KR101916876B1 - Photo curable isosorbide derivative compound and method for preparing the same - Google Patents

Abstract

이에 의하여, 아이소소바이드 화합물에 결합된 히드록시기 대신에 메타크릴레이트기를 치환하여 제거함으로써, 이를 치과용 충전재로 적용했을 때, 수분의 접촉에 따른 손상을 감소시켜 기계적 물성 및 내구성 저하의 원인이 되는 수축률 및 수분흡수율을 줄일 수 있으며, 압축강도 및 굴곡강도 등의 기계적 특성을 개선시킬 수 있다.The present invention relates to an isosorbide derivative compound represented by the following structural formula (1).
[Structural formula 1]

As a result, when a methacrylate group is substituted for a hydroxy group bonded to an isosorbide compound to remove the methacrylate group, it is possible to reduce damage due to contact with water when the filler is used as a dental filler, thereby reducing the shrinkage And the water absorption rate can be reduced, and mechanical properties such as compressive strength and flexural strength can be improved.

Description

[0001] PHOTO CURABLE ISOSORBIDE DERIVATIVE COMPOUND AND METHOD FOR PREPARING THE SAME [0002]

The present invention relates to a photo-curable isosorbide derivative and a process for producing the same. More particularly, the present invention relates to a photo-curable isosorbide derivative compound having improved water absorption and a process for producing the same.

Curable materials such as adhesives, adhesives, sealants, coatings and paints are currently being used in various industrial fields such as packaging, bookbinding, automotive, electronics, precision, optical products, woodworking, plywood, It is widely used for home use, and its use has become widespread, and recently it has also been applied to concrete. Such adhesives and the like are manufactured in the form of a mixture of chemical materials based on a synthetic resin. Since the volatile organic compounds (VOC) are added due to the organic solvent (solvent) used in the manufacturing process and various volatile additives added to improve the physical properties, , Dioxins, and environmental hormones. In recent years, environmental regulations under international agreements have strictly restricted the production and use of these harmful substances. Furthermore, the EU has used such regulations as a means of new trade sanctions. In keeping with this trend, conventional solvent type adhesives have been replaced by water-soluble, solvent-free, hot-melt type and the like. Furthermore, not only these adhesive materials, but most of the fine chemical materials we currently use are petrochemical products derived from the Oil Refinery Process. However, international oil prices are steadily rising due to a decrease in reserves and a surge in demand centering on BRICs. As international conventions that strictly regulate greenhouse gas emissions become effective, future use of irreversible fossil resources such as oil will lead to enormous environmental costs . Therefore, many efforts have been made to obtain existing petroleum-derived fine chemical products from new resources, and the most representative example is to use carbohydrate-based biomass as a supply source. The natural world produces about 170 billion tons of carbohydrates every year through photosynthesis. Human beings use only about 3% of them as food, paper, furniture, and building materials. Thus, fine chemicals manufactured from renewable and sustainable carbohydrate biomass are expected to replace petrochemicals. Accordingly, in order to replace conventional light source curing adhesive materials derived from petroleum resources, development of a technology for synthesizing compounds having predetermined adhesion or adhesion properties using such environmentally friendly carbohydrate-based biomass is required. As a representative example of the carbohydrate-based biomass, there is an isosorbide derivative.

Isosorbide is a heterocyclic compound derived from glucose, which can be obtained by hydrogenating glucose to form sorbitol, which can be double dehydrated. The isosorbide has a V-shaped structure in which two tetrahydrofuran rings are bonded at an angle of 120 ° and has a hydroxyl group at carbon positions 2 and 6. Isosorbide is a compound of a solid structure having optical asymmetry, and derivatives thereof are useful as raw materials for pharmaceutical raw materials and high-functional industrial materials in that they exhibit specific functions. In addition, isosorbide is excellent in optical properties and thermal properties and is used in optical electronic components such as optical disk substrates, optical fibers, and lenses. In addition, the composition of the present invention can be utilized as a composition of a dental filler by applying an isosorbide derivative. Bis (4- (2-hydroxy-3-methacryloyloxypropoxy) phenyl) propane (Bis-GMA) which is the bisphenol system most commonly used as a prepolymer of a dental material composition . This is mainly used for matrix resin because it has advantages such as low volatility and polymerization shrinkage and good strength of polymeric compound using it. However, bisphenol compound plays a role like estrogen in the human body and can cause endocrine disruption . In order to solve such a problem, there has been an effort to replace it with an isosorbide-based compound derived from biomass which is harmless to human body.

