JPS5923308B2 - N↓-(4'↓-chlorosulfophenyl)↓-4↓-chloroformylphthalimide and its manufacturing method - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to N-(4-chlorosulfophenyl)-4-
This invention relates to a novel compound consisting of chloroformylphthalimide and a method for producing the same.

Polymers with imide bonds have good heat resistance and are used as engineering plastics. An imide bond is formed by condensing two adjacent carboxylic acid groups or their anhydrides with an amine compound, and by utilizing this reaction, it is possible to form an imide bond by condensing two adjacent carboxylic acid groups or their anhydrides with an amine compound. An imide-bonded gold polymer can be produced by polycondensing an anhydride and a bifunctional compound in which at least one is an amine group. On the other hand, it is also possible to obtain an imide-bonded gold polymer by polycondensing an at least bifunctional compound having an imide bond in its molecule and a compound having at least two functional groups that can be condensed therewith. can. Since the imide bond forming reaction is relatively difficult, the present inventor selected a bifunctional compound having an imide bond and produced an imide bonded gold polymer using an easier polycondensation reaction. investigated. A variety of bifunctional compounds having an imide bond have been known to have various properties, but the inventors have conducted various research studies in order to discover compounds that have not been previously known. As a result, they discovered a new compound called N-(4'-chlorosulfophenino-4-chloroformylphthalimide.This compound has a unique molecular structure and has active functional groups at both ends. There is.

The functional groups at both ends can be condensed with phenolic hydroxyl groups, amine groups, alcoholic hydroxyl groups, or other functional groups, and this can be used to produce high molecular weight polymers. The resulting imide-bonded gold polymer can be used not only as a heat-resistant resin, but also as a semipermeable membrane. The compound of the present invention can be produced by various methods, but generally it is produced by reacting trimellitic acid or its anhydride with P-aminobenzenesulfonic acid (sulfanilic acid) or its alkali salt (X:H or This can be easily carried out by reacting a compound (alkaline residue) with a conventional chlorinating agent such as phosphorus pentachloride, phosgene, or thionyl chloride.

The preferred acid component is trimellitic anhydride and the amine component is an alkali metal salt of P-aminobenzenesulfonic acid. The reason why both of these are preferable is that they are the combinations that cause the easiest reaction compared to other raw materials, and also have the highest yields. Thionyl chloride is the most suitable chlorinating agent. Since phosgene is a toxic gaseous chlorinating agent, its handling is complicated, and phosphorus pentachloride is complicated to separate as a by-product phosphorus compound.

Compared to these, thionyl chloride is a liquid chlorination agent that can be easily handled and the product can be easily separated. Of course, phosgene, phosphorus pentachloride, and other chlorinating agents cannot also be used. The reaction between trimellitic acid or its anhydride and P-aminobenzenesulfonic acid or its alkali salt is carried out in a solvent that is inert to both.

The solvent is preferably one that can dissolve both raw materials, such as dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, or other solvents. Both are dissolved in a solvent and heated to perform an imide bond formation reaction. At this time, compounds such as pyridine, tributylamine, and acetic anhydride may be used to promote the reaction. This is a compound represented by (X:H or an alkali residue), which is then chlorinated. When thionyl chloride is used as a chlorinating agent, chlorination can be carried out by adding this compound to thionyl chloride and heating. EXAMPLES The present invention will be specifically explained below with reference to Examples, but the present invention is not limited to these Examples.

Further, two specific examples of uses of the compound of the present invention have been described as reference examples, but of course the compound of the present invention is not limited to only these uses. Example 1 In 200 ml of dimethylformamide, 27.69 g of trimellitic anhydride and 309 g of sodium sulfanilate dihydrate are stirred at room temperature for 2 hours.

During this time, the solution becomes homogeneous. Then, acetic anhydride 20
Add ml and 5ml of pyridine, and raise the reaction temperature to 130-140.
When the reaction is carried out at ℃ for 2 hours with stirring, a white solid substance is formed. After cooling the reaction solution, the generated solid is separated, thoroughly washed with acetone, and then dried. The obtained solid was recrystallized from water and then dried under reduced pressure at 40° C. for about 10 hours to obtain white crystals 50.49. This compound was hot.

