Unsaturated compounds containing carbonate, methods of making the same, cured products made therefrom, and methods of degrading the cured products

Abstract

The present application provides a carbonate-containing unsaturated compound, a preparation method thereof, a cured product prepared therefrom, and a method for degrading the cured product. The carbonate-containing unsaturated compound has one of structures represented by formula (I) or formula (II), wherein each symbol is defined in the specification. Thus, the carbonate-containing unsaturated compound is prepared by reacting a carbonate compound with an epoxy compound or an alcohol compound containing an unsaturated double bond structure, respectively, and the cured product prepared from the carbonate-containing unsaturated compound and a resin has good thermal properties and improved recyclability.

Description

Technical Field

[0001] The present invention relates to an unsaturated compound, a preparation method thereof, a solidified product prepared therefrom and a method for degrading the solidified product, and in particular to an unsaturated compound containing carbonate, a preparation method thereof, a solidified product prepared therefrom and a method for degrading the solidified product. Background Art

[0002] Thermosets offer excellent workability before curing and, after cross-linking and curing, possess excellent thermal stability, mechanical strength, and chemical resistance. Therefore, they are widely used in various fields and are often incorporated into fiber composites that demand high strength and lightweighting. However, due to their inherent non-reprocessability and excellent chemical resistance, thermosets are difficult to recycle and reuse after disposal. Furthermore, the combustion of fiber composites can easily shorten the life of incineration equipment, resulting in significant waste. Therefore, the treatment of discarded thermosets is a key improvement target in today's environmental issues.

[0003] Currently, vinyl ester resins and unsaturated polyester resins are commonly used thermosetting materials in industry. They are widely used in coatings, transportation, construction and other fields. Due to the booming development of the automotive, shipping and other mass transportation industries, their application market continues to expand. For users and developers, the treatment of these resin wastes has become a major issue that they have to face. The industry is eager to learn about technologies that can decompose or recycle these resin wastes for reuse.

[0004] Current research focuses on depolymerization using acidic or alkaline water. This approach, however, leads to subsequent issues such as large amounts of wastewater treatment, making it less environmentally friendly and less suitable for industrial applications. Furthermore, current technology for organic degradation is limited by the limited ester content of the structure, requiring very high degradation temperatures. This leads to energy consumption and poor efficiency, resulting in significant application limitations.

[0005] In view of this, how to synthesize chemically degradable solids and reuse waste has become the goal of relevant industries. Summary of the Invention

[0006] One object of the present invention is to provide an unsaturated compound containing carbonate and a preparation method thereof, wherein the carbonate compound is used as a raw material and is reacted with an epoxy compound or an alcohol compound containing an unsaturated double bond.

[0007] Another object of the present invention is to provide a cured product and a method for degrading the cured product, wherein an unsaturated compound containing a carbonate is subjected to a curing reaction to prepare a cured product, and the cured product can be degraded so that the product can be recycled and reused, thereby reducing the environmental burden.

[0008] One embodiment of the present invention provides an unsaturated compound containing a carbonate, which has a structure as shown in formula (I) or formula (II):

[0009]

[0010] Wherein, X is vinyl, propenyl, acrylic or methacrylic, R1 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group or a halogen atom, and a is an integer from 0 to 5. A is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms or a structure represented by formula (i):

[0011]

[0012] Wherein, R2 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group, or a halogen atom, and b is an integer from 0 to 4. B is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a structure represented by formula (i), or a structure represented by formula (ii) or formula (iii):

[0013]

[0014] R3 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group, or a halogen atom, and c is an integer from 0 to 4. Y is a single bond, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 1 to 12 carbon atoms, an oxygen atom, a sulfur atom, a sulfonyl group, a sulfinyl group, an acyl group, a fluorenyl group, or a hexafluoropropane group. Z is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an o-phenylene group, a m-phenylene group, or a p-phenylene group, and n is an integer from 0 to 10.

