CN113563574B - Compound used as demulsifier and preparation method thereof - Google Patents
Compound used as demulsifier and preparation method thereof Download PDFInfo
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- CN113563574B CN113563574B CN202010349154.7A CN202010349154A CN113563574B CN 113563574 B CN113563574 B CN 113563574B CN 202010349154 A CN202010349154 A CN 202010349154A CN 113563574 B CN113563574 B CN 113563574B
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- 150000001875 compounds Chemical class 0.000 title abstract description 11
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 34
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 24
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 22
- 229960000583 acetic acid Drugs 0.000 claims description 17
- 239000012362 glacial acetic acid Substances 0.000 claims description 17
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 15
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 15
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000000295 fuel oil Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 12
- 239000010779 crude oil Substances 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 230000018044 dehydration Effects 0.000 description 7
- 238000006297 dehydration reaction Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000000412 dendrimer Substances 0.000 description 3
- 229920000736 dendritic polymer Polymers 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- -1 polyethylene Polymers 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033558 biomineral tissue development Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920000587 hyperbranched polymer Polymers 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
- C08G65/2633—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen the other compounds containing amide groups
-
- 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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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a compound used as a demulsifier and a preparation method thereof. The structural formula of the compound is shown as a formula I,wherein EO isPO is
Description
Technical Field
The invention provides a compound, in particular a compound used as a thick oil demulsifier.
Background
The thick oil has high viscosity and high asphaltene content, and the asphaltene has certain surface activity and is adsorbed on an oil-water interface, so that the strength of the oil-water interface film is enhanced, and the thick oil has high demulsification and dehydration difficulty.
The crude oil demulsifier used at home and abroad at present can be structurally divided into polyether demulsifiers and non-polyether demulsifiers, and is similar to other foreign countries, and the non-ionic polyoxyethylene polyoxypropylene block copolymer is mainly used, but the initiator, the block number, the molecular weight and the like are different. The demulsifiers classified according to the initiator include demulsifiers with alcohol compounds as the initiator, block polyethers with polyethylene polyamine as the initiator, demulsifiers of phenolic resin series, demulsifiers of phenolic amine resin series, silicon-containing demulsifiers and the like. Wherein the thick oil demulsifier is mainly composed of polyethylene polyamine and phenolic resin.
The composition of thick oil emulsions is quite complex and demulsification is difficult, depending on the family composition, nature, degree of emulsification and its stability factors of the thick oil, as well as on the structure and performance of the demulsifier. Because of the different compositions of thick oil emulsions extracted from different blocks and different oil wells, and the characteristics of single property, strong selectivity and the like of the demulsifier, the development of the corresponding demulsifier for specific thick oil is particularly important. And the thick oil has high viscosity, high density and difficult oil-water separation, and demulsification and dehydration are often required at high temperature, so that the thick oil is concentrated and transported, and the demulsification energy consumption is high. Therefore, the development of high-efficiency low-temperature thick oil demulsifiers is an important subject in oilfield production.
Polyamide-amine is a high molecular polymer with a special structure, and the terminal group of the polyamide-amine has a large number of functional groups and excellent surface activity and shearing resistance, so the polyamide-amine has been widely paid attention as a novel demulsifier. With the wide use of tertiary oil recovery technology, the composition of oilfield produced fluid is greatly changed, and the composition of emulsion becomes more complex due to the use of various chemical agents, so that the emulsion stability is gradually enhanced, and the difficulty of oil-water separation is increased. For the above reasons, research into developing novel efficient demulsifiers has entered a new stage.
The conventional polyamide is prepared by adopting fatty amine and methyl methacrylate as raw materials to react, and has poor acting force on crude oil, particularly thick oil, asphaltene and colloid in the fatty amine and the thick oil, and unsatisfactory demulsification effect on the thick oil.
Disclosure of Invention
The invention provides a compound, the structural formula of which is shown as the formula I,
wherein EO isPO is->m, n is the mole fraction of PO and EO, m: n=1, (3-4).
