Silyl ether isohexide-based organic compounds, their preparation method and curable compositions containing the same

Abstract

To provide isohexide-based plastics that can be applied in the field of high-tech materials such as displays and semiconductors.SOLUTION: The present invention provides an organic-inorganic compound including a first structural body and a curable reactive group, wherein the first structural body has a structure in which silane and isohexide are chemically bonded through a silyl ether bond. There is also provided a curable composition containing the same.SELECTED DRAWING: Figure 3

Description

[Technical field]

[0001] The present invention relates to curable reactors and isohexide-based organic compounds containing silyl ether linkages, methods for their preparation, and curable compositions containing the same. [Background technology]

[0002] As the demand for low-carbon and environmentally friendly materials to respond to climate change and achieve sustainable growth increases, active efforts are being made to replace conventional petroleum-based plastics with bio-based plastics. In particular, isohexide is a 100% natural biomaterial made from corn, sugar, wheat, and potatoes, and is non-toxic and has similar mechanical properties to conventional petrochemical-based bisphenol compounds, so isohexide-based plastics using isohexide are attracting much attention. However, while the currently realized isohexide-based plastics meet the demand for low-carbon and environmental friendliness, they do not have revolutionary properties compared to conventional petrochemical-based plastics, and there is a problem that they are difficult to apply to advanced material fields such as displays and semiconductors. Summary of the Invention [Problem to be solved by the invention]

[0003] One technical problem to be solved by the present invention is to provide an isohexide-based organic compound having a curable reactive group and a silyl ether bond, and a curable composition containing the same.

[0004] One technical problem to be solved by the present invention is to provide a method for preparing an isohexide-based organic or inorganic compound having a curable reactive group and a silyl ether bond.

[0005] The problems to be solved by the present invention are not limited to those mentioned above, and other problems not mentioned will be clearly understood by those skilled in the art from the following description. [Means for solving the problem]

[0006] The organic / inorganic compound according to an embodiment of the present invention includes a first structure and a curable reactive group, and the first structure has a structure in which a silane and an isohexide are chemically bonded via a silyl ether bond.

[0007] The organic / inorganic compound according to an embodiment of the present invention satisfies the following Chemical Formula 1. [ka]

[0008] In the above chemical formula, a, b, and c are 0 or a positive number, and d and e are positive numbers; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 each independently represents a curable reactive group, C1 to C 20 an alkyl group having a carbon number of from C3 to C8, a cycloalkyl group having a carbon number of from C6 to C 20 wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 At least one of the groups contains a curable reactive group.

[0009] The organic / inorganic compound according to an embodiment of the present invention includes a siloxane group bonded to the silyl ether group. In the organic / inorganic compound according to an embodiment of the present invention, 0.1≦a+b+c≦0.9, 0≦d≦0.3, 0.1≦e≦0.9, and a+b+c+d+e=1. According to an embodiment of the present invention, the curable reactive group is selected from the group consisting of an epoxy group, an amine group, an acryl group, a methacryl group, a mercapto group, a carboxyl group, a vinyl group, a nitro group, a sulfone group, a hydroxyl group, a urethane group, a ureido group, an isocyanate group, an oxetane group, or a combination thereof.

[0010] According to one embodiment of the present invention, the isohexide includes at least one of isosorbide, isomannide, isoidide, and combinations thereof.

[0011] The organic / inorganic compound according to an embodiment of the present invention satisfies the following Chemical Formula 2. [ka]

[0012] In the above formula 2, x includes the curable reactive group and the carbon compound, and n is a positive number.

[0013] A method for producing an organic or inorganic compound according to an embodiment of the present invention includes preparing a silane compound, preparing an isohexide, and reacting the silane compound with the isohexide, whereby a silyl ether bond is formed by reacting the silane compound with the isohexide.

[0014] According to an embodiment of the present invention, the silane compound is selected from the group consisting of the following formulas 4 to 7, or a combination thereof.

[0015] [Chemical formula 4] R 1 Si(OR I )3 [Chemical formula 5] R 2 R 3 Si(OR II )2 [Chemical formula 6] R 4 R 5 R 6 Si(OR III ) [Chemical formula 7] Si(OR IV )4

[0016] R 1 , R 2 , R 3 , R 4 , R 5 , and R 6each independently represents a curable reactive group, C1 to C 20 an alkyl group having a carbon number of from C3 to C8, a cycloalkyl group having a carbon number of from C6 to C 20 and selected from the group consisting of aryl groups R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 At least one of the groups contains a curable reactive group; R I , R II , R III , R IV each independently includes hydrogen, a linear C1 to C6 alkyl group, or a branched C1 to C6 alkyl group.

[0017] According to one embodiment of the present invention, the molar ratio of the silane compounds of Formulas 4, 5, and 6 to the total reactants is defined as f, the molar ratio of the silane compound of Formula 7 to the total reactants is defined as g, and the molar ratio of the isohexide to the total reactants is defined as h, where 0.1≦f≦0.9, 0≦g≦0.3, 0.1≦h≦0.9, and f+g+h=1.

[0018] The method for preparing an organic / inorganic compound according to an embodiment of the present invention further includes forming a siloxane bond.

[0019] In the method for preparing an organic / inorganic compound according to an embodiment of the present invention, forming the siloxane bond includes performing at least one of a hydration reaction and a condensation reaction between the silane compounds.

[0020] In one embodiment of the present invention, the method for preparing an organic or inorganic compound further includes reacting the silane compound with the isohexide and using a catalyst to promote the formation of the siloxane bond, the catalyst being one of the group consisting of acid catalysts such as acetic acid, hydrochloric acid, hydrogen fluoride, sulfuric acid, nitric acid, chlorosulfonic acid, iodic acid, pyrophosphoric acid, etc., basic catalysts such as potassium hydroxide, sodium hydroxide, barium hydroxide, imidazole, ion exchange resins, water, and combinations thereof.

[0021] In the method for preparing an organic or inorganic compound according to an embodiment of the present invention, the curable reactive group contained in the silane compound is an epoxy group and / or an oxetane group.

[0022] In the method for producing an organic or inorganic compound according to an embodiment of the present invention, the silane compound may be 5,6-epoxyhexyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, 3-ethyl-3-[[3-triethoxysilyl)propoxy] methyl]oxetane, 7-trimethoxysilyl-4-thiaheptanoic acid-(3-ethyl-oxetan-3-yl)methyl ester, N-(3-triethoxysilylpropyl)-(3-ethyloxetan-3-yl)-methylcarbamic acid, 2-(3-triethoxysilylpropylthio)succinic acid-bis-[3-ethyloxetan-3-yl)-methyl] ester, (3,4-ethoxycyclohexyl)ethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl(methyl)dimethoxysilane, (3,4-epoxycyclohexyl)ethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl(methyl)diethoxysilane, (2-(7-oxabicyclo[4,1,0]heptan-3-yl)ethyl)(methyl)silanediol, dimethoxy(methyl)(3-(oxiran-2-yl)propyl)silane, diethoxy(methyl)(3-(oxiran-2-yl)propyl)silane, methyl(3-(oxir-2-yl)propyl)silanediol, (3-glycidoxypropyl)dimethoxymethylsilane, (3-glycidoxypropyl)diethoxymethylsilane, (3-glycidoxypropyl)methylsilanediol, (3-glycidoxypropyl)dimethylethoxysilane, and 3-glycidoxypropyldimethylmethoxysilane.

[0023] In the method for preparing an organic / inorganic compound according to an embodiment of the present invention, the curable reactive group contained in the silane compound includes at least one of an amine group, a ureido group, an isocyanate group, and a mercapto group.