[0015] Another embodiment of the present invention provides a method for preparing an unsaturated compound containing a carbonate, comprising providing a carbonate compound, providing a compound containing an unsaturated double bond, and performing a catalytic step. The carbonate compound is dimethyl carbonate or diphenyl carbonate. The unsaturated double bond compound is a monofunctional alcohol compound containing an unsaturated double bond or a monofunctional epoxy compound containing an unsaturated double bond. The catalytic step is to mix the carbonate compound with the unsaturated double bond compound, and then obtain an unsaturated compound containing a carbonate under the catalysis of a catalyst, which has a structure as shown in Formula (I) or Formula (II):

[0016]

[0017] Wherein, X is vinyl, propenyl, acrylic or methacrylic, R1 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group or a halogen atom, and a is an integer from 0 to 5. A is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms or a structure represented by formula (i):

[0018]

[0019] Wherein, R2 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group, or a halogen atom, and b is an integer from 0 to 4. B is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a structure represented by formula (i), or a structure represented by formula (ii) or formula (iii):

[0020]

[0021] R3 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group, or a halogen atom, and c is an integer from 0 to 4. Y is a single bond, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 1 to 12 carbon atoms, an oxygen atom, a sulfur atom, a sulfonyl group, a sulfinyl group, an acyl group, a fluorenyl group, or a hexafluoropropane group. Z is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an o-phenylene group, a m-phenylene group, or a p-phenylene group, and n is an integer from 0 to 10.

[0022] According to the method for preparing unsaturated compounds containing carbonate esters described in the preceding paragraph, the catalyst may be an ionic liquid or an organic base.

[0023] According to the method for preparing the carbonate-containing unsaturated compound described in the preceding paragraph, the equivalent ratio of the carbonate-containing compound to the unsaturated double bond-containing compound may be 0.8 to 1.2.

[0024] Another embodiment of the present invention provides a method for preparing an unsaturated carbonate-containing compound, comprising a catalytic step and an addition step. In the catalytic step, diphenyl carbonate and a difunctional epoxy compound are mixed under a catalyst to obtain a reactant. In the addition step, acrylic acid or methacrylic acid is added to the reactant to obtain an unsaturated carbonate-containing compound having a structure as shown in Formula (II):

[0025]

[0026] Wherein, X is a vinyl group, a propenyl group, an acrylic group, or a methacrylic group; R1 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group, or a halogen atom; and a is an integer from 0 to 5. B is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or a structure represented by formula (i), formula (ii), or formula (iii):

[0027]

[0028]

[0029] Wherein, R2 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group, or a halogen atom, b is an integer from 0 to 4, R3 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group, or a halogen atom, and c is an integer from 0 to 4. Y is a single bond, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 1 to 12 carbon atoms, an oxygen atom, a sulfur atom, a sulfonyl group, a sulfinyl group, an acyl group, a fluorenyl group, or a hexafluoropropane group. Z is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an o-phenylene group, a m-phenylene group, or a p-phenylene group, and n is an integer from 0 to 10.

[0030] According to the method for preparing the carbonate-containing unsaturated compound described in the preceding paragraph, the catalyst may be an organic base, and the equivalent ratio of the bifunctional epoxy compound to diphenyl carbonate may be 2.0 to 8.0.

[0031] Another embodiment of the present invention provides a cured product obtained by subjecting the aforementioned carbonate-containing unsaturated compound to a curing reaction.

[0032] According to the cured product described in the preceding paragraph, the curing reaction is completed by adding the carbonate-containing unsaturated compound to a resin and heating it.

[0033] According to the cured product described in the preceding paragraph, the resin may be an unsaturated polyester resin or a vinyl ester resin.

[0034] According to the cured product described in the preceding paragraph, the added amount of the carbonate-containing unsaturated compound may be 3 weight percent to 20 weight percent of the resin content.

[0035] Another embodiment of the present invention provides a method for degrading a cured product, comprising providing the cured product and performing a degradation step, wherein the degradation step comprises reacting an amine compound with the cured product to degrade the cured product.

[0036] The carbonate-containing unsaturated compound of the present invention can participate in the free radical copolymerization reaction of an unsaturated resin or a vinyl ester resin. By introducing a highly active carbonate structure into the network system, the ester group density of the main structure is increased, and the material is endowed with good degradability. A mild degradation method is also proposed, which can achieve high degradation efficiency without generating wastewater, thereby facilitating industrialization and avoiding the resulting environmental hazards. BRIEF DESCRIPTION OF THE DRAWINGS

[0037] To make the above and other objects, features, advantages and embodiments of the present invention more apparent, the accompanying drawings are described as follows:

[0038] Figure 1 is a flow chart illustrating the steps of a method for preparing an unsaturated compound containing a carbonate ester according to one embodiment of the present invention;

[0039] Figure 2is a flow chart illustrating the steps of a method for preparing an unsaturated compound containing a carbonate according to another embodiment of the present invention;

[0040] Figure 3 is a flowchart illustrating a method for preparing a solidified material according to another embodiment of the present invention; and

[0041] Figure 4 FIG. 4 is a flow chart illustrating the steps of a method for degrading a solidified material according to another embodiment of the present invention. DETAILED DESCRIPTION

[0042] The following will discuss various embodiments of the present invention in more detail. However, this embodiment can be applied to various inventive concepts and can be specifically implemented in various specific scopes. The specific embodiments are for illustrative purposes only and are not intended to limit the scope of the disclosure.

