CN118638537A - A pressure-reducing and injection-increasing surfactant and its preparation method - Google Patents
A pressure-reducing and injection-increasing surfactant and its preparation method Download PDFInfo
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 44
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000002041 carbon nanotube Substances 0.000 claims abstract description 23
- 229910021393 carbon nanotube Inorganic materials 0.000 claims abstract description 23
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000002347 injection Methods 0.000 claims abstract description 16
- 239000007924 injection Substances 0.000 claims abstract description 16
- 238000003756 stirring Methods 0.000 claims abstract description 16
- -1 trimethylsilyl glucoside Chemical class 0.000 claims abstract description 16
- 229930182478 glucoside Natural products 0.000 claims abstract description 11
- ZIWRUEGECALFST-UHFFFAOYSA-M sodium 4-(4-dodecoxysulfonylphenoxy)benzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCOS(=O)(=O)c1ccc(Oc2ccc(cc2)S([O-])(=O)=O)cc1 ZIWRUEGECALFST-UHFFFAOYSA-M 0.000 claims abstract description 11
- 239000005543 nano-size silicon particle Substances 0.000 claims abstract description 10
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 20
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 16
- 238000001035 drying Methods 0.000 claims description 16
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims description 15
- 238000005406 washing Methods 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 12
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 10
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 10
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 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
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 5
- 239000008367 deionised water Substances 0.000 claims description 5
- 229910021641 deionized water Inorganic materials 0.000 claims description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000002390 rotary evaporation Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims 3
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical group CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 claims 1
- QXLPXWSKPNOQLE-UHFFFAOYSA-N methylpentynol Chemical compound CCC(C)(O)C#C QXLPXWSKPNOQLE-UHFFFAOYSA-N 0.000 claims 1
- 238000001132 ultrasonic dispersion Methods 0.000 claims 1
- 239000011435 rock Substances 0.000 abstract description 6
- 239000004927 clay Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 230000008859 change Effects 0.000 abstract description 3
- 239000002120 nanofilm Substances 0.000 abstract description 3
- 230000035699 permeability Effects 0.000 abstract description 3
- 239000011148 porous material Substances 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 238000006467 substitution reaction Methods 0.000 abstract description 2
- 239000000377 silicon dioxide Substances 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 4
- 238000002525 ultrasonication Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002332 oil field water Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000009671 shengli Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
- C01B32/158—Carbon nanotubes
- C01B32/168—After-treatment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/113—Silicon oxides; Hydrates thereof
- C01B33/12—Silica; Hydrates thereof, e.g. lepidoic silicic acid
- C01B33/18—Preparation of finely divided silica neither in sol nor in gel form; After-treatment thereof
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- 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
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
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- 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
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
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- General Life Sciences & Earth Sciences (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
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Abstract
本发明涉及油田化学技术领域，且公开了一种降压增注表面活性剂及其制备方法，本发明通过将季铵化碳纳米管、金刚烷改性纳米二氧化硅、十二烷基二苯醚双磺酸钠、甲基戊醇、三甲基硅烷基葡萄糖苷、水加入到反应釜中，搅拌，得到降压增注表面活性剂；降压增注表面活性剂中的季铵盐基团和金刚烷结构可以降低油水界面的张力、抑制粘土膨胀，提高注入水的渗透能力，起到降压增注的作用；中间体2中含有大量的羟基基团，给碳纳米管提高了接枝位点，提高了其取代度，碳纳米管可以防止粘土膨胀，能够在岩石表面形成一层纳米膜，这层膜能改变岩石的润湿性，从而减少水流在岩石孔道中的流动阻力，达到降低注水压力的效果；纳米二氧化硅本身也可以降压增注。The invention relates to the technical field of oilfield chemistry, and discloses a pressure-reducing and injection-increasing surfactant and a preparation method thereof. The invention provides a pressure-reducing and injection-increasing surfactant by adding quaternized carbon nanotubes, adamantane-modified nano silicon dioxide, sodium dodecyl diphenyl ether disulfonate, methyl amyl alcohol, trimethylsilyl glucoside and water into a reaction kettle and stirring the mixture. The pressure-reducing and injection-increasing surfactant can reduce the tension of the oil-water interface and inhibit clay expansion, thereby improving the permeability of injected water and playing the role of pressure-reducing and injection-increasing. The intermediate 2 contains a large number of hydroxyl groups, which increases the grafting sites and substitution degree of the carbon nanotubes. The carbon nanotubes can prevent clay expansion and form a nano film on the surface of the rock. The nano film can change the wettability of the rock, thereby reducing the flow resistance of water in the rock pores and achieving the effect of reducing the injection pressure. The nano silicon dioxide itself can also reduce the pressure and injection-increasing.
Description
技术领域Technical Field
本发明涉及油田化学技术领域，具体为一种降压增注表面活性剂及其制备方法。The invention relates to the technical field of oilfield chemistry, in particular to a pressure-reducing and injection-increasing surfactant and a preparation method thereof.
