An isocyanate prepolymer composition using anhydrous sugar alcohol-alkylene glycol and polyhydric alcohol, an end-sealing isocyanate prepolymer composition produced from the prepolymer composition and an impact modifier containing the same, and an epoxy resin composition containing the impact modifier and an adhesive containing the same.

Abstract

The present invention relates to isocyanate prepolymer compositions using anhydrous sugar alcohol-alkylene glycol and polyhydric alcohols and their use, more specifically to environmentally friendly isocyanate prepolymer compositions produced by urethane reaction of a polyol composition containing anhydrous sugar alcohol-alkylene glycol, a polyether polyol, and a polyhydric alcohol, which is an alkylene oxide adduct of anhydrous sugar alcohol, with a polyisocyanate, in particular to isocyanate prepolymer compositions that can improve the T-peel strength and impact strength (especially impact strength at room temperature) of adhesive epoxy resin compositions to which an end-sealed isocyanate prepolymer composition produced using the same is applied as an impact modifier, an end-sealed isocyanate prepolymer composition using the prepolymer composition and an impact modifier containing the same, and an epoxy resin composition containing the impact modifier and an adhesive containing the same.

Description

Technical Field

[0001] The present invention relates to an isocyanate prepolymer composition using anhydrosugar alcohol - alkylene glycol and polyhydric alcohol and its use. More specifically, it relates to an environmentally friendly isocyanate prepolymer composition produced by subjecting a polyol composition containing an alkylene oxide adduct of anhydrosugar alcohol, i.e., anhydrosugar alcohol - alkylene glycol, a polyether polyol, and a polyhydric alcohol, and a polyisocyanate to a urethane reaction. In particular, it relates to an isocyanate prepolymer composition capable of improving the T - peel strength and impact strength (especially the impact strength at room temperature) of an epoxy resin composition for adhesion to which a terminated isocyanate prepolymer composition produced using this is applied as an impact modifier, the terminated isocyanate prepolymer composition using the prepolymer composition, an impact modifier containing the same, an epoxy resin composition containing the impact modifier, and an adhesive containing the same.

Background Art

[0002] Epoxy resins have excellent heat resistance, mechanical properties, electrical properties, and adhesiveness. Taking advantage of these properties, epoxy resins are used as encapsulating materials for wiring boards, circuit boards, multilayer circuit boards, semiconductor chips, coils, electrical circuits, etc. Epoxy resins are also used as resins for adhesives, paints, and fiber - reinforced resins.

[0003] Epoxy resins are widely used in various applications as thermosetting resins. They are also used as thermosetting matrices in prepregs composed of fibers incorporated into thermosetting matrices. Furthermore, due to their toughness, flexibility, adhesiveness, chemical resistance, etc., epoxy resins can be used as surface - coating materials and materials for adhesion, molding, lamination, etc., and various applications have been found in a wide range of industrial fields such as aerospace, automotive, electronic equipment, construction, furniture, green energy, and sports goods industries.

[0004] A wide range of epoxy resins are readily available and can be used depending on the reactivity required for a specific application. For example, resins can be solid, liquid, or semi-solid and have various reactivity levels depending on the application. The reactivity of an epoxy resin is often measured by its epoxy equivalent, which is the molecular weight of the resin containing a single reactive epoxy group. The lower the epoxy equivalent, the higher the reactivity of the epoxy resin. Different applications require different levels of reactivity, depending on whether the resin is present as a matrix in fiber-reinforced prepregs, adhesive coatings, or structural adhesives.

[0005] However, epoxy resin itself is brittle and has low strength, limiting its range of applications. To compensate for this, rubber additives and thermoplastic polymer additives are used, but these additives do not form chemical bonds with the epoxy resin, resulting in reduced corrosion resistance and environmental compatibility.

[0006] Hydrogenated sugars (also called "sugar alcohols") refer to compounds obtained by adding hydrogen to the reducing terminal group of sugars. Generally, HOCH2(CHOH) n It has the formula CH2OH (where n is an integer from 2 to 5) and is classified into tetrito, pentitol, hexitol, and heptitol (with 4, 5, 6, and 7 carbon atoms, respectively) depending on the number of carbon atoms. Among these, hexitol with 6 carbon atoms includes sorbitol, mannitol, iditol, and galactitol, with sorbitol and mannitol being particularly effective substances.

[0007] Anhydrous sugar alcohols are substances formed by removing one or more water molecules from within a hydride sugar. When one water molecule is removed, it becomes a tetraol with four hydroxyl groups in the molecule, and when two water molecules are removed, it becomes a diol with two hydroxyl groups in the molecule. They can be produced using hexitol derived from starch (for example, Patent Documents 1 and 2). Anhydrous sugar alcohols have long been of interest and research into their production methods has been conducted because they are environmentally friendly substances derived from renewable natural resources. Among these anhydrous sugar alcohols, isosorbide, produced from sorbitol, currently has the widest range of industrial applications.

[0008] Anhydrous sugar alcohols can be used in a variety of fields, including the treatment of cardiovascular diseases, as adhesives for patches, as solvents in pharmaceutical and cosmetic compositions such as oral hygiene agents, and as emulsifiers in the food industry. They also increase the glass transition temperature of polymers such as polyester, PET, polycarbonate, polyurethane, and epoxy resins, improving their strength. Because they are naturally derived and environmentally friendly, they are extremely useful in the plastics industry, including bioplastics. Furthermore, anhydrous sugar alcohols are known to be usable as adhesives, environmentally friendly plasticizers, biodegradable polymers, and environmentally friendly solvents for water-soluble lacquers. Thus, anhydrous sugar alcohols are attracting considerable attention due to their wide range of applications, and their industrial practical application is increasing.

[0009] Therefore, there is a need for the development of an impact modifier that is environmentally friendly because it is manufactured using anhydrous sugar alcohol, and can improve the strength of epoxy resins when added to structural adhesives containing epoxy resins. [Prior art documents] [Patent Documents]

[0010] [Patent Document 1] Korean Patent No. 10-1079518 Specification [Patent Document 2] Korean Patent Application Publication No. 10-2012-0066904 Specification [Overview of the project] [Problems that the invention aims to solve]

[0011] The object of the present invention is to provide an isocyanate prepolymer composition that is environmentally friendly by utilizing anhydrous sugar alcohol, and in particular can improve the T-peel strength and impact strength (especially impact strength at room temperature) of an adhesive epoxy resin composition to which an end-capturing isocyanate prepolymer composition produced using said sugar alcohol is applied as an impact modifier, an epoxy resin composition containing said impact modifier and an adhesive containing said impact modifier. [Means for solving the problem]

[0012] A first aspect of the present invention provides an isocyanate prepolymer composition produced by reacting a polyol composition containing anhydrous sugar alcohol-alkylene glycol, a polyether polyol, and a trivalent or higher polyhydric alcohol with a polyisocyanate using a urethane reaction, wherein the OH equivalent ratio of the anhydrous sugar alcohol-alkylene glycol to the total OH equivalent of the polyol composition is greater than 0.05 and less than 0.4, the OH equivalent ratio of the polyether polyol is greater than 0.2 and less than 0.6, the OH equivalent ratio of the trivalent or higher polyhydric alcohol is greater than 0.2 and less than 0.6, and the NCO equivalent ratio of the polyisocyanate to the total OH equivalent of the polyol composition (total NCO equivalent / total OH equivalent) is greater than 1.5 and less than 2.0.

[0013] A second aspect of the present invention provides a method for producing an isocyanate prepolymer composition, comprising the step of reacting a polyol composition containing anhydrous sugar alcohol-alkylene glycol, a polyether polyol, and a trivalent or higher polyhydric alcohol with a polyisocyanate using a urethane reaction, wherein the OH equivalent ratio of the anhydrous sugar alcohol-alkylene glycol to the total OH equivalent of the polyol composition is greater than 0.05 and less than 0.4, the OH equivalent ratio of the polyether polyol is greater than 0.2 and less than 0.6, the OH equivalent ratio of the trivalent or higher polyhydric alcohol is greater than 0.2 and less than 0.6, and the NCO equivalent ratio of the polyisocyanate to the total OH equivalent of the polyol composition (total NCO equivalent / total OH equivalent) is greater than 1.5 and less than 2.0.

[0014] A third aspect of the present invention provides an end-capturing isocyanate prepolymer composition produced by reacting an isocyanate prepolymer composition according to the first aspect of the present invention with an end-capturing agent.

[0015] A fourth aspect of the present invention provides an impact modifier comprising an end-capturing isocyanate prepolymer composition according to a third aspect of the present invention.

[0016] A fifth aspect of the present invention provides an epoxy resin composition comprising an impact modifier and an epoxy resin according to a fourth aspect of the present invention.