[0043] In this invention, compound structures are sometimes represented using skeleton formulas. This representation may omit carbon atoms, hydrogen atoms, and carbon-hydrogen bonds. If a functional group is explicitly depicted in a structural formula, the depicted group shall prevail.

[0044] In the present invention, "a carbonate-containing unsaturated compound having a structure as shown in formula (I)" may sometimes be expressed as a carbonate-containing unsaturated compound represented by formula (I) or carbonate-containing unsaturated compound (I) for the sake of brevity and fluency. The same may be applied to other compounds or groups.

[0045] <Carbonate-containing unsaturated compound>

[0046] The present invention provides an unsaturated compound containing a carbonate, which has a structure as shown in formula (I) or formula (II):

[0047]

[0048] Wherein, X is a vinyl group, an allyl group, an acrylate group, or a methacrylate group; R1 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group, or a halogen atom; and a is an integer from 0 to 5. A is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or a structure represented by formula (i):

[0049]

[0050] wherein R2 is an alkyl group having a carbon number of 1 to 4, a methoxy group, a nitro group, or a halogen atom, and b is an integer of 0 to 4. B is an alkyl group having a carbon number of 1 to 12, an alkoxy group having a carbon number of 1 to 12, a structure represented by formula (i), a structure represented by formula (ii), or a structure represented by formula (iii):

[0051]

[0052] wherein R3 is an alkyl group having a carbon number of 1 to 4, a methoxy group, a nitro group, or a halogen atom, and c is an integer of 0 to 4. Y is a single bond, an alkyl group having a carbon number of 1 to 12, a cycloalkyl group having a carbon number of 1 to 12, an oxygen atom, a sulfur atom, a sulfonyl group, a thionyl group, a carbonyl group, a fluorene group, or a hexafluoropropane group. Z is an alkyl group having a carbon number of 1 to 12, an alkoxy group having a carbon number of 1 to 12, an ortho-phenylene group, a meta-phenylene group, or a para-phenylene group, and n is an integer of 0 to 10.

[0053] Accordingly, the unsaturated carbonate-containing compound of the present application can be degraded by heat curing, and thus can be recycled in the future.

[0054] Method for preparing unsaturated carbonate-containing compound

[0055] With reference to the accompanying drawings Figure 1 FIG. 1 is a flow chart illustrating a method 100 for preparing an unsaturated carbonate-containing compound according to an embodiment of the present application. Figure 1 In the method 100 for preparing an unsaturated carbonate-containing compound, the method 100 includes a step 110, a step 120, and a step 130.

[0056] The step 110 provides a carbonate-containing compound, which is dimethyl carbonate (DMC) or diphenyl carbonate (DPC).

[0057] The step 120 provides an unsaturated double bond-containing compound, which is a monofunctional alcohol compound containing an unsaturated double bond or a monofunctional epoxy compound containing an unsaturated double bond.

[0058] The step 130 performs a catalytic step, in which the carbonate-containing compound and the unsaturated double bond-containing compound are mixed to obtain an unsaturated carbonate-containing compound having a structure represented by formula (I) or formula (II) under the catalysis of a catalyst:

[0059]

[0060] The definitions of X, A, B, R1 and a are as described above and are not further elaborated here. The catalyst may be an ionic liquid or an organic base.

[0061] See also Figure 2 , which is a flow chart showing the steps of a method 200 for preparing an unsaturated compound containing carbonate according to another embodiment of the present invention. Figure 2 In the method 200 for preparing an unsaturated compound containing carbonate, the method 200 includes steps 210 and 220.

[0062] Step 210 is a catalytic step, wherein diphenyl carbonate and a difunctional epoxy compound are mixed and then catalyzed by a catalyst to obtain a reactant. The catalyst may be an organic base.

[0063] Step 220 is an addition step, in which acrylic acid or methacrylic acid is added to the reactants to obtain an unsaturated compound containing a carbonate ester having a structure as shown in Formula (II):

[0064]

[0065] For the definitions of X, B, R1 and a, please refer to the above and will not be repeated here.