背景技术Background Art
由于低渗透油藏储层泥质含量高，孔道细，毛管力作用显著等特点，因此，为确保注水井注上水并保持一定的注水量，注水泵压不断提高，所以开发中的主要矛盾是注水压力高、单井注水量小，水驱波及体积小，降低了采油效率，国内普遍采取在注水的过程中，加入降压增注表面活性剂，来改善水驱效果，如专利CN112552893A公布了一种分子膜降压增注表面活性剂及其制备方法，该申请提供的分子膜降压增注表面活性剂的制备方法制备的分子膜降压增注表面活性剂能够有效降低油水界面张力，改变润湿性，且与注入水和油层之间具有较好的配伍性，但是其组分类型较单一，降压增注率不高，因此如何避免这一现象，是解决问题的关键。Due to the characteristics of low permeability oil reservoirs such as high mud content, fine pores, and significant capillary force, in order to ensure that water is injected into the injection wells and maintain a certain injection volume, the injection pump pressure is continuously increased. Therefore, the main contradiction in development is high injection pressure, small single well water injection volume, small water drive swept volume, and reduced oil recovery efficiency. In China, it is generally adopted to add pressure-reducing and injection-increasing surfactants during the water injection process to improve the water drive effect. For example, patent CN112552893A discloses a molecular membrane pressure-reducing and injection-increasing surfactant and a preparation method thereof. The molecular membrane pressure-reducing and injection-increasing surfactant prepared by the preparation method of the molecular membrane pressure-reducing and injection-increasing surfactant provided in the application can effectively reduce the oil-water interfacial tension, change the wettability, and has good compatibility with the injected water and the oil layer. However, its component type is relatively single and the pressure-reducing and injection-increasing rate is not high. Therefore, how to avoid this phenomenon is the key to solving the problem.
发明内容Summary of the invention
（一）解决的技术问题1. Technical issues to be resolved
针对现有技术的不足，本发明提供了一种降压增注表面活性剂及其制备方法，降低了注水压力和油水界面张力、提高了水相渗透率。In view of the deficiencies of the prior art, the present invention provides a pressure-reducing and injection-increasing surfactant and a preparation method thereof, which reduces the injection pressure and the oil-water interfacial tension and improves the water phase permeability.
（二）技术方案(II) Technical solution
为实现上述目的，本发明提供以下技术方案：一种降压增注表面活性剂，包括以下重量组分：4-5重量份的季铵化碳纳米管、4-6重量份的金刚烷改性纳米二氧化硅、2-3重量份的十二烷基二苯醚双磺酸钠、1-3重量份的甲基戊醇、1-2重量份的三甲基硅烷基葡萄糖苷、3-4重量份的水。To achieve the above-mentioned purpose, the present invention provides the following technical scheme: a pressure-reducing and injection-increasing surfactant, comprising the following components by weight: 4-5 parts by weight of quaternized carbon nanotubes, 4-6 parts by weight of adamantane-modified nano-silica, 2-3 parts by weight of sodium dodecyl diphenyl ether disulfonate, 1-3 parts by weight of methyl amyl alcohol, 1-2 parts by weight of trimethylsilyl glucoside, and 3-4 parts by weight of water.
优选的，所述季铵化碳纳米管的制备方法为：Preferably, the preparation method of the quaternized carbon nanotubes is:
（1）向二甲基亚砜溶剂中加入5-氨基间苯二甲酸和丙烯酰氯，搅拌溶解，继续加入氢氧化钠，然后在15-20℃下反应16-20h，结束后滴加质量分数为10-14%的盐酸溶液调节溶液pH为2-2.5，结束后减压蒸馏，丙酮洗涤，过滤并干燥，得到烯基化二甲酸；(1) Add 5-aminoisophthalic acid and acryloyl chloride to dimethyl sulfoxide solvent, stir to dissolve, continue to add sodium hydroxide, and then react at 15-20°C for 16-20 hours. After the reaction, add a 10-14% hydrochloric acid solution to adjust the pH of the solution to 2-2.5. After the reaction, distill under reduced pressure, wash with acetone, filter and dry to obtain olefinated dicarboxylic acid;
（2）将烯基化二甲酸、羟乙基乙二胺、磷酸加入到反应器中，通入氮气保护，在135-150℃下反应3-6h，继续在195-200℃下进行加热，除去羟乙基乙二胺，过滤，洗涤并干燥，得到中间体1；(2) Add olefinic dicarboxylic acid, hydroxyethylethylenediamine and phosphoric acid into a reactor, introduce nitrogen protection, react at 135-150°C for 3-6 hours, continue heating at 195-200°C, remove hydroxyethylethylenediamine, filter, wash and dry to obtain intermediate 1;
（3）向N,N-二甲基甲酰胺溶剂中加入5-12重量份的中间体1和7-9重量份的2-溴乙醇，搅拌均匀，在75-90℃下回流反应，然后继续向其加入8-10重量份的丙烯醇和6-9重量份的过硫酸铵，在90-110℃下反应7-12h，结束后旋转蒸发，乙醇重结晶，得到中间体2；(3) Add 5-12 parts by weight of intermediate 1 and 7-9 parts by weight of 2-bromoethanol to N,N-dimethylformamide solvent, stir evenly, reflux at 75-90°C, then continue to add 8-10 parts by weight of propylene alcohol and 6-9 parts by weight of ammonium persulfate, react at 90-110°C for 7-12 hours, and then rotary evaporate after reaction, and recrystallize from ethanol to obtain intermediate 2;
（4）将8-15重量份的羟基化碳纳米管加入到N,N-二甲基甲酰胺溶剂中，超声分散，继续向其加入6-8重量份的六亚甲基二异氰酸酯和9-15重量份的中间体2，升温反应7-12h，结束后离心分离，乙醇洗涤，干燥，得到季铵化碳纳米管。(4) Add 8-15 parts by weight of hydroxylated carbon nanotubes to N,N-dimethylformamide solvent, disperse by ultrasonication, and continue to add 6-8 parts by weight of hexamethylene diisocyanate and 9-15 parts by weight of intermediate 2, heat the reaction for 7-12 hours, centrifuge after reaction, wash with ethanol, and dry to obtain quaternized carbon nanotubes.
