CN106117456B - A kind of fluorine-containing dissaving polymer oil displacement agent - Google Patents
A kind of fluorine-containing dissaving polymer oil displacement agent Download PDFInfo
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Abstract
The invention discloses a kind of fluorine-containing dissaving polymer oil displacement agents.The structural formula of the fluorine-containing dissaving polymer oil displacement agent as shown in formula I, wherein, core A be end group hydroxyl hyperbranched polyglycidyl ether；Arm B is the copolymer formed by acrylamide, sodium acrylate, fluorine-containing hydrophobic monomer and both sexes multijaw type hydrophobic function monomer；In the copolymer, polyacrylamide segment, Sodium Polyacrylate segment, poly- fluorine-containing hydrophobic segment and poly- both sexes multijaw type hydrophobic function segment are sequentially connected, and the other end of the polyacrylamide segment is grafted on the core A.The preparation process of the fluorine-containing dissaving polymer oil displacement agent of the present invention is water phase free-radical emulsion polymerization, building-up process step is simple, condition normal temperature and pressure, it is easy to amplify, series structure and composition polymer are can obtain by adjusting each monomer additive amount, and resulting polymers have preferable thickening and anti-shear performance, possess oil gas field application prospect.
Description
Technical field
The present invention relates to a kind of fluorine-containing dissaving polymer oil displacement agents, belong to polymeric material field.
Background technology
With application of the polyacrylamide in practice of recovering the oil, migrated on injection allocation, pit shaft, near wellbore zone and stratum
The main reason for being gradually exposed, causing polymer degradation the problem of serious of degrading in journey, includes mechanical degradation, thermal degradation, micro-
Biodegradable and chemical degradation etc., and wherein most important is mechanical degradation.Polymer solution after mechanical pump high speed shear,
Viscosity declines up to more than 70%.Molecular modification is carried out to polymer to improve the anti-shear performance of polymer for polymer
Technology of reservoir sweep is of great significance.
The content of the invention
The object of the present invention is to provide a kind of fluorine-containing dissaving polymer oil displacement agent, fluorine-containing hyperbranched polies provided by the invention
Closing object oil displacement agent has higher viscosity and stronger anti-shear performance.
Fluorine-containing dissaving polymer provided by the present invention, structural formula is as shown in formula I：
Core A：● arm B：
Wherein, core A is the hyperbranched polyglycidyl ether of end group hydroxyl；
Arm B is to be total to by what acrylamide, sodium acrylate, fluorine-containing hydrophobic monomer and both sexes multijaw type hydrophobic function monomer were formed
Polymers；
In the copolymer, polyacrylamide segment, Sodium Polyacrylate segment gather fluorine-containing hydrophobic segment and poly- both sexes multijaw
Type hydrophobic function segment is sequentially connected, and the other end of the polyacrylamide segment is grafted on the core A.
In above-mentioned fluorine-containing dissaving polymer oil displacement agent, point of the hyperbranched polyglycidyl ether of the end group hydroxyl
Minor is (C3H8O3)m, wherein m is the integer between 7~12, if m is 9；
The branch rate of the hyperbranched polyglycidyl ether of the end group hydroxyl can be 0.5~0.6, concretely 0.6.
The hyperbranched polyglycidyl ether of the end group hydroxyl is prepared according to the method included the following steps：
Glycidol carries out ring-opening polymerization under conditions of common initiation system to obtain the final product；
It is described to trigger system altogether as 1,1,1- trimethylolpropanes and the mixture of potassium methoxide；
The mass ratio of the 1,1,1- trimethylolpropanes, the potassium methoxide and the glycidol can be 1：0.11~
0.13：130~170, concretely 1：0.12：169；
The temperature of the ring-opening polymerization can be 90~100 DEG C, when the time can be 10~15 small, such as in 95 DEG C of condition
It is lower reaction 15 it is small when.
In above-mentioned fluorine-containing dissaving polymer, the viscosity average molecular weigh of the fluorine-containing dissaving polymer oil displacement agent is 300
Ten thousand~8,000,000；
The core A, the polyacrylamide segment, the Sodium Polyacrylate segment, the poly- fluorine-containing hydrophobic segment and institute
The mass ratio for stating poly- both sexes multijaw type hydrophobic function segment can be 1：200~300：65~80：4~15：3~18, concretely
1：260：70：7.0~7.2：8.1~8.3,1：260：70：7.2：8.3 or 1：260：70：7.0：8.1.
