KR20210075577A - Adhesion promoter of rubber elastomer based on triazole network and synthesis method of the same - Google Patents

Abstract

The present invention relates to an adhesion promoter for a triazole network-based rubber elastic body and to a synthesis method thereof, and more particularly, to a technique for synthesizing a copolymer containing an azide group by synthesizing an acrylate monomer having a chloride functional group at a terminal, and after binary or ternary copolymer polymerization using the monomer, substituting an azide group for chloride present in a side chain of the copolymer.

Description

Adhesion promoter of a triazole network-based rubber elastomer and a method for synthesizing the same {ADHESION PROMOTER OF RUBBER ELASTOMER BASED ON TRIAZOLE NETWORK AND SYNTHESIS METHOD OF THE SAME}

The present invention is a polymer-type adhesion promoter capable of enhancing the bonding force between a triazole binder and a filler material such as carbon black and silica, and relates to an adhesion promoter for a triazole network-based rubber elastomer and a method for synthesizing the same.

Elastomer rubber is a material with viscoelasticity, and is composed of a filler material that can have strength, a polymer binder that has elasticity, and an adhesion promoter (binder) that connects the two.

The filling material of the rubber elastomer is made of carbon black or silica. Since the mechanical properties of the rubber elastomer are greatly affected by the bonding force between the filler material and the binder, the adhesion promoter (binder) used for the purpose of enhancing the bonding strength of the two components occupies a very important part in the development of the rubber elastomer. .

Carbon black is widely used as a filling material for rubber elastomers today. When carbon black is added to a polymer matrix such as rubber, mechanical properties such as tensile strength, tear strength, abrasion resistance, and hardness can be improved. According to a recent report, it is known that the dispersion between the additive and the polymer matrix is not good, so that it plays the role of pores as much as the particle size, which leads to a sharp decrease in mechanical properties. In addition, the degree of dispersion of additives is known to be an important factor in improving mechanical properties, and since it depends on physical bonding or secondary bonding, van der Waals force, the bonding strength of these composites is very weak.

Silica, which exhibits reinforcing power similar to carbon black as a filler material, can be implemented in various colors and does not lose its softness even at very low temperatures, but due to the hydroxy (-OH) group on the surface, it exhibits high polarity and hydrophilic properties of the surface. It is known that it is not easy to obtain sufficient physical properties because of the strong mutual aggregation between the livers, making it difficult to uniformly disperse in the matrix.

An example of the development of the rubber elastomer is a polyurethane rubber elastomer developed in the mid-1950s. Polyurethane rubber elastomer is a polymer matrix that is widely used even today as a urethane matrix structure by reacting an organic material having a hydroxyl group (-OH) with isocyanate (NCO). However, there are disadvantages in that it has strong hygroscopicity and is not stable in water. Therefore, there is a trend of research on triazole rubber elastomers to replace them.

1,2,3-Triazole is being used in various fields such as polymers and materials science. 1,2,3-triazole is typically used in 1,3-dipolar cycloaddition between a derivative having an alkyne and an azide functional group, which is a reaction of the click chemistry type. can be synthesized by The advantage of this click chemistry type reaction is that it provides a high yield and there are no side reactions.

The triazole rubber elastomer system used for this uses a cycloaddition reaction of an azide and an alkyne group, whereby an easy and convenient process can be obtained. Compared to the polyurethane rubber elastomer system, it has the advantage of not being affected by moisture due to its high water stability. However, when the previously used adhesion promoter was applied to the triazole rubber elastomer system, the effect was confirmed to be insignificant, so it is necessary to study the synthesis technology of a new adhesion promoter to improve the bonding force between the triazole binder and the filler material.

As mentioned above, the rubber elastomer is a composite elastomer in which solid particles are embedded in a chemically crosslinked network, which is a matrix formed by the reaction of a polymer and a curing agent. When the bonding force between the matrix structure and the solid particles in the rubber elastomer is lost, mechanical properties such as tensile force and elongation of the elastomer are not excellent, so an adhesion promoter for reinforcing it is used. The adhesion promoter of a polyurethane-based rubber elastomer formed by the crosslinking reaction of a polymer terminally substituted with a hydroxyl group and an isocyanate curing agent uses an adhesion promoter containing a hydroxyl group capable of reacting with isocyanate, and improves bonding strength with solid particles. In addition to increasing the molecular weight of the adhesion promoter to a certain extent, a cyano (-CN) group with high polarity is applied to surround the solid particles to form a matrix and solid particles through physical bonding, hydrogen bonding, and van der Waals bonding. It enhances the bond between the two.

