CN106519256A - Preparation method and application of hyperbranched polymer taking triethylenetetramine as initiator - Google Patents
Preparation method and application of hyperbranched polymer taking triethylenetetramine as initiator Download PDFInfo
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- CN106519256A CN106519256A CN201610983311.3A CN201610983311A CN106519256A CN 106519256 A CN106519256 A CN 106519256A CN 201610983311 A CN201610983311 A CN 201610983311A CN 106519256 A CN106519256 A CN 106519256A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/005—Hyperbranched macromolecules
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G33/00—Dewatering or demulsification of hydrocarbon oils
- C10G33/04—Dewatering or demulsification of hydrocarbon oils with chemical means
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1037—Hydrocarbon fractions
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/02—Gasoline
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/04—Diesel oil
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Abstract
The invention relates to a preparation method of a hyperbranched polymer taking triethylenetetramine as the initiator. The method comprises the following steps that (1) triethylenetetramine is dissolved in an organic solvent, methyl acrylate is dropwise added, and an intermediate product is obtained after 40-60 h of Michael addition reaction at room temperature; the intermediate product obtained in the step (1) is warmed to the temperature of 80-150 DEG C for decompression condensation reaction, and a coarse product is obtained; (3) the coarse product obtained in the step (2) is subjected to diethyl ether separation and rotary evaporation, and the hyperbranched polymer taking the triethylenetetramine as the initiator is obtained. The end group of the hyperbranched polymer is taken as amido, the framework contains structures of a large number of acylamino and the like, the highly branched structures can reach the oil-water interface rapidly, the liquid film breaking speed is accelerated, the oil drop breaking, aggregation and oil-water separation speeds are further accelerated, and a better demulsification effect is realized.
Description
Technical field
The present invention relates to petroleum additive technical field, and in particular to a kind of over-expense with trien as initiator
The preparation method and application of fluidized polymer.
Background technology
Polyamide amine polymer is that a class studies to obtain more ripe dendroid branched polymer (Dendritic
Polymer), Tomalia in 2005 et al. (Progress in Polymer Science.2005,30,294-324.) synthesis
Polyamide-amide class dendritic (being designated as PAMAM), such polymer generally with ammonia or ethylenediamine as core, molecular weight
Highest is more than 930000g/mol, and polydispersity is less than 1.8, and, macroscopically for colourless to flaxen liquid, volatility is low for which,
Kinematic viscosity at 25 DEG C is 10~10000mm2/s。
Dissaving polymer is similar with dendritic (dendrimers) structure, because of its unique architectural feature, such as
Low-viscosity, high rheological variation, good dissolubility and a large amount of modifiable functional end-group etc., excite dense emerging of scientist
Interest.
Dissaving polymer requires perfect structure, dissaving polymer different from dendritic (dendrimers)
Extensively, generally using " one kettle way " synthesis, simple synthetic method is easy, therefore it becomes field of polymer technology research heat for raw material sources
One of point, and realize applying and obtaining good in fields such as nano science, biomedicine, sensor, petrochemical industry and catalyst
Good effect.
In recent years, as the crude oil of 30%-35% is only produced by primary oil recovery and secondary oil recovery;Tertiary oil recovery is big in oil field
Scale is carried out, as the application (water drive, polymer flooding, binary combination flooding, ternary composite driving) of various production techniques causes crude oil
It is plucked out of in the form of emulsion more;Meanwhile, in Produced Liquid, salinity is very high.Collection, transport and the course of processing that this gives crude oil
Inconvenience is brought, and corrodes Oilfield Pipelines, increase cost for oil production, and the place of the synthesis of demulsifier and application to oil field mining liquid
Vital effect is played in reason or sewage disposal.
The content of the invention
Present invention aims to the deficiencies in the prior art, there is provided a kind of super with trien as initiator
The preparation method and application of branched polymer, reaches the purpose of quick, efficient breakdown of emulsion.
Technical scheme provided by the present invention is:
A kind of preparation method of the dissaving polymer with trien as initiator, comprises the steps:
1) trien is dissolved in organic solvent, is then added dropwise over acrylic acid methyl ester., at room temperature through 40
The Michael additive reaction of~60h, obtains intermediate product;
2) by step 1) intermediate product that obtains is warming up to 80~150 DEG C and carries out decompression condensation reaction, obtains crude product;
3) by step 2) crude product that obtains separated through ether, revolving, obtain with trien as initiator
Dissaving polymer.
