CN117430748A - Emulsion type hydrophobically associating polyacrylamide thickener and preparation process thereof - Google Patents
Emulsion type hydrophobically associating polyacrylamide thickener and preparation process thereof Download PDFInfo
- Publication number
- CN117430748A CN117430748A CN202311757812.6A CN202311757812A CN117430748A CN 117430748 A CN117430748 A CN 117430748A CN 202311757812 A CN202311757812 A CN 202311757812A CN 117430748 A CN117430748 A CN 117430748A
- Authority
- CN
- China
- Prior art keywords
- acrylamide
- emulsion type
- hydrophobically associating
- polyacrylamide thickener
- cardanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002562 thickening agent Substances 0.000 title claims abstract description 54
- 229920002401 polyacrylamide Polymers 0.000 title claims abstract description 51
- 239000000839 emulsion Substances 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 60
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 50
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 36
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 claims description 36
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 claims description 35
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 claims description 35
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 claims description 35
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 244000226021 Anacardium occidentale Species 0.000 claims description 30
- 235000020226 cashew nut Nutrition 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 29
- 239000000178 monomer Substances 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000012074 organic phase Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- 238000003756 stirring Methods 0.000 claims description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- 230000002209 hydrophobic effect Effects 0.000 claims description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 13
- 239000003995 emulsifying agent Substances 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 13
- -1 amidine hydrochloride Chemical class 0.000 claims description 12
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000012071 phase Substances 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 9
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 9
- 229940106681 chloroacetic acid Drugs 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 238000001556 precipitation Methods 0.000 claims description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 7
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 7
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 7
- 229960001124 trientine Drugs 0.000 claims description 7
- ASBJGPTTYPEMLP-UHFFFAOYSA-N 3-chloroalanine Chemical compound ClCC(N)C(O)=O ASBJGPTTYPEMLP-UHFFFAOYSA-N 0.000 claims description 6
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 6
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 6
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims description 6
- 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 claims description 5
- IVKNZCBNXPYYKL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 IVKNZCBNXPYYKL-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 5
- 230000035484 reaction time Effects 0.000 claims 2
- 239000003921 oil Substances 0.000 abstract description 24
- 239000010779 crude oil Substances 0.000 abstract description 11
- 238000011084 recovery Methods 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 7
- 239000011148 porous material Substances 0.000 abstract description 4
- 238000000502 dialysis Methods 0.000 abstract description 3
- 239000003208 petroleum Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 238000000605 extraction Methods 0.000 description 13
- GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 238000010008 shearing Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 238000005213 imbibition Methods 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 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 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229920001558 organosilicon polymer Polymers 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229940047670 sodium acrylate Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/66—Compositions based on water or polar solvents
- C09K8/68—Compositions based on water or polar solvents containing organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/84—Compositions based on water or polar solvents
- C09K8/86—Compositions based on water or polar solvents containing organic compounds
- C09K8/88—Compositions based on water or polar solvents containing organic compounds macromolecular compounds
- C09K8/882—Compositions based on water or polar solvents containing organic compounds macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention relates to the technical field of petroleum exploitation and discloses an emulsion type hydrophobically associating polyacrylamide thickener and a preparation process thereof. The method can be suitable for high-temperature complex environments of low-permeability oil reservoir exploitation. The interfacial tension between the hydrophobically associating polyacrylamide thickener solution and the crude oil simulated oil is lower, and when the interfacial tension between the thickener solution and the crude oil in the core is lower in the actual oil reservoir exploitation process, the resistance generated when crude oil drops pass through the core pore canal can be reduced, and the crude oil drops are promoted to flow out of the core pore canal, so that the dialysis recovery ratio is improved.
Description
Technical Field
The invention relates to the technical field of petroleum exploitation, in particular to an emulsion type hydrophobically associating polyacrylamide thickener and a preparation process thereof.
Background
In the actual exploitation process of the low-permeability reservoir, residual oil with higher reserve exists, so that the recovery ratio of the low-permeability reservoir needs to be improved, and the recovery ratio can be effectively improved by adopting the thickening fracturing fluid with the polyacrylamide as a matrix. However, the polyacrylamide thickener has poor temperature resistance, is easy to thermally decompose at high temperature, has poor shearing resistance and has low recovery ratio to a hypotonic oil reservoir.
