KR100557836B1 - Acrylic dicyclopentadiene monomer and the preparation the same, and the hardener using the same - Google Patents

Abstract

The present invention relates to an acrylated dicyclopentadiene (hereinafter referred to as DCPD) monomer, a preparation method thereof and a cured product using the same. More specifically, by introducing an acryl group into a cyclopentadiene dimer dicyclopentadiene (DCPD) to synthesize a DCPD monomer capable of radical polymerization at room temperature, using this to provide a cured product that can be polymerized at room temperature.

Acrylic group * Dicyclopentadiene (DCPD) * Cured product * Radical polymerization

Description

Acrylic dicyclopentadiene monomer and the preparation the same, and the hardener using the same

The present invention relates to an acrylated dicyclopentadiene (hereinafter referred to as DCPD) monomer, a preparation method thereof and a cured product using the same. More specifically, by introducing an acryl group into a cyclopentadiene dimer dicyclopentadiene (DCPD) to synthesize a DCPD monomer capable of radical polymerization at room temperature, using this to provide a cured product that can be polymerized at room temperature.

In general, C5 separated from the naphtha cracker contains about 18-22% of cyclopentadiene, and the cyclopentadiene is present as a dimer at normal temperature and pressure. Dicyclopentadiene (Dicyclopentadiene, hereinafter referred to as DCPD), a cyclopentadiene dimer, is used for various purposes depending on the purity. Specifically, low purity (70 ~ 85%) DCPD is used for petroleum resin, unsaturated polyester resin, etc., 90 ~ 95% DCPD is EPDM elastic material, and high purity (95 ~ 99%) DCPD is COC (Cyclo Olefin Copolymer) And Reaction Injection Molding (hereinafter referred to as RIM) through Ring Open Metathesis Polymerization (ROMP). However, most DCPD among C5 separated from naphtha crackers is used as fossil fuel, and the amount of DCPD used for various purposes is very small.

Specific prior arts related to the DCPD are as follows.

The ring-opening polymerization of cyclic olefins, first reported by Eleuterio in US Pat. No. 3,074,918 (1963), enabled polymer polymers using various cyclic monomers with double bonds. Among them, the ring-opening polymerization reaction using high purity DCPD as a monomer has the great advantage that RIM molding using DCPD is possible. However, the above-mentioned RIM molding must use high purity DCPD, and the reaction catalyst is also very sensitive to moisture or air, and thus has a high equipment cost. Since the early 1990s, ruthenium-based ROMP catalysts, which are less sensitive to moisture or air, have been developed, making RIM molding easier (Grubbs, RH et al . J. Am. Chem. Soc. , 1992, 114, 3974). The development of the ruthenium-based ROMP catalyst has also been developed and Robert H. Grubbs reported a ruthenium-based ring-opening polymerization catalyst having activity even at low purity (81-86%) DCPD in US Patent No. 6,020443 (2000). However, in the case of the present invention, an excess ruthenium-based ROMP catalyst should be used in the low purity DCPD, and there is a problem in that the reaction temperature is significantly lower than that of the high purity DCPD, thereby increasing the reaction temperature by 50 ° C or more. In addition, the price of the ruthenium-based ROMP catalyst is very high, there is a problem that a lot of restrictions on the usage.

Therefore, research has been conducted on the synthesis of derivatives having reactive groups introduced into DCPD in order to increase the activity of DCPD monomers as well as the development of a catalyst having high activity of ROMP reaction in order to effectively utilize DCPD. U. S. Patent No. 3,642, 750 (1972) first introduced an acrylic group in an esterification reaction to DCPD-diol for use as a coating, and thereafter, studies on cyclic olefins in which acrylic was introduced for use as a photocurable monomer Progressed. In addition, recently, there is a report on a photocurable monomer in which an epoxy group is introduced into DCPD to enhance activity (Crivello, JV et al . , Chem. Mater. , 2000, 12, 3674). However, in the case of DCPD in which various reactive groups are introduced as described above, alcoholic or alkoxylated DCPD derivatives were used in the manufacturing process, and the reaction process is not only in several stages but also the use of the synthesized monomers is applied to coating or photocurable monomers. There is a problem that is limited.

Thus, the present inventors have studied the DCPD derivative which can be radically polymerized more easily even at room temperature in order to solve the problem of the ring-opening polymerization reaction, when radical polymerization is possible at room temperature when synthesizing the DCPD derivative by introducing an acrylic group into DCPD In addition, the present invention was completed by finding that the cured product may be polymerized at room temperature using the DCPD derivative.

