CN111039817A - Method for recovering solvent in polyimide preparation process - Google Patents
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- CN111039817A CN111039817A CN201911087082.7A CN201911087082A CN111039817A CN 111039817 A CN111039817 A CN 111039817A CN 201911087082 A CN201911087082 A CN 201911087082A CN 111039817 A CN111039817 A CN 111039817A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/36—Accumulators not provided for in groups H01M10/05-H01M10/34
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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- Y02E60/10—Energy storage using batteries
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Abstract
The application discloses a method for recovering a solvent in a preparation process of polyimide serving as a cathode material of a water-based lithium ion battery, which comprises the following steps of: filtering waste liquid generated in the polyimide preparation process to obtain filtrate A; adding a drying agent into the filtrate A, mixing and filtering to obtain a filtrate B; adding the adsorbent into the filtrate B, mixing, and filtering to obtain a filtrate C; standing and layering the filtrate C, and collecting the lower layer which is the recovered solvent. The solvent recovery method is simpler and more economic, has the advantages of simple operation steps, low cost and the like, is very suitable for recovering the solvent of the reaction, realizes the cyclic utilization of the solvent, and is economical, practical, green and environment-friendly.
Description
Technical Field
The application relates to a method for recovering a solvent in a preparation process of polyimide serving as a cathode material of a water-based lithium ion battery, belonging to the field of waste liquid treatment.
Background
Lithium ion batteries have been widely recognized since the end of the 20 th century due to the advantages of high energy density and high voltage, and have now taken a leading role in the consumer electronics market and in the new energy automobile power battery industry. Polyimide is a novel material with high temperature resistance, wear resistance, radiation resistance and good dielectric property, can be used as coating, enameled wire, adhesive, plastic, lunch box, medical apparatus and the like, and is widely applied to national defense industry, aviation, atomic energy industry, electronic industry and other technical equipment. Polyimide-based organic materials have been demonstrated to work in aqueous lithium ion batteries and aqueous flow batteries, each with parameters not inferior to those of conventional batteries and exhibiting some very good properties due to the fact that the electrolyte is an aqueous solution.
In the synthesis process of polyimide materials, a large amount of solvents are needed, the cost is high, the environmental protection is not facilitated, the future industrial development is not facilitated, and the recovery and reutilization of the solvents are necessary in the long run. At present, the recovery of the reaction solvent is mostly based on a series of processes such as distillation and condensation, and the processes are complicated, and the types of the applied equipment are many, so that the treatment cost is high, and therefore, the recovery is not an optimal choice. Therefore, a method for recovering the solvent in the preparation process of polyimide materials is urgently needed to realize the recycling of the solvent.
Disclosure of Invention
According to one aspect of the application, a solvent recovery and treatment method is provided, which is simpler and more economical, and has the advantages of simple operation steps, low cost and the like.
The solvent recovery and treatment method comprises the following steps:
step A: filtering waste liquid generated in the polyimide preparation process to obtain filtrate A;
and B: adding a drying agent into the filtrate A, mixing and filtering to obtain a filtrate B;
and C: adding the adsorbent into the filtrate B, mixing, and filtering to obtain a filtrate C;
step D: standing and layering the filtrate C, and collecting the lower layer which is the recovered solvent.
Optionally, the drying agent is at least one selected from phosphorus pentoxide, anhydrous sodium sulfate, anhydrous calcium chloride, anhydrous magnesium sulfate, allochroic silica gel, activated alumina, anhydrous calcium sulfate, anhydrous potassium carbonate and calcium oxide.
Optionally, the adsorbent is selected from at least one of activated carbon, silica gel, molecular sieve, natural clay, polymeric adsorbent.
Preferably, the molecular sieve is a zeolite molecular sieve or a carbon molecular sieve.
Preferably, the polymeric adsorbent is polyacrylamide.
Optionally, the mass-to-volume ratio of the drying agent to the filtrate A is 5-10 g/100 mL.