Since the compound based on isosorbide contains a hydroxyl group (-OH) in a compound, when it is used as a dental filler, etc., the mechanical strength is weakened due to the property of absorbing moisture and there is a problem that the esthetics is lowered due to shrinkage of the material itself .

In addition, since the hydroxy group has a high material viscosity, it is disadvantageous in manufacturing a composite containing filler.

DISCLOSURE OF THE INVENTION An object of the present invention is to solve the above-mentioned problems, and an object of the present invention is to solve the above-mentioned problems by providing a water- To provide this significantly improved isosorbide derivative compound.

In one aspect of the present invention, there is provided an isosorbide derivative represented by the following structural formula (1).

[Structural formula 1]

In formula 1,

m and n may be the same or different from each other, and each independently is an integer of 1 to 5,

Each R ¹ is independently selected from a hydrogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, a C 2 to C 6 alkynyl group, a C 5 to C 6 cycloalkyl group, and a C 6 to C 10 aryl group.

Each of R < ¹ > may independently be a methyl group.

M and n may be the same or different from each other, and may be independently any one of integers of 1 to 3.

The compound represented by Formula 1 may be a compound represented by Formula 1 below.

[Chemical Formula 1]

According to another aspect of the present invention, there is provided a process for preparing a compound represented by the following formula (1): (a) reacting a compound 1 to prepare a compound 2; And (b) reacting Compound 2 with Compound 3 to prepare an isosorbide derivative represented by Compound 4; And a method for producing the same.

[Reaction Scheme 1]

In the above Reaction Scheme 1,

m and n may be the same or different from each other, and each independently is an integer of 1 to 5,

Each R ¹ is independently selected from a hydrogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, a C 2 to C 6 alkynyl group, a C 5 to C 6 cycloalkyl group, and a C 6 to C 10 aryl group.

The step (a) may be a step of performing a reduction reaction using a reducing agent.

The step (b) may be carried out at 40 to 80 < 0 > C.

And may contain a polymerization inhibitor in the step (b).

The polymerization inhibitor may be at least one selected from the group consisting of hydroquinone, methyl hydroquinone, and monomethyl ether hydroquinone.

According to another aspect of the present invention, there is provided a dental material composition comprising the isosorbide derivative compound.

The isosorbide derivative compound; Initiator; And fillers; . ≪ / RTI >

100 parts by weight of the isosorbide derivative compound; 0.1 to 5 parts by weight of the initiator; And 50 to 500 parts by weight of the filler; . ≪ / RTI >

The initiator may be a photopolymerization initiator.

Wherein the initiator is selected from the group consisting of camphoquinone, ethyl-4-dimethylamino benzoate, tertiary amine initiator, diphenyl iodonium chloride, diphenyl iodonium hexafluorophosphate, diphenyl Iodonium tetrafluoroborate, tolylcumyl iodonium tetrakis (pentafluorophenyl) borate, acyl, bisacylphosphine oxide, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, bis 2,6-dimethoxybenzoyl) - (2,4,4-trimethylpentyl) phosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, 2- 2-methyl-1-phenylpropan-1-one, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, 2-hydroxy- Ethyl 2,4,6-trimethylbenzyl phenylphosphinate, and the like.

Wherein the filler is selected from the group consisting of barium glass fillers, barium aluminosilicates, synthetic amorphous silicas, crystalline silicas, barium silicates, barium borosilicates, barium fluoroaluminosilicates, But are not limited to, barium fluoroaluminoborosilicate, barium aluminoborosilicate, strontium silicate, strontium borosilicate, strontium aluminoborosilicate, calcium silicate, May be at least one selected from alumino silicate, silicon nitrides, titanium dioxide, calcium hydroxyapatite, zirconia, and bioactive glass. have.

In the present invention, when a methacrylate group is substituted for a hydroxy group bonded to an isosorbide compound to remove the methacrylate group and applied to the dental filler, the damage caused by contact with water is reduced, thereby reducing the shrinkage And the water absorption rate can be reduced, and mechanical properties such as compressive strength and flexural strength can be improved.

