TWI866665B - Carbonate-containing aromatic amine compound, preparation method thereof, epoxy curable product and poly(carbonate imine) vitirmer prepared thereby and degrading method thereof - Google Patents

Abstract

The present disclosure provides a carbonate-containing aromatic amine compound. The carbonate-containing aromatic amine compound has a structure represented by formula (I) or formula (II), in which each symbol is as defined in the specification. Thus, the carbonate-containing aromatic amine compound is obtained by using the carbonate group reacted with the nitro-containing epoxy group to form the carbonate-containing aromatic nitro compound, and the nitro group is further reduced to the amino group through the hydrogenation. The carbonate-containing aromatic amine compound can be used as the amine curing agent for the epoxy resin, and can react with the aldehyde to prepare the poly(carbonate imine) vitirmer, and the synthesized cured product can be degraded.

Description

Aromatic amine compounds containing carbonate, preparation method thereof, epoxy cured products and poly(carbonate imide) glassy polymer cured products prepared therefrom, and degradation method thereof

The present invention relates to an aromatic amine compound and a preparation method thereof, and in particular to an aromatic amine compound containing carbonate, a preparation method thereof, an epoxy cured product and a poly(carbonate imide) type glassy polymer cured product prepared therefrom, and a degradation method thereof.

Generally speaking, thermosetting materials have excellent thermal stability, chemical stability and high-density covalent bond cross-linking network structure, which makes them difficult to dissolve and decompose for recycling. If there are unstable bonds in the cross-linking network, the cured product will have the potential to be degraded. In recent years, some studies have pointed out that ester groups are chemically degradable and are gradually being applied in PET recycling. Therefore, if similar concepts can be introduced into epoxy resins, there is a chance to improve the degradability of waste and achieve the purpose of chemical recycling.

In addition, recent studies have pointed out that if reversible dynamic bonds exist in the cross-linked structure, bond exchange reactions can occur through external stimuli (such as heating, light, solvents, etc.) to prepare polymer materials with recyclable, self-repairing and reprocessing capabilities. Such polymers are called vitrimers, also known as glassy polymers. Among them, vitrimers containing imine bonds are also called Schiff base vitrimers, which can be synthesized through commercially available aldehydes/ketones and amines. Imine bonds have three reversible reactions, including condensation/hydrolysis, amination transfer and double decomposition reactions, which usually occur under mild reaction conditions and without the addition of catalysts. Therefore, compared with other dynamic covalent bonds, they have higher bond exchange efficiency, making the material have excellent biodegradability, self-healing and reprocessability. It is considered to be a green alternative product that can replace traditional thermosetting composites.

In view of this, how to synthesize biodegradable, self-repairable and recyclable solids has become the goal of relevant industries.

One object of the present invention is to provide a carbonate-containing aromatic amine compound and a preparation method thereof, wherein polycarbonate or carbonate compound is first reacted with an epoxy resin containing a nitro structure to obtain a carbonate-containing aromatic nitro compound, and then the nitro group is reduced to an amine group by a hydrogenation reduction reaction to obtain a carbonate-containing aromatic amine compound.

Another object of the present invention is to provide an epoxy cured product and a degradation method thereof, wherein an aromatic amine compound containing carbonate is used as a hardener and undergoes a curing reaction with an epoxy resin to prepare an epoxy cured product, and the epoxy cured product can be degraded so that the product can be recycled and reused, thereby reducing the environmental burden.

Another object of the present invention is to provide a poly(carbonate imide) glassy polymer cured product and a degradation method thereof, wherein a carbonate-containing aromatic amine compound and an aldehyde compound are subjected to a condensation reaction to prepare a poly(carbonate imide) cured product containing a Schiff base, and the cured product not only has good thermal and mechanical properties, but also has reprocessable and degradable recycling characteristics, which conforms to the concept of circular economy.

One embodiment of the present invention provides a carbonate-containing aromatic amine compound having a structure as shown in formula (I) or formula (II): Formula (I), Formula (II), Wherein, R ₁ , R ₂ , R ₃ and R ₄ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an allyl group, an alkoxy group having 1 to 6 carbon atoms, an aromatic group having 6 to 12 carbon atoms or a halogen atom, a and b are each independently an integer from 0 to 4, and c and d are each independently an integer from 0 to 5. X is a single bond, a cycloalkyl group having 3 to 12 carbon atoms, or a structure represented by formula (a), formula (b), formula (c), formula (d), formula (e), formula (f), formula (g), formula (h) or formula (i): Formula (a), Formula (b), Formula (c), Formula (d), Formula (e), Formula (f), Formula (g), Formula (h), Formula (i), Wherein, _X1 and _X2 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aromatic group having 6 to 12 carbon atoms. Y is each independently an aromatic group having 6 to 18 carbon atoms, the aromatic group is unsubstituted or substituted with at least one substituent, and the at least one substituent is an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aromatic group having 6 to 12 carbon atoms, and the number of the at least one substituent is an integer from 1 to 4. q is an integer from 1 to 4, n is the degree of polymerization, and 1 ≤ n ≤ 500.

Another embodiment of the present invention provides a method for preparing a carbonate-containing aromatic amine compound, comprising a synthesis step and a catalytic reduction step. The synthesis step is to mix a structure as shown in formula (A1) or formula (A2) with a structure as shown in formula (B), and then react in a first catalyst or without a catalyst to synthesize a structure as shown in formula (C1) or formula (C2): Formula (A1), Formula (A2), Formula (B), Formula (C1), Formula (C2). The catalytic reduction step is to reduce the structure shown in formula (C1) or formula (C2) under the catalysis of a second catalyst to obtain a carbonate-containing aromatic amine compound having a structure shown in formula (I) or formula (II): Formula (I), Formula (II), Wherein, R ₁ , R ₂ , R ₃ and R ₄ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an allyl group, an alkoxy group having 1 to 6 carbon atoms, an aromatic group having 6 to 12 carbon atoms or a halogen atom, a and b are each independently an integer from 0 to 4, and c and d are each independently an integer from 0 to 5. X is a single bond, a cycloalkyl group having 3 to 12 carbon atoms, or a structure represented by formula (a), formula (b), formula (c), formula (d), formula (e), formula (f), formula (g), formula (h) or formula (i): Formula (a), Formula (b), Formula (c), Formula (d), Formula (e), Formula (f), Formula (g), Formula (h), Formula (i); Wherein, _X1 and _X2 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aromatic group having 6 to 12 carbon atoms. Y is each independently an aromatic group having 6 to 18 carbon atoms, the aromatic group is unsubstituted or substituted with at least one substituent, and the at least one substituent is an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aromatic group having 6 to 12 carbon atoms, and the number of the at least one substituent is an integer from 1 to 4. q is an integer from 1 to 4, n is the degree of polymerization, and 1 ≤ n ≤ 500.