[0017] A sixth aspect of the present invention provides an adhesive comprising an epoxy resin composition according to a fifth aspect of the present invention. [Effects of the Invention]

[0018] The isocyanate prepolymer composition according to the present invention is environmentally friendly, and in particular, the end-capturing isocyanate prepolymer composition produced using it can significantly improve the T-peel strength and impact strength (especially impact strength at room temperature) of adhesive epoxy resin compositions to which it is applied as an impact modifier, compared to conventional structural adhesives. In addition, the isocyanate prepolymer composition according to the present invention uses a sugar alcohol anhydride, which is an environmentally friendly material, as a polyol raw material, thereby improving the value of the bio-based material and contributing to environmental affinity.

Mode for Carrying Out the Invention

[0019] Hereinafter, the present invention will be described in more detail.

[0020] <Isocyanate Prepolymer Composition and Method for Producing the Same> The isocyanate prepolymer composition of the present invention is produced by subjecting a polyol composition containing a sugar alcohol anhydride-alkylene glycol, a polyether polyol, and a polyhydric alcohol having three or more hydroxyl groups to a urethane reaction with a polyisocyanate. Here, the OH equivalent ratio of the sugar alcohol anhydride-alkylene glycol is more than 0.05 and less than 0.4, the OH equivalent ratio of the polyether polyol is more than 0.2 and less than 0.6, and the OH equivalent ratio of the polyhydric alcohol having three or more hydroxyl groups is more than 0.2 and less than 0.6, based on the total OH equivalent of the polyol composition. The NCO equivalent ratio (total NCO equivalent / total OH equivalent) of the polyisocyanate with respect to the total OH equivalent of the polyol composition is more than 1.5 and less than 2.0.

[0021] In the present invention, when the OH equivalent ratio of the sugar alcohol-alkylene glycol is 0.05 or less with respect to the total OH equivalent of the polyol composition, the molecular chain of the urethane reaction product becomes long, and relatively, the entanglement between molecules decreases. As a result, the T-peel strength of an epoxy resin adhesive containing a terminal-blocked isocyanate prepolymer composition produced using this as an impact modifier decreases, and the impact strength at room temperature also decreases. Therefore, unstable cracks may occur during the measurement of the impact strength at room temperature. Conversely, when the OH equivalent ratio of the sugar alcohol-alkylene glycol is 0.4 or more with respect to the total OH equivalent of the polyol composition, the length of the alkyl chain of the soft segment in the structure of the urethane reaction product becomes short. As a result, the T-peel strength and the impact strength at room temperature of an epoxy resin adhesive containing a terminal-blocked isocyanate prepolymer composition produced using this as an impact modifier decrease.

[0022] In one embodiment, the OH equivalent ratio of the sugar alcohol-alkylene glycol may be, for example, more than 0.05, 0.051 or more, 0.055 or more, 0.06 or more, 0.065 or more, 0.07 or more, 0.075 or more, or 0.08 or more with respect to the total OH equivalent of the polyol composition, and may also be less than 0.4, 0.39 or less, 0.38 or less, 0.37 or less, 0.36 or less, 0.35 or less, 0.34 or less, 0.33 or less, 0.32 or less, 0.31 or less, or 0.3 or less, but is not limited thereto.

[0023] In the present invention, if the OH equivalent ratio of the polyether polyol to the total OH equivalent of the polyol composition is 0.2 or less, the T-peel strength and impact strength at room temperature of the epoxy resin adhesive containing the end-capturing isocyanate prepolymer composition produced using the urethane reaction product as an impact modifier will decrease. Conversely, if the OH equivalent ratio of the polyether polyol to the total OH equivalent of the polyol composition is 0.6 or more, the T-peel strength and impact strength at room temperature of the epoxy resin adhesive containing the end-capturing isocyanate prepolymer composition produced using the urethane reaction product as an impact modifier will decrease, and unstable cracks may occur when measuring impact strength at room temperature.

[0024] In one embodiment, the OH equivalent ratio of the polyether polyol to the total OH equivalent of the polyol composition may be, for example, greater than 0.2, 0.21 or more, 0.22 or more, 0.23 or more, 0.24 or more, 0.25 or more, 0.26 or more, 0.27 or more, 0.28 or more, 0.29 or more, or 0.3 or more, and may also be less than 0.6, 0.59 or less, 0.58 or less, 0.57 or less, 0.56 or less, 0.55 or less, 0.54 or less, 0.53 or less, 0.52 or less, 0.51 or less, or 0.5 or less, but is not limited to these.

[0025] In the present invention, if the OH equivalent ratio of the trivalent or higher polyhydric alcohol to the total OH equivalent of the polyol composition is 0.2 or less, the T-peel strength of the epoxy resin adhesive containing the end-capturing isocyanate prepolymer composition produced using the urethane reaction product as an impact modifier will decrease, and the impact strength at room temperature will also decrease, potentially causing unstable cracks to occur during impact strength measurement at room temperature. Conversely, if the OH equivalent ratio of the trivalent or higher polyhydric alcohol to the total OH equivalent of the polyol composition is 0.6 or more, the T-peel strength and impact strength at room temperature of the epoxy resin adhesive containing the end-capturing isocyanate prepolymer composition produced using the urethane reaction product as an impact modifier will decrease. In one embodiment, the ratio of the OH equivalent of the trivalent or higher polyhydric alcohol to the total OH equivalent of the polyol composition may be, for example, greater than 0.2, 0.21 or more, 0.22 or more, 0.23 or more, 0.24 or more, 0.25 or more, 0.26 or more, 0.27 or more, 0.28 or more, 0.29 or more, or 0.3 or more, and may also be less than 0.6, 0.59 or less, 0.58 or less, 0.57 or less, 0.56 or less, 0.55 or less, 0.54 or less, 0.53 or less, 0.52 or less, 0.51 or less, or 0.5 or less, but is not limited to these.

[0026] In the present invention, if the ratio of the NCO equivalent of the polyisocyanate to the total OH equivalent of the polyol composition (total NCO equivalent / total OH equivalent) is 1.5 or less, the T-peel strength and impact strength at room temperature of the epoxy resin adhesive containing the end-capturing isocyanate prepolymer composition produced using the urethane reaction product as an impact modifier will decrease. Conversely, if the ratio of the NCO equivalent of the polyisocyanate to the total OH equivalent of the polyol composition (total NCO equivalent / total OH equivalent) is 2.0 or more, the T-peel strength and impact strength at room temperature of the epoxy resin adhesive containing the end-capturing isocyanate prepolymer composition produced using the urethane reaction product as an impact modifier will decrease, and unstable cracks may occur when measuring impact strength at room temperature.

[0027] In one embodiment, the ratio of the NCO equivalent of the polyisocyanate to the total OH equivalent of the polyol composition (total NCO equivalent / total OH equivalent) may be, for example, greater than 1.5, 1.51 or more, 1.52 or more, 1.53 or more, 1.54 or more, 1.55 or more, 1.56 or more, 1.57 or more, 1.58 or more, 1.59 or more, or 1.6 or more, and may also be less than 2.0, 1.99 or less, 1.98 or less, 1.97 or less, 1.96 or less, 1.95 or less, 1.94 or less, 1.93 or less, 1.92 or less, 1.91 or less, or 1.9 or less, but is not limited to these.

[0028] The following describes in more detail each component used in the production of the isocyanate prepolymer composition of the present invention.

[0029] Anhydrous sugar alcohol - alkylene glycol The aforementioned anhydrous sugar alcohol-alkylene glycol is an adduct obtained by reacting an alkylene oxide with a hydroxyl group at one or both ends (preferably both ends) of an anhydrous sugar alcohol.

[0030] The anhydrous sugar alcohol may be a mono-anhydrous sugar alcohol, a di-anhydrous sugar alcohol, or a combination thereof. A mono-anhydrous sugar alcohol is an anhydrous sugar alcohol formed by removing one water molecule from within a hydride sugar, and has a tetraol form with four hydroxyl groups in the molecule. In the present invention, the type of mono-anhydrous sugar alcohol is not particularly limited, but is preferably mono-anhydrous sugar hexitol, and more specifically may be 1,4-anhydrous hexitol, 3,6-anhydrous hexitol, 2,5-anhydrous hexitol, 1,5-anhydrous hexitol, 2,6-anhydrous hexitol, or a mixture of two or more of these. A di-anhydrous sugar alcohol is an anhydrous sugar alcohol formed by removing two water molecules from within a hydride sugar, and has a diol form with two hydroxyl groups in the molecule, and can be produced using hexitol derived from starch. Because di-anhydrous sugar alcohols are environmentally friendly materials derived from recyclable natural resources, they have attracted considerable interest for many years, and research on their production is progressing. Among these dianhydrous sugar alcohols, isosorbide, produced from sorbitol, currently has the widest range of industrial applications.