In above-mentioned fluorine-containing dissaving polymer, the fluorine-containing hydrophobic monomer is hexafluorobutyl acrylate, methacrylic acid
Hexafluoro butyl ester, ten trifluoro monooctyl ester of methacrylic acid, dodecafluorhe-ptylacrylate, dodecafluoroheptyl methacrylate and metering system
At least one of sour trifluoro ethyl ester；
The both sexes multijaw type hydrophobic function monomer is acrylic acid bromo shown in acrylic acid glycine betaine shown in formula II or formula III
Quaternary ammonium salt：
In formula II, n is the number between 1~8；
In formula III, p is the number between 11~17.
The fluorine-containing dissaving polymer of the present invention can be prepared by a method comprising the following steps：
(1) under an inert atmosphere, the hyperbranched polyglycidyl ether of the end group hydroxyl and redox initiator into
Row reaction, obtains reaction solution 1；
(2) it is slowly added to the acrylamide monomer, sodium acrylate monomers, described successively into the reaction solution 1
Fluorine-containing hydrophobic monomer, the both sexes multijaw type hydrophobic function monomer carry out graft copolymerization to get the polymer.
In above-mentioned preparation method, in step (1), the redox initiator may be selected from following at least one：Nitric acid
Cerium ammonium, potassium peroxydisulfate, ammonium persulfate, sodium peroxydisulfate and hydrogen peroxide；
The redox initiator participates in reacting in the form of its aqueous solution, in the aqueous solution, the redox
The mass percent concentration of initiator can be 0.5%~3%, concretely 0.5%；
The mass ratio of the redox initiator and the hyperbranched polyglycidyl ether of the end group hydroxyl can be 1.5
~3：1, concretely 2：1；
The temperature of the reaction can be 30~50 DEG C, and the time can be 30~60min, such as react 30min at 40 DEG C.
In above-mentioned preparation method, in step (2), the acrylamide monomer is in the form of acrylamide monomer aqueous solution
It adding in, the mass percent concentration of the acrylamide monomer aqueous solution can be 15~25%, concretely 20%；
The sodium acrylate monomers are added in the form of sodium acrylate monomers aqueous solution, the sodium acrylate monomers aqueous solution
Mass percent concentration can be 15~25%, concretely 20%；
The fluorine-containing hydrophobic monomer is added in the form of emulsion, the emulsion using lauryl sodium sulfate and water into
Row is prepared, and in the emulsion, the mass percent concentration of the fluorine-containing hydrophobic monomer can be 2~10%, and concretely 5%；
The both sexes multijaw type hydrophobic function monomer is added in the form of both sexes multijaw type hydrophobic function monomer solution, institute
The mass concentration for stating both sexes multijaw type hydrophobic function monomer solution can be 2~10%, concretely 5%.
In above-mentioned preparation method, the hyperbranched polyglycidyl ether of the end group hydroxyl, the acrylamide monomer,
The mass ratio of the sodium acrylate monomers, the fluorine-containing hydrophobic monomer and the both sexes multijaw type hydrophobic function monomer can be 1：
220~320：70~90：6~18：5~20, concretely 1：280：80：8：10；
The temperature of the graft copolymerization can be 45~75 DEG C, and the time can be 5~10h, such as react 6h at 55 DEG C.
The method further includes the withering step of reaction system to step (2), such as at 60~80 DEG C (70
DEG C) baking oven in be dried.
The fluorine-containing dissaving polymer can be used in the field polymers displacement of reservoir oil, compound concentration scope for 1200~
3000mg/L, such as 1750mg/L.
The present invention has following beneficial aspects：
The preparation process of the fluorine-containing dissaving polymer oil displacement agent of the present invention is water phase free-radical emulsion polymerization, and building-up process walks
Rapid simple, condition normal temperature and pressure is easy to amplify, and series structure and composition polymer are can obtain by adjusting each monomer additive amount,
And resulting polymers have preferable thickening, anti-shearing and Oil Displacing Capacity, possess oil gas field application prospect.
