JP2005350356A - Di(meth)acrylate compound and its curable composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a di(meth)acrylate compound improving performance such as curing shrinkage, heat resistance, moisture absorption, etc., as a photosensitive material for a resist, etc., a coating material such as an ink, coating, etc., and a raw material of an adhesive, a construction material, etc., and a curable composition by using the same. <P>SOLUTION: This di(meth)acrylate compound is obtained by performing the reaction of dimethylol compound having a terpene skeleton with a (meth)acrylic acid compound, and the curable composition is provided by blending the compound with a radical polymerization initiator. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a novel di (meth) acrylate compound and a curable composition containing the compound. Here, the di (meth) acrylate compound of the present invention means a diacrylate compound and a dimethacrylate compound. The di (meth) acrylate compound of the present invention and the curable composition containing this compound are used for photosensitive materials such as resists, coating materials such as inks and paints, adhesive materials, building materials, polymer materials, and developers. , Surfactants, plasticizers, insecticides, fungicides, pharmaceuticals, raw materials for rubber chemicals, etc.

Conventionally, with regard to radiation curable compositions using acrylic acid, methacrylic acid, methyl methacrylate, methacrylamide, glycidyl methacrylate, bisphenol A diglycidyl methacrylate, etc. as a raw material, it has already been used as a coating agent, paint, etc. A patent application has been filed as a material with good productivity (Patent Document 1).
However, these photosensitive compositions do not have sufficient performance in terms of curing shrinkage, heat resistance, water absorption and the like.
JP-A-4-11609

  The present invention is a novel material that improves the performance of curing shrinkage, heat resistance, water absorption, etc., as a photosensitive material such as a resist, a coating material such as ink and paint, an adhesive material, and a building material. It aims at providing the curable composition containing a meth) acrylate compound and this compound.

The present invention relates to a di (meth) acrylate compound obtained by reacting a dimethylol compound having a terpene skeleton with a (meth) acrylic acid compound, and a curable composition thereof.
Here, the di (meth) acrylate compound of the present invention is preferably a di (meth) acrylate compound having a bicyclo [2.2.2] -octane ring and a curable composition obtained by polymerizing the same. The di (meth) acrylate compound having a bicyclo [2.2.2] -octane ring is a di (meth) acrylate compound represented by the following formula (I).
Further, as the di (meth) acrylate compound of the formula (I), a di (meth) acrylate compound represented by the following formula (II) is preferable.
Furthermore, the curable composition of the present invention is a composition obtained by adding a radical polymerization initiator to this di (meth) acrylate compound, and is a composition that can be cured by radiation such as electron beams or ultraviolet rays.

〔ただし、式（I）中、Ｒ１，Ｒ２，Ｒ３，Ｒ４，Ｒ５，Ｒ６は互いに同一または異なり、
水素原子、またはｎが１〜５の整数である式Ｃ_nＨ_2n+1で表される炭化水素基を表す。Ｒ７は水素原子または、メチル基である。）

[In the formula (I), R1, R2, R3, R4, R5, R6 are the same or different from each other;
A hydrogen atom or a hydrocarbon group represented by the formula C _n H _{2n + 1} where _n is an integer of 1 to 5 is represented. R7 is a hydrogen atom or a methyl group. )

  The di (meth) acrylate compound of the present invention and the curable composition using the same can improve performance such as curing shrinkage, heat resistance, and water absorption.

Among the di (meth) acrylate compounds of the present invention, the compound represented by the above formula (I) is preferable, and further, as a specific compound, the di (meth) acrylate compound represented by the above formula (II) And di (meth) acrylate compounds represented by the following formula (III). However, the compound represented by the formula (I) is not limited to these compounds.

  Further, di (meth) acrylate compounds represented by the formula (I), the formula (II), the formula (III), and the like include cis-type and trans-type geometric isomers. ) Acrylate compounds are not limited to cis and trans types. However, when the di (meth) acrylate compound of the present invention is used as a polymer raw material, a trans type is preferably used.