[0031] In one embodiment, the anhydrous sugar alcohol is a dianhydrohexitol, more specifically dianhydrohexitol, even more specifically 1,4:3,6-dianhydrohexitol, and even more specifically selected from the group consisting of isosorbide, isomannide, isoidide, or a combination thereof, and is preferably isosorbide.

[0032] In one embodiment, the alkylene oxide may be a linear alkylene oxide having 2 to 8 carbon atoms or a branched alkylene oxide having 3 to 8 carbon atoms, and more specifically, it may be ethylene oxide, propylene oxide, or a combination thereof.

[0033] In one embodiment, the anhydrous sugar alcohol-alkylene glycol is of the following formula (1) [ka] (In the formula, R 1 and R 2 Each of these independently represents a linear alkylene group with 2 to 8 carbon atoms or a branched alkylene group with 3 to 8 carbon atoms. m and n each independently represent an integer from 0 to 15, where m+n represents an integer from 1 to 30. The compound may also be represented by ). More specifically, in equation (1) above, R 1 and R 2 Each of these independently represents an ethylene group, a propylene group, or an isopropylene group, preferably R 1 and R 2 They are identical, m and n each independently represent integers from 1 to 14, where m+n represents integers from 2 to 25, more specifically from 3 to 20, and even more specifically from 5 to 20.

[0034] In one embodiment, the following isosorbide-propylene glycol, isosorbide-ethylene glycol, or a mixture thereof can be used as the anhydrous sugar alcohol-alkylene glycol.

[0035] [Isosorbide-Propylene Glycol] [ka] (In the formula, a and b each independently represent integers from 0 to 15, where a+b is an integer from 1 to 30; more specifically, a and b each independently represent integers from 1 to 14, where a+b is an integer from 2 to 25; more specifically, it may be an integer from 3 to 20; and even more specifically, an integer from 5 to 20.)

[0036] [Isosorbide-ethylene glycol] [ka] (In the formula, c and d each independently represent integers from 0 to 15, where c+d is an integer from 1 to 30; more specifically, c and d each independently represent integers from 1 to 14, where c+d may be an integer from 2 to 25, more specifically from 3 to 20, and even more specifically from 5 to 20.)

[0037] In one embodiment, the reaction molar ratio of the alkylene oxide to 1 mole of the anhydrous sugar alcohol is, for example, 1 mole or more, 2 moles or more, 3 moles or more, or 5 moles or more, and may also be 30 moles or less, 25 moles or less, or 20 moles or less, for example, 1 to 30 moles, preferably 2 to 25 moles, and more preferably 3 to 20 moles, but is not limited to these.

[0038] In one embodiment, the addition reaction between the anhydrous sugar alcohol and the alkylene oxide can be carried out, for example, in a high-pressure reactor capable of pressurization (e.g., pressurization of 3 MPa or more) in the presence of a base catalyst (e.g., alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, or alkaline earth metal hydroxides such as calcium hydroxide) at a high temperature (e.g., 100°C to 180°C, or 120°C to 160°C) for a certain period of time (e.g., 1 to 8 hours or 2 to 4 hours), but is not limited to these.

[0039] Polyether polyol The aforementioned polyether polyol is a polyether polymer compound having two or more hydroxyl groups in its molecule.

[0040] In one embodiment, the polyether polyol may include one or more selected from the group consisting of polyalkylene glycol, polytetrahydrofuran, or a combination thereof.

[0041] In one embodiment, the polyalkylene glycol may be poly(C1-C6)alkylene glycol, and more specifically, may be selected from the group consisting of polyethylene glycol, polypropylene glycol, polytetramethylene ether glycol, or a combination thereof.

[0042] In one embodiment, the number-average molecular weight (Mn: unit g / mol) of the polyether polyol may be 500 or more and less than 4,000. More specifically, the number-average molecular weight of the polyether polyol may be 500 or more, 600 or more, 700 or more, 800 or more, 900 or more, or 1,000 or more, and may also be less than 4,000, 3,900 or less, 3,800 or less, 3,700 or less, 3,600 or less, 3,500 or less, 3,400 or less, 3,300 or less, 3,200 or less, 3,100 or less, or 3,000 or less, but is not limited to these. Preferably, the number-average molecular weight of the polyether polyol may be 500 to 3,000. If the number-average molecular weight of the polyether polyol is too low compared to the aforementioned level, the reaction with the polyisocyanate may not proceed. Conversely, if it is too high compared to the aforementioned level, the property improvement effect may not be added, the raw material cost may increase, and the economic efficiency may decrease.

[0043] Trivalent or higher polyhydric alcohols The aforementioned polyhydric alcohols with a valency of three or more are compounds having three or more hydroxyl groups in their molecule.

[0044] In one embodiment, the trivalent or higher polyhydric alcohol may be one or more selected from the group consisting of glycerol, trimethylolpropane, triethanolamine, pentaerythritol, xylitol, sorbitol, or combinations thereof, and more specifically, it may be glycerol, triethanolamine, or combinations thereof, but is not limited thereto.

[0045] Any additional polyol In one embodiment, the polyol composition may optionally further contain polyol components other than the anhydrous sugar alcohol-alkylene glycol, polyether polyol, and trivalent or higher polyhydric alcohol ("additional polyol components").

[0046] In one embodiment, the additional polyol component can be selected from the group consisting of polyester polyols, polycaprolactone diols, polymer polyols obtained by polymerizing these polyols with vinyl compounds, or combinations thereof. Commonly used vinyl compounds include acrylonitrile, styrene, and methyl methacrylonitrile, with acrylonitrile typically used alone or in mixtures with styrene.

[0047] Urethane reaction with polyisocyanate and polyol compositions Another aspect of the present invention provides a method for producing an isocyanate prepolymer composition, comprising the step of reacting a polyol composition containing anhydrous sugar alcohol-alkylene glycol, a polyether polyol, and a trivalent or higher polyhydric alcohol with a polyisocyanate using a urethane reaction, wherein the OH equivalent ratio of the anhydrous sugar alcohol-alkylene glycol to the total OH equivalent of the polyol composition is greater than 0.05 and less than 0.4, the OH equivalent ratio of the polyether polyol is greater than 0.2 and less than 0.6, the OH equivalent ratio of the trivalent or higher polyhydric alcohol is greater than 0.2 and less than 0.6, and the NCO equivalent ratio of the polyisocyanate to the total OH equivalent of the polyol composition (total NCO equivalent / total OH equivalent) is greater than 1.5 and less than 2.0.

[0048] In the method for producing the isocyanate prepolymer composition according to the present invention, the description of anhydrous sugar alcohol-alkylene glycol (including the anhydrous sugar alcohol and alkylene oxide used in its production), polyether polyol, and trihydric or higher polyhydric alcohol is the same as described above.

[0049] In the present invention, the polyisocyanate can be used without particular limitations as long as it can be used in the production of polyurethane. For example, a polyisocyanate selected from the group consisting of aliphatic polyisocyanates, alicyclic polyisocyanates, aromatic aliphatic polyisocyanates, aromatic polyisocyanates, heterocyclic polyisocyanates, or combinations thereof can be used, and unmodified polyisocyanates, modified polyisocyanates, or both can be used.

[0050] In one embodiment, for example, the polyisocyanate is an aromatic polyisocyanate such as methylenediphenyl diisocyanate (MDI) (e.g., 2,4- or methylenediphenyl diisocyanate), xylenediisocyanate (XDI), m- or p-tetramethylxylenediisocyanate (TMXDI), toluene diisocyanate (TDI), di- or tetra-alkyldiphenylmethane diisocyanate, 3,3'-dimethyldiphenyl-4,4'-diisocyanate (TODI), phenylenediisocyanate (e.g., 1,3-phenylenediisocyanate, 1,4-phenylenediisocyanate), naphthalenediisocyanate (NDI), or 4,4'-dibenzyle diisocyanate; hydrogenated MDI (H12MDI), 1-methyl-2,4- Aliphatic polyisocyanates such as diisocyanatocyclohexane, 1,12-diisocyanato dodecane, 1,6-diisocyanato-2,2,4-trimethylhexane, 1,6-diisocyanato-2,4,4-trimethylhexane, isophorone diisocyanate (IPDI), tetramethoxybutane-1,4-diisocyanate, butane-1,4-diisocyanate, hexamethylene diisocyanate (HDI) (e.g., 1,6-hexamethylene diisocyanate), dimeric fatty acid diisocyanate, dicyclohexylmethane diisocyanate, cyclohexane diisocyanate (e.g., cyclohexane-1,4-diisocyanate), or ethylene diisocyanate; or combinations thereof, but not limited thereto.

