CN105924594B - A kind of preparation method of fluorine-containing dissaving polymer oil displacement agent - Google Patents
A kind of preparation method of fluorine-containing dissaving polymer oil displacement agent Download PDFInfo
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Abstract
The invention discloses a kind of preparation methods of fluorine-containing dissaving polymer oil displacement agent.This method comprises the following steps：(1) under an inert atmosphere, the hyperbranched polyglycidyl ether of end group hydroxyl is reacted with redox initiator, obtains reaction solution 1；(2) acrylamide monomer, sodium acrylate monomers, fluorine-containing hydrophobic monomer, both sexes multijaw type hydrophobic function monomer are slowly added to successively into the reaction solution 1 and carries out graft copolymerization to get the polymer；The structural formula of the fluorine-containing dissaving polymer oil displacement agent is as shown in formula I.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 can be obtained by adjusting each monomer additive amount, and resulting polymers have preferable thickening and anti-shear performance, have oil gas field application prospect.
Description
Technical field
The present invention relates to a kind of preparation methods of fluorine-containing dissaving polymer oil displacement agent, belong to polymeric material field.
Background technology
As polyacrylamide is in the application in putting into practice of recovering the oil, migrated on injection allocation, pit shaft, near wellbore zone and stratum
The main reason for serious problem is gradually exposed, causes polymer degradation of degrading in journey include 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 70% or more.Molecular modification is carried out to improve the anti-shear performance of polymer for polymer to polymer
Technology of reservoir sweep is of great significance.
Invention content
It is provided by the invention to contain the object of the present invention is to provide a kind of preparation method of fluorine-containing dissaving polymer oil displacement agent
Fluorine dissaving polymer oil displacement agent has higher viscosity and stronger anti-shear performance.
The preparation method of fluorine-containing dissaving polymer provided by the present invention, includes the following steps：
(1) under an inert atmosphere, the hyperbranched polyglycidyl ether of end group hydroxyl carries out anti-with redox initiator
It answers, obtains reaction solution 1；
(2) be slowly added to successively into the reaction solution 1 acrylamide monomer, sodium acrylate monomers, fluorine-containing hydrophobic monomer,
Both sexes multijaw type hydrophobic function monomer carries out graft copolymerization to get the polymer；
The structural formula of the fluorine-containing dissaving polymer is as shown in formula I：
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, gathers fluorine-containing hydrophobic segment and poly- both sexes multijaw at Sodium Polyacrylate segment
Type hydrophobic function segment is sequentially connected, and the other end of the polyacrylamide segment is grafted on the core A.
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 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.
The fluorine-containing hydrophobic monomer is hexafluorobutyl acrylate, Hexafluorobutyl mathacrylate, ten trifluoro of methacrylic acid
At least one of monooctyl ester, dodecafluorhe-ptylacrylate, dodecafluoroheptyl methacrylate and trifluoroethyl methacrylate；
The both sexes multijaw type hydrophobic function monomer is acrylic acid bromo shown in acrylic acid glycine betaine or formula III shown in formula II
Quaternary ammonium salt：
In formula II, n is the number between 1~8；
In formula III, p is the number between 11~17.
In above-mentioned preparation method, the molecular formula of the hyperbranched polyglycidyl ether of the end group hydroxyl 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 total initiation system to obtain the final product；
It is described to cause the mixture that system is 1,1,1- trimethylolpropanes and potassium methoxide altogether.
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, and the time can be 10~15 hours, such as in 95 DEG C of condition
Lower reaction 15 hours.
In above-mentioned preparation method, in step (1), the redox initiator can 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 being added, 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.
Fluorine-containing dissaving polymer oil displacement agent prepared by the method for the present invention can be used as oil displacement agent for the field polymers displacement of reservoir oil
In, compound concentration ranging from 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, building-up process step
Rapid simple, condition normal temperature and pressure is easy to amplify, and series structure and composition polymer can be obtained by adjusting each monomer additive amount,
And resulting polymers have preferable thickening and anti-shear performance, have 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 implementation mode
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
At).After addition, a large amount of methanol is added in the reaction was continued 5h, and excessively cationic pillar removes K+, with a large amount 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：5.0mL is added
1, the 3- propane sultones containing 2.6mL are added dropwise in the acetone of monomer 2- (dimethylamino) ethylmethyl acrylate, 25.0mL
Acetone soln 10mL.After being added dropwise, 40 DEG C are warming up to, is stirred to react 10 hours, system generates a large amount of white solids, after cooling
Filtering, crude product are cleaned with the acetone of 20mL and remove unreacted monomer and sultones repeatedly, and last white solid is dry 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 is added
The bromo n-octadecane containing 9.9g is added dropwise in the acetone of 5.0mL monomers 2- (dimethylamino) ethylmethyl acrylate, 40.0mL
Acetone soln 10mL.After being added dropwise, 40 DEG C are warming up to, is stirred to react 10-20 hours several, a large amount of white solids of system generation,
Cooled and filtered, crude product are cleaned with the acetone of 100mL 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.
