Resin leakage prevention agent and dual-curing adhesive composition comprising same

Abstract

The present invention relates to a compound represented by the following Chemical Formula 1 and a dual-curing adhesive composition comprising the same, the dual-curing adhesive composition comprising the compound according to one aspect being capable of effectively preventing a resin leakage phenomenon, and being capable of achieving excellent adhesive force and reliability after curing. [Chemical Formula 1] # imgabs0 # (In Chemical Formula 1, R, R1, L1 to L4 are the same as those described in the description. ).

Description

Technical Field

[0001] The present disclosure relates to a novel compound useful as a resin leakage preventer and a dual-cure adhesive composition containing the same. Background Art

[0002] For adhesives used in the assembly of camera modules, in order to minimize thermal damage to image sensors, etc. caused by high-temperature processing and to simultaneously meet the requirements of adhesion, reliability, and production efficiency, a dual-cure adhesive has been proposed that is pre-cured by light irradiation and then formally cured by heat.

[0003] In addition, as camera modules become smaller and thinner, the components of the camera modules also tend to be smaller, so the performance required of the adhesive that bonds and fixes the components is gradually becoming higher.

[0004] For example, as the width of the substrate to be bonded becomes smaller, resin bleed out (RBO) may occur, which may cause the adhesive to flow out. The bleed out resin may cause a decrease in bonding strength and reliability, so this phenomenon must be prevented. In addition, the smaller the bonding area, the easier it is for the bonding part of the adhesive to fall off or be damaged, so it is required to increase the bonding strength per unit area of ​​the adhesive and improve durability.

[0005] Patent Document 1: Korean Patent Publication No. 10-2021-0111552 (September 13, 2021) Summary of the invention

[0006] One aspect of the present invention provides a compound represented by the following Chemical Formula 1.

[0007] [Chemical formula 1]

[0008]

[0009] (In the chemical formula 1,

[0010] R is (C1-C30) alkyl,

[0011] R1 and R2 are each independently (C1-C30) alkyl;

[0012] L1 to L7 are each independently (C1-C7) alkylene.

[0013] The compound according to one aspect may be represented by Chemical Formula 2 below.

[0014] [Chemical formula 2]

[0015]

[0016] (In the chemical formula 2,

[0017] R1 is (C1-C30) alkyl;

[0018] L1 to L5 are each independently (C1-C7) alkylene.

[0019] The compound according to one aspect may be represented by Chemical Formula 3 below.

[0020] [Chemical formula 3]

[0021]

[0022] (In the chemical formula 3,

[0023] R1 is (C1-C30) alkyl;

[0024] R 11 ~R 14 are independently hydrogen or methyl.)

[0025] Another aspect of the present invention provides a resin blow-off (RBO) agent comprising the compound.

[0026] Another aspect of the present invention provides a dual-curing adhesive composition comprising the resin leakage preventer and an epoxy resin.

[0027] The dual-cure adhesive composition according to one aspect may further include a multifunctional monomer.

[0028] The multifunctional monomer may be a multifunctional acrylic compound.

[0029] The dual-cure adhesive composition according to one aspect may include 10 to 40 parts by weight of a resin leakage preventer based on 100 parts by weight of the epoxy resin.

[0030] The dual-cure adhesive composition according to one aspect may further include one or more additives selected from a thermal curing agent, a photoinitiator, a curing catalyst, and an inorganic filler.

[0031] Another aspect of the present invention provides a cured product prepared from the dual-cure adhesive composition.

[0032] When the compound according to one aspect is applied to an adhesive composition, it is possible to achieve an excellent anti-resin leakage effect without causing a decrease in the physical properties of the adhesive. Specifically, a dual-cure adhesive composition containing the compound according to one aspect can provide a cured product that not only has an extremely excellent anti-resin leakage effect, but also has excellent adhesion and reliability under a relatively low curing temperature condition.