优选的，所述（1）中5-氨基间苯二甲酸、丙烯酰氯、氢氧化钠的质量比为2.2-3:1:1.1-1.2。Preferably, the mass ratio of 5-aminoisophthalic acid, acryloyl chloride and sodium hydroxide in (1) is 2.2-3:1:1.1-1.2.
优选的，所述（2）中烯基化二甲酸、羟乙基乙二胺、磷酸的质量比为1:1.3-1.5:0.01-0.03。Preferably, the mass ratio of olefinic dicarboxylic acid, hydroxyethylethylenediamine and phosphoric acid in (2) is 1:1.3-1.5:0.01-0.03.
优选的，所述（3）中反应时间为32-35h。Preferably, the reaction time in (3) is 32-35 hours.
优选的，所述（4）中反应温度为80-95℃。Preferably, the reaction temperature in (4) is 80-95°C.
优选的，所述金刚烷改性纳米二氧化硅的制备方法为：Preferably, the preparation method of the adamantane-modified nano-silica is:
S1.将6-10重量份的纳米二氧化硅超声分散到15-30重量份的无水乙醇和8-10重量份的去离子水混合溶液中，混合均匀后，加入5-9重量份的γ-氨丙基三乙氧基硅烷，在70-85℃下反应20-25h，反应后离心，洗涤并干燥，得到氨基化纳米二氧化硅；S1. 6-10 parts by weight of nano-silica are ultrasonically dispersed into a mixed solution of 15-30 parts by weight of anhydrous ethanol and 8-10 parts by weight of deionized water, mixed evenly, and then 5-9 parts by weight of γ-aminopropyltriethoxysilane are added, reacted at 70-85 ° C for 20-25h, centrifuged after the reaction, washed and dried to obtain amino nano-silica;
S2.向N,N-二甲基甲酰胺溶剂中加入3-6重量份的氨基化纳米二氧化硅、2-4重量份的烷基二酰氯和5-8重量份的3-羟基-1-金刚烷甲醇，在50-75℃下反应10-14h，结束后减压蒸馏，过滤并干燥，得到金刚烷改性纳米二氧化硅。S2. Add 3-6 parts by weight of amino-modified nano-silica, 2-4 parts by weight of alkyl diacyl chloride and 5-8 parts by weight of 3-hydroxy-1-adamantane methanol to N,N-dimethylformamide solvent, react at 50-75°C for 10-14h, and then distill under reduced pressure, filter and dry to obtain adamantane-modified nano-silica.
优选的，所述的降压增注表面活性剂的制备方法为：将季铵化碳纳米管、金刚烷改性纳米二氧化硅、十二烷基二苯醚双磺酸钠、甲基戊醇、三甲基硅烷基葡萄糖苷、水加入到反应釜中，在25-30℃下搅拌20-30min，得到降压增注表面活性剂。Preferably, the preparation method of the pressure-reducing and injection-increasing surfactant is: adding quaternized carbon nanotubes, adamantane-modified nano-silica, sodium dodecyl diphenyl ether disulfonate, methyl amyl alcohol, trimethylsilyl glucoside, and water into a reaction kettle, stirring at 25-30° C. for 20-30 minutes to obtain the pressure-reducing and injection-increasing surfactant.
（三）有益的技术效果3. Beneficial technical effects
本发明通过将季铵化碳纳米管、金刚烷改性纳米二氧化硅、十二烷基二苯醚双磺酸钠、甲基戊醇、三甲基硅烷基葡萄糖苷、水加入到反应釜中，搅拌，得到降压增注表面活性剂。The invention adds quaternized carbon nanotubes, adamantane-modified nano silicon dioxide, sodium dodecyl diphenyl ether disulfonate, methyl amyl alcohol, trimethylsilyl glucoside and water into a reaction kettle, and stirs the mixture to obtain a pressure-reducing and injection-increasing surfactant.