[0051] In another embodiment, for example, the polyisocyanate is methylenediphenyl diisocyanate (MDI), ethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1,12-dodecane diisocyanate, cyclobutane-1,3-diisocyanate, cyclohexane-1,3-diisocyanate, cyclohexane-1,4-diisocyanate, isophorone diisocyanate, 2,4-hexahydrotoluene diisocyanate, 2,6-hexahydrotoluene diisocyanate, dicyclohexylmethane-4,4'-diisocyanate This may include, but is not limited to, toluene diisocyanate (HMDI), 1,3-phenylenediisocyanate, 1,4-phenylenediisocyanate, 2,4-toluenediisocyanate, 2,6-toluenediisocyanate, a mixture of 2,4-toluenediisocyanate and 2,6-toluenediisocyanate (2,4- / 2,6-isomer ratio = 80 / 20), diphenylmethane-2,4'-diisocyanate, diphenylmethane-4,4'-diisocyanate, polydiphenylmethane diisocyanate (PMDI), naphthalene-1,5-diisocyanate, or combinations thereof.

[0052] More specifically, the polyisocyanate may be methylenediphenyl diisocyanate (MDI), toluene diisocyanate (TDI), hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), or a combination thereof. In one embodiment, the urethane reaction can be carried out in the presence of an amine catalyst, an organometallic catalyst, or a mixture thereof. The type of amine catalyst is not particularly limited, but preferably one or more tertiary amine catalysts selected from tertiary amine catalysts can be used, and more specifically, one or more selected from the group consisting of triethylenediamine, triethylamine, N-methylmorpholine, N-ethylmorpholine, or combinations thereof can be used.

[0053] The type of organometallic catalyst is not particularly limited, but for example, one or more organotin catalysts selected from the group consisting of tin octoate, more specifically, dibutyltin dilaurate (DBTDL), bis[2-ethylhexanoate]tin, or combinations thereof can be used.

[0054] In one embodiment, the urethane reaction can be carried out at a high temperature (e.g., 50 to 100°C, preferably 50 to 80°C) for a suitable amount of time (e.g., 0.1 to 5 hours, preferably 0.5 to 2 hours), but is not limited thereto.

[0055] [End-capturing isocyanate prepolymer compositions, impact modifiers, epoxy resin compositions, and adhesives]

[0056] The present invention also provides an end-capped isocyanate prepolymer composition produced by the reaction of the isocyanate prepolymer composition of the present invention with an end-capped agent.

[0057] The present invention also provides an impact modifier comprising the aforementioned end-capturing isocyanate prepolymer composition.

[0058] The present invention also provides an epoxy resin composition comprising the aforementioned impact modifier and epoxy resin.

[0059] The present invention also provides an adhesive comprising the epoxy resin composition described above.

[0060] In one embodiment, the end-capturing agent may be one or more selected from the group consisting of phenolic compounds, triazine compounds, alcohol compounds, amine compounds, benzene compounds, dicarboxylic acid ester compounds, novolac compounds, or combinations thereof. More specifically, it may be one or more selected from the group consisting of phenolic compounds (e.g., allylphenol, t-butylphenol, phenol, bisphenol A, bisphenol M, bisphenol F, 1,3-dihydroxybenzene, 1,4-dihydroxybenzene, 1,2-dihydroxybenzene, phenolphthalein, o,o'-diallylbisphenol A, phenolphthalein, or combinations thereof), benzene compounds (e.g., econdé, phloroglucinol, resorcinol, naphthresorcinol, or combinations thereof), dicarboxylic acid ester compounds (e.g., gallic acid ester, maleic acid ester, or combinations thereof), novolac compounds (e.g., cresol novolac), or combinations thereof. Even more specifically, it may be a phenolic compound.

[0061] The epoxy resins mentioned above are solids, liquids, or semi-solids and exhibit various reactivity depending on the application. The reactivity of epoxy resins is often measured by epoxy equivalent, which is the molecular weight of the resin containing a single reactive epoxy group. The lower the epoxy equivalent, the higher the reactivity of the epoxy resin.

[0062] In one embodiment, the epoxy resin may be selected from the group consisting of bisphenol A-epichlorohydrin resin, bisphenol A diglycidyl ether resin, novolac-type epoxy resin, alicyclic epoxy resin, aliphatic epoxy resin, heterocyclic epoxy resin, glycidyl ester-type epoxy resin, bromide epoxy resin, bio-derived epoxy resin, epoxidized soybean oil, or combinations thereof, but is not limited thereto.

[0063] In another embodiment, the epoxy resin is a novolac type epoxy resin such as phenol novolac type epoxy resin and cresol novolac type epoxy resin; a bisphenol type epoxy resin such as bisphenol A type epoxy resin and bisphenol F type epoxy resin; an aromatic glycidylamine type epoxy resin such as N,N-diglycidylaniline, N,N-diglycidyltoluidine, diaminodiphenylmethanglycidylamine, and aminophenol type glycidylamine; a hydroquinone type epoxy resin, a biphenyl type epoxy resin, a stilbene type epoxy resin, a triphenolmethane type epoxy resin, a triphenolpropane type epoxy resin, an aluminum The epoxy resins may be selected from, but are not limited to, the group consisting of aralkyl epoxy resins such as quill-modified triphenolmethane type epoxy resins, triazine nucleus-containing epoxy resins, dicyclopentadiene-modified phenol type epoxy resins, naphthol type epoxy resins, naphthalene type epoxy resins, phenol aralkyl type epoxy resins having a phenylene and / or biphenylene skeleton, naphthol aralkyl type epoxy resins having a phenylene and / or biphenylene skeleton, aliphatic epoxy resins such as vinylcyclohexene dioxide, dicyclopentadiene oxide, alicyclic epoxy such as alicyclic diepate, or combinations thereof.

[0064] In yet another embodiment, the epoxy resin may be selected from, but is not limited to, the group consisting of bisphenol F type epoxy resin, cresol novolac type epoxy resin, phenol novolac type epoxy resin, biphenyl type epoxy resin, stilbene type epoxy resin, hydroquinone type epoxy resin, naphthalene skeleton type epoxy resin, tetraphenylolethane type epoxy resin, diphenyl phosphate (DPP) type epoxy resin, trishydroxyphenylmethane type epoxy resin, dicyclopentadienephenol type epoxy resin, diglycidyl ether of bisphenol A ethylene oxide adduct, diglycidyl ether of bisphenol A propylene oxide adduct, diglycidyl ether of bisphenol A, phenyl glycidyl ether, cresyl glycidyl ether, and other glycidyl ethers having one epoxy group, nuclear hydrogenated epoxy resins which are nuclear hydrogenated products of these epoxy resins, or combinations thereof.

[0065] In one embodiment, the reaction between the isocyanate prepolymer composition and the epoxy resin is a cyclization reaction between the isocyanate prepolymer composition and the epoxy resin, which can be carried out at a high temperature (e.g., 100-200°C, preferably 120-180°C) for a suitable time (e.g., 0.1-5 hours, preferably 0.5-2 hours) in the presence of a catalyst, such as an organic ammonium salt compound or other basic catalyst, but is not limited thereto.

[0066] In one embodiment, the impact modifier of the present invention may consist solely of the end-capturing isocyanate prepolymer composition of the present invention.

[0067] In another embodiment, the impact modifier of the present invention may further contain additional impact modifier components in addition to the end-sealed isocyanate prepolymer composition of the present invention, to the extent that the objectives of the present invention can be achieved. Examples of such additional impact modifier components include rubber-based impact modifiers such as carboxyl-terminated butadiene acrylonitrile (CTBN) and amine-terminated butadiene acrylonitrile (ATBN), thermoplastic polymer-based impact modifiers such as polyethersulfone, polyetherimide, polycarbonate, polyimide, polyamide, acrylonitrile butadiene styrene (ABS), and methacrylate butadiene styrene (MBS), or mixtures thereof.

[0068] In one embodiment, the additional impact modifier may be in the form of a core-shell.

[0069] In one embodiment, the impact modifier of the present invention may be included in an amount of 2 to 65 parts by weight, more specifically 5 to 60 parts by weight, or even more specifically 10 to 55 parts by weight, per 100 parts by weight of the total amount of the epoxy resin composition of the present invention, but is not limited thereto.