[0033] Furthermore, the cured product according to one aspect can exhibit excellent moisture resistance even under high temperature and high humidity conditions, and can achieve a particularly high adhesive strength per unit area, and therefore can be expected to be effectively used as an adhesive layer between component parts of a camera module or the like. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 Schematic diagram of the method for measuring the anti-resin leakage effect.

[0035] Figure 2 Schematic diagram of the preparation method of the specimens for adhesion evaluation. DETAILED DESCRIPTION

[0036] Unless otherwise defined in this specification, all technical terms and scientific terms have the same meaning as those commonly understood by those skilled in the art to which the present invention belongs. The terms used for explanation in this specification are only used to effectively describe specific examples and are not intended to limit the present invention.

[0037] Unless otherwise indicated in the context, singular forms used in this specification may be intended to include plural forms.

[0038] Throughout this specification, when it is mentioned that a certain structural element "includes", "has", "contains" or "has", unless otherwise stated to the contrary, it means that other structural elements may be further included without excluding other structural elements, and elements, materials or processes that are not further listed are not excluded.

[0039] The numerical range used in this specification includes the lower limit and the upper limit and all values ​​within the range, the increments logically derived from the form and width of the defined range, all double-defined values, and all possible combinations of the upper and lower limits of the numerical range defined in different forms. Unless otherwise defined in this specification, the defined numerical range also includes values ​​outside the numerical range that may appear due to experimental errors or numerical rounding.

[0040] Unless otherwise defined in this specification, "about" may consider a value to be within 30%, 25%, 20%, 15%, 10%, or 5% of the stated value.

[0041] The term "(meth)acrylate" in the present specification may refer to both methacrylate and acrylate.

[0042] The present disclosure is described in detail below. However, the description is only for exemplary purposes, and the present disclosure is not limited to the specific implementation methods described exemplarily.

[0043] One aspect of the present invention provides a compound with a novel structure, which can effectively prevent resin bleeding (RBO) phenomenon without causing a decrease in the physical properties of an adhesive.

[0044] Specifically, the compound according to one aspect may be represented by the following Chemical Formula 1.

[0045] [Chemical formula 1]

[0046]

[0047] (In the chemical formula 1,

[0048] R is (C1-C30) alkyl,

[0049] R1 and R2 are each independently (C1-C30) alkyl;

[0050] L1 to L7 are each independently (C1-C7) alkylene.

[0051] The compound according to one aspect may be an anti-resin leakage additive (anti-resin leakage agent) for an adhesive, and after curing, can achieve an excellent anti-resin leakage effect without causing a decrease in the physical properties of the adhesive.

[0052] Specifically, the compound may be represented by the following Chemical Formula 2.

[0053] [Chemical formula 2]

[0054]

[0055] (In the chemical formula 2,

[0056] R1 is (C1-C30) alkyl;

[0057] L1 to L5 are each independently (C1-C7) alkylene.

[0058] Specifically, the compound may be represented by the following Chemical Formula 3.

[0059] [Chemical formula 3]

[0060]

[0061] (In the chemical formula 3,

[0062] R1 is (C1-C30) alkyl;

[0063] R 11 ~R 14 are independently hydrogen or methyl.)

[0064] As an example, the R1 may be a (C4-C30) alkyl group.

[0065] As an example, the compound may be a compound selected from the following structures, but is not limited thereto.

[0066]

[0067] One aspect of the present invention provides a curable composition comprising the compound, wherein the compound can be used as an additive of the curable composition, specifically as an anti-resin leakage additive (anti-resin leakage agent), and can be used as a single component, or two or more different compounds can be mixed and used as a mixed component.

[0068] Another aspect of the present invention provides a dual-curing adhesive composition comprising the compound and an epoxy resin. Specifically, the dual-curing adhesive composition according to one aspect includes the compound represented by Chemical Formula 1 as an anti-resin leakage agent, which not only has an excellent anti-resin leakage effect, but also has excellent thermal curing and light curing properties. In particular, according to the present invention, the curing speed is fast, and not only can light curing, thermal curing, or dual curing of these two curings be selected according to the use environment or purpose, but also a more improved bonding strength can be achieved through dual curing.

