KR20190047223A - Photo curable isosorbide derivative compound and method for preparing the same - Google Patents

Abstract

The present invention relates to an isosorbide derivative compound represented by structural formula 1 that a methacrylate group is substituted for a hydroxy group, bonded to the isosorbide derivative compound, to remove thereof and remove thereof. Therefore, it is possible to improve mechanical properties such as compressive strength, flexural strength and the like by reducing damage due to contact of moisture when applying the same to a dental filler.

Description

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

The present invention relates to a photocurable isosorbide derivative compound and a process for producing the same. More particularly, the present invention relates to an isosorbide derivative compound having a symmetrical structure in which a terminal is substituted with a methacrylate group and contains two ester bonds, .

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 In keeping with this trend, conventional solvent type adhesives have been replaced by water-soluble, solvent-free, hot-melt type and the like.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 because 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.

Conventional isosorbide-based compounds contain a hydroxy group (-OH) in a compound. Therefore, when the compound is used as a dental filler or the like, the mechanical strength is weakened due to the property of absorbing moisture, and the esthetics is deteriorated 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.

It is an object of the present invention to provide a photo-curable isosorbide derivative compound that can be used as an environment-friendly material that can replace a bisphenol-based polymer material from which an environmental hormone can be eluted.

In addition, when a methacrylate group is substituted for a hydroxy group bonded to a photocurable isosorbide compound and used as a dental filler, the damage caused by contact with water is reduced to provide an isosorbide derivative compound having improved mechanical strength have.

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,

n is independently 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.

The n may independently 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]

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

[Reaction Scheme 1]

In the above Reaction Scheme 1,

n is independently 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 carried out at -10 to 50 < 0 > C.

In the step (a), an esterification reaction may be carried out.

In said step (a), a nucleophilic catalyst and a coupling agent may be further included.

Wherein the nucleophilic catalyst is selected from the group consisting of dimethylaminopyridine, 4- (1-pyrrolidinyl) pyridine, 2-halopyridinium salts and 1-tosylimidazole. And may include at least one selected.

Wherein the coupling agent is N, N'-dicyclohexylcarbodiimide, TBTU (2- (1H-benzotriazole-1-yl) -1,1,3,3-tetramethyluronium tetrafluoroborate) TATU (2- (1H-7-azabenzotriazole-1-yl) -1,1,3,3-tetramethyluronium tetrafluoroborate), and COMU (1 - [(1- (cyano-2-ethoxy-2-oxoethylideneamiooxy) dimethylaminomorpholino methylene )] methanaminium hexafluorophosphate.

Wherein the compound 2 is selected from the group consisting of 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, and 2 Hydroxypropyl acrylate, and 2-hydroxypropyl acrylate.

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

The isosorbide derivative compound; And initiators; . ≪ / RTI >

100 parts by weight of the isosorbide derivative; And 0.1 to 5 parts by weight of the initiator; . ≪ / 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.

The present invention eliminates the methacrylate group in place of the hydroxy group bonded to the isosorbide derivative compound and removes the methacrylate group. When this is applied to a dental filler, the damage due to contact with water is reduced, and mechanical properties such as compressive strength and flexural strength .

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

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.

As used herein, unless otherwise defined, the term "alkyl group" means an aliphatic hydrocarbon group.

The alkyl group may be a " saturated alkyl group " which does not contain any double or triple bonds.

The alkyl group may be an " unsaturated alkyl group " comprising at least one double bond or triple bond.

The alkyl group, whether saturated or unsaturated, can be branched, straight chain or cyclic.

The alkyl group may be a C1 to C30 alkyl group. More specifically, a C1 to C20 alkyl group, a C1 to C10 alkyl group, or a C1 to C6 alkyl group.

For example, the C1 to C4 alkyl groups may have 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, Indicating that they are selected from the group.

Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, ethenyl group, Butyl group, cyclopentyl group, cyclohexyl group, and the like.

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,

n is independently 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, n is 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]

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

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,

n is independently any one of integers from 1 to 5; R ¹ is each independently 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, C10 aryl group.

First, Compound 1 is reacted with Compound 2 to obtain Compound 3 Isosobaid  A derivative compound is prepared (step a).

The step (a) may be carried out at -10 to 50 < 0 > C. 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.

In the step (a), an esterification reaction may be carried out.

In said step (a), a nucleophilic catalyst and a coupling agent may be further included.

Wherein the nucleophilic catalyst is selected from the group consisting of dimethylaminopyridine, 4- (1-pyrrolidinyl) pyridine, 2-halopyridinium salts and 1-tosylimidazole. And may include one or more selected from the group consisting of dimethylaminopyridine, preferably dimethylaminopyridine.

