked glass bottle provided with a stirrer, a condenser tube and a thermometer, stirring until all raw materials are dissolved, adding ammonia water to adjust the pH value to 2-8, raising the temperature to 40-80 ℃, and reacting for 1-10h to obtain the nano-zirconia.
The mass ratio of the nonionic water-soluble monomer to the anionic water-soluble monomer in the step (1.1) is 1: (0.01-0.8);
preferably, the mass ratio of the nonionic water-soluble monomer to the anionic water-soluble monomer is 1:
(0.01-0.35)；
Wherein,
The nonionic water-soluble monomer is selected from one or more of acrylamide, vinyl pyrrolidone, vinyl caprolactam, methacrylamide, N-methylol acrylamide, N-ethylacrylamide, N-dimethylacrylamide, N-diethylacrylamide, N-isopropylacrylamide, hydroxyethyl acrylate and hydroxypropyl acrylate;
the anionic water-soluble monomer is one or more selected from acrylic acid, methacrylic acid, maleic acid and itaconic acid.
The mass ratio of the cucurbituril, the persulfate and the deionized water in the step (1.2) is 1: (0.2-3): (10-100);
Preferably, the mass ratio of cucurbituril, persulfate and deionized water is 1: (0.6-2): (30-70);
Wherein,
The cucurbituril is one of cucurbituril [6], cucurbituril [7] or cucurbituril [8 ].
The persulfate is selected from one or more of potassium persulfate, sodium persulfate and ammonium persulfate.
The mass ratio of the monomer solution to the cucurbituril in the step (1.3) is (2-50): 1, a step of;
Preferably, the mass ratio of the monomer solution to the cucurbituril is (5-25): 1.
As a preferable technical scheme, the temperature in the step (1.2) is 60-90 ℃ and the time is 0.5-3h; the temperature in the step (1.3) is 70-90 ℃ and the time is 6-18h.
The mass ratio of the inorganic zirconium compound, the nonionic ligand, the anionic ligand, the macromolecular ligand and the deionized water in the step (2) is 1: (0.2-3): (0.1-2): (0.02-0.8): (1-7);
preferably, the mass ratio of the inorganic zirconium compound to the nonionic ligand to the anionic ligand to the polymer ligand to the deionized water is 1: (0.5-2): (0.1-0.6): (0.05-0.4): (2.5-7).
Wherein,
The inorganic zirconium compound is one of zirconium oxychloride or zirconium chloride;
The nonionic ligand is one or more of ethanol, propanol, isopropanol, glycerol, pentaerythritol, ethanolamine, diethanolamine and triethanolamine;
The anionic ligand is one or more of oxalic acid, malonic acid, succinic acid, glycolic acid, lactic acid, hydroxybutyric acid, amino acid, gluconic acid, citric acid, nitrilotriacetic acid, ethylenediamine tetraacetic acid and diethylenetriamine pentaacetic acid;
as a preferable technical scheme, the pH in the step (2) is 3-6, the temperature is 45-70 ℃ and the time is 2-8h.
Compared with the prior art, the application has the beneficial effects that:
(1) Grafting a water-soluble monomer on cucurbituril to form a polymer, and loading zirconium ions on the polymer to prepare a high molecular cross-linking agent by utilizing the strong coordination effect of the cucurbituril on the zirconium ions to form a multi-site cross-linking structure, so that the consumption of a thickening agent and a cross-linking agent in a cross-linking acid system is reduced;
(2) The cucurbituril has the size of about 1nm, and both ends can coordinate with zirconium ions, so that nano-size crosslinking can be realized, and the crosslinking efficiency is improved;
(3) The cucurbituril has excellent heat stability and rigidity, and improves the temperature resistance of a cross-linked acid system from 140 ℃ to 180 ℃.
Detailed Description
The experimental methods used in the following examples are conventional methods unless otherwise specified.
The cross-linking acid agents used in the examples described below, including thickeners, corrosion inhibitors, high temperature stabilizers, etc., were purchased from the general petrochemical company, inc. of Puyang, and other materials, reagents, etc., were commercially available unless otherwise specified.
The present invention will be further described with reference to the following examples, but the scope of the present invention is not limited thereto.