Optionally, the mass-to-volume ratio of the adsorbent to the filtrate B is 5-10 g/100 mL.
Alternatively, the mixing in step B and step C is by stirring followed by sonication.
Optionally, the stirring time is 5-10 min, and the ultrasonic time is 10-30 min.
Optionally, the waste liquid comprises at least one of polyimide, polyimide monomer, and N-dimethylformamide.
Alternatively, the polyimide monomer comprises at least one compound represented by formula I and at least one compound represented by formula II;
optionally, the polyimide is selected from at least one of the compounds represented by formula III;
H2N-R-NH2formula II
Wherein Ar is selected from at least one of aryl of C6-C20 and heteroaryl of C4-C20;
r is at least one selected from C2-C5 alkylidene, C6-C20 aryl and C4-C20 heteroaryl;
n＝1000～10000。
optionally, Ar is selected from at least one of aryl of C10-C20 and heteroaryl of C10-C20.
Alternatively, Ar is naphthyl.
Optionally, R is selected from at least one of C2-C4 alkylene.
Optionally, the polyimide preparation process comprises the following steps:
reacting a solution containing a polyimide monomer for 4-6 hours at 120-180 ℃ in an inactive atmosphere, and separating to obtain a waste liquid and a product;
the polyimide monomer comprises at least one compound shown as a formula I and at least one compound shown as a formula II;
the polyimide is selected from at least one of compounds shown in a formula III;
the solvent in the solution containing the polyimide monomer is at least one selected from N-methyl pyrrolidone and N-dimethyl formamide.
Optionally, the molar ratio of the compound shown in the formula I to the compound shown in the formula II in the polyimide monomer is 1: 1-1: 1.1.
Alternatively, the compound of formula I is 1,4,5, 8-naphthalenetetracarboxylic anhydride.
Alternatively, the compound of formula II is ethylenediamine.
According to another aspect of the present application, there is provided a use of the solvent recovered by the solvent recovery method according to one aspect of the present application in the synthesis of an aqueous ion battery electrode material. .
Specifically, the solvent recovery method comprises the following steps:
step A: and (3) placing supernatant obtained after a final product is obtained by centrifugation in the preparation process of the cathode material polyimide of the water-based lithium ion battery in a dry beaker, then filtering by using a sand core funnel, and removing solid impurities which are not separated during centrifugation to obtain filtrate A.
Step B, measuring 150ml of the filtrate A, and pouring the filtrate A into a clean beaker; 10g of phosphorus pentoxide (P) are weighed2O5) Powder of then P2O5Adding the mixture into a recovered solvent, uniformly stirring, ultrasonically dispersing for 10-30 min, filtering, and removing P absorbed with water2O5Obtaining filtrate B.
And C: measuring 120ml of filtrate B, and pouring into a clean beaker; weighing 5g of activated carbon powder, adding activated carbon into the filtrate B, uniformly stirring, ultrasonically dispersing for 10-30 min to enable the system to generate heat, cooling and standing for 1h, stirring, filtering, and removing the activated carbon full of solid impurities to obtain filtrate C.
Step D: pouring all the filtrate C into a clean separating funnel; standing for layering to obtain lower layer which is N, N-Dimethylformamide (DMF) or N-methylpyrrolidone (NMP) solvent for material synthesis, and slowly discharging from the lower end of the funnel for collection.
The beneficial effects that this application can produce include:
1) the solvent recovery method provided by the application can enable the recovered solvent to be reused for material synthesis without affecting the relevant performance of the material through simple treatment, the recovery process is simple in operation steps and low in cost, is very suitable for solvent recovery of the reaction, realizes recycling of the solvent, and is economical, practical, green and environment-friendly;
2) the recovered solvent provided by the solvent recovery method is directly used for synthesizing the obtained material without any treatment, the specific capacity of the manufactured battery is low, but the cycling stability is good, and the recovered solvent is treated by the method and then used for synthesizing the material again, so that the same effect as that of a fresh solvent is obtained;
3) the solvent recovery method has the advantages that the used medicines and instruments are cheap and easy to obtain, the operation steps are very simple, and the production cost of materials can be greatly reduced.