Long-chain hydrophobic monomers are introduced into the thickener to form a hydrophobic association polymer, so that the thickening, temperature resistance, shearing resistance and other performances of the thickener can be effectively improved; chinese patent No. 115215965B discloses that acrylamide, sodium acrylate, arene prepolymer, organosilicon polymer monomer, hydrophobic monomer and the like are polymerized to prepare the hydrophobic association type fracturing thickener which has excellent high temperature resistance and shearing resistance, but the thickener has excessive polymer monomers and complex reaction system and does not show better recovery ratio to low permeability oil reservoirs.
Disclosure of Invention
The invention solves the technical problems that: the preparation of the hydrophobically associating polyacrylamide thickener for fracturing fluid solves the problems of poor temperature resistance and shearing resistance of the polyacrylamide thickener and low dialysis recovery ratio of crude oil.
The technical scheme of the invention is as follows: an emulsion type hydrophobically associating polyacrylamide thickener comprises the following raw materials in parts by weight: 100 parts of acrylamide, 0.5-4 parts of acrylamide carboxylic acid group cardanol monomer, 1.2-1.8 parts of emulsifier and 0.4-0.6 part of initiator;
the chemical structural formula of the acrylamide carboxylic acid group cardanol monomer is as follows:
。
further, the emulsifier comprises sodium dodecyl sulfate, sodium dodecyl benzene sulfonate and OP-10.
Further, the initiator comprises potassium persulfate, ammonium persulfate, azobisisobutyronitrile, azobisisobutyrimidine hydrochloride.
Further, the preparation process of the emulsion type hydrophobically associating polyacrylamide thickener comprises the following steps:
step (1): adding acetonitrile, potassium carbonate, an acrylamide chloropropionic acid intermediate and a cashew nut ether acetamide intermediate into a flask, stirring for reaction, adding water and ethyl acetate, oscillating for extraction, separating an organic phase, and concentrating a solvent to obtain the acrylamide carboxylic acid cardanol monomer.
Step (2): adding water, acrylamide, an acrylamide carboxylic acid group cardanol monomer and an emulsifier into a flask, introducing nitrogen, dropwise adding an initiator, stirring for reaction, cooling, adding ethanol until precipitation is separated out, filtering, washing with ethanol, and drying to obtain the emulsion type hydrophobic association polyacrylamide thickener.
Further, the proportion of acetonitrile, potassium carbonate, acrylamide chloropropionic acid intermediate and cashew nut ether acetamide intermediate in the step (1) is (10-30) mL (0.9-1.3) g (0.46-0.62) g/1 g.
Further, the temperature of the reaction in the reaction step (1) is controlled between 65 and 85 ℃ and the time is controlled between 12 and 18 hours.
Further, the temperature of the reaction in the reaction step (2) is controlled between 55 and 70 ℃ and the time is controlled between 3 and 6 hours.
Further, the preparation process of the cashew ether acetamide intermediate comprises the following steps:
step S1: toluene, chloroacetic acid and cetyltrimethylammonium bromide are added into a flask, and the mixture is stirred and dissolved to obtain an oil phase; adding sodium hydroxide and cardanol into water, wherein the proportion of toluene, chloroacetic acid, cetyltrimethylammonium bromide, water, sodium hydroxide and cardanol is (12-20) mL (0.82-0.96) g (0.044-0.056) g (10-16) mL (0.12-0.15) g:1g, stirring uniformly, heating to 75-90 ℃, adding an oil phase, reacting for 4-7h, concentrating under reduced pressure to remove toluene, adding hydrochloric acid solution to adjust pH to 4-5, adding ethyl acetate, oscillating for extraction, separating an organic phase, concentrating a solvent, and obtaining the cashew ether acetic acid intermediate.
Step S2: adding triethylene tetramine, cashew ether acetic acid intermediate and potassium hydroxide with the proportion of (1.6-2.2) g to (0.01-0.013) g into a flask provided with a water separator, introducing nitrogen, heating to 165-180 ℃, reacting for 6-18h, cooling, washing with water, acetone and dichloromethane in sequence, and drying to obtain cashew ether acetamide intermediate.
Further, the preparation process of the acrylamide-based chloropropionic acid intermediate comprises the following steps: adding acetonitrile (1.1-1.4 g) and (0.7-0.85 g) in the proportion of (10-20) to a flask, reacting for 1-3 hours at 15-25 ℃ with sodium bicarbonate, 2-amino-3-chloropropionic acid and acryloyl chloride, adding water and dichloromethane, oscillating and extracting, separating an organic phase, concentrating a solvent, and obtaining the acrylamide chloropropionic acid intermediate.