Wherein the coupling agent is N, N'-dicyclohexylcarbodiimide, TBTU (2- (1H-benzotriazole-1-yl) -1,1,3,3-tetramethyluronium tetrafluoroborate) TATU (2- (1H-7-azabenzotriazole-1-yl) -1,1,3,3-tetramethyluronium tetrafluoroborate), and COMU (1 - [(1- (cyano-2-ethoxy-2-oxoethylideneamiooxy) dimethylaminomorpholino methylene )] methanaminium hexafluorophosphate, and may include at least one selected from N, N'-dicyclohexylcarbodiimide.

The esterification reaction is an esterification reaction using dicyclohexylcarbodiimide (DCC) as a coupling agent in the Steglich esterification reaction and dimethylaminopyridine (DMAP) as a catalyst.

Wherein the compound 2 is selected from the group consisting of 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, and 2 Hydroxypropyl acrylate, and 2-hydroxypropyl acrylate.

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; And initiators; , Preferably 100 parts by weight of the isosorbide derivative compound represented by Structural Formula 1; And 0.1 to 5 parts by weight of the initiator; . ≪ / 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.

[Example]

Preparation Example 1: Preparation of an isosorbide derivative containing a carboxyl group at the terminal

3.65 g (25 mmol, 1 equiv) of isosorbide and 5.76 g (58 mmol, 1.15 equiv) of succinic anhydride were added and stirred at 120 ° C for 24 hours. After filtration, the material was subjected to an aqueous solution of methylene chloride (MC) and sodium chloride (NaCl) to separate an organic layer containing methylene chloride.

The separated organic layer was subjected to rotary distillation to remove methylene chloride, and the resulting material was subjected to column chromatography to obtain an isosorbide derivative (IS-COOH) using a solvent (Ethyl acetate).

The reaction of Preparation Example 1 is shown in Reaction Scheme 2 shown below.

[Reaction Scheme 2]

Example 1: Isosorbide derivative compound (IS-SC-MA)

20.0 g (1 eq) of an isosorbide derivative containing a carboxyl group at the terminal and 50 mL of ethyl acetate (EA) prepared according to Preparation Example 1 were placed and an N, N'-dicyclohexyl 28.61 ml (138.7 mmol) of N, N'-dicyclohexylcarbodiimide (DCC) was added dropwise as a coupling agent for 30 minutes and 11.01 ml (90.15 mmol) of dimethylaminopyridine (DMAP) It was dripped for an hour. Then, 16.62 g (138.69 mmol) of 2-hydroxyethyl methacrylate (HDEMA) was added, and the mixture was reacted at room temperature for 24 hours with stirring.

After filtration, the material was subjected to an aqueous solution of methylene chloride (MC) and sodium chloride (NaCl) to separate an organic layer containing methylene chloride.

The separated organic layer was washed with a rotary evaporator to remove methylene chloride and the resulting material was purified by column chromatography using an isosorbide derivative (IS-SC-MA) using a hexane (ethyl acetate = 1: 1) ≪ / RTI >

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

The reaction of Example 1 is as shown in Scheme 3 below.

[Reaction Scheme 3]

¹ H NMR analysis of the isosorbide derivative (IS-SC-MA) is shown in FIG. 1, and ¹ H NMR data thereof is as follows.

_{^{1 H NMR (CDCl 3, 300MHz}} ): δ 6.21-6.11 (s, 2H), 5.70-5.60 (s, 2H), 5.30-5.10 (m, 2H), 4.90-4.80 (t, 1H), 4.55-3.45 (m, 3H), 3.85-3.75 (m, 1H), 2.80-2.60 (m, 8H), 2.00-1.90 (s, 6H) .

Example 2: Composition comprising isosorbide derivative compound (IS-SC-MA)

1 wt% of an initiator composed of camphoquinone / ethyl-4-dimethylamino benzoate (1: 2) was added to the compound prepared according to Example 1 and mixed three times for 3 minutes at 2000 rpm using a planetary vacuum mixer to obtain a composition .

Comparative Example 1: Preparation of IsoGMA Compound

(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. A round bottom flask containing the reaction solution was immersed in a 40 ° C bath 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 DEG C 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. The reaction mixture was washed with distilled water and brine in this order. The organic layer was washed with water (MgSO ₄ ), filtered and concentrated under reduced pressure. Flash chromatography (hexane: ethyl acetate = 1: 1) The resulting compound (a) was obtained (1.1 g, 4.3 mmole, 63%).

The reaction of Step 1 is shown in Scheme 4 shown below.

[Reaction Scheme 4]

(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. Thereafter, 3 drops of tetraethylamine (TEA) was added dropwise, and the mixture was stirred at 100 占 폚 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 2: IsoGMA composition

1 wt% of an initiator composed of camphoquinone / ethyl-4-dimethylamino benzoate (1: 2) was added to the IsoGMA compound prepared according to Comparative Example 1 and mixed three times for 3 minutes at 2000 rpm using a planetary vacuum mixer. A composition was prepared.