Drawings
FIG. 1 shows an IR spectrum of a negative electrode material prepared from fresh solvent (material ① -1), a negative electrode material prepared from untreated waste liquid (material ② -1), and a negative electrode material prepared from solvent (material ③ -1) recovered in example 1 of the present application before sintering;
FIG. 2 shows the IR spectra of the sintered negative electrode material prepared from fresh solvent (material ① -2), the untreated waste liquid (material ② -2) and the solvent recovered from example 1 of the present application (material ③ -2);
FIG. 3 is a graph of the specific capacity (a) and cycling stability (b) of a battery made with a negative electrode material (material ① -2) prepared with fresh solvent;
FIG. 4 shows the specific capacity (c) and cycling stability (d) of a battery made of the negative electrode material (material ② -2) prepared from untreated waste liquid;
fig. 5 shows specific capacity (e) and cycle stability (f) of a battery fabricated from the negative electrode material (material ③ -2) prepared from the solvent recovered in example 1 of the present application.
Detailed Description
The present application will be described in detail with reference to examples, but the present application is not limited to these examples.
The raw materials in the examples of the present application were all purchased commercially, unless otherwise specified.
The analysis method in the examples of the present application is as follows:
electrical performance analysis was performed using a battery tester (model: CT-4008-5V20 Ma-164).
Infrared spectroscopy was performed using a Fourier transform infrared spectrometer (model: (Thermo) Is50 FT-IR).
Example 1 solvent recovery treatment
Step A: and (3) placing supernatant obtained after a final product is obtained by centrifugation in the preparation process of the cathode material polyimide of the water-based lithium ion battery in a dry beaker, then filtering by using a sand core funnel, and removing solid impurities which are not separated during centrifugation to obtain filtrate A.
And B: measuring 150ml of the filtrate A, and pouring into a clean beaker; 10g of phosphorus pentoxide (P) are weighed2O5) Powder of then P2O5Adding into recovered solvent, stirring, ultrasonic dispersing for 10min, filtering, and removing water-absorbed P2O5Obtaining filtrate B.
And C: measuring 120ml of filtrate B, and pouring into a clean beaker; weighing 5g of activated carbon powder, adding activated carbon into the filtrate B, uniformly stirring, ultrasonically dispersing for 10min to enable the system to generate heat, cooling and standing for 1h, stirring, filtering, and removing the activated carbon full of solid impurities to obtain filtrate C.
Step D: pouring all the filtrate C into a clean separating funnel; standing for layering to obtain lower layer of DMF solvent for material synthesis, and slowly discharging from the lower end of the funnel.
Example 2 solvent recovery treatment
The conditions and the operation steps were the same as in example 1 except that phosphorus pentoxide was replaced with anhydrous sodium sulfate in step B and activated carbon was replaced with silica gel in step C.
Example 3 solvent recovery treatment
The conditions and operating procedure were the same as in example 1 except that the phosphorus pentoxide was replaced by anhydrous calcium chloride in step B and the activated carbon was replaced by zeolite molecular sieve in step C.
Example 4 solvent recovery treatment
The conditions and the operation procedure were the same as in example 1 except that phosphorus pentoxide was replaced by anhydrous magnesium sulfate in step B and activated carbon was replaced by a carbon molecular sieve in step C.
Example 5 solvent recovery treatment
The conditions and the operation steps were the same as those in example 1 except that phosphorus pentoxide in step B was replaced with allochroic silica gel and activated carbon in step C was replaced with carbon molecular sieve.
Example 6 solvent recovery treatment
The conditions and operating procedure were the same as in example 1 except that the phosphorus pentoxide in step B was replaced by activated alumina and the activated carbon in step C was replaced by zeolite molecular sieve.
Example 7 solvent recovery treatment
The conditions and operating procedure were the same as in example 1 except that the phosphorus pentoxide was replaced with anhydrous calcium sulfate in step B.