Description of the drawings
Fig. 1 is the thickening property figure of fluorine-containing dissaving polymer oil displacement agent prepared by the present invention.
Fig. 2 is the anti-shear performance figure of fluorine-containing dissaving polymer oil displacement agent prepared by the present invention.
Fig. 3 is the HNMR nuclear-magnetism figures of acrylic acid glycine betaine monomer.
Fig. 4 is the HNMR nuclear-magnetism figures of acrylic acid bromo quaternary ammonium salt monomer.
Specific embodiment
Experimental method used in following embodiments is conventional method unless otherwise specified.
The materials, reagents and the like used in the following examples is commercially available unless otherwise specified.
HPG employed in following embodiments is prepared as steps described below：
1,1,1- trimethylolpropane (TMP) (0.187g, 1.39mmol) is added in three-necked flask, is then added dropwise
The methanol solution (potassium methoxide containing 22mg) of 20% potassium methoxide of 0.11mL reacts 20min, methanol is removed in vacuum, adds anhydrous
Dioxane 20mL.Temperature rises to 95 DEG C, and being slowly added to very much the glycidol glycidol of 25mL (31.6g), (about 10h is complete
Into).After addition, the reaction was continued 5h adds in substantial amounts of methanol, and excessively cationic pillar removes K+, with substantial amounts of acetone precipitation
Methanol solution obtains white solid HPG, and suction filtration, vacuum freezedrying obtain product HPG (m=8~10), and molecular formula is (C3H8O3)m,
Wherein m is 9, and branch rate is 0.6.
Acrylic acid glycine betaine monomer (n=1) employed in following embodiments is prepared by the following method：Add in 5.0mL
Monomer 2- (dimethylamino) ethylmethyl acrylate, the acetone of 25.0mL, are added dropwise 1, the 3- propane sultones containing 2.6mL
Acetone soln 10mL.After being added dropwise, be warming up to 40 DEG C, be stirred to react 10 it is small when, system generates a large amount of white solids, after cooling
Filtering, crude product cleans the unreacted monomer of removing repeatedly with the acetone of 20mL and sultones, last white solid are done with vacuum
Dry to obtain product, HNMR nuclear-magnetism figures are as shown in Figure 3.
Acrylic acid bromo quaternary ammonium salt monomer (n=16) employed in following embodiments is prepared by the following method：It adds in
5.0mL monomers 2- (dimethylamino) ethylmethyl acrylate, the acetone of 40.0mL, are added dropwise the bromo n-octadecane containing 9.9g
Acetone soln 10mL.After being added dropwise, be warming up to 40 DEG C, be stirred to react several 10-20 it is small when, system generates a large amount of white solids,
Cooled and filtered, crude product with the acetone of 100mL are cleaned and remove unreacted monomer and bromo n-octadecane repeatedly, and last white is solid
For body with obtaining the product in a vacuum and drying environment, HNMR nuclear-magnetism figures are as shown in Figure 4.
To avenge good fluorine chemistry of silicones Products, reagent contracts dodecafluoroheptyl methacrylate employed in following embodiments
DFBMA is write, CAS registration numbers are 2261-99-6.
Embodiment 1 prepares fluorine-containing dissaving polymer oil displacement agent
By 25mg parent nucleus HPG, 85mL H2O is placed in three-necked flask, stirring and dissolving, is passed through nitrogen deoxygenation 45min, then
Ammonium ceric nitrate aqueous solution (50mg ammonium ceric nitrates are dissolved in 10mL water) is added under nitrogen protection, and 30min is stirred to react at 40 DEG C,
It is slowly added to acrylamide aqueous solution (7.0g acrylamides are dissolved in 28mL water), aqueous sodium acrylate solution successively into reaction solution
(2.0g sodium acrylate is dissolved in 8mL water), dodecafluoroheptyl methacrylate monomer emulsion (200mg methacrylic acids 12
Fluorine heptyl ester monomer is emulsifiable in 3.8mL water, and emulsifier is lauryl sodium sulfate 200mg), acrylic acid glycine betaine function monomer water
Solution (250mg acrylic acid glycine betaine function monomers are dissolved in 4.8mL water) is then warming up to 55 DEG C of reaction 6h, gained is reacted
Liquid, which is placed in 70 DEG C of baking ovens, dry to be removed moisture removal viscosity average molecular weigh is about 700 to get 1# fluorine-containing dissaving polymer oil displacement agents
Ten thousand.