The di (meth) acrylate compound of the present invention is obtained by reacting a dimethylol compound having a terpene skeleton with a (meth) acrylic acid compound.
One example of the production example of the di (meth) acrylate compound of the present invention is shown below.
That is, the di (meth) acrylate compound of the present invention can be produced by the following method. However, it is not limited to these manufacturing methods.
For example, the di (meth) acrylate compound of the present invention includes (a) a terpene compound, (b) at least one compound selected from unsaturated dicarboxylic acid, its acid anhydride, and unsaturated dicarboxylic acid dialkyl ester, Then, a reduction reaction is carried out to obtain a dimethylol compound, which is further obtained by esterification with (meth) acrylic acid or its anhydride.

  The (a) terpene compound is not particularly limited, but usually α-pinene, β-pinene, carene, α-terpinene, γ-terpinene, d-limonene, dipentene, terpinolene, α-ferrandolene, β-ferrane. Drain, paramentadienes, pyroneene, camphene, alloocimene, myrcene and the like can be used. Preferably, d-limonene, dipentene, α-ferrandolene, β-ferrandolene, α-terpinene, and the like are used. You may use a terpene compound individually or in combination of 2 or more types.

(B) Unsaturated dicarboxylic acid, acid anhydride thereof, and unsaturated dicarboxylic acid dialkyl ester are not particularly limited, but are usually maleic acid, maleic anhydride, maleic acid dialkyl ester, fumaric acid, fumaric acid dialkyl ester. Etc. can be used. Preferably, unsaturated dicarboxylic acid dialkyl ester is used.
These unsaturated dicarboxylic acids, unsaturated dicarboxylic acid anhydrides and unsaturated dicarboxylic acid dialkyl esters may be used alone or in combination of two or more.
Moreover, there is no restriction | limiting in particular as an alkyl component of unsaturated dicarboxylic acid dialkyl ester, For example, dimethyl, diethyl, dipropyl, dibutyl etc. are mentioned.

  The reaction between the terpene compound and at least one compound selected from unsaturated dicarboxylic acid, unsaturated dicarboxylic acid anhydride, and unsaturated dicarboxylic acid dialkyl ester is not particularly limited. Used. Preferably, a cycloaddition reaction called Diels-Alder reaction is used. The compound thus obtained is usually a cycloaddition reaction product having a double bond.

Although the reaction system of this cycloaddition reaction is not particularly limited, it can be reacted by either batch reaction or continuous reaction.
In addition, reaction of (a) terpene compound and (b) compound is 0.5-1.5 mol of (b) compound normally with respect to 1 mol of (a) terpene compound, Preferably 0.8- 1.2 moles.

  The reaction temperature for this cycloaddition reaction is usually 0 to 250 ° C, preferably 30 to 200 ° C, more preferably 50 to 180 ° C. If the reaction temperature is less than 0 ° C, the reaction rate is extremely slow. On the other hand, if it exceeds 250 ° C, side reactions such as polymerization become remarkable, which is not preferable.

  This cycloaddition reaction is usually performed without a catalyst, but may be performed using a catalyst. Although it does not specifically limit as a reaction catalyst, Preferably, acid catalysts, such as hydrochloric acid, a sulfuric acid, p-toluenesulfonic acid, activated clay, are normally used.

When the cycloaddition reaction product having a double bond thus obtained is subsequently subjected to a hydrogenation reaction to the double bond and further subjected to a reduction reaction, the desired dimethylol compound is obtained. However, the reduction reaction may be performed as it is without performing the hydrogenation reaction to the double bond. In this case, a dimethylol compound in which a double bond remains is obtained, but this double bond can be used for epoxidation or polymerization reaction.
There are no particular limitations on the double bond hydrogenation reaction and the reduction reaction method, and the following two methods are usually mentioned.
That is, in the first method, a hydrogenation reaction of a double bond of a cycloaddition reaction product with hydrogen is first performed in the presence of a catalyst, and then an unsaturated dicarboxylic acid, its acid anhydride, unsaturated This is a method of obtaining a dimethylol compound by reducing a dicarboxylic acid dialkyl ester.