Accordingly, an object of the present invention is to provide an acrylated dicyclopentadiene monomer in which an acryl group is introduced into dicyclopentadiene.

Another object of the present invention is to provide a method for preparing the acrylated dicyclopentadiene monomer.

In addition, another object of the present invention is to provide a cured product prepared using the acrylated dicyclopentadiene monomer.

In order to achieve the above object, the present invention provides an acrylated dicyclopentadiene monomer capable of radical polymerization by introducing an acrylic group into dicyclopentadiene.

Hereinafter, the present invention will be described in more detail.

The acrylated dicyclopentadiene of this invention introduce | transduces the acryl group which is a high functional group to dicyclopentadiene (DCPD). Specific examples thereof are monomers represented by the following Chemical Formulas 1 to 3.

(a) DCPD + Acrylic Acid (b) DCPD + Hydroxyacrylate

 (Wherein R is H or an alkyl group and n is an integer of 0 to 5)

DCPD + Polybasic Acid + Hydroxyacrylate

(Wherein R is H or an alkyl group, n is an integer of 0 to 5, and A is dicarboxylic acid or dicarboxylic anhydride.)

DCPD + Polybasic Acid + Epoxyacrylate

 (Wherein, A is dicarboxylic acid or dicarboxy anhydride, E is epoxy acrylate.)

The acrylated dicyclopentadiene monomer represented by Chemical Formulas 1 to 3 can be easily polymerized by a general radical polymerization catalyst, and molecular weight and Tg (glass transition temperature) are also superior to conventional polymers. For example, Tg = 110-140 ° C. for Poly-DCPD, and Tg = 110 ° C. for PMMA.

In the preparation method of the acrylated DCPC of the present invention, a carboxyl group or an alcohol group is added to the DCPD using a non-oxidizing acid such as florolic acid and triflic acid, an acid, or an oxidizing agent. A method of synthesizing acrylated DCPD by the method (Formula 1); A method of synthesizing acrylated DCPD through an addition reaction in the same manner as in Formula 1, after esterification of hydroxyacrylate with an alcohol group through a ring-opening reaction of a polybasic acid such as dicarboxylic anhydride; Alternatively, after combining one functional group of a polybasic acid such as dicarboxylic acid or dicarboxylic anhydride with DCPD through an addition reaction, the remaining carboxylic acid is synthesized by introducing an acrylic group using an epoxy group ring-opening reaction of epoxy acrylate (Formula 3). There is this. In particular, when maleic acid is used as the polybasic acid in Chemical Formula 3, not only an acryl group but also an olefin group is introduced into the monomer, and thus, a highly reactive acrylated DCPD may be synthesized.

In the preparation method of the present invention, the acrylated DCPD is an addition reaction, unlike the method of introducing acrylic acid through esterification to a conventional hydroxylated DCPD [HO- (CH ₂ ) _n -DCPD] (US Pat. No. 3,642,750). By introducing into DCPD through it is possible to introduce a DCPD monomer more various acrylic groups. In particular, when the hydroxylated DCPD in which ethylene oxide is reacted with DCPD is used as a reactant for the conventional esterification reaction, this also is not an easy reaction and is expensive. Therefore, the preparation method of the present invention is very useful as a simpler and more economical way to introduce various acrylic groups into the DCPD through the addition reaction.

On the other hand, since the acrylated DCPD monomer synthesized above has a vinyl group, free radical vinyl polymerization is possible at room temperature more easily. Therefore, BPO (Dibenzoyl peroxide, C ₆ H ₅ CO-OO-COC ₆ H ₅ ) powder or paste and tertiary amines in the synthesized acrylated DCPD monomer are specifically DMA (Dimetyl Aniline), DEA (Diethyl Aniline), DMPT (Dimethyl) A cured product can be obtained by initiating polymerization using -para- toluidine (Ethoxylated-para-toluidine), EPT (methyl hydroxylethyl-para-toluidine), or the like.

Hereinafter, although an Example is given and this invention is demonstrated in detail, this invention is not limited only to the following example.