However, the binder of the matrix-based rubber elastomer made of triazole formed by the reaction of azide and alkyne in which the matrix of the elastomer is not urethane-based contains an azide group capable of reacting with an alkyne compound, a curing agent of the triazole matrix. shall.

Existing widely used polyurethane rubber elastomers react with isocyanate (NCO) having a hydroxyl group (-OH) to form a urethane matrix structure. In this matrix, carbon black, a filler material, silica, and various additives are mixed. produced by dispersing. However, since polyurethane rubber elastomers have a strong hygroscopicity disadvantage, triazole rubber elastomers to replace them are being studied, but triazole binders and known adhesion promoters do not properly bind filler materials, so it was judged not to be appropriate. Therefore, in order to enhance the bonding force between the triazole binder and the filler material, carbon black or silica, it is necessary to study the synthesis technology of an adhesion promoter suitable for this.

Korean Patent Registration No. 10-1468016

The present invention relates to the synthesis of monomers required for the synthesis technology of the adhesion promoter of the rubber elastomer and the content related to the polymer synthesis using the synthesized monomer. In detail, the triazole binder that is being studied as a rubber elastomer to replace the polyurethane rubber elastomer. An object of the present invention is to provide a method for synthesizing a novel adhesion promoter capable of properly combining carbon black and silica, which are filler materials.

Accordingly, the present invention provides a method for synthesizing a copolymer polymer having a high molecular weight while containing an azide group capable of binding to a triazole matrix and containing a cyano group in order to enhance bonding strength with solid particles in a rubber elastomer. aim to

In order to achieve the above object, the adhesion promoter of the rubber elastomer of the present invention is an acrylate monomer having a chloride functional group at the terminal and 2-azidoethyl acrylate (2-azidoethyl acrylate) as a heterogeneous acrylate monomer. azidoethyl acrylate) is used to synthesize a binary copolymer or a terpolymer, and the chloride functional group present in the side chain of the polymerized binary copolymer or terpolymer is substituted with an azide functional group.

The acrylate monomer having a chloride functional group is preferably at least one selected from among acrylonitrile, 2-hydroxyethyl acrylate and methyl acrylate.

The chloride functional group in the synthesized binary or terpolymer is substituted with an azide functional group by an azide reaction.

The number average molecular weight of the binary copolymer or terpolymer is preferably 7,000 to 30,000.

The azide functional group-containing repeating unit structure is preferably 10% to 50% by molar ratio in the composition of the entire copolymer.

In order to achieve another object, the method for synthesizing an adhesion promoter for a rubber elastomer of the present invention comprises the steps of synthesizing an acrylate monomer having a chloride functional group at the terminal, and 2-azidoethyl acryl as an acrylate monomer different from the acrylate monomer. polymerizing the binary copolymer or terpolymer using a rate, and substituting a chloride functional group present in the side chain of the binary copolymer or terpolymer with an azide functional group.

In the present invention, in order to synthesize a binary or terpolymer containing azide, a monomer having a chloride group and an acrylate monomer instead of polymerizing the copolymer using an azide-containing monomer that causes a side reaction with an acrylate compound input as a heterogeneous monomer Finally, the chloride functional group of the copolymer formed by polymerization with the azide is azidated, and an azidated copolymer can be obtained in high yield.

1 is a schematic diagram of a method for synthesizing 2-azidoethyl acrylate.
2 is a schematic diagram of a method for synthesizing 2-chloroethyl acrylate monomer.
Figure 3 is a schematic diagram of a synthesis method of _{NPBA-N 3} using a 2-chloroethyl acrylate monomer (2-Chloroethyl acrylate monomer).
4 is an azidated binary copolymer of acrylonitrile:2-azidoethyl acrylate ≒ 1.00: 0.25 monomer ratio and M _{n = 7,090 according to Example 3 of the present invention.}
5 is an azidated binary copolymer of acrylonitrile: 2-azidoethyl acrylate ≒ 1.00: 0.25 monomer ratio and M _{n = 19,280 according to Example 4 of the present invention.}
6 is an azide ternary with a monomer ratio of acrylonitrile: 2-hydroxyethyl acrylate: 2-azidoethyl acrylate ≒ 1.00: 0.20: 0.30 and M _{n = 11,700 according to Example 5 of the present invention;} It is a copolymer.
7 is an azidated terpolymer of acrylonitrile : methyl acrylate : 2-azidoethyl acrylate ≒ 1.00 : 0.20 : 0.30 monomer ratio and M _{n =27,040 according to Example 6 of the present invention.}