The invention has the technical effects that: the method comprises the steps of carrying out etherification reaction by using chloroacetic acid and cardanol, carrying out amidation reaction with triethylene tetramine, and finally carrying out substitution reaction with an acrylamide chloropropionic acid intermediate to prepare a novel acrylamide carboxylic acid group cardanol monomer; then carrying out polymerization reaction with acrylamide to obtain the hydrophobically associating polyacrylamide thickener.
According to the invention, the cardanol hydrophobic structure and the carboxyl hydrophilic group are simultaneously introduced into the polyacrylamide molecular chain to form strong hydrophobic association and amphipathic interaction, and the alkyl long chains of the cardanol form space physical crosslinking, so that the heat resistance of the polyacrylamide is improved, the problem of high-temperature thermal degradation is solved, the polyacrylamide thickener has higher apparent viscosity and heat resistance, the thickener solution still maintains higher viscosity at high temperature, and a good thickening effect is achieved. The method can be suitable for high-temperature complex environments of low-permeability oil reservoir exploitation.
The interfacial tension of the hydrophobically associating polyacrylamide thickener solution and the crude oil simulated oil is lower, and when the interfacial tension of the thickener solution and the crude oil in the core is lower in the actual oil reservoir exploitation process, the resistance generated when crude oil drops pass through the core pore canal can be reduced, and the crude oil drops are promoted to flow out of the core pore canal, so that the dialysis recovery ratio is improved.
Detailed Description
The technical solutions of the present invention will be clearly and completely described with reference to the following examples, which are only for illustrating the present invention and should not be construed as limiting the scope of the present invention.
Example 1
10mL of toluene, 0.48g of chloroacetic acid and 28mg of cetyltrimethylammonium bromide (CTAB) were added to the flask, and the mixture was dissolved with stirring to obtain an oil phase; 75mg of sodium hydroxide and 0.5g of cardanol are added into 8mL of water, the temperature is raised to 80 ℃ after the mixture is stirred uniformly, an oil phase is added, the reaction is carried out for 4 hours, toluene is removed through reduced pressure concentration, a hydrochloric acid solution is added to adjust the pH to 4, ethyl acetate is added, the mixture is subjected to shaking extraction, an organic phase is separated, and a solvent is concentrated, so that a cashew ether acetic acid intermediate is obtained.
To a flask equipped with a water separator, 0.8g of triethylene tetramine, 0.5g of cashew ether acetic acid intermediate and 5mg of potassium hydroxide were added, nitrogen gas was introduced, the temperature was raised to 170 ℃, the reaction was carried out for 6 hours, the mixture was cooled, washed with water, acetone and methylene chloride in sequence, and the mixture was dried to obtain cashew ether acetamide intermediate. The reaction formula is as follows:
。
to the flask, acetonitrile, 0.48g of sodium bicarbonate, 0.4g of 2-amino-3-chloropropionic acid and 0.3g of acryloyl chloride were added in a ratio of 8mL, and the mixture was reacted at 15℃for 3 hours, water and methylene chloride were added, the organic phase was separated by shaking extraction, and the solvent was concentrated to obtain an acrylamide-based chloropropionic acid intermediate. The reaction formula is as follows:
。
to the flask were added 20mL of acetonitrile, 1.1g of potassium carbonate, 0.62g of acrylamido chloropropionic acid intermediate and 1g of cashew nut ether acetamide intermediate, and the mixture was stirred at 65℃for 18 hours to react, water and ethyl acetate were added, the mixture was extracted with shaking, the organic phase was separated, and the solvent was concentrated to obtain an acrylamide carboxylic acid group cardanol monomer. The reaction formula is as follows:
。
300mL of water, 50g of acrylamide, 0.25g of acrylamide carboxylic acid group cardanol monomer and 0.6g of emulsifier sodium dodecyl benzene sulfonate are added into a flask, nitrogen is introduced, 0.2g of initiator ammonium persulfate is dropwise added, stirring reaction is carried out for 3 hours at 70 ℃, ethanol is added after cooling until precipitation is achieved, filtering, ethanol washing and drying are carried out, and then the emulsion type hydrophobically associating polyacrylamide thickener is obtained.
Example 2
(6 mL of toluene, 0.41g of chloroacetic acid and 22mg of cetyltrimethylammonium bromide are added into a flask, stirring and dissolving are carried out to obtain an oil phase, 60mg of sodium hydroxide and 0.5g of cardanol are added into 5mL of water, stirring is carried out evenly, then the temperature is raised to 75 ℃, the oil phase is added, reaction is carried out for 7 hours, reduced pressure concentration is carried out to remove toluene, hydrochloric acid solution is added to adjust the pH to 5, ethyl acetate is added, vibration extraction is carried out, an organic phase is separated, and a solvent is concentrated to obtain cashew ether acetic acid intermediate.