Example 1 DCPD Acrylate Synthesis

Into a flask equipped with a thermometer, a nitrogen gas introduction tube, a stirrer, and a condenser, 1 mole (155.54 g) of 85% DCPD (manufactured by LG Petrochemical Co., Ltd.) and 200 ppm of toluhydroquinone were added, and the temperature was raised to 100 ° C. Next, a solution containing 1 mol (72.1 g) of acrylic acid and triflic acid (CF ₃ SO ₃ H) in comparison with acrylic acid at 0.1 wt% (0.072 g) was added dropwise over 2 hours while maintaining 100 ° C. After the dropwise addition, the acid value was measured every 30 minutes. After 5 hours, 100 ppm of hydroquinone was added at an acid value of 20 KOH ml / g, and cooled to room temperature to terminate the reaction to synthesize DCPD acrylate.

Example 2 DCPD Methacrylate Synthesis

Into a flask equipped with a thermometer, a nitrogen gas introduction tube, a stirrer, and a condenser, 1 mole (155.54 g) of 85% DCPD (manufactured by LG Petrochemical Co., Ltd.) and 200 ppm of toluhydroquinone were added, and the temperature was raised to 100 ° C. Next, a solution of 1 mol of methacrylic acid and 0.5 wt% of 48% tetrafluorobolic acid (HBF ₄ ) relative to acrylic acid was added dropwise over 2 hours while maintaining 100 ° C. After completion of the dropwise addition, the acid value was measured every 30 minutes. After 5 hours, 100 ppm of hydroquinone was added at an acid value of 20 KOH ml / g, and cooled to room temperature to terminate the reaction to synthesize DCPD methacrylate.

Example 3 Synthesis of DCPD Hydroxyethylacrylate

Into a flask equipped with a thermometer, a nitrogen gas introduction tube, a stirrer, and a condenser, 1 mole (155.54 g) of 85% DCPD (manufactured by LG Petrochemical) and 200 ppm of toluhydroquinone were added thereto, and the temperature was raised to 60 ° C. Next, a solution of 1 mol of 2-hydroxyethyl acrylate and 0.5 wt% of 48% tetrafluorobolic acid (HBF ₄ ) relative to acrylic acid was added dropwise over 2 hours while maintaining 60 ° C. After the dropwise addition, the acid value was measured every 30 minutes. After 15 hours, 100 ppm of hydroquinone was added at an acid value of 30 KOH ㎖ / g, and cooled to room temperature to terminate the reaction to synthesize DCPD hydroxyethyl acrylate.

Example 4 Synthesis of DCPD hydroxyethyl methacrylate

Into a flask equipped with a thermometer, a nitrogen gas introduction tube, a stirrer, and a condenser, 1 mole (155.54 g) of 85% DCPD (manufactured by LG Petrochemical) and 200 ppm of toluhydroquinone were added thereto, and the temperature was raised to 60 ° C. A solution containing 1 mol of 2-hydroxyethyl methacrylate and 0.5 wt% of 48% tetrafluorobolic acid (HBF ₄ ) relative to acrylic acid was added dropwise over 2 hours while maintaining 60 ° C. After the dropwise addition, the acid value was measured every 30 minutes. After 15 hours, 100 ppm of hydroquinone was added at an acid value of 30 KOH ㎖ / g, and cooled to room temperature to terminate the reaction to synthesize DCPD hydroxyethyl methacrylate.

Example 5 Synthesis of DCPD-maleic-hydroxyethyl acrylate

Into a flask equipped with a thermometer, a nitrogen gas introduction tube, a stirrer, and a condenser, 2 mol of maleic anhydride and 1 mol of 2-hydroxyethyl acrylate were added together with 200 ppm of toluhydroquinone, and the temperature was raised to 100 ° C. Next, the acid value was measured every 10 minutes at 100 ° C., cooled to 80 ° C. at an acid value of 262 KOHml / g, and then 100 ppm of hydroquinone was added thereto, followed by further heating to 100 ° C. When it reached 100 ° C, 0.5 wt% of 48% tetrafluorobolic acid (HBF ₄ ) was added thereto, and 1 mol of 85% DCPD was added dropwise over 2 hours. After the addition, the acid value was measured every 30 minutes. After 5 hours after the addition, the acid value was confirmed by 20 KOHml / g, 100 ppm of hydroquinone was added and cooled to room temperature to terminate the reaction. The rate was prepared.