[0069] The epoxy resin can be used without limitation as long as it is a common resin, and a non-limiting example thereof may be an epoxy resin selected from novolac type epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol E type epoxy resin, biphenyl type epoxy resin, triphenylmethane type epoxy resin, and phenol aralkyl type epoxy resin, etc. In addition, it may be one or a mixture of two or more substances selected from epoxy compounds selected from triglycidyl isocyanurate, a mixture of diglycidyl terephthalate and triglycidyl trimellitate, glycidyl ester of versatic acid, 3',4'-epoxycyclohexanecarboxylic acid 3,4-epoxycyclohexylmethyl ester, ethylhexyl glycidyl ether, butyl glycidyl ether, and pentaerythritol tetraglycidyl ether, or an epoxy resin derived therefrom, but is not limited thereto.

[0070] The dual-cure adhesive composition according to one aspect may further include a multifunctional monomer. The multifunctional monomer may be a multifunctional acrylic compound or a multifunctional thiol compound.

[0071] A non-limiting example of the multifunctional acrylic compound may be one or more selected from dipentaerythritol hexa(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol tri(meth)acrylate, tri[2-(acryloyloxy)ethyl]isocyanurate, di-trimethylpropane tetra(meth)acrylate (D-Trimethylpropanetetra(meth)acrylate), dipentaerythritol penta(meth)acrylate and pentaerythritol tetra(meth)acrylate, but is not limited thereto.

[0072] An example of the multifunctional thiol compound may be one or more selected from 1,4-bis(3-mercaptobutyryloxy)butane, 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tris(3-mercaptobutyrate), pentaerythritol tetrakis(3-mercaptopropionate), dipentaerythritol hexa(3-mercaptopropionate) and tetraethylene glycol bis(3-mercaptopropionate), but is not limited thereto.

[0073] According to one aspect, the dual-curing adhesive composition may include 0.1-20wt%, 1-20wt%, 5-20wt% or 5-15wt% of the compound represented by Chemical Formula 1 (resin leakage prevention agent) relative to the total weight of the composition. In addition, relative to 100 parts by weight of the epoxy resin, 10-50 parts by weight, 10-40 parts by weight or 20-40 parts by weight of the compound represented by Chemical Formula 1 (resin leakage prevention agent) may be included. In addition, relative to 100 parts by weight of the epoxy resin, 10-50 parts by weight, 10-40 parts by weight or 20-40 parts by weight of the multifunctional monomer may be included. When the above range is met, a better anti-resin leakage effect can be achieved without causing a decrease in the physical properties of the adhesive.

[0074] In addition, the dual-cure adhesive composition according to one aspect may include one or more additives selected from a thermal curing agent, a photoinitiator, a curing catalyst, and an inorganic filler.

[0075] The photoinitiator may be used without limitation as long as it is a common initiator. Non-limiting examples thereof include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether, acetophenone, hydroxydimethylacetophenone, dimethylaminoacetophenone, dimethoxy-2-phenylacetophenone, 3-methylacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 4-chloroacetophenone, 4,4-dimethoxyacetophenone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, 4-hydroxycyclophenyl ketone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-(4-methylthiophenyl)-2-morpholinyl-1-propanone, and 2-methyl-1-[4-(methylthio)phene]- 2-morpholino-propane-1-one), 4-(2-hydroxyethoxy)phenyl-2-(hydroxy-2-propyl)ketone, benzophenone, p-phenylbenzophenone, 4,4-diaminobenzophenone, 4,4'-diethylaminobenzophenone, dichlorobenzophenone, anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, 2-tert-butylanthraquinone, 2-aminoanthraquinone, β-chloroanthraquinone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, benzyl dimethyl ketal, diphenyl ketone benzyl dimethyl ketal, acetophenone dimethyl ketal, p-dimethylaminobenzoate, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, fluorene, triphenylamine, carbazole, benzyl diphenyl sulfide and tetramethylthiuram monosulfide, and a mixture of one or more substances selected therefrom can be used. In addition, as commercially available products, resins with trade names such as Darocur 1173, Igacure 184, and Igacure 907 (from Ciba) can be used. These products can be used alone or in combination of two or more. The photoinitiator can be contained in an amount of 0.01 to 5 wt%, 0.05 to 3 wt%, or 0.1 to 2 wt%, based on the total weight of the dual-curing adhesive composition.