[0024] In the method for producing an organic or inorganic compound according to an embodiment of the present invention, the silane compound may be 4-aminobutyltriethoxysilane, 4-amino-3,3-dimethylbutyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-(6-aminohexyl)aminomethyltriethoxysilane, N-(6-aminohexyl)aminopropyltrimethoxysilane, n-(2-aminoethyl)-11-aminoundecyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropylsilanetriol, 3- ... Methoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3 dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N-(vinylbenzyl)-2-aminoethyl 3-aminopropyltrimethoxysilane hydrochloride, 3-(m-aminophenoxy)propyltrimethoxysilane, m-aminophenyltrimethoxysilane, p-aminophenyltrimethoxysilane, aminophenyltrimethoxysilane, 3-aminopropyltris(methoxyethoxyethoxy)silane, 11-Aminoundecyltriethoxysilane, 2-(4-pyridylethyl)triethoxysilane, 2-(2-pyridylethyl)trimethoxysilane, N-(3-trimethoxysilanepropyl)pyrrole, 3-aminopropylsilanetriol, (aminoethylaminomethyl)phenethyltrimethoxysilane, 3-ureidopropyltrialkoxysilane, 3-isocyanatopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl) -3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminoisobutylmethyldimethoxysilane, 4-amino-3,3-dimethylbutylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 1-amino-2-(dimethylethoxysilyl)propane, 3-aminopropyldiisopropylethoxysilane, 3-aminopropyldimethylethoxysilane, and N-(2-aminoethyl)-3-aminoisobutyldimethylmethoxysilane.

[0025] A curable composition according to an embodiment of the present invention includes an organic / inorganic compound including a first structure and a curable reactive group, and a curing agent, the first structure having a structure in which a silane and an isohexide are chemically bonded via a silyl ether bond, and the curable reactive group is any one of an epoxy group, an oxetane group, or a combination thereof.

[0026] The curable composition according to an embodiment of the present invention further includes an initiator, a reactive diluent, and an additive. The curing agent is any one of a silyl ether isohexide-based organic compound having an amine group, a ureido group, an isocyanate group, or a mercapto group as a curable reactive group, an acid anhydride-based curing agent, an amine-based curing agent, an imidazole-based curing agent, a carboxylic acid-based curing agent, a phosphine-based curing agent, an iodine derivative-based curing agent, and a combination thereof. The initiator is any one of a photoacid generator, a photosalt generator, a thermal acid generator, and a combination thereof. The reactive diluent is any one of an epoxy reactive diluent, an oxetane reactive diluent, a polyethylene glycol, and a combination thereof. The additive is any one of graphene, carbon nanotubes, fullerene, hexagonal boron nitride, boron nitride nanotubes, alumina, maxine, and a combination thereof. Effect of the Invention

[0027] The isohexide-based compound having a silyl ether bond according to the present invention provides a low carbon, environmentally friendly bioplastic solution by having a silyl ether bond, and also has improved heat resistance and thermomechanical properties, thereby realizing superior heat resistance and thermomechanical properties compared to conventional petrochemical-based epoxies.

[0028] Ultimately, the isohexide-based compounds having silyl ether bonds of the present invention can be used in advanced materials fields such as displays, semiconductors, automobiles, aviation, and robotics. [Brief description of the drawings]

[0029] [Figure 1] 1 is a graph illustrating a conventional isohexide-based epoxy resin. [Diagram 2] 1 is a graph illustrating a conventional isohexide-based epoxy resin. [Diagram 3] 1 is a graph illustrating an isohexide-based compound according to an embodiment of the present invention. [Figure 4] 1 is a graph illustrating an isohexide-based compound according to an embodiment of the present invention. [Diagram 5] 1 is a graph illustrating an isohexide-based compound according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0030] The advantages and features of the present invention, and the methods for achieving them, will become clear from the detailed description of the embodiments with accompanying drawings. However, the present invention is not limited to the embodiments disclosed below, and may be embodied in various different forms. However, the embodiments are provided to make the disclosure of the present invention complete, and to fully inform those skilled in the art of the present invention of the scope of the invention, and the present invention is only defined by the scope of the claims. Throughout the specification, the same reference numerals refer to the same elements.

[0031] The terms used in the present specification are for the purpose of describing the embodiments and are not intended to limit the present invention. In the present specification, the singular form includes the plural form unless otherwise specified in the context of the text. As used in the specification, the words "comprises" and / or "comprising" do not exclude the presence or addition of one or more other components, steps, operations, and / or elements to a referenced component, step, operation, and / or element.

[0032] In addition, the embodiments described in this specification are described with reference to cross-sectional views and / or plan views which are ideal exemplary views of the present invention. In the drawings, the thicknesses of films and regions are exaggerated for the effective explanation of the technical contents. Therefore, the shapes of the exemplary views may be changed depending on the manufacturing technology and / or tolerances. Therefore, the embodiments of the present invention are not limited to the specific shapes shown in the drawings, but also include changes in shapes generated by the manufacturing process. Therefore, the regions illustrated in the drawings have schematic attributes, and the patterns of the regions illustrated in the drawings are intended to illustrate specific shapes of the regions of the device and are not intended to limit the scope of the invention.

[0033] Terms used in the embodiments of the present invention are to be interpreted in the manner commonly known to those of ordinary skill in the art unless otherwise defined.

[0034] Figures 1 and 2 are example graphs comparing the properties of conventional petrochemical-based plastics and bioplastics.

[0035] Among conventional petrochemical-based plastics, bisphenol resins in particular have excellent strength and heat resistance and are used in many fields, but there is an increasing demand for environmentally friendly bioplastics due to concerns that they may cause endocrine disruption. Also, in order to comply with low-carbon policies such as the Carbon Border Adjustment System for carbon neutrality, there is an increasing need to replace conventional petrochemical-based plastics with bioplastics, and isohexide-based bioplastics are emerging as an alternative as part of this effort.

[0036] Isohexide-based bioplastics include isohexide-based epoxy resins based on isohexides derived from corn starch.

[0037] Referring to FIG. 1, the properties of a petrochemical-based plastic, bisphenol epoxy resin (DGEBA) and an amine toughening agent (DETA), and an isohexide-based plastic, isosorbide-based epoxy resin (DGEI) and an isosorbide-based amine toughening agent (ISODA), are shown.

[0038] The graph in Figure 1 is a graph showing the results of dynamic mechanical analysis (DMA) of DGEBA / DETA (diglycidyl ether of bisphenol A / diethylenetriamine), DGEBA / ISODA (diglycidyl ether of bisphenol A / isosorbide diamine), DGEI / ISODA (diglycidyl ether of isosorbide / isosorbide diamine), and DGEI / DETA (diglycidyl ether of isosorbide / diethylenetriamine). The y-axis of the graph in Figure 1 is storage modulus (MPa) and the x-axis is temperature (°C). Referring to Figure 1, the elastic modulus of DGEBA / ISODA, DGEI / DETA, and DGEI / ISODA containing isohexide-based plastics drops sharply at temperatures significantly lower than that of DGEBA / DETA.

[0039] Referring to Figure 2, the properties of a petrochemical-based plastic, bisphenol epoxy resin (DGEBA) and an amine toughening agent (DETA), and an isohexide-based plastic, isosorbide-based epoxy resin (DGEI) and an isosorbide-based amine toughening agent (ISODA), are shown. The graph in Figure 2 shows the results of thermogravimetric analysis (TGA) of DGEBA / DETA, DGEBA / ISODA, DGEI / ISODA, and DGEI / DETA.

[0040] Referring to the graph in FIG. 2, the weight percent pyrolyzed by temperature is shown.

[0041] The y-axis of Figure 2 is weight (%) and the x-axis is temperature (°C). The temperature at which 5% by weight pyrolysis occurs is the highest for DGEBA / DETA, a petrochemical-based plastic, followed by DGEI / DETA, DGEBA / ISODA, and DGEI / ISODA, which contain isohexide-based plastics, in that order.

