CN108865086A - A kind of high inhibition, strong rubber knot borehole wall stabilizer and preparation method thereof - Google Patents
A kind of high inhibition, strong rubber knot borehole wall stabilizer and preparation method thereof Download PDFInfo
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- CN108865086A CN108865086A CN201810400752.5A CN201810400752A CN108865086A CN 108865086 A CN108865086 A CN 108865086A CN 201810400752 A CN201810400752 A CN 201810400752A CN 108865086 A CN108865086 A CN 108865086A
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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
- C09K8/02—Well-drilling compositions
- C09K8/04—Aqueous well-drilling compositions
- C09K8/14—Clay-containing compositions
- C09K8/18—Clay-containing compositions characterised by the organic compounds
- C09K8/22—Synthetic organic compounds
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
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Abstract
The present invention relates to a kind of high inhibitions, strong rubber knot borehole wall stabilizer and preparation method thereof.Its technical solution is：High inhibition, the polyethyleneimine amine structure that strong rubber knot borehole wall stabilizer contains the branching as main chain and the catechol group being grafted on main chain.Beneficial effect is：The present invention has preferable wellbore stability effect, preparation process is easy to control, easy to operate, stable product quality, it is that the water base drilling fluid system that crucial inorganic agent is constituted has preferable rheological characteristic, inhibition, anti-collapse property by it using having preferable function and effect under the conditions of 150 DEG C；It can either the expansion of potent inhibition shale hydration, consolidated rock can be blocked simultaneously, improve mud shale mechanical property, enhance the additive for drilling fluid of borehole wall bearing capacity, water-base drilling fluid can be effectively pushed to replace oil base drilling fluid, wellbore stability is more efficiently kept, has great theoretical and practical significance.
Description
Technical field
It is the present invention relates to drilling fluid borehole wall stabilizer in a kind of Process of Oil Well Drilling, in particular to a kind of high inhibition, strong
Cementing borehole wall stabilizer and preparation method thereof.
Background technique
Continuous expansion with country to petroleum resources demand, deep-well, ultradeep well and shale gas under complex stratum condition
Well quantity is continuously increased, and the performance of drilling fluid allows for meeting more harsh requirement.Wherein, borehole wall stability problem one
It is directly a global problem in drilling process, the undergrounds such as well slough, undergauge bit freezing, bit balling caused by borehole well instability are multiple
Miscellaneous, accident causes a large amount of economic loss to petroleum industry every year.It is main both at home and abroad at present to use to solve wellbore stability problem
Oil base drilling fluid and high performance water-based drilling fluid system.Oil base drilling fluid although can effective stabilizing borehole, but exist at
This height, it is unfriendly, cementing quality is poor to environment the problems such as.A kind of current not water base drilling fluid system can completely inhibit viscous
The aquation of soil, thus can not effectively solve borehole well instability problem, and oil base drilling fluid cannot be replaced to meet complex geological condition and non-
The needs of conventional oil gas reservoir probing.
Studies have shown that mud shale borehole well instability is that " mechanics --- chemistry " multifactor multi- scenarios method effect is lower as a result, normal
Rule additive for drilling fluid often lays particular emphasis on chemical factor, i.e. chemical action between reduction drilling fluid and stratum, ignore mechanics because
Element and the synergistic effect between power, change, thus it is extremely difficult to the wellbore stability of real meaning.
According to " the materialization sealing borehole wall hinders slow pressure transmitting-reinforcement and aquation-chemical potential equilibrium of activation-rational density is inhibited to have
" polynary collaboration " wellbore stability of efficacy support " is theoretical, proposes a kind of drilling fluid well for having high inhibition, strong cementing power
Wall stabilizer.
Summary of the invention
The purpose of the present invention is to drawbacks described above of the existing technology, a kind of high inhibition, the strong rubber knot borehole wall are provided
Stabilizer and preparation method thereof while being able to maintain to mud shale high inhibition, improves the bearing capacity and glue-joint strength of the borehole wall,
Effectively keep wellbore stability.
A kind of high inhibition that the present invention mentions, strong rubber knot borehole wall stabilizer and preparation method thereof, technical solution is：Strong suppression
System, the polyethyleneimine amine structure that strong rubber knot borehole wall stabilizer contains the branching as main chain and the catechol being grafted on main chain
Group.