[0076] The thermosetting agent may be a latent thermosetting agent that does not initiate thermosetting below the target temperature (normal temperature, 25° C.). As a non-limiting example, imidazole thermosetting agents, dihydrazide thermosetting agents or amine thermosetting agents may be used, but amine thermosetting agents are preferably used in view of the curing time, storage stability, and improvement of bonding strength. In addition, as a commercially available product, PN-23 of AJINOMOTO FINE TECHNO Co., Ltd. may be used.

[0077] The inorganic filler can be used without limitation as long as it is a common filler. As a non-limiting example, silicon dioxide, diatomaceous earth, aluminum oxide, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, magnesium hydroxide, aluminum hydroxide, magnesium carbonate, barium sulfate, gypsum, calcium silicate, talc, glass beads, kaolin, talcum clay, bentonite, aluminum nitride, silicon nitride, potassium titanate, zeolite, calcium oxide, magnesium oxide and ferrite can be listed, and a mixture of one or more selected from them can be used. Wherein, based on the total weight of the dual-cure adhesive composition, the inorganic filler can be included in an amount of 10 to 40 wt%, 15 to 40 wt% or 25 to 40 wt%.

[0078] The dual-cure adhesive composition according to one aspect may be a one-component type and may be effectively used as a structural adhesive.

[0079] The anti-resin leakage effect of the dual-curing adhesive composition according to one aspect is very excellent, and excellent adhesion and reliability can be achieved after curing. In addition, excellent moisture resistance can also be exhibited under high temperature and humidity conditions. Therefore, the cured product according to one aspect can be effectively applied as an adhesive, a sealant, a coating agent, etc. Specifically, it can be effectively applied as an adhesive layer between components of camera modules, etc., which require higher bonding strength per unit area and water resistance, and can also be used as a structural adhesive in the assembly of structures such as civil engineering and construction and transportation devices such as automobiles, aircraft, and ships. This can be used in various industries to achieve excellent bonding performance between the same or different materials such as metal and metal, metal and glass, and metal and carbon fiber.

[0080] In addition, one aspect of the present invention provides a structure including the cured product. Specifically, the structure according to one aspect may include a first adherend, a second adherend, and an adhesive layer disposed between the first adherend and the second adherend, and the adhesive layer may be the cured product.

[0081] As an example, the first adherend and the second adherend may be components made of aluminum, brass, or polycarbonate, etc. Specifically, the first adherend and the second adherend may be objects selected from lenses, lens frames, and housings, etc., and a part or all of the first adherend and the second adherend may be bonded with a high bonding strength by the above-mentioned adhesive layer to form a high-quality structure.

[0082] Specifically, the structure according to one aspect may be a camera module. As an example, the structure may be a camera module mounted on a portable device such as a smartphone or a camera module for vehicle mounting.

[0083] The above implementation examples are described in more detail below through embodiments. However, the following embodiments are only used for illustration and do not limit the scope of the present invention.