  The catalyst used in the hydrogenation reaction is not particularly limited, and a metal catalyst for the hydrogenation reaction is usually used. Examples of the catalyst include nickel-based, copper-based, palladium-based, and platinum-based catalysts. The temperature of the hydrogenation reaction is preferably 0 to 300 ° C, more preferably 25 to 100 ° C. In this case, the amount of the metal catalyst used is usually 0.1 to 30% by weight, preferably 1 to 25% by weight, based on the cycloaddition reaction product.

  In addition, the reducing agent used in this reduction reaction is not particularly limited. For example, reducing agents such as lithium aluminum hydride, sodium borohydride, sodium bis (2-ethoxymethoxy) aluminum hydride are used. Can be mentioned.

  The reaction is usually carried out at a reaction temperature of 0 to 120 ° C, preferably 30 to 100 ° C. In this case, the amount of the reducing agent used is usually 1.6 to 3.0 mol, preferably 2.0 to 2.4 mol, with respect to 1 mol of the saturated cycloaddition reaction product as a raw material.

  In the second reduction reaction method, a double bond of a cycloaddition reaction product and an unsaturated dicarboxylic acid, its acid anhydride, and an unsaturated dicarboxylic acid dialkyl ester are obtained by catalytic hydrogenation reduction reaction with hydrogen using a catalyst. This is a method of obtaining a dimethylol compound by reduction.

  The catalyst used in that case is not particularly limited, and a commonly used catalytic reduction catalyst can be used. For example, a copper-chromium-based catalyst, a copper-iron-aluminum-based catalyst, a palladium-based catalyst, a platinum-based catalyst, a ruthenium-based metal catalyst, and the like can be given. Moreover, 0-500 degreeC is preferable and, as for temperature, More preferably, it is 100-300 degreeC. The amount of the metal catalyst used in this case is usually 0.1 to 50% by weight, preferably 1 to 30% by weight, based on the cycloaddition reaction product. In addition, after hydrogenating the double bond with the above hydrogenation catalyst, the reduced catalyst such as a copper-chromium catalyst or a copper-iron-aluminum catalyst is used as an unsaturated dicarboxylic acid, its acid anhydride, or an unsaturated dicarboxylic acid dialkyl. The ester can also be reduced. In this case, the temperature is 0 to 500 ° C., preferably 100 to 300 ° C., and the amount of the reduction catalyst used is usually 0.1 to 50% by weight, preferably based on the saturated cycloaddition reactant. Is 1 to 30% by weight.

  The dimethylol compound thus produced is obtained as a highly pure product by purification. The purification method is not particularly limited, and examples thereof include distillation, extraction, crystallization, recrystallization, and column chromatography.

  Next, the reaction between the dimethylol compound and the (meth) acrylic acid compound will be described. For this reaction, a method of esterifying the dimethylol compound and (meth) acrylic acid, a method of reacting the dimethylol compound and (meth) acrylic acid halide, a reaction of the dimethylol compound and (meth) acrylic anhydride. And a method of transesterifying the dimethylol compound with an acrylic ester such as methyl (meth) acrylate and ethyl (meth) acrylate. However, the reaction used in the present invention is not limited to these.

  Among the above reactions, the charging ratio of (meth) acrylic acid in the esterification reaction using (meth) acrylic acid is 0.1 to 20 mol, preferably 1 to 1 mol of dimethylol compound as a raw material. 10 moles. If the (meth) acrylic acid is less than 0.1 mol relative to 1 mol of the dimethylol compound, the esterification reaction may not proceed sufficiently. On the other hand, if it exceeds 20 mol, unreacted (meth) acrylic acid will be formed. Since it may remain and cost may increase, it is not preferable.