FIG. 1 shows nuclear magnetic resonance (NMR) analysis results of the compound prepared according to Example 1. FIG.
Fig. 2 is a graph showing the results of analysis of flexural strength and compressive strength of the compound prepared according to Example 1, Comparative Example 1 and Comparative Example 3. Fig.
3 is a graph showing the results of analysis of flexural strength and compressive strength of the composition prepared according to Example 2, Comparative Example 2, and Comparative Example 4. FIG.
Fig. 4 is a graph showing the results of analysis of resin shrinkage ratios of the compounds prepared according to Example 1, Comparative Example 1 and Comparative Example 3. Fig.
5 is a graph showing the water absorption of the compound prepared according to Example 1, Comparative Example 1 and Comparative Example 3 and the results of water absorption analysis of the composition prepared according to Example 2, Comparative Example 2 and Comparative Example 4, to be.

The invention is capable of various modifications and may have various embodiments, and particular embodiments are exemplified and will be described in detail in the detailed description. It is to be understood, however, that the invention is not to be limited to the specific embodiments, but includes all modifications, equivalents, and alternatives falling within the spirit and scope of the invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail with reference to the accompanying drawings.

Furthermore, terms including an ordinal number such as first, second, etc. to be used below can be used to describe various elements, but the constituent elements are not limited by the terms. The terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be referred to as a second component, and similarly, the second component may also be referred to as a first component.

Also, when an element is referred to as being "formed" or "laminated" on another element, it may be directly attached or laminated to the front surface or one surface of the other element, It will be appreciated that other components may be present in the < / RTI >

The singular expressions include plural expressions unless the context clearly dictates otherwise. In the present application, the terms "comprises" or "having" and the like are used to specify that there is a feature, a number, a step, an operation, an element, a component or a combination thereof described in the specification, But do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

Hereinafter, the isosorbide derivative compound of the present invention will be described.

The present invention provides an isosorbide derivative compound represented by the following structural formula (1).

[Structural formula 1]

In formula 1,

m and n may be the same or different from each other, and each independently is an integer of 1 to 5,

Each R ¹ is independently selected from a hydrogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, a C 2 to C 6 alkynyl group, a C 5 to C 6 cycloalkyl group, and a C 6 to C 10 aryl group.

Preferably, each of R < ¹ > is independently a methyl group.

Preferably, m and n may be the same or different from each other, and each independently may be an integer of 1 to 3.

The compound represented by Formula 1 may be a compound represented by Formula 1 below.

[Chemical Formula 1]

The isosorbide derivative compound can be prepared by a process as shown in Reaction Scheme 1 below.

[Reaction Scheme 1]

In the above Reaction Scheme 1,

m and n may be the same or different from each other, and each independently is an integer of 1 to 5,

Each R ¹ is independently selected from a hydrogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, a C 2 to C 6 alkynyl group, a C 5 to C 6 cycloalkyl group, and a C 6 to C 10 aryl group.

First, compound 1 is reacted to prepare compound 2 (step a).

The step (a) may be a step of performing a reduction reaction using a reducing agent.

Next, Compound 2 is reacted with Compound 3 to obtain Compound 4 Isosobaid  A derivative compound is prepared (step b).

The step (b) may be carried out at a temperature of 40 to 80 캜, preferably 40 to 70 캜, more preferably 40 to 60 캜.

In the step (b), a polymerization inhibitor may be included. Preferably, hydroquinone, methyl hydroquinone, and monomethyl ether hydroquinone may be used.

The reaction may be carried out for 3 to 48 hours, preferably 4 to 36 hours, more preferably 5 to 30 hours. However, the time during which the reaction is carried out may vary depending on the reaction temperature.

There is provided a dental material composition comprising the isosorbide derivative compound represented by the structural formula (1).