According to the preparation method of the carbonate-containing aromatic amine compound described in the previous paragraph, the first catalyst can be selected from the group consisting of 4-dimethylaminopyridine, imidazole, pyridine, 2-methylimidazole, 3-methylimidazole, 2-ethyl-4-methylimidazole, 2-methylpyridine, 3-methylpyridine, tetra-n-butylammonium bromide, and tetrabutylammonium chloride.

According to the preparation method of the carbonate-containing aromatic amine compound described in the previous paragraph, the amount of the first catalyst added can be 0.1 weight percent to 5 weight percent of the structure content shown in formula (B).

According to the preparation method of the carbonate-containing aromatic amine compound described in the preceding paragraph, the equivalent ratio of the epoxy group in the structure shown in formula (B) to the carbonate group in the structure shown in formula (A1) or formula (A2) can be 1.3 to 10.0.

According to the preparation method of the carbonate-containing aromatic amine compound described in the previous paragraph, the second catalyst can be a palladium-carbon catalyst, and the added amount of the second catalyst can be 0.1 weight percent to 5 weight percent of the structure content shown in formula (C1) or formula (C2).

Another embodiment of the present invention provides an epoxy cured product, which is obtained by a curing reaction between the aforementioned carbonate-containing aromatic amine compound and an epoxy resin.

Another embodiment of the present invention provides a method for degrading epoxy cured material, comprising providing the aforementioned epoxy cured material and performing a degradation step. The degradation step is to react an amine-containing compound with the epoxy cured material to degrade the epoxy cured material.

Another embodiment of the present invention provides a poly(carbonate imide) glassy polymer cured product, which is obtained by a curing reaction of the aforementioned carbonate-containing aromatic amine compound and an aldehyde compound.

Another embodiment of the present invention provides a method for degrading a poly(carbonate imide) glassy polymer solidified material, comprising providing the aforementioned poly(carbonate imide) glassy polymer solidified material and performing a degradation step. The degradation step is to react a sulfuric acid mixed solution with the poly(carbonate imide) glassy polymer solidified material to degrade the poly(carbonate imide) glassy polymer solidified material.

Thus, the carbonate-containing aromatic amine compound of the present invention is firstly prepared by mixing an aromatic carbonate-containing structure with an epoxy resin containing a nitro structure, and then obtaining a carbonate-containing aromatic nitro compound under catalysis or without a catalyst, and then reducing the nitro group to an amine group through a hydrogenation reduction reaction to prepare a carbonate-containing aromatic amine compound, which can be subsequently applied to epoxy resin hardeners or to prepare poly(carbonate imide) glassy polymer cured products. The cured products obtained by the above applications not only have excellent properties, but can also be degraded so that they can be recycled and reused, which is in line with environmental protection benefits.

The following will discuss various embodiments of the present invention in more detail. However, this embodiment can be an application of various inventive concepts and can be specifically implemented in various different specific scopes. The specific embodiment is for illustrative purposes only and is not limited to the scope of the disclosure.

In the present invention, the compound structure is sometimes represented by a skeleton formula, which may omit carbon atoms, hydrogen atoms, and carbon-hydrogen bonds. If the functional groups are clearly drawn in the structural formula, the drawn functional groups shall prevail.

In the present invention, "a carbonate-containing aromatic amine compound having a structure as shown in formula (I)" is sometimes expressed as a carbonate-containing aromatic amine compound shown in formula (I) or a carbonate-containing aromatic amine compound (I) for the sake of simplicity and fluency, and other compounds or groups may be expressed in the same manner.

＜Carbonate-containing aromatic amine compounds＞

The present invention provides a carbonate-containing aromatic amine compound having a structure as shown in formula (I) or formula (II): Formula (I), Formula (II), Wherein, R ₁ , R ₂ , R ₃ and R ₄ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an allyl group, an alkoxy group having 1 to 6 carbon atoms, an aromatic group having 6 to 12 carbon atoms or a halogen atom, a and b are each independently an integer from 0 to 4, and c and d are each independently an integer from 0 to 5. X is a single bond, a cycloalkyl group having 3 to 12 carbon atoms, or a structure represented by formula (a), formula (b), formula (c), formula (d), formula (e), formula (f), formula (g), formula (h) or formula (i): Formula (a), Formula (b), Formula (c), Formula (d), Formula (e), Formula (f), Formula (g), Formula (h), Formula (i), Wherein, _X1 and _X2 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aromatic group having 6 to 12 carbon atoms. Y is each independently an aromatic group having 6 to 18 carbon atoms, the aromatic group is unsubstituted or substituted with at least one substituent, and the at least one substituent is an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aromatic group having 6 to 12 carbon atoms, and the number of the at least one substituent is an integer from 1 to 4. q is an integer from 1 to 4, n is the degree of polymerization, and 1 ≤ n ≤ 500.

Thus, the carbonate-containing aromatic amine compound of the present invention can be applied to epoxy resin hardeners, and the carbonate structure can enhance the degradability of epoxy cured products. In addition, the carbonate-containing aromatic amine compound of the present invention can also be applied to the preparation of poly (carbonate imine) glassy polymer cured products, which can undergo bond exchange reactions under external stimuli (such as heating, light, and solvents) through dynamic imine bonding, and have the characteristics of being recyclable, self-repairing, and reprocessable.

<Method for preparing carbonate-containing aromatic amine compounds>

Referring to FIG. 1 , a flow chart of a method 100 for preparing a carbonate-containing aromatic amine compound according to an embodiment of the present invention is shown. In FIG. 1 , the method 100 for preparing a carbonate-containing aromatic amine compound comprises steps 110 and 120.