降压增注表面活性剂中的季铵盐基团和金刚烷结构可以降低油水界面的张力、抑制粘土膨胀，提高注入水的渗透能力，起到降压增注的作用；中间体2中含有大量的羟基基团，给碳纳米管提高了接枝位点，提高了其取代度，碳纳米管可以防止粘土膨胀，能够在岩石表面形成一层纳米膜，这层膜能显著改变岩石的润湿性，从而减少水流在岩石孔道中的流动阻力，达到降低注水压力的效果；纳米二氧化硅本身也可以降压增注。The quaternary ammonium salt group and adamantane structure in the pressure-reducing and injection-increasing surfactant can reduce the tension of the oil-water interface, inhibit clay expansion, and improve the penetration capacity of the injected water, thereby playing a role in pressure reduction and injection-increasing; intermediate 2 contains a large number of hydroxyl groups, which increase the grafting sites of carbon nanotubes and their degree of substitution. Carbon nanotubes can prevent clay expansion and can form a nanofilm on the rock surface. This film can significantly change the wettability of the rock, thereby reducing the flow resistance of water in the rock pores and achieving the effect of reducing the injection pressure; nano-silica itself can also reduce pressure and increase injection.
具体实施方式DETAILED DESCRIPTION
羟基化碳纳米管的制备：将0.3g的碳纳米管加入到体积比为3:1的浓硫酸和浓硝酸中进行酸化，得到羟基化碳纳米管。Preparation of hydroxylated carbon nanotubes: 0.3 g of carbon nanotubes were added into concentrated sulfuric acid and concentrated nitric acid in a volume ratio of 3:1 for acidification to obtain hydroxylated carbon nanotubes.
实施例1Example 1
（1）向二甲基亚砜溶剂中加入5-氨基间苯二甲酸和丙烯酰氯，搅拌溶解，继续加入氢氧化钠，其中5-氨基间苯二甲酸、丙烯酰氯、氢氧化钠的质量比为2.2:1:1.1，然后在15℃下反应16h，结束后滴加质量分数为10%的盐酸溶液调节溶液pH为2，结束后减压蒸馏，丙酮洗涤，过滤并干燥，得到烯基化二甲酸；(1) Add 5-aminoisophthalic acid and acryloyl chloride to dimethyl sulfoxide solvent, stir to dissolve, continue to add sodium hydroxide, wherein the mass ratio of 5-aminoisophthalic acid, acryloyl chloride and sodium hydroxide is 2.2:1:1.1, and then react at 15°C for 16 hours. After the reaction, add a 10% hydrochloric acid solution by mass to adjust the pH of the solution to 2. After the reaction, distill under reduced pressure, wash with acetone, filter and dry to obtain olefinated dicarboxylic acid;
（2）将烯基化二甲酸、羟乙基乙二胺、磷酸加入到反应器中，其中烯基化二甲酸、羟乙基乙二胺、磷酸的质量比为1:1.3:0.01，通入氮气保护，在135℃下反应3h，继续在195℃下进行加热，除去羟乙基乙二胺，过滤，洗涤并干燥，得到中间体1；(2) Adding olefinic dicarboxylic acid, hydroxyethylethylenediamine and phosphoric acid into a reactor, wherein the mass ratio of olefinic dicarboxylic acid, hydroxyethylethylenediamine and phosphoric acid is 1:1.3:0.01, introducing nitrogen protection, reacting at 135°C for 3 hours, and continuing to heat at 195°C to remove hydroxyethylethylenediamine, filtering, washing and drying to obtain intermediate 1;
（3）向N,N-二甲基甲酰胺溶剂中加入5重量份的中间体1和7重量份的2-溴乙醇，搅拌均匀，在75℃下回流反应32h，然后继续向其加入8重量份的丙烯醇和6重量份的过硫酸铵，在90℃下反应7h，结束后旋转蒸发，乙醇重结晶，得到中间体2；(3) Add 5 parts by weight of intermediate 1 and 7 parts by weight of 2-bromoethanol to N,N-dimethylformamide solvent, stir evenly, and reflux at 75°C for 32 hours. Then, add 8 parts by weight of propylene alcohol and 6 parts by weight of ammonium persulfate, and react at 90°C for 7 hours. After the reaction, rotary evaporate and recrystallize from ethanol to obtain intermediate 2.