Example 1 preparation method of Cross-linking agent for high temperature Cross-linking acid
The method comprises the following steps:
(1) Preparation of polymeric ligands
(1.1) Dissolving 100g of acrylamide and 20g of acrylic acid in deionized water to prepare a monomer solution with the concentration of 200 g/L;
(1.2) adding 10g of cucurbituril [6], 12g of potassium persulfate and 400g of deionized water into a three-necked glass bottle provided with a stirrer, a nitrogen pipe and a thermometer, stirring until all raw materials are dissolved, introducing nitrogen for 30min, raising the temperature to 70 ℃, and reacting for 1h;
(1.3) adding 100g of monomer solution into a three-necked glass bottle, adjusting the temperature to 80 ℃, reacting for 10 hours, drying and crushing the product to obtain a high molecular ligand;
(2) Preparation of the crosslinker
10G of zirconium oxychloride, 10g of diethanolamine, 3g of lactic acid, 1g of a high molecular ligand and 60g of deionized water are added into a three-necked glass bottle provided with a stirrer, a condenser tube and a thermometer, after all raw materials are stirred and dissolved, ammonia water is added to adjust the pH value to 3.5, the temperature is increased to 60 ℃, and the reaction is carried out for 5 hours, thus obtaining the cross-linking agent.
Example 2 preparation method of Cross-linking agent for high temperature Cross-linking acid
The procedure is as in example 1, except that the acrylic acid is added in an amount of 10g.
Example 3 preparation method of Cross-linking agent for high temperature Cross-linking acid
The procedure is as in example 1, except that the acrylic acid is added in an amount of 30g.
Example 4 preparation method of Cross-linking agent for high temperature Cross-linking acid
The non-ionic water soluble monomer was N-methylolacrylamide as described in example 1.
Example 5 preparation method of Cross-linking agent for high temperature Cross-linking acid
The non-ionic water soluble monomers were 75g acrylamide and 25g N, N-dimethylacrylamide as described in example 1.
Example 6 preparation method of Cross-linking agent for high temperature Cross-linking acid
The procedure is as in example 1, except that the potassium persulfate is added in an amount of 8g.
Example 7 preparation method of Cross-linking agent for high temperature Cross-linking acid
The procedure is as in example 1, except that the potassium persulfate is added in an amount of 18g.
Example 8 preparation method of Cross-linking agent for high temperature Cross-linking acid
As described in example 1, except that deionized water was added in an amount of 550g.
Example 9 preparation method of Cross-linking agent for high temperature Cross-linking acid
The procedure is as in example 1, except that the monomer solution is added in an amount of 200g.
Example 10 preparation method of Cross-linking agent for high temperature Cross-linking acid
The procedure is as in example 1, except that the cucurbituril of step (1) is reacted with potassium persulfate at 80℃for 0.5h; the cucurbituril reacts with the monomer at 80 ℃ for 8 hours.
Example 11 preparation method of Cross-linking agent for high temperature Cross-linking acid
As described in example 1, except that the amount of diethanolamine added in step (2) was 15g.
Example 12 preparation method of Cross-linking agent for high temperature Cross-linking acid
As described in example 1, except that the nonionic ligand in step (2) was 5g diethanolamine and 5g glycerol.
Example 13 preparation method of Cross-linking agent for high temperature Cross-linking acid
As described in example 1, except that the anionic ligand in step (2) was 3g lactic acid and 2g ethylene diamine tetraacetic acid.
Example 14 preparation method of Cross-linking agent for high temperature Cross-linking acid
The procedure is as in example 1, except that the macromolecular ligand is added in an amount of 0.5g in step (2).
Example 15 preparation method of Cross-linking agent for high temperature Cross-linking acid
The procedure is as in example 1, except that the amount of the polymeric ligand added in step (2) is 3.5g.
Example 16 preparation method of Cross-linking agent for high temperature Cross-linking acid
The procedure is as in example 1, except that in step (2) the reaction pH is 5.5, the temperature is 70℃and the time is 3 hours.
Comparative example 1
Adding 10g of zirconium oxychloride, 10g of diethanolamine, 3g of lactic acid and 60g of deionized water into a three-necked glass bottle provided with a stirrer, a condenser tube and a thermometer, stirring until all raw materials are dissolved, adding ammonia water to adjust the pH to 3.5, raising the temperature to 60 ℃, and reacting for 5 hours to obtain the product.
Comparative example 2
And GL-3, a cross-linking agent of Lipuidambaris petrochemical Co.