As used herein, terms such as "comprise" and "comprise" mean that the corresponding component may be inherent, unless otherwise specified, and does not exclude other components, but other components should be interpreted as being able to further include

Hereinafter, examples of the triazole network-based rubber elastomer adhesion promoter of the present invention and a method for synthesizing the same will be described in more detail with reference to the drawings. This embodiment is not limited to the embodiment described herein, since it may be implemented in various different forms by those of ordinary skill in the art to which the present invention pertains as an example.

Example 1 relates to a conventional method for synthesizing 2-azidoethyl acrylate. As shown in FIG. 1, after synthesizing 2-azidoethanol, the synthesized 2 -Azidoethanol (2-Azidoethanol) can be used to synthesize 2-Azidoethyl acrylate.

First, 2-azidoethanol required for the synthesis of 2-azidoethyl acrylate is 23.4 g (2-Bromoethanol) 30.0 g (0.24 mol) and sodium azide (sodium azide) 23.4 g ( 0.36 mol) was dissolved in 80 mL of a mixed solution in which water (H ₂ O) and acetone were mixed in a volume ratio of 1:1, and then reacted at 90° C. for 13 hours, and 3 as an organic layer using dichloromethane. times were extracted. The organic layer was dried using magnesium sulfate (MgSO ₄ ) and then distilled under reduced pressure to obtain 32.6 g (yield = 98%) of 2-azidoethanol as a colorless liquid. It was confirmed that it was 2-azidoethanol by nuclear magnetic resonance spectroscopy (NMR) analysis. ¹ H NMR (400 MHz, CDCl ₃ ) d 3.79 (t, J = 4.4 Hz, 2H), 3.46 (q, J = 4.4 Hz, 1H).

Then, 2-azidoethyl acrylate was prepared by dissolving 4.00 g (0.046 mol) of 2-azidoethanol and 5.46 g (0.054 mol) of triethylamine synthesized by the above-described method in dichloromethane. ) was dissolved in 80 mL, and then 4.52 g (0.050 mol) of acrylyl chloride was added dropwise at 0° C., and then the temperature was raised to room temperature and reacted for 2 hours. After adding a saturated sodium hydrogen carbonate (Saturated NaHCO ₃ ) aqueous solution under an ice bath (ice bath), the mixture is stirred for 30 minutes. The organic layer was extracted three times using a saturated aqueous sodium chloride (Saturated NaCl) solution. After drying the organic layer using magnesium sulfate (MgSO ₄ ), it was distilled under reduced pressure to obtain 6.2 g (yield = 94%) of 2-azidoethyl acrylate, which is an orange liquid, and synthesized 2-a Mapethyl acrylate is stored by adding hydroquinone to a concentration of 100 ppm as an inhibitor.

At this time, as a result of nuclear magnetic resonance (NMR) analysis of the synthesized material, it was confirmed that it was 2-azidoethyl acrylate. ¹ H NMR (400 MHz, CDCl ₃ ) d 6.80 (dd, J = 17.3 Hz, 1.3 Hz, 1H), 6.18 (q, J = 6.9 Hz, 1 H), 5.90 (dd, J = 11.5 Hz, 1.5 Hz) , 1H), 4.35 (t, J = 2.6 Hz, 2H), 3.53 (t, J = 5.1 Hz, 2H).

However, in the 2-azidoethyl acrylate synthesized through the same method as in Example 1, a by-product was generated due to a side reaction of self polymerization due to the high reactivity between the azide group and the double bond functional group in the monomer. Therefore, column chromatography was performed as a purification process before polymerization. When the eluent was separated using methylene chloride and ethyl acetate 25:1 (v/v) by column chromatography, the yield of 2-azidoethyl acrylate was changed from 94% to 40%. It was difficult to polymerize the polymer.

Therefore, after synthesizing an acrylate monomer containing a chloride functional group at the terminal, and synthesizing a polymer using the synthesized acrylate monomer having a chloride functional group, an azide through a chloride functional group at the terminal ) by synthesizing a copolymer polymer containing a cyano group and having a high molecular weight as a method of introducing a functional group, a method for synthesizing an adhesion promoter for a triazole network-based rubber elastomer is provided.