In the fluorine-containing dissaving polymer oil displacement agents of 1# manufactured in the present embodiment, HPG, polyacrylamide segment, polyacrylic acid
The mass ratio of sodium segment, ten difluoro heptyl ester segment of polymethylacrylic acid and polyacrylic acid glycine betaine segment is 1：260：70：7.2：
8.3。
Embodiment 2 prepares fluorine-containing dissaving polymer oil displacement agent
By 25mg parent nucleus HPG, 85mL H2O is placed in three-necked flask, stirring and dissolving, is passed through nitrogen deoxygenation 45min, then
Ammonium ceric nitrate aqueous solution (60mg ammonium ceric nitrates are dissolved in 10mL water) is added under nitrogen protection, and 30min is stirred to react at 40 DEG C,
It is slowly added to acrylamide aqueous solution (7.0g acrylamides are dissolved in 28mL water), aqueous sodium acrylate solution successively into reaction solution
(2.0g sodium acrylate is dissolved in 8mL water), dodecafluoroheptyl methacrylate monomer emulsion (200mg methacrylic acids 12
Fluorine heptyl ester monomer is emulsifiable in 3.8mL water, and emulsifier is lauryl sodium sulfate 200mg), acrylic acid bromo quaternary ammonium salt monomer water
Solution (250mg acrylic acid bromo quaternary ammonium salt monomers are dissolved in 4.8mL water) is then warming up to 55 DEG C of reaction 6h, gained is reacted
Liquid, which is placed in 70 DEG C of baking ovens, dry to be removed moisture removal viscosity average molecular weigh is about 700 to get 2# fluorine-containing dissaving polymer oil displacement agents
Ten thousand.
In the fluorine-containing dissaving polymer oil displacement agents of 2# manufactured in the present embodiment, HPG, polyacrylamide segment, polyacrylic acid
The mass ratio of sodium segment, ten difluoro heptyl ester segment of polymethylacrylic acid and polyacrylic acid bromo quaternary ammonium salt segment is 1：260：70：
7.0：8.1.
The performance test of embodiment 3, fluorine-containing dissaving polymer oil displacement agent
The performance of the 1# for preparing of the present invention and the fluorine-containing dissaving polymer oil displacement agents of 2# are evaluated, evaluation method and
As a result as follows, wherein unaltered portion hydrolyzed polyacrylamide (i.e. " general polymer ") is industrialization product, and marque is
FP6050, purchased from French SNF companies, structure is linear straight chain type.
(1) thickening property takes a certain amount of polymer, and under 45 DEG C of water bath conditions, various concentration is prepared with deionized water
Polymer solution, the relation of test polymer viscosity and concentration evaluates the thickening property of polymer, and the results are shown in Figure 1, and
It is compared with unaltered portion hydrolyzed polyacrylamide performance.
As shown in Figure 1, with the increase of concentration, the viscosity of 1# and 2# dissaving polymer aqueous solutions dramatically increases, when dense
Spend for 2000mg/L when, 1# and 2# dissaving polymer solution viscosities may be up to 100 and 103mPas, far above unmodified
The 65.8mPas of partially hydrolyzed polyacrylamide (PHPA).
(2) anti-shear performance takes the polymer solution that aimed concn is 1500mg/L, with the 1 grade of shearing of Rhein blender
20s measures its apparent viscosity under different salinities before and after polymeric shear, viscosity retention ratio is calculated, as a result such as Fig. 2 institutes
Show, and compared with unaltered portion hydrolyzed polyacrylamide performance.
As shown in Figure 2, in concentrated water, after 1# and 2# dissaving polymer solution are clipped, viscosity retention ratio is protected
It holds between 52%~58%, higher than 40% or so of unaltered portion hydrolyzed polyacrylamide.