In above-mentioned technical proposal, trien obtains hyperbranched polymerization with acrylic acid methyl ester. by " one kettle way " synthesis
Thing, the dissaving polymer center are trien, and end group is amido;Its number average molecular weight distribution be 3000~
8000.Compared to the dissaving polymer with ethylenediamine as initiator, the hyperbranched polymerization with trien as initiator
Thing terminal number showed increased, amino content increase, and with very low dynamical interfacial tension value, can not only be quick
Breakdown of emulsion balance is reached, very high demulsification efficiency is obtained, and the water deviate from is very clear, absorbance is very high.
As the end group of dissaving polymer is amido, containing the structures such as a large amount of amide groups, the strong hydrophilicity of amino in skeleton
Property give demulsifier and quickly reach oil-water interfaces, amide group can multipoint adsorption in oil-water interfaces, play destruction oil-water interfaces
The effect of film, this kind of highly branched structure give which and accelerate to up to oil-water interfaces, accelerate the speed of liquid-sheet disintegration so that oil
Drop rupture, coalescence, the speed of oil-water separation further speed up, and reach good demulsification.
Preferably, the step 1) in organic solvent be methanol, ethanol.
Preferably, the step 1) in the mass ratio of trien and acrylic acid methyl ester. be 3:2~5:2.
Preferably, the step 2) in condensation reaction response time be 10~12h.
It is hyperbranched with trien as initiator that the present invention also provides that a kind of preparation method described above obtains
Application of the polymer as demulsifier.
Preferably, the dissaving polymer with trien as initiator is distributed to oil-in-water type emulsus
Breakdown of emulsion is carried out in liquid.
Preferably, the temperature of the breakdown of emulsion is 30~60 DEG C, the sedimentation time is 1~30min.
Preferably, the dissaving polymer with trien as initiator is in oil-in-water emulsion
Addition is 10~40mg/L.Addition is less than 10mg/L, and demulsification is not good;Addition is more than 40mg/L, and demulsification becomes
Change less, but Financial cost increases a lot.
Preferably, the oil phase in the oil-in-water emulsion is simulation oil or actual oil.
Preferably, the simulation oil is n-dodecane, n-tridecane, n-tetradecane or hexadecane, the actual oil
For kerosene, bavin Water Oil Or Gas.
Preferably, the salinity of the water phase in the oil-in-water emulsion is 0~10000mg/L, wherein in water phase
NaCl and CaCl2Mass ratio be 0.8~1.2.
Compared with the existing technology, beneficial effects of the present invention are embodied in:
As the end group of the dissaving polymer with trien as initiator is as amido, in skeleton, contain a large amount of acyls
The structures such as amido, this kind of highly branched structure give which and accelerate to up to oil-water interfaces, accelerate the speed of liquid-sheet disintegration so that
Oil droplet rupture, coalescence, the speed of oil-water separation further speed up, and reach good demulsification.
Description of the drawings
Structural representations of the Fig. 1 for the dissaving polymer (h-PAMAM) in embodiment 1 with trien as initiator
Figure.
Specific embodiment
Following examples and application examples can make those skilled in the art be more fully understood from the present invention, but limit never in any form
The present invention.
Oil removal efficiency is obtained by ultraviolet spectrophotometer survey calculation, adds the concentration of demulsifier in uniform temperature
With not plus demulsifier concentration difference divided by not plus the concentration of demulsifier obtains oil removal efficiency.
Absorbance is obtained by ultraviolet spectrophotometer survey calculation, adds the absorbance of demulsifier in uniform temperature
Value with plus demulsifier absorbance difference divided by not plus the absorbance of demulsifier obtains absorbance.
Embodiment 1:It is prepared by the dissaving polymer (h-PAMAM) with trien as initiator
Take 29.2g triens to be dissolved in 30mL absolute methanols, weigh 17.22g acrylic acid methyl ester .s and dropwise instill instead
System is answered, room temperature reaction 52h is stirred vigorously.Product carries out reducing pressure condensation reaction to obtain the product of high polymerization degree, arranges
From 80 DEG C to 140 DEG C, the response time is 10h to heating schedule;Subsequently, crude product is stirred in being poured into 250mL ether after being cooled to room temperature
60min is mixed, the thick liquid that the yellow transparent with fluorescent characteristic can be observed is sunken to lower floor, discard upper strata ether, repeat heavy
Form sediment 2 times, the lower 60 DEG C of revolvings of vacuum are obtained h-PAMAM.