An isosorbide derivative compound represented by the structural formula 1; Initiator; And fillers; , Preferably 100 parts by weight of the isosorbide derivative compound represented by Structural Formula 1; 0.1 to 5 parts by weight of the initiator; And 50 to 500 parts by weight of the filler; . ≪ / RTI >

The initiator is a photopolymerization initiator and is preferably selected from the group consisting of camphoquinone, ethyl-4-dimethylamino benzoate, tertiary amine initiator, diphenyl iodonium chloride, diphenyl iodonium (Pentafluorophenyl) borate, acyl, bisacylphosphine oxide, bis (2,4,6-trimethylbenzoyl) phenyl (diphenyliodonium) tetrafluoroborate, diphenyl iodonium tetrafluoroborate, tolylcumyl iodonium tetrakis (2,6-dimethoxybenzoyl) - (2,4,4-trimethylpentyl) phosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine 2-methyl-1-phenylpropan-1-one, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, 2-hydroxy- Propane-1-one, ethyl 2,4,6-trimethylbenzyl phenylphosphinate, and the like.

The filler may be selected from the group consisting of barium glass filler, barium aluminosilicate, synthetic amorphous silica, crystalline silica, barium silicate, barium borosilicate, barium fluoroaluminosilicate, But are not limited to, barium fluoroaluminoborosilicate, barium aluminoborosilicate, strontium silicate, strontium borosilicate, strontium aluminoborosilicate, calcium silicate, Alumino silicate, silicon nitrides, titanium dioxide, calcium hydroxyapatite, zirconia, bioactive glass, and the like can be used.

[Example]

Example  One: Isosobaid  The derivative compound ( ISB - IPMA )

(Step 1)

Isosorbide (1.0 g, 6.8 mmol) and KOH (2.8 g, 42 mmol) were placed in a 50 mL round-bottomed flask and covered with rubber stopper. Dry DMSO (5 mL) was then added under N ₂ atmosphere. 40 bases were immersed in a round bottom flask containing the reaction solution and thermally equilibrated. When thermal equilibrium was established inside the flask, epibromohydrin (3.84g, 28mmol) was slowly added dropwise via syringe. At this time, it was observed that the color of the suspension inside the flask gradually changed to dark brown depending on the drop amount. After dropwise addition, the mixture was reacted by stirring at 40 for 2 hours. The reaction solution was then filtered through a filter to remove salts from the residue, the filtrate was diluted with an appropriate amount of methylene chloride, and transferred to a separatory funnel. Washed with distilled water and brine in this order, and the organic layer was washed with water (MgSO4), filtered, concentrated under reduced pressure and purified by flash chromatography (hexane: ethyl acetate = 1: 1) to give an isospoid Compound (a) was obtained (1.1 g, 4.3 mmole, 63%).

The reaction of Step 1 is shown in the following Reaction Scheme 2.

[Reaction Scheme 2]

(Step 2)

The compound a (5 g, 19 mmol) prepared in accordance with the above step 1 was diluted with THF (50 mL), and LiAlH ₄ (1.433 g, 37 mmol) and THF (50 mL) were added to a 250 mL round bottom flask under nitrogen atmosphere. Respectively. Then, the reaction was carried out at room temperature (25 ° C) for 24 hours with stirring. To remove remaining LiAlH ₄ in the reaction solution, the temperature of the reaction solution was lowered to -10 ° C, and a small amount of distilled water was added. The reaction solution was diluted with an appropriate amount of methylene chloride and transferred to a separating funnel. After washing several times with an appropriate amount of distilled water and brine, the organic layer was subjected to water removal (MgSO ₄ ), followed by filtration and concentration under reduced pressure to obtain Compound (b) mmol 61%).

The reaction of Step 2 is shown in Scheme 3 shown below.

[Reaction Scheme 3]

(Step 3)

1.0 g (1 eq) of the compound b prepared in a 50 ml round-bottomed flask and hydroquinone (2,000 ppm, 0.01 g) as a polymerization inhibitor were placed and the flask was charged with methacrylic anhydride (C ₈ H ₁₀ O _{3 ,} 3.5 g (6 eq) of MAAH and 0.3 g of pyridine capable of serving as a catalyst or solvent were added thereto, and the mixture was reacted at 50 DEG C for 24 hours with stirring.

After the reaction was completed, excess H ₂ O was added and stirred at ambient temperature for 3 hours. Thereafter, an excessive amount of potassium carbonate was added until a precipitate of potassium carbonate (K ₂ CO ₃ ) was observed, and then potassium carbonate was filtered out by filtration. The filtered material was loaded with methylene chloride (MC) and 10 wt% aqueous potassium carbonate (K ₂ CO ₃ ) solution to separate the organic layer containing methylene chloride.

