CN116948615A - Epoxy resin plugging material for improving stratum bearing capacity and oil-based drilling fluid - Google Patents
Epoxy resin plugging material for improving stratum bearing capacity and oil-based drilling fluid Download PDFInfo
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- CN116948615A CN116948615A CN202310928395.0A CN202310928395A CN116948615A CN 116948615 A CN116948615 A CN 116948615A CN 202310928395 A CN202310928395 A CN 202310928395A CN 116948615 A CN116948615 A CN 116948615A
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- Prior art keywords
- epoxy resin
- plugging material
- drilling fluid
- oil
- bearing capacity
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 75
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 75
- 239000000463 material Substances 0.000 title claims abstract description 61
- 238000005553 drilling Methods 0.000 title claims abstract description 33
- 239000012530 fluid Substances 0.000 title claims abstract description 26
- 239000000126 substance Substances 0.000 claims abstract description 59
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229910010271 silicon carbide Inorganic materials 0.000 claims abstract description 35
- 229920006389 polyphenyl polymer Polymers 0.000 claims abstract description 29
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 26
- 239000003921 oil Substances 0.000 claims abstract description 23
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 13
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 57
- 238000003756 stirring Methods 0.000 claims description 35
- 238000010438 heat treatment Methods 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 238000001035 drying Methods 0.000 claims description 20
- 125000003700 epoxy group Chemical group 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 238000001291 vacuum drying Methods 0.000 claims description 14
- 238000005406 washing Methods 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 10
- 239000003995 emulsifying agent Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- -1 3-amino-4- (2-phenylbenzopyran-6-yloxy) anisole Chemical compound 0.000 claims description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 238000001132 ultrasonic dispersion Methods 0.000 claims description 7
- 238000005303 weighing Methods 0.000 claims description 7
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000004289 sodium hydrogen sulphite Substances 0.000 claims description 6
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 6
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 5
- 239000000080 wetting agent Substances 0.000 claims description 5
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 4
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 claims description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical group [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 4
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000292 calcium oxide Substances 0.000 claims description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 4
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims description 3
- KNYWJNQPNWFFHH-UHFFFAOYSA-N 2-naphthalen-2-yloxyaniline Chemical compound NC1=CC=CC=C1OC1=CC=C(C=CC=C2)C2=C1 KNYWJNQPNWFFHH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002199 base oil Substances 0.000 claims description 3
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000002002 slurry Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 238000012669 compression test Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5033—Amines aromatic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/02—Well-drilling compositions
- C09K8/03—Specific additives for general use in well-drilling compositions
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/02—Well-drilling compositions
- C09K8/32—Non-aqueous well-drilling compositions, e.g. oil-based
- C09K8/36—Water-in-oil emulsions
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/42—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells
- C09K8/426—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells for plugging
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/42—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells
- C09K8/44—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells containing organic binders only
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epoxy Resins (AREA)
Abstract
The invention discloses an epoxy resin plugging material for improving stratum bearing capacity and an oil-based drilling fluid, and belongs to the technical field of oil-gas field drilling. The plugging agent used for the oil-based drilling fluid is an epoxy resin plugging material for improving the bearing capacity of the stratum, the epoxy resin plugging material is prepared by a stepwise method, and the synthetic raw materials comprise aniline substances containing ether bonds, epichlorohydrin, dihydroxy substituted polyphenyl substances, silicon carbide and silane coupling agents. The molar ratio of the aniline substance containing ether bond, the dihydroxy-substituted polyphenyl substance and the epichlorohydrin is about 1:0.5:2. the addition amount of the rigid material silicon carbide is between 10 and 30 g. The compressive strength of the epoxy resin plugging material can reach 130-170MPa, and the epoxy resin plugging material can be used as a pressure-bearing plugging material in oil-based drilling fluid, so that the leakage of the drilling fluid is reduced, and the formation stability is improved.
Description
Technical Field
The invention relates to the technical field of drilling of oil and gas fields, in particular to an epoxy resin plugging material for improving stratum bearing capacity and an oil-based drilling fluid.
