JP3690019B2 - Aromatic polysulfone polymer and process for producing the same - Google Patents

Description

[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an aromatic polysulfone polymer having a poly (alkylamine) residue introduced as a graft group as a side chain, and a method for producing the same, and more specifically, adsorption and separation of ionic substances and physiologically active substances. The present invention relates to a poly (alkylamine) grafted aromatic polysulfone polymer that can be suitably used for fixation and the like, and a method for producing the same.
[0002]
[Prior art]
Conventionally, a specific physiologically active substance or the like immobilized on an insoluble carrier has been widely used as an adsorbent for affinity chromatography, a blood treatment material for treatment, a cell culture device, an antibacterial material, and other analytical reagents. This is an important field where a wider range of applications is expected in the future.
[0003]
Cellulose, agarose, polystyrene and the like have been known for a long time as insoluble carriers, but these exist as insoluble molded products. On the other hand, the aromatic polysulfone polymer has good moldability and can be used as a hollow fiber for dialysis. Therefore, when a functional group exhibiting adsorption ability is introduced, its utility value is high. Therefore, chloromethylated polysulfone {Higuchi et al., J. Appl. Polymer Chem. 46 , 449-457 (1992)}, amidomethylated polysulfone (JP-A-6-50095), etc. have been developed, and research using these as a carrier has begun. .
[0004]
However, the aromatic polysulfone polymer maintains its high mechanical properties due to the cohesive strength of the polymer main chain, so if too many functional groups are introduced into its main chain or side chain, its excellent mechanical properties are It will be lost. On the other hand, if the introduction density of the functional group is too low, there is a dilemma in which the adsorptive capacity is too small to achieve its purpose.
[0005]
[Problems to be solved by the invention]
The present invention is intended to solve such problems of the prior art, and provides a novel polysulfone having a sufficient amount of useful reactive functional groups introduced therein and having high mechanical properties, and a method for producing the same. For the purpose.
[0006]
[Means for Solving the Problems]
In order to achieve the above object, the present invention has the following configuration.
[0007]
“(1) As a side chain functional group, a group represented by the following general formula (I) {wherein E represents a poly (alkylaminoalkylene) group, and R ¹ represents an alkyl group having 1 to 20 carbon atoms. R ² represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R ¹ and R ² may be the same or different.} Coalescence.
[0008]
E—CH (R ¹ ) —CO—NR ² —CH ₂ — (I)
(2) An aromatic polysulfone polymer having a halogen substituent represented by the following general formula (III) (wherein X represents a halogen atom) is reacted with a polyamine compound. 2. A process for producing an aromatic polysulfone polymer according to 1.
[0009]
^{X-CH (R 1) -CO} -N (R 2) -CH 2 - (III) '
[0010]
DETAILED DESCRIPTION OF THE INVENTION
Next, the present invention will be described in detail.
[0011]
The aromatic polysulfone polymer introduced with the group represented by the general formula (I) as a side chain in the present invention (hereinafter sometimes referred to as polysulfone) is a polysulfone polymer having an aromatic nucleus and a sulfonyl group in the main chain. It is sufficient that the aromatic nucleus is substituted with a group represented by the general formula (I), and the group represented by the general formula (I) is 0.0001 to 0.3 per repeating unit. It is preferable to be substituted at a density of
[0012]
Poly Specific examples of the aromatic polysulfone polymer, which is widely available on the market (p- phenylene ether sulfone): - {(p-C 6 H 4) -SO 2 - (p-C 6 H 4) - O-} _n - or, "Udel-polysulfone": - {(p-C 6 H 4) -SO 2 - (p-C 6 H 4) -O- (p-C 6 H 4) -C (CH _{3) 2 - (p-C} 6 H 4) -O} n - _{other, - {(p-C 6} H 4) -SO 2 - (p-C 6 H 4) -O- (p-C 6 _{H 4) -O} n -,} - {(p-C 6 H 4) -SO 2 - (p-C 6 H 4) -S- (p-C 6 H 4) -O} n -, - { _{(p-C 6 H 4)} -SO 2 - (p-C 6 H 4) -O- (p-C 6 H 4) -C (CF 3) 2 - (p-C 6 H 4) -O} _{the n} - a polymer having a structure such as, groups the aromatic nuclei represented by the general formula (I), for example ^{, (N 1, N 2,} N 3 - trioctyl - diethylenetriamino) - acetamidomethyl ^{group, (N 1, N 2,} N 3, N 4 - tetraoctyl - triethylenetetramine amino) - acetamidomethyl group, {poly ( N-lauryltetraethyleneimino)}-acetamidomethyl group, poly (N-laurylethyleneimino) -acetamidomethyl group and the like can be mentioned.
