JPH01143867A - Novel imide compound and its production - Google Patents

Abstract

NEW MATERIAL:An imide of formula I [A is formula II, formula III (X is direct bond, O, S, SO2, CO, CH2CH2, formula IV; R is methyl, ethyl, isopropyl, methoxy, carboxy, Cl, Br, OH); n is 1-5]. EXAMPLE:A reaction product between 3,3',4,4'-diphenylsulfonetetracarboxylic acid dianhydride, 4,4'-diaminodiphenyl ether and maleic acid. USE:A thermosetting imide compound for polyimide which is soluble in organic solvents, and excellent in solvent resistance and impact resistance. PREPARATION:At least one of diphenylsulfonetetracarboxylic acid is allowed to react with an aromatic diamine and/or its isocyanate and maleic acid or a dicarboxylic acid which can form maleic acid by heating to give the compound of formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel imide compound and a method for producing the same.

[Prior Art] In general, polyimide resins are widely used as materials with excellent heat resistance in films used at high temperatures, materials for laminates, molding materials, wire covering materials, adhesives, and paints.

Conventionally, the most famous polyimide is a polycondensate of pyromellitic acid and aromatic diamine.

This product is obtained by preparing a polyamic acid using an acid anhydride and a diamine in a polar solvent, applying this solution to a base material, and heating and dehydrating the resulting film. However, in this method, pinholes occur due to the separation of reaction water. Furthermore, polyamic acid solutions are unstable and whiten due to dehydration and cyclization, so they have to be stored at low temperatures, which is inconvenient.

To compensate for these drawbacks, polyimides containing flexible carboxylic acids and flexible or asymmetric diamines have been proposed. Since the polyimide itself is soluble in organic solvents, there are no problems such as pinhole formation.
The problem of poor solvent resistance still remains.

Further, N,N--(methylenedi-p-phenylene) simaleimide is often used as a thermosetting imide for laminated boards. However, the biggest drawback of the cured polyimide obtained from this product is that it is brittle, and even if modified with a polymaleimide such as aniline-formalin resin, which has excellent impact resistance, no sufficient improvement could be achieved.

[Problems to be Solved by the Invention] In order to solve these problems, the present inventors have conducted various studies and found that a novel imide compound having a specific structure constitutes a polyimide having desired properties. The present invention was completed based on this finding.

That is, an object of the present invention is to provide a novel thermosetting imide compound capable of preparing a polyimide that is soluble in organic solvents, has excellent solvent resistance, and has good impact resistance, and a method for producing the same. .

[Means for Solving the Problems] The imide compound according to the present invention is characterized by being represented by general formula (I).

X represents a direct bond, -0-1-S-1-SO2-1 and HJ −〇. Yl, Y2 are hydrogen atoms, 0°
- Methyl, ethyl, -C7, -Br, -CF3, -Cl-
They represent 8 groups of 12CF3 and may be the same or different. R is methyl, ethyl, isopropyl, methoxy, ethoxy, carboxyl, -CI! ,-Br,-
Represents 8 groups of OH and 5O3H. n is an integer from 1 to 5. ) That is, the compound is an oligoimide that has an imide skeleton obtained from diphenylsulfonetetracarboxylic acids and an aromatic diamine and/or its isocyanate, and has a maleimide group at the molecular end, and belongs to diphenylsulfonetetracarboxylic acids. It can be produced by reacting one or more compounds with aromatic diamine and/or its isocyanate and maleic acid or dicarboxylic acids capable of producing maleic acid upon heating.

The diphenylsulfonetetracarboxylic acids according to the present invention include diphenylsulfonetetracarboxylic acid and the anhydride or dianhydride, or monoesters and diesters of these with lower alcohols such as methanol, ethanol, propatool, and isopropanol; It is a general term for triesters, tetraesters, monoesters, diesters, triesters, tetraesters, etc. with polyhydric alcohols such as ethylene glycol, diethylene glycol, triethylene glycol, and glycerin.