[0084] <Preparation of resin leakage prevention agent>

[0085]

[0086] [Example 1]

[0087] In a 1L double-tube reactor, 54.5g of pentaerythritoltetrakis(3-mercaptobutylate) (KarenzMT PE1) and 0.5L of ethyl acetate were added, and stirred at room temperature for 10 minutes under a nitrogen flow. Then, 14.2g of butyl methacrylate (BMA) was added, and after further stirring at room temperature for 10 minutes, 0.1g of triethylamine (TEA) was added, and stirred for 12 hours. The reaction was terminated after confirming the disappearance of the acrylate peak by IR. All used solvents were removed by a rotary evaporator to prepare the anti-resin leakage agent A-1 (yield 99%) of Example 1 in which R1 = butyl (n-butyl, *-C4H9). By 1 The synthesized substances were identified by H NMR.

[0088] 1 H NMR (500MHz, CDCl3) δ4.32 (s, 2H), 4.24 (s, 6H), 4.10 (t, J = 4.6Hz, 2H), 3.59-3.48 ( m,1H),3.44-3.35(m,1H),3.29(h,J=6.5Hz,3H),3.20(dd,J=12.5,3.1Hz,1H),2.86 (dd,J=12.4,6.7Hz,3H),2.83-2.77(m,2H),2.61-2.47(m,4H),1.65-1.56(m,2H), 1.53(d,J=6.4Hz,9H),1.44-1.35(m,2H),1.36-1.31(m,9H),0.99(t,J=6.6Hz,3H).

[0089] [Example 2]

[0090] The same method as in Example 1 was used to prepare R1=octyl (*-C8H 17) of Example 2 of the resin leakage prevention agent A-2.

[0091] 1 H NMR (500MHz, CDCl3) δ4.32 (s, 2H), 4.24 (s, 6H), 4.11 (t, J = 4.9Hz, 2H), 3.65-3.44 (m, 1H), 3. 39(qt,J=6.4,3.1Hz,1H),3.29(dd,J=12.8,6.4Hz,3H),3.15(dd,J=12.3,3.1Hz,1H),2.96-2 .84(m,4H),2.81(dd,J=12.4,5.6Hz,1H),2.55(ddd,J=12.3,9.9,6.1Hz,4H),1.60(tt,J=8. 1,4.9Hz,2H),1.54(d,J=6.2Hz,9H),1.42(s,3H),1.41-1.25(m,16H),0.99(t,J=6.4Hz,3H).

[0092] [Example 3]

[0093] The same method as in Example 1 was used except that dodecyl acrylate was used instead of butyl acrylate to prepare 12 H 25 ) of Example 3 of the resin leakage prevention agent A-3.

[0094] 1 H NMR (500MHz, CDCl3) δ4.31(s,2H),4.24(s,6H),4.21-4.13(m,1H),4.04(t,J=7.5Hz,2H),3.40-3.23(m,4H),3.02(dd,J=12.5,3.3Hz,1H),2.9 0-2.76(m,5H),2.54(ddd,J=17.3,12.4,7.0Hz,4H),1.64(p,J=7.7Hz,2H),1.51(d,J=6.5Hz,12H),1.45-1.14(m,24H),0.99(t,J=6.4Hz,3H).

[0095] [Example 4]

[0096] The same method as in Example 1 was used to prepare R1 = octadecyl (*-C 18 H 37 ) of Example 4 of the resin leakage prevention agent A-4.

[0097] 1 H NMR (500MHz, CDCl3) δ4.35(s,2H),4.29(s,6H),4.05(t,J=7.5Hz,2H),3.62-3.51(m,1H),3.35-3.22(m,4H),3.02(ddd,J=17.6,12.4,7.3Hz, 2H), 2.83 (ddd, J=15.1, 12.3, 7.1Hz, 4H), 2.52 (ddd, J=34.6, 12.4, 6.6Hz, 4H), 1.61-1.48 (m, 12H), 1.44-1.24 (m, 38H), 0.99 (t, J=6.4Hz, 3H).