[0013]
The group represented by the general formula (I) will be described in more detail. R ¹ and R ² represent a hydrogen atom or an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, and R ¹ and R ² represent Although they may be the same or different, those in which R ² is a hydrogen atom, particularly those in which both R ¹ and R ² are hydrogen atoms are most preferable because they are most easily produced and have high reactivity. In addition, the poly (alkylaminoalkylene) group of E in the general formula (I) is a part or all of hydrogen atoms bonded to the amino group of a poly (aminoalkylene) group represented by a poly (ethyleneimine) group. Is substituted with an alkyl group having 1 to 24 carbon atoms. Those having a small number of carbon atoms have high hydrophilicity, and those having a large number of carbon atoms have high hydrophobicity. However, when used as an adsorbent, it is preferable to have moderate hydrophobicity. In general, those having 6 to 18 carbon atoms are particularly preferably used as the adsorbent. The substitution rate of the hydrogen atom with an alkyl group depends on the number of carbon atoms in the alkyl group, but if it is too low, the hydrophilicity is too high and the appropriate hydrophobicity required as an adsorbent is difficult to be obtained. When it is several tens or less, it is 1% to 100%, more preferably 10% to 100%, and when it is 10 or more carbon atoms, it is 0.1% to 100%, more preferably 1% to 50%.
[0014]
In the present invention, E in the general formula (I) is an alkyl group having 2 to 24 carbon atoms in which some or all of the hydrogen atoms bonded to the nitrogen atom of the group represented by the following general formula (II) are bonded. It is preferable from the viewpoint of adsorption performance that it is substituted with.
[0015]
^{R 3 R 4 N (A 1} -NR 5 -A 2 -NR 6) n - (II)
R ³ , R ⁴ , R ⁵ and R ⁶ in the general formula (II) are hydrogen atoms or alkyl groups having 1 to 24 carbon atoms, and the number of substituted hydrogen atoms is 99% of the number of nitrogen atoms. Anything is possible as long as it is as follows, and there is no particular limitation. Here, R ³ , R ⁴ , R ⁵ , and R ⁶ may be the same or different, but the same is most easily produced. When these are long-chain alkyl groups having 10 or more carbon atoms, hydrophobicity is strong, and therefore, they are preferably used as adsorbents for hydrophobic interaction.
[0016]
Examples of A ¹ and A ^{2 in} the general formula (II) include ethylene group, trimethylene group, tetramethylene group, hexamethylene group, octamethylene group, decamethylene group, 1-methylethylene group, 2-ethylethylene group, it can be increased and p- xylylene group, a ¹ and a ² may be the same or different.
[0017]
If n in the general formula (II) of the side chain substituent is too small, the effect of the graft structure is difficult to be obtained. On the other hand, if it is too large, the solubility in an organic solvent is lowered and the processing becomes difficult. 5 to 2000 is preferable. Further, the relationship between the density of the group represented by formula (I) and n greatly affects the performance of the polymer. That is, when the density of the group represented by the general formula (I) is high, it is difficult to maintain the excellent physical properties of polysulfone unless n is decreased. Therefore, n is preferably small, while the density is low. If n is small, the effect of the graft structure is difficult to obtain. Therefore, n is preferably large. This poly (aminoalkylene) group may be partially branched. These groups may be present alone or in plural depending on the purpose of use.
[0018]
Furthermore, when the poly (aminoalkylene) group of E in the general formula (I) is a polymer of ethyleneimine, if the degree of polymerization is too low, the functional group effect is increased to increase the side chain functional group density. The degree of polymerization is preferably 4 or more because the physical properties of the resulting product tend to be low. Moreover, since the viscosity of what is obtained when the degree of polymerization is too high may be too high, or the processability may be lowered due to hydrophilicity, it is preferably 4 or more and 10,000 or less, particularly preferably 10 or more and 4000 or less. The ethyleneimine polymer may be partially branched. These groups may be present alone or in plural depending on the purpose of use.