Further, as the aromatic diamine, specifically, 4.4'-diaminodiphenyl ether, 4.4'-diaminodiphenyl sulfide, 4.4-diaminodiphenylbenzophenone, 4.4'-diaminodiphenyl sulfone, 4.
．． 4'-diaminodiphenylmethane, 4.4-diaminodiphenylethane, 4.4'-diaminodiphenyldimethylmethane, 4.4'-diaminodiphenylmethylethylmethane, 4.4-diaminodiphenyldiethylmethane, 4.4
--Diaminodiphenyldichloromethane, 4.4--Diaminodiphenyldibromomethane, 4.4'-Diaminodiphenyldi(trifluoromethyl)methane, 4.4'-Diaminodiphenyltrifluoromethylpentafluoroethylmethane, 4.4- -diaminodiphenyldi(pentafluoroethyl)methane, 3.3'-dimethyl-4,4-diaminodiphenylmethane, 3.3'-dimethoxy-4,4'-diaminodiphenylmethane, 3.3'-jethoxy-4, 4--diaminodiphenylmethane, 3.3'-dicarboxy-4,4'-diaminodiphenylmethane, 3.3'-dichloro-4,4-diaminodiphenylmethane, 3.3-monodihydroxy-4,4-diamino Diphenylmethane, 3.3'-disulfo-4,4-diaminodiphenylmethane, 3.3-dimethyl-4,4'-diaminodiphenyl ether, 3.3-dimethoxy-4,4-monodiaminodiphenyl ether, 3.3 --Jethoxy-4,4'-diaminodiphenyl ether, 3.3'-dicarboxy-4,4-diaminodiphenyl ether, 3.3-dichloro-4,4'-diaminodiphenyl ether, 3.3'-dihydroxy- 4,4'-diaminodiphenyl ether, 3.3'-disulfo-4,4'-diaminodiphenyl ether, 3.3'-dimethyl-4,4'-diaminodiphenyl sulfone, 3.3'-dimethoxy-4,4' -diaminodiphenylsulfone, 3.3'-jethoxy-4,4-diaminodiphenylsulfone, 3.3-dicarboxy-4,4'-diaminodiphenylsulfone, 3.3'-dichloro-4,4-- Diaminodiphenylsulfone, 3,3-dihydroxy-4,4-diaminodiphenylsulfone, 3,3-disulfo-4,4-diaminodiphenylsulfone, 3,3'-dimethyl-4,4'-diaminodiphenylpropane , 3.3-dimethoxy-4,4-diaminodiphenylpropane, 3.3'-jethoxy-4,4'-diaminodiphenylpropane, 3.3'-dicarboxy-4,4'-diaminodiphenylpropane, 3 .3-dichloro-4,4-diaminodiphenylpropane, 3.3-dihydroxy-4,4'-diaminodiphenylpropane, 3.3-disulfo-4,4-diaminodiphenylpropane, 3.3 '-dimethyl-4,4'-diaminodiphenylsulfide, 3.3-dimethoxy-4,4'-diaminodiphenylsulfide, 3.3'-jethoxy-4,4'-diaminodiphenylsulfide, 3.3-dimethoxy-4,4'-diaminodiphenylsulfide Carboxy-4,4'-diaminodiphenylsulfide, 3,3-dichloro-4,4'-diaminodiphenylsulfide, 3,3'-dihydroxy-4,4'-diaminodiphenylsulfide, 3,3'-disulfo- 4,4--diaminodiphenyl sulfide, 3.3-diaminodiphenylmethane, 3.3'-diaminophenyl ether, 3.3'-diaminodiphenylsulfone, 3.3'-diaminodiphenylpropane, 3
．． 3--diaminodiphenyl sulfide, 4.4'-(
p-phenylenediisopropylidene)bisaniline, 3.4-diaminodiphenyl ether, 3.4'-diaminodiphenylmethane, 3.4-diaminodiphenylsulfone, 3.4-1diaminodiphenyl sulfide, 3.4-diaminodiphenyl Benzophenone, 3.
4'-diaminodiphenyldimethylmethane, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, bis[4-(4-aminophenoxy)phenyl]sulfone, 1,4-bis(4-aminophenoxy) ) Benzene, 1.
3-bis(4-aminophenoxy)benzene, 1.3-
Bis(3-aminophenoxy)benzene, o-toluidine sulfone, 1.5-diaminonaphthalene, 9.9-bis(4-aminophenyl)fluorene, 9.
9-bis(4-aminophenyl)-10-hydroanthracene, benzidine, 3.3'-dichlorobenzidine, 3.3-1 dimethylbenzidine, 2.2'-dimethylbenzidine, 3.3'-dimethoxybenzidine, 3 .3'-dimethyl-4,4--diaminobiphenyl-6,6-disulfonic acid, 2.2'-dichloro-5,5-dimethoxybenzidine, 2.2", 5.5"-tetrachlorobenzidine 2.4-
Diaminotoluene, 2.6-diaminotoluene, 1-methoxy-2,4-diaminobenzene, 1-ethoxy-2,4-diaminobenzene, 2.4-diaminobenzoic acid, 2.6-diaminobenzoic acid, 2. 4-diaminophenol, 2,6-diaminophenol, 1-sulfo-2,4-diaminobenzene, 1-chloro-
2,4-diaminobenzene, 1-bromo-2,4-diaminobenzene, 1-isopropyl-2,4-metaphenylenecia++1 Kuno, metaphenylenediamine, paraphenylenediamine alone or in combination of two or more of these A combination is exemplified.