[0098] [Example 5]

[0099] The same method as in Example 1 was used except that behenyl acrylate was used instead of butyl acrylate to prepare R1=behenyl, *-C 22 H 45 ) of Example 4 of the present invention.

[0100] 1 H NMR (500MHz, CDCl3) δ4.28 (s, 2H), 4.24 (s, 6H), 4.07 (t, J = 7.5Hz, 2H), 3.57-3.45 (m, 1H),3.39-3.23(m,4H),3.03(dd,J=12.4,3.0Hz,1H),2.86(ddd,J=12.5,8.6,7.0Hz,4 H),2.69(dd,J=12.4,3.0Hz,1H),2.53(dt,J=12.5,7.5Hz,4H),1.63(tt,J=7.5,5.6H z, 2H), 1.54 (s, 3H), 1.48 (d, J = 6.2Hz, 9H), 1.42-1.20 (m, 44H), 0.99 (t, J = 6.4Hz, 3H).

[0101] <Preparation of Dual-Cure Adhesive Composition>

[0102] [Example 6 to Example 10]

[0103] A dual-cure adhesive composition (100 g) was prepared according to the components and contents described in Table 1 below.

[0104] [Comparative Example 1]

[0105] As shown in Table 1 below, a dual-curing adhesive composition was prepared in the same manner as in Example 6 except that pentaerythritol tetrakis(3-mercaptobutylate) (C-1) was used instead of the resin leakage preventer A-1 obtained in Example.

[0106] [Comparative Example 2]

[0107] As shown in Table 1 below, a dual-curing adhesive composition was prepared in the same manner as in Example 6, except that pentaerythritol tetrakis(3-mercaptobutylate) (C-1) and dodecyl acrylate (C-2) were used to replace the resin leakage prevention agent A-1 obtained in the example.

[0108] [Table 1]

[0109]

[0110]

[0111] <Evaluation Example>

[0112] Evaluation 1: Anti-resin leakage effect

[0113] After the substrate made of polyimide was plasma treated (200 W, N2, five minutes), the dual-curing adhesive composition prepared in the examples and comparative examples was coated with a radius of 0.5 mm and left at 25° C. for one hour, then moved to a hot plate set at 80° C. and cured for 150 seconds. The difference between the radius (R0) of the adhesive initially coated and the radius (R1) of the adhesive flowing out after final curing was calculated to calculate RBO (R1-R0) (see Figure 1 ). The results are recorded in Table 2 below.

[0114] Evaluation 2: Adhesion evaluation

[0115] The dual-curing adhesive composition of the embodiment and the comparative example was dispensed (dispensing amount: 80 mg) on ​​the interface of the aluminum first adherend with an inner diameter of 13.5 mm and an outer diameter of 15.5 mm. Then, it was bonded to the aluminum second adherend to prepare a small cell (see Figure 2 At this time, the interval between the first adherend and the second adherend was set to 300 μm. Then, for the prepared small compartment, four light sources (1,000 mW / cm 2, 7s) after the first curing by LED 365nm wavelength ultraviolet light, the second curing was carried out by heating in a convection oven at 80°C for one hour.

[0116] Then, the adhesion of the small cells that have been cured was measured using UTM, and the tensile speed was set to 30 mm / min. The results are recorded in Table 2 below.

[0117] Evaluation 3: Reliability evaluation

[0118] Constant temperature / humidity

[0119] The cured cells were exposed to an environment maintained at 85°C and 85% RH for 500 hours using a constant temperature and humidity machine, and the adhesive force was measured. The constant temperature and humidity reliability was evaluated according to the following criteria, and the results are recorded in Table 2 below.

[0120] X: The adhesive force is reduced by 20% or more compared to the small cell before the reliability evaluation.

[0121] O: The adhesive force was reduced by an amount less than 20% compared with the small cell before the reliability evaluation.