To a flask equipped with a water separator, 0.9g of triethylene tetramine, 0.5g of cashew ether acetic acid intermediate and 5mg of potassium hydroxide were added, nitrogen gas was introduced, the temperature was raised to 180 ℃, the reaction was carried out for 12 hours, the mixture was cooled, washed with water, acetone and methylene chloride in sequence, and the mixture was dried to obtain cashew ether acetamide intermediate.
To the flask, acetonitrile, 0.44g of sodium bicarbonate, 0.4g of 2-amino-3-chloropropionic acid and 0.28g of acryloyl chloride were added in a ratio, and the mixture was reacted at 20℃for 2 hours, water and methylene chloride were added, the organic phase was separated by shaking extraction, and the solvent was concentrated to obtain an acrylamide-based chloropropionic acid intermediate.
To the flask, 10mL of acetonitrile, 0.9g of potassium carbonate, 0.55g of acrylamide-based chloropropionic acid intermediate and 1g of cashew nut ether acetamide intermediate were added, and the mixture was stirred at 85℃for reaction for 15 hours, water and ethyl acetate were added, the mixture was subjected to shaking extraction, and the organic phase was separated, and the solvent was concentrated to obtain an acrylamide-based carboxylic acid cardanol monomer.
350mL of water, 50g of acrylamide, 0.8g of acrylamide carboxylic acid group cardanol monomer and 0.7g of emulsifier OP-10 are added into a flask, nitrogen is introduced, 0.23g of initiator azodiisobutyronitrile is added dropwise, stirring reaction is carried out for 3 hours at 70 ℃, ethanol is added after cooling until precipitation is separated out, filtering, ethanol washing and drying are carried out, and then the emulsion type hydrophobic association polyacrylamide thickener is obtained.
Example 3
10mL of toluene, 0.48g of chloroacetic acid and 25mg of cetyltrimethylammonium bromide were added to the flask, and the mixture was stirred and dissolved to obtain an oil phase; to 8mL of water, 65mg of sodium hydroxide and 0.5g of cardanol are added, after stirring uniformly, the temperature is raised to 90 ℃, the oil phase is added, the reaction is carried out for 4 hours, toluene is removed by decompression and concentration, hydrochloric acid solution is added to adjust the pH to 4, ethyl acetate is added, the shaking extraction is carried out, the organic phase is separated, and the solvent is concentrated, thus obtaining cashew ether acetic acid intermediate.
To a flask equipped with a water separator, 1.1g of triethylene tetramine, 0.5g of cashew ether acetic acid intermediate and 6.5mg of potassium hydroxide were added, nitrogen gas was introduced, the temperature was raised to 165 ℃, the reaction was carried out for 18 hours, the mixture was cooled, washed with water, acetone and methylene chloride in sequence, and dried, thereby obtaining cashew ether acetamide intermediate.
To the flask, acetonitrile, 0.56g of sodium bicarbonate, 0.4g of 2-amino-3-chloropropionic acid and 0.34g of acryloyl chloride were added in a ratio of 8mL, and the mixture was reacted at 25℃for 1 hour, water and methylene chloride were added, the organic phase was separated by shaking extraction, and the solvent was concentrated to obtain an acrylamide-based chloropropionic acid intermediate.
To the flask, 30mL of acetonitrile, 1.3g of potassium carbonate, 0.62g of acrylamide-based chloropropionic acid intermediate and 1g of cashew nut ether acetamide intermediate were added, and the mixture was stirred at 80℃for reaction for 12 hours, water and ethyl acetate were added, the mixture was subjected to shaking extraction, and the organic phase was separated, and the solvent was concentrated to obtain an acrylamide-based carboxylic acid cardanol monomer.
350mL of water, 50g of acrylamide, 1.4g of acrylamide carboxylic acid group cardanol monomer, 0.8g of emulsifier sodium dodecyl sulfate, nitrogen gas and 0.27g of initiator potassium persulfate are added into a flask, stirring is carried out at 55 ℃ for 6 hours, ethanol is added after cooling until precipitation is achieved, filtering, ethanol washing and drying are carried out, and then the emulsion type hydrophobic association polyacrylamide thickener is obtained.