Furthermore, isocyanates of these diamines also serve as raw materials for the imide compound according to the present invention.

Maleic acids are a general term for maleic acid, maleic anhydride, and their monoalkyl esters and dialkyl esters.

Furthermore, dicarboxylic acids that can generate maleic acids by heating include nadic acid, methylnadic acid, tetrahydrophthalic acid, 3-methyltetrahydrophthalic acid,
- Polyhydric carboxylic acids such as -methyltetrahydrophthalic acid and their anhydrides are exemplified, and terminal nadic acid imide compounds are also included.

Specific manufacturing conditions for the compound according to the present invention are shown below.

First, diphenylsulfonetetracarboxylic acids, preferably dianhydrides, and 1.2 to 2.0 times the molar amount of aromatic diamine are reacted in the presence of a solvent to form an amic acid.

The solvents used here include N-methylpyrrolidrine, N
, N-dimethylacetamide, N,N-dimethylformamide, dimethyl sulfoxide, tetramethylurea, trimethyl hexamethylphosphate, γ-butyrolactone, aprotic polar solvents, phenol, cresol, xylenol, dark lephenol, bromophenol, etc. Examples include protic solvents. Among these solvents, m-cresol is industrially preferred because it is liquid at room temperature and is inexpensive.

The reaction substrate concentration is generally about 1 to 70% by weight, preferably about 5 to 40% by weight.

The reaction temperature is generally 0 to 150°C, preferably 10 to 150°C.
The temperature is 70°C.

Generally, the reaction proceeds quickly and is usually completed within 30 minutes to 24 hours. However, 50 hours may be required depending on the form of the carboxylic acid and the type of aromatic diamine.

Imidization is carried out by heating this reaction solution to 100°C to 300°C. At that time, the produced water is distilled out of the system. In this case, a nonpolar solvent such as xylene or toluene may be used in combination as an entrainer.

As a catalyst, it is also effective to use mineral acids such as sulfuric acid and phosphoric acid, and their -class, secondary, tertiary, and quaternary alkyl ammonium salts.

On the other hand, in addition to the thermal imidization as described above, it is also possible to react until an amic acid is formed using diphenylsulfone tetracarboxylic acids, and then to imidize it by acting with a lower carboxylic acid anhydride in the presence of a catalyst.

Examples of the lower carboxylic anhydride include lower carboxylic anhydrides such as acetic anhydride, propionic anhydride, and acetic anhydride.

Here, the number of moles of the appropriate lower carboxylic acid anhydride is about 0.1 to 10 times, preferably 0.5 to 10 times, relative to the amic acid.
It is about 3 times the amount. If it is less than this, cyclization will be insufficient, and if it is more than this, there will be a disadvantage in terms of production costs.

Catalysts applicable to this reaction include trimethylamine, triethylamine, tripropylamine, tributylamine, N-methylpiperidine, N-methylmorpholine, 1,8-diaza-bicyclo(5,4,O)undecene-7, etc. Aliphatic and alicyclic tertiary amines, pyridine, 2-
Examples include heterocyclic amines such as methylpyridine, quinoline, isoquinoline, and methylimidazole, and metal salts such as cobalt acetate, cobalt naphthenate, manganese acetate, and manganese naphthenate.

The reaction temperature is 0 to 200°C, preferably 20 to 120°C.
It is.

If the isocyanate is used instead of the aromatic diamine, the imidization reaction can be carried out in one step.

That is, the imide compound can be obtained by dissolving diphenylsulfonetetracarboxylic acid or its anhydride and aromatic diisocyanate in the imidization solvent and heating the solution.

Catalysts for this reaction include trimethylamine, triethylamine, tripropylamine, tributylamine, N-
Methylpiperidine, 1,8-diaza-bicyclo(5,4
,0>Aliphatic and alicyclic tertiary amines such as undecene-7, aromatic tertiary amines such as N,N-dimethylaniline and N,N-diethylaniline, pyridine, quinoline, picoline, and N-methylimida. Heterocyclic amines such as nols can be used.