Example 8 solvent recovery treatment
The conditions and the operation procedure were the same as in example 1 except that phosphorus pentoxide was replaced by anhydrous magnesium sulfate in step B and activated carbon was replaced by a carbon molecular sieve in step C.
Example 9 solvent recovery treatment
The conditions and the operation procedure were the same as in example 1 except that the phosphorus pentoxide in step B was replaced with anhydrous potassium carbonate and the activated carbon in step C was replaced with a carbon molecular sieve.
Example 10 solvent recovery treatment
The conditions and the procedure were the same as in example 1 except that the phosphorus pentoxide was replaced by calcium oxide in step B.
Example 11 solvent recovery treatment
Step A: and (3) placing supernatant obtained after a final product is obtained by centrifugation in the preparation process of the cathode material polyimide of the water-based lithium ion battery in a dry beaker, then filtering by using a sand core funnel, and removing solid impurities which are not separated during centrifugation to obtain filtrate A.
And B: measuring 150ml of the filtrate A, and pouring into a clean beaker; weighing 10g of phosphorus pentoxide powder, adding the phosphorus pentoxide into the recovered solvent, uniformly stirring, ultrasonically dispersing for 30min, filtering, and removing the phosphorus pentoxide absorbed with water to obtain filtrate B.
And C: measuring 120ml of filtrate B, and pouring into a clean beaker; weighing 5g of activated carbon powder, adding activated carbon into the filtrate B, uniformly stirring, ultrasonically dispersing for 30min to enable the system to generate heat, cooling and standing for 1h, stirring, filtering, and removing the activated carbon full of solid impurities to obtain filtrate C.
Step D: pouring all the filtrate C into a clean separating funnel; standing until layering, wherein the lower layer is NMP solvent for material synthesis, and slowly discharging from the lower end pipe orifice of the funnel for collection.
Example 12 Synthesis of negative electrode Material
Step A: fresh DMF was first added to a 1000ml round bottom flask, then mixed in a molar ratio of 1:1.1 add 1,4,5, 8-naphthalene tetracarboxylic anhydride (NTCDA) and Ethylenediamine (EDA), argon shield, keep magnetic stirring, spherical condenser reflux. And gradually heating up to 150 ℃ in steps. Reflux at this temperature for 4 h.
And step B, collecting the generated product, washing and centrifuging, removing supernatant, diluting and cleaning the lower-layer centrifugal precipitate with DMF, centrifuging for the second time, washing and centrifuging twice with ethanol, wherein the lower-layer solid is a synthesized material, and finally drying the material in a vacuum oven at 90 ℃ to obtain dry powder, namely the material ① -1.
And step C, sintering the dry powder in a tube furnace under the protection of argon atmosphere for 8 hours at the sintering temperature of 350 ℃, and marking the sintered material as a material ① -2.
Example 13 Synthesis of negative electrode Material
The same procedure as in example 12 was conducted except that the waste liquid obtained in example 12 was reused for the synthesis of a material without any treatment, and the obtained dry powder was designated as material ② -1, and the sintered material was designated as material ② -2.
Example 14 Synthesis of negative electrode Material
The same procedure as in example 12 was repeated except that material synthesis was carried out again using the DMF solvent recovered in example 1 to obtain dry powder designated as material ③ -1 and the material after sintering designated as material ③ -2.
Example 15 Synthesis of negative electrode Material
Step A: fresh NMP was first added to a 1000ml round bottom flask and then mixed in a molar ratio of 1:1.1 add 1,4,5, 8-naphthalene tetracarboxylic anhydride (NTCDA) and Ethylenediamine (EDA), argon shield, keep magnetic stirring, spherical condenser reflux. And gradually heating up to 150 ℃ in steps. Reflux at this temperature for 6 h.
And B: the resultant product was collected, washed and centrifuged, and the supernatant was removed. The lower centrifugation sediment was diluted and washed with NMP and centrifuged for the second time. Then washing and centrifuging twice by using ethanol, wherein the lower layer of solid is the synthesized material. Finally, the material is dried in a vacuum oven at 90 ℃ to obtain dry powder.