Example 4
6mL of toluene, 0.41g of chloroacetic acid and 25mg of cetyltrimethylammonium bromide were added to the flask, and the mixture was stirred and dissolved to obtain an oil phase; 60mg of sodium hydroxide and 0.5g of cardanol are added into 5mL of water, the temperature is raised to 80 ℃ after the mixture is stirred uniformly, an oil phase is added, the reaction is carried out for 4 hours, toluene is removed through reduced pressure concentration, a hydrochloric acid solution is added to adjust the pH to 4, ethyl acetate is added, the mixture is subjected to shaking extraction, an organic phase is separated, and a solvent is concentrated, so that a cashew ether acetic acid intermediate is obtained.
To a flask equipped with a water separator, 1.1g of triethylene tetramine, 0.5g of cashew ether acetic acid intermediate and 5.5mg of potassium hydroxide were added, nitrogen gas was introduced, the temperature was raised to 170 ℃, the reaction was carried out for 18 hours, the mixture was cooled, washed with water, acetone and methylene chloride in sequence, and dried, thereby obtaining cashew ether acetamide intermediate.
To the flask, acetonitrile, 0.44g of sodium bicarbonate, 0.4g of 2-amino-3-chloropropionic acid and 0.3g of acryloyl chloride were added in a ratio, and the mixture was reacted at 15℃for 2 hours, water and methylene chloride were added, the organic phase was separated by shaking extraction, and the solvent was concentrated to obtain an acrylamide-based chloropropionic acid intermediate.
To the flask, 10mL of acetonitrile, 0.9g of potassium carbonate, 0.46g of acrylamide-based chloropropionic acid intermediate and 1g of cashew nut ether acetamide intermediate were added, and the mixture was stirred at 65℃for 18 hours to react, water and ethyl acetate were added, the mixture was extracted by shaking, the organic phase was separated, and the solvent was concentrated to obtain an acrylamide-based carboxylic acid cardanol monomer.
400mL of water, 50g of acrylamide, 2g of acrylamide carboxylic acid group cardanol monomer and 0.9g of emulsifier OP-10 are added into a flask, nitrogen is introduced, 0.3g of initiator azo diisobutyl hydrochloride is added dropwise, stirring reaction is carried out for 3 hours at 70 ℃, ethanol is added after cooling until precipitation is carried out, filtering, ethanol washing and drying are carried out, and thus the emulsion type hydrophobic association polyacrylamide thickener is obtained.
Comparative example 1
300mL of water, 50g of acrylamide and 0.6g of emulsifier sodium dodecyl benzene sulfonate are added into a flask, nitrogen is introduced, 0.2g of initiator ammonium persulfate is added dropwise, stirring is carried out at 70 ℃ for 3 hours, ethanol is added until precipitation is achieved after cooling, and then the polyacrylamide thickener is obtained through filtering, ethanol washing and drying.
Comparative example 2
Preparation of acrylamide-based chloropropionic acid intermediate) The preparation process was the same as in example 1.
300mL of water, 50g of acrylamide, 0.25g of acrylamide-based chloropropionic acid intermediate and 0.6g of emulsifier sodium dodecyl benzene sulfonate are added into a flask, nitrogen is introduced, 0.2g of initiator ammonium persulfate is dropwise added, stirring reaction is carried out for 3 hours at 70 ℃, ethanol is added after cooling until precipitation is separated out, filtering, ethanol washing and drying are carried out, and the polyacrylamide thickener is obtained.
Comparative example 3
Preparation of cashew ether acetamide intermediate) The preparation process was the same as in example 1.
To the flask, acetonitrile, 0.16g of sodium bicarbonate, 0.5g of cashew ether acetamide intermediate and 0.11g of acryloyl chloride were added in a ratio of 6mL, and the mixture was reacted at 15℃for 3 hours, water and ethyl acetate were added, the mixture was subjected to shaking extraction, and the organic phase was separated, and the solvent was concentrated to obtain an acrylamide cardanol monomer. The reaction formula is as follows:
。
300mL of water, 50g of acrylamide, 0.25g of acrylamide cardanol monomer and 0.6g of emulsifier sodium dodecyl benzene sulfonate are added into a flask, nitrogen is introduced, 0.2g of initiator ammonium persulfate is added dropwise, stirring is carried out at 70 ℃ for 3 hours, ethanol is added after cooling until precipitation is achieved, filtering, ethanol washing and drying are carried out, and the polyacrylamide thickener is obtained.