In the synthesis of the adhesion promoter for rubber elastomers presented in the present invention, the molecular weight and the functional group at the terminal appear in different forms depending on the mixing ratio of heterogeneous acrylate monomers, initiators, and chain transfer agents (CTA), and the initiator and chain to be input Since differences in reaction rate and molecular weight occur depending on the transfer agent (CTA), the adhesion promoter of the elastomer rubber can be prepared under optimal synthesis conditions according to the ratio and molecular weight of the functional groups at the ends of the acrylate monomer.

Example 2 relates to a method for synthesizing 2-chloroethyl acrylate monomer as an acrylate monomer containing a chloride functional group, and the process is as shown in FIG. 2 .

After dissolving 20.00 g (0.25 mol) of 2-chloroethanol and 30.24 g (0.30 mol) of triethylamine in 140 mL of concentrated tetrahydrofuran (THF), acrylyl chloride at 0 ℃ (acryloyl chloride) 24.80 g (0.27 mol) was added dropwise, and then raised to room temperature and reacted for 5 hours. After terminating the reaction with distilled water, the organic layer was extracted three times using _{diethyl ether (Et 2 O).} The organic layer was dried using magnesium sulfate (MgSO ₄ ) and then distilled under reduced pressure to obtain 32.6 g (98%) of 2-chloroethyl acrylate as an orange liquid, and 4- as an inhibitor. Methoxyphenol (4-methoxyphenol) was added to a concentration of 100 ppm and stored.

As a result of nuclear magnetic resonance (NMR) analysis of the material synthesized in Example 2, it was confirmed that the synthesized material was 2-chloroethyl acrylate. ¹ H NMR (400 MHz, CDCl3) d 6.80 (dd, J = 16.0 Hz, 4.0 Hz, 1H), 6.15 (q, J = 9.3 Hz, 1 H), 5.88 (dd, J = 12.0 Hz, 4.0 Hz, 1H), 4.41 (t, J = 6.0 Hz, 2H), 3.72 (t, J = 4.0 Hz, 2H). ¹³ C NMR (100 MHz, CDCl3) d 165.6, 131.7, 127.7, 64.0, 41.4.4

Examples 3 to 6 below describe specific acrylate monomer types, mixing ratios, and molecular weights of adhesion promoters for rubber elastomers and methods for synthesizing them.

Example 3 acrylonitrile: 2-Azidoethyl acrylate ≒ 1.00: 0.25 monomer ratio and M _n = 7000 units of azide binary copolymer polymerization was carried out.

Acrylonitrile 3.15 g (59.45 mmol) and 2-chloroethyl acrylate 2.00 g, 14.86 mmol) and 1-dodecanethiol 0.42 g (2.08 mmol) and 0.24 g (1.49 mmol) of 2,2'-azobis (2-methylpropionitrile) (2,2'-azobis (2-methylpropionitrile) _{) in 19.88 mL of acetonitrile (CH 3} CN) (300 vol relative to the monomer) %) and then polymerization was carried out at 70 °C under a nitrogen environment. The polymerization rate was measured for molecular weight using dimethylformamide (DMF) gel permeation chromatography (GPC) every 1 hour, and after polymerization for 2 hours, the reaction was terminated by lowering the temperature to room temperature. _{The product was diluted in acetonitrile (CH 3} CN) and precipitated twice in methanol to remove residual monomer, initiator and solvent. Sodium azide (Sodium azide) 4.20 g (64.61 mmol) and NPBA derivative polymer, NPBA-Cl polymer was put in DMF (10 mL) and reacted at 90 ℃ for 14 hours. After completion of the reaction, the dimethylformamide (DMF) solvent was removed through vacuum distillation. _{After dilution with acetonitrile (CH 3} CN) to remove residual sodium azide, it was precipitated once in distilled water. After dilution with acetonitrile (CH ₃ CN) and precipitated twice in methanol, _{3.29 g of the NPBA-N 3} polymer of FIG. 4 as a yellow solid (yield = 64%) was obtained.

^{As a} result of confirming the actual composition ratio of the acrylate monomer in Example 3 through 1 H NMR, it was confirmed that Acrylonitrile: 2-Azidoethyl acrylate = 1.00: 0.27. ¹ H NMR (400 MHz, DMSO-d ₆ ) d 4.32-4.19 (m, CO ₂ C H ₂ CH ₂ N ₃ ), 3.65-3.56 (m, CO ₂ CH ₂ C H ₂ N ₃ ), 2.19-1.78 (m, -C H ₂ - in back bone chain). GPC analysis (DMF/0.05 M LiBr, PMMA calibration): M _n =7090, M _w =11180, PDI=1.57.