[0070] In one embodiment, the epoxy resin composition of the present invention may further include, in addition to the impact modifier and epoxy resin of the present invention, one or more selected from a curing agent, a curing accelerator, a filler, an adhesion promoter, or a combination thereof. As the curing agent, curing agents commonly used in this field can be used alone or in combination of two or more, for example, amine compounds such as benzyldimethylamine, tris(dimethylaminomethyl)phenol, and dimethylcyclohexylamine (e.g., tertiary amines); imidazole compounds such as 1-cyanoethyl-2-ethyl-4-methylimidazole, 2-ethyl-4-methylimidazole, and 1-benzyl-2-methylimidazole; organophosphorus compounds such as triphenylphosphine and triphenyl phosphite; quaternary phosphonium salts such as tetraphenylphosphonium bromide and tetra-n-butylphosphonium bromide; diazabicycloalkenes such as 1,8-diazabicyclo[5.4.0]undecene-7 and its organic salts; octi Organometallic compounds such as zinc acetate, tin octate, and aluminum acetylacetone complexes; quaternary ammonium salts such as tetraethylammonium bromide and tetrabutylammonium bromide; boron compounds such as boron trifluoride and triphenylborate; metal halides such as zinc chloride and stannous chloride; latent curing agents (e.g., dicyandiamide, high-melting-point-dispersible latent amine adducts obtained by adding amines to epoxy resins, etc.; microencapsulated latent curing agents in which the surface of imidazole-based, phosphorus-based, or phosphine-based accelerators is coated with polymers; amine salt-type latent curing agents; high-temperature dissociation-type thermal cationic polymerization-type latent curing agents such as Lewis salts and Brønsted salts, etc.), or combinations thereof may be selected from the group, but are not limited thereto.

[0071] In one embodiment, the curing agent may be selected from the group consisting of amine compounds, imidazole compounds, organophosphorus compounds, latent curing agents, or combinations thereof, but is not limited thereto.

[0072] Since epoxy resins typically require a temperature of 15°C or higher and a curing time of 24 hours or more for room temperature curing, rapid curing and low-temperature curing may be necessary. Therefore, for the purpose of accelerating curing, the epoxy resin composition of the present invention may further contain a curing accelerator. Examples of the curing accelerator include urea compounds, thiourea compounds, Lewis acid compounds, or mixtures thereof, and specifically include, but are not limited to, butylated urea, butylated melamine, butylated thiourea, and boron trifluoride.

[0073] If the epoxy resin composition of the present invention contains a curing accelerator, the amount used may be 0.01 to 3 parts by weight, more specifically 0.05 to 2 parts by weight, or even more specifically 0.08 to 1.5 parts by weight, per 100 parts by weight of the total of the epoxy resin and curing agent, but is not limited to these amounts. If the amount of curing accelerator used is too small, the curing reaction of the epoxy resin may not proceed sufficiently, potentially leading to problems such as a decrease in mechanical and thermal properties. Conversely, if the amount of curing accelerator used is too large, the curing reaction may proceed slowly even while the epoxy resin composition is stored, potentially leading to an increase in viscosity.

[0074] The aforementioned fillers are mixed with epoxy resins and curing agents and are used primarily to improve the mechanical properties of the cured product; generally, the mechanical properties improve as the amount added increases. Inorganic fillers include bulking agents such as talc, sand, silica, and calcium carbonate; reinforcing fillers such as mica, quartz, and glass fibers; special-purpose fillers such as quartz powder, graphite, alumina, and aerosil (for the purpose of imparting thixotropy); metallic fillers such as aluminum, aluminum oxide, iron, iron oxide, copper, and antimony oxide (Sb2O3) which contribute to the coefficient of thermal expansion, wear resistance, thermal conductivity, and adhesion; barium titanate; and organic fillers such as microplastic spheres (phenol resin, urea resin, etc.) for weight reduction. Furthermore, various glass fibers and chemical fiber fabrics can be treated as fillers in a broad sense in the manufacture of laminated products, as reinforcing fillers. To impart thixotropy to the resin (thixotropy refers to the property of being liquid when flowing and solid when stationary, which prevents the resin from flowing off vertical surfaces or running off during curing within immersed or impregnated laminates), large microparticles with a large unit surface area are used. For example, colloidal silica (Aerosil) or bentonite-based clay are used.

[0075] In one embodiment, the filler can be selected from the group consisting of, for example, glass fiber, carbon fiber, titanium oxide, alumina, talc, mica, aluminum hydroxide, calcium carbonate, or a combination thereof. The content of the filler in the composition may be 0.01 to 80 parts by weight, 0.01 to 60 parts by weight, or 0.1 to 50 parts by weight, based on 100 parts by weight of the total epoxy resin and curing agent.

[0076] In one embodiment, the adhesion promoter may be a polyurethane-modified epoxy resin, a polyurethane-modified silyl epoxy resin, or a combination thereof, but is not limited thereto.

[0077] The epoxy resin composition of the present invention may further contain one or more additive components commonly used in epoxy resin compositions, if necessary.

[0078] For example, the additive components used can be selected from the group consisting of antioxidants, UV absorbers, resin modifiers, silane coupling agents, diluents, colorants, defoamers, dispersants, viscosity modifiers, gloss modifiers, wetting agents, conductivity imparters, or combinations thereof.

[0079] The antioxidant can be used to further improve the heat resistance stability of the resulting cured product, and can be selected from the group consisting of, for example, phenolic antioxidants (such as dibutylhydroxytoluene), sulfur-based antioxidants (such as mercaptopropionic acid derivatives), phosphorus-based antioxidants (such as 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide), or combinations thereof, although this group is not particularly limited. The content of the antioxidant in the composition may be 0.01 to 10 parts by weight, 0.05 to 5 parts by weight, or 0.1 to 3 parts by weight per 100 parts by weight of the total of the epoxy resin and curing agent.

[0080] The UV absorber can be selected from the group consisting of, for example, benzotriazole-based UV absorbers such as TINUBIN P and TINUVIN 234 manufactured by BASF Japan; triazine-based UV absorbers such as TINUVIN 1577ED; hindered amine-based UV absorbers such as CHIMASSOLV 2020FDL; or combinations thereof. The amount of UV absorber in the composition may be 0.01 to 10 parts by weight, 0.05 to 5 parts by weight, or 0.1 to 3 parts by weight per 100 parts by weight of the total epoxy resin and curing agent.

[0081] The resin modifier is not particularly limited, but examples include polypropylene glycidyl ether, polymerized fatty acid polyglycidyl ether, polypropylene glycol, and flexibility-imparting agents such as urethane prepolymers. The content of the resin modifier in the composition may be 0.01 to 80 parts by weight, 0.01 to 50 parts by weight, or 0.1 to 20 parts by weight per 100 parts by weight of the total epoxy resin and curing agent.

[0082] The silane coupling agent is not particularly limited, but examples include chloropropyltrimethoxysilane, vinyltrichlorosilane, γ-methacrylateoxypropyltrimethoxysilane, and γ-aminopropyltriethoxysilane. The content of the silane coupling agent in the composition may be 0.01 to 20 parts by weight, 0.05 to 10 parts by weight, or 0.1 to 5 parts by weight, based on 100 parts by weight of the total of the epoxy resin and curing agent.

[0083] The aforementioned diluents are mixed with epoxy resins and curing agents and are primarily used to reduce viscosity. During use, they improve fluidity and defoaming properties, enhance penetration into fine details of parts, and allow for effective addition of fillers. Unlike solvents, diluents generally do not volatilize and remain in the cured product during resin curing. They are classified into reactive and non-reactive types. Reactive diluents have one or more epoxy groups and participate in the reaction, becoming incorporated into the cross-linked structure in the cured product, while non-reactive diluents are simply physically mixed and dispersed in the cured product. Commonly used reactive diluents include butyl glycidyl ether (BGE), phenyl glycidyl ether (PGE), aliphatic glycidyl ether (C12-C14), and modified t-carboxyglycidyl esters. Commonly used non-reactive diluents include dibutyl phthalate (DBP), dioctyl phthalate (DOP), nonylphenol, and Hysol. In one embodiment, the diluent is not particularly limited, but can be selected from the group consisting of, for example, n-butyl glycidyl ether, phenyl glycidyl ether, glycidyl methacrylate, vinylcyclohexene dioxide, diglycidylaniline, glycerin triglycidyl ether, or combinations thereof. The content of the diluent in the composition may be 0.01 to 80 parts by weight, 0.01 to 50 parts by weight, or 0.1 to 20 parts by weight, based on 100 parts by weight of the total epoxy resin and curing agent.

[0084] As a coloring agent, the resin can be colored using pigments or dyes. Conventional pigments such as titanium dioxide, cadmium red, shiny green, carbon black, chrome green, chrome yellow, navy blue, and shiny blue can be used as coloring agents.

[0085] Furthermore, various additives can be used, including defoamers and defoaming agents used to remove air bubbles in the resin, dispersants to enhance the dispersion effect between the resin and pigment, wetting agents to improve the adhesion between the epoxy resin and the material, viscosity modifiers, gloss modifiers to control the gloss of the resin, additives to improve adhesive strength, and additives to impart electrical properties.

[0086] The method for curing the epoxy resin composition of the present invention is not particularly limited, and conventionally known curing apparatuses such as a closed curing furnace or a tunnel furnace capable of continuous curing can be used. The heating method used for curing is also not particularly limited, and conventionally known methods such as hot air convection heating, infrared heating, and high-frequency heating can be used.