[0019]
The position where the group represented by the general formula (I) is bonded to the main chain of the polysulfone may be anywhere, and is not particularly limited, but can be easily introduced by an amide methylation reaction. It is easy to get the one in the ortho position. For example, in “Udel polysulfone” synthesized from bisfur A and di (chlorophenyl) sulfone, it is easy to obtain those containing the group represented by the general formula (I) at the ortho position from the hydroxyl group of bisphenol A.
[0020]
The proper amount of the group represented by the general formula (I) in the polymer of the present invention, that is, the density varies depending on the chemical structure and use of the main polymer, but if it is too small, its function is difficult to express, If the amount is too large, it is difficult to form a tough film by itself, and even when mixed with polysulfone, the compatibility with polysulfone tends to be poor and film formation tends to be difficult. 0.0001 to 0.3, especially 0.001 to 0.1 is preferable.
[0021]
As an example of the manufacturing method of this invention polymer, the method of adding the corresponding polyamine compound in the solution of haloacetamidomethylated polysulfone, and making it react at the temperature of 0-100 degreeC is mentioned. There are no particular restrictions on the amount of polyamine, but it is desirable to use at least twice the mole of haloacetamidomethyl groups to obtain a soluble polymer. In particular, in the case of a branched polyamine, it is preferable to use a large excess of polyamine in order to obtain a soluble polymer. As a polyamine compound, it is a usual method to use a polyamine having a necessary amount of N-alkyl groups in the end, but it becomes difficult to dissolve in a solvent when the N-alkylation rate increases. There is also a method of using a polyamine having an N-alkyl group less than the amount, or using a polyamine which is not N-alkylated at all and then performing a necessary amount of alkylation with an alkylating reagent such as an alkyl halide. Adopted as appropriate.
[0022]
As the reaction solvent, tetrahydrofuran, dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like are preferably used when the reaction is carried out in a homogeneous system. Further, it is possible to introduce a polyamine by surface treatment after molding the haloacetamidomethylated polysulfone. For this purpose, a solvent that dissolves the polyamine without dissolving the polysulfone such as water, methanol, and ethanol is preferably used.
[0023]
The polymer of the present invention is used as an adsorbent by itself or as an intermediate for the production of adsorbents with higher functions, and is used for filtration separation and concentration of various substances in the form of flat membranes and hollow fiber membranes. Used for. Moreover, the use to a cell culture instrument, an artificial organ, an artificial blood vessel, a catheter, etc. can be considered.
[0024]
【Example】
Hereinafter, the present invention will be described more specifically by experimental examples.
[0025]
In addition, the evaluation method in a present Example followed the following.
[0026]
1. An infrared absorption spectrum polymer was dissolved in chloroform, poured onto a glass plate, and molded into a film shape, and measured using a Shimadzu Fourier transform infrared spectrophotometer FT-IR4300.
[0027]
Example 1
After cooling a mixed solution of 8 mL of nitrobenzene and 15 mL of sulfuric acid to 0 ° C., 2.0 g of N-methylol-α-chloroacetamide was added and dissolved, and this was a solution of 300 g of Udelpolysulfone P3500 dissolved in 3 L of nitrobenzene. Was added with good stirring. Further, after stirring at room temperature for 3 hours, the reaction mixture was placed in a large excess of cold methanol to precipitate the polymer. The precipitate was washed well with methanol and dried. This was dissolved in dimethylformamide and then reprecipitated with methanol and purified to obtain 308 g of α-chloroacetamidomethylated polysulfone (Polymer-I). This polymer showed absorption of an amide group at 1676 cm ⁻¹ in an infrared absorption spectrum.
[0028]
34.9 g of lauryl bromide was added to a solution of 60 g of polyethyleneimine (average molecular weight 10,000: Wako Pure Chemical Industries) dissolved in 300 mL of dimethylformamide, and stirred at room temperature for 3 days to prepare a lauryl polyethyleneimine solution. Separately, 30 g of the polymer-I obtained above was dissolved in 300 mL of dimethylformamide, mixed with the laurylated polyethyleneimine solution, and stirred at room temperature for 3 days. The reaction mixture was poured into a large excess of saturated brine to precipitate the polymer. The precipitate was washed well with water and methanol and then dried to obtain 29 g of the polymer of the present invention.
[0029]
This polymer showed absorption of an amide group at 1666 cm ⁻¹ in the infrared absorption spectrum, and absorption of methylene groups (ethylenediamino group and lauryl group) at 2966 cm ⁻¹ , 2926 cm ⁻¹ and 2853 cm ⁻¹ . This dissolved well in tetrahydrofuran, chloroform and dimethylformamide. The nitrogen content by elemental analysis was 2.8 mmol / g.