[0042] Referring to Figures 1 and 2, the thermal and physical properties of conventional petrochemical-based plastics are superior to conventional bioplastics.

[0043] The organic / inorganic compounds according to the present invention are silyl ether isohexide-based organic / inorganic compounds.

[0044] The organic / inorganic compound according to the present invention contains a molecular structure derived from an isohexide having a silyl ether group and a curable reactive group. The organic / inorganic compound according to the present invention satisfies the following Chemical Formula 1. Chemical Formula 1 is an average unit chemical formula. [ka]

[0045] In the above formula, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 each independently represents a curable reactive group, C1 to C 20 an alkyl group having a carbon number of from C3 to C8, a cycloalkyl group having a carbon number of from C6 to C 20 wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 At least one of the groups contains a curable reactive group.

[0046] The curable reactive groups are selected from the group consisting of epoxy groups, amine groups, acrylic groups, methacrylic groups, mercapto groups, carboxyl groups, vinyl groups, nitro groups, sulfone groups, hydroxyl groups, urethane groups, oxetane groups, and combinations thereof.

[0047] In the formula 1, b and c are each 0 or a positive number, and 0.1≦a+b+c≦0.9, 0≦d≦0.3, 0.1≦e≦0.9, and a+b+c+d+e=1. If a+b+c is less than 0.1, the amount of silane compounds capable of forming silyl ether bonds with isohexides is relatively small, so that synthesis may not be possible. If it is more than 0.9, the amount of biocarbon derived from isohexides is low, so that it may be difficult to comply with environmentally friendly policies. If d is more than 0.3, the chemical reaction may be excessive, causing gelation. If e is less than 0.1, the amount of biocarbon derived from isohexides is low, so that it may be difficult to comply with environmentally friendly policies. If it is more than 0.9, the amount of silane compounds capable of forming silyl ether bonds with isohexides is relatively small, so that synthesis may not be possible.

[0048] According to one embodiment of the present invention, the isohexide-based organic compound is represented by the formula 1, 1 SiO 3 / 2 ) units, (R 2 R 3 SiO 2 / 2 ) units, (R 4 R 5 R 6 SiO 1 / 2 ) units, (SiO 4 / 2 For example, an organic compound with or without an isohexide base has three (R 1 SiO 3 / 2 ) units, two (R 2 R 3 SiO 2 / 2 ) unit, one (R 4 R 5 R 6 SiO 1 / 2 ) unit, one (SiO 4 / 2) units, it is represented by the average unit chemical formula Z below. [ka]

[0049] In the above chemical formula Z, R 1a , R 1b , R 1c R 1 ai, aii, and aiii are each 0 or a positive number, the sum is a defined in Formula 1, and R 2a , R 2b R 2 As defined in R 3a , R 3b R 3 where bi and bii are each 0 or a positive number, and the sum is b defined in Formula 1; R 1a , R 1b , R 1c , R 2a , R 2b , R 3a , R 3b , R 4 , R 5 , R 6 At least one of the groups contains a curable reactive group.

[0050] The isohexide includes at least one of isosorbide, isomannide, isoidide, and combinations thereof.

[0051] The isohexide-based organic or inorganic compound according to the present invention may contain an intramolecular silyl ether bond and may further contain a siloxane bond, thereby realizing superior thermal and mechanical properties compared to conventional isohexide-based organic or inorganic compounds. In this case, the organic or inorganic compound satisfies the following formula 2. As part of the molecular structure in one embodiment, the silyl ether bond and the siloxane bond respectively represent a Si-OC bond and a Si-O-Si bond as shown in formula 2 below. [ka]

[0052] In the above formula 2, x includes the curable reactive group and the carbon compound, and n is a positive number.

[0053] The X satisfies the following formula 3.

[0054] [Chemical formula 3] (R 1 SiO 3 / 2 ) a (R 2 R 3 SiO 2 / 2 ) b (R 4 R 5 R 6 SiO 1 / 2 ) c (SiO 4 / 2 ) d

[0055] In this case, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 each independently represents a curable reactive group, C1 to C 20 an alkyl group having a carbon number of from C3 to C8, a cycloalkyl group having a carbon number of from C6 to C 20 wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 At least one of the groups a, b, c, and d contains a curable reactive group, and a, b, c, and d are positive numbers, where 0.1≦a+b+c≦0.9 and 0≦d≦0.3.

[0056] A method for producing an organic or inorganic compound according to an embodiment of the present invention includes preparing a silane compound, preparing an isohexide, and reacting the silane compound with the isohexide, whereby a silyl ether bond is formed by reacting the silane compound with the isohexide.

[0057] Reacting the silane compound with an isohexide involves forming a silyl ether bond through a condensation reaction.

[0058] The silane compound is selected from the group consisting of the following formulas 4 to 7, or a combination thereof.

[0059] [Chemical formula 4] R 1 Si(OR I )3 [Chemical formula 5] R 2 R 3 Si(OR II )2 [Chemical formula 6] R 4 R 5 R 6 Si(OR III ) [Chemical formula 7] Si(OR IV )4

[0060] R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 each independently represents a curable reactive group, C1 to C 20 an alkyl group having a carbon number of from C3 to C8, a cycloalkyl group having a carbon number of from C6 to C 20 wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 At least one of R I , R II , R III , R IV each independently includes hydrogen, a linear C1 to C6 alkyl group, or a branched C1 to C6 alkyl group.

[0061] Isohexide includes three isomeric forms: isomannide, isosorbide, and isoidide.

[0062] The molar ratio of silanes represented by formulas 4, 5 and 6 to the total reactants is in the range of 0.1 to 0.9, the molar ratio of silane represented by formula 7 to the total reactants is in the range of 0 to 0.3, and the molar ratio of isohexide to the total reactants is in the range of 0.1 to 0.9.

[0063] That is, the molar ratio of the silane compounds of the formulas 4, 5, and 6 to the total reactants is defined as f, the molar ratio of the silane compound of the formula 7 to the total reactants is g, and the molar ratio of the isohexide to the total reactants is h, where 0.1≦f≦0.9, 0≦g≦0.3, and 0.1≦h≦0.9, and f+g+h=1. If f is less than 0.1, the amount of silane compounds capable of forming a silyl ether bond with the isohexide is relatively small, so that synthesis may not be possible, and if it is 0.9 or more, the content of biocarbon derived from the isohexide is low, so that it may be difficult to comply with environmentally friendly policies. If g is 0.3 or more, the chemical reaction may be excessively carried out, so that gelation may occur. If h is 0.1 or less, the content of biocarbon derived from the isohexide is low, so that it may be difficult to comply with environmentally friendly policies, and if it is 0.9 or more, the amount of silane compounds capable of forming a silyl ether bond with the isohexide is relatively small, so that synthesis may not be possible. According to an embodiment of the present invention, the isohexide-based organic compound is prepared by independently containing a plurality of compounds represented by the formulas 4, 5, 6, and 7 and isohexide. For example, the isohexide-based organic compound is prepared by independently containing three kinds of silanes [R 1a Si(OR Ia )3, R 1b Si(OR Ib )3, R 1c Si(OR Ic )3], and two types of silanes represented by chemical formula 5 [R 2a R 3a Si(OR IIa )2, R 2b R 3b Si(OR IIb )2], and one type of silane represented by formula 6 [R 4 R 5 R 6SiOR III ], one type of silane [Si(OR IV )4], which is produced by the condensation reaction of two isohexides [isomannide and isosorbide]. 1a , R 1b , R 1c are R in chemical formula 4 1 As defined in R Ia , R Ib , R Ic are R in chemical formula 4 I As defined in R 2a , R 2b are R in Chemical Formula 5 2 As defined in R 3a , R 3b are R in chemical formula 6 3 As defined in R IIa , R IIb are R in chemical formula 7 II As defined in.