Background
Drilling fluid leakage is a problem of constant concern in the petroleum engineering industry, which can lead to underground complex conditions and malignant accidents, and can bring great harm to drilling engineering, oil and gas field development and reservoir protection. In the drilling process, after drilling fluid enters the stratum from the well hole through the leakage channel, constructors need to consume a large amount of slurry and plugging materials to solve the problem of lost circulation. If the treatment is proper, the leakage stoppage consumption can be greatly reduced; however, if the treatment is improper, unpredictable losses of manpower, financial resources, time and the like can be caused, even underground accidents such as well collapse, drilling sticking, blowout and the like can occur, and serious problems such as well scrapping and permanent reservoir damage can be caused.
The handling of lost circulation problems has been an important issue in the drilling field. Although a large amount of conventional plugging agents are applied at present, a certain application effect is achieved, and an ideal plugging effect is often difficult to achieve due to insufficient bearing capacity. Accordingly, there is a need for further development and improvement of lost circulation materials with pressure bearing capabilities to better address lost circulation conditions and to improve the safety and efficiency of drilling operations.
The Chinese patent with publication number of CN 115772392A proposes a polymer oil-based crosslinking curing plugging agent for drilling fluid and a preparation method thereof, wherein the plugging agent is prepared by mixing modified first epoxy resin and second epoxy resin to obtain modified epoxy resin, the plugging agent comprises 60-80% of modified epoxy resin, 15-30% of curing agent, 1-5% of curing regulator, 4-10% of reinforcing agent and compressive strength of the plugging agent of more than 30MPa, thereby solving the problems of poor anti-pollution capability and poor plugging effect. However, there is room for improvement in compressive strength.
The epoxy resin contains benzene ring, ether bond, hydroxyl, epoxy group and other groups in the molecule, and the groups endow the epoxy resin with excellent performance. Among them, the benzene ring can improve the mechanical strength and heat resistance of the epoxy resin, and the ether bond imparts excellent chemical resistance to the epoxy resin, which makes the epoxy resin an ideal plugging material. However, most of epoxy resins are prepared from bisphenol A, and the chain-type epoxy resins have poor mechanical properties and cannot be effectively used for plugging. Branched epoxy resins exhibit a great improvement in mechanical properties, in particular in pressure-bearing capacity, compared to linear epoxy resins. Therefore, the branched epoxy resin is a better plugging material. The rigid material silicon carbide is added into the material, so that the compressive capacity of the material can be greatly improved.
Disclosure of Invention
Aiming at the problem that most of the existing plugging materials still have poor plugging effect due to insufficient bearing capacity, the invention provides the epoxy resin plugging material for improving the bearing capacity of the stratum and the oil-based drilling fluid.
In order to achieve the above purpose, the technical scheme of the invention is as follows: an epoxy resin plugging material for improving the bearing capacity of stratum. The raw materials of the epoxy resin plugging material comprise aniline substances containing ether bonds, epichlorohydrin, dihydroxy substituted polyphenyl substances, silicon carbide and silane coupling agents, and the epoxy resin plugging material is prepared by the following steps:
s1, adding aniline substances containing ether bonds and a methanol solution into a three-necked flask, preparing a reflux condensing device, dropwise adding epoxy chloropropane in a stirring state, heating to 65-75 ℃ for reaction for 4-6 hours, adding triethylamine, cooling to 40-60 ℃, stirring for 3-5 hours, and purifying to obtain benzene substances containing epoxy groups;
s2, adding a mixture of dihydroxy-substituted polyphenyl substances and sodium bisulphite dispersed in an ammonia water solution with the mass fraction of 25% into a three-necked flask, heating to 150-180 ℃, reacting for 12-15h under a stirring state, cooling the reaction mixture to room temperature, adding an NaOH aqueous solution to regulate the pH value to be more than 12, drying, and washing to obtain the polyamino-substituted polyphenyl substances;
s3, placing the silicon carbide in a vacuum drying oven at 80-110 ℃ for drying for 6-8 hours, accurately weighing the dried silicon carbide in a three-necked flask, adding toluene and a silane coupling agent into the three-necked flask, introducing nitrogen, heating to 80-90 ℃ for stirring reaction for 5-8 hours, performing ultrasonic dispersion, centrifuging at a high speed of 10000r/min for 30 minutes, washing with acetone, and placing in a vacuum drying oven at 100-120 ℃ for drying for 10-12 hours to obtain the silane coupling agent modified silicon carbide;
s4, mixing the benzene substances containing epoxy groups prepared in the S1 and the polyamino substituted polyphenyl substances prepared in the S2, heating to 130-160 ℃ for reaction for 4-7 hours to obtain a branched epoxy resin polymer, and mixing the branched epoxy resin polymer and the silicon carbide modified by the silane coupling agent prepared in the S3 to obtain the epoxy resin plugging material for improving the bearing capacity of the stratum.