[0030]
A dimethylacetamide solution of this polymer was applied onto glass and placed in water to form a film. As a result, a semipermeable membrane having mechanical properties unchanged from that of polysulfone was obtained.
[0031]
Example 2
40 g of the polymer-I obtained in Example 1 was dissolved in 400 mL of dimethylformamide, and 270 mL of 30% polyethyleneimine aqueous solution (average molecular weight 70000: Wako Pure Chemical Industries) was concentrated under reduced pressure to obtain 240 mL of dimethylformamide. It was added to the dissolved solution and stirred at room temperature for 3 days. The reaction mixture was poured into a large excess of saturated brine to precipitate the polymer. The precipitate was washed well with water and methanol and then dried to obtain 38 g of a polymer. 8 g of this polymer was dissolved in 100 mL of dimethylformamide, 2 g of potassium iodide and 4 mL of lauryl bromide were added thereto, and the mixture was stirred at room temperature for 24 hours. The reaction mixture was put in a large excess of methanol to precipitate the polymer. The precipitate was washed well with methanol and water and then dried to obtain 6.3 g of the polymer of the present invention.
[0032]
This polymer showed absorption of an amide group at 1666 cm ⁻¹ in the infrared absorption spectrum, and absorption of methylene groups (ethylenediamino group and lauryl group) at 2966 cm ⁻¹ , 2926 cm ⁻¹ and 2853 cm ⁻¹ . This dissolved well in tetrahydrofuran, chloroform and dimethylformamide. The nitrogen content by elemental analysis was 1.0 mmol / g.
[0033]
A dimethylacetamide solution of this polymer was applied onto glass and placed in water to form a film. As a result, a semipermeable membrane having mechanical properties unchanged from that of polysulfone was obtained.
[0034]
Example 3
11 g of lauryl bromide was added to a solution of 20 g of polyethyleneimine (average molecular weight 10,000: Wako Pure Chemical Industries) dissolved in 100 mL of dimethylformamide, and stirred at room temperature for 3 days to prepare a laurylated polyethyleneimine solution. Separately, 10 g of the polymer-I obtained in Example 1 was dissolved in 100 mL of dimethylformamide, mixed with the laurylated polyethyleneimine solution, and stirred at room temperature for 1 day. Further, 55 g of lauryl bromide was added and stirred at room temperature for 2 days. The reaction mixture was poured into a large excess of methanol to precipitate the polymer. The precipitate was washed well with water and methanol and then dried to obtain 10 g of the polymer of the present invention.
[0035]
This polymer showed an absorption of amide group at 1666 cm ^-1 in the infrared absorption spectrum showed absorption methylene groups (ethylene diamino group and lauryl group) to 2966cm ^-1 and 2926cm ^-1 and 2854cm ^-1. In particular, the absorption of 2926cm ^-1 is compared with the absorption of 2966cm ^-1 and 2854cm ^-1, greater. This dissolved well in tetrahydrofuran, chloroform and dimethylformamide. The nitrogen content by elemental analysis was 2.8 mmol / g.
[0036]
A dimethylacetamide solution of this polymer was applied onto glass and placed in water to form a film. As a result, a semipermeable membrane having mechanical properties unchanged from that of polysulfone was obtained.
[0037]
Example 4
15 g of hexyl bromide was added to a solution of 20 g of polyethyleneimine (average molecular weight 10,000: Wako Pure Chemical Industries) dissolved in 100 mL of dimethylformamide, and stirred at room temperature for 2 days to prepare a hexylated polyethyleneimine solution. Separately, 10 g of the polymer-I obtained in Example 1 was dissolved in 100 mL of dimethylformamide, mixed with a hexylated polyethyleneimine solution, and stirred at room temperature for 3 days. The reaction mixture was poured into a large excess of saturated brine to precipitate the polymer. The precipitate was washed well with water and methanol and then dried to obtain 10 g of the polymer of the present invention.
[0038]
This polymer showed absorption of amide groups at 1670 cm ⁻¹ in the infrared absorption spectrum, and absorption of methylene groups (ethylenediamino group and hexyl group) at 2968 cm ⁻¹ , 2932 cm ⁻¹ and 2872 cm ⁻¹ . This dissolved well in tetrahydrofuran, chloroform and dimethylformamide. The nitrogen content by elemental analysis was 2.6 mmol / g.