The structural representation of the dissaving polymer (h-PAMAM) with trien as initiator (is needed as shown in Figure 1
It is noted that as dissaving structure is changeable and complicated, shown structure is merely illustrative).
Embodiment 2:It is prepared by the dissaving polymer (h-PAMAM) with trien as initiator
Take 46.7g triens to be dissolved in 50mL absolute methanols, weigh 20.7g acrylic acid methyl ester .s and dropwise instill reaction
System, is stirred vigorously room temperature reaction 60h.Product carries out reducing pressure condensation reaction to obtain the product of high polymerization degree, arranges and rises
From 80 DEG C to 140 DEG C, the response time is 12h to warm program;Subsequently, crude product is stirred in being poured into 300mL ether after being cooled to room temperature
60min, the thick liquid that the yellow transparent with fluorescent characteristic can be observed are sunken to lower floor, discard upper strata ether, repeat precipitation 2
Secondary, the lower 60 DEG C of revolvings of vacuum are obtained h-PAMAM.
Application examples 1
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
It is dissolved in hexadecane as oil phase, oil-in-water emulsion of the salinity for 0mg/L.At 30 DEG C, under 40mg/L concentration, measurement
Absorbance when sedimentation time is 360min.As a result show, absorbancies of the h-PAMAM under this sedimentation time is 80%, phase
Than the modified ultra-branching polymer under equal conditions with ethylenediamine as initiator transmittance values be 45%, be obviously improved.
Application examples 2
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
It is dissolved in n-tetradecane as oil phase, oil-in-water emulsion of the salinity for 5000mg/L.At 30 DEG C, under 40mg/L concentration,
Absorbance when the measurement sedimentation time is 360min.As a result show, absorbancies of the h-PAMAM under this sedimentation time is
75%, compared to the modified ultra-branching polymer under equal conditions with ethylenediamine as initiator transmittance values be 44%, improve
Substantially.
Application examples 3
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 20mg/L
It is dissolved in n-tetradecane as oil phase, oil-in-water emulsion of the salinity for 2500mg/L.At 30 DEG C, under 40mg/L concentration,
Absorbance when the measurement sedimentation time is 360min.As a result show, absorbancies of the h-PAMAM under this sedimentation time is
77%, compared to the modified ultra-branching polymer under equal conditions with ethylenediamine as initiator transmittance values be 43%, improve
Substantially.
Application examples 4
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 20mg/L
It is dissolved in hexadecane as oil phase, oil-in-water emulsion of the salinity for 7500mg/L.When surveying sedimentation respectively at 45 DEG C
Between for 1,10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times by
4% is respectively increased to 53%, 70%, 75% and 83%.
Application examples 5
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 20mg/L
It is dissolved in n-tridecane as oil phase, oil-in-water emulsion of the salinity for 10000mg/L.When surveying sedimentation respectively at 45 DEG C
Between for 1,10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times by
4% is respectively increased to 51%, 68%, 73% and 81%.
Application examples 6
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 20mg/L
It is dissolved in n-tridecane as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveying the sedimentation time at 60 DEG C respectively is
1st, 10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7% point
Indescribably up to 63%, 79%, 81% and 84%.
Application examples 7
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
It is dissolved in n-tetradecane as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveying the sedimentation time at 60 DEG C respectively is
1st, 10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7% point
Indescribably up to 79%, 86%, 93% and 95%.
Application examples 8
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
It is dissolved in hexadecane as oil phase, oil-in-water emulsion of the salinity for 2500mg/L.When surveying sedimentation respectively at 60 DEG C
Between for 1,10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times by
7% is respectively increased to 77%, 85%, 90% and 94%.
Application examples 9
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
It is dissolved in n-tridecane as oil phase, oil-in-water emulsion of the salinity for 5000mg/L.When surveying sedimentation respectively at 60 DEG C
Between for 1,10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times by
7% is respectively increased to 75%, 83%, 89% and 93%.
Application examples 10
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
It is dissolved in n-dodecane as oil phase, oil-in-water emulsion of the salinity for 2500mg/L.When surveying sedimentation respectively at 60 DEG C
Between for 1,10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times by
7% is respectively increased to 76%, 86%, 91% and 93%.
Application examples 11
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 10mg/L
It is dissolved in n-tridecane as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveying the sedimentation time at 60 DEG C respectively is
1st, 10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7% point
Indescribably up to 53%, 62%, 72% and 80%.
Application examples 12
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 30mg/L
It is dissolved in n-tridecane as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveying the sedimentation time at 60 DEG C respectively is
1st, 10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7% point
Indescribably up to 77%, 82%, 86% and 90%.