Preferably, above-mentioned high inhibition, strong rubber knot borehole wall stabilizer contain the structure as shown in formula (I)：
Formula (I)
In formula (I), in formula (I), R1 can be hydrogen, carbon atom number be 1-4 alkyl, phenyl ,-NH2,
, R2 can be hydrogen ,-NH2, carbon atom number be 1-4 alkyl, phenyl,, and R1 and
At least one is in R2, R3 is the alkyl that carbon atom number is 1-4, and l, m, n can
It is identical or different, respectively 1 or more integer.
The preparation method of a kind of high inhibition, strong rubber knot borehole wall stabilizer that the present invention mentions, technical solution are：Including following step
Suddenly：
(1) reaction vessel is added in catechol monomer (II) and ethyl alcohol, sufficiently dissolved, activator and methanol are pressed into quality 1:
0.8 ~ 2 mixing, is added reaction vessel, by catechol monomer activation 0.5-1h；
(2) polyethyleneimine of branching (III) is mixed with methanol, is added dropwise in activated mixture after completely dissolution,
Wherein the polyethyleneimine of branching, activated mixture are reaction monomers mixture A, and it is single that methanol usage can be completely dissolved reaction
Body mixture A；
(3) lead to nitrogen 10 minutes and catalyst is added under agitation, the initial temperature of reaction is 60-100 DEG C, and the reaction time is
Then 4-12h purifies products therefrom ether twice, be placed in deionized water and dialyse, be freeze-dried, obtain intermediate product；
(4) intermediate product in step (3) is dissolved in buffer solution, conserves certain time, keeps its full cross-linked；
(5) methanol in rotary evaporation removal step (4) suspension, is subsequently placed in bag filter with deionized water dialysis, vacuum
Freeze-drying finally obtains white or lavender solid product, contains structural unit shown in formula (VI) in product；
The polyethyleneimine of the branching：The mass ratio of the material of catechol monomer is 1：(1.3-3.3).
Preferably, above-mentioned activator is 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride (EDC), N-
One of HOSu NHS (NHS), 2- (N- morpholine) ethanesulfonic acid monohydrate (MES) are a variety of, activator and adjacent benzene
The ratio between amount of substance of diphenol monomer is 1:0.5-2.
Preferably, above-mentioned catalyst be one of formic acid, glacial acetic acid, propionic acid, hydrochloric acid, chloroform or a variety of, it is described
Catalyst is the 0.1% ~ 0.5% of reaction monomers mixture A gross mass.
Preferably, above-mentioned catechol group general formula such as (II)：
Formula (II)
In formula, R is the alkyl that carbon atom number is 1 ~ 4.
Preferably, such as (III), average weight-molecular mass can be 10000- to the polyethyleneimine general formula of above-mentioned branching
80000g/mol,
Formula (III)
In formula, l, m, n be may be the same or different, respectively 1 or more integer.
Preferably, above-mentioned catechol monomer can be the compound comprising formula (II), include but are not limited to adjacent benzene two
Phenolic group group be 3,4-Dihydroxybenzoic acid, 3,4-Dihydroxyphenylacetic acid, 3,4- dihydroxy benzenes propionic acid it is one or more.
Preferably, the buffer solution on can be molten for borate buffer solution, citrate buffer solution, phosphate-buffered
One of liquid, trihydroxy aminomethane buffer solution, the pH of buffer solution are 6-8.
Preferably, above-mentioned curing time is 4-48h.
The beneficial effects of the invention are as follows：The weight average molecular weight of high inhibition, strong rubber knot borehole wall stabilizer of the invention is
45000-80000g/mol, molecular weight is excessively high, and inorganic agent cannot go deep into inside mud shale gap, cannot be introduced into mud shale molecule
Interlayer thus limits its function and effect；The molecular weight no enough adsorption strengths of too low survey and cementing effect；The present invention have compared with
Good wellbore stability effect, preparation process is easy to control, easy to operate, stable product quality, and use has under the conditions of 150 DEG C
Preferable function and effect have preferable rheological characteristic by it for the water base drilling fluid system that crucial inorganic agent is constituted, inhibition, prevent
Collapsing property；
The present invention emphasizes that drilling fluid and formation rock are improved by chemical means to be acted on the basis of existing conventional anti-sloughing technique
Mechanical property afterwards, while reducing adverse effect of the formation rock by outside fluid.On the one hand, which enters with filtrate
After rock micropore, microcrack, chemical reaction or physical change occur under given conditions, is adsorbed in blowhole, and right
Its clay mineral is cementing, filling, solidifies, and improves rock cohesive force, forms cementation solidifying layer near wellbore zone, can prevent and slow down
Pore pressure transmitting, and improve its bearing capacity；On the other hand, borehole wall stabilizer is by micro force in rock surface, shape
At secured adsorption layer, help to weaken the interaction between rock and fluid, thus in mechanics --- two aspect collaboration of chemistry is made
With holding wellbore stability.Therefore develop one kind can either potent inhibitions shale hydration expand, while competent rock can be blocked
Stone improves mud shale mechanical property, enhances the additive for drilling fluid of borehole wall bearing capacity, effectively water-base drilling fluid can be pushed to take
For oil base drilling fluid, more efficiently holding wellbore stability, has great theoretical and practical significance.