The aniline substance containing ether bond in the step S1 is one of 3-amino-4- (2-phenylbenzopyran-6-yloxy) anisole and 2- (2-naphthoyloxy) aniline.
The dihydroxyl substituted polyphenyl substance in the step S2 is one of 5, 8-dihydroxyl-10-methoxyl-2-methyl-4H-naphthalene [1,2-b ] pyran-4-ketone, 5, 8-dihydroxyl-6, 10-dimethoxy-2-methyl-4H-naphthalene [1,2-b ] pyran-4-ketone, 6-diphenyl-2, 7-naphthalene diol and 1,1' - (2, 7-dihydroxyl-1, 6-naphthalenediyl) diethyl ketone.
The silane coupling agent in the step S3 is one of 3-aminopropyl triethoxysilane and 3-aminopropyl trimethoxysilane.
The molar ratio of the aniline substance containing ether bond, the dihydroxy substituted polyphenyl substance and the epoxy chloropropane is about 1:0.5:2.
the addition amount of the rigid material silicon carbide is between 5 and 30 g.
In the invention, the monomer material for synthesizing the epoxy resin has a multi-benzene ring structure, can improve the compression resistance and the temperature resistance of the epoxy resin, and has branched chain type rather than straight chain type molecules when the polymerization reaction occurs; contains a large number of benzene ring structures and is compounded with rigid materials, and the formed materials have good bearing capacity. The polymer can be used as a pressure-bearing plugging material for oil-based drilling fluid, so that the leakage of the drilling fluid is reduced, and the formation stability is improved.
Drawings
FIG. 1 is a schematic partial structural view of a branched epoxy resin polymer in example IV.
Detailed Description
The technical solutions of the present invention will be clearly and completely described in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
In this example, the parts are parts by weight unless otherwise specified.
1. Preparation of epoxy resin plugging material for improving stratum bearing capacity:
example 1
(1) Synthesis of benzene substance containing epoxy group
0.1mol of 3-amino-4- (2-phenylbenzopyran-6-yloxy) anisole and 100mL of methanol solution are added into a three-necked flask, a reflux condenser is arranged, after 0.2mol of epichlorohydrin is added dropwise under stirring, the temperature is raised to 65 ℃ for reaction for 6 hours, 30mL of triethylamine is added, the temperature is reduced to 40 ℃ and stirring is carried out for 5 hours, and the benzene substance containing epoxy groups is obtained after purification.
(2) Synthesis of polyamino substituted polyphenyl substances
Adding a mixture of 0.1mol of 5, 8-dihydroxyl-10-methoxy-2-methyl-4H-naphthalene [1,2-b ] pyran-4-one and 0.25mol of sodium bisulphite dispersed in 80mL of aqueous ammonia solution with mass fraction of 25% into a three-necked flask, heating to 150 ℃, reacting for 12H under stirring, cooling the reaction mixture to room temperature, adding an aqueous NaOH solution to regulate the pH value to be more than 12, drying and washing to obtain the polyamino substituted polyphenyl substance.
(3) Silane coupling agent modified silicon carbide
And (3) placing the silicon carbide in a vacuum drying oven at 80 ℃ for drying for 8 hours, accurately weighing 10g of dried silicon carbide in a three-necked flask, adding 70mL of toluene and 0.3g of 3-aminopropyl triethoxysilane into the three-necked flask, introducing nitrogen, heating to 80 ℃ for stirring reaction for 7 hours, performing ultrasonic dispersion, centrifuging at a high speed of 10000r/min for 30 minutes, washing with acetone, and placing in a vacuum drying oven at 100 ℃ for drying for 11 hours to obtain the silicon carbide modified by the silane coupling agent.
(4) Preparation of epoxy resin plugging material for improving stratum bearing capacity
Mixing the benzene substances containing epoxy groups prepared in the step (1) and the polyamino substituted polyphenyl substances prepared in the step (2), heating to 140 ℃ for reaction for 5 hours to obtain a branched epoxy resin polymer, and then mixing the branched epoxy resin polymer and the silicon carbide modified by the silane coupling agent prepared in the step (3) to obtain the epoxy resin plugging material for improving the stratum bearing capacity.
