CN103865507A - Preparation method and application of micro-molecular anti-swelling shrinkage agent - Google Patents

Preparation method and application of micro-molecular anti-swelling shrinkage agent Download PDF

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Publication number
CN103865507A
CN103865507A CN201410067571.7A CN201410067571A CN103865507A CN 103865507 A CN103865507 A CN 103865507A CN 201410067571 A CN201410067571 A CN 201410067571A CN 103865507 A CN103865507 A CN 103865507A
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mixture
amine
swollen
solvent
carboxylic acid
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陈刚
张洁
蔡丹
张黎
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Xian Shiyou University
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Xian Shiyou University
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/60Compositions for stimulating production by acting on the underground formation
    • C09K8/607Compositions for stimulating production by acting on the underground formation specially adapted for clay formations
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/60Compositions for stimulating production by acting on the underground formation
    • C09K8/62Compositions for forming crevices or fractures
    • C09K8/66Compositions based on water or polar solvents
    • C09K8/68Compositions based on water or polar solvents containing organic compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2208/00Aspects relating to compositions of drilling or well treatment fluids
    • C09K2208/12Swell inhibition, i.e. using additives to drilling or well treatment fluids for inhibiting clay or shale swelling or disintegrating

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a preparation method and application of a micro-molecular anti-swelling shrinkage agent. The preparation method of the micro-molecular anti-swelling shrinkage agent comprises the steps of dissolving amine into a solvent in a reaction kettle, uniformly stirring, adding carboxylic acid into the solution while stirring to obtain a mixture, heating the mixture until the mixture is completely dissolved, steaming the solvent in the mixture, and cooling to room temperature; transferring the mixture into a mortar, adding potassium chloride, and uniformly grinding the mixture and added potassium chloride to obtain the micro-molecular anti-swelling shrinkage agent. During application, the dosage of the micro-molecular anti-swelling shrinkage agent takes 0.1-2.0% of the mass of oil field working liquid; the anti-swelling rate of the micro-molecular anti-swelling shrinkage agent to clay is 50-80%; the swelling shrinkage ratio of the micro-molecular anti-swelling shrinkage agent is more than 20%. The micro-molecular anti-swelling shrinkage agent disclosed by the invention is small in molecular weight, good in inhibition performance and environment-friendly.