[0064] According to an embodiment of the present invention, the curable reactive group is selected from the group consisting of an epoxy group, an amine group, an acryl group, a methacryl group, a mercapto group, a carboxyl group, a vinyl group, a nitro group, a sulfone group, a hydroxyl group, a urethane group, a ureido group, an isocyanate group, an oxetane group, or a combination thereof. Among the curable reactive groups, the epoxy group and the oxetane group are preferred for use in the adhesive material field in the semiconductor and display fields, and the epoxy group includes a glycidyl epoxy group and an alicyclic epoxy group.

[0065] The silyl ether isohexide-based organic compound having an epoxy group and / or an oxetane group as the curable reactive group is prepared by using a silane compound having an epoxy group and / or an oxetane group. In particular, the silane compound having an epoxy group and / or an oxetane group and represented by the formula 4 is selected from 5,6-epoxyhexyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, 3-ethyl-3-[[3-triethoxysilyl)propoxy]methyl]oxetane, 7-trimethoxysilyl-4-thiaheptanoic acid-(3-ethyl-oxetan-3-yl)methyl ester, N-(3-triethoxysilylpropyl)-(3-ethyloxetan-3-yl)-methylcarbamic acid, and 2-(3-triethoxysilylpropylthio)succinic acid-bis-[3-ethyloxetan-3-yl)-methyl]ester. In particular, the silane compounds having an epoxy group and / or an oxetane group and corresponding to the above-mentioned chemical formula 5 are (3,4-ethoxycyclohexyl)ethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl(methyl)dimethoxysilane, (3,4-epoxycyclohexyl)ethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl(methyl)diethoxysilane, (2-(7-oxabicyclo[4,1,0]heptane) In one embodiment, the silanediol is selected from dimethoxy(methyl)(3-(oxiran-2-yl)propyl)silane, diethoxy(methyl)(3-(oxiran-2-yl)propyl)silane, methyl(3-(oxiran-2-yl)propyl)silanediol, (3-glycidoxypropyl)dimethoxymethylsilane, (3-glycidoxypropyl)diethoxymethylsilane, and (3-glycidoxypropyl)methylsilanediol.In particular, the silane compound having an epoxy group and / or an oxetane group and represented by formula 6 is selected from 3-(glycidoxypropyl)dimethylethoxysilane and 3-glycidoxypropyldimethylmethoxysilane. In one embodiment, the reaction of the silane compound with isohexide not only forms a silyl ether bond but also forms a siloxane bond. In this case, the isohexide-based organic or inorganic compound is prepared by forming a siloxane bond by a hydration reaction and / or a condensation reaction between the silane compounds represented by formulas 4, 5, 6, and 7. Water may be added to the reactants for the hydration reaction.

[0066] A catalyst is used to promote the condensation reaction of the silane compound with the isohexide, and the hydrolysis and / or condensation reaction between the silane compounds, and the catalyst is selected from an acid catalyst, a basic catalyst, an ion exchange resin, water, and combinations thereof.

[0067] Specifically, the catalyst is selected from the group consisting of acidic catalysts such as acetic acid, hydrochloric acid, hydrogen fluoride, sulfuric acid, nitric acid, chlorosulfonic acid, iodic acid, and pyrophosphoric acid; basic catalysts such as potassium hydroxide, sodium hydroxide, barium hydroxide, and imidazole; ion exchange resins, water, and combinations thereof.

[0068] The curable composition according to one embodiment of the present invention includes the silyl ether isohexide-based organic compound having an epoxy group and / or an oxetane group, and any one of a curing agent, an initiator, an additive, and a reactive diluent.

[0069] The curing agent is selected from silyl ether isohexide-based organic compounds having amine groups, and / or ureido groups, and / or isocyanate groups, and / or mercapto groups as curable reactive groups, acid anhydride-based curing agents, amine-based curing agents, imidazole-based curing agents, carboxylic acid-based curing agents, phosphine-based curing agents, iodine derivative-based curing agents, and combinations thereof.

[0070] The silyl ether isohexide-based organic or inorganic compound having an amine group, and / or a ureido group, and / or an isocyanate group, and / or a mercapto group as the curable reactive group satisfies Chemical Formula 1 above.

[0071] The silyl ether isohexide-based organic compound having an amine group, and / or a ureido group, and / or an isocyanate group, and / or a mercapto group as the curable reactive group is prepared by using a silane compound having an amine group, and / or a ureido group, and / or an isocyanate group, and / or a mercapto group. In detail, the silane compounds having an amine group, and / or a ureido group, and / or an isocyanate group, and / or a mercapto group, which correspond to the above-mentioned chemical formula 4, are 4-aminobutyltriethoxysilane, 4-amino-3,3-dimethylbutyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-(6-aminohexyl)aminomethyltriethoxysilane, N-(6-aminohexyl)aminopropyltrimethoxysilane, n-(2-aminoethyl)-11-aminoundecyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropylsilanetriol, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3dimethylbutylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, Methoxysilane, N-(vinylbenzyl)-2-aminoethyl 3-aminopropyl trimethoxysilane hydrochloride, 3-(m-aminophenoxy)propyl trimethoxysilane, m-aminophenyl trimethoxysilane, p-aminophenyl trimethoxysilane, aminophenyl trimethoxysilane, 3-aminopropyl tris(methoxyethoxyethoxy)silane, 11-aminoundecyl triethoxysilane, 2-(4-pyridylethyl)triethoxysilane, 2-(2-pyridylethyl)trimethoxysilane, N-(3-trimethoxysilanepropyl)pyrrole, 3-aminopropyl silanetriol, (aminoethylaminomethyl)phenethyl trimethoxysilane, 3-ureidopropyl trialkoxysilane, 3-isocyanatopropyl triethoxysilane, 3-mercaptopropyl trimethoxysilane.Specifically, the silane compound having an amine group, and / or a ureido group, and / or an isocyanate group, and / or a mercapto group, which corresponds to the above-mentioned chemical formula 5, is selected from N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminoisobutylmethyldimethoxysilane, 4-amino-3,3-dimethylbutylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, and 3-mercaptopropylmethyldimethoxysilane. Specifically, the silane compound having an amine group, and / or a ureido group, and / or an isocyanate group, and / or a mercapto group, which corresponds to the above-mentioned chemical formula 6, is selected from 1-amino-2-(dimethylethoxysilyl)propane, 3-aminopropyldiisopropylethoxysilane, 3-aminopropyldimethylethoxysilane, and N-(2-aminoethyl)-3-aminoisobutyldimethylmethoxysilane.

[0072] In particular, the acid anhydride curing agent is selected from phthalic anhydride, trimellitic anhydride, pyromellitic dianhydride, benzophenonetetracarboxylic dianhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride, methylendomethylenetetrahydrophthalic anhydride, methylbutenyltetrahydrophthalic anhydride, dodecenylsuccinic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, succinic anhydride, methylcyclohexenedicarboxylic anhydride, chlorendic anhydride, and combinations and chemical reactants thereof.

[0073] In particular, the amine-based curing agent is selected from diethylenetriamine, triethylenediamine, triethylenetetraamine, tetraethylenepentamine, diethylaminopropyleneamine, aminoethylpiperazine, menthanediamine, isoprenediamine, metaphenylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, 2-methyl-4-nitroaniline, dicyandiamide, triethylamine, benzyldimethylamine, methylbenzyldimethylamine, 2-(dimethylaminomethyl)phenol, 2,4,5-tris(dimethylaminomethyl)phenol, 1,8-diazabicyclo[5,4,0]undecene-7.1,5-diazabicyclo[4,3,0]non-5-ene, boron trichloride, boron trifluoride, and combinations and chemical reactants thereof.