Adding polyacrylamide thickener into water, stirring uniformly to prepare solution with concentration of 3g/L, and measuring apparent viscosity of the solution at different temperatures by adopting a rotational viscometer.
TABLE 1 apparent viscosity test of Polyacrylamide thickeners
Adding the polyacrylamide thickener into water, uniformly stirring to prepare a solution with the concentration of 3g/L, and then adding the solution into a rotary viscosimeter to measure the apparent viscosity of the solution.
In the embodiments 1 to 4, acrylamide cardanol monomers are used as functional monomers to be copolymerized with acrylamide, a cardanol hydrophobic structure and a carboxyl hydrophilic group are simultaneously introduced into a polyacrylamide molecular chain to form strong hydrophobic association and amphiphilic interaction, and space physical crosslinking is formed between alkyl long chains of cardanol, so that the heat resistance of the polyacrylamide is improved, the problem of high-temperature thermal degradation is favorably overcome, and the polyacrylamide thickener has higher apparent viscosity and heat resistance, and the thickener solution still maintains higher viscosity at a high temperature.
Comparative example 1 is a common polyacrylamide, which has low apparent viscosity, poor temperature resistance and rapid decrease in apparent viscosity at high temperature.
Comparative example 2 an acrylamido chloropropionic acid intermediate was copolymerized with acrylamide; comparative example 3 acrylamide cardanol monomer was copolymerized with acrylamide; the obtained polyacrylamide thickener does not form an amphiphilic interaction of a good hydrophobic structure of cardanol-hydrophobic association of carboxyl hydrophilic groups, and the apparent viscosity and the temperature resistance of the polyacrylamide thickener are poor.
High-speed shearing is carried out on the polyacrylamide thickener solution with the concentration of 3g/L, the shearing rate is controlled to be 400r/min, the temperature is 25 ℃, and the apparent viscosity of the solution is tested under different shearing time.
TABLE 2 apparent viscosity of Polyacrylamide thickeners
In the embodiments 1 to 4, acrylamide cardanol monomers are used as functional monomers to be copolymerized with acrylamide, and the prepared polyacrylamide thickener forms hydrophobic association and amphipathic interaction of cardanol hydrophobic structures and carboxyl hydrophilic groups, so that the acrylamide thickener has a higher shearing resistance effect and still has higher apparent viscosity after long-time high-speed shearing.
And taking the crude oil extracted from the low-permeability reservoir as experimental simulated oil, and measuring the interfacial tension between the polyacrylamide thickener solution with the concentration of 3g/L and the experimental simulated oil by adopting an interfacial tensiometer. The smaller the oil-water interfacial tension value is, the better the recovery ratio is.
And taking polyacrylamide thickener solution with the concentration of 3g/L as seepage liquid, and taking low-permeability reservoir crude oil as experimental simulated oil to carry out seepage experiments. Vacuum drying the natural outcrop core, carrying out saturated stratum water, and then carrying out saturated simulated oil at 45 ℃; and adding the imbibition liquid into an imbibition bottle, then adding a core to carry out imbibition process, and measuring imbibition recovery ratio.
TABLE 3 interfacial tension and imbibition recovery of polyacrylamide thickeners
Examples 1 to 4 the interface tension between the hydrophobically associating polyacrylamide thickener solution prepared and the simulated oil was only 0.0091-0.0198 mN. Mu.m -1 The highest absorption recovery rate reaches 26.9%.
Claims (10)
1. The emulsion type hydrophobically associating polyacrylamide thickener is characterized by comprising the following raw materials in parts by weight: 100 parts of acrylamide, 0.5-4 parts of acrylamide carboxylic acid group cardanol monomer, 1.2-1.8 parts of emulsifier and 0.4-0.6 part of initiator;
the chemical structural formula of the acrylamide carboxylic acid group cardanol monomer is shown as formula (I):
（Ⅰ）。
2. the emulsion type hydrophobically associating polyacrylamide thickener according to claim 1, wherein the emulsifier comprises sodium dodecyl sulfate, sodium dodecyl benzene sulfonate, OP-10.
3. The emulsion hydrophobically associating polyacrylamide thickener of claim 1, wherein the initiator comprises potassium persulfate, ammonium persulfate, azobisisobutyronitrile, amidine hydrochloride.