[0039]
A dimethylacetamide solution of this polymer was applied onto glass and placed in water to form a film. As a result, a semipermeable membrane having mechanical properties unchanged from that of polysulfone was obtained.
[0040]
Example 5
11 g of lauryl bromide was added to a solution of 20 g of polyethyleneimine (average molecular weight 25000: Aldrich Company) in 100 mL of dimethylformamide, and stirred at room temperature for 2 days to prepare a lauryl polyethyleneimine solution. Separately, 10 g of the polymer-I obtained in Example 1 was dissolved in 100 mL of dimethylformamide, mixed with the laurylpolyethyleneimine solution, and stirred at room temperature for 3 days. The reaction mixture was poured into a large excess of saturated brine to precipitate the polymer, and the precipitate was washed well with water and methanol, then dried and dried to obtain 11 g of the polymer of the present invention.
[0041]
This polymer showed absorption of amide groups at 1670 cm ⁻¹ in the infrared absorption spectrum, and absorption of methylene groups (ethylenediamino group and lauryl group) at 2966 cm ⁻¹ , 2923 cm ⁻¹ and 2853 cm ⁻¹ . In particular, the absorption of 2926cm ^-1 is compared with the absorption of 2966cm ^-1 and 2854cm ^-1, greater. This dissolved well in tetrahydrofuran, chloroform and dimethylformamide. The nitrogen content by elemental analysis was 2.9 mmol / g. As a result of coating a dimethylacetamide solution of this polymer on glass and placing it in water to form a film, a semipermeable membrane having high hydrophilicity was obtained, although the mechanical properties were not changed compared to polysulfone.
[0042]
Example 6
20 g of the polymer-I obtained in Example 1 was dissolved in 200 mL of dimethylformamide, and 40 g of polyethyleneimine (average molecular weight 700: Aldrich Company) was added to the solution in 200 mL of dimethylformamide, and stirred at room temperature for 3 days. did. The reaction mixture was poured into a large excess of saturated brine to precipitate the polymer. The precipitate was washed well with water and methanol, and then dried to obtain 18 g of a polymer. 8 g of this polymer was dissolved in 100 mL of dimethylformamide, 2 g of potassium iodide and 16 mL of stearyl bromide were added thereto, and the mixture was stirred at room temperature for 24 hours. The reaction mixture was put in a large excess of methanol to precipitate the polymer. The precipitate was washed well with ethanol and water and then dried to obtain 8.3 g of the polymer of the present invention. This polymer showed absorption of amide groups at 1668 cm ⁻¹ in the infrared absorption spectrum, and absorption of methylene groups (ethylene diamino group and stearyl group) at 2968 cm ⁻¹ , 2926 cm ⁻¹ and 2853 cm ⁻¹ . In particular, the absorption of 2926cm ^-1 is compared with the absorption of 2966cm ^-1 and 2854cm ^-1, greater. This dissolved well in tetrahydrofuran, chloroform and dimethylformamide. The nitrogen content by elemental analysis was 0.9 mmol / g.
[0043]
A dimethylacetamide solution of this polymer was applied onto glass and placed in water to form a film. As a result, a semipermeable membrane having mechanical properties unchanged from that of polysulfone was obtained.
[0044]
Example 7
After cooling a mixed solution of 16 mL of nitrobenzene and 31 mL of sulfuric acid to 0 ° C., 4.2 g (0.034 mol) of N-methylol-α-chloroacetamide was added and dissolved, and 300 g (0.68 mol) of this solution was dissolved. ) Udelpolysulfone P3500 in 360 mL of nitrobenzene was added with good stirring. Furthermore, it stirred at room temperature for 3 hours. The reaction mixture was then placed in a large excess of cold methanol to precipitate the polymer. The precipitate was washed well with methanol and dried to obtain 308 g of α-chloroacetamidomethylated polysulfone (Polymer-II). This product showed absorption of an amide group at 1676 cm ⁻¹ in an infrared absorption spectrum.
[0045]
20 g of the polymer-II obtained above was dissolved in 200 mL of dimethylformamide, and 11 g of lauryl bromide was added to a solution of 20 g of polyethyleneimine (average molecular weight 25000: Aldrich Company) in 100 mL of dimethylformamide. A lauryl polyethyleneimine solution was prepared by stirring. Separately, 10 g of the polymer-II obtained above was dissolved in 100 mL of dimethylformamide, mixed with the laurylpolyethyleneimine solution, and stirred at room temperature for 3 days. The reaction mixture was poured into a large excess of saturated brine to precipitate the polymer. The precipitate was washed well with water and methanol, then dried and dried to obtain 11 g of the polymer of the present invention.