Example 6 Synthesis of DCPD-phthalic-hydroxyethyl acrylate

Into a flask equipped with a thermometer, a nitrogen gas introduction tube, a stirrer, and a condenser, 2 mol of phthalic anhydride and 1 mol of 2-hydroxyethyl acrylate were added together with 200 ppm of toluhydroquinone, and the temperature was raised to 100 ° C. Next, the acid value was measured every 10 minutes at 100 ° C., cooled to 80 ° C. at 212 KOH ml / g, and then charged to 100 ppm of hydroquinone, and then heated up to 100 ° C. When the temperature reached 100 ° C., 0.2 wt% of triflic acid (CF ₃ SO ₃ H) was added thereto, and 1 mol of 85% DCPD was added dropwise over 2 hours. Next, after the dropping, the acid value was measured every 30 minutes. After 5 hours, the acid value was measured 20 KOH ㎖ / g, 100ppm of hydroquinone was added and the reaction was completed by cooling to room temperature to terminate the DCPD-phthalic-hydride. Roxyethyl acrylate was synthesized.

Example 7 Synthesis of DCPD-tetrahydrophthalic-hydroxyethyl methacrylate

Into a flask equipped with a thermometer, a nitrogen gas introduction tube, a stirrer, and a condenser, 2 mol of tetrahydrophthalic anhydride and 1 mol of 2-hydroxyethyl acrylate were added together with 200 ppm of toluhydroquinone, and the temperature was raised to 100 ° C. Next, the acid value was measured every 10 minutes at 100 ° C., the acid value was cooled to 80 ° C. at 199 KOHml / g, and 100 ppm of hydroquinone was added thereto, and the temperature was again raised to 100 ° C. When it reached 100 ° C, 0.5 wt% of 48% tetrafluorobolic acid (HBF ₄ ) was added thereto, and 1 mol of 85% DCPD was added dropwise over 2 hours. After the addition, the acid value was measured every 30 minutes. After 5 hours, the acid value was measured 20 KOHml / g, 100ppm of hydroquinone was added and the reaction was completed by cooling to room temperature to terminate the reaction with DCPD-tetrahydrophthalic-hydr. Roxyethyl methacrylate was synthesized.

Example 8 Synthesis of DCPD-succinic-hydroxyethyl methacrylate

Into a flask equipped with a thermometer, a nitrogen gas introduction tube, a stirrer, and a condenser, 2 mol of succinic anhydride and 1 mol of 2-hydroxyethyl methacrylate were added together with 200 ppm of toluhydroquinone, and the temperature was raised to 100 ° C. Next, the acid value was measured every 10 minutes at 100 ° C., cooled to 80 ° C. at an acid value of 244 KOHml / g, and then 100 ppm of hydroquinone was added thereto, and then heated up to 100 ° C. When the temperature reached 100 ° C., 0.5 wt% of 48% tetrafluorobolic acid (HBF ₄ ) was added thereto, and 1 mol of 85% DCPD was added dropwise over 2 hours. After the addition, the acid value was measured every 30 minutes. After 5 hours, the acid value was measured 20 KOH ㎖ / g, 100ppm of hydroquinone was added and cooled to room temperature to terminate the reaction. Methaacrylate was synthesized.

Example 9 Synthesis of DCPD-maleic-glycidylmethacrylate

Into a flask equipped with a thermometer, a nitrogen gas introduction tube, a stirrer, and a condenser, 1 mol of 85% DCPD and 2 mol of maleic anhydride were added together with 200 ppm of toluhydroquinone, and the temperature was increased to 120 ° C. Next, 1 mol of distilled water was slowly added dropwise while maintaining the temperature at 120 ° C. After the addition, the acid value was measured every 10 minutes to determine the acid value 221 KOHml / g and cooled to 100 ℃. Upon reaching 100 ° C., 0.2 wt% of BDMA was added, and immediately 1 mol of glycidyl methacrylate was added dropwise for 1 hour while maintaining the temperature. After the dropping, the acid value was measured every 10 minutes, and after 2 hours, the acid value was confirmed to be 10 KOHml / g, 100 ppm of hydroquinone was added and the reaction was completed by cooling to room temperature to obtain DCPD-maleic-glycidyl methacrylate. Synthesized.

Preparation Example 1 Polymerization of DCPD Acrylate

100 g of the DCPD acrylate synthesized in Example 1 was placed in a beaker, and 50% BPO (Dibenzoyl peroxide, C ₆ H ₅ CO-OO-COC ₆ H ₅ ) powder or paste was dissolved well by mixing 1.0-2.0 g. Thereafter, polymerization was initiated using 0.2-1.0 g of Dimethyl Aniline (DMA). The resulting cured product was dissolved in THF (tetrahydrofuran) to measure the relative molecular weight of polystyrene standardized by GPC analysis.