Step 110 is a synthesis step, which is to mix a structure represented by formula (A1) or formula (A2) with a structure represented by formula (B), and then react them in the presence of a first catalyst or without a catalyst to synthesize a structure represented by formula (C1) or formula (C2): Formula (A1), Formula (A2), Formula (B), Formula (C1), Formula (C2). For the definitions of R ₁ , R ₂ , R ₃ , R ₄ , X, Y, a, b, c, d, q and n, please refer to the above and will not be further elaborated here.

Specifically, the structures represented by formula (A1) and formula (A2) are structures containing aromatic carbonate groups, which may be, but are not limited to, carbonate compounds, new carbonate plastics or polycarbonate recycled materials. Waste polycarbonate recycled materials can be recycled from waste optical discs to reduce environmental burdens, and the structure represented by formula (B) is an epoxy resin containing a nitro structure.

In addition, the structures represented by formula (C1) and formula (C2) are carbonate-containing aromatic nitro compounds, and the equivalent ratio of the epoxy group in the nitro-containing epoxy resin represented by the aforementioned formula (B) to the carbonate group in the structure containing an aromatic carbonate group represented by formula (A1) or formula (A2) can be 1.3 to 10.0, preferably 2.0 to 10.0.

Specifically, when the structure containing an aromatic carbonate group is a structure shown in formula (A1), the synthesized carbonate-containing aromatic nitro compound is a structure shown in formula (C1), and the reaction equation is shown in Table 1 below. Table 1

In addition, when the structure containing an aromatic carbonate group is a structure shown in formula (A2), the synthesized carbonate-containing aromatic nitro compound is a structure shown in formula (C2), and the reaction equation is shown in Table 2 below. Table 2

The first catalyst may include an unshared electron pair, which may be selected from a group consisting of 4-dimethylaminopyridine (DMAP), imidazole, pyridine, 2-methylimidazole, 3-methylimidazole, 2-ethyl-4-methylimidazole, 2-picoline, 3-picoline, tetrabutylammonium bromide, and tetrabutylammonium chloride. Thus, the unshared electron pair of the first catalyst may react with the epoxy group in the nitro-containing epoxy resin of the formula (B) to facilitate the synthesis reaction. Specifically, the amount of the first catalyst added can be 0.1 weight percent to 5 weight percent of the content of the nitro-containing epoxy resin shown in the formula (B). In addition, step 110 of the present invention can also be reacted without adding a catalyst.

Step 120 is a catalytic reduction step, which is to reduce the structure shown in formula (C1) or formula (C2) under the catalysis of a second catalyst to obtain a carbonate-containing aromatic amine compound having a structure shown in formula (I) or formula (II): Formula (I), Formula (II). For the definitions of R ₁ , R ₂ , R ₃ , R ₄ , X, Y, a, b, c, d, q and n, please refer to the above and will not be further elaborated here.

Specifically, when the carbonate-containing aromatic nitro compound has a structure shown in formula (C1), the carbonate-containing aromatic amine compound synthesized therefrom has a structure shown in formula (I), and the reaction equation is shown in Table 3 below. Table 3

In addition, when the carbonate-containing aromatic nitro compound has a structure represented by formula (C2), the carbonate-containing aromatic amine compound synthesized therefrom has a structure represented by formula (II), and the reaction equation is shown in Table 4 below. Table 4

The second catalyst may be a palladium-carbon catalyst, and its addition amount may be 0.1 weight percent to 5 weight percent of the content of the carbonate-containing aromatic nitro compound represented by the formula (C1) or (C2).

＜Epoxy Cured Products＞

The present invention further provides an epoxy cured product, which is obtained by a curing reaction between the aforementioned carbonate-containing aromatic amine compound and an epoxy resin, and the aforementioned curing reaction is briefly described below with reference to FIG. 2, wherein FIG. 2 shows a step flow chart of a method 200 for preparing an epoxy cured product according to another embodiment of the present invention. In FIG. 2, the method 200 for preparing an epoxy cured product includes step 210 and step 220.

Step 210 is a mixing step, which is to use the carbonate-containing aromatic amine compound as a hardener and mix it with the epoxy resin to obtain a curable composition. Specifically, through step 210, the carbonate-containing aromatic amine compound and the epoxy resin can form a precursor solution containing the curable composition. In addition, the solvent used in the precursor solution is used to help the carbonate-containing aromatic amine compound and the epoxy resin blend. Therefore, as long as it can dissolve the carbonate-containing aromatic amine compound and the epoxy resin and does not react with the above two, it can be used as the solvent in step 210.

Step 220 is to perform a curing step to crosslink the carbonate-containing aromatic amine compound with the epoxy resin to form an epoxy cured product. Specifically, the curable composition can be directly ground into powder and heated to a molten state or the precursor solution can be heated to crosslink the carbonate-containing aromatic amine compound with the epoxy resin, and the final heating curing temperature can be 80 ^° C to 240 ^° C, preferably 180 ^° C to 240 ^° C, and the heating time can be 1 hour to 6 hours. More specifically, the aforementioned heating method can adopt a multi-stage heating curing method, for example, heating at 180 ^° C, 200 ^° C, and 220 ^° C for 2 hours each. The curing temperature and heating time can be flexibly adjusted according to the types of carbonate-containing aromatic amine compounds and epoxy resins used, but the present invention is not limited thereto.

＜Methods for degrading epoxy cured products＞

Please refer to FIG. 3 , which is a flow chart showing a method 300 for degrading epoxy cured products according to another embodiment of the present invention. In FIG. 3 , the method 300 for degrading epoxy cured products includes step 310 and step 320 .

Step 310 is to provide the aforementioned epoxy curing material. Step 320 is to perform a degradation step, which is to react an amine-containing compound with the aforementioned epoxy curing material to degrade the epoxy curing material.

＜Poly(carbonate imide) glassy polymer cured product＞

The present invention further provides a poly(carbonate imide) glassy polymer cured product, which is obtained by a curing reaction between the aforementioned carbonate-containing aromatic amine compound and an aldehyde compound, and the aforementioned curing reaction is briefly described below with reference to FIG. 4, wherein FIG. 4 shows a step flow chart of a method 400 for preparing a poly(carbonate imide) glassy polymer cured product according to another embodiment of the present invention. In FIG. 4, the method 400 for preparing a poly(carbonate imide) glassy polymer cured product includes steps 410 and 420.