Evaluation of Performance
The rheological properties of the crosslinked acids prepared in the products of comparative examples and examples 1 to 16 at high temperature were evaluated, and the apparent viscosities were measured after shearing for 90min at high temperature of 170s -1 as prescribed in SY/T5107-2016 water-based fracturing fluid evaluation method, the test temperatures were 140 ℃,160 ℃ and 180 ℃, the compositions of the crosslinked acid systems were as shown below, and the evaluation results are shown in Table 1.
The formula of the cross-linking acid system comprises: 400g of hydrochloric acid (20%) +3.2g of thickener+8 g of cross-linking agent+8 g of corrosion inhibitor+4 g of corrosion inhibition synergist+10 g of high temperature stabilizer+6 g of iron ion stabilizer.
Table 1 results of performance evaluation
As can be seen from the data in Table 1, the cross-linking acid prepared by using the cross-linking agent has better high-temperature stability and can meet the requirement of 180 ℃ acidification construction.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, various simple variants of the technical solution of the invention can be made, including combinations of the individual technical features in any other suitable way, which simple variants and combinations should likewise be regarded as being disclosed by the invention, all falling within the scope of protection of the invention.
Claims (14)
1. A preparation method of a cross-linking agent for high-temperature-resistant cross-linking acid is characterized by comprising the following steps: the method comprises the following steps:
(1) Preparation of polymeric ligands
(1.1) Dissolving nonionic water-soluble monomers and anionic water-soluble monomers in deionized water to prepare a monomer solution with the concentration of 200 g/L;
(1.2) adding cucurbituril, persulfate and deionized water into a three-necked glass bottle provided with a stirrer, a nitrogen pipe and a thermometer, stirring until all raw materials are dissolved, introducing nitrogen for 30min, raising the temperature to 50-100 ℃, and reacting for 0.5-6h;
(1.3) then adding the monomer solution prepared in the step (1.1) into a three-necked glass bottle prepared in the step (1.2), reacting for 3-24 hours at the temperature of 70-100 ℃, drying and crushing the product to obtain the catalyst;
(2) Preparation of the crosslinker
Adding inorganic zirconium compound, nonionic ligand, anionic ligand, macromolecular ligand and deionized water into a three-necked glass bottle provided with a stirrer, a condenser tube and a thermometer, stirring until all raw materials are dissolved, adding ammonia water to adjust the pH value to 2-8, raising the temperature to 40-80 ℃, and reacting for 1-10h to obtain the nano-zirconia.
2. The method of manufacturing according to claim 1, characterized in that: the mass ratio of the nonionic water-soluble monomer to the anionic water-soluble monomer in the step (1.1) is 1: (0.01-0.8).
3. The preparation method according to claim 2, characterized in that: the mass ratio of the nonionic water-soluble monomer to the anionic water-soluble monomer in the step (1.1) is 1 (0.01-0.35).
4. A method of preparation according to claim 3, characterized in that:
The nonionic water-soluble monomer is selected from one or more of acrylamide, vinyl pyrrolidone, vinyl caprolactam, methacrylamide, N-methylol acrylamide, N-ethylacrylamide, N-dimethylacrylamide, N-diethylacrylamide, N-isopropylacrylamide, hydroxyethyl acrylate and hydroxypropyl acrylate;
the anionic water-soluble monomer is one or more selected from acrylic acid, methacrylic acid, maleic acid and itaconic acid.
5. The method of manufacturing according to claim 1, characterized in that: the mass ratio of cucurbituril, persulfate and deionized water in the step (1.2) is 1: (0.2-3): (10-100).
6. The method of manufacturing according to claim 5, wherein: the mass ratio of cucurbituril, persulfate and deionized water in the step (1.2) is 1: (0.6-2): (30-70).
7. The method of manufacturing according to claim 6, wherein: the cucurbituril in the step (1.2) is one of cucurbituril [6], cucurbituril [7] or cucurbituril [8 ];
The persulfate is selected from one or more of potassium persulfate, sodium persulfate and ammonium persulfate.
8. The method of manufacturing according to claim 1, characterized in that: the mass ratio of the monomer solution to the cucurbituril in the step (1.3) is (2-50): 1.
9. The method of manufacturing according to claim 8, wherein: the mass ratio of the monomer solution to the cucurbituril is (5-25): 1.
10. The method of manufacturing according to claim 1, characterized in that: the temperature in the step (1.2) is 60-90 ℃ and the time is 0.5-3h; the temperature in the step (1.3) is 70-90 ℃ and the time is 6-18h.