Production Example 2 Polymerization of DCPD Methacrylate

100 g of the DCPD methacrylate synthesized in Example 2 was placed in a beaker, and 50% BPO (Dibenzoyl peroxide, C ₆ H ₅ CO-OO-COC ₆ H ₅ ) powder or paste was mixed well with 1.0-2.0 g. After melting, 0.2-1.0 g of DMA (Dimetyl Aniline) was used to initiate polymerization. The obtained cured product was dissolved in THF to measure the relative molecular weight of polystyrene standardized by GPC analysis.

Preparation Example 3 Polymerization of DDCPD Hydroxyethylacrylate

100 g of the DCPD hydroxyethyl acrylate synthesized in Example 3 was placed in a beaker, and 1.0 to 2.0 g of 50% BPO (Dibenzoyl peroxide, C ₆ H ₅ CO-OO-COC ₆ H ₅ ) powder or paste was used. After mixing well, the polymerization was started using 0.2-1.0 g of methyl-para- toluidine (DMPT). The obtained cured product was dissolved in THF to measure the relative molecular weight of polystyrene standardized by GPC analysis.

Production Example 4 Polymerization of DCPD hydroxyethyl methacrylate

100 g of the DCPD hydroxyethyl methacrylate synthesized in Example 4 was placed in a beaker, and 50% BPO (Dibenzoyl peroxide, C ₆ H ₅ CO-OO-COC ₆ H ₅ ) powder or paste was 1.0-2.0. g After mixing well, the polymerization was started using 0.2-1.0 g of methyl-para- toluidine (DMPT). The obtained cured product was dissolved in THF to measure the relative molecular weight of polystyrene standardized by GPC analysis.

Production Example 5 Polymerization of DCPD-maleic-hydroxyethyl acrylate

100 g of the DCPD-maleic-hydroxyethyl acrylate synthesized in Example 5 was placed in a beaker, and 50% BPO (Dibenzoyl peroxide, C ₆ H ₅ CO-OO-COC ₆ H ₅ ) powder or paste was added thereto. 1.0-2.0 g After mixing well, the mixture was dissolved, and polymerization was started using 0.2-1.0 g of Ethoxylated-para-toluidine (EPT). The obtained cured product was dissolved in THF to measure the relative molecular weight of polystyrene standardized by GPC analysis.

Production Example 6 Polymerization of DCPD-phthalic-hydroxyethyl acrylate

100 g of the DCPD-phthalic-hydroxyethyl acrylate synthesized in Example 6 was placed in a beaker, and 50% BPO (Dibenzoyl peroxide, C ₆ H ₅ CO-OO-COC ₆ H ₅ ) powder or paste was added thereto. 1.0-2.0 g After mixing well, the mixture was dissolved, and polymerization was started using 0.2-1.0 g of Ethoxylated-para-toluidine (EPT). The obtained cured product was dissolved in THF to measure the relative molecular weight of polystyrene standardized by GPC analysis.

Production Example 7 Polymerization of DCPD-tetrahydrophthalic-hydroxyethyl methacrylate

100 g of a DCPD-tetrahydrophthalic-hydroxyethyl methacrylate synthesized in Example 7 was placed in a beaker, and 50% BPO (Dibenzoyl peroxide, C ₆ H ₅ CO-OO-COC ₆ H ₅ ) powder was added thereto. Alternatively, 1.0 to 2.0 g of the paste was mixed and dissolved, and then 0.2 to 1.0 g of EPT (Ethoxylated-para-toluidine) was used to initiate polymerization. The obtained cured product was dissolved in THF to measure the relative molecular weight of polystyrene standardized by GPC analysis.

Production Example 8 Polymerization of DCPD-succinic-hydroxyethyl methacrylate

100 g of the DCPD-succinic-hydroxyethyl methacrylate synthesized in Example 8 was placed in a beaker, and 50% BPO (Dibenzoyl peroxide, C ₆ H ₅ CO-OO-COC ₆ H ₅ ) powder or paste 1.0 to 2.0 g of the mixture was dissolved well, MHPT (methyl hydroxylethyl-para- toluidine) 0.2 to 1.0 g was used to initiate the polymerization. The obtained cured product was dissolved in THF to measure the relative molecular weight of polystyrene standardized by GPC analysis.