Step 410 is a mixing step, which is to mix the carbonate-containing aromatic amine compound with the aldehyde compound to obtain a curable composition. Specifically, through step 410, the carbonate-containing aromatic amine compound and the aldehyde compound can form a precursor solution containing the curable composition. In addition, the solvent used in the precursor solution is used to help the carbonate-containing aromatic amine compound and the aldehyde compound blend. Therefore, as long as it can dissolve the carbonate-containing aromatic amine compound and the aldehyde compound and does not react with the above two, it can be used as the solvent in step 410.

Step 420 is to perform a curing step to crosslink the carbonate-containing aromatic amine compound and the aldehyde compound to form a poly(carbonate imide) glassy polymer cured product. Specifically, the curable composition can be directly ground into powder and heated to a molten state or the precursor solution can be heated to crosslink the carbonate-containing aromatic amine compound and the aldehyde compound, and the final heating curing temperature can be 80 ^° C to 240 ^° C, preferably 180 ^° C to 240 ^° C, and the heating time can be 1 hour to 6 hours. More specifically, the aforementioned heating method can adopt a multi-stage heating curing method, for example, heating at 180 ^° C, 200 ^° C, and 220 ^° C for 2 hours each. The curing temperature and heating time can be flexibly adjusted according to the types of carbonate-containing aromatic amine compounds and aldehyde compounds used, but the present invention is not limited thereto.

<Method for degrading poly(carbonate imide) type glassy polymer cured product>

Please refer to FIG. 5 , which is a flow chart showing a method 500 for degrading a poly(carbonate imide) glassy polymer solidified material according to another embodiment of the present invention. In FIG. 5 , the method 500 for degrading a poly(carbonate imide) glassy polymer solidified material comprises step 510 and step 520.

Step 510 is to provide the aforementioned poly(carbonate imide) glassy polymer cured product. Step 520 is to perform a degradation step, which is to react a sulfuric acid mixed solution with the aforementioned poly(carbonate imide) glassy polymer cured product to degrade the poly(carbonate imide) glassy polymer cured product.

The present invention is further illustrated by the following specific embodiments, which are used to facilitate those skilled in the art to which the present invention belongs, so that the present invention can be fully utilized and practiced without excessive interpretation. These embodiments should not be regarded as limiting the scope of the present invention, but are used to illustrate the materials and methods for implementing the present invention.

＜Synthesis Example＞

＜Preparation of Epoxy Resin Containing Nitro Group＞

Synthesis Example 1: 10.00 g of p-nitrophenol and 26.60 g of epichlorohydrin were placed in a 100 ml three-neck flask, and the two were heated to 80 ^° C to confirm dissolution at a molar ratio of 1:4, and then 0.46 g of tetra-n-butylammonium bromide (TBAB) was added and reacted for 3 hours. After the reaction was completed, 50 weight percent sodium hydroxide aqueous solution was added dropwise in an ice bath environment and the reaction continued for 5 hours. After the reaction was completed, the mixture was poured into water for precipitation and washed with water several times to obtain the nitro-containing epoxy resin of Synthesis Example 1. Thereafter, the product obtained according to Synthesis Example 1 was subjected to spectral analysis. The data of hydrogen spectrum: ¹ H-NMR (DMSO-d ₆ ), δ= 2.74 (1H, H ⁹ ), 2.87 (1H, H ⁹ ), 3.38 (1H, H ⁸ ), 3.99 (1H, H ⁷ ), 4.50 (1H, H ⁷ ), 7.17 (2H, H ³ , H ⁵ ), 8.18 (2H, H ² , H ⁶ ); the data of carbon spectrum: ¹³ C-NMR (DMSO-d ₆ ), δ= 43.71 (C ⁹ ), 49.35 (C ⁸ ), 69.84 (C ⁷ ), 115.06 (C ³ , C ⁵ ), 125.82 (C ² , C ⁶ ）、141.03 (C ¹ ）、163.46 (C ⁴ ）。 FTIR (KBr, cm ^-1 ) : ν = 910 (epoxide group), 1347 (N = O nitro group). The reaction equation of Synthesis Example 1 is shown in Table 5 below. Table 5

＜Preparation of Aromatic Nitro Compounds Containing Carbonate＞

Synthesis Example 2: 3.0 g of diphenyl carbonate and 5.47 g of Synthesis Example 1 were placed in a 100 ml three-neck flask, and the two were heated to 160 ^° C at a molar ratio of 1:2 to confirm that they were dissolved, and then 0.027 g of 4-dimethylaminopyridine was added and reacted for 4 hours; alternatively, the reaction can be carried out in a closed environment without adding any catalyst for 4 hours to obtain the carbonate-containing aromatic nitro compound of Synthesis Example 2. Then, the product obtained in Synthesis Example 2 was subjected to spectral analysis. The data of hydrogen spectrum were: ¹ H-NMR (DMSO-d ₆ ), δ= 4.21-4.59 (4H, H ⁷ , H ⁹ ), 5.25-5.42 (2H, H ⁸ ), 6.88-6.98 (6H, H ¹ , H ³ , H ⁵ ), 7.13-7.24 (4H, H ¹¹ , H ¹³ ), 7.24-7.30 (4H, H ² , H ⁴ ), 8.13-8.21 (4H, H ¹² , H ¹⁴ ); the data of carbon spectrum were: ¹³ C-NMR (DMSO-d ₆ ), δ= 65.64-67.12 (C ⁷ , C ⁹ ）、74.36 (C ⁸ ）、114.48 (C ³ ，C ⁵ ）、115.17 (C ¹¹ ，C ¹³ ）、121.15 (C ¹ ）、125.70 (C ¹² ，C ¹⁴ ）、129.51 (C ² ，C ⁴ ）、141.10 (C ¹⁵ ）、153.70 (C ¹⁶ ）、157.88 (C ⁶ ）、163.12 (C ¹⁰ ）。 FTIR (KBr, cm ^-1 ) : ν = 1341 (N = O nitro group), 1754 (C = O carbonate group). The reaction equation of Synthesis Example 2 is shown in Table 6 below. Table 6