In addition, as a solvent, an aromatic compound such as benzene, toluene and xylene, a hydrocarbon compound such as hexane and cyclohexane, etc. are usually used as a solvent azeotropic with water, but (meth) acrylic acid or the like is used as a solvent. It also does not have to be used because it also serves.
When using a solvent, the usage-amount of this solvent is 30 to 1000 weight% with respect to the dimethylol compound which is a raw material, Preferably it is 50 to 700 weight%.

As the catalyst, sulfuric acid, hydrochloric acid, p-toluenesulfonic acid, boron trifluoride, ion exchange resin, activated clay, enzyme and the like can be used.
Although the usage-amount of a catalyst is not specifically limited, It is 0.0001-0.1 mol with respect to 1 mol of dimethylol compounds which are raw materials, Preferably it is 0.001-0.01 mol.

  In the esterification reaction, it is preferable to add a polymerization inhibitor. The polymerization inhibitor is not particularly limited as long as it is a compound capable of trapping radicals generated in the reaction system. For example, hydroquinone, methyl hydroquinone, hydroquinone monomethyl ether, phenothiazine, t-butyl hydroquinone, etc. are used. it can. The addition amount of the polymerization inhibitor is usually 5 to 10,000 ppm, preferably 20 to 5,000 ppm, more preferably 50 to 1,000 ppm with respect to the charged (meth) acrylic acid.

  The reaction temperature for esterification is 30 to 200 ° C, preferably 60 to 150 ° C. If the reaction temperature is less than 30 ° C., the reaction rate may be extremely slow. On the other hand, if it exceeds 200 ° C., side reactions such as polymerization become remarkable, which is not preferable. The esterification reaction is usually carried out under normal pressure, but can also be carried out under reduced pressure or under pressure depending on the boiling point of the solvent used.

Di (meth) acrylate compound of the present invention, the infrared absorption spectrum, 3,000～2,800Cm ^-1 due to C-H stretching, 1,725Cm ^-1 due to C = O stretching, C = C stretch due to 1,640~1,620cm ^-1, 1,500~1,350cm ^-1 due to C-H bending, the peak of 1,300～1,180Cm ^-1 due to C-O stretching Can be confirmed.
Further, according to the ¹ H-NMR chart, 0.79 to 1.86 ppm signal due to the bicyclo ring and side chain, 4.02 to 4.36 ppm signal due to the methylene group adjacent to the ester, and acrylate It can be confirmed by a signal of 5.80 to 6.42 ppm.

Furthermore, by ¹³ C-NMR and DEPT charts, 17.0-45.5 ppm signal due to the bicyclo ring and side chain, 66.5 and 67.1 ppm signals due to the methylene group adjacent to the ester, acrylate It can be confirmed by the resulting signals of 128.6-130.7 ppm and 166.4-166.5 ppm.

The curable composition in which the radical polymerization initiator is blended with the di (meth) acrylate compound of the present invention can be cured by radiation such as electron beams and ultraviolet rays, but ultraviolet rays can be obtained using a low-pressure or high-pressure mercury lamp or xenon lamp. It is preferable to cure by irradiating.
The curable composition of the present invention is a composition in which a radical polymerization initiator is blended with the di (meth) acrylate compound of the present invention, and the compound becomes an oligomer or polymer by the polymerization initiator. It is a concept that encompasses a wide range of things.