Example 2
(1) Synthesis of benzene substance containing epoxy group
0.1mol of 3-amino-4- (2-phenylbenzopyran-6-yloxy) anisole and 100mL of methanol solution are added into a three-necked flask, a reflux condenser is arranged, after 0.2mol of epichlorohydrin is added dropwise under stirring, the temperature is raised to 70 ℃ for reaction for 5 hours, 30mL of triethylamine is added, the temperature is reduced to 50 ℃ for stirring for 4 hours, and the benzene substance containing epoxy groups is obtained after purification.
(2) Synthesis of polyamino substituted polyphenyl substances
Adding a mixture of 0.1mol of 5, 8-dihydroxyl-6, 10-dimethoxy-2-methyl-4H-naphthalene [1,2-b ] pyran-4-one and 0.25mol of sodium bisulphite dispersed in 80mL of an ammonia water solution with the mass fraction of 25% into a three-necked flask, heating to 160 ℃, reacting for 12 hours under a stirring state, cooling the reaction mixture to room temperature, adding an NaOH aqueous solution to regulate the pH value to be more than 12, drying and washing to obtain the polyamino substituted polyphenyl substance.
(3) Silane coupling agent modified silicon carbide
And (3) placing the silicon carbide in a vacuum drying oven at 100 ℃ for drying for 8 hours, accurately weighing 15g of dried silicon carbide in a three-necked flask, adding 105mL of toluene and 0.45g of 3-aminopropyl trimethoxy silane into the three-necked flask, introducing nitrogen, heating to 90 ℃ for stirring reaction for 5 hours, performing ultrasonic dispersion, centrifuging at a high speed of 10000r/min for 30 minutes, washing with acetone, and placing the dried silicon carbide in the vacuum drying oven at 110 ℃ for drying for 10 hours to obtain the silicon carbide modified by the silane coupling agent.
(4) Preparation of epoxy resin plugging material for improving stratum bearing capacity
Mixing the benzene substances containing epoxy groups prepared in the step (1) and the polyamino substituted polyphenyl substances prepared in the step (2), heating to 150 ℃ for reaction for 5 hours to obtain a branched epoxy resin polymer, and then mixing the branched epoxy resin polymer and the silicon carbide modified by the silane coupling agent prepared in the step (3) to obtain the epoxy resin plugging material for improving the stratum bearing capacity.
Example 3
(1) Synthesis of benzene substance containing epoxy group
0.1mol of 3-amino-4- (2-phenylbenzopyran-6-yloxy) anisole and 100mL of methanol solution are added into a three-necked flask, a reflux condenser is arranged, after 0.2mol of epichlorohydrin is added dropwise under stirring, the temperature is raised to 75 ℃ for reaction for 4 hours, 30mL of triethylamine is added, the temperature is reduced to 45 ℃ and stirring is carried out for 5 hours, and the benzene substance containing epoxy groups is obtained after purification.
(2) Synthesis of polyamino substituted polyphenyl substances
Adding a mixture of 0.1mol of 6-diphenyl-2, 7-naphthalene diol and 0.25mol of sodium bisulphite dispersed in 80mL of ammonia water solution with the mass fraction of 25% into a three-necked flask, heating to 170 ℃, reacting for 13h under stirring, cooling the reaction mixture to room temperature, adding NaOH aqueous solution to regulate the pH value to be more than 12, drying, and washing to obtain the polyamino substituted polyphenyl substance.
(3) Silane coupling agent modified silicon carbide
And (3) placing the silicon carbide in a vacuum drying oven at 110 ℃ for drying for 6 hours, accurately weighing 20g of dried silicon carbide in a three-necked flask, adding 140mL of toluene and 0.6g of 3-aminopropyl trimethoxy silane into the three-necked flask, introducing nitrogen, heating to 90 ℃ for stirring reaction for 6 hours, performing ultrasonic dispersion, centrifuging at a high speed of 10000r/min for 30 minutes, washing with acetone, and placing in a vacuum drying oven at 100 ℃ for drying for 12 hours to obtain the silicon carbide modified by the silane coupling agent.