[0066] Specifically, when the carbonate-containing unsaturated compound has a structure represented by formula (I), its preparation method comprises reacting dimethyl carbonate with a monofunctional alcohol compound containing an unsaturated double bond at an equivalent ratio of 0.8 to 1.2, using an ionic liquid as a catalyst, and adding an amount of the catalyst of 0.01 to 2 weight percent of the total reactant content, and the reaction temperature is 60° C. to 90° C.

[0067] In addition, when the unsaturated compound containing carbonate has a structure represented by formula (II), there are two preparation methods. The first preparation method is to react diphenyl carbonate with a monofunctional epoxy compound containing an unsaturated double bond at an equivalent ratio of 0.8 to 1.2, and use an organic base as a catalyst. The amount of the catalyst added is 0.01 to 2 weight percent of the content of the monofunctional epoxy compound containing an unsaturated double bond, and the reaction temperature is 80°C to 140°C. The second preparation method is to react a difunctional epoxy compound with diphenyl carbonate at an equivalent ratio of 2.0 to 8.0, and use an organic base as a catalyst. The amount of the catalyst added is 0.01 to 2 weight percent of the content of the difunctional epoxy compound, and then add acrylic acid or methacrylic acid for reaction, wherein the equivalent ratio of acrylic acid or methacrylic acid to the difunctional epoxy compound is 0.4 to 0.6, and the reaction temperature is 80°C to 140°C.

[0068] <Cured product>

[0069] The present invention further provides a cured product obtained by a curing reaction of the unsaturated compound containing carbonate. Figure 3 A brief description is as follows: Figure 3 A flow chart of a method 300 for preparing a solidified material according to another embodiment of the present invention is shown. Figure 3 In the embodiment, the method 300 for preparing a solidified material includes steps 310 and 320 .

[0070] Step 310 is a mixing step, in which a carbonate-containing unsaturated compound is added to a resin. Specifically, the amount of the carbonate-containing unsaturated compound added is 3 to 20 weight percent of the resin content. This improves the degradability of the cured product without affecting basic physical properties. Details regarding the carbonate-containing unsaturated compound are provided above and are not detailed here. The resin may be, but is not limited to, an unsaturated polyester resin or a vinyl ester resin.

[0071] Step 320 is a curing step, in which the unsaturated carbonate-containing compound and the resin undergo free radical copolymerization to form a cured product. The curing temperature may be between 25°C and 80°C. The curing temperature and heating time can be adjusted flexibly depending on the type of unsaturated carbonate-containing compound and resin used, and the present invention is not limited thereto.

[0072] <Method for Degrading Cured Material>

[0073] See also Figure 4 , which is a flowchart illustrating a method 400 for degrading a solidified material according to another embodiment of the present invention. Figure 4 In the embodiment, the method 400 for degrading a solidified material includes steps 410 and 420 .

[0074] Step 410 provides the aforementioned solidified material. Step 420 involves a degradation step, in which an amine compound reacts with the aforementioned solidified material to degrade the solidified material. Specifically, the degradation step can be performed at 80°C to 150°C without the addition of any catalyst. The degraded liquid can be purified by distillation, the amine compound can be reused, and the resulting urea derivative can be recovered for further use in coatings or polyurethane materials, achieving a recycling goal.

[0075] The present invention is further illustrated by the following specific examples, which are intended to facilitate those skilled in the art to which the present invention relates, so that they can fully utilize and practice the present invention without excessive interpretation. These examples should not be construed as limiting the scope of the present invention, but are intended to illustrate how to implement the materials and methods of the present invention.

[0076] <Examples / Comparative Examples>

[0077] <Preparation of Carbonate-Containing Unsaturated Compound>

[0078] Example 1: 10 g of dimethyl carbonate and 28.89 g of 2-Hydroxyethylmethacrylate (HEMA) were prepared to form a reactant at an equivalent ratio of 1:1. Then, 0.5 weight percent of trioctylmethylphosphonium methylcarbonate (P 8881 CH3OCOO) ionic liquid, and heated to 80°C for 8 hours to obtain the unsaturated compound containing carbonate ester of Example 1 with a yield of about 60%. FTIR spectrum data: 1748 cm -1 (carbonate C=O), 1715cm -1 (acrylate C=O) The reaction equation of Example 1 is shown in Table 1 below.

[0079]

[0080] Example 2: 10 g of diphenyl carbonate and 13.27 g of glycidyl methacrylate (GMA) were mixed at a 1:1 equivalent ratio in a nitrogen atmosphere at 110°C to form a homogeneous solution. 0.027 g of pyridine (0.2 wt% of GMA) was then added and allowed to react for 3 hours to obtain the carbonate-containing unsaturated compound of Example 2 with a yield of approximately 90%. FTIR spectrum data: 1749 cm -1 (aliphatic carbonate C=O)、1715cm -1 (acrylate C=O) The reaction equation of Example 2 is shown in Table 2 below.