The separated organic layer was subjected to rotary distillation to remove methylene chloride, and the resulting material was purified by column chromatography using hexane (ethyl acetate = 3: 1) to obtain a pure isosorbide derivative compound (c).

0.1 wt% (1,000 ppm) hydroquinone was added to the isosorbide derivative compound as a polymerization inhibitor and stored.

The reaction of Step 3 is shown in Scheme 4 shown below.

[Reaction Scheme 4]

¹ H NMR analysis of the isosorbide derivative compound (ISB-IPMA) having improved water absorption properties is shown in FIG. 1, and ¹ H NMR data thereof is as follows.

_{^{1 H NMR (CDCl 3, 300MHz}} ): δ6.15-6.06 (d, 2H), 5.62-5.53 (d, 2H), 5.21-5.03 (m, 2H), 4.66-4.59 (m, 1H), 4.48- 6H), 1.43-1.18 (d, 6H), 4.44 (m, 1H)

Example  2: Isosobaid  The derivative compound ( ISB - IPMA ) ≪ / RTI >

Barium aluminosilicate (60 wt% based on the total amount), which is a filler, was added to the compound prepared according to Example 1. Thereafter, 1 wt% of an initiator composed of camphoquinone / ethyl-4-dimethylamino benzoate (1: 2) was added and mixed three times for 3 minutes at 2000 rpm using a planetary vacuum mixer to prepare the composition of Example 2.

Comparative Example  One: BisGMA / TEGDMA  compound

(BisGMA: TEGDMA = 6: 4 weight ratio (wt%)) 3 g of the compound represented by the following formula 2 (BisGMA) and 2 g of the compound represented by the following formula 3 (TEGDMA) Min. ≪ / RTI >

(2)

(3)

Comparative Example  2: BisGMA / TEGDMA  Composition

To the mixture of Comparative Example 1, 7.5 g of barium aluminosilicate as a filler (60 wt% based on the total amount) was added and 1 wt% of an initiator composed of camphoquinone / ethyl-4-dimethylamino benzoate (1: 2) And mixed three times for 3 minutes at 2000 rpm using a planetary vacuum mixer to prepare the BisGMA / TEGDMA composition of Comparative Example 2. [

Comparative Example  3: IsoGMA  Compound manufacturing

(Step 1)

Isosorbide (1.0 g, 6.8 mmol) and KOH (2.8 g, 42 mmol) were placed in a 50 mL round-bottomed flask and covered with a rubber stopper, followed by dry DMSO (5 mL) under N ₂ atmosphere. 40 bases were immersed in a round bottom flask containing the reaction solution and thermally equilibrated. When thermal equilibrium was established inside the flask, epibromohydrin (3.84g, 28mmol) was slowly added dropwise via syringe. At this time, it was observed that the color of the suspension inside the flask gradually changed to dark brown depending on the drop amount. After dropwise addition, the mixture was reacted by stirring at 40 for 2 hours. Thereafter, the reaction solution was filtered through a syringe filter to remove salts from the residue, the filtrate was diluted with an appropriate amount of methylene chloride, and then transferred to a separating funnel. Washed with distilled water and brine in this order, and the organic layer was washed with water (MgSO4), filtered, concentrated under reduced pressure and purified by flash chromatography (hexane: ethyl acetate = 1: 1) to give an isospoid Compound (a) was obtained (1.1 g, 4.3 mmole, 63%).

The reaction of Step 1 is as shown in Reaction Scheme 2 above.

(Step 2)

(A) (1 g, 3.8 mmol), diphenyl picrylhydrazyl (10 mg, 0.6 mmol), and methacrylic acid (2 g) were added to a 100 mL round bottom flask under a nitrogen atmosphere. acid (7 mL, 78 mmol) were added and stirred. Then, 3 drops of tetraethylamine (TEA) was added dropwise and the mixture was stirred at 100 for 4 hours. After completion of the reaction, a dark brown reaction solution was obtained. The reaction solution was transferred to a separatory funnel, washed 5 times with 20 wt% NaHCO ₃ aqueous solution and treated with water / ethyl acetate (water / EA). The organic layer of the treated product was distilled to remove the solvent, and a viscous colorless compound (IsoGMA) was prepared by flash chromatography of hexane: ethyl acetate (1: 2, v / v) (1.23 g, 2.9 mmole, 75%).