Detailed description of the invention
Fig. 1 is the ultraviolet spectrogram of the high inhibition of the preparation of embodiment 1, strong rubber knot borehole wall stabilizer；
Fig. 2 is the shale expansion curve graph of test example 1；
Wherein, a is expansion curve of the calcium soil in clear water, and b is expansion curve of the calcium soil in 1% this product solution.
Specific embodiment
The present invention and its effect are described further combined with specific embodiments below, it should be appreciated that be described herein as
Specific embodiment be only that the present invention makes explanations, rather than limit the present invention.
Experimental method described in following embodiments is unless otherwise specified conventional method simultaneously；The reagent and equipment
Unless otherwise specified, it commercially obtains.
Embodiment 1：A kind of high inhibition that the present invention mentions, strong rubber knot borehole wall stabilizer and preparation method thereof, including it is following
Step：
3,4- dihydroxy benzenes propionic acid (2.65g, 14.5mmol) is dissolved in 5mLDMF, being added to 10mL mass fraction is 50%
EDC (5.55g, 29mmol) methanol solution in activate half an hour.Branching PEI (Mw=25k) (5g, 29mmol) is dissolved in
In 10mL methanol solution, then it is added dropwise in activated mixed solution, is stirred to react 12h.Product is precipitated with ether
Purification twice, is placed in the hydrochloric acid that pH is 4 and dialyses two days, dialyse 2h (molecular cut off 10000) in deionized water, freezing
It is dry.It is then added into the phosphate buffer solution of 196mL 0.2mol/L (pH 8), adjusts PEI- in final system
C concentration is 1mg/mL.For 24 hours by solution maintenance, keep its full cross-linked, (retention point in three days that then it dialyses in deionized water
Son is measured as 5 ten thousand), to remove uncrosslinked PEI-C.Sample is freeze-dried, is granulated, is placed at 4 DEG C and saves.
Synthetic route is as follows：
High inhibition manufactured in the present embodiment, the ultraviolet spectrogram of strong rubber knot borehole wall stabilizer are as shown in Figure 1.It can from Fig. 1
Out, 1706cm-1Locate it is corresponding be amido stretching vibration absworption peak, be methyl vibration absorption peak, 1090cm at 1380cm-1-1
Corresponding is typical C-O-C stretching vibration absworption peak in polyethylene glycol, and the absorption peak occurred at 1530cm-1 belongs to aromatic series
The stretching vibration of C=C, 1570cm-1Corresponding is the vibration absorption peak of amide II, it was demonstrated that the polyethyleneimine of catechol and branching
Amine is reacted.
Test example 1
Compatibility evaluation
In order to investigate adaptability of the sintetics of the present invention in water base drilling fluid system, carry out brown with live common sulfonation
Coal resin (SPNH), sulfonated-pheno-formoldehyde resin (SMP-II), aluminium base polymer (DSP-I) etc. carry out compatibility mechanism.Using implementation
1 product of example and above-mentioned additive for drilling fluid design two groups of drilling fluid compositions, to investigate 1 sample of embodiment and common inorganic agent in water
Compatibility in base drilling fluid.
No. 1：4% bentonite+1%CMC-L+0.15% FA367+2% sulfonated-pheno-formoldehyde resin SMP-II+2% sulfonated lignite
+ 1.5% Ultra Low Filtration Rate Additive SDN-1 of resin SPNH+2% emulsified asphalt
No. 2：4% bentonite+1%CMC-L+0.15% FA367+1%+2% sulfonated-pheno-formoldehyde resin SMP-II+2% of sample of the present invention
+ 1.5% Ultra Low Filtration Rate Additive SDN-1 of sulfonated lignite resin SPNH+2% emulsified asphalt
According to above-mentioned recipe configuration drilling fluid, and test slurries at 150 DEG C/16h heat rolling before and after performance, the results are shown in Table 1.