[0074] Specifically, the imidazole-based curing agent is selected from 2-methylimidazole, 2-ethyl-4-methylimidazole, 2,4-dimethylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitic acid, epoxy imidazole adducts, microencapsulated latent curing agents having an imidazole core and a polymer-based surface coating, and combinations and chemical reactants thereof.

[0075] Specifically, the carboxylic acid hardener is selected from, but is not limited to, α-amino acids, β-amino acids, γ-amino acids, δ-amino acids, anthranilic acid, 3-aminobenzoic acid, para-aminobenzoic acid, and combinations thereof. Specifically, the reductive hardener is selected from, but is not limited to, glycine, alanine, valine, leucine, isoleucine, lysine, arginine, histidine, aspartic acid, asparagine, glutamine, phenylalanine, tyrosine, tryptophan, cysteine, methionine, serine, ornithine, 3-phenylserine, threonine, L-dopa, norleucine, phenylcylamine, sarcosine, proline, hydroxyproline, 3-hydroxyproline, 3,4-dihydroproline, pipecolic acid, β-alanine, 3-aminobenzoic acid, β ... Minobutyric acid, Isoserine, 3-Aminoisobutyric acid, 3-Amino-2-phenylpropionic acid, 3-Amino-5-methylhexanoic acid, 3-Amino-4-phenylbutyric acid, 3-Amino-4-hydroxybutyric acid, 3-Amino-4-hydroxypentanoic acid, 3-Amino-4-methylpentanoic acid, 3-Amino-3-phenylpropionic acid, Pyrrolidine-3-carboxylic acid, γ-aminobutyric acid, 4-Amino-3-hydroxybutyric acid, 3-Pyrrolidin-2-yl-propionic acid, 3-Aminocyclohexanecarboxyl Acid, 4-guanidinium butyric acid, 4-aminobenzoic acid, 3-aminobenzoic acid, 2-aminobenzoic acid, 3,5-diaminobenzoic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 3-aminoisonicotinic acid, 4-aminonicotinic acid, 5-aminonicotinic acid, 2-aminonicotinic acid, 6-aminonicotinic acid, 2-aminoisonicotinic acid, 6-aminopicolinic acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, capric acid, caprylic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid , oleic acid, linoleic acid, α-linolenic acid, cyclohexanecarboxylic acid, phenylacetic acid, benzoic acid, chlorobenzoic acid, bromobenzoic acid, nitrobenzoic acid, phthalic acid, isophthalic acid, terephthalic acid, salicylic acid, hydroxybenzoic acid, anthranilic acid, aminobenzoic acid, methoxybenzoic acid, glutaric acid, maleic acid, azelaic acid, abietic acid, adipic acid, ascorbic acid, acrylic acid, citric acid, and combinations and chemical reactants thereof.

[0076] The initiator is selected from a photoacid generator, a photosalt generator, a thermal acid generator, and combinations thereof. In particular, the initiator is selected from ytterbium trifluoromethenesulfonate, samarium trifluoromethenesulfonate, erbium trifluoromethenesulfonate, lanthanum trifluoromethenesulfonate, tetrabutylphosphonium methenesulfonate, ethylphenylphosphonium bromide salt, 3-methyl-2-butenyltetramethylenesulfonium hexafluoroantimonate, triarylsulfonium hexafluoroantimonate, triarylsulfonium hexafluorophosphate salt, 9-(4-hydroxyethoxyphenyl)cyansrenium hexafluorophosphate salt, 1-(3-methylbut-2-enyl)tetrahydro-1H-thiophenium hexafluoroantimonate, diphenyldiiodonium hexafluoroantimonate, diphenyldiiodonium hexafluorophosphate salt, ditolyliodonium hexafluorophosphate salt, triflate salt, and combinations and chemical reactants thereof.

[0077] The reactive diluent is selected from epoxy reactive diluents, oxetane reactive diluents, polyethylene glycol, and combinations thereof.

[0078] Specifically, the epoxy reactive diluent is selected from 2-ethylhexyl glycidyl ether, allyl glycidyl ether, polypropylene glycoglycidyl ether-H, polypropylene glycoglycidyl ether-S, n-butyl glycidyl ether, phenyl glycidyl ether, 4-vinylcyclohexene dioxide, cyclohexene vinyl monoxide, (3,4-epoxycyclohexyl)methyl 3,4-epoxycyclohexyl carboxylate, 3,4-epoxycyclohexylmethyl methacrylate, 3,4-epoxycyclohexane carboxylate, 2-(3,4-epoxycyclohexyl)-1,3-dioxolane, and bis(3,4-epoxycyclohexylmethyl)adipic acid, and combinations and chemical reactants thereof.

[0079] In particular, the oxetane reactive diluent is 3-methyloxetane, 2-methyloxetane, 3-oxetanol, 2-methyleneoxetane, 3-methyl-3-hydroxymethyloxetane, 3-ethyl-3-hydroxymethyloxetane, 3,3-oxetane dimethanethiol, 2-ethylhexyloxetane, 4-(3-methyloxetane-3-yl)benzonitrile, N-(2,2-dimethylpropyl)-3-methyl-3-oxetane Methanamine, N-(1,2-dimethylbutyl)-3-methyl-3-oxetanemethanamine, xylene bisoxetane, and 3-ethyl-3[{(3-ethyloxetan-3-yl)methoxy}methyl]oxetane, (3-ethyloxetan-3-yl)methyl(meth)acrylate, and 4-[(3-ethyloxetan-3-yl)methoxy]butan-1-ol, and combinations and chemical reactants thereof.

[0080] The additive is selected from graphene, carbon nanotubes, fullerenes, hexagonal boron nitride, boron nitride nanotubes, alumina, maxine, and combinations thereof.

[0081] 3 and 4 are graphs illustrating that the cured material containing an isohexide-based compound according to an embodiment of the present invention exhibits superior properties compared to cured materials containing conventional petrochemical-based compounds.

[0082] 3, the thermal decomposition characteristics of the cured material including the isohexide-based compound according to one embodiment of the present invention are shown. The characteristics of the cured material including the isohexide-based organic compound including silyl ether are indicated as "invention," and the characteristics of the cured material including the conventional petrochemical-based compound are indicated as "conventional."

[0083] The x-axis of Figure 3 is temperature (°C) and the y-axis is weight (%). The temperature at which 5% by weight of the cured material containing the isohexide-based organic or non-organic compound containing silyl ether of the present invention is thermally decomposed is 285°C, while the temperature at which 5% by weight of the cured material containing a conventional petrochemical-based compound is thermally decomposed is 262°C. The graph in Figure 3 shows the results of TGA analysis (10°C / min, N2).

[0084] 4, the thermomechanical properties of the cured material including the isohexide-based compound according to one embodiment of the present invention are shown. The properties of the cured material including the isohexide-based organic compound including silyl ether are indicated as "invention", and the properties of the cured material including the conventional petrochemical-based compound are indicated as "conventional".

[0085] The x-axis of FIG. 4 is temperature (° C.) and the y-axis is pressure (Pa). The glass transition temperature T g The glass transition temperature T of cured materials containing conventional petrochemical-based compounds is 108°C. g The temperature is 88°C. The graph in Figure 4 shows the results of rheometer analysis (10°C / min, CD 5%, 1 Hz).

[0086] FIG. 5 is a graph illustrating an isohexide-based organic or non-organic compound according to an embodiment of the present invention.

[0087] Referring to FIG. 5, the results of 92-Si-NMR analysis of an isohexide-based organic or inorganic compound according to Example 1 of the present invention, which will be described later, are shown.

[0088] T n (n=0, 1, 2, 3) is a general method of expressing siloxane bonds, where T means that there are three Si-O bonds based on the target Si atom, and n indicates the number of siloxane bonds (Si-O-Si) based on the target Si atom. As can be seen from Figure 5, the synthesized isohexide-based organic or non-organic compounds have three types of T 0 Species, two species of T 1 Species, a kind of T 2 It was found to contain unreacted T 0 Since no species (-42 ppm) was detected, it is inferred that the methoxy group of ECTMS reacted with the alcohol group of isosorbide to form a silyl ether bond.