Synthesis Example 3: 10.0 g of polycarbonate and 15.37 g of Synthesis Example 1 were placed in a 100 ml three-neck flask, and the two were heated to 150 ^° C to confirm dissolution at a molar ratio of 1:2, and then 0.077 g of 4-dimethylaminopyridine was added and reacted for 4 hours; or, the reaction can be carried out in a closed environment without adding any catalyst for 4 hours. After the reaction is completed, the mixture is dissolved back into dimethylacetamide and precipitated in hot ethanol, and washed several times with hot ethanol to obtain the aromatic nitro compound containing carbonate in Synthesis Example 3. Afterwards, the product obtained according to Synthesis Example 3 was subjected to spectral analysis. The data of hydrogen spectrum were: ¹ H-NMR (DMSO-d ₆ ), δ= 1.49 (6H, H ¹⁴ ), 4.23-4.47 (8H, H ⁷ , H ¹⁰ ), 5.36 (2H, H ⁸ ), 6.80 (4H, H ¹² , H ¹⁸ ), 7.01 (4H, H ¹³ , H ¹⁷ ), 7.11-7.19 (4H, H ³ , H ⁵ ), 8.12 (4H, H ² , H ⁶ ); the data of carbon spectrum were: ¹³ C-NMR (DMSO-d ₆ ), δ= 30.57 (C ¹⁴ ), 41.14 (C ¹⁶ ), 65.85, 66.98 (C ⁷ , C ¹⁰ ), 74.34 (C ⁸ ), 113.95 (C ¹² , C ¹⁸ ), 115.06 (C ³ , C ⁵ ), 125.76 (C ² , C ⁶ ), 127.39 (C ¹³ , C ¹⁷ ), 141.14 (C ¹ ), 143.14 (C ¹⁵ ), 153.64 (C ⁹ ), 155.66 (C ¹¹ ), 163.10 (C ⁴ ); infrared spectrum data: FTIR (KBr, cm ^-1 ): ν= 1341 (N=O nitro group), 1752 (C=O carbonate group). The reaction equation of Synthesis Example 3 is shown in Table 7 below. Table 7

<Example>

＜Preparation of Carbonate-Containing Aromatic Amine Compounds＞

Example 1: 5.0 g of Synthesis Example 2, 0.1 g of palladium-carbon catalyst and 30 ml of tetrahydrofuran were placed in a hydrogenation reactor, and hydrogen at a pressure of 140 psi was introduced, and the reaction was carried out at 25 ^° C. until the hydrogen pressure value no longer decreased. After the reaction was completed, the mixture was filtered through diatomaceous earth to remove the palladium-carbon catalyst, and the filtrate was vortexed and concentrated to remove the solvent, thereby obtaining the carbonate-containing aromatic amine compound of Example 1. Then, the product obtained according to Example 1 was subjected to spectral analysis. The data of hydrogen spectrum: ¹ H-NMR (DMSO-d ₆ ): δ= 4.0-4.30 (8H, H ⁷ , H ⁹ ), 4.59-4.69 (4H, H ¹⁶ ), 5.15-5.25 (2H, H ⁸ ), 6.38-6.50 (4H, H ¹¹ , H ¹³ ), 6.59-6.67 (4H, H ¹² , H ¹⁴ ), 6.85-6.98 (6H, H ¹ , H ³ , H ⁵ ), 7.17-7.32 (4H, H ² , H ⁴ ); the data of carbon spectrum: ¹³ C-NMR (DMSO-d ₆ ): δ= 65.93 (C ⁷ , C ⁹ ), 66.78 (C ⁷ , C ⁹ ), 74.53 (C ⁸ ), 114.55 (C ³ , C ⁵ ), 114.82 (C ¹¹ , C ¹³ ), 115.67 (C ¹² , C ¹⁴ ), 121.01 (C ¹ ), 129.51 (C ² , C ⁴ ), 142.96 (C ¹⁵ ), 113.75 (C ¹⁰ ), 153.81 (C ¹⁷ ), 157.96 (C ⁶ ); infrared spectrum data: FTIR (KBr, cm ^-1 ): ν= 1748 (C=O ester group), 3400-3540 (NH stretching). The reaction equation of Example 1 is shown in Table 8 below. Table 8

Example 2: 10.0 g of Synthesis Example 3, 0.3 g of palladium-carbon catalyst and 50 ml of dimethylformamide were placed in a hydrogenation reactor, and hydrogen at a pressure of 140 psi was introduced, and the reaction was carried out at 40 ^° C until the hydrogen pressure value no longer decreased. After the reaction was completed, the mixture was filtered through diatomaceous earth to remove the palladium-carbon catalyst, and the filtrate was precipitated in water and washed with water several times to obtain the carbonate-containing aromatic amine compound of Example 2. Then, the product obtained according to Example 2 was subjected to spectral analysis. The data of hydrogen spectrum were: ¹ H-NMR (DMSO-d ₆ ): δ= 1.51 (6H, H ¹⁴ ), 4.07-4.22 (8H, H ⁷ , H ¹⁰ ), 4.61 (4H, H ¹⁹ ), 5.22 (2H, H ⁸ ), 6.48 (4H, H ³ , H ⁵ ), 6.64 (4H, H ² , H ⁶ ), 6.80 (4H, H ¹² , H ¹⁸ ), 7.03 (4H, H ¹³ , H ¹⁷ ); the data of carbon spectrum were: ¹³ C-NMR (DMSO-d ₆ ): δ= 30.83 (C ¹⁴ ), 41.33 (C ¹⁶ ）、66.25、66.94 (C ⁷ ，C ¹⁰ ）、74.87 (C ⁸ ）、114.15 (C ¹² ，C ¹⁸ ）、115.13 (C ³ ，C ⁵ ）、115.84 (C ² ，C ⁶ ）、127.63 (C ¹³ ，C ¹⁷ ）、143.01 (C ¹ ）、143.28 (C ¹⁵ ）、149.48 (C ⁴ ）、153.99 (C ⁹ ）、155.91 (C ¹¹ ）。 FTIR (KBr, cm ^-1 ) : ν = 1752 (C=O carbonate group), 3300-3500 (NH stretching). The reaction equation of Example 2 is shown in Table 9 below. Table 9

¹ H-NMR analysis was performed on Synthesis Examples 1 to 3 and Examples 1 to 2 to confirm their structures. Please refer to Figures 6, 7, 8, 9 and 10, wherein Figure 6 shows the ¹ H-NMR spectrum of Synthesis Example 1, Figure 7 shows the ¹ H-NMR spectrum of Synthesis Example 2, Figure 8 shows the ¹ H-NMR spectrum of Synthesis Example 3, Figure 9 shows the ¹ H-NMR spectrum of Example 1, and Figure 10 shows the ¹ H-NMR spectrum of Example 2. It can be seen from the results of Figures 6 to 10 that the spectra of the products synthesized by the present invention are all correct.