Example 4 is acrylonitrile: 2-azidoethyl acrylate ≒ 1.00: 0.25 monomer ratio and M _n = 19000 units of azide binary copolymer polymerization was carried out.

Acrylonitrile 12.62 g (237.8 mmol) and 2-chloroethyl acrylate 8.00 g (59.45 mol) and 1-dodecanethiol 0.46 g (2.31 mmol) and 2,2'-azobis (2-methylpropionitrile) (2,2'-azobis (2-methylpropionitrile)) 0.19 g (1.19 mmol) acetonitrile (CH ₃ CN) 48.64 mL (200 vol relative to the monomer) %) and then polymerization was carried out at 70 °C under a nitrogen environment. The polymerization rate was measured for molecular weight using dimethylformamide (DMF) gel permeation chromatography (GPC) every hour, and after polymerization for 8 hours, the temperature was lowered to room temperature to terminate the reaction. _{The product was diluted in acetonitrile (CH 3} CN) and precipitated twice in methanol to remove residual monomer, initiator and solvent. Sodium azide 19.40 g (298.4 mmol) and NPBA-Cl polymer were put in 60 mL of dimethylformamide (DMF) and reacted at 90° C. for 14 hours. After completion of the reaction, the dimethylformamide (DMF) solvent was removed through vacuum distillation. _{After dilution with acetonitrile (CH 3} CN) to remove residual sodium azide, it was precipitated once in distilled water. After dilution with acetonitrile (CH ₃ CN) and precipitated twice in methanol, 11.92 g (yield = 58%) _{of the NPBA-N 3 polymer of FIG. 5 as a yellow solid was obtained.}

^{As a} result of confirming the actual composition ratio of the acrylate monomer in Example 4 through 1 H NMR, it was confirmed that Acrylonitrile: 2-Azidoethyl acrylate = 1.00: 0.27. ¹ H NMR (400 MHz, DMSO-d ₆ ) d 4.32-4.19 (m, CO ₂ C H ₂ CH ₂ N ₃ ), 3.65-3.56 (m, CO ₂ CH ₂ C H ₂ N ₃ ), 2.19-1.78 (m, -C H ₂ - in back bone chain). GPC analysis (DMF/0.05 M LiBr, PMMA calibration): M _n =19280, M _w =37314, PDI=1.93.

Example 5 is acrylonitrile: 2-hydroxyethyl acrylate: 2-azidoethyl acrylate ≒ 1.00: 0.20: 0.30 monomer ratio and M _n = 11000 units of azidation terpolymer polymerization was carried out.

Acrylonitrile 1.96 g (37.06 mmol) and 2-hydroxyethyl acrylate 0.63 g (7.35 mmol) and 2-chloroethylacrylate 1.50 g (11.14 mmol) ) and 1-dodecanethiol (1-dodecanethiol) 0.25 g (1.23 mmol) and 2,2'-azobis (2-methylpropionitrile) (2,2'-azobis (2-methylpropionitrile)) 0.08 g ( 0.50 mmol) was added to _{10.40 mL of acetonitrile (CH 3} CN) (200 vol% relative to the monomer), and then polymerization was carried out at 70° C. under a nitrogen environment. The polymerization rate was measured for molecular weight using dimethylformamide (DMF) gel permeation chromatography (GPC) every hour, and after polymerization for 2 hours, the temperature was lowered to room temperature to terminate the reaction. _{The product was diluted in acetonitrile (CH 3} CN) and precipitated twice in methanol to remove residual monomer, initiator and solvent. Sodium azide 2.04 g (31.37 mmol) and NPBA-Cl polymer were put in 10 mL of dimethylformamide (DMF) and reacted at 90° C. for 14 hours. After completion of the reaction, the dimethylformamide (DMF) solvent was removed through vacuum distillation. _{After dilution with acetonitrile (CH 3} CN) to remove residual sodium azide, it was precipitated once in distilled water. After dilution with acetonitrile (CH ₃ CN) and precipitating twice in methanol, 2.86 g (yield = 45%) _{of the NPBA-N 3 polymer of FIG. 6 as a yellow solid was obtained.}