(4) Preparation of epoxy resin plugging material for improving stratum bearing capacity
Mixing the benzene substances containing epoxy groups prepared in the step (1) and the polyamino substituted polyphenyl substances prepared in the step (2), heating to 150 ℃ for reaction for 6 hours to obtain a branched epoxy resin polymer, and then mixing the branched epoxy resin polymer and the silicon carbide modified by the silane coupling agent prepared in the step (3) to obtain the epoxy resin plugging material for improving the stratum bearing capacity.
Example 4
(1) Synthesis of benzene substance containing epoxy group
Adding 0.1mol of 2- (2-naphthoxy) aniline and 100mL of methanol solution into a three-necked flask, preparing a reflux condensing device, dropwise adding 0.2mol of epichlorohydrin under stirring, heating to 75 ℃ for reaction for 4 hours, adding 30mL of triethylamine, cooling to 50 ℃, stirring for 5 hours, and purifying to obtain benzene substances containing epoxy groups.
(2) Synthesis of polyamino substituted polyphenyl substances
Adding a mixture of 0.1mol of 6-diphenyl-2, 7-naphthalene diol and 0.25mol of sodium bisulphite dispersed in 80mL of ammonia water solution with the mass fraction of 25% into a three-necked flask, heating to 170 ℃, reacting for 13h under stirring, cooling the reaction mixture to room temperature, adding NaOH aqueous solution to regulate the pH value to be more than 12, drying, and washing to obtain the polyamino substituted polyphenyl substance.
(3) Silane coupling agent modified silicon carbide
And (3) placing the silicon carbide in a vacuum drying oven at 110 ℃ for drying for 6 hours, accurately weighing 25g of dried silicon carbide in a three-necked flask, adding 175mL of toluene and 0.75g of 3-aminopropyl triethoxysilane into the three-necked flask, introducing nitrogen, heating to 90 ℃ for stirring reaction for 6 hours, performing ultrasonic dispersion, centrifuging at a high speed of 10000r/min for 30 minutes, washing with acetone, and placing the dried silicon carbide in the vacuum drying oven at 120 ℃ for drying for 10 hours to obtain the silicon carbide modified by the silane coupling agent.
(4) Preparation of epoxy resin plugging material for improving stratum bearing capacity
Mixing the benzene substances containing epoxy groups prepared in the step (1) and the polyamino substituted polyphenyl substances prepared in the step (2), heating to 150 ℃ for reaction for 7 hours to obtain a branched epoxy resin polymer, and then mixing the branched epoxy resin polymer and the silicon carbide modified by the silane coupling agent prepared in the step (3) to obtain the epoxy resin plugging material for improving the stratum bearing capacity.
Example 5
(1) Synthesis of benzene substance containing epoxy group
Adding 0.1mol of 2- (2-naphthoxy) aniline and 100mL of methanol solution into a three-necked flask, preparing a reflux condenser, dropwise adding 0.2mol of epichlorohydrin under stirring, heating to 75 ℃ for reaction for 4 hours, adding 30mL of triethylamine, cooling to 40 ℃, stirring for 5 hours, and purifying to obtain the benzene substance containing epoxy groups.
(2) Synthesis of polyamino substituted polyphenyl substances
A mixture of 0.1mol of 1,1' - (2, 7-dihydroxy-1, 6-naphthalenediyl) diethyl ketone and 0.25mol of sodium bisulfate dispersed in 80mL of an aqueous ammonia solution with a mass fraction of 25% was added to a three-necked flask, the temperature was raised to 180℃and the mixture was reacted for 14 hours under stirring, after the reaction mixture was cooled to room temperature, an aqueous NaOH solution was added to adjust the pH to more than 12, and the mixture was dried and washed to obtain a polyamino-substituted polyphenyl substance.
(3) Silane coupling agent modified silicon carbide
And (3) placing the silicon carbide in a vacuum drying oven at 90 ℃ for drying for 8 hours, accurately weighing 30g of dried silicon carbide in a three-necked flask, adding 210mL of toluene and 0.9g of 3-aminopropyl triethoxysilane into the three-necked flask, introducing nitrogen, heating to 90 ℃ for stirring reaction for 6 hours, performing ultrasonic dispersion, centrifuging at a high speed of 10000r/min for 30 minutes, washing with acetone, and placing the dried silicon carbide in the vacuum drying oven at 120 ℃ for drying for 10 hours to obtain the silicon carbide modified by the silane coupling agent.