Preparation Example 9 Polymerization of DCPD-maleic-glycidyl methacrylate

100 g of a DCPD-maleic-glycidyl methacrylate synthesized in Example 9 was placed in a beaker, and 50% BPO (Dibenzoyl peroxide, C ₆ H ₅ CO-OO-COC ₆ H ₅ ) powder or paste After 1.0-2.0 g of the mixture was dissolved well, 0.2-1.0 g of methyl hydroxylethyl-para-toluidine (MHPT) was used to initiate polymerization. The obtained cured product was dissolved in THF to measure the relative molecular weight of polystyrene standardized by GPC analysis.

The polymerization method of Preparation Example 1-9 is a technique generalized by a free radical vinyl polymerization method in an acrylic monomer, but the conventional technique has not been applied to olefins in a cyclic structure such as DCPD. However, in the present invention, the polymerization cured product can be easily obtained even at room temperature by radical polymerization method by introducing an acryl group into DCPD.

The properties of the acrylated dicyclopentadiene monomer (Examples 1 to 9) synthesized above and the cured product (Preparation Examples 1 to 9) using the same are shown in Table 1 below.

Classification Note 1 Cured product Glass transition temperature (℃) (Note 2) Molecular weight (Mw) (3) Gelation time (minutes) Example 1 DCPD-AA 325  82000 15 Example 2 DCPD-MAA 340 85000 13 Example 3 DCPD-HEA 270 43000 20 Example 4 DCPD-HEMA 270 55000 23 Example 5 DCPD-MA-HEA 278 87000 18 Example 6 DCPD-PA-HEA 310 86000 24 Example 7 DCPD-THPA-HEMA 325 92000 25 Example 8 DCPD-SA-HEMA 295 62000 26 Example 9 DCPD-MA-GMA 348 92000 14

* 1 DCPD = Dicyclopentadiene

      AA = acrylic acid

      MAA = Meta Acrylic Acid

      HEA = 2-hydroxyethyl acrylate (2-HydroxyEthylAcrylate)

      HEMA = 2-HydroxyEthylMeta Acrylate

      MA = Maleic Anhydride

      PA = Phthalic Anhydride

     THPA = TetraHydro Phthalic Anhydride

      SA = Succinic Anhydride

      GMA = Glycidiyl MetaAcrylate

(Note 2) Molecular weight: PS standard GPC analysis by dissolving the cured product in THF

(3) Gelation time: 25 ℃ water bath, monomer / BPO / tertiary amines = 100/5/1

As described above, a DCPD derivative capable of room temperature radical polymerization was synthesized by introducing an acryl group into dicyclopentadiene (DCPD). Using this, a RIM cured product using low purity DCPD can be easily provided at room temperature.

Claims (7)

delete An acrylated dicyclopentadiene monomer prepared by introducing an acryl group into dicyclopentadiene (DCPD), The acrylated dicyclopentadiene monomer is a acrylated dicyclopentadiene monomer, characterized in that the compound represented by the formula (1) -3. [Formula 1] (b) DCPD + Hidihydroxyacrylate

 (Wherein R is H or a methyl group and n is an integer of 0 to 5) [Formula 2] DCPD + Polybasic Acid + Hydroxyacrylate

(Wherein R is H or a methyl group, n is an integer of 0 to 5, and A is dicarboxylic acid or dicarboxylic anhydride.) [Formula 3] DCPD + Polybasic Acid + Epoxyacrylate

 (Wherein, A is dicarboxylic acid or dicarboxy anhydride, E is epoxy acrylate.) The carboxyl group or alcohol group in DCPD is synthesized by the addition reaction method of the acrylated DCPD according to claim 2 using a non-oxidizing acid, acid or oxidizing agent (Acid acting agent). Manufacturing method. A method for producing an acrylated DCPD, characterized in that to synthesize the acrylated DCPD according to claim 2 through an esterification reaction of the hydroxyacrylate with an alcohol group through the ring opening of the polybasic acid. Acrylate DCPD, characterized in that the acrylated DCPD according to claim 2 is synthesized by combining one functional group of the polybasic acid with DCPD through an addition reaction, and then introducing the acrylic group using the epoxy group ring-opening reaction of epoxy acrylate. Manufacturing method. delete delete