（4）将8重量份的羟基化碳纳米管加入到N,N-二甲基甲酰胺溶剂中，超声分散，继续向其加入6重量份的六亚甲基二异氰酸酯和9重量份的中间体2，升温至80℃反应7h，结束后离心分离，乙醇洗涤，干燥，得到季铵化碳纳米管；(4) adding 8 parts by weight of hydroxylated carbon nanotubes to N,N-dimethylformamide solvent, dispersing by ultrasonication, adding 6 parts by weight of hexamethylene diisocyanate and 9 parts by weight of intermediate 2, heating to 80° C. for 7 h, centrifuging after reaction, washing with ethanol, and drying to obtain quaternized carbon nanotubes;
（5）将6重量份的纳米二氧化硅超声分散到15重量份的无水乙醇和8重量份的去离子水混合溶液中，混合均匀后，加入5重量份的γ-氨丙基三乙氧基硅烷，在70℃下反应20h，反应后离心，洗涤并干燥，得到氨基化纳米二氧化硅；(5) ultrasonically dispersing 6 parts by weight of nano-silica into a mixed solution of 15 parts by weight of anhydrous ethanol and 8 parts by weight of deionized water, mixing evenly, adding 5 parts by weight of γ-aminopropyltriethoxysilane, reacting at 70° C. for 20 h, centrifuging after the reaction, washing and drying to obtain amino-modified nano-silica;
（6）向N,N-二甲基甲酰胺溶剂中加入3重量份的氨基化纳米二氧化硅、2重量份的烷基二酰氯和5重量份的3-羟基-1-金刚烷甲醇，在50℃下反应10h，结束后减压蒸馏，过滤并干燥，得到金刚烷改性纳米二氧化硅；(6) Add 3 parts by weight of amino-modified nano-silica, 2 parts by weight of alkyl diacyl chloride and 5 parts by weight of 3-hydroxy-1-adamantane methanol to N,N-dimethylformamide solvent, react at 50° C. for 10 h, and then perform vacuum distillation, filter and dry to obtain adamantane-modified nano-silica;
（7）将4重量份的季铵化碳纳米管、4重量份的金刚烷改性纳米二氧化硅、2重量份的十二烷基二苯醚双磺酸钠、1重量份的甲基戊醇、1重量份的三甲基硅烷基葡萄糖苷、3重量份的水加入到反应釜中，在25℃下搅拌20min，得到降压增注表面活性剂。(7) 4 parts by weight of quaternized carbon nanotubes, 4 parts by weight of adamantane-modified nano-silica, 2 parts by weight of sodium dodecyl diphenyl ether disulfonate, 1 part by weight of methyl amyl alcohol, 1 part by weight of trimethylsilyl glucoside, and 3 parts by weight of water were added into a reactor and stirred at 25° C. for 20 min to obtain a pressure-reducing and injection-increasing surfactant.
实施例2Example 2
（1）向二甲基亚砜溶剂中加入5-氨基间苯二甲酸和丙烯酰氯，搅拌溶解，继续加入氢氧化钠，其中5-氨基间苯二甲酸、丙烯酰氯、氢氧化钠的质量比为3:1:1.2，然后在20℃下反应20h，结束后滴加质量分数为14%的盐酸溶液调节溶液pH为2.5，结束后减压蒸馏，丙酮洗涤，过滤并干燥，得到烯基化二甲酸；(1) Add 5-aminoisophthalic acid and acryloyl chloride to dimethyl sulfoxide solvent, stir to dissolve, continue to add sodium hydroxide, wherein the mass ratio of 5-aminoisophthalic acid, acryloyl chloride and sodium hydroxide is 3:1:1.2, and then react at 20°C for 20 hours. After the reaction, add a 14% hydrochloric acid solution by mass to adjust the solution pH to 2.5. After the reaction, distill under reduced pressure, wash with acetone, filter and dry to obtain olefinated dicarboxylic acid;
（2）将烯基化二甲酸、羟乙基乙二胺、磷酸加入到反应器中，其中烯基化二甲酸、羟乙基乙二胺、磷酸的质量比为1:1.5:0.03，通入氮气保护，在150℃下反应6h，继续在200℃下进行加热，除去羟乙基乙二胺，过滤，洗涤并干燥，得到中间体1；(2) Adding olefinic dicarboxylic acid, hydroxyethylethylenediamine and phosphoric acid into a reactor, wherein the mass ratio of olefinic dicarboxylic acid, hydroxyethylethylenediamine and phosphoric acid is 1:1.5:0.03, introducing nitrogen protection, reacting at 150°C for 6 hours, and continuing to heat at 200°C to remove hydroxyethylethylenediamine, filtering, washing and drying to obtain intermediate 1;
（3）向N,N-二甲基甲酰胺溶剂中加入12重量份的中间体1和9重量份的2-溴乙醇，搅拌均匀，在90℃下回流反应35h，然后继续向其加入10重量份的丙烯醇和9重量份的过硫酸铵，在110℃下反应12h，结束后旋转蒸发，乙醇重结晶，得到中间体2；(3) Add 12 parts by weight of intermediate 1 and 9 parts by weight of 2-bromoethanol to N,N-dimethylformamide solvent, stir evenly, and reflux at 90°C for 35 hours. Then, add 10 parts by weight of propylene alcohol and 9 parts by weight of ammonium persulfate, and react at 110°C for 12 hours. After the reaction, perform rotary evaporation and recrystallize from ethanol to obtain intermediate 2.