Here, the polymerization initiator (radical polymerization initiator) of the present invention will be described.
The radical polymerization initiator may be any initiator that undergoes radical polymerization.
Specifically, benzoin ethers such as benzyl, benzoin, benzylalkylketanol, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, p-dimethylaminoacetophenone, p-dimethylaminoacetophenone, etc. Benzophenone series such as acetophenone series, benzophenone, 4-chlorobenzophenone, o-benzoylbenzoic acid, 4-4′-dialkylaminobenzophenone, thioxanthone series such as thioxanthone, 2-chlorothioxanthone, 2-alkylthioxanthone, bis (2, Acylphosphine oxide such as 4,6-trimethylbenzoyl) -phenylphosphine oxide, 2-alkylanthraquinone and the like.

In the curable composition of the present invention, the blending ratio containing the di (meth) acrylate compound and the radical polymerization initiator is as follows.
Based on 100 parts by weight of the di (meth) acrylate compound, the radical polymerization initiator is 0.01 to 10 parts by weight, preferably 0.1 to 5.0 parts by weight, more preferably 0.3 to 4.0 parts by weight. It is. When the amount is less than 0.01 part by weight, radical polymerization does not proceed sufficiently. On the other hand, when the amount exceeds 10 parts by weight, extra components other than radical polymerization are added.

In the curable composition of the present invention, in addition to the above essential components, if necessary, other (meth) acrylate compounds and other additives as thermal polymerization inhibitors, antioxidants, plasticizers, dyes, A pigment, a resin compound, a suitable dilution solvent, and the like can be added.
The curable composition of the present invention can be cured with radiation such as an electron beam and ultraviolet rays, but ultraviolet irradiation is preferred. It is preferable to perform ultraviolet irradiation at 0.3-3 J / cm < ² >, More preferably, it is 0.5-2 J / cm < ² >. Since the intensity of ultraviolet rays is less than 0.3 J / cm ^2, more likely uncured portion remains, while the possibility that the resin portion discolored by excess exposure exceeds 3J / cm ² is higher, It is not preferable.
The curing device is not particularly specified as long as it is a commonly used electron beam or ultraviolet irradiation device.

EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated, this invention is not limited to these.
The following apparatus was used for the analysis in the following Example.
Infrared absorber (IR): FTIR-8100M manufactured by Shimadzu Corporation
Gas chromatography mass spectrometer (GC-MS): HEWLETT PACKARD, HP6890 GC System, column: HP-5MS (Crosslinked 5% Ph Me Siloxane), 30 m × 0.25 mm × 0.25 μm, ionization mode: EI
NMR: manufactured by JEOL Ltd., JNM-LA400, frequency 400 MHz (solvent: CDCl3, internal standard substance: tetramethylsilane)

Example 1
Production of di (meth) acrylate compounds:
In a 500 ml three-necked flask equipped with a condenser, a thermometer and a stirring rod, 71 g (0.5 mol) of α-terpinene and 58 g (0.5 mol) of fumaric acid were charged, and the temperature was raised while stirring. The reaction was carried out at ˜160 ° C. for 12 hours. After the reaction, 79 g of fumarated α-terpinene (yield 60% based on α-terpinene, purity 96%) was obtained by recrystallization from acetone.

Subsequently, 71 g (0.27 mol) of fumarated terpinene obtained above, 140 g of 2-propanol, and 0.7 g of a powdery 5% palladium carbon catalyst were charged into a 500 ml autoclave equipped with an electromagnetic stirrer. It is. Next, this was sealed, the atmosphere was replaced with nitrogen gas, and then introduced while applying a pressure of 15 kg / cm ² of hydrogen gas. And when stirring was started, internal temperature rose from 27 degreeC to 32 degreeC. The reaction was performed for 4 hours while maintaining the pressure at 15 to 20 kg / cm ² by supplementing the absorbed hydrogen. Thereafter, the obtained suspension was subjected to suction filtration with a Buchner funnel to separate the catalyst. Thereafter, the filtrate was concentrated under reduced pressure to obtain 69 g (yield 95%, purity 95%) of hydrogenated fumarated α-terpinene.