Next, this compound 259 was heated under reflux for 3 hours in 250 ml of thionyl chloride to which a few drops of dimethylformamide had been added. Excess thionyl chloride was distilled off under reduced pressure, and the residue was dissolved in benzene-toluene (1:1 ) Recrystallization twice from the mixed solution gave white crystals 1929 with a melting point of 166°C.

The infrared absorption spectrum (Figure 1) and elemental analysis showed that this compound was the target substance N-(47-chlorosulfofenino-4-thalolform.milphthalimide.Calculated elemental analysis value) : C, 46.88; H, 1.83; N, 365 Actual value: C, 46.28; H, 1.84; N, 34O Example 2 Compound polymer () obtained in the same manner as Example 1 was dissolved in N-methylpyrrolidone to a concentration of 20 wt%, and further added 48% by weight of the polymer.

79 is suspended in 240 ml of benzene, and a mixed solution of 62 ml of thionyl chloride and 240 ml of benzene is gradually added dropwise over a period of time while stirring at the reflux temperature of benzene.

After the dropwise addition was completed, the reaction was continued for another 3 hours at the reflux temperature. After the formed sodium chloride is removed by thermal aging, pale yellow crystals are formed by cooling the benzene solution. After the crystals were distributed from house to house, they were recrystallized from benzene to obtain white crystals 509. This compound has a melting point of 166°C and an infrared absorption vector that is the same as that of the target compound obtained in Example 1.
Reference Example 1 Confirmed to be dichlorosulfophenyl-4-chloroformylphthalimide 1 The compound of the present invention and diaminodiphenyl ether were reacted by a low temperature solution polymerization method to form polyamideimide sulfonamide (1). Obtained.

A 15% dimethylacetamide solution of Polymer 1 (1) was cast on a glass plate, and the solvent was distilled off under reduced pressure at 150° C. for 4 hours to obtain a yellow, tough, flexible film.

This film had a tensile strength of 9.4 kg/11112, an elongation of 9%, a tensile modulus of elasticity of 340 x 1,04 k9/Cl, and no weight loss was observed up to 300°C. Reference Example 2 The compound of the present invention and bulk phenylene diamine were reacted by a low temperature solution polymerization method, and polyamideimide sulfonamide () was coated with a doctor knife on a smooth glass plate to a thickness of 200 μm.
The mixture was spread at room temperature.

After drying at 140℃ for 40 minutes, the whole glass plate was dried at 22℃.
The separated film was immersed in a large amount of water at room temperature overnight.

The membrane thus obtained was yellowish-brown and transparent with a thickness of 60 μm.
It was hot.

This wet membrane was set in an experimental reverse osmosis device. The membrane area was 120 (Ii), and the membrane surface that had been exposed to air during membrane formation and drying was brought into contact with the high-pressure solution side. A 5,000 degree sodium chloride aqueous solution was used as the solution, and the membrane was heated under a pressure of 40k9/d with stirring. The experiment was conducted at 22°C.The basis weight of the salt that flowed through the membrane was measured, and the salt concentration was measured by the conductivity method.As a result, the water permeability was 0.23 m3/M2day.
The salt concentration of the permeated water was 100 PPI1.

[Brief explanation of the drawing]

Figure 1 shows the present invention N-(4'-chlorosulfophenyl)-
4-Chloroformylphthalimide. R. FIG.

Claims (1)

[Claims] ▲Numerical formulas, chemical formulas, tables, etc.▼N-(4'-chlorosulfophenyl) having the structure
-4-Chloroformylphthalimide. 2. Chlorination of the compound (X: H or alkali residue) obtained by reacting trimellitic acid or its anhydride with P-aminobenzenesulfonic acid or its alkali salt. ▲There are mathematical formulas, chemical formulas, tables, etc.▼N-(4'-chlorosulfophenyl)- which is characterized by being chlorinated with a chemical agent.
Method for producing 4-chloroformylphthalimide. 3. The manufacturing method according to claim 2, wherein the alkali salt is an alkali metal salt. 4. The manufacturing method according to claim 2, wherein the chlorinating agent is thionyl chloride.