[0087] The curing temperature and curing time can be in the range of 80°C to 250°C and 30 seconds to 10 hours, respectively. In one embodiment, pre-curing can be performed at 80°C to 120°C for 0.5 hours to 5 hours, and post-curing can be performed at 120°C to 180°C for 0.1 hours to 5 hours. In one embodiment, for short-term curing, curing can be performed at 150°C to 250°C for 30 seconds to 30 minutes.

[0088] In one embodiment, the epoxy resin composition of the present invention may be stored separately as two or more components, for example, a component containing a curing agent and another component containing an epoxy resin, and these may be mixed before curing. In another embodiment, the epoxy resin composition of the present invention may be stored as a thermosetting composition with each component combined and can be cured as is. When stored as a thermosetting composition, it can be stored at low temperatures (typically -40°C to 15°C).

[0089] The present invention will be described in more detail below with reference to examples and comparative examples. However, the scope of the present invention is not limited to these. [Examples]

[0090] <Manufacturing of anhydrous sugar alcohol>

[0091] Production Example A1: Production of anhydrous sugar alcohol using 97 wt% glucose and a thin-film distillation apparatus A hydrogenation reaction was carried out on a glucose product with a purity of 97% in the presence of a nickel catalyst at a temperature of 125°C and a hydrogen pressure of 60 atmospheres to obtain 1,819 g of a liquid hydrogenated sugar composition with a concentration of 55% by weight (based on solid content, consisting of 96% by weight sorbitol, 0.9% by weight mannitol, and 3.1% by weight of polysaccharide alcohols of disaccharide or greater). This was then concentrated to obtain 1,000 g of a concentrated hydrogenated sugar composition. 1,000 g of the concentrated hydrolyzed sugar composition was placed in a batch reactor equipped with a stirrer, heated to 100°C, concentrated, and then 9.6 g of sulfuric acid was added. The reactor temperature was then raised to approximately 135°C, and a dehydration reaction was carried out under reduced pressure of approximately 45 mmHg to convert the product to anhydrous sugar alcohol. After the dehydration reaction was completed, the temperature of the reaction product was cooled to below 110°C, and approximately 15.7 g of 50% sodium hydroxide aqueous solution was added to neutralize the reaction product. The temperature was then cooled to below 100°C, and the product was concentrated under reduced pressure of 45 mmHg for more than 1 hour to remove residual water and low-boiling point substances, yielding approximately 831 g of anhydrous sugar alcohol conversion solution. Analysis of the obtained anhydrous sugar alcohol conversion solution by gas chromatography showed that the amount converted to isosorbide was 71.9% by weight, and the molar conversion rate from sorbitol to isosorbide was calculated to be 77.6%. The 831 g of the anhydrous sugar alcohol conversion solution obtained above was placed in a thin-film distillation apparatus (SPD) and distilled. The distillation was carried out at a temperature of 160°C and a vacuum pressure of 1 mbar, yielding approximately 589 g of distillate (distillation yield: approximately 70.9%). At this time, the purity of isosorbide in the distillate was measured to be 96.8%, and the distillation yield of isosorbide calculated from this was 95.3%. The anhydrous sugar alcohol distillate obtained above was mixed with 300 g of acetone (manufactured by Samchun Pure Chemical) as a solvent in a jacketed reactor, and then crystallization was carried out while lowering the temperature of the mixture from approximately 50°C to -10°C. After crystallization was completed, dehydration was performed, and the anhydrous sugar alcohol crystals were recovered from the mixed solution. The purity of the obtained anhydrous sugar alcohol crystals was 99.5% or higher.

[0092] <Production of anhydrous sugar alcohol-alkylene glycol>

[0093] Production Example B1: Production of Isosorbide-Ethylene Oxide 5-mol Adduct 100 g of isosorbide and 1.0 g of KOH obtained in the above production example A1 were placed in a pressurized reactor, and the pressurization and exhaust process was repeated three times using nitrogen gas. Then, the temperature was raised to 100°C to remove moisture from inside the reactor. After the moisture was completely removed, 150.7 g of ethylene oxide was slowly added to the reactor, and the reaction was carried out at 100°C to 140°C for 5 hours. After the reaction was complete, the internal temperature of the reactor was cooled to 50°C, 4 g of Ambosol MP20 was added as an adsorbent for metal removal, the mixture was heated again, and stirred at a temperature of 100°C to 120°C for 1 to 5 hours to remove metal ions. At this time, the metal ion content was monitored, and when no metal ions were detected, the internal temperature of the reactor was cooled to 60°C to 90°C, and residual by-products were removed by filtration to obtain 240 g of isosorbide-ethylene oxide 5 molar adduct as a clear liquid.

[0094] Manufacturing Example B2: Preparation of 5-mol Isosorbide-Propylene Oxide Adduct The procedure was the same as in Production Example B1, except that 198.7 g of propylene oxide was used instead of 150.7 g of ethylene oxide, and 290 g of a 5-mol adduct of isosorbide-propylene oxide was obtained as a clear liquid.

[0095] <Production of isocyanate prepolymer compositions and end-capped isocyanate prepolymer compositions>

[0096] Example A1: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-ethylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-ethylene oxide 5 molar adduct:glycerol = 0.5:0.1:0.4, NCO / OH equivalent ratio = 1.7) As the polyol component, 2.78 g of isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1, 75 g of polytetrahydrofuran, and 1.84 g of glycerol were placed in a reactor, along with 28.34 g of isophorone diisocyanate as the polyisocyanate component and 0.3 g of dibutyltin dilaurate (DBTDL) as the catalyst. The internal temperature of the reactor was slowly raised to 80°C. After the reaction temperature reached 80°C, the urethane reaction was carried out with stirring for 3 hours to produce an isocyanate prepolymer composition. After the urethane reaction was completed, the reactor temperature was adjusted to 60°C, and the NCO content of the isocyanate prepolymer composition was measured. Next, 1.4 equivalents of t-butylphenol were added to the reactor per 1 equivalent of NCO. The NCO content was then measured, and the reaction was terminated when the NCO content reached 0%. After the reaction was completed, the reaction product was cooled to room temperature to obtain 100 g of the end-capped isocyanate prepolymer composition.

[0097] Example A2: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-ethylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-ethylene oxide 5 molar adduct:glycerol = 0.3:0.3:0.4, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that the content of the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1 was changed from 2.78 g to 8.35 g, and the content of polytetrahydrofuran was changed from 75 g to 45 g. Then, a terminal encapsulation reaction was carried out in the same manner as in Example A1 to obtain 100 g of terminal encapsulated isocyanate prepolymer composition.

[0098] Example A3: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-ethylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-ethylene oxide 5 molar adduct:glycerol = 0.5:0.1:0.4, NCO / OH equivalent ratio = 1.9) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that the content of isophorone diisocyanate was changed from 28.34 g to 31.68 g. Subsequently, a end-capturing reaction was carried out in the same manner as in Example A1 to obtain 130 g of the end-capturing isocyanate prepolymer composition.

[0099] Example A4: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-propylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-propylene oxide 5 molar adduct:glycerol = 0.5:0.1:0.4, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that 3.28 g of the isosorbide-propylene oxide 5 molar adduct obtained in Production Example B2 was used instead of the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1. Then, a terminal encapsulation reaction was carried out in the same manner as in Example A1 to obtain 130 g of the terminal encapsulated isocyanate prepolymer composition.

[0100] Example A5: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-propylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-propylene oxide 5 molar adduct:glycerol = 0.3:0.3:0.4, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that 9.84 g of the isosorbide-propylene oxide 5 molar adduct obtained in Production Example B2 was used instead of the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1, and the polytetrahydrofuran content was changed from 75 g to 45 g. Then, a terminal encapsulation reaction was carried out in the same manner as in Example A1 to obtain 100 g of the terminal encapsulated isocyanate prepolymer composition.

[0101] Example A6: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-propylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-propylene oxide 5 molar adduct:glycerol = 0.5:0.1:0.4, NCO / OH equivalent ratio = 1.9) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that 3.28 g of the isosorbide-propylene oxide 5 molar adduct obtained in Production Example B2 was used instead of the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1, and the isophorone diisocyanate content was changed from 28.34 g to 31.68 g. Subsequently, a end-capping reaction was carried out in the same manner as in Example A1 to obtain 100 g of the end-capped isocyanate prepolymer composition.

[0102] Example A7: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-propylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-propylene oxide 5 molar adduct:glycerol = 0.5:0.1:0.4, NCO / OH equivalent ratio = 1.6) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that 3.5 g of the isosorbide-propylene oxide 5 molar adduct obtained in Production Example B2 was used instead of the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1, the polytetrahydrofuran content was changed from 75 g to 80 g, the glycerol content was changed from 1.84 g to 1.96 g, and the isophorone diisocyanate content was changed from 28.34 g to 28.45 g. Subsequently, an end-capturing reaction was carried out in the same manner as in Example A1 to obtain 120 g of the end-capturing isocyanate prepolymer composition.