(4) Preparation of epoxy resin plugging material for improving stratum bearing capacity
Mixing the benzene substances containing epoxy groups prepared in the step (1) and the polyamino substituted polyphenyl substances prepared in the step (2), heating to 160 ℃ for reaction for 6 hours to obtain a branched epoxy resin polymer, and then mixing the branched epoxy resin polymer and the silicon carbide modified by the silane coupling agent prepared in the step (3) to obtain the epoxy resin plugging material for improving the stratum bearing capacity.
Comparative example
50g of bisphenol A type epoxy resin and 10g of polyethylene glycol 200 are added into a variable frequency high-speed stirrer to be stirred for 30min, 2.5g of curing agent Q-500 dicyandiamide, 0.3g of accelerator SH-A100 and 1.3g of stabilizer are added, and the mixture is stirred for 6h at 40 ℃ to be uniformly dispersed to obtain the bisphenol A type epoxy resin plugging material.
2. Preparation of oil-based drilling fluid
The invention mainly describes the application mode of the pressure-bearing plugging branched epoxy resin according to the following specific formula. Based on 340 parts by mass of base oil, the specific formula is as follows: white oil # 3, main emulsifier HIEMUL, auxiliary emulsifier HICOAT, wetting agent HIWET, organic soil SMGEL, calcium oxide solution of 20 percent, filtrate reducer SMFLA-O, barite powder and epoxy resin plugging material for improving the bearing capacity of the stratum.
The specific preparation process is as follows: taking 340mL of 3# white oil, adding the 340mL of white oil into a 1000mL stirring cup, adding 13g of main emulsifier HIEMUL,10g of auxiliary emulsifier HICOAT,5g of wetting agent HIWET, stirring at a high speed at 12000r/min for 20min, adding 14g of organic soil SMGEL, stirring at a high speed at 12000r/min for 10min, adding 23g of calcium oxide, stirring at a high speed at 12000r/min for 10min, and slowly adding 60mL of calcium chloride aqueous solution (the mass percent concentration of calcium chloride is 20%), and stirring at a high speed for 20min; then adding 24g of fluid loss agent SMFLA-O, stirring at high speed for 20min, continuously adding 870g of barite, stirring at high speed for 30min to obtain base slurry of oil-based drilling fluid, wherein the density of the prepared drilling fluid is 2g/cm 3 。
3. Performance testing
1. Test for improving compressive property of epoxy resin plugging material with stratum bearing capacity
Samples of the final products of examples 1,2, 3, 4, 5 and comparative examples were tested for their compressive capacity, three sets of samples were taken for each material. Compression test referring to ASTM D6641, two strain gages, one longitudinal and one transverse, are attached to each of the front and rear surfaces of a test piece to obtain the average compressive strain and poisson's ratio of the two surfaces of the test piece, an Instron 5882 tester (measuring range 100 kN) is used, and a combined loading compression clamp (CLC) is used to apply compressive load to the test piece, and the data obtained from the test is averaged. Table 1 shows the compressive strength recording tables of example 1, example 2, example 3, example 4, example 5 and comparative example.
As shown in Table 1, the branched epoxy resin was better in pressure-bearing ability than the bisphenol A-type epoxy resin having a chain-like molecular structure, and the pressure-bearing ability was also enhanced with the increase in the amount of the rigid material particles.
Table 1 epoxy resin compression resistance test
2. Wedge 3mm-4mm crack plugging experiment
Evaluation standard of plugging experiment: the plugging of the crack mainly considers whether the plugging material can quickly form a compact and effective plugging layer in the crack, whether the plugging layer can bear larger pressure and the crack is not extended any more, so that the bearing capacity of the crack is improved, and the concentration of rigid particles is matched with the crack.
According to the above slurry preparation, 19 parts of the same base slurry were prepared, and 0 part by weight, 1 part by weight, 4 parts by weight, and 7 parts by weight of example 1, example 2, example 3, example 4, example 5, and comparative example were added, respectively, to prepare 19 parts of an oil-based drilling fluid having different amounts of epoxy resin plugging material and bisphenol a epoxy resin plugging material for improving the bearing capacity of the stratum, and the base slurry without plugging material was used as a blank experiment group. In order to further illustrate the effect of the epoxy resin plugging material for improving the stratum bearing capacity, the plugging experiment of the wedge plate crack is carried out on the oil-based drilling fluids with different plugging materials.