Description

The preparation and application that the anti-swollen contracting of a kind of small molecules is swollen dose
Technical field
The present invention relates to anti-swollen dose of preparing technical field of swollen contracting, be specifically related to the preparation and application of swollen dose of the anti-swollen contracting of a kind of small molecules.
Background technology
The main component of mud shale is clay mineral, layer mineral---the montmorillonite that wherein the superfine hydrous alumino silicates of particle forms, in its structure, reactive force is between layers weak Van der Waals force, with water base oilfield working fluids interaction process in easily water-swelling.The Complicated Fault Block Oilfield of low permeability and high pressure, clay mineral content is high, meets water and easily expands, migrates, and causes permeability plugging, and water injection pressure rises, and oil recovery ratio declines.The injuries that adopt the method for water filling initial stage interpolation clay stabilizer to slow down clay class mineral pair reservoir in the actual production of oil field at present more.For the situation of hydration swelling of clay mineral, traditional clay stabilizer is that expansion-resisting agent is very little to the restitution of reservoir penetrating power.For this situation, mainly take at present acidification to dispel block measure to remove reservoir pollution, but conventional souring method has, treatment radius is little, validity period is short, acidizing fluid itself injures the defects such as large to oil reservoir.
Contract swollen dose and have the anti-swollen function of traditional clay stabilizer concurrently, can make the clay dehydration of hydration swelling contract swollen, recover the penetrating power of reservoir.The research that at present domestic relevant contracting is swollen dose is less, and basic is all relative molecular mass at 1000 ~ 100000 organic cationic polymer.But because its molecular weight is larger, on the one hand molecular weight is excessive has limited its application at low permeability oil field, can only be adsorbed on the other hand clay surface, for the strong clay of swelling property, the inhibition of polyamine class shale clay swelling inhibitor is unsatisfactory.In addition, part polyamine class shale clay swelling inhibitor also exist toxicity large, with the problems such as anionic treatments agent compatibleness is poor.
Summary of the invention
In order to overcome the shortcoming of prior art, the object of the present invention is to provide the preparation and application of swollen dose of the anti-swollen contracting of a kind of small molecules, small molecules prevents that the molecular weight of swollen dose of swollen contracting is little, rejection good, environmental friendliness.
In order to achieve the above object, the technical solution used in the present invention is:
The preparation that the anti-swollen contracting of small molecules is swollen dose, comprises the following steps:
The first step, in reactor, amine is dissolved in 5-30 solvent doubly, stir, described amine is thanomin, diethanolamine, trolamine, quadrol, diethylenetriamine, triethylene tetramine, tetraethylene pentamine, five ethene hexamines of technical grade and above purity thereof and composition thereof, and described solvent is water of technical grade and above purity methyl alcohol, ethanol or the above purity of tap water and composition thereof;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:1-5, described carboxylic acid is lactic acid, oxysuccinic acid, tartrate, citric acid, gluconic acid, L-glutamic acid of technical grade and above purity thereof and composition thereof;
The 3rd step, is heated to 30-100 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 5-0.5:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is the product of technical grade and above purity thereof.
When application, the 0.1-2.0% that the anti-swollen dose of consumption of swollen contracting of small molecules is oilfield working fluids quality, its anti-swollen rate to clay is 50-80%, the swollen rate that contracts is greater than 20%.
Advantage of the present invention: repair mud stone bioactive molecule and clay mineral (montmorillonite, illite) generation physical-chemical reaction behind swollen dose of injection stratum of the anti-swollen contracting of small molecules, make clay lattice modification, make not expand after its chance water; The clay lattice having expanded, by discharging water molecules after chemical reaction modification, lattice dwindles.Bioactive molecule enters calmly pore space widely, reduce surface tension, eliminate the water blocking damage of large particle water, clean stratum, and make clay material and the former stratum mineral mortise of these modifications by multipoint adsorption effect, meet water injury thereby removed clay mineral, water lock, the injury that water-sensitive expands, migration causes stratum, reach step-down augmented injection, recover effective permeability, improve the outstanding effect of oil and gas development.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described.
Embodiment 1
The preparation that the anti-swollen contracting of small molecules is swollen dose, comprises the following steps:
The first step is dissolved in amine in the solvent of 5 times in reactor, stirs, and described amine is technical grade diethanolamine, and described solvent is industrial grade benzenemethanol;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:1, described carboxylic acid is the lactic acid of technical grade and above purity thereof;
The 3rd step, is heated to 30 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 5:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is the product of technical grade and above purity thereof.
When application, the anti-swollen dose of consumption of swollen contracting of small molecules is 2.0% of oilfield working fluids quality, and its anti-swollen rate to clay is 68%, and the swollen rate that contracts is 21%.
Embodiment 2
The preparation that the anti-swollen contracting of small molecules is swollen dose, comprises the following steps:
The first step is dissolved in amine in the solvent of 8 times in reactor, stirs, and described amine is technical grade trolamine, and described solvent is chemical pure ethanol;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:1, described carboxylic acid is technical grade tartrate;
The 3rd step, is heated to 40 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 3:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is the product of technical grade and above purity thereof.
When application, the anti-swollen dose of consumption of swollen contracting of small molecules is 1.5% of oilfield working fluids quality, and its anti-swollen rate to clay is 59%, and the swollen rate that contracts is 26%.
Embodiment 3
The preparation that the anti-swollen contracting of small molecules is swollen dose, comprises the following steps:
The first step is dissolved in amine in the solvent of 15 times in reactor, stirs, and described amine is analytical pure diethylenetriamine, and described solvent is analytical pure methyl alcohol;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:3, described carboxylic acid is chemical pure citric acid;
The 3rd step, is heated to 55 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 1:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is technical grade product.
When application, the anti-swollen dose of consumption of swollen contracting of small molecules is 0.8% of oilfield working fluids quality, and its anti-swollen rate to clay is 76%, and the swollen rate that contracts is 25%.
Embodiment 4
The preparation that the anti-swollen contracting of small molecules is swollen dose, comprises the following steps:
The first step is dissolved in amine in the solvent of 20 times in reactor, stirs, and described amine is technical grade triethylene tetramine, and described solvent is tap water;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:4, described carboxylic acid is industrial glucose acid;
The 3rd step, is heated to 60 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 0.5:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is technical grade product.
When application, the anti-swollen dose of consumption of swollen contracting of small molecules is 0.5% of oilfield working fluids quality, and its anti-swollen rate to clay is 76%, and the swollen rate that contracts is 33%.
Embodiment 5
The preparation that the anti-swollen contracting of small molecules is swollen dose, comprises the following steps:
The first step is dissolved in amine in the solvent of 30 times in reactor, stir, described amine be amount of substance than technical grade trolamine and tetraethylene pentamine mixture for 1:1, described solvent is that volume ratio is the industrial grade benzenemethanol of 1:1 and the mixture of tap water;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:1, described carboxylic acid is technical grade citric acid;
The 3rd step, is heated to 50 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 0.5:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is technical grade product.
When application, the anti-swollen dose of consumption of swollen contracting of small molecules is 0.5% of oilfield working fluids quality, and its anti-swollen rate to clay is 61%, and the swollen rate that contracts is 32%.
Embodiment 6
The preparation that the anti-swollen contracting of small molecules is swollen dose, comprises the following steps:
The first step is dissolved in amine in the solvent of 10 times in reactor, stirs, and described amine is chemical pure quadrol, and described solvent is that volume ratio is the industrial grade benzenemethanol of 1:3 and the mixture of tap water;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:2, described carboxylic acid is that amount of substance is than technical grade lactic acid and L-glutamic acid mixture for 1:1;
The 3rd step, is heated to 40 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 1.5:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is technical grade product.
When application, the anti-swollen dose of consumption of swollen contracting of small molecules is 0.3% of oilfield working fluids quality, and its anti-swollen rate to clay is 80%, and the swollen rate that contracts is 21%.