The reaction of Step 2 is shown in Reaction Scheme 5 shown below.

[Reaction Scheme 5]

Comparative Example  4: IsoGMA  Composition

A barium aluminosilicate (60 wt% based on the total amount), which is a filler, was added to the IsoGMA compound prepared according to Comparative Example 3. Then, 1 wt% of an initiator composed of camphoquinone / ethyl-4-dimethylamino benzoate (1: 2) was added and mixed three times for 3 minutes at 2000 rpm using a planetary vacuum mixer to prepare a composition of Comparative Example 4.

[Chemical Formula 5]

[Test Example]

Test Example  1: Compressive Strength and Flexural Strength Analysis

Fig. 2 shows the results of measurement of compressive strength and flexural strength of the compound prepared according to Example 1, Comparative Example 1 and Comparative Example 3. Fig. 3 shows the results of measurement of compressive strength and flexural strength of the compositions prepared according to Example 2, Comparative Example 2 and Comparative Example 4. [

Specimens for measuring the compressive strength were prepared by filling a cylindrical (? X L = 4 x 6 mm) SUS mold with the prepared resin mixture and using a 3M ESPE Elipar ^TM The specimen was irradiated with visible light for 40 seconds on the front and back sides using a S10 spot cure apparatus. For the flexural strength measurement, specimens were filled in a rectangular parallelepiped (H x W x L = 2 x 2 x 25 mm) SUS mold and irradiated with visible light for 20 sec each by dividing each side with a spot cure device , And the other side was irradiated by the same method. The compressive strength of the specimens was measured at Lord Sell 5000N, crosshead speed 1mm / min using a universal testing machine UTM (Universal Testing Machine) Shimadzu AGS-X. The strength was measured. Measurement was carried out according to the international standard test (compression strength: ISO9917, flexural strength: ISO4049).

2 and 3, the compressive strength and flexural strength of the isosorbide derivative compound prepared according to Example 1 were found to be similar to those of the compound prepared according to Comparative Example 3. However, it was confirmed that the composition comprising the isosorbide derivative compound prepared according to Example 2 had higher flexural strength and compressive strength than the composition prepared according to Comparative Example 4.

Thus, it was found that the compressive strength and flexural strength of the composition of Example 2 were improved compared to that of the compound of Example 1 in the form of a resin.

Test Example 2: Shrinkage resin compare analysis

Fig. 4 shows the results of the resin shrinkage analysis of the compounds prepared according to Example 1, Comparative Example 1 and Comparative Example 3. Fig.

In order to measure the shrinkage rate, 1 mL of the composition was dropped onto a slide glass, covered with a stainless steel plate, and then irradiated with light under a slide glass to microscopically move the sample in the irradiated direction. Using a linear variable differential transducer (LVDT) Were measured.

4, the resin shrinkage rate of the isosorbide derivative compound prepared in Example 1 was 3.3%, and the resin shrinkage rate of the compound prepared according to Comparative Example 3 was 5.8%, so that the compound of Example 1 was compared with Comparative Example 1 And the compound of Comparative Example 3, it is analyzed that the hardening shrinkage is relatively high and the dimensional stability is high, and the peeling problem in adhesion can be improved.

Test Example 3: Water Sorption Analysis

5 (a) shows the results of water absorption analysis of the compound prepared according to Example 1, Comparative Examples 1 and 3, (b) shows the results of the water absorption analysis of the composition prepared according to Example 2, Comparative Example 2 and Comparative Example 4 The results of the moisture absorption analysis are shown

Measurement specimens for measuring water absorption were prepared by filling a cylindrical resin SUS mold with a prepared resin mixture (? X L = 15 x 1 mm) and using a 3M ESPE Elipar ^TM S10 spot cure apparatus was used to irradiate visible light for 8 seconds around the center and center for 20 seconds, respectively. The water absorption measurement was carried out in accordance with the International Standard Test (ISO4049) as follows. The weight of the prepared specimens was measured, and the specimens were dried until the specimens were uniformly weighed. The weight of M ₀ and was wiped with a specimen of phosphate buffer solution (Phosphate buffer solution, PBS, pH = 7.41) was taken out after 10ml put in a containing vial was allowed to stand for 7 days 37 ℃ oven smooth the sample surface absorptive good paper. Then, it was put in a desiccator for 1 hour, dried and then weighed. At this time, the sample was dried until the weight of the specimen was constant. This weight is called M ₇ . The water absorption was calculated by the following equation.