＜Preparation of epoxy cured products＞

Examples 3 to 5: The carbonate-containing aromatic amine compound synthesized in Example 1 was used as a hardener and mixed with equal amounts of epoxy resins DGEBA, HP7200 and CNE resin in a solution with a solid content of 25 wt% until completely dissolved. The mixture was poured into a mold and placed in an oven and heated to 180 ^° C for two hours, 200 ^° C for two hours and 220 ^° C for two hours for curing. The epoxy cured products of Examples 3 to 5 were obtained respectively.

Examples 6 to 8: The carbonate-containing aromatic amine compound synthesized in Example 2 was used as a hardener and mixed with equal amounts of epoxy resins DGEBA, HP7200 and CNE resin in a solution with a solid content of 25 wt% until completely dissolved. The mixture was poured into a mold and placed in an oven and heated to 180 ^° C for two hours, 200 ^° C for two hours and 220 ^° C for two hours for curing. The epoxy cured products of Examples 6 to 8 were obtained respectively.

In addition, commercially available aromatic amine-type hardener diaminodiphenylmethane (DDM) was mixed with equal amounts of epoxy resins DGEBA, HP7200, and CNE resin in a solution having a solid content of 25 wt% until completely dissolved, and the same curing steps as in Examples 3 to 8 were performed to obtain epoxy cured products of Comparative Examples 1 to 3.

The epoxy resin and hardener used in Examples 3 to 8 and Comparative Examples 1 to 3 are shown in Table 10 below. Table 10 Hardener Epoxy Embodiment 3 Embodiment 1 DGEBA Embodiment 4 HP7200 Embodiment 5 CNE Embodiment 6 Embodiment 2 DGEBA Embodiment 7 HP7200 Embodiment 8 CNE Comparison Example 1 DDM DGEBA Comparison Example 2 HP7200 Comparison Example 3 CNE

＜Thermal property evaluation＞

Thermal properties of Examples 3 to 8 and Comparative Examples 1 to 3 were evaluated, including glass transition temperature (T _g ), 5% heat loss temperature (T _d5% ), and coke residue. The evaluation method is as follows.

(i) Glass transition temperature: A dynamic mechanical analyzer (DMA) was used to measure the storage modulus and the relationship between the Tan delta curve and temperature, as well as the glass transition temperature and crosslinking density of the epoxy cured products prepared in Examples 3 to 8 and Comparative Examples 1 to 3. In addition, a thermomechanical analysis (TMA) was used to measure the glass transition temperature. The conditions of the thermomechanical analysis method were measured at a heating rate of 5 ^° C/min.

(ii) 5% thermogravimetric loss temperature and char yield: Thermo-Gravimetric Analysis (TGA) was used to measure the 5% thermogravimetric loss temperature and char yield at 800 ^° C of the sample. The thermogravimetric analysis was performed under a nitrogen atmosphere at a heating rate of 20 ^° C/min, using a thermogravimetric analyzer to measure the weight change of the sample. The 5% thermogravimetric loss temperature refers to the temperature at which the weight loss of the cured sample reaches 5%. The higher the 5% thermogravimetric loss temperature, the better the thermal stability of the sample. The coke residue at 800 ^o C refers to the residual weight ratio of the sample when the heating temperature reaches 800 ^o C. The higher the residual weight ratio at 800 ^o C, the better the thermal stability of the sample.

The measurement results of glass transition temperature ( ^° C), storage modulus (GPa), thermal gravimetric loss temperature ( ^° C), coke residue (%) and crosslinking density (mmole/cm ³ ) of Examples 3 to 8 and Comparative Examples 1 to 3 are shown in Table 11 below. Table 11 T _g T _d5% Coke residual rate Storage module Crosslinking density Embodiment 3 124 383 12 1.2 0.11 Embodiment 4 145 365 8 1.4 0.12 Embodiment 5 159 371 17 21.3 1.81 Embodiment 6 157 372 14 33.5 2.86 Embodiment 7 177 380 13 10.6 0.87 Embodiment 8 216 389 twenty two 79.8 6.05 Comparison Example 1 203 384 12 19.0 1.48 Comparison Example 2 217 400 8 8.0 0.61 Comparison Example 3 271 378 17 295.5 20.29

From the results in Table 11, it can be seen that the T _g of epoxy cured products obtained from three different epoxy resins and three different hardeners are DDM, Example 2, and Example 1, from high to low. This is mainly because DDM has a higher reactivity, and because the molecular structures of Examples 2 and 1 are larger, the cross-linking distance is elongated, so the thermal properties are lower than the epoxy cured product obtained with DDM as the hardener. Among them, Example 2 also has a higher T _g because the molecular weight is larger than that of Example 1. In addition, HP7200 and CNE are trifunctional epoxy resins, so the thermal properties of the epoxy cured products obtained are better than DGEBA.

＜Mechanical property evaluation＞

The mechanical properties of Examples 3 to 8 and Comparative Examples 1 to 3 were evaluated by tensile testing to measure tensile strength and elongation at break, wherein the tensile test was measured at room temperature, and the specimen size was 5 cm long, 1 cm wide, and 0.04 to 0.10 mm thick. The measurement results of tensile strength and elongation at break of Examples 3 to 8 and Comparative Examples 1 to 3 are shown in Table 12 below. Table 12 Tensile strength(MPa) Elongation at break (%) Embodiment 3 13.1 3.2 Embodiment 4 15.6 2.7 Embodiment 5 23.7 1.1 Embodiment 6 37.6 0.8 Embodiment 7 38.2 0.8 Embodiment 8 45.7 0.6 Comparison Example 1 23.1 1.0 Comparison Example 2 27.9 1.0 Comparison Example 3 70.4 0.5

From the results in Table 12, it can be seen that the mechanical properties of epoxy cured products obtained from three different epoxy resins and three different hardeners are related to the crosslinking density. When the crosslinking density of the epoxy cured product is higher, the molecular arrangement is more dense, and the tensile strength is higher; on the contrary, when the crosslinking density of the epoxy cured product is lower, the molecular arrangement is looser, so it can show a better elongation at break. In addition, in Comparative Example 3, since the distance between the crosslinking points of epoxy resin CNE and DDM is short, the two can have a high crosslinking density after curing, and CNE is rich in benzene ring structure, so the mechanical strength is the best.