The second aspect of the present invention provides a process for preparing a compound according to one of the present invention, comprising the steps of:
1) Dissolving p-phenylenediamine in glacial acetic acid, adding methyl acrylate into the solution, and performing a first reaction at a first temperature to obtain a first reaction solution containing G0.5;
2) Dissolving the G0.5 and p-phenylenediamine in glacial acetic acid, and performing a second reaction at a second temperature to obtain a second reaction system consisting of G1.0 and a second reaction liquid, wherein the second reaction is a reflux reaction, and the G1.0 is a solid insoluble in the second reaction liquid;
3) Heating the G1.0 and the catalyst to a third temperature, adding ethylene oxide to perform a third reaction, and continuing to perform a fourth reaction after the pressure is returned; and then heating to a fourth temperature, adding propylene oxide to perform a fifth reaction, and continuing to perform a sixth reaction after the pressure falls back to obtain the compound.
In one embodiment, the catalyst is potassium hydroxide.
In a specific embodiment, in step 1), the molar ratio of the p-phenylenediamine to the methyl acrylate is 1 (15-30).
In a specific embodiment, in step 2), the mass ratio of G0.5 to p-phenylenediamine is 1: (5-8).
In a specific embodiment, in step 3), the G1.0 accounts for 0.3 to 3% by mass and the catalyst accounts for 0.5 to 2% by mass, based on the total mass of the G1.0, the catalyst, the ethylene oxide and the propylene oxide.
In a specific embodiment, in step 3), the molar ratio of said ethylene oxide to said propylene oxide is 1: (3-4).
In one embodiment, the first temperature is 70 to 90 ℃.
In a specific embodiment, the second temperature is 85 to 100 ℃.
In one embodiment, the third temperature is 120 to 135 ℃.
In a specific embodiment, the fourth temperature is between 130 and 145 ℃.
In a specific embodiment, the time of the first reaction is 4 to 6 hours.
In a specific embodiment, the second reaction time is 18 to 30 hours.
In a specific embodiment, the fourth reaction time is 30 to 60 minutes.
In a specific embodiment, the sixth reaction time is 30 to 60 minutes.
In a specific embodiment, the G0.5 is purified by distillation under reduced pressure.
In one embodiment, the G1.0 is obtained by filtration from the second reaction system, washing and drying.
In one embodiment, the G1.0 is filtered from the second reaction system and washed with glacial acetic acid.
In one embodiment, the G1.0 is dried under vacuum at 40 to 50 ℃ for 8 to 24 hours after filtration washing.
The third invention provides application of the compound according to the first invention or the compound prepared by the method according to any one of the second invention in use as demulsifiers.
In one embodiment, the demulsifier is a thick oil demulsifier.
The invention has the beneficial effects that:
the invention adopts aromatic amine to react with methyl acrylate to prepare polyamide-amine hyperbranched polymer of aromatic amine, and then uses polyamide-amine as an initiator to prepare the thick oil demulsifier, which has good interaction with asphaltene and good thick oil demulsification effect.
Detailed Description
The invention is further illustrated below with reference to the examples, which are merely illustrative of the invention and do not constitute a limitation of the invention in any way.
Example 1
Preparation of demulsifier 1:
(1) Dissolving 4G of p-phenylenediamine in 8mL of glacial acetic acid, slowly dropwise adding 47.78G of methyl acrylate into the solution, reacting for 4 hours at 70 ℃, and removing the glacial acetic acid and excessive methyl acrylate by reduced pressure distillation after the reaction to obtain light yellow oily liquid, namely G0.5 dendrimer;
(2) 1G of G0.5 and 5G of p-phenylenediamine are weighed and dissolved in 40mL of glacial acetic acid until the mixture is completely dissolved, the mixture is refluxed for 18 hours at the temperature of 85 ℃, the reaction system is filtered, filter residues are washed by the glacial acetic acid, and the mixture is dried for 12 hours at the temperature of 45 ℃ in vacuum to obtain a product G1.0;
(3) Taking the total mass of G1.0, potassium hydroxide, ethylene oxide and propylene oxide as 100%, wherein the adding mass ratio of G1.0 serving as an initiator is 0.3%, the adding mass ratio of potassium hydroxide serving as a catalyst is 0.5%, adding ethylene oxide for reaction when the heating temperature is increased to 120 ℃, and reacting for 30min after the pressure is returned; and (3) heating to 135 ℃, adding propylene oxide for reaction, wherein the molar ratio of the ethylene oxide to the propylene oxide is 1:3, reacting for 30min after the pressure is back, and finally cooling and discharging to obtain the demulsifier 1, wherein the structural formula is shown as formula I, and m is n=1:3.