Claims (8)

1. small molecules is prevented a preparation for swollen dose of swollen contracting, it is characterized in that, comprises the following steps:
The first step, in reactor, amine is dissolved in 5-30 solvent doubly, stir, described amine is thanomin, diethanolamine, trolamine, quadrol, diethylenetriamine, triethylene tetramine, tetraethylene pentamine, five ethene hexamines of technical grade and above purity thereof and composition thereof, and described solvent is water of technical grade and above purity methyl alcohol, ethanol or the above purity of tap water and composition thereof;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:1-5, described carboxylic acid is lactic acid, oxysuccinic acid, tartrate, citric acid, gluconic acid, L-glutamic acid of technical grade and above purity thereof and composition thereof;
The 3rd step, is heated to 30-100 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 5-0.5:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is the product of technical grade and above purity thereof.
2. a kind of small molecules according to claim 1 is prevented the preparation of swollen dose of swollen contracting, it is characterized in that: when application, and the 0.1-2.0% that the anti-swollen dose of consumption of swollen contracting of small molecules is oilfield working fluids quality, its anti-swollen rate to clay is 50-80%, the swollen rate that contracts is greater than 20%.
3. a kind of small molecules according to claim 1 is prevented the preparation of swollen dose of swollen contracting, it is characterized in that, comprises the following steps:
The first step is dissolved in amine in the solvent of 5 times in reactor, stirs, and described amine is technical grade diethanolamine, and described solvent is industrial grade benzenemethanol;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:1, described carboxylic acid is the lactic acid of technical grade and above purity thereof;
The 3rd step, is heated to 30 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 5:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is the product of technical grade and above purity thereof.
4. a kind of small molecules according to claim 1 is prevented the preparation of swollen dose of swollen contracting, it is characterized in that, comprises the following steps:
The first step is dissolved in amine in the solvent of 8 times in reactor, stirs, and described amine is technical grade trolamine, and described solvent is chemical pure ethanol;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:1, described carboxylic acid is technical grade tartrate;
The 3rd step, is heated to 40 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 3:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is the product of technical grade and above purity thereof.
5. a kind of small molecules according to claim 1 is prevented the preparation of swollen dose of swollen contracting, it is characterized in that, comprises the following steps:
The first step is dissolved in amine in the solvent of 15 times in reactor, stirs, and described amine is analytical pure diethylenetriamine, and described solvent is analytical pure methyl alcohol;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:3, described carboxylic acid is chemical pure citric acid;
The 3rd step, is heated to 55 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 1:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is technical grade product.
6. a kind of small molecules according to claim 1 is prevented the preparation of swollen dose of swollen contracting, it is characterized in that, comprises the following steps:
The first step is dissolved in amine in the solvent of 20 times in reactor, stirs, and described amine is technical grade triethylene tetramine, and described solvent is tap water;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:4, described carboxylic acid is industrial glucose acid;
The 3rd step, is heated to 60 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 0.5:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is technical grade product.
7. a kind of small molecules according to claim 1 is prevented the preparation of swollen dose of swollen contracting, it is characterized in that, comprises the following steps:
The first step is dissolved in amine in the solvent of 30 times in reactor, stir, described amine be amount of substance than technical grade trolamine and tetraethylene pentamine mixture for 1:1, described solvent is that volume ratio is the industrial grade benzenemethanol of 1:1 and the mixture of tap water;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:1, described carboxylic acid is technical grade citric acid;
The 3rd step, is heated to 50 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 0.5:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is technical grade product.
8. a kind of small molecules according to claim 1 is prevented the preparation of swollen dose of swollen contracting, it is characterized in that, comprises the following steps:
The first step is dissolved in amine in the solvent of 10 times in reactor, stirs, and described amine is chemical pure quadrol, and described solvent is that volume ratio is the industrial grade benzenemethanol of 1:3 and the mixture of tap water;
Second step, under stirring to add in above-mentioned solution with amine in the amido functional group ratio carboxylic acid that is 1:2, described carboxylic acid is that amount of substance is than technical grade lactic acid and L-glutamic acid mixture for 1:1;
The 3rd step, is heated to 40 DEG C by said mixture, all dissolves to it;
The 4th step, boils off solvent in said mixture, is cooled to room temperature;
The 5th step, is transferred to said mixture in mortar, and the Repone K that to add with amine and carboxylic acid total mass ratio be 1.5:1 grinds evenly, obtains swollen dose of the anti-swollen contracting of small molecules, and described Repone K is technical grade product.
CN201410067571.7A 2014-02-27 2014-02-27 Preparation method and application of micro-molecular anti-swelling shrinkage agent Pending CN103865507A (en)