The amount of catalytic VX is approximately 0.1 per isocyanate group.
An example is about 30 to 30 times the mole, preferably about 0.5 to 10 times the mole.

The reaction is carried out at 80-250°C, preferably 100-200°C.
It is carried out for 5 minutes to 48 hours.

Next, maleic acid or a dicarboxylic acid capable of producing maleic acid is added to the imide having an amino group at the end of the molecule obtained by the above operation, and a maleimidization reaction is carried out under heating.

The amount of maleic acid or dicarboxylic acids added is 0.4 to 10% relative to diphenylsulfonetetracarboxylic acid.
twice the molar amount, preferably 0.4 to 3 times the molar amount. If the amount is less than this, it is insufficient to convert the entire amount of the amine group at the end of the molecule into maleimide, and if it is more than this, it is not desirable because it is economically disadvantageous, curing of the imide compound is hindered, or excess maleic acid sublimes. do not have.

The maleimidization reaction can be carried out in exactly the same manner as the imidization reaction between the diphenylsulfone tetracarboxylic acids and the aromatic diamine.

In addition, maleic acids are added to the amic acids of diphenylsulfonetetracarboxylic acids and aromatic diamines to form an amic acid with maleamic acid at the end of the molecule, which is then synthesized by heat dehydration or dehydration reaction using a carboxylic acid anhydride. You can also.

The molar ratio of diphenylsulfone tetracarboxylic acids, aromatic diamine, and maleic acids and the reaction conditions at this time can be carried out in exactly the same manner as in the above-mentioned imidization reaction.

In particular, the combination of diphenylsulfonetetracarboxylic dianhydride, aromatic diamine, and maleic anhydride is most preferred because the desired product can be obtained with easy operations.

The product obtained by the above operation may be used as it is in the form of a solution, or the reaction product may be poured into a poor solvent such as water or methanol, and the precipitate formed may be washed with water or dilute alkaline water. The imide compound can also be obtained in solid form by drying.

The novel imide compound according to the present invention cures when heated. At this time, it is also possible to add a polymerization initiator as appropriate.

Suitable polymerization initiators include organic peroxides such as benzoyl peroxide, dicumyl peroxide, lauroyl peroxide, and cumene hydroperoxide, cobalt naphthenate, cobalt acetate, and cobalt acetylacetonate, and usually imide compounds. 0.001 to 100 parts by weight
5 parts by weight are used.

Alternatively, it may be cured by addition polymerization with amines.

The amines are not particularly limited, but include 4,4'-diaminodiphenylmethane, 4,4-diaminodiphenyl ether, 3,3'-diaminodiphenyl sulfone, 2.
．． 2-bis[4-(p-aminophenoxy)phenyl]
Propane, 4,4'-bis(p-aminophenoxy)diphenylsulfone, etc. are industrially preferred because they are easily available.

Further, the polyimide having an amino group at the molecular end as exemplified in the production of such an imide compound according to the present invention is also effective in addition polymerization with such an imide compound according to the present invention.

Additionally, polyamines such as aniline formalin resins can also be used.

Furthermore, aliphatic and alicyclic amines can also be used. Specifically, polyalkylenes represented by ethylenediamine, propanediamine, tetramethylenediamine, hexamethylenediamine, 1,4-diaminocyclohexane, 1,3-diaminocyclohexane, isophoronediamine, 4,4'-diaminodicyclohexylmethane, and diethylenetriamine. Examples include polyamines.

These amines are used in an amount of about 1 to 1000 parts by weight per 100 parts by weight of the imide compound.

In this case, epoxy resin, vinyl compound,
It is also possible to blend acrylate and cyanate.

The imide compound according to the present invention can be used in combination with a known bismaleimide.

Specifically, such bismaleimides include 4.4'-diaminodiphenylmethane bismaleimide, 3.3-. 5.5”-tetramethyl-4,4-diaminodiphenylmethane bismaleimide, 3.3-.5.
5=-Tetraethyl-4,4--diaminodiphenylmethane bismaleimide, 3.3',5.5''-dimethyl-
4,4-monodiaminodiphenylmethane bismaleimide,
N,N”-benzophenone bismaleimide, N,N”-
Examples include diphenylpropane bismaleimide, 3,3'-diphenylsulfone bismaleimide, and N,N=-diphenyl ether bismaleimide.