Example 2
Preparation of demulsifier 2:
(1) Dissolving 4G of p-phenylenediamine in 8mL of glacial acetic acid, slowly dropwise adding 63.71G of methyl acrylate into the solution, reacting for 5 hours at 80 ℃, and removing the glacial acetic acid and excessive methyl acrylate by reduced pressure distillation after the reaction to obtain light yellow oily liquid, namely G0.5 dendrimer;
(2) 1G of G0.5 and 6G of p-phenylenediamine are weighed and dissolved in 40mL of glacial acetic acid until the mixture is completely dissolved, the mixture is refluxed for 24 hours at 90 ℃, the reaction system is filtered, filter residues are washed by the glacial acetic acid, and the mixture is dried for 8 hours at 40 ℃ in vacuum to obtain a product G1.0;
(3) Taking the total mass of G1.0, potassium hydroxide, ethylene oxide and propylene oxide as 100%, wherein the adding mass ratio of G1.0 serving as an initiator is 1%, the adding mass ratio of potassium hydroxide serving as a catalyst is 1%, adding ethylene oxide for reaction when the heating temperature is increased to 130 ℃, and reacting for 45min after the pressure is dropped; and (3) heating to 140 ℃, adding propylene oxide for reaction, wherein the molar ratio of the ethylene oxide to the propylene oxide is 1:4, reacting for 45min after the pressure is back, and finally cooling and discharging to obtain the demulsifier 2, wherein the structural formula is shown as formula I, and m is n=1:4.
Example 3
Preparation of demulsifier 3:
(1) Dissolving 4G of p-phenylenediamine in 8mL of glacial acetic acid, slowly dropwise adding 95.57G of methyl acrylate into the solution, reacting for 6 hours at 90 ℃, and removing the glacial acetic acid and excessive methyl acrylate by reduced pressure distillation after the reaction to obtain light yellow oily liquid, namely G0.5 dendrimer;
(2) 1G of G0.5 and 8G of p-phenylenediamine are weighed, dissolved in 40mL of glacial acetic acid and subjected to ultrasonic treatment until the mixture is completely dissolved, the reaction system is filtered after reflux for 30 hours at the temperature of 100 ℃, filter residues are washed by the glacial acetic acid, and vacuum drying is carried out for 24 hours at the temperature of 50 ℃ to obtain a product G1.0;
(3) Taking the total mass of G1.0G 1.0, potassium hydroxide, ethylene oxide and propylene oxide as 100%, taking the mass ratio of G1.0 as an initiator to be 2%, taking the mass ratio of potassium hydroxide as a catalyst to be 2%, adding ethylene oxide to continuously raise the temperature when the heating temperature is raised to 120 ℃, ensuring the temperature not to exceed 135 ℃, carrying out reaction, and reacting for 60min after the pressure is returned; and then, heating to 145 ℃, adding propylene oxide for reaction, wherein the molar ratio of the ethylene oxide to the propylene oxide is 1:4, reacting for 60 minutes after the pressure is back, and finally cooling and discharging to obtain the demulsifier 3, wherein the structural formula is shown as formula I, and m is n=1:4.
Example 4
Crude oil: the viscosity at 50 ℃ is 27500mPa.s, and the asphaltene content reaches 10.12%.
Demulsifiers 1, 2 and 3 were each formulated with ethanol as 1wt% strength demulsifier solutions.
The demulsification experiment is specifically operated as follows:
according to the standard of SY/T5281-2000 crude oil demulsifier service performance detection method-bottle test method in the oil and gas industry standard of the people's republic of China, firstly, using simulated mineralized water with the mineralization degree of 200000mg/L to prepare W/O type crude oil emulsion with the water content of 20% by using the crude oil. 80mL (Ve) of the crude oil emulsion prepared was then poured into a dewatering bottle, and the thermostatic water bath was warmed to 70℃for in situ demulsification and dewatering operations. Wherein the liquid level of the constant-temperature water bath is higher than that of the crude oil emulsion in the dehydration bottle. The demulsifier solutions were added to the demulsifiers with pipettes to 200ppm, respectively. After the bottle cap is screwed, the bottle cap is turned upside down for 2 to 5 times, after the bottle cap is slowly loosened and deflated, the bottle cap is directly vibrated by adopting a manual mode, the vibration amplitude is larger than 20cm, after the bottle cap is fully and uniformly mixed, the bottle cap is loosened, and the bottle cap is placed in a constant-temperature water bath at 70 ℃ again for standing and sedimentation. The amount of water (Vw) removed at different times, the water clarity at 24h, and the oil-water interface uniformity at 24h were visually examined and recorded. 3 replicates were set up.