[0081]

[0082] Example 3: 10 g of diphenyl carbonate and 34.54 g of bisphenol A epoxy resin (Changchun Synthetic Resin, trade name BE188) were mixed at an equivalent ratio of 1:2 in a nitrogen atmosphere at 110°C to form a homogeneous solution. 0.1727 g of pyridine (0.5 wt% of BE188) was then added and allowed to react for 3 hours. 8.04 g of methacrylic acid was then added at an equivalent ratio of 0.5:1 to BE188, and the mixture was allowed to react for 4 hours to obtain the carbonate-containing unsaturated compound of Example 3. FTIR spectrum data: 1749 cm -1(carbonate C=O), 1719cm -1 (acrylate C=O) The reaction equation of Example 3 is shown in Table 3 below.

[0083]

[0084] <Preparation of Cured Material>

[0085] The carbonate-containing unsaturated compounds of Examples 1 to 3 were added to an unsaturated polyester resin (UP1) or a bisphenol A vinyl ester resin (VE1), respectively, and then diluted with styrene (SM). 1 phr of MEKPO peroxide and 1 phr of cobalt octoate were added. After stirring, the mixture was poured into a mold and cured at room temperature for 12 hours and then at 80°C for 4 hours to obtain the cured products of Examples 4 to 9 and Comparative Examples 1 to 4.

[0086] The formulas and contents used in Examples 4 to 9 and Comparative Examples 1 to 4 are shown in Table 4 below.

[0087]

[0088] <Thermal Property Evaluation>

[0089] Thermal properties of Examples 4 to 9 and Comparative Examples 1 to 4 were evaluated by using a differential scanning calorimeter (DSC) at a heating rate of 10°C / min to measure the glass transition temperature (T g ) and T g (℃) The measurement results are listed in Table 5 below.

[0090]

[0091] The results in Table 5 show that the glass transition temperature of Comparative Example 4 is lower. This is because Example 3 has a larger molecular weight and higher viscosity, and the mixed viscosity increases significantly after addition. Therefore, if the addition ratio of Example 3 is too high, more diluent SM will be required to achieve the required working viscosity, which is detrimental to the physical properties of the cured product. However, Examples 4 to 9 achieve appropriate working viscosities and maintain good glass transition temperatures by adjusting the addition ratio of diluent SM and the carbonate-containing unsaturated compound.

[0092] <Degradable Cured Product>

[0093] The cured products of the present invention can be degraded using amine compounds. First, 0.2 grams of the cured products of Examples 4 to 9 and Comparative Examples 1 to 4 were placed in a container with 4 grams of hexylamine. The mixture was heated in an oven to 130°C for 24 hours. The remaining solids were removed and the residual amount was measured. The residual weight (%) is listed in Table 6 below.

[0094]

[0095] The results in Table 6 show that Examples 4 through 9, by introducing carbonate into the network structure, effectively provide degradation sites, significantly increasing the efficiency of network disintegration, ultimately achieving complete degradation at 130°C without a catalyst. Comparative Examples 1 and 2, which did not include the carbonate-containing unsaturated compound of the present invention, exhibited poor degradation results. While complete degradation was not achieved in Comparative Example 3 due to the low content of carbonate-containing unsaturated compound, a significant improvement in degradability was observed with the addition of the carbonate-containing unsaturated compound of the present invention.

[0096] In summary, the carbonate-containing unsaturated compound of the present invention is prepared by combining a carbonate compound with an epoxy compound or an alcohol compound containing an unsaturated double bond. This compound can be introduced into a commercially available unsaturated polyester resin or vinyl ester resin for curing, imparting biodegradability to the cured product. Furthermore, the compound can be degraded under mild conditions by an amine compound, addressing the issue of thermoset material recycling.

[0097] Although the present invention has been disclosed above in terms of embodiments, this is not intended to limit the present invention. Anyone skilled in the art may make various changes and modifications without departing from the spirit and scope of the present invention. Therefore, the scope of protection of the present invention shall be determined by the scope of the appended patent applications.