And C: and sintering the dry powder in a tube furnace under the protection of argon atmosphere. The sintering time is 8 hours, and the sintering temperature is 350 ℃.
EXAMPLE 16 Assembly of Battery
The structure is as follows: (half cell as an example) electrolyte: 1.5-2.5M lithium sulfate (Li)2SO4) Aqueous solution
A diaphragm: glass fiber filter paper (porosity below 1 micron, thickness about 260 micron)
Negative electrode: activated carbon cloth
And (3) positive electrode: polyimide, polyimide resin composition and polyimide resin composition
The assembling method comprises the following steps: assembly of the battery, comprising:
active substance: polyimide organic material
Conductive agent: conductive carbon black (Super P carbon)
Adhesive: polytetrafluoroethylene (PTFE) emulsion
Current collector: stainless steel net
The process comprises the following steps: mixing and stirring the active substance, the conductive carbon black and the binder in an ethanol solution according to the mass ratio of 6:3:1 to form slurry, coating the slurry on a stainless steel net, and then drying in vacuum. The area of the electrode is about 1-2 cm2The surface density of the active substance is about 1-2 mg cm-2。
The used battery is a CR2032 button battery.
Example 17 Infrared characterization of synthetic materials
Infrared spectrum tests were conducted on materials ① -1, ① -2, ② -1, ② -2, ③ -1 and ③ -2 before and after sintering (with a suffix of 1 for the materials before sintering and a suffix of 2 for the materials after sintering), and typical test results are shown in FIGS. 1 and 2-1，1783cm-1And 1741cm-1There is a clear difference in the wave number for material ② -1 of 1621cm-1Is hardly visible, and has a wave number of 1783cm-1And 1741cm-1Two new small peaks appear; 1783cm after sintering-1And 1741cm-1Small peak still exists at 1621cm-1The peak disappeared at a wave number of 730cm-1The nearby material ② -1 is slightly different from the material ③ -1 and the material ① -1, the material ③ -1 and the material ① -1 are acromion, but the material ② -1 is almost not, so that new impurities appear in the material of the material ② -1, and the new impurities have obvious influence on the specific capacity and the cycle performance of the battery, and therefore, the material obtained by synthesizing the material by using an untreated solvent contains more impurities and is difficult to be used as an electrode material of an aqueous battery, but the material synthesized with the fresh solvent after the treatment of the scheme has no difference.
Example 18 characterization of electrical properties of the cells
Compared with the fresh solvent, the specific capacity and the cycling stability of the battery made of the material obtained when the solvent treated by the scheme is reused for synthesis are basically consistent, about 140mAh/g, the specific capacity of the battery is fluctuated just after nearly 100 cycles, the battery is stable after dozens of cycles, the battery is basically not attenuated, the coulomb efficiency is more than 99%, and the superiority of the solvent recovery treatment scheme is reanalyzed; the specific capacity of the battery corresponding to the solvent without any treatment is reduced by more than ten percent, the specific capacity is about 116mAh/g, but the cycling stability is good.
Although the present application has been described with reference to a few embodiments, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the application as defined by the appended claims.
Claims (10)
1. A solvent recovery and treatment method is characterized by comprising the following steps:
step A: filtering waste liquid generated in the polyimide preparation process to obtain filtrate A;
and B: adding a drying agent into the filtrate A, mixing and filtering to obtain a filtrate B;
and C: adding the adsorbent into the filtrate B, mixing, and filtering to obtain a filtrate C;
step D: standing and layering the filtrate C, and collecting the lower layer which is the recovered solvent.
2. The solvent recovery and treatment method according to claim 1, wherein the drying agent is at least one selected from phosphorus pentoxide, anhydrous sodium sulfate, anhydrous calcium chloride, anhydrous magnesium sulfate, allochroic silica gel, activated alumina, anhydrous calcium sulfate, anhydrous potassium carbonate and calcium oxide;
preferably, the adsorbent is selected from at least one of activated carbon, silica gel, molecular sieve, natural clay and polymer adsorbent;
preferably, the molecular sieve is a zeolite molecular sieve or a carbon molecular sieve;
preferably, the polymeric adsorbent is polyacrylamide.
3. The solvent recovery and treatment method according to claim 1, wherein the mass-to-volume ratio of the drying agent to the filtrate A is 5-10 g/100 mL;
preferably, the mass-volume ratio of the adsorbent to the filtrate B is 5-10 g/100 mL;
preferably, the mixing in step B and step C is by stirring followed by sonication.
4. The solvent recovery and treatment method according to claim 3, wherein the stirring time is 5-10 min, and the ultrasonic time is 10-30 min.
5. The solvent recovery and treatment method according to claim 1, wherein the waste liquid comprises at least one of polyimide, polyimide monomer, water, and N-dimethylformamide.
6. The solvent recovery and processing method as claimed in claim 5, wherein the polyimide monomer comprises at least one compound represented by formula I and at least one compound represented by formula II;
the polyimide is selected from at least one of compounds shown in a formula III;
H2N-R-NH2formula II
Wherein Ar is selected from at least one of aryl of C6-C20 and heteroaryl of C4-C20;
r is at least one selected from C2-C5 alkylidene, C6-C20 aryl and C4-C20 heteroaryl;
n＝1000～10000。
7. the solvent recovery and processing method as claimed in claim 1, wherein the polyimide preparation process comprises the steps of:
reacting a solution containing a polyimide monomer for 4-6 hours at 120-180 ℃ in an inactive atmosphere, and separating to obtain a waste liquid and a product;
the polyimide monomer comprises at least one compound shown as a formula I and at least one compound shown as a formula II;
the polyimide is selected from at least one of compounds shown in a formula III;
the solvent in the solution containing the polyimide monomer is at least one selected from N-methyl pyrrolidone and N-dimethyl formamide.
8. The solvent recovery and treatment method according to claim 7, wherein the molar ratio of the compound represented by formula I to the compound represented by formula II in the polyimide monomer is 1:1 to 1: 1.1.
9. The solvent recovery and processing method as claimed in claim 7, wherein the compound represented by formula I is 1,4,5, 8-naphthalene tetracarboxylic anhydride;
the compound shown in the formula II is ethylenediamine.
10. Use of the solvent recovered by the solvent recovery method according to any one of claims 1 to 9 for the synthesis of an electrode material for an aqueous ion battery.
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Citations (3)
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| CN101460447A (en) * | 2006-05-23 | 2009-06-17 | V.B.医疗保险私人有限公司 | Recovery of dimethylformamide and other solvents from process streams of manufacture of trichlorogalactosucrose |
| CN106883408A (en) * | 2017-03-28 | 2017-06-23 | 万华化学集团股份有限公司 | A kind of preparation method of polyimides |
| CN107936248A (en) * | 2017-11-27 | 2018-04-20 | 长沙新材料产业研究院有限公司 | A kind of preparation method of polyimide resin |
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2019
- 2019-11-08 CN CN201911087082.7A patent/CN111039817A/en active Pending
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| CN101460447A (en) * | 2006-05-23 | 2009-06-17 | V.B.医疗保险私人有限公司 | Recovery of dimethylformamide and other solvents from process streams of manufacture of trichlorogalactosucrose |
| US20090264640A1 (en) * | 2006-05-23 | 2009-10-22 | V.B. Medicare Pvt. Ltd | Recovery of dimethylformamide and other solvents from process streams of manufacture of trichlorogalactosucrose |
| CN106883408A (en) * | 2017-03-28 | 2017-06-23 | 万华化学集团股份有限公司 | A kind of preparation method of polyimides |
| CN107936248A (en) * | 2017-11-27 | 2018-04-20 | 长沙新材料产业研究院有限公司 | A kind of preparation method of polyimide resin |
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