The dehydration rate at different times was calculated according to the following formula:
where Dr represents the dehydration rate, ve represents the volume of the crude oil emulsion, and Vwt represents the volume of the water removed at different times.
The results of the tests on the dehydration rate, the 24h water clarity and the 24h interface uniformity at different times are shown in Table 1.
TABLE 1
As shown in Table 1, the demulsifier of the invention has good demulsification effect on thick oil, and the dehydration rate of the demulsifier reaches more than 80% at 70 ℃ under the concentration of 200ppm, so that the oil-water interface is clear, and the dehydrated water is clear.
Claims (6)
1. Use of a demulsifier for demulsification of an asphaltene-containing heavy oil, the method for preparing the demulsifier comprising the steps of:
1) Dissolving p-phenylenediamine in glacial acetic acid, adding methyl acrylate into the solution, and performing a first reaction at a first temperature to obtain a first reaction solution containing G0.5, wherein the molar ratio of the p-phenylenediamine to the methyl acrylate is 1 (15-30);
2) Dissolving the G0.5 and p-phenylenediamine in glacial acetic acid, and performing a second reaction at a second temperature to obtain a second reaction system consisting of G1.0 and a second reaction liquid, wherein the second reaction is a reflux reaction, the G1.0 is a solid insoluble in the second reaction liquid, and the mass ratio of the G0.5 to the p-phenylenediamine is 1 (5-8);
3) Heating the G1.0 and the catalyst to a third temperature, adding ethylene oxide to perform a third reaction, and continuing to perform a fourth reaction after the pressure is returned; and then heating to a fourth temperature, adding propylene oxide to perform a fifth reaction, and continuing to perform a sixth reaction after the pressure falls back to obtain the demulsifier, wherein the molar ratio of the ethylene oxide to the propylene oxide is 1 (3-4).
2. Use according to claim 1, wherein the catalyst is potassium hydroxide.
3. The use according to claim 1, characterized in that in step 3) the G1.0 is 0.3 to 3% by mass and the catalyst is 0.5 to 2% by mass, based on 100% by mass of the total of the G1.0, the catalyst, the ethylene oxide and the propylene oxide.
4. The use according to claim 1, wherein the first temperature is 70 to 90 ℃; and/or the second temperature is 85 to 100 ℃; and/or the third temperature is 120 to 135 ℃; and/or said fourth temperature is between 130 and 145 ℃.
5. The use according to claim 1, wherein the time of the first reaction is 4 to 6 hours; and/or
The second reaction time is 18 to 30 hours; and/or
The fourth reaction time is 30 to 60 minutes; and/or
The sixth reaction takes 30 to 60 minutes.
6. The use according to claim 1, wherein G0.5 is purified by distillation under reduced pressure; and/or said G1.0 is obtained by filtering from said second reaction system, washing and drying.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101418230A (en) * | 2007-10-25 | 2009-04-29 | 中国科学院化学研究所 | Crude de-emulsifier and its preparing process |
| CN110452376A (en) * | 2019-07-26 | 2019-11-15 | 长江大学 | A kind of polyamide-amide class dissaving polymer and its preparation method and application |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101418230A (en) * | 2007-10-25 | 2009-04-29 | 中国科学院化学研究所 | Crude de-emulsifier and its preparing process |
| CN110452376A (en) * | 2019-07-26 | 2019-11-15 | 长江大学 | A kind of polyamide-amide class dissaving polymer and its preparation method and application |
Non-Patent Citations (1)
| Title |
|---|
| 袁琴.基于对苯二胺的聚酰胺胺化合物合成及性能研究.《中国优秀硕士学位论文全文数据库 工程科技I辑》.(第7期),B014-121. * |
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