As can be seen from table 2, after the plugging material is added into the base slurry, plugging can be performed on the crack with the diameter of 3mm to 4mm, and the plugging effect is improved along with the increase of the addition amount of the plugging material, wherein the formula with the best plugging effect is as follows: base stock +7% example 4.
TABLE 2 Experimental results for plugging of wedge 3mm-4mm cracks
The present invention is not limited to the above-mentioned embodiments, but is intended to be limited to the following embodiments, and any modifications, equivalents and modifications can be made to the above-mentioned embodiments without departing from the scope of the invention.
Claims (8)
1. The epoxy resin plugging material is characterized in that the epoxy resin plugging material comprises aniline substances containing ether bonds, epichlorohydrin, dihydroxy-substituted polyphenyl substances, silicon carbide and silane coupling agents, wherein the mole ratio of the aniline substances containing ether bonds, the dihydroxy-substituted polyphenyl substances and the epichlorohydrin is about 1:0.5:2, the preparation method comprises the following steps:
s1, adding aniline substances containing ether bonds and a methanol solution into a three-necked flask, preparing a reflux condensing device, dropwise adding epoxy chloropropane in a stirring state, heating to 65-75 ℃ for reaction for 4-6 hours, adding triethylamine, cooling to 40-60 ℃, stirring for 3-5 hours, and purifying to obtain benzene substances containing epoxy groups;
s2, adding a mixture of dihydroxy-substituted polyphenyl substances and sodium bisulphite dispersed in an ammonia water solution with the mass fraction of 25% into a three-necked flask, heating to 150-180 ℃, reacting for 12-15h under a stirring state, cooling the reaction mixture to room temperature, adding an NaOH aqueous solution to regulate the pH value to be more than 12, drying, and washing to obtain the polyamino-substituted polyphenyl substances;
s3, placing the silicon carbide in a vacuum drying oven at 80-110 ℃ for drying for 6-8 hours, accurately weighing the dried silicon carbide in a three-necked flask, adding toluene and a silane coupling agent into the three-necked flask, introducing nitrogen, heating to 80-90 ℃ for stirring reaction for 5-8 hours, performing ultrasonic dispersion, centrifuging at a high speed of 10000r/min for 30 minutes, washing with acetone, and placing in a vacuum drying oven at 100-120 ℃ for drying for 10-12 hours to obtain the silane coupling agent modified silicon carbide;
s4, mixing the benzene substances containing epoxy groups prepared in the S1 and the polyamino substituted polyphenyl substances prepared in the S2, heating to 130-160 ℃ for reaction for 4-7 hours to obtain a branched epoxy resin polymer, and mixing the branched epoxy resin polymer and silicon carbide modified by the silane coupling agent prepared in the S3 to obtain the epoxy resin plugging material for improving the bearing capacity of the stratum;
the silane coupling agent is one of 3-aminopropyl triethoxysilane and 3-aminopropyl trimethoxysilane.
2. The epoxy resin plugging material for improving the bearing capacity of a stratum according to claim 1, wherein the aniline substance containing ether bonds is one of 3-amino-4- (2-phenylbenzopyran-6-yloxy) anisole and 2- (2-naphthoxy) aniline.
3. The epoxy resin plugging material for improving the bearing capacity of a stratum according to claim 1, wherein the dihydroxy-substituted polyphenyl substance is one of 5, 8-dihydroxy-10-methoxy-2-methyl-4H-naphthalene [1,2-b ] pyran-4-one, 5, 8-dihydroxy-6, 10-dimethoxy-2-methyl-4H-naphthalene [1,2-b ] pyran-4-one, 6-diphenyl-2, 7-naphthalene diol, 1' - (2, 7-dihydroxy-1, 6-naphthalene diyl) diethyl ketone.
4. The epoxy resin plugging material for improving the bearing capacity of a stratum according to claim 1, wherein the epoxy resin is branched.
5. An oil-based drilling fluid, which is characterized in that the epoxy resin plugging material for improving the bearing capacity of the stratum is added in the drilling fluid.