  Next, 500 ml of dehydrated tetrahydrofuran was placed in a 2 l four-necked flask equipped with a condenser, a thermometer, a stirring rod and a dropping funnel under a nitrogen stream, and 26.1 g (0.687 mol) of lithium aluminum hydride was added. . The mixture was refluxed at 65 ° C. for 30 minutes, then the heating was stopped, and a solution obtained by dissolving 60 g (0.224 mol) of hydrogenated fumarated α-terpinene obtained as described above in 300 ml of tetrahydrofuran was obtained. The solution was added dropwise over 3 hours. The mixture was refluxed at 65 ° C. for 12 hours, cooled to around 0 ° C., and 26 ml of water, 26 ml of 4N aqueous sodium hydroxide solution and 80 ml of water were sequentially added. The mixture was stirred until the gray portion disappeared, ethyl acetate was added, and the mixture was separated into an oil layer and an aqueous layer. The solvent was removed from the oil layer by distillation under reduced pressure to obtain 53 g of a crude product. This was purified by column chromatography to obtain 20 g of white crystals of dimethylol compound (yield 40%, purity 99%).

  Next, in a 300 ml four-necked flask equipped with a Dean-Stark tube, a cooling tube, a thermometer, and a stirring bar, 20 g (0.088 mol) of the dimethylol compound obtained as described above, 100 g of toluene, and 12.1 of acrylic acid. 7 g (0.176 mol), 2.5 g hydroquinone monomethyl ether, and 2.0 g ion exchange resin (Amberlyst 15E, manufactured by Rohm and Haas) were charged. The mixture was refluxed at 100 ° C. for 12 hours under reduced pressure, and the resulting mixture was filtered to remove the catalyst. Subsequently, toluene was distilled off at 80 ° C. under reduced pressure to obtain 20.6 g of di (meth) acrylate compound A (yield 70%, purity 72%).

The analysis result of the obtained di (meth) acrylate compound A is shown in FIGS. In addition, the symbol which shows attribution of Table 1 and 2 shows the position shown to Formula (IV).
Analysis results 1) FIG. 1: IR chart 3,000-2,800 cm ⁻¹ : C—H stretch, 1,725 cm ⁻¹ : C═O stretch, 1,640-1,620 cm ⁻¹ : C = C stretch , 1,500 to 1,350 cm ⁻¹ : C—H deformation angle, 1,300 to 1,180 cm ⁻¹ : C—O stretching 2) FIG. 2: GC-MS chart m / z = 291 [M−C ₃ H ₇ ] + was observed.
3) FIG. 3: ¹ H-NMR chart 4) FIG. 4: ¹³ C-NMR chart 5) FIG. 5: DEPT chart

Production of the curable composition:
20 g of the di (meth) acrylate compound A and 0.5 g of benzoyl as a radical photopolymerization initiator were mixed, and the mixture was filtered through a filter to obtain a photosensitive composition of the present invention.
(Curing shrinkage)
After leaving the said photosensitive composition in a 25 degreeC thermostat, specific gravity D1 was measured using the pycnometer. Next, the photosensitive composition was sandwiched between glass plates so that the thickness of the resulting coating film was 100 μm, and irradiated with a metal halide lamp at about 1 J / cm ² . In accordance with JIS Z8807: 1976, the solid specific gravity D2 of this coating film was determined, and the cure shrinkage was determined by the following formula.
The measurement results of the curing shrinkage are shown in Table 3.
Curing shrinkage (%) = [(D2-D1) / D2] × 100