1 different formulations drilling fluid rheology filtration property of table
As can be seen that two sets of drilling fluid systems all have preferable rheology, filtration property from test result, sample of the present invention is added
After product, drilling fluid API leak-off and high temperature and pressure fluid loss decrease, and show that the sample has good compatibility.
Test example 2：
Rock specimen in uniaxial intensity test
Artificial sand rock rock sample (gas permeability 100mD) is placed in different samples, after 70 DEG C are impregnated for 24 hours, using TAW-100
Type microcomputer controls the uniaxial compressive strength of three-axis force tester (Changchun southern exposure test apparatus Co., Ltd) test rock sample, experiment
The results are shown in Table 2.
No. 1：It is untreated
No. 2：Clear water
No. 3：2% solution of the present invention
2 rock specimen in uniaxial intensity test result of table
The uniaxial compressive strength of dry rock sample is higher, is 12.4MPa, and clear water drops to 6.5MPa, decline about 50% after impregnating.2%
After product of the present invention processing, the bearing capacity of rock sample is significantly improved, and reaches 8.1MPa, is improved 25% or so compared with clear water, is shown this hair
Bright product can effectively consolidate artificial sand rock rock sample, effectively improve its bearing capacity.
Test example 3
Landwaste rolls dispersion test
Referring to the test method in Chinese patent document 201610953281.1, Shengli Oil Field clear water river group landwaste is detected in this sample
The landwaste rate of recovery in product, is expressed as a percentage.
4 landwaste rate of recovery test result of table
Being 84.01% from can be seen that rolling rate of recovery of the landwaste in product of the present invention solution in test result, being mentioned compared with clear water
It is high by nearly 170%, show that there is excellent inhibition Shale Hydration to disperse for high inhibition of the present invention, strong rubber knot borehole wall stabilizer
Performance.
Test example 4
Shale expansion test
The step of shale expansion is tested is as follows：Take magnificent Weihe River drilling fluid sodium bentonite (purchased from the limited public affairs of Shandong China Weihe River bentonite
Department) 10g, it is placed in grinding tool, to suppress 5min under 10MPa, the rock sample of one inch of diameter is made, and survey using vernier paper jam
Measure and record the original depth of rock sample.Then it is surveyed using NP-01 shale expansion tester (Bohai Sea drilling project Institute for Research and Technology)
Expansion height of the rock sample in different samples is tried to change with time.The ratio of rock sample expansion height and elemental height is expansion
Rate is expressed as a percentage.
Test results are shown in figure 2 for this test example.There it can be seen that after rock sample impregnates 8h in 1% solution of the present invention
Linear expansion rate be 13.54%, have dropped compared with the 74.05% of clear water more than 60 percentage points, rate of descent shows this hair up to 82%
It is bright that there is excellent inhibition Shale Hydration expansion effect.
Embodiment 2：A kind of high inhibition that the present invention mentions, strong rubber knot borehole wall stabilizer and preparation method thereof, including it is following
Step：
3,4-Dihydroxyphenylacetic acid (2.65g, 14.5mmol) is dissolved in 5mLDMF, being added to 10mL mass fraction is 50%
N-hydroxysuccinimide (NHS) (5.55g, 29mmol) methanol solution in activate half an hour.By branching（Polyethyleneimine）
PEI (Mw=25k) (5g, 29mmol) is dissolved in 10mL methanol solution, is then added dropwise in activated mixed solution,
It is stirred to react 12h.Twice with ether precipitation purification by product, it is placed in the formic acid that pH is 4 and dialyses two days, in deionized water thoroughly
It analyses 2h (molecular cut off 10000), freeze-drying.It is then added into the borate buffer solution of 196mL 0.2mol/L
In (pH 8), adjusting in final system PEI-C concentration is 1mg/mL.For 24 hours by solution maintenance, keep its full cross-linked, then by it
It dialyses in deionized water three days (molecular cut off is 50,000), to remove uncrosslinked PEI-C.Sample is freeze-dried, is made
Grain, is placed at 4 DEG C and saves.