By adding the imide compound according to the present invention to these known bismaleimides, it is possible to improve the brittleness of thermoset products, which is a drawback of conventional bismaleimides, and to impart heat resistance.

Curing of the imide compound according to the present invention is usually carried out as follows.

First, a solution is prepared by dissolving the compound and, if necessary, a catalyst, an amine, and a modifier in m-cresol, dimethylformamide, N-methylpyrrolidone, or the like. After applying this solution to the substrate by casting or dipping,
When heated, the solvent is removed and the film is cured. or,
A prepreg can also be prepared by impregnating glass cloth.

The polyimide prepared using the imide compound according to the present invention as a component can be widely used in various fields where conventional polyimides are applied, such as films, materials for laminates, molding materials, wire coating materials, adhesives, and paints. can.

[Example] Hereinafter, the present invention will be explained in detail with reference to Examples.

Example 1 3.3-. 4.4”-diphenylsulfone tetracarboxylic dianhydride (hereinafter abbreviated as rDsDAJ)>35.
8tJ (0.1 mol) and 40.0 g (0.2 mol) of 4.4-diaminodiphenyl ether were dissolved in 420 d of N-methylpyrrolidone and stirred at 25°C for 2 hours. Furthermore, 19.69 (0.2 mol) of maleic anhydride was added and stirred at 25°C for 1 hour. After that, 50 g of acetic anhydride (0
, 5 mol), triethylamine 5 g, cobalt acetate 0.
3 g was added, and the mixture was heated and stirred at 60° C. for 3 hours.

When the reaction was completed, the reaction solution was poured into water to form a precipitate. After washing with 0.5% sodium carbonate aqueous solution and methanol, drying yields yellow polyimide powder 86.
．． I got 19. The elemental analysis results of this substance were as follows.

Actual value Theoretical value C65,265,30 H3,12,97 022,021,75 S 3.4 3.63 N 6.3 6.35 In addition to N-methylpyrrolidone used as a reaction solvent, this substance contains dimethyl Formamide, dimethyl sulfoxide, m-
It was soluble in cresol, but insoluble in solvents such as ethyl carpitol and methyl isobutyl ketone.

When a 30% solution of this substance in dimethylformamide was placed on a glass plate and heated at 140°C for 5 minutes and then at 230°C for 10 minutes, a heat-cured film was obtained, which was no longer compatible with dimethylformamide or N-methylpyrrolidone. was also insoluble.

In addition, 0.6% of this substance was added to a 10% dimethylformamide solution.
When a molar equivalent of diaminodiphenyl ether was added and heated on a glass plate at 230° C. for 2 hours, the mixture was thermoset to become a flexible film. This was also no longer soluble in any solvent such as N-methylpyrrolidone.

Example 2 35.8 g (0.1 mol) of DSDA and 4,4'-diaminodiphenylmethane (hereinafter abbreviated as rDAMJ)>3
9.6 g (0.2 mol) was dissolved in m-cresol 420i and stirred at 25°C for 30 minutes. Furthermore, 19.6 g (0.2 mol) of maleic anhydride was added, and stirring was continued at 25° C. for 30 minutes. To this was added 30 g of phosphoric acid and 50 d of xylene, the temperature was raised until the xylene refluxed, and the mixture was dehydrated with stirring. The refluxing liquid was separated into layers in a decanter and the reaction was continued in the decanter until there were no more separated layers.

The reaction solution thus obtained was poured into water to form a precipitate, which was washed with distilled water, a 0.5% aqueous sodium carbonate solution, and methanol to obtain 84.2 g of a brown solid. This polyimide was easily dissolved in N-methylpyrrolidone, dimethylformamide, and dimethylsulfoxide in addition to m-cresol as a reaction solvent. The results of elemental analysis of the compound were as follows.

Actual value Theoretical value C6B, 2 68.33 H3,63,44 01B, 5 18.20 S 3.5 3.65 N 6.2 6.38 Place a 30% dimethylformamide solution of this substance on a glass plate. When heated at 140°C for 5 minutes and further at 230°C for 10 minutes, a cured film was obtained. It was no longer soluble in coconut methylformamide. Also, 0 on the same wave.
Mix 6 times the molar amount of DAM and heat on a glass plate at 230℃ for 2 hours.
After heating for a period of time, a flexible film was obtained. This film was insoluble in solvents such as N-methylpyrrolidone.