Furthermore, 25 g of dipropylene glycol monomethyl ether acetate / solvent naphtha (50/50) as a solvent was added to a mixture of 20 g of the di (meth) acrylate compound A and 0.5 g of benzoyl as a photoradical polymerization initiator, and a reaction temperature of 70 Mechanical stirring was performed at 0 ° C. to obtain Resin B.
25 g of resin B, 7.5 g of triglycidyl isocyanurate, 0.5 g of benzoyl, 0.5 g of BYK357 (Big Chemie antifoaming agent), 0.5 g of BYK054 (Big Chemie surface smoothing agent), phthalocyanine green (manufactured by Sanyo Dye) 0 0.5 g, 10 g of talc and 5 g of barium sulfate were mixed and applied to a copper-clad laminate subjected to surface mechanical polishing so as to have a film thickness of 40 μm using a screen printer LS15GX manufactured by Neurong Precision Industry Co., Ltd. The coated substrate was left in a dryer at 70 ° C. for 30 minutes, and an exposure pattern film was placed thereon with a parallel light exposure machine to expose a light amount of 250 mJ / cm ² . After the exposure, development was performed with toluene for 60 seconds at a spray pressure of 1.5 kg / cm ² . After washing with water, it was cured by heating in a hot air dryer at 160 ° C. for 1 hour.
About the test piece which has the obtained cured film, glass transition temperature (Tg) measurement, water absorption, and evaluation of the resolution were performed. The results are shown in Table 3.

The test method and the evaluation method are as follows.
(Measurement of glass transition temperature (Tg))
The coating film was peeled off from the substrate coated once or twice, and measured by the TMA tensile test according to the test method of JIS C: 6481.
(Measurement of water absorption)
The sample was placed in a 120 ° C. dryer overnight and dried sufficiently, and then the weight (W0) was measured.
The sample was then placed in a pressure cooker (121 ° C., 2 atm) for 1 hour. After taking out from the pressure cooker, it was cooled with running water for 3 minutes, wiped with a cloth, left to stand for 2 minutes, then measured for weight (W1), and the water absorption was determined by the following formula.
Water absorption (%) = [(W1-W0) / W0] × 100
(Resolution evaluation)
Three types of test pieces having a line width of 100, 50, and 25 μm of the cured resist film were prepared, and cross-sectional observation was performed. The exposure was 200 mJ / cm ² . For evaluation, 20 arbitrary places were selected as test parts, observed with a microscope, and displayed as the number of normal parts with respect to the number of examinations.

Comparative Example 1
Diglycidyl methacrylate 20 g, benzoyl 0.25 g, and p-methoxybenzenediazonium hexafluorophosphate 0.25 g were mixed to obtain a photosensitive composition, which was evaluated in the same manner as in Example 1. The evaluation results are shown in Table 3.

  The di (meth) acrylate compound of the present invention and the curable composition containing the same can be used as a photosensitive material such as a resist, a coating material such as an ink and a paint, a raw material for an adhesive, a building material, and the like.

2 is an IR spectrum chart of di (meth) acrylate compound A obtained in Example 1. FIG. 2 is a GC-MS spectrum chart of di (meth) acrylate compound A obtained in Example 1. FIG. 2 is a ¹ H-NMR chart of di (meth) acrylate compound A obtained in Example 1. FIG. 2 is a ¹³ C-NMR chart of di (meth) acrylate compound A obtained in Example 1. FIG. 2 is a DEPT chart of di (meth) acrylate compound A obtained in Example 1. FIG.

Claims (4)

  A di (meth) acrylate compound obtained by reacting a dimethylol compound having a terpene skeleton with a (meth) acrylic acid compound. The di (meth) acrylate compound according to claim 1, wherein the di (meth) acrylate compound is represented by the following formula (I).

[In the formula (I), R 1, R 2, R 3, R 4, R 5, R 6 are the same or different from each other, and are represented by a hydrogen atom or a formula C _n H _{2n + 1} where _n is an integer of 1-5. Represents a hydrocarbon group. R7 is a hydrogen atom or a methyl group. ] The di (meth) acrylate compound according to claim 2, wherein the compound represented by the formula (I) is the following formula (II).

A curable composition comprising 0.01 to 5 parts by weight of a radical polymerization initiator with respect to 100 parts by weight of the di (meth) acrylate compound according to any one of claims 1 to 3.

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