Embodiment 3：A kind of high inhibition that the present invention mentions, strong rubber knot borehole wall stabilizer and preparation method thereof, including it is following
Step：
3,4-Dihydroxybenzoic acid (2.65g, 14.5mmol) is dissolved in 6mL ethyl alcohol, being added to 10mL mass fraction is 51%
2- (N- morpholine) ethanesulfonic acid monohydrate (MES) (5.55g, 29mmol) methanol solution in activate half an hour.By branching（It is poly-
Aziridine）PEI (Mw=25k) (5g, 29mmol) is dissolved in 10mL methanol solution, is then added dropwise to activated mixed
It closes in solution, is stirred to react 12h.Twice with ether precipitation purification by product, it is placed in the chloroform that pH is 4 and dialyses two days, going
It dialyses 2h (molecular cut off 10000) in ionized water, freeze-drying.It is then added into three hydroxyls of 196mL 0.2mol/L
Base aminomethane buffer solution (pH 8), adjusting PEI-C concentration in final system is 1mg/mL.For 24 hours by solution maintenance, make it
It is full cross-linked, then it is dialysed in deionized water three days (molecular cut off is 50,000), to remove uncrosslinked PEI-C.It will
Sample freeze-drying, is granulated, is placed at 4 DEG C and saves.
The above, is only part preferred embodiment of the invention, and anyone skilled in the art may benefit
Equivalent technical solution is modified or is revised as with the technical solution of above-mentioned elaboration.Therefore, technology according to the present invention
Any simple modification or substitute equivalents that scheme is carried out, belong to the greatest extent the scope of protection of present invention.
Claims (10)
1. a kind of high inhibition, strong rubber knot borehole wall stabilizer and preparation method thereof, it is characterized in that：High inhibition, strong rubber knot wellbore stability
The polyethyleneimine amine structure and the catechol group being grafted on main chain that agent contains the branching as main chain.
2. high inhibition according to claim 1, strong rubber knot borehole wall stabilizer and preparation method thereof, it is characterized in that：It is described strong
Inhibit, strong rubber knot borehole wall stabilizer contains the structure as shown in formula (I)：
Formula (I)
In formula (I), in formula (I), R1 can be hydrogen, carbon atom number be 1-4 alkyl, phenyl ,-NH2,
, R2 can be hydrogen ,-NH2, carbon atom number be 1-4 alkyl, phenyl,, and R1 and
At least one is in R2, R3 is the alkyl that carbon atom number is 1-4, and l, m, n can
It is identical or different, respectively 1 or more integer.
3. the preparation method of a kind of high inhibition as claimed in claim 1 or 2, strong rubber knot borehole wall stabilizer, it is characterized in that：Including
Following steps：
(1) reaction vessel is added in catechol monomer (II) and ethyl alcohol, sufficiently dissolved, activator and methanol are pressed into quality 1:
0.8 ~ 2 mixing, is added reaction vessel, by catechol monomer activation 0.5-1h；
(2) polyethyleneimine of branching (III) is mixed with methanol, is added dropwise in activated mixture after completely dissolution,
Wherein the polyethyleneimine of branching, activated mixture are reaction monomers mixture A, and it is single that methanol usage can be completely dissolved reaction
Body mixture A；
(3) lead to nitrogen 10 minutes and catalyst is added under agitation, the initial temperature of reaction is 60-100 DEG C, and the reaction time is
Then 4-12h purifies products therefrom ether twice, be placed in deionized water and dialyse, be freeze-dried, obtain intermediate product；
(4) intermediate product in step (3) is dissolved in buffer solution, conserves certain time, keeps its full cross-linked；
(5) methanol in rotary evaporation removal step (4) suspension, is subsequently placed in bag filter with deionized water dialysis, vacuum
Freeze-drying finally obtains white or lavender solid product, contains structural unit shown in formula (VI) in product；
The polyethyleneimine of the branching：The mass ratio of the material of catechol monomer is 1：(1.3-3.3).
4. the preparation method of high inhibition according to claim 3, strong rubber knot borehole wall stabilizer, it is characterized in that：Described swashs
Agent living is 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride (EDC), n-hydroxysuccinimide (NHS), 2-
One of (N- morpholine) ethanesulfonic acid monohydrate (MES) is a variety of, the ratio between the amount of substance of activator and catechol monomer
It is 1:0.5-2.