WS (/ / mm ³ ) = M ₇ - M ₀ / V

Where V is the initial volume of the sample.

5 shows that the compound of Example 1 and the composition of Example 2 have lower water absorption than the compounds of Comparative Examples 1 and 3 and the compositions of Comparative Examples 2 and 4, .

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It is possible.

Claims (15)

An isosorbide derivative compound represented by the following structural formula (1).
[Structural formula 1]

In formula 1,
m and n may be the same or different from each other and are 1 or 2,
Each R < ¹ > is independently a hydrogen atom or a methyl group. The method according to claim 1,
Wherein each of R < ¹ > is independently a methyl group. The method according to claim 1,
m and n are 1. 5. The isosorbide derivative compound according to claim 1, The method according to claim 1,
Wherein the compound represented by the structural formula (1) is a compound represented by the following general formula (1).
[Chemical Formula 1]

As shown in Reaction Scheme 1 below,
(a) reacting Compound 1 to prepare Compound 2; And
(b) reacting Compound 2 with Compound 3 to prepare an isosorbide derivative represented by Compound 4; To
Wherein the isosorbide derivative is a compound represented by the following formula (1).
[Reaction Scheme 1]

In the above Reaction Scheme 1,
m and n may be the same or different from each other and are 1 or 2,
Each R < ¹ > is independently a hydrogen atom or a methyl group. 6. The method of claim 5,
Wherein the step (a) is a step of performing a reduction reaction using a reducing agent. 6. The method of claim 5,
Wherein step (b) is carried out at 40 to < RTI ID = 0.0 > 80 C. < / RTI > 6. The method of claim 5,
Wherein the step (b) comprises a polymerization inhibitor. 9. The method of claim 8,
Wherein the polymerization inhibitor is at least one selected from the group consisting of hydroquinone, methyl hydroquinone, and monomethyl ether hydroquinone. A dental material composition comprising the isosorbide derivative of claim 1. 11. The method of claim 10,
An isosorbide derivative compound of claim 1;
Initiator; And
Filler;
0.0 > dental < / RTI > 12. The method of claim 11,
100 parts by weight of the isosorbide derivative compound of claim 1;
0.1 to 5 parts by weight of the initiator; And
50 to 500 parts by weight of the filler;
Dental material composition. 12. The method of claim 11,
Wherein the initiator is a photopolymerization initiator. 12. The method of claim 11,
Wherein the initiator is selected from the group consisting of camphoquinone, ethyl-4-dimethylamino benzoate, tertiary amine initiator, diphenyl iodonium chloride, diphenyl iodonium hexafluorophosphate, diphenyl Iodonium tetrafluoroborate, tolylcumyl iodonium tetrakis (pentafluorophenyl) borate, acylphosphine oxide, bisacylphosphine oxide, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide (2,6-dimethoxybenzoyl) - (2,4,4-trimethylpentyl) phosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, 2 2-methyl-1-phenylpropan-1-one, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, 2- And ethyl 2,4,6-trimethylbenzyl phenylphosphinate. The dental material composition according to claim 1, 12. The method of claim 11,
Wherein the filler is selected from the group consisting of barium glass fillers, barium aluminosilicates, synthetic amorphous silicas, crystalline silicas, barium silicates, barium borosilicates, barium fluoroaluminosilicates, But are not limited to, barium fluoroaluminoborosilicate, barium aluminoborosilicate, strontium silicate, strontium borosilicate, strontium aluminoborosilicate, calcium silicate, At least one selected from alumino silicate, silicon nitrides, titanium dioxide, calcium hydroxyapatite, zirconia, and bioactive glass may be used. Characterized dental material composition .

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