[0103] Example A8: Preparation of an isocyanate prepolymer composition using a polyol composition containing polypropylene glycol, isosorbide-ethylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polypropylene glycol: isosorbide-ethylene oxide 5 molar adduct: glycerol = 0.5:0.1:0.4, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that 75 g of polypropylene glycol was used instead of polytetrahydrofuran and the content of isophorone diisocyanate was changed from 28.34 g to 28.45 g. Subsequently, a terminal encapsulation reaction was carried out in the same manner as in Example A1 to obtain 110 g of terminal encapsulated isocyanate prepolymer composition.

[0104] Example A9: Preparation of an isocyanate prepolymer composition using a polyol composition containing polypropylene glycol, isosorbide-propylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polypropylene glycol: isosorbide-propylene oxide 5 molar adduct: glycerol = 0.5:0.1:0.4, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that 3.28 g of the isosorbide-propylene oxide 5 molar adduct obtained in Production Example B2 was used instead of the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1, and 75 g of polypropylene glycol was used instead of polytetrahydrofuran. Then, a terminal encapsulation reaction was carried out in the same manner as in Example A1 to obtain 110 g of the terminal encapsulated isocyanate prepolymer composition.

[0105] Example A10: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-propylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-propylene oxide 5 molar adduct:glycerol = 0.58:0.12:0.3, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that 3.94 g of the isosorbide-propylene oxide 5 molar adduct obtained in Production Example B2 was used instead of the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1, the polytetrahydrofuran content was changed from 75 g to 87 g, and the glycerol content was changed from 1.84 g to 1.38 g. Subsequently, a end-capping reaction was carried out in the same manner as in Example A1 to obtain 120 g of the end-capped isocyanate prepolymer composition.

[0106] Example A11: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-propylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-propylene oxide 5 molar adduct:glycerol = 0.42:0.08:0.5, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that 2.62 g of the isosorbide-propylene oxide 5 molar adduct obtained in Production Example B2 was used instead of the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1, the polytetrahydrofuran content was changed from 75 g to 63 g, and the glycerol content was changed from 1.84 g to 2.30 g. Subsequently, a terminal encapsulation reaction was carried out in the same manner as in Example A1 to obtain 110 g of terminal encapsulated isocyanate prepolymer composition.

[0107] Example A12: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-propylene oxide 5 molar adduct, and triethanolamine, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-propylene oxide 5 molar adduct:triethanolamine = 0.5:0.1:0.4, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that 3.28 g of the 5 molar isosorbide-propylene oxide adduct obtained in Production Example B2 was used instead of the 5 molar isosorbide-ethylene oxide adduct obtained in Production Example B1, and 2.98 g of triethanolamine was used instead of glycerol. Then, a end-capping reaction was carried out in the same manner as in Example A1, except that 1.4 equivalents of 2-allylphenol were used instead of t-butylphenol, to obtain 110 g of the end-capped isocyanate prepolymer composition.

[0108] Comparative Example A1: Production of isocyanate prepolymer using polytetrahydrofuran and polyisocyanate (NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that the isosorbide-ethylene oxide 5 molar adduct and glycerol obtained in Production Example B1 were not used, only 100 g of polytetrahydrofuran was used as the polyol component, and the content of isophorone diisocyanate was changed from 28.34 g to 18.9 g. Subsequently, a end-capturing reaction was carried out in the same manner as in Example A1 to obtain 100 g of the end-capturing isocyanate prepolymer composition.

[0109] Comparative Example A2: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran and glycerol and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:glycerol = 0.6:0.4, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1 was not used, and the polytetrahydrofuran content was changed from 75 g to 90 g. Subsequently, a end-capturing reaction was carried out in the same manner as in Example A1 to obtain 100 g of the end-capturing isocyanate prepolymer composition.

[0110] Comparative Example A3: Production of an isocyanate prepolymer composition using a polyol composition containing polypropylene glycol and glycerol and a polyisocyanate (OH equivalent ratio of polypropylene glycol:glycerol = 0.6:0.4, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1 was not used, and 90 g of polypropylene glycol was used instead of polytetrahydrofuran. Then, a end-capturing reaction was carried out in the same manner as in Example A1 to obtain 100 g of the end-capturing isocyanate prepolymer composition.

[0111] Comparative Example A4: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-ethylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-ethylene oxide 5 molar adduct:glycerol = 0.5:0.1:0.4, NCO / OH equivalent ratio = 1.5) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that the content of isophorone diisocyanate was changed from 28.34 g to 25.01 g. Subsequently, a end-capturing reaction was carried out in the same manner as in Example A1 to obtain 100 g of the end-capturing isocyanate prepolymer composition.

[0112] Comparative Example A5: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-ethylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-ethylene oxide 5 molar adduct:glycerol = 0.5:0.1:0.4, NCO / OH equivalent ratio = 2.0) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that the content of isophorone diisocyanate was changed from 28.34 g to 33.35 g. Subsequently, a terminal encapsulation reaction was carried out in the same manner as in Example A1 to obtain 110 g of terminal encapsulated isocyanate prepolymer composition.

[0113] Comparative Example A6: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-ethylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-ethylene oxide 5 molar adduct:glycerol = 0.2:0.4:0.4, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that the content of the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1 was changed from 2.78 g to 11.88 g, the content of polytetrahydrofuran was changed from 75 g to 32 g, the content of glycerol was changed from 1.84 g to 1.96 g, and the content of isophorone diisocyanate was changed from 28.34 g to 30.23 g. Subsequently, a terminal encapsulation reaction was carried out in the same manner as in Example A1 to obtain 100 g of terminal encapsulated isocyanate prepolymer composition.

[0114] Comparative Example A7: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-propylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-propylene oxide 5 molar adduct:glycerol = 0.2:0.4:0.4, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that 14.0 g of the isosorbide-propylene oxide 5 molar adduct obtained in Production Example B2 was used instead of the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1, the polytetrahydrofuran content was changed from 75 g to 32 g, the glycerol content was changed from 1.84 g to 1.96 g, and the isophorone diisocyanate content was changed from 28.34 g to 30.23 g. Subsequently, an end-capturing reaction was carried out in the same manner as in Example A1 to obtain 100 g of the end-capturing isocyanate prepolymer composition.

[0115] Comparative Example A8: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-propylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-propylene oxide 5 molar adduct:glycerol = 0.55:0.05:0.4, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that 1.75 g of the isosorbide-propylene oxide 5 molar adduct obtained in Production Example B2 was used instead of the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1, the polytetrahydrofuran content was changed from 75 g to 88.0 g, the glycerol content was changed from 1.84 g to 1.96 g, and the isophorone diisocyanate content was changed from 28.34 g to 30.23 g. Subsequently, an end-capturing reaction was carried out in the same manner as in Example A1 to obtain 140 g of the end-capturing isocyanate prepolymer composition.

[0116] Comparative Example A9: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-propylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-propylene oxide 5 molar adduct:glycerol = 0.67:0.13:0.2, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that 4.26 g of the isosorbide-propylene oxide 5 molar adduct obtained in Production Example B2 was used instead of the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1, the polytetrahydrofuran content was changed from 75 g to 100.5 g, and the glycerol content was changed from 1.84 g to 0.92 g. Subsequently, a terminal encapsulation reaction was carried out in the same manner as in Example A1 to obtain 120 g of the terminal encapsulated isocyanate prepolymer composition.

[0117] Comparative Example A10: Preparation of an isocyanate prepolymer composition using a polyol composition containing polytetrahydrofuran, isosorbide-propylene oxide 5 molar adduct, and glycerol, and a polyisocyanate (OH equivalent ratio of polytetrahydrofuran:isosorbide-propylene oxide 5 molar adduct:glycerol = 0.33:0.07:0.6, NCO / OH equivalent ratio = 1.7) An isocyanate prepolymer composition was prepared in the same manner as in Example A1, except that 2.3 g of the isosorbide-propylene oxide 5 molar adduct obtained in Production Example B2 was used instead of the isosorbide-ethylene oxide 5 molar adduct obtained in Production Example B1, the polytetrahydrofuran content was changed from 75 g to 49.5 g, and the glycerol content was changed from 1.84 g to 2.76 g. Subsequently, an end-capping reaction was carried out in the same manner as in Example A1 to obtain 110 g of the end-capped isocyanate prepolymer composition.