5. the preparation method of high inhibition according to claim 3, strong rubber knot borehole wall stabilizer, it is characterized in that：Described urges
Agent is one of formic acid, glacial acetic acid, propionic acid, hydrochloric acid, chloroform or a variety of, and the catalyst is reaction monomers mixture A
The 0.1% ~ 0.5% of gross mass.
6. the preparation method of high inhibition according to claim 3, strong rubber knot borehole wall stabilizer, it is characterized in that：Neighbour's benzene
Diphenol group general formula such as (II)：
Formula (II)
In formula, R is the alkyl that carbon atom number is 1 ~ 4.
7. the preparation method of high inhibition according to claim 3, strong rubber knot borehole wall stabilizer, it is characterized in that：The branching
Polyethyleneimine general formula such as (III), average weight-molecular mass can be 10000-80000g/mol,
Formula (III)
In formula, l, m, n be may be the same or different, respectively 1 or more integer.
8. the preparation method of high inhibition according to claim 6, strong rubber knot borehole wall stabilizer, it is characterized in that：Neighbour's benzene
Diphenol monomer can be the compound comprising formula (II), and including but are not limited to catechol group is 3,4- dihydroxy benzenes first
Acid, 3,4-Dihydroxyphenylacetic acid, 3,4- dihydroxy benzenes propionic acid it is one or more.
9. the preparation method of high inhibition according to claim 3, strong rubber knot borehole wall stabilizer, it is characterized in that：Described is slow
Rushing solution can be borate buffer solution, citrate buffer solution, phosphate buffer solution, trihydroxy aminomethane buffer
One of solution, the pH of buffer solution are 6-8.
10. the preparation method of high inhibition according to claim 3, strong rubber knot borehole wall stabilizer, it is characterized in that：Described supports
The shield time is 4-48h.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109652031A (en) * | 2018-12-25 | 2019-04-19 | 中石化石油工程技术服务有限公司 | A kind of strong wall drilling fluid system and preparation method thereof |
| CN109679598A (en) * | 2018-12-25 | 2019-04-26 | 中石化石油工程技术服务有限公司 | A kind of anti-collapse water-base drilling fluid of strong wall and preparation method thereof |
| CN113698534A (en) * | 2020-08-26 | 2021-11-26 | 中国石油大学(北京) | Polymer for high-performance environment-friendly borehole wall stabilizer for water-based drilling fluid |
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| CN1186506A (en) * | 1995-05-30 | 1998-07-01 | 加利福尼亚大学董事会 | Water-soluble polymers and compositions thereof |
| WO2013077476A1 (en) * | 2011-11-21 | 2013-05-30 | 한국과학기술원 | Hydrogel comprising catechol group-coupled chitosan or polyamine and poloxamer comprising thiol group coupled to end thereof, preparation method thereof, and hemostat using same |
| CN104310828A (en) * | 2014-09-28 | 2015-01-28 | 华中师范大学 | Method for preparing alpha-semi-hydrated gypsum by use of polyphenol grafted polyethyleneimine as crystal modifier |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1186506A (en) * | 1995-05-30 | 1998-07-01 | 加利福尼亚大学董事会 | Water-soluble polymers and compositions thereof |
| WO2013077476A1 (en) * | 2011-11-21 | 2013-05-30 | 한국과학기술원 | Hydrogel comprising catechol group-coupled chitosan or polyamine and poloxamer comprising thiol group coupled to end thereof, preparation method thereof, and hemostat using same |
| CN104310828A (en) * | 2014-09-28 | 2015-01-28 | 华中师范大学 | Method for preparing alpha-semi-hydrated gypsum by use of polyphenol grafted polyethyleneimine as crystal modifier |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109652031A (en) * | 2018-12-25 | 2019-04-19 | 中石化石油工程技术服务有限公司 | A kind of strong wall drilling fluid system and preparation method thereof |
| CN109679598A (en) * | 2018-12-25 | 2019-04-26 | 中石化石油工程技术服务有限公司 | A kind of anti-collapse water-base drilling fluid of strong wall and preparation method thereof |
| CN109679598B (en) * | 2018-12-25 | 2023-03-31 | 中石化石油工程技术服务有限公司 | Strong-wall anti-collapse water-based drilling fluid and preparation method thereof |
| CN113698534A (en) * | 2020-08-26 | 2021-11-26 | 中国石油大学(北京) | Polymer for high-performance environment-friendly borehole wall stabilizer for water-based drilling fluid |
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