Example 3 35.8 g (0.1 mol) of DSDA and 44.4 g of 4,4-diaminodiphenylsulfone. Og (0°2 mol) and N
- 119.69 g of maleic anhydride (0,2-E
/lz) was added thereto, and the mixture was further stirred at 25°C for 3 hours. 50 g (0.5 mol) of acetic anhydride was added and heated to 150° C. for 3 hours, and all the distilled liquid was taken out of the reaction system.

Furthermore, 10 g (0.1 mol) of acetic anhydride was added and heated to 150°C.
, and stirred for 1 hour. After the reaction was completed, the reaction solution was poured into water to form a precipitate. The mixture was washed with a 0.5% aqueous sodium carbonate solution, washed with methanol, and then dried to obtain 89.2 g of black-brown polyimide powder.

The elemental analysis results of this substance were as follows.

Actual value Theoretical value 0 58.7 58.89 1-1 2.8 2.68 0 23.0 22.89 S 9.9 9.82 N 5.6 5.72 Example 4 DSDA35.89 (0, 10 mol) and DAM23,
8 g (0.12 mol) were stirred at 25° C. in DMF200J until homogeneous. Add to this 3. maleic anhydride.
92 g (0.04 mol) was added and stirred for an additional hour.

50 g (0.50 mol) of acetic anhydride and 159 mol of triethylamine were added to this polyamic acid solution, and the mixture was reacted at 80° C. for 4 hours.

After reaction, triethylamine, acetic acid, and acetic anhydride were removed under reduced pressure. The resulting reaction product was a viscous brown solution.

4.00 g of DAM was dissolved in this solution. This mixed solution was cast with a doctor blade and heated to 140°C.
When the film was heated at 230° C. for 20 hours, a tough film was obtained. This film was no longer soluble in any solvent.

Example 5 35.8 g (0.1 mol) of DSDA and 50.0 g (0.2 mol) of 4,4'-diphenylmethane diisocyanate
was dissolved in 300 ml of m-cresol, 10 g of triethylamine was added thereto, and the mixture was heated at 150°C for 6 hours. After cooling, a solution of 19.6 g (0.2 mol) of maleic anhydride dissolved in 50 ml of m-cresol was added dropwise at 35° C., and
Stirred at that temperature for 1 hour. 24 g of acetic anhydride was added thereto, the temperature was raised to 60° C., and the mixture was reacted for 3 hours, followed by topping under reduced pressure to remove acetic acid and triethylamine.

Furthermore, 15 g of DAM was dissolved to prepare a thermosetting resin solution. This solution was heated on a glass plate at 140″C for 15 minutes.
The film obtained by further heating at 230° C. for 1 hour was insoluble in any solvent.

[Brief explanation of the drawing]

FIG. 1 shows an infrared absorption spectrum of the imide compound obtained in Example 1. FIG. 2 shows an infrared absorption spectrum of the imide compound obtained in Example 2. Patent applicant Shin Nihon Rika Co., Ltd.

Claims (1)

[Claims] 1. An imide compound represented by general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, A is ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲
There are mathematical formulas, chemical formulas, tables, etc. Represents ▼. X is a direct bond, -O-, -S-, -SO_2-, -CO
−, −CH_2CH_2−, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Represents . Y^1,
Y^2 is a hydrogen atom, methyl, ethyl, -Cl, -Br
, -CF_3, -CH_2CF_3 and may be the same or different. R represents each group of methyl, ethyl, isopropyl, methoxy, ethoxy, carboxyl, -Cl, -Br, -OH, and -SO_3H. n is an integer from 1 to 5. ) 2 1 belonging to diphenylsulfone tetracarboxylic acids
Represented by the general formula (I), which is characterized by reacting a species or two or more compounds, an aromatic diamine and/or its isocyanate, and maleic acid or dicarboxylic acids capable of producing maleic acid upon heating. A method for producing an imide compound. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, A is ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲
There are mathematical formulas, chemical formulas, tables, etc. Represents ▼. X is a direct bond, -O-, -S-, -SO_2-, -CO
−, −CH_2CH_2−, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Represents . Y^1,
Y^2 is a hydrogen atom, methyl, ethyl, -Cl, -Br
, -CF_3, -CH_2CF_3 and may be the same or different. R represents each group of methyl, ethyl, isopropyl, methoxy, ethoxy, carboxyl, -Cl, -Br, -OH, and -SO_3H. n is an integer from 1 to 5. )