[0046]
This polymer showed absorption of amide groups at 1670 cm ⁻¹ in the infrared absorption spectrum, and absorption of methylene groups (ethylenediamino group and lauryl group) at 2966 cm ⁻¹ , 2923 cm ⁻¹ and 2853 cm ⁻¹ . In particular, the absorption of 2926cm ^-1 is compared with the absorption of 2966cm-1 and 2854cm ^-1, greater. This dissolved well in tetrahydrofuran, chloroform and dimethylformamide. The nitrogen content by elemental analysis was 2.9 mmol / g. As a result of coating a dimethylacetamide solution of this polymer on glass and putting it in water to form a film, a semipermeable membrane having high hydrophilicity was obtained, although the mechanical properties were not changed as compared with polysulfone.
[0047]
【The invention's effect】
As described in detail above, the present invention obtains a soluble novel aromatic polysulfone polymer having excellent characteristics by introducing a specific polyalkylamine graft group as a side chain into the aromatic polysulfone of the main chain. It is useful as a treatment material for adsorption, separation, fixation, etc. of ionic substances and physiologically active substances.
[0048]
In addition, the aromatic polysulfone polymer is used in the form of molded articles such as petri dishes, bottles, membranes, fibers, hollow fibers, granules, or assemblies using these, and is used as an adsorbent for affinity chromatography and a blood treatment agent for treatment. It can be suitably used as a raw material such as an antibacterial material.

Claims (9)

As the side chain functional group, a group represented by the following general formula (I) (wherein E represents a poly (alkylaminoalkylene) group, R ¹ represents an alkyl group having 1 to 20 carbon atoms, R ² Represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R ¹ and R ² may be the same or different. } Is introduced into the aromatic polysulfone polymer.
E—CH (R ¹ ) —CO—NR ² —CH ₂ — (I) E in the general formula (I) is a group represented by the following general formula (II) (wherein A ¹ and A ² are an alkylene group having 2 to 12 carbon atoms or a carbon number in which a methyl group is branched) Represents an alkylene group having 3 to 12 carbon atoms, an alkylene group having 4 to 12 carbon atoms branched from an ethyl group, or a xylylene group, and A ¹ and A ² may be the same or different from each other, R ³ , R ⁴ , R ⁵ , R ⁶ represents a hydrogen atom or an alkyl group having 1 to 24 carbon atoms, and R ³ , R ⁴ , R ⁵ and R ⁶ may be the same or different, but the number of hydrogen atoms is the number of nitrogen atoms The aromatic polysulfone polymer according to claim 1, wherein n is an integer of 2 or more.
^{R 3 R 4 N (A 1} -NR 5 -A 2 -NR 6) n - (II) 2. The aromatic polysulfone polymer according to claim 1, wherein the poly (alkylaminoalkylene) group in the general formula (I) is a polymer of N-alkylethyleneimine having a polymerization degree of 4 or more and 10,000 or less. 2. The aromatic polysulfone polymer according to claim 1, wherein the main chain of the aromatic polysulfone polymer is poly (p-phenylene ether sulfone). The main chain of the aromatic polysulfone polymer has the chemical formula-{(p-C ₆ H ₄ ) -SO _2- (p-C ₆ H ₄ ) -O- (p-C ₆ H ₄ ) -C (CH ₃ ) _{2. - (p-C 6 H 4} ) -O} n - it is characterized by being represented by claim 1 the aromatic polysulfone polymer according. The aromatic polysulfone polymer according to claim 1, wherein the density of the side chain functional group is 0.0001 to 0.3 per repeating unit of the main chain. 3. The aromatic polysulfone polymer according to claim 2, wherein n in the general formula (II) is 2 to 5000. The polymer according to claim 1, which is soluble in any of tetrahydrofuran, dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and chloroform . The aromatic polysulfone polymer having a halogen substituent represented by the following general formula (III) (wherein X represents a halogen atom) is reacted with a polyamine compound. A method for producing an aromatic polysulfone polymer.
X—CH (R ¹ ) —CO—N (R ² ) —CH ₂ — (III)