(3) Oil Displacing Capacity：Take the polymer solution that aimed concn is 1750mg/L, one grade of shearing 20s of Waring blenders
It is spare afterwards.Use for laboratory artificial core, gas permeability are respectively 500,2000 and 4000mD from top to bottom.With Bohai Sea oil field
Simulation oil is compounded after comprehensive oil sample dehydration with kerosene, 65 DEG C of viscosity are 70mPas.First carry out water drive, it is aqueous up to more than 98% when
Turn polymer flooding.Polymer and water drive velocity are 3m/d, and polymer solution injected slurry volume is 0.3PV.The experimental results showed that 1#
With the oil-recovering rate of 2# dissaving polymer solution 12~16% can be improved than unaltered portion hydrolyzed polyacrylamide.
In conclusion dissaving polymer of the present invention be demonstrated by better than unaltered portion hydrolyzed polyacrylamide thickening,
Salt resistance, anti-shearing and Oil Displacing Capacity, can be used as polymer oil-displacing agent.
Claims (1)
1. a kind of fluorine-containing dissaving polymer, structural formula is as shown in formula I：
Wherein, core A is the hyperbranched polyglycidyl ether of end group hydroxyl；
The molecular formula of the hyperbranched polyglycidyl ether of the end group hydroxyl is (C3H8O3)m, wherein m be 7~12 between it is whole
Number；
The branch rate of the hyperbranched polyglycidyl ether of the end group hydroxyl is 0.5~0.6；
The hyperbranched polyglycidyl ether of the end group hydroxyl is prepared according to the method included the following steps：
Glycidol carries out ring-opening polymerization under conditions of common initiation system to obtain the final product；
It is described to trigger system altogether as 1,1,1- trimethylolpropanes and the mixture of potassium methoxide；
The mass ratio of the 1,1,1- trimethylolpropanes, the potassium methoxide and the glycidol is 1：0.11~0.13：130
~160；
The temperature of the ring-opening polymerization is 90~100 DEG C, when the time is 10~15 small；
Arm B is the copolymerization formed by acrylamide, sodium acrylate, fluorine-containing hydrophobic monomer and both sexes multijaw type hydrophobic function monomer
Object；
In the copolymer, polyacrylamide segment, Sodium Polyacrylate segment, poly- fluorine-containing hydrophobic segment and poly- both sexes multijaw type are dredged
Water function segment is sequentially connected, and the other end of the polyacrylamide segment is grafted on the core A；
The fluorine-containing hydrophobic monomer for hexafluorobutyl acrylate, Hexafluorobutyl mathacrylate, ten trifluoro monooctyl ester of methacrylic acid,
At least one of dodecafluorhe-ptylacrylate, dodecafluoroheptyl methacrylate and trifluoroethyl methacrylate；
The both sexes multijaw type hydrophobic function monomer is acrylic acid bromo quaternary ammonium shown in acrylic acid glycine betaine shown in formula II or formula III
Salt：
In formula II, n is the number between 1~8；
In formula III, p is the number between 11~17；
The viscosity average molecular weigh of the fluorine-containing dissaving polymer oil displacement agent is 3,000,000~8,000,000；
The core A, the polyacrylamide segment, the Sodium Polyacrylate segment, the fluorine-containing hydrophobic segment and described poly- of gathering
The mass ratio of both sexes multijaw type hydrophobic function segment is 1：200~300：65~80：4~15：3~18.
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| CN109384937B (en) * | 2018-09-30 | 2022-04-05 | 广州医科大学 | Dihydro porphin modified hyperbranched polyglycidyl ether derivative and preparation method and application thereof |
| CN111019405B (en) * | 2019-11-11 | 2021-05-14 | 郑州轻工业学院 | Preparation method of amphiphilic hyperbranched molecule modified nano fluid |
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| EP2604636A1 (en) * | 2011-12-15 | 2013-06-19 | Stichting Dutch Polymer Institute | Enhanced oil recovery using polyacrylamides |
| CN104844765A (en) * | 2015-05-18 | 2015-08-19 | 中国海洋石油总公司 | Hyperbranched polymer oil-displacing agent and preparation method thereof |
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