[0122] Thermal shock

[0123] The cured cells were kept at -40°C for 30 minutes and at 85°C for 30 minutes as one cycle, and the adhesion after 500 cycles was measured. The thermal shock reliability was evaluated according to the following criteria and the results are recorded in Table 2 below.

[0124] X: The adhesive force is reduced by 20% or more compared to the small cell before the reliability evaluation.

[0125] O: The adhesive force was reduced by an amount less than 20% compared with the small cell before the reliability evaluation.

[0126] Evaluation 4: Storage stability

[0127] The dual-cure adhesive compositions of the examples and comparative examples were stored in a sealed plastic container at 25° C. for 72 hours, and the viscosity before and after storage was measured. The storage stability was evaluated according to the following criteria, and the results are recorded in Table 2 below.

[0128] X: The viscosity increased by 20% or more compared to the initial viscosity.

[0129] O: The viscosity increased by less than 20% compared to the initial viscosity.

[0130] [Table 2]

[0131]

[0132] As shown in Table 2 above, it was confirmed that the dual-curing adhesive compositions of the embodiments of the present invention all maintained excellent adhesion and reliability while having an excellent anti-resin leakage effect. On the contrary, it was confirmed that the comparative examples not containing the anti-resin leakage agent according to one aspect basically failed to achieve the anti-resin leakage effect, and in particular, the comparative example 3 in which pentaerythritol tetrakis (3-mercaptobutyrate) and dodecyl acrylate used in the synthesis of the anti-resin leakage agent of the present invention were added as components also basically failed to achieve the anti-resin leakage effect.

[0133] That is, the dual-curing adhesive composition according to one aspect has an excellent effect of preventing resin leakage, and can achieve a more improved adhesive force through dual curing. By achieving such physical properties, it is expected that it can be effectively used as an adhesive layer between components of camera modules that require high adhesive strength per unit area and water resistance and are miniaturized and thinned.

[0134] The embodiments of the present invention are described in more detail above with reference to the accompanying drawings, but the present invention is not necessarily limited to these embodiments, and various modifications can be made within the scope of the technical concept of the present invention. Therefore, the embodiments disclosed in the present invention are not used to limit the technical concept of the present invention, but are used for illustration, and the scope of the technical concept of the present invention is not limited by these embodiments. The protection scope of the present invention shall be interpreted by the claims, and all technical concepts within the scope equivalent to the content of the claims shall be interpreted as included in the scope of rights of the present invention.

Claims

1. A compound represented by the following chemical formula 1, [Chemical formula 1] In the chemical formula 1, R is (C1-C30) alkyl, R1 and R2 are each independently (C1-C30) alkyl; L1 to L7 are each independently (C1-C7) alkylene.

2. The compound according to claim 1, which is represented by the following Chemical Formula 2: [Chemical formula 2] In the chemical formula 2, R1 is (C1-C30) alkyl; L1 to L5 are each independently (C1-C7) alkylene.

3. The compound according to claim 1, which is represented by the following Chemical Formula 3: [Chemical formula 3] In the chemical formula 3, R1 is (C1-C30) alkyl; R 11 ~R 14 are each independently hydrogen or methyl. 4 . A resin leakage preventer comprising a compound selected from any one of claims 1 to 3. 5 . A dual-curing adhesive composition comprising the resin leakage prevention agent according to claim 4 and an epoxy resin. The dual-cure adhesive composition according to claim 5 , further comprising a multifunctional monomer.

7. The dual-curing adhesive composition according to claim 6, wherein: The multifunctional monomer is a multifunctional acrylic compound.

8. The dual-curing adhesive composition according to claim 5, wherein The invention further comprises 10 to 40 parts by weight of a resin leakage preventing agent based on 100 parts by weight of the epoxy resin. 9 . The dual-curing adhesive composition according to claim 5 , further comprising one or more additives selected from the group consisting of a thermal curing agent, a photoinitiator, a curing catalyst and an inorganic filler.

10. A cured product prepared from the dual-curing adhesive composition according to claim 5.

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