[0089] Working Example Example 1 2-(3,4-Epoxycyclohexyl)ethyltrimethoxysilane (ECTMS, Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 100 ml two-neck flask in a ratio of 19.7 g:17.5 g:3.1 g, and the mixture was stirred at 80° C. for 24 hours to obtain an isohexide-based organic or inorganic compound having the average unit chemical formula of Chemical Formula 8 below. [ka]

[0090] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 2,500, a weight average molecular weight of about 12,000, and a polydispersity index (PDI) of about 4.9.

[0091] The biocarbon content of the synthesized isohexide-based organic or non-organic compound was measured according to ASTM D 6866 and it was found to contain about 50.6% biocarbon.

[0092] Example 2 2-(3,4-Epoxycyclohexyl)ethyltrimethoxysilane (ECTMS, Sigma-Aldrich), trimethylmethoxysilane (Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 200 ml two-neck flask in a ratio of 19.9 g:1.7 g:33.0 g:3.8 g, and the mixture was stirred at 80° C. for 24 hours to obtain an isohexide-based organic or inorganic compound having an average unit chemical formula of Chemical Formula 9 below. [ka]

[0093] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 1,250, a weight average molecular weight of about 6,470, and a polydispersity index (PDI) of about 5.2.

[0094] The biocarbon content of the synthesized isohexide-based organic compound was measured according to ASTM D 6866 and found to be about 64.7% biocarbon.

[0095] Example 3 Triethoxy-[3-[(3-ethyloxetan-3-yl)methoxy]propyl]silane (BenchChem), tetraethyl orthosilicate (Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 100 mL two-neck flask in a ratio of 11.4 g:2.5 g:27.8 g:2.5 g, and the mixture was stirred at 80° C. for 24 hours to obtain an isohexide-based organic or inorganic compound having an average unit chemical formula of Chemical Formula 10 below. [ka]

[0096] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 1,025, a weight average molecular weight of about 4,800, and a polydispersity index (PDI) of about 4.7.

[0097] The biocarbon content of the synthesized isohexide-based organic compound was measured according to ASTM D 6866 and found to be about 74.8% biocarbon.

[0098] Example 4 2-(3,4-Epoxycyclohexyl)ethyltrimethoxysilane (ECTMS, Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 100 ml two-neck flask in a ratio of 6.5 g:34.6:2.5 g, and the mixture was stirred at 80° C. for 24 hours to obtain an isohexide-based organic or inorganic compound having the average unit chemical formula of Chemical Formula 11 below. [ka]

[0099] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 980, a weight average molecular weight of about 2,890, and a polydispersity index (PDI) of about 2.9.

[0100] The biocarbon content of the synthesized isohexide-based organic compound was measured according to ASTM D 6866 and found to be about 82.6% biocarbon.

[0101] Example 5 3-Glycidoxypropyl methoxysilane (Gelest), (3-glycidoxypropyl)dimethylethoxysilane (Gelest), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 200 ml two-neck flask in a ratio of 42.2 g:7.8 g:20.9 g:3.7 g, and stirred at 80° C. for 24 hours. Then, about 1.0 g of DI water was added, and stirred at 80° C. for 24 hours to obtain an isohexide-based organic or inorganic compound having the average unit chemical formula of Chemical Formula 12 below. [ka]

[0102] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 4,850, a weight average molecular weight of about 14,500, and a polydispersity index (PDI) of about 3.0.

[0103] The biocarbon content of the synthesized isohexide-based organic or non-organic compound was measured according to ASTM D 6866 and found to be about 35.6% biocarbon.

[0104] Example 6 (3-Glycidoxypropyl)dimethoxymethylsilane (Sigma-Aldrich), tetraethyl orthosilicate (Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 100 ml two-neck flask in a ratio of 27.5 g:5.2 g:14.6 g:3.5 g, and the mixture was stirred at 80° C. for 24 hours to obtain an isohexide-based organic or inorganic compound having the average unit chemical formula of Chemical Formula 13 below. [ka]

[0105] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 3,420, a weight average molecular weight of about 11,800, and a polydispersity index (PDI) of about 3.5.

[0106] The biocarbon content of the synthesized isohexide-based organic compound was measured according to ASTM D 6866 and found to be about 39.7% biocarbon.

[0107] Example 7 3-Aminopropyltrimethoxysilane (Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 100 ml two-neck flask in a ratio of 46.3 g:9.4 g:2.8 g, and the mixture was stirred at 80° C. for 24 hours. Then, about 1.0 g of DI water and 0.1 g of potassium hydroxide (Sigma-Aldrich) were added, and the mixture was stirred at 80° C. for 24 hours to obtain an isohexide-based organic or inorganic compound having the average unit chemical formula of Chemical Formula 14 below. [ka]

[0108] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 3,850, a weight average molecular weight of about 12,500, and a polydispersity index (PDI) of about 3.2.

[0109] The biocarbon content of the synthesized isohexide-based organic compound was measured according to ASTM D 6866 and found to be about 32.1% biocarbon.

[0110] Example 8 3-Aminopropyltrimethoxysilane (Sigma-Aldrich), dimethoxydiphenylsilane (Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 200 mL two-neck flask in a ratio of 25.6 g:17.5 g:20.9 g:3.8 g, and the mixture was stirred at 80° C. for 24 hours to obtain an isohexide-based organic or inorganic compound having the average unit chemical formula of Formula 15 below. [ka]

[0111] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 2,450, a weight average molecular weight of about 9,810, and a polydispersity index (PDI) of about 4.0.

[0112] The biocarbon content of the synthesized isohexide-based organic compound was measured according to ASTM D 6866 and found to be about 38.9% biocarbon.

[0113] Example 9 3-Glycidoxypropyltrimethoxysilane (Gelest), (3-glycidoxypropyl)dimethoxymethylsilane (Sigma-Aldrich), tetraethyl orthosilicate (Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were mixed in the following amounts: 20.3 g: 6.3 g: 17.9 g: 12.5 g. :3.1g The mixture was added to a 200 mL two-neck flask in the ratio of 0.8 g of 0.1 N dilute hydrochloric acid (Sigma-Aldrich) and stirred at 80° C. for 24 hours to obtain an isohexide-based organic or inorganic compound having the average unit formula of Formula 16 below. [ka] [Chemical formula 16] Average unit chemical formula of the isohexide-based organic compound of Example 9

[0114] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 4,570, a weight average molecular weight of about 14,250, and a polydispersity index (PDI) of about 3.1.

[0115] The biocarbon content of the synthesized isohexide-based organic compound was measured according to ASTM D 6866 and found to be about 39.5% biocarbon.

[0116] Example 10 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (ECTMS, Sigma-Aldrich), dimethoxydimethylsilane (Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 100 ml two-neck flask in a ratio of 13.0 g:19.0 g:7.7 g:2.8 g, and the mixture was stirred at 80° C. for 24 hours. Then, about 2.8 g of DI water and 0.1 g of potassium hydroxide (Sigma-Aldrich) were added, and the mixture was stirred at 80° C. for 24 hours to obtain an isohexide-based organic or inorganic compound having the average unit chemical formula of Chemical Formula 17 below. [ka]

[0117] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 2,840, a weight average molecular weight of about 10,380, and a polydispersity index (PDI) of about 3.7.

[0118] The biocarbon content of the synthesized isohexide-based organic compound was measured according to ASTM D 6866 and found to be about 28.5% biocarbon.