（4）将15重量份的羟基化碳纳米管加入到N,N-二甲基甲酰胺溶剂中，超声分散，继续向其加入8重量份的六亚甲基二异氰酸酯和15重量份的中间体2，升温至95℃反应12h，结束后离心分离，乙醇洗涤，干燥，得到季铵化碳纳米管；(4) adding 15 parts by weight of hydroxylated carbon nanotubes to N,N-dimethylformamide solvent, dispersing by ultrasonication, adding 8 parts by weight of hexamethylene diisocyanate and 15 parts by weight of intermediate 2, heating to 95° C. for 12 h, centrifuging after reaction, washing with ethanol, and drying to obtain quaternized carbon nanotubes;
（5）将10重量份的纳米二氧化硅超声分散到30重量份的无水乙醇和10重量份的去离子水混合溶液中，混合均匀后，加入9重量份的γ-氨丙基三乙氧基硅烷，在85℃下反应25h，反应后离心，洗涤并干燥，得到氨基化纳米二氧化硅；(5) ultrasonically dispersing 10 parts by weight of nano-silica into a mixed solution of 30 parts by weight of anhydrous ethanol and 10 parts by weight of deionized water, and after mixing evenly, adding 9 parts by weight of γ-aminopropyltriethoxysilane, reacting at 85° C. for 25 hours, centrifuging after the reaction, washing and drying to obtain amino-modified nano-silica;
（6）向N,N-二甲基甲酰胺溶剂中加入6重量份的氨基化纳米二氧化硅、4重量份的烷基二酰氯和8重量份的3-羟基-1-金刚烷甲醇，在75℃下反应14h，结束后减压蒸馏，过滤并干燥，得到金刚烷改性纳米二氧化硅；(6) adding 6 parts by weight of amino-modified nano-silica, 4 parts by weight of alkyl diacyl chloride and 8 parts by weight of 3-hydroxy-1-adamantane methanol to N,N-dimethylformamide solvent, reacting at 75° C. for 14 h, and then performing reduced pressure distillation, filtering and drying to obtain adamantane-modified nano-silica;
（7）将5重量份的季铵化碳纳米管、6重量份的金刚烷改性纳米二氧化硅、3重量份的十二烷基二苯醚双磺酸钠、3重量份的甲基戊醇、2重量份的三甲基硅烷基葡萄糖苷、4重量份的水加入到反应釜中，在30℃下搅拌30min，得到降压增注表面活性剂。(7) Add 5 parts by weight of quaternized carbon nanotubes, 6 parts by weight of adamantane-modified nano-silica, 3 parts by weight of sodium dodecyl diphenyl ether disulfonate, 3 parts by weight of methyl amyl alcohol, 2 parts by weight of trimethylsilyl glucoside, and 4 parts by weight of water into a reactor, and stir at 30° C. for 30 min to obtain a pressure-reducing and injection-increasing surfactant.
实施例3Example 3
（1）向二甲基亚砜溶剂中加入5-氨基间苯二甲酸和丙烯酰氯，搅拌溶解，继续加入氢氧化钠，其中5-氨基间苯二甲酸、丙烯酰氯、氢氧化钠的质量比为2.6:1:1.15，然后在17.5℃下反应18h，结束后滴加质量分数为12%的盐酸溶液调节溶液pH为2.25，结束后减压蒸馏，丙酮洗涤，过滤并干燥，得到烯基化二甲酸；(1) Add 5-aminoisophthalic acid and acryloyl chloride to dimethyl sulfoxide solvent, stir to dissolve, continue to add sodium hydroxide, wherein the mass ratio of 5-aminoisophthalic acid, acryloyl chloride and sodium hydroxide is 2.6:1:1.15, and then react at 17.5°C for 18 hours. After the reaction, add a 12% hydrochloric acid solution by mass to adjust the solution pH to 2.25. After the reaction, distill under reduced pressure, wash with acetone, filter and dry to obtain olefinated dicarboxylic acid;
（2）将烯基化二甲酸、羟乙基乙二胺、磷酸加入到反应器中，其中烯基化二甲酸、羟乙基乙二胺、磷酸的质量比为1:1.4:0.02，通入氮气保护，在142.5℃下反应4.5h，继续在197.5℃下进行加热，除去羟乙基乙二胺，过滤，洗涤并干燥，得到中间体1；(2) Adding olefinic dicarboxylic acid, hydroxyethylethylenediamine and phosphoric acid into a reactor, wherein the mass ratio of olefinic dicarboxylic acid, hydroxyethylethylenediamine and phosphoric acid is 1:1.4:0.02, introducing nitrogen protection, reacting at 142.5°C for 4.5 hours, and continuing to heat at 197.5°C to remove hydroxyethylethylenediamine, filtering, washing and drying to obtain intermediate 1;