(2)

Comparative Example  3: BisGMA / TEGDMA  compound

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

(3)

[Chemical Formula 4]

Comparative Example  4: BisGMA / TEGDMA  Composition

1 wt% initiator composed of camphoquinone / ethyl-4-dimethylamino benzoate (1: 2) was added to the BisGMA / TEGDMA compound prepared according to Comparative Example 3 and mixed three times for 3 minutes at 2000 rpm using a planetary vacuum mixer A BisGMA / TEGDMA composition of Example 4 was prepared.

[Test Example]

Test Example  1: Compressive Strength and Flexural Strength Analysis

FIG. 2 shows the compressive strength of the composition prepared according to Example 2 and Comparative Examples 2 and 4, and FIG. 3 shows the results of measurement of the flexural strength of the composition prepared according to Example 2 and Comparative Examples 2 and 4.

Specimens for measuring the compressive strength were prepared by filling a cylindrical (Φ x L = 4 x 6 mm) SUS mold with a 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 compositions prepared according to Example 2 were found to be similar to those of the compositions prepared according to Comparative Example 2 and Comparative Example 4.

Test Example 2: Shrinkage resin compare analysis

Fig. 4 shows the results of the resin shrinkage analysis of the compositions prepared according to Example 2 and Comparative Examples 2 and 4. 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 composition prepared in Example 2 was lower than that of the composition prepared in Comparative Example 2 and Comparative Example 4.

Therefore, the composition prepared according to Example 2 has a relatively low hardening shrinkage ratio as compared with the composition prepared according to Comparative Example 2 and Comparative Example 4, and it is analyzed that the dimensional stability is high, and the peeling problem in adhesion can be improved.

Test Example 3: Water Sorption Analysis

5 shows the results of water absorption analysis of the compositions prepared according to Example 2 and Comparative Examples 2 and 4. FIG.

Measurement specimens for measuring water absorption were prepared by filling a prepared resin mixture with a cylindrical SUS mold (Φ x L = 15 × 1 mm) and using a 3M ESPE Elipar ^™ 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.

According to FIG. 5, the composition prepared according to Example 2 showed lower water absorption than the composition prepared according to Comparative Example 2 and Comparative Example 4, and the physical properties were improved.

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 (16)

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

In formula 1,
n is independently 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 method according to claim 1,
Wherein each of R < ¹ > is independently a methyl group. The method according to claim 1,
Wherein each of n is independently any one of integers from 1 to 3. < RTI ID = 0.0 > 11. < / RTI > 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 with Compound 2 to prepare an isosorbide derivative represented by Compound 3; To
≪ / RTI >
[Reaction Scheme 1]

In the above Reaction Scheme 1,
n is independently 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. 6. The method of claim 5,
Wherein said step (a) is carried out at a temperature of from -10 to < RTI ID = 0.0 > 50 C. < / RTI > 6. The method of claim 5,
Wherein the step (a) is carried out by an esterification reaction. 6. The method of claim 5,
In the step (a)
A nucleophilic catalyst, and a coupling agent. ≪ RTI ID = 0.0 > 11. < / RTI > 9. The method of claim 8,
Wherein the nucleophilic catalyst is selected from the group consisting of dimethylaminopyridine, 4- (1-pyrrolidinyl) pyridine, 2-halopyridinium salts and 1-tosylimidazole. Wherein the at least one isosorbide derivative is at least one compound selected from the group consisting of a compound represented by formula 9. The method of claim 8,
Wherein the coupling agent is N, N'-dicyclohexylcarbodiimide, TBTU (2- (1H-benzotriazole-1-yl) -1,1,3,3-tetramethyluronium tetrafluoroborate) TATU (2- (1H-7-azabenzotriazole-1-yl) -1,1,3,3-tetramethyluronium tetrafluoroborate), and COMU (1 - [(1- (cyano-2-ethoxy-2-oxoethylideneamiooxy) dimethylaminomorpholino methylene )] methanaminium hexafluorophosphate. The method for producing an isosorbide derivative compound according to claim 1, 6. The method of claim 5,
Wherein the compound 2 is selected from the group consisting of 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, and 2 (2-hydroxypropyl acrylate). The method for producing an isosorbide derivative according to claim 1, A dental material composition comprising the isosorbide derivative of claim 1. 13. The method of claim 12,
An isosorbide derivative compound of claim 1; And
Initiator; To
0.0 > dental < / RTI > 14. The method of claim 13,
100 parts by weight of the isosorbide derivative compound of claim 1; And
0.1 to 5 parts by weight of the initiator; To
Dental material composition. 14. The method of claim 13,
Wherein the initiator is a photopolymerization initiator. 14. The method of claim 13,
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-trimethylbenzylphenylphosphinate, and the like.

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