[0119] Example 11 3-(Trimethoxysilyl)propyl methacrylate (Sigma-Aldrich), dimethoxydimethylsilane (Sigma-Aldrich), tetraethyl orthosilicate (Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 100 ml two-neck flask in a ratio of 5.9 g:17.2 g:9.9 g:3.5 g:1.8 g, and the mixture was stirred at 80° C. for 24 hours. Then, about 3.4 g of 0.1 N dilute hydrochloric acid (Sigma-Aldrich) was added, and the mixture was stirred at 80° C. for 24 hours to obtain an isohexide-based organic or inorganic compound having the average unit chemical formula of Chemical Formula 18 below. [ka]

[0120] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 3,580, a weight average molecular weight of about 9,840, and a polydispersity index (PDI) of about 2.7.

[0121] The biocarbon content of the synthesized isohexide-based organic compound was measured according to ASTM D 6866 and found to be about 22.5% biocarbon.

[0122] Example 12 Vinyltrimethoxysilane (Sigma-Aldrich), dimethoxydimethylsilane (Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 100 ml two-neck flask in a ratio of 9.4 g:26.7 g:4.6 g:1.5 g, and the mixture was stirred at 80° C. for 24 hours. Then, about 5.1 g of 0.05N dilute hydrochloric acid (Sigma-Aldrich) was added, and the mixture was stirred at 80° C. for 24 hours to obtain an isohexide-based organic or inorganic compound having the average unit chemical formula of Chemical Formula 19 below. [ka]

[0123] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 2,560, a weight average molecular weight of about 7,520, and a polydispersity index (PDI) of about 2.9.

[0124] The biocarbon content of the synthesized isohexide-based organic compound was measured according to ASTM D 6866 and found to be about 22.9% biocarbon.

[0125] Example 13 (3-Mercaptopropyl)trimethoxysilane (Sigma-Aldrich), tetraethyl orthosilicate (Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 100 ml two-neck flask in a ratio of 24.2 g:6.4 g:22.5 g:3.1 g, and the mixture was stirred at 80° C. for 24 hours to obtain an isohexide-based organic or inorganic compound having the average unit chemical formula of Chemical Formula 20 below. [ka]

[0126] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 2,150, a weight average molecular weight of about 11,900, and a polydispersity index (PDI) of about 5.5.

[0127] The biocarbon content of the synthesized isohexide-based organic compound was measured according to ASTM D 6866 and found to be about 70.2% biocarbon.

[0128] Example 14 3-(Triethoxysilyl)propyl isocyanate (Sigma-Aldrich), dimethoxydiphenylsilane (Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 100 ml two-neck flask in a ratio of 23.6 g:11.6 g:13.9 g:2.1 g, and then stirred at 80° C. for 24 hours. Then, about 0.4 g of 0.1 N potassium hydroxide aqueous solution (Sigma-Aldrich) was added, and an isohexide-based organic or inorganic compound having the average unit chemical formula of the following Chemical Formula 21 was obtained. [ka]

[0129] The molecular weight of the synthesized isohexide-based organic compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 3,820, a weight average molecular weight of about 7,890, and a polydispersity index (PDI) of about 2.1.

[0130] The biocarbon content of the synthesized isohexide-based organic compound was measured according to ASTM D 6866 and found to be about 35.4% biocarbon.

[0131] Comparative Example 1 2-(3,4-Epoxycyclohexyl)ethyltrimethoxysilane (ECTMS, Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 100 ml two-neck flask in a ratio of 3.5 g:39.7 g:0.5 g, and the mixture was stirred at 80° C. for 24 hours to obtain a synthesis product. However, it was confirmed that the product was not homogeneous and phase separation occurred.

[0132] Comparative Example 2 Vinyltrimethoxysilane (Sigma-Aldrich), dimethoxydimethylsilane (Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were added to a 100 ml two-neck flask in a ratio of 10.6 g: 32.2 g: 2.6 g: 1.1 g, and then stirred at 80° C. for 24 hours. Next, about 5.8 g of 0.05N dilute hydrochloric acid (Sigma-Aldrich) was added, and then stirred at 80° C. for 24 hours to obtain a compound having an average unit chemical formula of the following chemical formula 22. [ka]

[0133] The molecular weight of the compound was analyzed by gel permeation chromatography (GPC), and it was found to have a number average molecular weight of about 2,840, a weight average molecular weight of about 8,510, and a polydispersity index (PDI) of about 3.0.

[0134] The biocarbon content of the organic or non-organic compound was measured according to ASTM D 6866 and found to be about 11.5% biocarbon.

[0135] Comparative Example 3 3-Glycidoxypropyltrimethoxysilane (Gelest), (3-glycidoxypropyl)dimethoxymethylsilane (Sigma-Aldrich), tetraethyl orthosilicate (Sigma-Aldrich), isosorbide (Sigma-Aldrich), and Amberlite IRA-400 (Sigma-Aldrich) were mixed in the following amounts: 22.9 g: 7.1 g: 23.5 g: 11.8 g :2.7g The mixture was added to a 200 mL two-neck flask in the ratio of 0.1 N to 0.6 g of dilute hydrochloric acid (Sigma-Aldrich) and stirred at 80° C. for 24 hours to obtain a synthesis product. However, it was confirmed that gelation occurred.

[0136] Examples 1 to 14 and Comparative Examples 1 to 3 show synthetic products obtained by reacting isohexide with combinations of silane compounds represented by Chemical Formula 4, Chemical Formula 5, Chemical Formula 6, and Chemical Formula 7, and the molar ratios of each reactant to the total reactants are summarized in Table 1 below.

[0137] [Table 1]

[0138] In this case, if the molar ratio of the silane compounds of the formulas 4, 5, and 6 to the total reactants is defined as f, the molar ratio of the silane compound of the formula 7 to the total reactants is defined as g, and the molar ratio of the isohexide to the total reactants is defined as h, then it was confirmed that in Examples 1 to 14, 0.1≦f≦0.9, 0≦g≦0.3, and 0.1≦h≦0.9 were satisfied, and the synthesis was well performed and the biocarbon content was 20% or more, so that it can meet the environmentally friendly policy regarding bio-based plastics. On the other hand, in the case of Comparative Example 1 where f<0.1 and h>0.9, it was confirmed that the synthesis was not performed well and phase separation occurred because the amount of silane compounds capable of forming a silyl ether bond with isohexide was relatively small. In addition, in the case of Comparative Example 2 where f>0.9 and h<0.1, it was confirmed that the biocarbon content was about 11.5%, which is less than 20%, and therefore does not meet the standard for bio-based plastics. In the case of Comparative Example 3 where g>0.3, it was confirmed that the condensation reaction proceeded excessively, resulting in gelation.

[0139] Although the embodiments of the present invention have been described with reference to the attached drawings, those skilled in the art will understand that the present invention can be embodied in other specific forms without changing the technical concept or essential features of the present invention. Therefore, it should be understood that the above-described embodiments are illustrative in all respects and are not limiting.

Claims

1. A first structure; and a curable reactive group, The first structure is an organic / inorganic compound having a structure in which silane and isohexide are chemically bonded via a silyl ether bond, The organic or inorganic compound satisfies the following chemical formula 1: 【Chemistry 1】 In the above chemical formula, a, b, c, and d are 0 or a positive number, and e is a positive number; The R １ , R ２ , R ３ , R ４ , R ５ , and R ６ each independently represents a curable reactive group, C １ ~C ２０ Alkyl groups of C ３ ~C ８ or a cycloalkyl group of C ６ ~C ２０ and wherein the aryl group is selected from the group consisting of The R １ , R ２ , R ３ , R ４ , R ５ , and R ６ At least one of the groups contains a curable reactive group; 0.1≦a+b+c≦0.9, 0≦d≦0.3, 0.1≦e≦0.9, An organic or inorganic compound in which a+b+c+d+e=1.

2. 2. The organic compound of claim 1 further comprising a siloxane group bonded to said silyl ether group.