＜Degradation of epoxy cured products＞

Examples 9 to 14 are the results of degradation reactions of epoxy cured products of Examples 3 to 8, respectively, and Comparative Examples 4 to 6 are the results of degradation reactions of epoxy cured products of Comparative Examples 1 to 3, respectively. First, epoxy cured product films of Examples 3 to 8 and Comparative Examples 1 to 3 and 1-hexylamine are placed in a reactor, and after the reaction is completed, a decompression concentrator is used to directly extract 1-hexylamine, and Examples 9 to 14 and Comparative Examples 4 to 6 that have been degraded are obtained. The types of epoxy curing materials, reaction temperatures ( ^° C), reaction times (hrs) and residual weights (%) required in Examples 9 to 14 and Comparative Examples 4 to 6 are listed in Table 13 below. Table 13 Epoxy Curing Reaction temperature Response time Residual weight Embodiment 9 Embodiment 3 125 twenty four 0 Embodiment 10 Embodiment 4 125 twenty four 28 Embodiment 11 Embodiment 5 125 twenty four 55 Embodiment 12 Embodiment 6 125 twenty four 10 Embodiment 13 Embodiment 7 125 twenty four 74 Embodiment 14 Embodiment 8 125 twenty four 95 Comparison Example 4 Comparison Example 1 125 twenty four ＞99 Comparison Example 5 Comparison Example 2 125 twenty four ＞99 Comparison Example 6 Comparison Example 3 125 twenty four ＞99

From the results in Table 13, it can be seen that the epoxy cured products of Examples 9 to 14 of the present invention are degradable after reacting with the compound containing aliphatic amine groups, wherein the residual weight of Example 9 can be 0%, and the residual weight of Example 12 can be 10%. The epoxy cured products made from the commercially available epoxy resins of Comparative Examples 1 to 3 do not degrade even after being extended to 24 hours under the same conditions, and the weight residuals are all greater than 99%. This proves that the carbonate-containing aromatic amine compounds synthesized by the present invention have unique degradability after reacting with epoxy resins, and have a considerable contribution to the recycling and reduction of waste of thermosetting materials.

＜Preparation of poly(carbonate imide) glassy polymer cured products＞

Example 15 and Example 16: The carbonate-containing aromatic amine compound synthesized in Example 2 was mixed with an equal amount of aldehyde compounds, terephthalaldehyde and isophthalaldehyde, in a solution with a solid content of 10 wt% until completely dissolved. The mixture was poured into a mold and placed in an oven and heated to 180 ^° C for two hours and 200 ^° C for two hours for curing. The poly(carbonate imide) glassy polymer cured products of Examples 15 to 16 were obtained respectively.

The carbonate-containing aromatic amine compounds and aldehyde compounds used in Example 15 and Example 16 are shown in Table 14 below. Table 14 Aromatic amine compounds Aldehyde compounds Embodiment 15 Embodiment 2 Terephthalaldehyde Embodiment 16 Isophthalaldehyde

＜Thermal property evaluation＞

The thermal properties of Example 15 and Example 16 were evaluated, and the measurement results of the glass transition temperature ( ^° C), storage modulus (MPa), thermal gravimetric loss temperature ( ^° C) and coke residue (%) are shown in Table 15 below. Table 15 T _g T _d5% Coke residual rate Storage module Embodiment 15 226 375 35 112.7 Embodiment 16 207 383 40 45.1

From the results in Table 15, it can be seen that the T _g of the two different poly(carbonate imide) glassy polymer cured products can reach above 200 ^o C due to their benzene ring-rich structures. Among them, the cured product obtained with terephthalaldehyde as the aldehyde compound has a higher T _g , mainly because the stereo hindrance it causes during polymerization is smaller than that of isophthalaldehyde, so the cross-linking density is higher and has a higher T _g .

＜Mechanical property evaluation＞

The mechanical properties of Example 15 and Example 16 were evaluated, and the measurement results of the tensile strength and elongation at break are shown in Table 16 below. Table 16 Tensile strength(MPa) Elongation at break (%) Embodiment 15 21.6 1.4 Embodiment 16 20.5 2.0

＜Degradation of poly(carbonate imide) glassy polymer cured products＞

The poly(carbonate imide) glassy polymer solidified material of Example 15 and Example 16 and a sulfuric acid mixed solution ( _H2SO4 with THF/ _H2O as _the solution) were placed in a reactor. After the reaction was completed, the sulfuric acid mixed solution was extracted to complete the degradation. The reaction temperature ( ^° C), reaction time (hrs) and residual weight (%) of Example 15 and Example 16 are listed in the following Table 17. Table 17 Reaction temperature Response time Residual weight Embodiment 15 50 36 0 Embodiment 16 50 12 0

From the results in Table 17, it can be seen that both Example 15 and Example 16 can be completely degraded in the sulfuric acid mixed solution. However, Example 15 has a higher crosslinking density, so it takes a longer reaction time to complete the degradation.

In summary, the present invention synthesizes a carbonate-containing aromatic nitro compound and reduces the nitro group to an amine group through a hydrogenation reduction reaction to obtain a carbonate-containing aromatic amine compound. In addition, the carbonate-containing aromatic amine compound of the present invention can be used as an epoxy resin hardener or for preparing poly(carbonate imide) glassy polymer cured products, which not only have excellent properties but can also be degraded to enable recycling, thereby achieving the goal of sustainable utilization.

Although the present invention has been disclosed in the above embodiments, it is not intended to limit the present invention. Anyone skilled in the art can make various changes and modifications without departing from the spirit and scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the scope defined in the attached patent application.