Application examples 13
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
It is dissolved in aerial kerosene as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveying the sedimentation time at 60 DEG C respectively is
1st, 10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7% point
Indescribably up to 78%, 85%, 92% and 95%.
Application examples 14
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
It is dissolved in diesel oil as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveyed at 60 DEG C respectively the sedimentation time for 1,
10th, 20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7% difference
Improve to 76%, 84%, 91% and 94%.
Application examples 15
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
It is dissolved in gasoline as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveyed at 60 DEG C respectively the sedimentation time for 1,
10th, 20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7% difference
Improve to 74%, 83%, 90% and 93%.
Application examples 16
The h-PAMAM (number average molecular weight distribution is 3000~8000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
It is dissolved in gasoline as oil phase, oil-in-water emulsion of the salinity for 0mg/L.At 30 DEG C, under 40mg/L concentration, measurement sedimentation
Absorbance when time is 360min.As a result show, absorbancies of the h-PAMAM under this sedimentation time is 78%, compared to
The transmittance values of the modified ultra-branching polymer under equal conditions with ethylenediamine as initiator are 45%, are obviously improved.
Do exemplary description above to the present invention, what deserves to be explained is, in the case of without departing from core of the present invention,
Any simple deformation, modification (species including sedimentation time, breakdown of emulsion temperature and emulsion oil phase etc.) or other this areas
Technical staff can not spend the equivalent of creative work to each fall within protection scope of the present invention.
Claims (10)
1. a kind of preparation method of the dissaving polymer with trien as initiator, it is characterised in that including as follows
Step:
1) trien is dissolved in organic solvent, is then added dropwise over acrylic acid methyl ester., at room temperature through 40~60h
Michael additive reaction, obtain intermediate product;
2) by step 1) intermediate product that obtains is warming up to 80~150 DEG C and carries out decompression condensation reaction, obtains crude product;
3) by step 2) crude product that obtains separated through ether, revolving, obtains the over-expense with trien as initiator
Fluidized polymer.
2. the preparation method of the dissaving polymer with trien as initiator according to claim 1, which is special
Levy and be, the step 1) in trien be 3 with the mass ratio of acrylic acid methyl ester.:2~5:2.
3. the preparation method of the dissaving polymer with trien as initiator according to claim 1, which is special
Levy and be, the step 2) in response time of condensation reaction be 10~12h.
4. the over-expense with trien as initiator that a kind of preparation method as described in claims 1 to 3 is arbitrary is obtained
Application of the fluidized polymer as demulsifier.
5. the dissaving polymer using trien as initiator according to claim 4 as demulsifier should
With, it is characterised in that the dissaving polymer with trien as initiator is distributed to into oil-in-water emulsion
In carry out breakdown of emulsion.
6. the dissaving polymer using trien as initiator according to claim 5 as demulsifier should
With, it is characterised in that the temperature of the breakdown of emulsion is 30~60 DEG C, and the sedimentation time is 1~30min.
7. the dissaving polymer using trien as initiator according to claim 5 as demulsifier should
With, it is characterised in that the adding in oil-in-water emulsion of the dissaving polymer with trien as initiator
Dosage is 10~40mg/L.
8. the dissaving polymer using trien as initiator according to claim 5 as demulsifier should
With, it is characterised in that the oil phase in the oil-in-water emulsion is simulation oil or actual oil.
9. the dissaving polymer using trien as initiator according to claim 8 as demulsifier should
With, it is characterised in that the simulation oil is n-dodecane, n-tridecane, n-tetradecane or hexadecane, and the actual oil is coal
Oil, bavin Water Oil Or Gas.
10. the dissaving polymer using trien as initiator according to claim 5 as demulsifier should
With, it is characterised in that the salinity of the water phase in the oil-in-water emulsion is 0~10000mg/L, wherein NaCl in water phase
And CaCl2Mass ratio be 0.8~1.2.
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CN109575280A (en) * | 2018-11-27 | 2019-04-05 | 浙江大学 | The method being demulsified using Ambident hyperbranched daiamid to oil-in-water emulsion |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN109517169A (en) * | 2018-10-19 | 2019-03-26 | 浙江大学 | A kind of Ambident hyperbranched polymer and its preparation and application |
CN109575280A (en) * | 2018-11-27 | 2019-04-05 | 浙江大学 | The method being demulsified using Ambident hyperbranched daiamid to oil-in-water emulsion |
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