^{As a} result of confirming the actual composition ratio of the acrylate monomer in Example 5 through 1 H NMR, acrylonitrile: 2-hydroxyethyl acrylate: 2-azidoethyl acrylate (2 -Azidoethyl acrylate) = 1.00 : 0.22 : 0.33 was confirmed. ¹ H NMR (400 MHz, DMSO-d ₆ ) d 4.86-4.71 (m, CO ₂ C H ₂ CH ₂ OH), 4.32-4.11 (m, CO ₂ C H ₂ CH ₂ N ₃ ), 4.11-3.93 ( m, CO ₂ CH ₂ C H ₂ OH), 3.65-3.45 (m, CO ₂ CH ₂ C H ₂ N ₃ ), 2.17-1.58 (m, -C H ₂ - in back bone chain). GPC analysis (DMF/0.05 M LiBr, PMMA calibration): M _n =11700, M _w =17830, PDI=1.51.

Example 6 is acrylonitrile: methyl acrylate: 2-azidoethyl acrylate ≒ 1.00: 0.20: 0.30 monomer ratio and M _n = 27000 units of azide A terpolymer polymerization was performed.

Acrylonitrile 1.97 g (37.15 mmol) and methyl acrylate 0.63 g (7.35 mmol) and 2-chloroethyl acrylate 1.50 g (11.14 mmol) and 1-dode 0.10 g (4.95 mmol) of canthiol (1-dodecanethiol) and 0.05 g (0.31 mmol) of 2,2'-azobis (2-methylpropionitrile) (2,2'-azobis (2-methylpropionitrile)) in aceto After putting in nitrile (CH ₃ CN) 9.53 mL (200 vol% relative to the monomer), polymerization was carried out at 70° C. under a nitrogen environment. The polymerization rate was measured for molecular weight using dimethylformamide (DMF) gel permeation chromatography (GPC) every hour, and after polymerization for 3 hours, the reaction was terminated by lowering the temperature to room temperature. _{The product was diluted in acetonitrile (CH 3} CN) and precipitated twice in methanol to remove residual monomer, initiator and solvent. Sodium azide (Sodium azide) 1.23 g (18.92 mmol) and NPBA-Cl polymer were put in 10 mL of dimethylformamide (DMF) and reacted at 90° C. for 14 hours. After completion of the reaction, the dimethylformamide (DMF) solvent was removed through vacuum distillation. _{After dilution with acetonitrile (CH 3} CN) to remove residual sodium azide, it was precipitated once in distilled water. After dilution with acetonitrile (CH ₃ CN) and precipitated twice in methanol, 1.72 g (yield=42%) of _{NPBA-N 3} polymer as shown in FIG. 7 as a yellow solid was obtained.

^{As a} result of confirming the actual composition ratio of the acrylate monomer in Example 6 through 1 H NMR, acrylonitrile: methyl acrylate: 2-azidoethyl acrylate (2-Azidoethyl acrylate) = 1.00 : 0.22 : 0.33 was confirmed. ^{1 H NMR (400 MHz, DMSO} -d 6) d 4.33-4.15 (m, CO 2 C H 2 CH 2 N 3), 3.72-3.63 (m, OC H 3), 3.63-3.50 (m, CO 2 CH ₂ C H ₂ N ₃ ), 2.20-1.69 (m, -C H ₂ - in back bone chain). GPC analysis (DMF/0.05 M LiBr, PMMA calibration): M _n =27040, M _w =47580, PDI=1.76.

Claims (3)

A binary copolymer or terpolymer is synthesized using an acrylate monomer having a chloride functional group at the terminal and 2-azidoethyl acrylate as a heterogeneous acrylate monomer, present in the side chain of the polymerized binary copolymer or terpolymer Adhesion promoter of elastomer rubber, characterized in that the chloride functional group is substituted with an azide functional group. According to claim 1,
The acrylate monomer having a chloride functional group is an adhesion promoter for a rubber elastomer, characterized in that at least one selected from acrylonitrile, 2-hydroxyethyl acrylate and methyl acrylate. synthesizing an acrylate monomer having a chloride functional group at the terminal;
polymerizing a binary copolymer or a terpolymer using 2-azidoethyl acrylate as the acrylate monomer and a heterogeneous acrylate monomer; and
A method of synthesizing an adhesion promoter for a rubber elastomer, comprising: replacing a chloride functional group present in a side chain of the binary copolymer or the terpolymer with an azide functional group.

Images