3. 2. The organic or inorganic compound of claim 1, wherein the curable reactive groups are selected from the group consisting of epoxy groups, amine groups, acrylic groups, mercapto groups, carboxyl groups, vinyl groups, nitro groups, sulfone groups, hydroxyl groups, urethane groups, ureido, isocyanate, oxetane groups, or combinations thereof.

4. 2. The organic or inorganic compound of claim 1, wherein the isohexide comprises at least one of isosorbide, isomannide, isoidide, and combinations thereof.

5. Providing a silane compound; Providing isohexide; reacting said silane compound with said isohexide; The silane compound is reacted with the isohexide to form a silyl ether bond, The silane compound is selected from the group consisting of the following formulas 4 to 7, or a combination thereof: 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 The R １ , R ２ , R ３ , R ４ , R ５ , and R ６ each independently represents a curable reactive group, C １ ~C ２０ Alkyl groups of C ３ ~C ８ or a cycloalkyl group of C ６ ~C ２０ and wherein the aryl group is selected from the group consisting of The R １ , R ２ , R ３ , R ４ , R ５ , and R ６ At least one of the groups contains a curable reactive group; The R Ｉ , R ＩＩ , R ＩＩＩ , R ＩＶ are each independently hydrogen, linear C １ ~C ６ Alkyl groups of C3 to C6 ６ Contains an alkyl group, The molar ratio of the silane compounds of the formulas 4, 5, and 6 to the total reactants is f, The molar ratio of the silane compound of Formula 7 to the total reactants is g, The molar ratio of said isohexide to the total reactants is defined as h; A method for producing an organic or inorganic compound, wherein 0.1≦f≦0.9, 0≦g≦0.3, 0.1≦h≦0.9, and f+g+h=1.

6. 6. The method of claim 5 further comprising forming a siloxane bond.

7. The method for producing an organic or inorganic compound according to claim 6, wherein the formation of the siloxane bond includes carrying out at least one reaction selected from the group consisting of a hydration reaction and a condensation reaction between the silane compounds.

8. reacting the silane compound with the isohexide; and using a catalyst to promote the formation of said siloxane bonds, The catalyst is Acid catalysts such as acetic acid, hydrochloric acid, hydrogen fluoride, sulfuric acid, nitric acid, chlorosulfonic acid, iodic acid, and pyrophosphoric acid; Basic catalysts such as potassium hydroxide, sodium hydroxide, barium hydroxide, and imidazole; 7. The method of claim 6, wherein the organic compound is one of the group consisting of an ion exchange resin, water, and combinations thereof.

9. 6. The method for producing an organic or inorganic compound according to claim 5, wherein the curable reactive group contained in the silane compound is an epoxy group and / or an oxetane group.

10. The silane compound may be 5,6-epoxyhexyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, 3-ethyl-3-[[3-triethoxysilyl)propoxy]methyl]oxetane, 7-trimethoxysilyl-4-thiazol-2-yl, 5-epoxyhexyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, 3-ethyl-3-[[3-triethoxysilyl)propoxy]methyl]oxetane, 7-trimethoxysilyl-4-thiazol-2-yl, Arheptanoic acid-(3-ethyl-oxetan-3-yl)methyl ester, N-(3-triethoxysilylpropyl)-(3-ethyloxetan-3-yl)-methylcarbamic acid, 2-(3-triethoxysilylpropylthio)succinic acid-bis-[3-ethyloxetan-3-yl)-methyl] ester, (3,4-ethoxycyclohexyl)ethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl ( 10. The method for producing an organic or inorganic compound according to claim 9, wherein the organic or inorganic compound is any one of dimethoxy(methyl)(3-(oxiran-2-yl)propyl)silane, diethoxy(methyl)(3-(oxiran-2-yl)propyl)silane, methyl(3-(oxirane-2-yl)propyl)silane, (3-glycidoxypropyl)dimethoxymethylsilane, (3-glycidoxypropyl)diethoxymethylsilane, (3-glycidoxypropyl)methylsilanediol, (3-glycidoxypropyl)dimethylethoxysilane, and 3-glycidoxypropyldimethylmethoxysilane.

11. The method for producing an organic or inorganic compound according to claim 5, wherein the curable reactive group contained in the silane compound includes at least one of an amine group, a ureido group, an isocyanate group, and a mercapto group.

12. The silane compound may be 4-aminobutyltriethoxysilane, 4-amino-3,3-dimethylbutyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-(6-aminohexyl)aminomethyltriethoxysilane, N-(6-aminohexyl)aminopropyltrimethoxysilane, n-(2-aminoethyl)-11-aminoundecyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropylsilanetriol, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, , 3-triethoxysilyl-N-(1,3 dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N-(vinylbenzyl)-2-aminoethyl 3-aminopropyltrimethoxysilane hydrochloride, 3-(m-aminophenoxy)propyltrimethoxysilane, m-aminophenyltrimethoxysilane, p-aminophenyltrimethoxysilane, aminophenyltrimethoxysilane, 3-aminopropyltris(methoxyethoxyethoxy)silane, 11-aminoundecyltriethoxysilane, 2- (4-pyridylethyl)triethoxysilane, 2-(2-pyridylethyl)trimethoxysilane, N-(3-trimethoxysilanepropyl)pyrrole, 3-aminopropylsilanetriol, (aminoethylaminomethyl)phenethyltrimethoxysilane, 3-ureidopropyltrialkoxysilane, 3-isocyanatopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldiethoxysilane 10. The method for producing an organic or inorganic compound according to claim 9, wherein the organic or inorganic compound is any one of N-(2-aminoethyl)-3-aminoisobutylmethyldimethoxysilane, 4-amino-3,3-dimethylbutylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 1-amino-2-(dimethylethoxysilyl)propane, 3-aminopropyldiisopropylethoxysilane, 3-aminopropyldimethylethoxysilane, and N-(2-aminoethyl)-3-aminoisobutyldimethylmethoxysilane.

13. an organic or inorganic compound including a first structure and a curable reactive group; and a hardener, the first structure has a structure in which silane and isohexide are chemically bonded via a silyl ether bond; the curable reactive group is any one of an epoxy group, an oxetane group, or a combination thereof; The organic or inorganic compound satisfies the following chemical formula 2: 【Chemistry 6】 In the above chemical formula, a, b, c, and d are 0 or a positive number, and e is a positive number; The R １ , R ２ , R ３ , R ４ , R ５ , and R ６ each independently represents a curable reactive group, C １ ~C ２０ Alkyl groups of C ３ ~C ８ or a cycloalkyl group of C ６ ~C ２０ and wherein the aryl group is selected from the group consisting of The R １ , R ２ , R ３ , R ４ , R ５ , and R ６ At least one of the groups contains a curable reactive group; 0.1≦a+b+c≦0.9, 0≦d≦0.3, 0.1≦e≦0.9, A curable composition, wherein a+b+c+d+e=1.

14. An initiator; A reactive diluent; and further comprising an additive, The curing agent is: The curable reactive group is any one of organic compounds having a silyl ether isohexide base with or without an amine group, an ureido group, an isocyanate group, or a mercapto group, an acid anhydride-based curing agent, an amine-based curing agent, an imidazole-based curing agent, a carboxylic acid-based curing agent, a phosphine-based curing agent, an iodine derivative-based curing agent, and a combination thereof; the initiator is any one of a photoacid generator, a photosalt generator, a thermal acid generator, and a combination thereof; The reactive diluent is any one of an epoxy reactive diluent, an oxetane reactive diluent, a polyethylene glycol, and a combination thereof; 14. The curable composition of claim 13, wherein the additive is any one of graphene, carbon nanotubes, fullerene, hexagonal boron nitride, boron nitride nanotubes, alumina, maxine, and combinations thereof.

15. The curable composition of claim 13 , wherein the first structure further comprises a siloxane bond.

Images