6. The oil-based drilling fluid of claim 5, wherein the drilling fluid comprises the following components: base oil, main emulsifier, auxiliary emulsifier, wetting agent, organic soil, calcium oxide, water phase, fluid loss agent, plugging material and weighting agent.
7. The oil-based drilling fluid of claim 6, wherein the base oil is a 3# white oil, the primary emulsifier is HIEMUL, the secondary emulsifier is HICOAT, the wetting agent is HIWET, the organic soil is SMGEL, the aqueous phase is a 20% calcium chloride solution, the fluid loss additive is SMFLA-O, the lost circulation material is the epoxy resin of claim 1 that increases the formation bearing capacity, and the weighting agent is barite powder.
8. The oil-based drilling fluid according to claim 7, wherein the drilling fluid comprises the following components in parts by weight: 340 parts of No. 3 white oil, 12-13 parts of main emulsifier HIEMUL,8-10 parts of auxiliary emulsifier HICOAT,4-5 parts of wetting agent HIWET,12-14 parts of organic soil SMGEL,20-23 parts of calcium oxide, 20-24 parts of filtrate reducer SMFLA-O,60 parts of 20% calcium chloride solution, 4-28 parts of epoxy resin for improving the bearing capacity of stratum, 660-870 parts of barite powder and drilling fluid density of 1.8-2.0g/cm 3 。
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117568000A (en) * | 2024-01-15 | 2024-02-20 | 东营市汇友石油新技术开发有限责任公司 | Differential pressure plugging agent and preparation process thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2935337A1 (en) * | 2014-02-21 | 2015-08-27 | Halliburton Energy Services Inc. | Cementing compositions and methods |
| US20160326300A1 (en) * | 2013-12-27 | 2016-11-10 | 3M Innovative Properties Company | Crosslinked epoxy particles and methods for making and using the same |
| CN109705827A (en) * | 2017-10-25 | 2019-05-03 | 中国石油化工股份有限公司 | Oil drilling leak stopping pressure-bearing agent and preparation method thereof |
| CN114163776A (en) * | 2022-01-24 | 2022-03-11 | 西南石油大学 | Epoxy resin with pressure-bearing and leakage-stopping functions and preparation method thereof |
| CN114381247A (en) * | 2022-01-24 | 2022-04-22 | 西南石油大学 | Synthesis of branched epoxy resin pressure-bearing plugging material |
-
2023
- 2023-07-27 CN CN202310928395.0A patent/CN116948615A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160326300A1 (en) * | 2013-12-27 | 2016-11-10 | 3M Innovative Properties Company | Crosslinked epoxy particles and methods for making and using the same |
| CA2935337A1 (en) * | 2014-02-21 | 2015-08-27 | Halliburton Energy Services Inc. | Cementing compositions and methods |
| CN109705827A (en) * | 2017-10-25 | 2019-05-03 | 中国石油化工股份有限公司 | Oil drilling leak stopping pressure-bearing agent and preparation method thereof |
| CN114163776A (en) * | 2022-01-24 | 2022-03-11 | 西南石油大学 | Epoxy resin with pressure-bearing and leakage-stopping functions and preparation method thereof |
| CN114381247A (en) * | 2022-01-24 | 2022-04-22 | 西南石油大学 | Synthesis of branched epoxy resin pressure-bearing plugging material |
Non-Patent Citations (2)
| Title |
|---|
| YANG, CP ; LEE, LT ; YU, WT: "SYNTHESIS AND PROPERTIES OF CATIONIC RESINS DERIVED FROM ANILINE-MODIFIED EPOXY-RESINS AND VARIOUS AMINES", JOURNAL OF APPLIED POLYMER SCIENCE, vol. 42, no. 5, 5 March 1991 (1991-03-05), pages 1465 - 1474 * |
| 曾娟娟;陈绪港;张文超;: "环保型环氧树脂堵漏材料的固化行为研究", 中国建筑防水, no. 05, 15 May 2020 (2020-05-15) * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117568000A (en) * | 2024-01-15 | 2024-02-20 | 东营市汇友石油新技术开发有限责任公司 | Differential pressure plugging agent and preparation process thereof |
| CN117568000B (en) * | 2024-01-15 | 2024-03-29 | 东营市汇友石油新技术开发有限责任公司 | Differential pressure plugging agent and preparation process thereof |
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