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Cited By (11)

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CN105219360A (en) * 2015-10-20 2016-01-06 中国石油集团渤海钻探工程有限公司 Bore completion water-soluble high-density weighting material and preparation method thereof
CN105219361A (en) * 2015-10-20 2016-01-06 中国石油集团渤海钻探工程有限公司 Water-soluble high-density weighting material and preparation method thereof
CN105219357A (en) * 2015-10-20 2016-01-06 中国石油集团渤海钻探工程有限公司 Oilfield drilling completion water-soluble high-density weighting material and preparation method thereof
CN105670574A (en) * 2014-11-21 2016-06-15 中石化胜利石油工程有限公司钻井工艺研究院 Drilling fluid ether-amine compound inhibitor and preparation method thereof
CN107434971A (en) * 2016-05-27 2017-12-05 中国石油天然气股份有限公司 A kind of water injection well Swelling-resistant shrinking and swelling agent and its preparation method and application
CN108715755A (en) * 2018-06-27 2018-10-30 长江大学 A kind of Swelling-resistant shrinking and swelling agent and preparation method thereof
CN109694697A (en) * 2017-10-23 2019-04-30 中石化石油工程技术服务有限公司 A kind of drilling fluid polyamine shale inhibitor and preparation method thereof and drilling fluid
CN112443301A (en) * 2020-12-02 2021-03-05 西安石油大油气科技有限公司 Method for improving crude oil recovery ratio by integrating oil displacement and pressure reduction
CN114479804A (en) * 2020-11-11 2022-05-13 中国石油天然气股份有限公司 Blocking remover and preparation method and application thereof
CN115838590A (en) * 2021-09-18 2023-03-24 中国石油化工股份有限公司 Low-cost high-efficiency anti-swelling agent for fracturing and preparation method and use method thereof
CN116376528A (en) * 2023-03-30 2023-07-04 天津新翔油气技术有限公司 Anti-swelling shrinkage sand-inhibiting agent, preparation method and application thereof

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Cited By (11)

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Publication number Priority date Publication date Assignee Title
CN105670574A (en) * 2014-11-21 2016-06-15 中石化胜利石油工程有限公司钻井工艺研究院 Drilling fluid ether-amine compound inhibitor and preparation method thereof
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CN105219361A (en) * 2015-10-20 2016-01-06 中国石油集团渤海钻探工程有限公司 Water-soluble high-density weighting material and preparation method thereof
CN105219357A (en) * 2015-10-20 2016-01-06 中国石油集团渤海钻探工程有限公司 Oilfield drilling completion water-soluble high-density weighting material and preparation method thereof
CN107434971A (en) * 2016-05-27 2017-12-05 中国石油天然气股份有限公司 A kind of water injection well Swelling-resistant shrinking and swelling agent and its preparation method and application
CN109694697A (en) * 2017-10-23 2019-04-30 中石化石油工程技术服务有限公司 A kind of drilling fluid polyamine shale inhibitor and preparation method thereof and drilling fluid
CN108715755A (en) * 2018-06-27 2018-10-30 长江大学 A kind of Swelling-resistant shrinking and swelling agent and preparation method thereof
CN114479804A (en) * 2020-11-11 2022-05-13 中国石油天然气股份有限公司 Blocking remover and preparation method and application thereof
CN112443301A (en) * 2020-12-02 2021-03-05 西安石油大油气科技有限公司 Method for improving crude oil recovery ratio by integrating oil displacement and pressure reduction
CN115838590A (en) * 2021-09-18 2023-03-24 中国石油化工股份有限公司 Low-cost high-efficiency anti-swelling agent for fracturing and preparation method and use method thereof
CN116376528A (en) * 2023-03-30 2023-07-04 天津新翔油气技术有限公司 Anti-swelling shrinkage sand-inhibiting agent, preparation method and application thereof

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Application publication date: 20140618