100: Preparation method of carbonate-containing aromatic amine compounds 200: Preparation method of epoxy cured products 300: Method for degrading epoxy cured products 400: Preparation method of poly(carbonate imide) glassy polymer cured products 500: Method for degrading poly(carbonate imide) glassy polymer cured products 110,120,210,220,310,320,410,420,510,520: Steps

In order to make the above and other objects, features, advantages and embodiments of the present invention more clearly understood, the attached drawings are described as follows: FIG. 1 is a step flow chart of a method for preparing a carbonate-containing aromatic amine compound according to one embodiment of the present invention; FIG. 2 is a step flow chart of a method for preparing an epoxy cured product according to another embodiment of the present invention; FIG. 3 is a step flow chart of a method for degrading an epoxy cured product according to yet another embodiment of the present invention; FIG. 4 is a step flow chart of a method for preparing a poly(carbonate imide) glassy polymer cured product according to yet another embodiment of the present invention; FIG. 5 is a step flow chart of a method for degrading a poly(carbonate imide) glassy polymer cured product according to yet another embodiment of the present invention; FIG. 6 is a ¹ H-NMR spectrum of Synthesis Example 1; FIG. 7 is a ¹ H-NMR spectrum of Synthesis Example 2; FIG. 8 is a ¹ H-NMR spectrum of Synthesis Example 3; FIG. 9 is a ¹ H-NMR spectrum of Example 1; and FIG. 10 is a ¹ H-NMR spectrum of Example 2.

100: Preparation method of carbonate-containing aromatic amine compounds

110,120: Steps

Claims (10)

A carbonate-containing aromatic amine compound having a structure as shown in formula (I) or formula (II): Formula (I), Formula (II); wherein R ₁ , R ₂ , R ₃ and R ₄ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an allyl group, an alkoxy group having 1 to 6 carbon atoms, an aromatic group having 6 to 12 carbon atoms, or a halogen atom; a and b are each independently an integer from 0 to 4; and c and d are each independently an integer from 0 to 5; wherein X is a single bond, a cycloalkyl group having 3 to 12 carbon atoms, or a structure represented by formula (a), formula (b), formula (c), formula (d), formula (e), formula (f), formula (g), formula (h) or formula (i): Formula (a), Formula (b), Formula (c), Formula (d), Formula (e), Formula (f), Formula (g), Formula (h), Formula (i); wherein _X1 and _X2 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aromatic group having 6 to 12 carbon atoms; wherein Y is each independently an aromatic group having 6 to 18 carbon atoms, the aromatic group being unsubstituted or substituted with at least one substituent, and the at least one substituent is an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aromatic group having 6 to 12 carbon atoms, and the number of the at least one substituent is an integer from 1 to 4; wherein q is an integer from 1 to 4, and n is the degree of polymerization, and 1 ≤ n ≤ 500. A method for preparing a carbonate-containing aromatic amine compound comprises: performing a synthesis step of mixing a structure represented by formula (A1) or formula (A2) with a structure represented by formula (B), and reacting them in the presence of a first catalyst or without a catalyst to synthesize a structure represented by formula (C1) or formula (C2): Formula (A1), Formula (A2), Formula (B), Formula (C1), Formula (C2); and A catalytic reduction step is performed, wherein the structure represented by formula (C1) or formula (C2) is reduced under the catalysis of a second catalyst to obtain a carbonate-containing aromatic amine compound having a structure represented by formula (I) or formula (II): Formula (I), Formula (II); wherein R ₁ , R ₂ , R ₃ and R ₄ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an allyl group, an alkoxy group having 1 to 6 carbon atoms, an aromatic group having 6 to 12 carbon atoms, or a halogen atom; a and b are each independently an integer from 0 to 4; and c and d are each independently an integer from 0 to 5; wherein X is a single bond, a cycloalkyl group having 3 to 12 carbon atoms, or a structure represented by formula (a), formula (b), formula (c), formula (d), formula (e), formula (f), formula (g), formula (h) or formula (i): Formula (a), Formula (b), Formula (c), Formula (d), Formula (e), Formula (f), Formula (g), Formula (h), Formula (i); wherein _X1 and _X2 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aromatic group having 6 to 12 carbon atoms; wherein Y is each independently an aromatic group having 6 to 18 carbon atoms, the aromatic group being unsubstituted or substituted with at least one substituent, and the at least one substituent is an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aromatic group having 6 to 12 carbon atoms, and the number of the at least one substituent is an integer from 1 to 4; wherein q is an integer from 1 to 4, and n is the degree of polymerization, and 1 ≤ n ≤ 500. A method for preparing a carbonate-containing aromatic amine compound as described in claim 2, wherein the first catalyst is selected from a group consisting of 4-dimethylaminopyridine, imidazole, pyridine, 2-methylimidazole, 3-methylimidazole, 2-ethyl-4-methylimidazole, 2-methylpyridine, 3-methylpyridine, tetra-n-butylammonium bromide, and tetrabutylammonium chloride. A method for preparing a carbonate-containing aromatic amine compound as described in claim 2, wherein the amount of the first catalyst added is 0.1 weight percent to 5 weight percent of the content of the structure represented by formula (B). A method for preparing a carbonate-containing aromatic amine compound as described in claim 2, wherein the equivalent ratio of the epoxy group in the structure represented by formula (B) to the carbonate group in the structure represented by formula (A1) or formula (A2) is 1.3 to 10.0. A method for preparing a carbonate-containing aromatic amine compound as described in claim 2, wherein the second catalyst is a palladium-carbon catalyst, and the amount of the second catalyst added is 0.1 weight percent to 5 weight percent of the structure content represented by formula (C1) or formula (C2). An epoxy cured product is obtained by a curing reaction between the carbonate-containing aromatic amine compound as described in claim 1 and an epoxy resin. A method for degrading an epoxy curing material comprises: Providing an epoxy curing material as described in claim 7; and Performing a degradation step, which is to react an amine-containing compound with the epoxy curing material to degrade the epoxy curing material. A poly(carbonate imide) glassy polymer cured product is obtained by a curing reaction between the carbonate-containing aromatic amine compound as described in claim 1 and an aldehyde compound. A method for degrading a poly(carbonate imide) glassy polymer solidified material, comprising: Providing a poly(carbonate imide) glassy polymer solidified material as described in claim 9; and Performing a degradation step, which is to react a sulfuric acid mixed solution with the poly(carbonate imide) glassy polymer solidified material to degrade the poly(carbonate imide) glassy polymer solidified material.

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