（3）向N,N-二甲基甲酰胺溶剂中加入8.5重量份的中间体1和8重量份的2-溴乙醇，搅拌均匀，在82.5℃下回流反应33.5h，然后继续向其加入9重量份的丙烯醇和7.5重量份的过硫酸铵，在100℃下反应9.5h，结束后旋转蒸发，乙醇重结晶，得到中间体2；(3) Add 8.5 parts by weight of intermediate 1 and 8 parts by weight of 2-bromoethanol to N,N-dimethylformamide solvent, stir evenly, reflux at 82.5°C for 33.5 hours, then continue to add 9 parts by weight of propylene alcohol and 7.5 parts by weight of ammonium persulfate, react at 100°C for 9.5 hours, and then rotary evaporate and recrystallize from ethanol to obtain intermediate 2;
（4）将11.5重量份的羟基化碳纳米管加入到N,N-二甲基甲酰胺溶剂中，超声分散，继续向其加入7重量份的六亚甲基二异氰酸酯和12重量份的中间体2，升温至87.5℃反应9.5h，结束后离心分离，乙醇洗涤，干燥，得到季铵化碳纳米管；(4) adding 11.5 parts by weight of hydroxylated carbon nanotubes to N,N-dimethylformamide solvent, dispersing by ultrasonication, adding 7 parts by weight of hexamethylene diisocyanate and 12 parts by weight of intermediate 2, heating to 87.5°C for 9.5 hours, centrifuging after reaction, washing with ethanol, and drying to obtain quaternized carbon nanotubes;
（5）将8重量份的纳米二氧化硅超声分散到22.5重量份的无水乙醇和9重量份的去离子水混合溶液中，混合均匀后，加入7重量份的γ-氨丙基三乙氧基硅烷，在77.5℃下反应22.5h，反应后离心，洗涤并干燥，得到氨基化纳米二氧化硅；(5) ultrasonically dispersing 8 parts by weight of nano-silica into a mixed solution of 22.5 parts by weight of anhydrous ethanol and 9 parts by weight of deionized water, and after mixing evenly, adding 7 parts by weight of γ-aminopropyltriethoxysilane, reacting at 77.5° C. for 22.5 hours, centrifuging after the reaction, washing and drying to obtain amino-modified nano-silica;
（6）向N,N-二甲基甲酰胺溶剂中加入4.5重量份的氨基化纳米二氧化硅、3重量份的烷基二酰氯和6.5重量份的3-羟基-1-金刚烷甲醇，在62.5℃下反应12h，结束后减压蒸馏，过滤并干燥，得到金刚烷改性纳米二氧化硅；(6) adding 4.5 parts by weight of amino-modified nano-silica, 3 parts by weight of alkyl diacyl chloride and 6.5 parts by weight of 3-hydroxy-1-adamantane methanol to N,N-dimethylformamide solvent, reacting at 62.5° C. for 12 h, and then performing reduced pressure distillation, filtering and drying to obtain adamantane-modified nano-silica;
（7）将4.5重量份的季铵化碳纳米管、5重量份的金刚烷改性纳米二氧化硅、2.5重量份的十二烷基二苯醚双磺酸钠、2重量份的甲基戊醇、1.5重量份的三甲基硅烷基葡萄糖苷、3.5重量份的水加入到反应釜中，在27.5℃下搅拌25min，得到降压增注表面活性剂。(7) 4.5 parts by weight of quaternized carbon nanotubes, 5 parts by weight of adamantane-modified nano-silica, 2.5 parts by weight of sodium dodecyl diphenyl ether disulfonate, 2 parts by weight of methyl amyl alcohol, 1.5 parts by weight of trimethylsilyl glucoside, and 3.5 parts by weight of water were added into a reactor and stirred at 27.5° C. for 25 min to obtain a pressure-reducing and injection-increasing surfactant.
对比例1Comparative Example 1
（1）将5重量份的金刚烷改性纳米二氧化硅、2.5重量份的十二烷基二苯醚双磺酸钠、2重量份的甲基戊醇、1.5重量份的三甲基硅烷基葡萄糖苷、3.5重量份的水加入到反应釜中，在27.5℃下搅拌25min，得到降压增注表面活性剂。(1) Add 5 parts by weight of adamantane-modified nano-silica, 2.5 parts by weight of sodium dodecyl diphenyl ether disulfonate, 2 parts by weight of methyl amyl alcohol, 1.5 parts by weight of trimethylsilyl glucoside, and 3.5 parts by weight of water into a reactor, and stir at 27.5° C. for 25 minutes to obtain a pressure-reducing and injection-increasing surfactant.
对比例2Comparative Example 2
（1）将4.5重量份的季铵化碳纳米管、2.5重量份的十二烷基二苯醚双磺酸钠、2重量份的甲基戊醇、1.5重量份的三甲基硅烷基葡萄糖苷、3.5重量份的水加入到反应釜中，在27.5℃下搅拌25min，得到降压增注表面活性剂。(1) 4.5 parts by weight of quaternized carbon nanotubes, 2.5 parts by weight of sodium dodecyl diphenyl ether disulfonate, 2 parts by weight of methyl amyl alcohol, 1.5 parts by weight of trimethylsilyl glucoside, and 3.5 parts by weight of water were added to a reactor and stirred at 27.5° C. for 25 minutes to obtain a pressure-reducing and injection-increasing surfactant.