11. The method of manufacturing according to claim 1, characterized in that: the mass ratio of the inorganic zirconium compound, the nonionic ligand, the anionic ligand, the macromolecular ligand and the deionized water in the step (2) is 1: (0.2-3): (0.1-2): (0.02-0.8): (1-7).
12. The method of manufacturing according to claim 11, wherein: the mass ratio of the inorganic zirconium compound to the nonionic ligand to the anionic ligand to the polymer ligand to the deionized water is 1: (0.5-2): (0.1-0.6): (0.05-0.4): (2.5-7).
13. The method of manufacturing according to claim 12, wherein: the inorganic zirconium compound is one of zirconium oxychloride or zirconium chloride;
The nonionic ligand is one or more of ethanol, propanol, isopropanol, glycerol, pentaerythritol, ethanolamine, diethanolamine and triethanolamine;
The anionic ligand is one or more of oxalic acid, malonic acid, succinic acid, glycolic acid, lactic acid, hydroxybutyric acid, amino acid, gluconic acid, citric acid, nitrilotriacetic acid, ethylenediamine tetraacetic acid and diethylenetriamine pentaacetic acid.
14. The method of manufacturing according to claim 1, characterized in that: the pH value in the step (2) is 3-6, the temperature is 45-70 ℃ and the time is 2-8h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211491730.7A CN118085844A (en) | 2022-11-25 | 2022-11-25 | Preparation method of cross-linking agent for high-temperature-resistant cross-linking acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211491730.7A CN118085844A (en) | 2022-11-25 | 2022-11-25 | Preparation method of cross-linking agent for high-temperature-resistant cross-linking acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN118085844A true CN118085844A (en) | 2024-05-28 |
Family
ID=91140872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211491730.7A Pending CN118085844A (en) | 2022-11-25 | 2022-11-25 | Preparation method of cross-linking agent for high-temperature-resistant cross-linking acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN118085844A (en) |
-
2022
- 2022-11-25 CN CN202211491730.7A patent/CN118085844A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2002241704A1 (en) | Polymeric fluid loss additives and method of use thereof | |
| CN109763127B (en) | Quick dissolving solution for soluble bridge plug and preparation method thereof | |
| US4487867A (en) | Water soluble anionic polymer composition and method for stimulating a subterranean formation | |
| CN112358864B (en) | Nano emulsion acid system and preparation method and application thereof | |
| CN106753315A (en) | A kind of temperature control type becomes mucic acid and preparation method thereof | |
| CN108690597A (en) | A kind of slippery water fracturing fluid | |
| CN111349426B (en) | Diverting acid, preparation method and application thereof | |
| CA1211880A (en) | Method of improving dispersibility of water soluble anionic polymers | |
| CN111876138B (en) | Carbon-based tackifier and preparation method and application thereof | |
| CN116751337B (en) | Thickening agent for acidizing fracturing and synthesis method thereof | |
| CN109575904B (en) | Seawater-based fracturing fluid and preparation method and application thereof | |
| CN118085844A (en) | Preparation method of cross-linking agent for high-temperature-resistant cross-linking acid | |
| CN110982507B (en) | Acid liquid thickener for acid fracturing and preparation method and application thereof | |
| WO2018086984A1 (en) | Process for increasing the production of hydrocarbons from hydrocarbon bearing reservoirs | |
| CN111961459A (en) | Gel acid system for acidification and preparation method thereof | |
| WO2015042028A1 (en) | High temperature stable cross-linked polymers | |
| CN110713570A (en) | Temperature-sensitive type acid thickener for acidizing and fracturing and preparation method thereof | |
| CN107619660B (en) | Gelled acid thickener and preparation method thereof | |
| CN112143479B (en) | Non-flowback stamping acidification system for water injection well of low-permeability reservoir and preparation method | |
| CN110373175A (en) | Seawater-based fracturing fluid crosslinking agent and fracturing fluid and preparation method | |
| Li et al. | Synthesis and performance of temperature-and acid-resistant ternary-copolymer thickener | |
| CN115260414B (en) | Modified polyacrylamide acid thickener and preparation method thereof | |
| CN116082539A (en) | High-temperature-resistant modified polyvinyl alcohol and preparation method and application thereof | |
| CN114437487B (en) | Instant polyacrylamide composition and preparation method and application thereof | |
| CN113897191B (en) | Paste-containing reservoir fracturing fluid modifier and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination |