CN112062951B - One-pot catalytic synthesis method for interfacial polymerization of fatty polyamide sulfonamide - Google Patents
One-pot catalytic synthesis method for interfacial polymerization of fatty polyamide sulfonamide Download PDFInfo
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Abstract
The invention relates to a catalytic synthesis method of fatty polyamide sulfonamide interfacial polymerization by one pot, which comprises the following steps: under the protection of sufficient nitrogen at normal pressure, adding deionized water in which an aliphatic diamine monomer, a composite catalyst and an acid-binding agent are completely dissolved into a container equipped with a mechanical stirring device, and dropwise adding an organic solvent in which 3-chlorosulfonyl benzoyl chloride monomer with the amount of Jie Maer is slightly excessive while continuously stirring; and after dropwise adding for 10-15min, reacting at 0~5 ℃ for 25-45min, then reacting at 25-40 ℃ for 2-4h, and after the reaction is finished, alternately washing the obtained product with boiled deionized water and absolute ethyl alcohol for 3~5 times, and performing vacuum drying to obtain the aliphatic polyamide sulfonamide polymer. The method has simple process and easy implementation, and the obtained aliphatic polyamide sulfamide polymer has good thermal stability, friction performance and solvent resistance, and can be used as a potential membrane material for reverse osmosis, ultrafiltration and the like and a solid lubricating and special engineering material.
Description
Technical Field
The invention relates to the field of functional polymer materials, in particular to a catalytic synthesis method of fatty polyamide sulfonamide interfacial polymerization in one pot.
Background
Polyamides (PA), also commonly known as nylons, refer to a class of polymeric materials having amide groups in the repeat units of the main chain. In 1931, the polyamide was developed and commercialized by the institute of central research, dupont, w.h. carother, and the first polyamide patent, u.s.pat.2130948, was filed. The polyamide has excellent mechanical property and electrical property, wear resistance, solvent resistance, oil resistance, self-lubricating property and good processing property, is a preferred engineering material at present, derives a plurality of modified functional materials, and becomes an indispensable structural material in the industries of automobiles, electronic and electrical products, aerospace, weaponry and the like.
Polysulfonamide (PAS) refers to a polymer whose main chain is composed of repeating units of sulfonamide bonds, and has high strength, high elasticity, good mechanical properties and thermal stability. In addition, polysulfonamides have good stability under acidic and basic conditions, are widely used in the field of dyestuffs, and can also be used for dyeing a large number of products, such as plastics, fibers, films, emollients, skin creams or lotions, polishes, and the like. With regard to polysulfonamides, typical patents at home and abroad are: U.S. patents U.S. Pat. No. 2994693, U.S. Pat. No. 3403200, chinese patent CN97199122.7 and document s.a.sundet, w.a.murphey, journal of Polymer science.1959, vol.xl,389-397 disclose polysulfonamides synthesized from disulfonyl chloride, which are widely used mainly in the dye industry.
Polyamide sulfonamides are polymers that contain amide groups and sulfonamide groups in the main chain. In polymer communication, published by w.h. chan et al, at page 501, 32 th: synthesis and Characterization of reverse Osmosis polyamide sulfonamide Membrane Materials as Potential application values with the Potential of Material for Use as Membrane Materials in Revrse osmoses Applications, polymer communications, the polyamide sulfonamides were synthesized for the first time by first preparing a diamine monomer containing a sulfonamide linkage and then reacting with a bisacylchloride monomer to obtain a Polymer. Chan et al subsequently published article in polymer journal No. 34, page 4377: the excellent Performance of polyamide sulfonamides as Reverse Osmosis membrane materials is reported in detail in the Synthesis, characterization and Reverse Osmosis membrane applications (polymers), and the results confirm that the polymers of sulfonamide groups are important Reverse Osmosis membrane materials. In addition, liang Xuemei and the like also prepare polyamide sulfonamide ultrafiltration membranes for oil-water separation, the membrane materials have the characteristics of good holding power, high reflux rate and the like, have good performance compared with the membrane materials such as polysulfonamide, polyether amine and the like, and can be used for removing oil from oily wastewater (journal of university of eastern science and technology, 1999, 25 (3): 394-397.). The general process for the synthesis of aromatic polyamide sulfonamides is illustrated in greater detail in patent 201310275603.8, and the polyamide sulfonamides synthesized by this process have a relatively low molecular weight and the thermal properties are not optimal.
The fluorine-containing polyamide sulfonamide polymer refers to a polymer containing fluorine, amide groups and sulfonamide group repeated functional groups in a main chain, the polymer is obtained by ring-opening isomerization of fluorine-containing or fluorine-containing beta-sultone through interfacial or solution polymerization, and fluorine is introduced into polyamide sulfonamide to improve chemical resistance and biological resistance of the polyamide sulfonamide, and the polymer is also a potential reverse osmosis membrane material, such as 200810201014.4.
The polymerization method of polyamide sulfamide mainly comprises solution polymerization and interfacial polymerization. At present, a solution polymerization method is adopted more, and the polyamide sulfonamide polymer synthesized by the diamine monomer containing the sulfonamide group and the diacid chloride monomer has the defects that the preparation step of the diamine monomer containing the sulfonamide group is complicated and the reaction condition is harsh, and meanwhile, the diamine monomer containing the sulfonamide group has low activity and is not easy to react with the dichloride monomer to synthesize the polyamide sulfonamide polymer with high molecular weight; the fluorine-containing polyamide sulfamide needs special reaction conditions, has weak operability, has the defects of low molecular weight, low yield, high cost and the like, thereby limiting the performance and industrial application of the polyamide amine sulfamide.
Disclosure of Invention
The invention aims to solve the technical problem of providing a fatty polyamide sulfamide interfacial polymerization one-pot catalytic synthesis method which is simple in process and easy to implement.
In order to solve the problems, the invention provides a catalytic synthesis method of fatty polyamide sulfamide interfacial polymerization in one pot, which is characterized by comprising the following steps: under the protection of sufficient nitrogen at normal pressure, adding deionized water in which the aliphatic diamine monomer (II), the composite catalyst and the acid-binding agent are completely dissolved into a container equipped with a mechanical stirring device, and dropwise adding an organic solvent in which the 3-chlorosulfonyl benzoyl chloride monomer (I) with the amount of Jie Maer is slightly excessive under continuous stirring; after dropwise adding is finished at 10-15min, reacting at 0~5 ℃ for 25-45min, then reacting at 25-40 ℃ for 2-4h, after the reaction is finished, alternately washing the obtained product with boiled deionized water and absolute ethyl alcohol for 3~5 times, and drying in vacuum to obtain the aliphatic polyamide sulfonamide polymer (III); the molar ratio of the 3-chlorosulfonyl benzoyl chloride monomer to the aliphatic diamine monomer is 1 to 1.2:1; taking the organic solvent as a reference, wherein the concentration of the aliphatic diamine monomer or the 3-chlorosulfonyl benzoyl chloride monomer is 0.01-0.045 mol/L; the volume ratio of the deionized water to the organic solvent is 1:1; the proportion of the 3-chlorosulfonyl benzoyl chloride monomer to the composite catalyst is 1mol:0.8 to 1.2g; the molar ratio of the 3-chlorosulfonyl benzoyl chloride monomer to the acid-binding agent is 1:2 to 2.2.
The synthesis reaction formula is shown as follows:
the main chain structure of the aliphatic polyamide sulfonamide polymer simultaneously contains amide bond repeating units and sulfonamide bond repeating units in a meta position, and the reaction formula is as follows:
three repeat unit arrangements:
r is aliphatic diamine monomer.
The organic solvent is one or more of dichloroethane, chloroform, toluene, o-xylene, p-xylene and m-xylene.
The composite catalyst is prepared by mixing Lewis acid and Lewis base according to the weight ratio of 1: a mixture obtained by uniformly mixing the components in a mass ratio of 0.6 to 0.9; the Lewis acid is one of anhydrous calcium chloride, anhydrous lithium chloride and anhydrous aluminum trichloride; the Lewis base is one of pyridine, 2-methylpyridine and triethylamine.
The structural formula of the aliphatic diamine monomer is shown as
Wherein n = an integer of 3 to 30.
The acid-binding agent is any one of lithium hydroxide, zinc hydroxide, calcium hydroxide and aluminum hydroxide.
Dissolving the aliphatic polyamide sulfamide polymer in N, N-dimethylformamide, alternately washing with boiled deionized water and absolute ethyl alcohol for 3~5 times, and vacuum drying to obtain the refined aliphatic polyamide sulfamide polymer.
The stirring speed is 250 to 380r/min.
The vacuum drying condition refers to the temperature of 100 ℃ and the time of 24 hours.
Compared with the prior art, the invention has the following advantages:
1. the 3-chlorosulfonyl benzoyl chloride is a dichlorine monomer, and is subjected to interfacial polymerization and aliphatic diamine monomer one-pot catalytic reaction under the action of a composite catalyst to prepare a polymer containing amide and sulfonamide groups in the structure, and the effective control of the molecular weight of the polymer is realized by adjusting the monomer ratio, compounding the catalyst, and terminating the polymer chain growth by changing the polymerization reaction time and temperature and changing the molar weight of one of the reaction monomers.
The structure of the aliphatic polyamide sulfonamide polymer of the present invention was infrared-analyzed using a Nexus 870 infrared spectrometer (Nicolet, USA) as shown in FIG. 1. As can be seen from the figure: at 1645 cm -1 The C = O (amide I band) stretching vibration absorption peak of carbonyl group, 1544 cm, appears -1 Is a stretching vibration absorption peak of C-N (amide II band), indicates that the polymerization reaction generates amide bond, and is 1320 cm -1 sulfonamide-SO is present 2 N-symmetrical stretching vibration absorption Peak, 1172 cm -1 Is sulfonamide-SO 2 The asymmetric stretching vibration absorption peak of N-indicates that the polymerization reaction generates sulfonamide bond, 3282 cm -1 And 1750 cm -1 2937 cm, a characteristic absorption peak of the benzene ring -1 And 2856 cm -1 Is a characteristic absorption peak of hexamethylenediamine.
The structure of the polymer was tested using a model Bruker Avance III 400 MHz NMR with Autosampler (Bruker, switzerland) nuclear magnetic resonance apparatus, as shown in FIG. 2. The chemical shift is 8.10, the aromatic proton between carbonyl and sulfuryl on the benzene ring, and the other three proton peaks on the benzene ring are respectively 7.68 to 7.84. The chemical shifts of active hydrogen (-NH-) bonded to the nitrogen of the amide group and the sulfonamide group were 8.21 and 8.69, respectively, and the-NH-groups on both amide groups originated from the aliphatic diamine monomers participating in the polycondensation reaction, confirming the presence of N element in the main chain of the polymer and the occurrence of the polymerization reaction. The chemical shift of the deuterated reagent is about 2.5, and the chemical shift of the residual water is about 3.3 to 3.5.
2. Because the polymerized dichloromonomer is a benzene ring rigid monomer and the aliphatic diamine monomer is a flexible monomer, the obtained aliphatic polyamide sulfamide polymer integrates the performances of polyamide and polysulfonamide, has both rigidity and flexibility, has good thermal stability, friction performance and solvent resistance, and can be used as a potential membrane material for reverse osmosis, ultrafiltration and the like and a solid lubrication and special engineering material.
The method comprises the following steps of: thermogravimetric analysis (TGA) of the fatty polyamide sulfonamides was carried out with a synchronous thermal analyzer model STA449F3 (NETZSCH, germany), with the following detection conditions: under the protection of 20ml/min nitrogen, the heating rate is 10 ℃/min, and the temperature range is 25 to 600 ℃. The results are shown in FIG. 4, where the temperature was 362 ℃ at 5% weight loss, indicating that the aliphatic polyamide sulfonamides of the present invention have better heat resistance.
The friction performance is as follows: the friction performance of the aliphatic polyamide sulfamide composite molybdenum disulfide solid lubricating coating is characterized by adopting a CSM friction wear tester (a ball disc type friction tester, antonPasteur corporation, USA). The experimental conditions are as follows: steel ball 6 mm, amplitude 2.5 cm, velocity 10 cm/s, load 5N. As shown in fig. 5, the results show that: the friction coefficient is 0.101, and the friction distance is 300 meters, which shows that the aliphatic polyamide sulfamide composite coating has better friction performance.
Solvent resistance: the solubility of the aliphatic polyamide sulfonamide was examined under 12-hour ultrasonic shaking at room temperature. As shown in Table 1, the aliphatic polyamide sulfonamide is soluble in polar aprotic organic solvents such as N, N-dimethylformamide, N-dimethylacetamide, etc., and exhibits good solubility, which also facilitates the polymer processing such as casting, coating to form a film, or other possible mechanical processing, and furthermore, the solubility behavior is similar to that of polyamide and polysulfonamide, and is soluble in strong acids such as concentrated sulfuric acid, etc., and the sulfonamide of aliphatic polyamide contains sulfonamide groups that are acidic and are soluble in pyridine. Therefore, the aliphatic polyamide sulfamide has good solvent resistance.
TABLE 1 results of fatty Polyamide sulfonamide solubility experiments
3. The number average molecular weight of the aliphatic polyamide sulfonamide polymer obtained by the invention is measured by a Gel Permeation Chromatography (GPC) instrument (Waters 1515 model of Waters company, USA), the mobile phase is N, N-Dimethylformamide (DMF), the flow rate is 50 muL/min, the testing temperature is 35 ℃, and the standard sample is polymethyl methacrylate (PMMA); elution time as determined by GPC in relation to signal intensity. The results are shown in table 2 and fig. 3. It can be found that: the peak molecular weight (Mp) of the aliphatic polyamide sulfonamide was 4.18X 10 5 Number average molecular weight (Mn) of 3.59X 10 5 Weight average molecular weight (Mw) 4.01X 10 5 Molecular weight distribution PDI =1.12. The molecular weight distribution PDI of the series of aliphatic polyamide sulfamide polymers is between 1.03 and 1.21, the molecular weight distribution is uniform, the quality is good, the purity is high, and the aliphatic polyamide sulfamide polymers can obtain the aliphatic polyamide sulfamide with high molecular weight.
TABLE 2 number average molecular weight of the polymer as measured by Gel Permeation Chromatography (GPC)
4. The method has simple process and easy implementation, and the yield of the obtained aliphatic polyamide sulfamide polymer can reach more than 89%.
Drawings
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
FIG. 1 is an IR spectrum of a fatty polyamide sulfonamide polymer of the present invention.
FIG. 2 is a nuclear magnetic spectrum of the aliphatic polyamide sulfonamide polymer of the present invention.
FIG. 3 is a gel permeation chromatogram of a fatty polyamide sulfonamide polymer of the invention.
FIG. 4 is a thermogravimetric plot of the aliphatic polyamide sulfonamide polymer of the present invention.
FIG. 5 is a graph showing the friction properties of the aliphatic polyamide sulfonamide polymer according to the present invention.
Detailed Description
Embodiment 1 a catalytic synthesis method of aliphatic polyamide sulfonamide interfacial polymerization in one pot:
under the protection of sufficient nitrogen at normal pressure, adding deionized water in which an aliphatic diamine monomer, a composite catalyst and an acid-binding agent are completely dissolved into a container equipped with a mechanical stirring device, and dropwise adding an organic solvent for dissolving 3-chlorosulfonyl benzoyl chloride monomer with a slightly excessive amount of Jie Maer under the continuous stirring at a stirring speed of 250 r/min; after dropwise adding is finished within 10-15min, reacting at 0 ℃ for 45min, then reacting at 25 ℃ for 4h, stopping the reaction until the PH of the reaction solution is approximately equal to 7.25, and separating out a white polymer in the solution. After the reaction is finished, the obtained product is alternately washed for 3 times by boiled deionized water and absolute ethyl alcohol in sequence, and then is dried for 24 hours in vacuum at 100 ℃ to obtain the aliphatic polyamide sulfamide polymer, wherein the yield is 89.53%.
Wherein: the mol ratio of the 3-chlorosulfonyl benzoyl chloride monomer to the aliphatic diamine monomer is 1:1; the concentration of the aliphatic diamine monomer or the 3-chlorosulfonyl benzoyl chloride monomer is 0.01mol/L based on the organic solvent; the volume ratio of the deionized water to the organic solvent is 1:1; the proportion of the 3-chlorosulfonyl benzoyl chloride monomer to the composite catalyst is 1mol:0.8g; the mol ratio of the 3-chlorosulfonyl benzoyl chloride monomer to the acid-binding agent is 1:2.
the composite catalyst is prepared by mixing Lewis acid and Lewis base according to the weight ratio of 1: the resulting mixture was uniformly mixed at a mass ratio of 0.6.
Embodiment 2 a catalytic synthesis method of aliphatic polyamide sulfonamide interfacial polymerization in one pot:
under the protection of sufficient nitrogen at normal pressure, adding deionized water in which an aliphatic diamine monomer, a composite catalyst and an acid-binding agent are completely dissolved into a container equipped with a mechanical stirring device, and dropwise adding an organic solvent for dissolving 3-chlorosulfonyl benzoyl chloride monomer with a slightly excessive amount of Jie Maer under the continuous stirring at a stirring speed of 380 r/min; after dropwise adding is finished within 10-15min, reacting at 5 ℃ for 25min, then reacting at 40 ℃ for 2h, stopping the reaction until the PH of the reaction solution is approximately equal to 7.25, and separating out a white polymer in the solution. After the reaction is finished, the obtained product is alternately washed for 5 times by boiled deionized water and absolute ethyl alcohol in sequence, and then is dried for 24 hours in vacuum at 100 ℃ to obtain the aliphatic polyamide sulfamide polymer, wherein the yield of the aliphatic polyamide sulfamide polymer is 90.81 percent.
Wherein: the mol ratio of the 3-chlorosulfonyl benzoyl chloride monomer to the aliphatic diamine monomer is 1.2:1; taking an organic solvent as a reference, wherein the concentration of the aliphatic diamine monomer or the 3-chlorosulfonyl benzoyl chloride monomer is 0.045mol/L; the volume ratio of the deionized water to the organic solvent is 1:1; the proportion of the 3-chlorosulfonyl benzoyl chloride monomer to the composite catalyst is 1mol:1.2g; the mol ratio of the 3-chlorosulfonyl benzoyl chloride monomer to the acid-binding agent is 1:2.2.
the composite catalyst is prepared by mixing Lewis acid and Lewis base according to the weight ratio of 1:0.9 mass ratio was mixed to obtain a homogeneous mixture.
Embodiment 3 a catalytic synthesis method of aliphatic polyamide sulfonamide interfacial polymerization in one pot:
under the protection of sufficient nitrogen at normal pressure, adding deionized water in which an aliphatic diamine monomer, a composite catalyst and an acid-binding agent are completely dissolved into a container equipped with a mechanical stirring device, and dropwise adding an organic solvent for dissolving 3-chlorosulfonyl benzoyl chloride monomer with a slightly excessive amount of Jie Maer under the continuous stirring at a stirring speed of 300 r/min; after dropwise adding is finished within 10-15min, reacting at 2 ℃ for 35min, then reacting at 30 ℃ for 3h, stopping the reaction until the PH of the reaction solution is approximately equal to 7.25, and separating out a white polymer in the solution. After the reaction is finished, the obtained product is alternately washed for 4 times by boiled deionized water and absolute ethyl alcohol in sequence, and then is dried for 24 hours in vacuum at 100 ℃ to obtain the aliphatic polyamide sulfamide polymer, wherein the yield is 92.78%.
Wherein: the mol ratio of the 3-chlorosulfonyl benzoyl chloride monomer to the aliphatic diamine monomer is 1.1:1; the concentration of the aliphatic diamine monomer or the 3-chlorosulfonyl benzoyl chloride monomer is 0.025mol/L based on the organic solvent; the volume ratio of the deionized water to the organic solvent is 1:1; the proportion of the 3-chlorosulfonyl benzoyl chloride monomer to the composite catalyst is 1mol:1.0g; the mol ratio of the 3-chlorosulfonyl benzoyl chloride monomer to the acid-binding agent is 1:2.1.
the composite catalyst is prepared by mixing Lewis acid and Lewis base according to the weight ratio of 1: the resulting mixture was uniformly mixed at a mass ratio of 0.8.
In example 1~3, the structural formula of the aliphatic diamine monomer is
Wherein n = an integer of 3 to 30.
The organic solvent is one or more of dichloroethane, chloroform, toluene, o-xylene, p-xylene and m-xylene.
The Lewis acid is one of anhydrous calcium chloride, anhydrous lithium chloride and anhydrous aluminum trichloride; the Lewis base is one of pyridine, 2-methylpyridine and triethylamine.
The acid-binding agent is any one of lithium hydroxide, zinc hydroxide, calcium hydroxide and aluminum hydroxide.
In 1~3 above, if refining is needed, the aliphatic polyamide sulfonamide polymer is dissolved in N, N-dimethylformamide, then sequentially washed with boiled deionized water and absolute ethanol for 3~5 times, and vacuum dried at 100 ℃ for 24 hours to obtain the refined aliphatic polyamide sulfonamide polymer.
Claims (4)
1. A catalytic synthesis method of fatty polyamide sulfamide interfacial polymerization in one pot is characterized in that: under the protection of sufficient nitrogen at normal pressure, deionized water in which the aliphatic diamine monomer, the composite catalyst and the acid-binding agent are completely dissolved is added into a container provided with a mechanical stirring deviceContinuously stirring and dropwise adding an organic solvent for dissolving the 3-chlorosulfonyl benzoyl chloride monomer; after dropwise adding is finished for 10-15min, reacting at 0~5 ℃ for 25-45min, then reacting at 25-40 ℃ for 2-4h, after the reaction is finished, alternately washing the obtained product with boiled deionized water and absolute ethyl alcohol for 3~5 times, and carrying out vacuum drying to obtain the aliphatic polyamide sulfamide polymer; the molecular weight distribution PDI of the obtained series of aliphatic polyamide sulfamide polymers is between 1.03 and 1.21, and the molecular weight distribution is relatively uniform; the molar ratio of the 3-chlorosulfonyl benzoyl chloride monomer to the aliphatic diamine monomer is 1 to 1.2:1; taking the organic solvent as a reference, wherein the concentration of the aliphatic diamine monomer or the 3-chlorosulfonyl benzoyl chloride monomer is 0.01-0.045 mol/L; the volume ratio of the deionized water to the organic solvent is 1:1; the proportion of the 3-chlorosulfonyl benzoyl chloride monomer to the composite catalyst is 1mol:0.8 to 1.2g; the molar ratio of the 3-chlorosulfonyl benzoyl chloride monomer to the acid-binding agent is 1:2 to 2.2; the organic solvent is one or more of dichloroethane, chloroform, toluene, o-xylene, p-xylene and m-xylene; the composite catalyst is prepared by mixing Lewis acid and Lewis base according to the weight ratio of 1: a mixture obtained by uniformly mixing the components in a mass ratio of 0.6 to 0.9; the Lewis acid is one of anhydrous calcium chloride, anhydrous lithium chloride and anhydrous aluminum trichloride; the Lewis base is one of pyridine, 2-methylpyridine and triethylamine; the structural formula of the aliphatic diamine monomer is H 2 N(CH 2 ) n NH 2 Wherein n = an integer of 3 to 30; the acid-binding agent is any one of lithium hydroxide, zinc hydroxide, calcium hydroxide and aluminum hydroxide.
2. The interfacial polymerization one-pot catalytic synthesis method of fatty polyamide sulfonamide according to claim 1, characterized in that: dissolving the aliphatic polyamide sulfamide polymer in N, N-dimethylformamide, alternately washing with boiled deionized water and absolute ethyl alcohol for 3~5 times, and vacuum drying to obtain the refined aliphatic polyamide sulfamide polymer.
3. The interfacial polymerization one-pot catalytic synthesis method of fatty polyamide sulfonamide according to claim 1, characterized in that: the stirring speed is 250 to 380r/min.
4. The interfacial polymerization one-pot catalytic synthesis method of fatty polyamide sulfonamide according to claim 1 or 2, characterized in that: the vacuum drying condition refers to the temperature of 100 ℃ and the time of 24 hours.
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| CN101367938A (en) * | 2008-10-10 | 2009-02-18 | 张永明 | Novel fluorine-containing polyamide sulfonylamine polymer and preparation method thereof |
| CN103342812A (en) * | 2013-07-01 | 2013-10-09 | 大连工业大学 | Aromatic polyamide sulfamide and preparation method thereof |
| CN111647160A (en) * | 2020-06-24 | 2020-09-11 | 崔国英 | Aromatic polyamide sulfonamide polymer, positive photosensitive composition containing aromatic polyamide sulfonamide polymer, and use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101367938A (en) * | 2008-10-10 | 2009-02-18 | 张永明 | Novel fluorine-containing polyamide sulfonylamine polymer and preparation method thereof |
| CN103342812A (en) * | 2013-07-01 | 2013-10-09 | 大连工业大学 | Aromatic polyamide sulfamide and preparation method thereof |
| CN111647160A (en) * | 2020-06-24 | 2020-09-11 | 崔国英 | Aromatic polyamide sulfonamide polymer, positive photosensitive composition containing aromatic polyamide sulfonamide polymer, and use thereof |
Non-Patent Citations (1)
| Title |
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| Preparation of novel poly(amide-sulfonamide) (PASA) and its application in 2,4-dinitrophenol adsorption;Lin Jia et al.,;《Designed Monomers and Polymers》;20141231;第17卷(第5期);第425-429页 * |
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