取本发明实施例1-3和对比例1-2制备的降压增注表面活性剂，采用矿化度为55000mg/L的油田用水配制成0.08wt%的降压增注表面活性剂溶液。采用表面张力仪测定降压增注表面活性剂的表面张力以及降低油水界面张力的能力（实验用油采用胜利油田脱水原油）。降压率的测定依照Q/SLCG0026-2013《降压增注表面活性剂技术要求》进行测定，测试液体为0.08wt%的降压增注表面活性剂。The depressurization and injection surfactant prepared in Examples 1-3 and Comparative Examples 1-2 of the present invention was used to prepare a 0.08wt% depressurization and injection surfactant solution using oilfield water with a salinity of 55000mg/L. A surface tension meter was used to measure the surface tension of the depressurization and injection surfactant and its ability to reduce the oil-water interfacial tension (the experimental oil used dehydrated crude oil from Shengli Oilfield). The depressurization rate was determined in accordance with Q/SLCG0026-2013 "Technical Requirements for Depressurization and Injection Surfactants", and the test liquid was 0.08wt% of the depressurization and injection surfactant.
表1：降压表面活性剂性能测试。Table 1: Pressure reducing surfactant performance test.
由表1可知，实施例1-3制备的降压增注表面活性剂的性能，比对比例1-2好。As can be seen from Table 1, the performance of the pressure-reducing and injection-increasing surfactants prepared in Examples 1-3 is better than that in Comparative Examples 1-2.
以上公开的本发明优选实施例只是用于帮助阐述本发明。优选实施例并没有详尽叙述所有的细节，也不限制该发明仅为所述的具体实施方式。显然，根据本说明书的内容，可作很多的修改和变化。本说明书选取并具体描述这些实施例，是为了更好地解释本发明的原理和实际应用，从而使所属技术领域技术人员能很好地理解和利用本发明。本发明仅受权利要求书及其全部范围和等效物的限制。The preferred embodiments of the present invention disclosed above are only used to help illustrate the present invention. The preferred embodiments do not describe all the details in detail, nor do they limit the invention to the specific implementation methods described. Obviously, many modifications and changes can be made according to the content of this specification. This specification selects and specifically describes these embodiments in order to better explain the principles and practical applications of the present invention, so that those skilled in the art can understand and use the present invention well. The present invention is limited only by the claims and their full scope and equivalents.
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| CN101517487A (en) * | 2006-09-25 | 2009-08-26 | 日立化成工业株式会社 | Radiation-sensitive composition, method of forming silica-based coating film, silica-based coating film, apparatus and member having silica-based coating film and photosensitizing agent for insulating |
| CN106118198A (en) * | 2016-07-06 | 2016-11-16 | 西南交通大学 | The preparation method of carbon nano tube surface quaternized antibacterial in situ |
| CN115895631A (en) * | 2021-08-26 | 2023-04-04 | 中国石油化工股份有限公司 | Pressure-reducing injection-increasing surfactant composition and preparation method and application thereof |
| CN116790241A (en) * | 2023-02-09 | 2023-09-22 | 西南石油大学 | A honeycomb liquid raw material composition and its preparation method and application |
| CN117070205A (en) * | 2023-10-12 | 2023-11-17 | 胜利油田海发环保化工有限责任公司 | Pressure-reducing injection-increasing surfactant and preparation method thereof |
| CN118406290A (en) * | 2024-05-17 | 2024-07-30 | 深圳市金百纳纳米科技有限公司 | Modified carbon nano tube and preparation method and application thereof |
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| CN101517487A (en) * | 2006-09-25 | 2009-08-26 | 日立化成工业株式会社 | Radiation-sensitive composition, method of forming silica-based coating film, silica-based coating film, apparatus and member having silica-based coating film and photosensitizing agent for insulating |
| CN106118198A (en) * | 2016-07-06 | 2016-11-16 | 西南交通大学 | The preparation method of carbon nano tube surface quaternized antibacterial in situ |
| CN115895631A (en) * | 2021-08-26 | 2023-04-04 | 中国石油化工股份有限公司 | Pressure-reducing injection-increasing surfactant composition and preparation method and application thereof |
| CN116790241A (en) * | 2023-02-09 | 2023-09-22 | 西南石油大学 | A honeycomb liquid raw material composition and its preparation method and application |
| CN117070205A (en) * | 2023-10-12 | 2023-11-17 | 胜利油田海发环保化工有限责任公司 | Pressure-reducing injection-increasing surfactant and preparation method thereof |
| CN118406290A (en) * | 2024-05-17 | 2024-07-30 | 深圳市金百纳纳米科技有限公司 | Modified carbon nano tube and preparation method and application thereof |
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