Dodecafluoroheptyl methacrylate employed in following embodiments is to avenge good fluorine chemistry of silicones Products, reagent contracting
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, 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 is placed in drying in 70 DEG C of baking ovens and goes moisture removal to get the fluorine-containing dissaving polymer oil displacement agents of 1#, and viscosity average molecular weigh is about 700
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, 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 is placed in drying in 70 DEG C of baking ovens and goes moisture removal to get the fluorine-containing dissaving polymer oil displacement agents of 2#, and viscosity average molecular weigh is about 700
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 1# and the fluorine-containing dissaving polymer oil displacement agents of 2# prepared to the present invention is 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, is purchased from SNF companies of France, and 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 relationship 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
When degree is 2000mg/L, 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, it is the polymer solution of 1500mg/L to take aimed concn, 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 is 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%, is higher than 40% or so of unaltered portion hydrolyzed polyacrylamide.
(3) Oil Displacing Capacity：It is the polymer solution of 1750mg/L, one grade of shearing 20s of Waring blenders to take aimed concn
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 98% or more 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% are can be improved than unaltered portion hydrolyzed polyacrylamide.
In conclusion dissaving polymer of the present invention be demonstrated by the thickening better than unaltered portion hydrolyzed polyacrylamide,
Salt resistance, anti-shearing and Oil Displacing Capacity, can be used as polymer oil-displacing agent.
Claims (1)
1. the preparation method of fluorine-containing dissaving polymer, includes the following steps：
(1) under an inert atmosphere, the hyperbranched polyglycidyl ether of end group hydroxyl is reacted with redox initiator, is obtained
To reaction solution 1；
Oxidant in the redox initiator is selected from following at least one：Ammonium ceric nitrate, 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 Initiator
The mass percent concentration of agent is 0.5%~3%；
The mass ratio of the redox initiator and the hyperbranched polyglycidyl ether of the end group hydroxyl is 1.5~3：1；
The temperature of the reaction is 30~50 DEG C, and the time is 30~60min；
(2) acrylamide monomer, sodium acrylate monomers, fluorine-containing hydrophobic monomer, both sexes are slowly added to successively into the reaction solution 1
Multijaw type hydrophobic function monomer carries out graft copolymerization to get the polymer；
The acrylamide monomer is added in the form of acrylamide monomer aqueous solution, the matter of the acrylamide monomer aqueous solution
It is 15~25% to measure percent concentration；
The sodium acrylate monomers are added in the form of sodium acrylate monomers aqueous solution, the matter of the sodium acrylate monomers aqueous solution
It is 15~25% to measure percent concentration；
The fluorine-containing hydrophobic monomer is added in the form of emulsion, and the emulsion is matched using lauryl sodium sulfate and water
It makes, in the emulsion, the mass percent concentration of the fluorine-containing hydrophobic monomer is 2~10%；
The both sexes multijaw type hydrophobic function monomer is added in the form of both sexes multijaw type hydrophobic function monomer solution, and described two
Property multijaw type hydrophobic function monomer solution mass concentration can be 2~10%；
It is the hyperbranched polyglycidyl ether of the end group hydroxyl, the acrylamide monomer, the sodium acrylate monomers, described
The mass ratio of fluorine-containing hydrophobic monomer and the both sexes multijaw type hydrophobic function monomer is 1：220~320：70~90：6~18：5~
20；
The temperature of the graft copolymerization is 45~75 DEG C, and the time is 5~10h；
The structural formula of the fluorine-containing dissaving polymer 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 total initiation system to obtain the final product；
It is described to cause the mixture that system is 1,1,1- trimethylolpropanes and potassium methoxide altogether；
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, and the time is 10~15 hours；
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 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；
The fluorine-containing hydrophobic monomer be 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 or formula III shown in formula II
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.
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