4. A process for preparing the emulsion type hydrophobically associating polyacrylamide thickener as claimed in any one of claims 1 to 3, comprising the steps of:
step (1): adding acetonitrile, potassium carbonate, an acrylamide chloropropionic acid intermediate and a cashew nut ether acetamide intermediate into a flask, stirring for reaction, extracting, separating an organic phase, and concentrating a solvent to obtain an acrylamide carboxylic acid group cardanol monomer;
step (2): adding water, acrylamide, an acrylamide carboxylic acid group cardanol monomer and an emulsifier into a flask, introducing nitrogen, dropwise adding an initiator, stirring for reaction, cooling, adding ethanol until precipitation is separated out, filtering, washing and drying to obtain the emulsion type hydrophobic association polyacrylamide thickener.
5. The process for preparing the emulsion type hydrophobically associating polyacrylamide thickener according to claim 4, wherein the proportion of acetonitrile, potassium carbonate, acrylamide chloropropionic acid intermediate and cashew ether acetamide intermediate in the step (1) is (10-30) mL (0.9-1.3) g (0.46-0.62) g:1g.
6. The process for preparing the emulsion type hydrophobically associating polyacrylamide thickener according to claim 4, wherein the reaction temperature in the step (1) is controlled between 65 ℃ and 85 ℃ and the reaction time is controlled between 12h and 18 h.
7. The process for preparing the emulsion type hydrophobically associating polyacrylamide thickener according to claim 4, wherein the reaction temperature in the step (2) is controlled between 55 ℃ and 70 ℃ and the reaction time is controlled between 3h and 6 h.
8. The preparation process of the emulsion type hydrophobically associating polyacrylamide thickener according to claim 4, wherein the preparation process of the cashew nut ether acetamide intermediate comprises the following steps:
step S1: toluene, chloroacetic acid and cetyltrimethylammonium bromide are added into a flask, and the mixture is stirred and dissolved to obtain an oil phase; adding sodium hydroxide and cardanol into water, stirring uniformly, heating to 75-90 ℃, adding an oil phase, reacting for 4-7h, concentrating under reduced pressure to remove toluene, adding hydrochloric acid solution to adjust pH to 4-5, extracting, separating an organic phase, and concentrating a solvent to obtain a cashew ether acetic acid intermediate;
step S2: adding triethylene tetramine, cashew ether acetic acid intermediate and potassium hydroxide with the proportion of (1.6-2.2) g to (1.01-0.013) g into a flask provided with a water separator, introducing nitrogen, heating to 165-180 ℃, reacting for 6-18h, cooling, washing and drying to obtain the cashew ether acetamide intermediate.
9. The process for preparing the emulsion type hydrophobically associating polyacrylamide thickener according to claim 8, wherein the proportion of toluene, chloroacetic acid, cetyltrimethylammonium bromide, water, sodium hydroxide and cardanol in the step S1 is (12-20) mL (0.82-0.96) g (0.044-0.056) g (10-16) mL (0.12-0.15) g 1g.
10. The preparation process of the emulsion type hydrophobically associating polyacrylamide thickener according to claim 4, wherein the preparation process of the acrylamide chloropropionic acid intermediate comprises the following steps: adding acetonitrile (1.1-1.4 g) and (0.7-0.85 g) in the proportion of (1-20) mL into a flask, reacting for 1-3h at 15-25 ℃ with sodium bicarbonate, 2-amino-3-chloropropionic acid and acryloyl chloride, extracting, separating an organic phase, and concentrating a solvent to obtain an acrylamide chloropropionic acid intermediate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311757812.6A CN117430748B (en) | 2023-12-20 | 2023-12-20 | Emulsion type hydrophobically associating polyacrylamide thickener and preparation process thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311757812.6A CN117430748B (en) | 2023-12-20 | 2023-12-20 | Emulsion type hydrophobically associating polyacrylamide thickener and preparation process thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN117430748A true CN117430748A (en) | 2024-01-23 |
| CN117430748B CN117430748B (en) | 2024-03-08 |
Family
ID=89546468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311757812.6A Active CN117430748B (en) | 2023-12-20 | 2023-12-20 | Emulsion type hydrophobically associating polyacrylamide thickener and preparation process thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117430748B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117736370A (en) * | 2024-02-18 | 2024-03-22 | 东营江源化工有限公司 | Thickening tackifier for temperature-resistant polyacrylamide fracturing fluid and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105254792A (en) * | 2015-10-19 | 2016-01-20 | 刘剑锋 | Modified cardanol derivative water reducer and preparation method thereof |