[0098] Explanation of symbols

[0099] 100,200: Preparation method of unsaturated compounds containing carbonate

[0100] 300: Preparation method of solidified material

[0101] 400: Method for degrading solidified materials

[0102] 110,120,130,210,220,310,320,410,420: Steps

Claims

1. An unsaturated compound containing a carbonate, characterized in that It has a structure as shown in formula (II): Wherein, X is vinyl, propenyl, acrylic or methacrylic; wherein R1 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group or a halogen atom, and a is an integer from 0 to 5; Wherein, B is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or a structure represented by formula (i), formula (ii), or formula (iii): wherein R2 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group or a halogen atom, and b is an integer from 0 to 4; wherein R3 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group or a halogen atom, and c is an integer from 0 to 4; wherein Y is a single bond, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 1 to 12 carbon atoms, an oxygen atom, a sulfur atom, a sulfonyl group, a sulfinyl group, an acyl group, a fluorenyl group, or a hexafluoropropane group; wherein Z is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an o-phenylene group, a m-phenylene group, or a p-phenylene group; and Here, n is an integer from 0 to 10.

2. A method for preparing an unsaturated compound containing a carbonate, characterized in that: Include: Providing a carbonate-containing compound, which is diphenyl carbonate; Providing a compound containing an unsaturated double bond, which is a monofunctional epoxy compound containing an unsaturated double bond; and A catalytic step is performed, wherein the carbonate-containing compound and the unsaturated double bond-containing compound are mixed under a catalyst to obtain an unsaturated carbonate-containing compound having a structure as shown in formula (II): Wherein, X is vinyl, propenyl, acrylic or methacrylic; wherein R1 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group or a halogen atom, and a is an integer from 0 to 5; Wherein, B is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or a structure represented by formula (i), formula (ii), or formula (iii): wherein R2 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group or a halogen atom, and b is an integer from 0 to 4; wherein R3 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group or a halogen atom, and c is an integer from 0 to 4; wherein Y is a single bond, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 1 to 12 carbon atoms, an oxygen atom, a sulfur atom, a sulfonyl group, a sulfinyl group, an acyl group, a fluorenyl group, or a hexafluoropropane group; wherein Z is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an o-phenylene group, a m-phenylene group, or a p-phenylene group; Here, n is an integer from 0 to 10.

3. The method for preparing an unsaturated compound containing carbonate according to claim 2, wherein The catalyst is an ionic liquid or an organic base.

4. The method for preparing an unsaturated compound containing carbonate according to claim 2, wherein The equivalent ratio of the carbonate-containing compound to the unsaturated double bond-containing compound is 0.8 to 1.

2.

5. A method for preparing an unsaturated compound containing a carbonate, characterized in that: Include: Performing a catalytic step, wherein diphenyl carbonate and a difunctional epoxy compound are mixed and then catalyzed by a catalyst to obtain a reactant; and An addition step is performed, wherein acrylic acid or methacrylic acid is added to the reactant to obtain an unsaturated compound containing a carbonate ester having a structure as shown in formula (II): Wherein, X is vinyl, propenyl, acrylic or methacrylic; wherein R1 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group or a halogen atom, and a is an integer from 0 to 5; Wherein, B is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or a structure represented by formula (i), formula (ii), or formula (iii): wherein R2 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group or a halogen atom, and b is an integer from 0 to 4; wherein R3 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a nitro group or a halogen atom, and c is an integer from 0 to 4; wherein Y is a single bond, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 1 to 12 carbon atoms, an oxygen atom, a sulfur atom, a sulfonyl group, a sulfinyl group, an acyl group, a fluorenyl group, or a hexafluoropropane group; wherein Z is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an o-phenylene group, a m-phenylene group, or a p-phenylene group; Here, n is an integer from 0 to 10.

6. The method for preparing an unsaturated compound containing carbonate according to claim 5, wherein: The catalyst is an organic base, and the equivalent ratio of the bifunctional epoxy compound to the diphenyl carbonate is 2.0 to 8.

0.

7. A solidified product, characterized in that: The present invention is obtained by subjecting the carbonate-containing unsaturated compound as claimed in claim 1 to a curing reaction.

8. The cured product according to claim 7, wherein The curing reaction is completed by adding the carbonate-containing unsaturated compound to a resin and heating the resin.

9. The cured product according to claim 8, wherein The resin is an unsaturated polyester resin or a vinyl ester resin.

10. The cured product according to claim 8, wherein The added amount of the carbonate-containing unsaturated compound is 3 to 20 weight percent of the resin content.

11. A method for degrading a solidified material, characterized in that: Include: Providing the cured product according to claim 7; and A degradation step is performed, wherein an amine compound is reacted with the solidified material to degrade the solidified material.

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