[0118] <Manufacturing of epoxy resin compositions> Examples B1-B12 and Comparative Examples B1-B10: Preparation of epoxy resin composition As the epoxy resin, 3.0 g of bisphenol A diglycidyl ether (DGEBA)-based epoxy resin (YD-128, manufactured by Kukdo Chemical Co., Ltd.), 0.45 g of an epoxy resin curing agent (dicyandiamide (DICY), manufactured by Evonik, Dicyanex 1400F) which is stable at room temperature and induces a curing reaction at high temperatures, and 0.05 g of an epoxy resin curing accelerator (urea derivative (DIURON), manufactured by Evonik, Amicure UR-D) which is urea derivative (DIURON) which is urea derivative (manufactured by Evonik, Amicure UR-D), 1.0 g of calcium carbonate (CaCO3, manufactured by OMYA, OMYACARB 30-CN) with a particle size of 21-33 μm as a filler, 3.0 g of core-shell rubber (manufactured by KANEKA, MX-154) as an additional impact modifier, and 2.5 g of each end-encapsulated isocyanate prepolymer composition obtained in Examples A1-A12 and Comparative Examples A1-A10 as polyurethane impact modifiers according to the present invention were used. The epoxy resin compositions of Examples B1-B12 and Comparative Examples B1-B10, epoxy resin, curing agent, curing accelerator, filler, additional core-shell type impact modifier, and polyurethane-based impact reinforcer were prepared by mixing them in the composition ratios shown in Table 1 below. Specifically, an epoxy resin composition was prepared by adding epoxy resin, a curing agent, a curing accelerator, a filler, an additional core-shell type impact modifier, and a polyurethane-based impact modifier according to the present invention to a paste mixer and mixing for 15 minutes. [Table 1-1] [Table 1-2]

[0119] <Evaluation of physical properties of epoxy resin compositions> The epoxy resin compositions prepared in Examples B1-B12 and Comparative Examples B1-B10 were used as adhesives, and the physical properties of the adhesive test specimens were measured using the following method. The results are shown in Table 2 below.

[0120] (1) Evaluation of T-shaped peel strength (unit: N / 25mm) T-shaped peel strength was measured according to ASTM D-1876. A total of five measurements were taken for each specimen, and the average value was calculated. (2) Evaluation of impact strength at room temperature (unit: N / mm) Impact strength at room temperature was measured in accordance with ISO 11343. A total of five measurements were taken for each test specimen, and the average value was calculated.

[0121] <Ingredients Description> -PTG: Polytetrahydrofuran -PPG: Polypropylene glycol -Production Example B1: Isosorbide-ethylene oxide 5 molar adduct produced in Production Example B1 -Production Example B2: Isosorbide-propylene oxide 5 molar adduct produced in Production Example B2 -IPDI: Isophorone diisocyanate -Gly: Glycerol -TEA: Triethanolamine [Table 2]

[0122] As shown in Table 2 above, in the case of Examples B1 to B12 according to the present invention, the T-shaped peel strength was 360 N / 25 mm or more, indicating excellent adhesive strength, and at the same time, the impact strength at room temperature was also excellent at 40 N / mm. However, in Comparative Example B1, which used polyether polyol alone as the polyol component, surface delamination occurred on the adhesive test specimen, unstable cracks developed during impact strength measurement at room temperature, and impact resistance was very poor. Furthermore, in Comparative Examples B2 and B3, which did not use anhydrous sugar alcohol-alkylene glycol as the polyol component, the T-peel strength decreased and the adhesiveness was poor. In Comparative Example B4, the viscosity was too high, so increasing the viscosity of the epoxy resin composition resulted in a low T-peel strength, very poor adhesion, a decrease in impact strength at room temperature, and poor impact resistance. On the other hand, in Comparative Example B5, the viscosity was too low, so decreasing the viscosity of the epoxy resin composition resulted in a low T-peel strength, very poor adhesion, unstable cracks occurring during impact strength measurement at room temperature, and very poor impact resistance. In comparative examples B6 and B7, the T-peel strength decreased, resulting in poor adhesion, and the impact strength at room temperature also decreased, leading to poor impact resistance. Furthermore, in comparative example B8, the T-peel strength decreased, the adhesion was significantly poor, the impact strength at room temperature also decreased significantly, resulting in very poor impact resistance. In Comparative Example B9, the amount of glycerol added to the reaction was insufficient, resulting in a decrease in intermolecular entanglement and a deterioration in physical properties. On the other hand, in Comparative Example B10, the increase in intermolecular entanglement caused the viscosity of the polyurethane itself to become too high, resulting in a decrease in T-peel strength and impact strength at room temperature.

Claims

1. An isocyanate prepolymer composition produced by reacting a polyol composition containing anhydrous sugar alcohol-alkylene glycol, polyether polyol, and a polyhydric alcohol of trihydric or higher hydric value with a polyisocyanate using a urethane reaction, With respect to the total OH equivalent of the polyol composition, The OH equivalent ratio of the anhydrous sugar alcohol to alkylene glycol is greater than 0.05 and less than 0.

4. The OH equivalent ratio of the polyether polyol is greater than 0.2 and less than 0.

6. The OH equivalent ratio of the aforementioned trivalent or higher polyhydric alcohol is greater than 0.2 and less than 0.

6. An isocyanate prepolymer composition in which the ratio of the NCO equivalent of the polyisocyanate to the total OH equivalent of the polyol composition (total NCO equivalent / total OH equivalent) is greater than 1.5 and less than 2.

0.

2. The isocyanate prepolymer composition according to claim 1, wherein the anhydrous sugar alcohol-alkylene glycol is an adduct obtained by reacting an alkylene oxide with a hydroxyl group at one or both ends of the anhydrous sugar alcohol.

3. The isocyanate prepolymer composition according to claim 2, wherein the anhydrous sugar alcohol is dianhydrohexitol.

4. The isocyanate prepolymer composition according to claim 2, wherein the alkylene oxide is a linear alkylene oxide having 2 to 8 carbon atoms or a branched alkylene oxide having 3 to 8 carbon atoms.

5. The isocyanate prepolymer composition according to claim 1, wherein the polyether polyol comprises one or more selected from the group consisting of polyalkylene glycol, polytetrahydrofuran, or a combination thereof.

6. The isocyanate prepolymer composition according to claim 1, wherein the trivalent or higher polyhydric alcohol is one or more selected from the group consisting of glycerol, trimethylolpropane, triethanolamine, pentaerythritol, xylitol, sorbitol, or combinations thereof.

7. The process includes a step of reacting a polyol composition containing anhydrous sugar alcohol-alkylene glycol, polyether polyol, and trivalent or higher polyhydric alcohol with a polyisocyanate using a urethane reaction. With respect to the total OH equivalent of the polyol composition, The OH equivalent ratio of the anhydrous sugar alcohol to alkylene glycol is greater than 0.05 and less than 0.

4. The OH equivalent ratio of the polyether polyol is greater than 0.2 and less than 0.

6. The OH equivalent ratio of the aforementioned trivalent or higher polyhydric alcohol is greater than 0.2 and less than 0.

6. A method for producing an isocyanate prepolymer composition, wherein the ratio of the NCO equivalent of the polyisocyanate to the total OH equivalent of the polyol composition (total NCO equivalent / total OH equivalent) is greater than 1.5 and less than 2.

0.

8. An end-capturing isocyanate prepolymer composition produced by reacting the isocyanate prepolymer composition according to any one of claims 1 to 6 with an end-capturing agent.

9. The end-capturing isocyanate prepolymer composition according to claim 8, wherein the end-capturing agent is one or more selected from the group consisting of phenolic compounds, triazine compounds, alcohol compounds, amine compounds, benzene compounds, dicarboxylic acid ester compounds, novolac compounds, or combinations thereof.

10. An impact modifier comprising the end-capturing isocyanate prepolymer composition described in claim 8.

11. An epoxy resin composition comprising the impact modifier described in claim 10; and an epoxy resin.

12. The epoxy resin composition according to claim 11, wherein the epoxy resin is selected from the group consisting of bisphenol A-epichlorohydrin resin, bisphenol A diglycidyl ether resin, novolac-type epoxy resin, alicyclic epoxy resin, aliphatic epoxy resin, heterocyclic epoxy resin, glycidyl ester-type epoxy resin, bromide epoxy resin, bio-derived epoxy resin, epoxidized soybean oil, or a combination thereof.

13. The epoxy resin composition according to claim 11, further comprising one or more selected from a curing agent, a curing accelerator, a filler, an adhesion promoter, or a combination thereof.

14. The epoxy resin composition according to claim 11, further comprising additives selected from the group consisting of antioxidants, UV absorbers, resin modifiers, silane coupling agents, diluents, colorants, defoamers, defoaming agents, dispersants, viscosity modifiers, gloss modifiers, wetting agents, conductivity imparters, or combinations thereof.

15. An adhesive comprising the epoxy resin composition according to claim 11.

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