| CN105367710A (en) * | 2015-12-26 | 2016-03-02 | 宋介珍 | Preparation method for modified polyacrylamide filtrate reducer for drilling fluid |
| US20180282480A1 (en) * | 2015-10-09 | 2018-10-04 | Clariant International Ltd. | Cashew Nutshell Liquid Alkoxylate Carboxylate as a New Renewable Surfactant Composition for Enhanced Oil Recovery Applications |
| CN109097005A (en) * | 2018-08-09 | 2018-12-28 | 李志平 | A kind of oil-based drilling fluid emulsifying agent |
-
2023
- 2023-12-20 CN CN202311757812.6A patent/CN117430748B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180282480A1 (en) * | 2015-10-09 | 2018-10-04 | Clariant International Ltd. | Cashew Nutshell Liquid Alkoxylate Carboxylate as a New Renewable Surfactant Composition for Enhanced Oil Recovery Applications |
| CN105254792A (en) * | 2015-10-19 | 2016-01-20 | 刘剑锋 | Modified cardanol derivative water reducer and preparation method thereof |
| CN105367710A (en) * | 2015-12-26 | 2016-03-02 | 宋介珍 | Preparation method for modified polyacrylamide filtrate reducer for drilling fluid |
| CN109097005A (en) * | 2018-08-09 | 2018-12-28 | 李志平 | A kind of oil-based drilling fluid emulsifying agent |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117736370A (en) * | 2024-02-18 | 2024-03-22 | 东营江源化工有限公司 | Thickening tackifier for temperature-resistant polyacrylamide fracturing fluid and preparation method thereof |
| CN117736370B (en) * | 2024-02-18 | 2024-05-03 | 东营江源化工有限公司 | Thickening tackifier for temperature-resistant polyacrylamide fracturing fluid and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN117430748B (en) | 2024-03-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN117430748B (en) | Emulsion type hydrophobically associating polyacrylamide thickener and preparation process thereof | |
| CN103275270A (en) | Method for preparing fluorocarbon-modified polyacrylamide by using soap-free emulsion method | |
| CN103555311A (en) | AM/NaAA/APO (acrylamide/sodium acrylate/N-allylphenoxyacetamide) ternary polymer flooding agent and synthesis method | |
| CN110982009B (en) | Fluoropolymer microemulsion wetting reversal agent and preparation method and application thereof | |
| CN104817663A (en) | Preparation method of polycarboxylate water-reducer capable of inhibiting side-effect of montmorillonite and polymeric monomer | |
| CN114989348B (en) | High-temperature-resistant salt-resistant organosilicon fluid loss additive and preparation method and application thereof | |
| CN115572347A (en) | High-temperature-resistant high-salt-resistant tackifying and shearing-improving agent for water-based drilling fluid and preparation method and application thereof | |
| CN117736370B (en) | Thickening tackifier for temperature-resistant polyacrylamide fracturing fluid and preparation method thereof | |
| CN105646772A (en) | Hydrophobic associated polymer and preparation method thereof | |
| CN111187373B (en) | Epoxy vegetable oil nucleic acid base copolymer, preparation method thereof and application of composite material | |
| CN117510716B (en) | Preparation method of drag-reduction thickening fracturing auxiliary agent | |
| KR20050056288A (en) | Acrylamides monomer and thermoresponsive acrylamides polymer prepared by using same | |
| CN103214390B (en) | N-ethyl methylpropenyl dehydroabietic amide and synthesis method thereof | |
| CN113929829B (en) | Preparation method of surface active polyacrylamide microspheres | |
| CN106883362B (en) | Copolymer, intermediate and preparation method thereof, purposes | |
| CN114763394B (en) | Nonionic hyperbranched hydrophobically associating polyacrylamide thickener and preparation method thereof | |
| CN113731297A (en) | Amido sulfonate gemini surfactant as well as preparation method and application thereof | |
| CN112341567A (en) | Thickener for supercritical carbon dioxide flooding and preparation method and application thereof | |
| CN107365402B (en) | Preparation method of micro-branched micro-crosslinked polyacrylamide | |
| CN103508914B (en) | Hydrophobic polymerizable monomer and oil-displacing agent composition as well as preparation method thereof | |
| CN108424490B (en) | Acrylamide copolymer and preparation method and application thereof | |
| CN109749006B (en) | Polymer with surface activity function and preparation method and application thereof | |
| CN103508913B (en) | Monomer, ternary random copolymer, preparation methods of monomer and ternary random copolymer, and application of ternary random copolymer | |
| CN114075126B (en) | Compound and preparation method thereof, polymer and preparation method and application thereof | |
| CN114075310B (en) | Two-phase viscosity regulator and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |