Epoxy compound, composition, and cured product thereof

Abstract

The present disclosure provides an epoxy compound, a composition, and a cured product thereof. The epoxy compound has a structure shown in formula (I) wherein R 1 and R 2 Each is independently cyano, isocyanate, oxiranyl, methyloxiranyl, glycidyl, methylglycidyl, glycidoxy, oxetanyl, oxetanylmethyl, or C 1‑10 Alkoxy; Z is ‑O‑, R 3 and R 4 each is independently hydrogen, fluorine, methyl, fluoromethyl, or ethyl; n and m are each independently 3, 4, 5, 6, 7, 8, 9, or 10; and i and j are each independently 1, 2, or 3.

Description

Technical Field

[0001] The present disclosure relates to an epoxy compound, a composition, and a cured product thereof. Background Art

[0002] Epoxy resin is widely used in optoelectronic and semiconductor components. Due to its excellent mechanical properties and good heat resistance, it is one of the preferred insulating materials. Due to the rapid development of high-voltage and high-power modules, excessive heat accumulation will accelerate the aging of epoxy resin, destroy the internal basic structure and affect its stability, resulting in a shortened service life of devices containing epoxy resin.

[0003] In order to improve the thermal conductivity of a composition containing a conventional low thermal conductivity epoxy resin, a high content of thermally conductive powder is generally mixed with the conventional epoxy resin to serve as a high thermal conductivity packaging material. However, the addition of thermally conductive powder will affect the fluidity of the resulting composition and the mechanical properties of the resulting packaging material, so that the amount of thermally conductive powder added is limited and the characteristic requirements of a high thermal conductivity module cannot be met.

[0004] Epoxy resins with mesogen structures have been used in epoxy resin compositions to form insulating materials with high thermal conductivity due to their excellent thermal conductivity. However, conventional epoxy resins with mesogen structures have a relatively high melting point (greater than 120°C) and are also highly viscous in a high-temperature molten state. Therefore, when melt-blended with a curing agent and a filler, it is difficult to disperse evenly and cannot be used in solvent-free liquid packaging materials.

[0005] In summary, there is an urgent need for novel epoxy resin compositions to solve the problems encountered in the prior art. Summary of the invention

[0006] According to an embodiment of the present disclosure, the present disclosure provides an epoxy compound. The epoxy compound has a structure shown in formula (I):

[0007]

[0008] Formula (I),

[0009] Where R 1 and R 2Each of them is independently a cyano group, an isocyanate group, an oxiranyl group, a methyloxiranyl group, a glycidyl group, a methylglycidyl group, an epoxypropoxy group, an oxetanyl group, an oxetanemethyl group, or C 1-10 Alkoxy; Z is -O-, R 3 and R 4 each is independently hydrogen, fluorine, methyl, fluoromethyl, or ethyl; n and m are each independently 3, 4, 5, 6, 7, 8, 9, or 10; and i and j are each independently 1, 2, or 3.

[0010] According to an embodiment of the present disclosure, the present disclosure provides a composition, which comprises the epoxy compound described in the present disclosure and a curing agent, wherein the weight ratio of the epoxy compound to the curing agent is 1:9 to 9:1.

[0011] According to an embodiment of the present disclosure, the present disclosure also provides a cured product, which is a cured product of the composition described in the present disclosure. DETAILED DESCRIPTION

[0012] The following is a detailed description of the epoxy compounds, compositions and cured products described in the present disclosure. It should be understood that the following description provides many different embodiments or examples for implementing different embodiments of the present disclosure. The specific components and arrangements described below are only briefly described in the present disclosure. Of course, these are only used as examples and are not limitations of the present disclosure. In the present disclosure, the word "about" means that the specified amount can be increased or decreased by an amount that can be recognized as a general and reasonable size by those skilled in the art.

[0013] The present disclosure provides an epoxy compound. The epoxy compound described in the present disclosure, by introducing a group having a mesogen structure in the side chain, can utilize the π-π stacking effect of the aromatic ring to promote the orderly arrangement of the microstructure when the epoxy compound reacts with the curing agent, resulting in the obtained cured product having a crystal-like structure, thereby increasing its thermal conductivity. In addition, the epoxy compound described in the present disclosure, by introducing an aliphatic chain segment to regulate the physical properties of the epoxy compound and reduce the melting point of the epoxy compound, can make the epoxy compound described in the present disclosure have a lower viscosity under heating (less than 90°C). In this way, by virtue of the good fluidity of the epoxy compound, the epoxy compound described in the present disclosure can be further combined with a curing agent to form a composition, which can be applied to solvent-free liquid packaging materials.

[0014] According to the embodiments of the present disclosure, the epoxy compound described in the present disclosure may have a structure shown in formula (I):

[0015]

[0016] Where R 1 and R 2 Each of the groups may be independently a cyano group, an isocyanate group, an oxiranyl group, a methyloxiranyl group, a glycidyl group, a methylglycidyl group, an epoxypropoxy group, an oxetanyl group, an oxetanemethyl group, or a C 1-10 Alkoxy; Z can be -O-, R 3 and R 4 may each independently be hydrogen, fluorine, methyl, fluoromethyl, or ethyl; n and m may each independently be 3, 4, 5, 6, 7, 8, 9, or 10; and i and j may each independently be 1, 2, or 3.

[0017] According to an embodiment of the present disclosure, the epoxy compound may be

[0018]

[0019]

[0020] Where R1 and R 2 Each of the groups may be independently a cyano group, an isocyanate group, an oxiranyl group, a methyloxiranyl group, a glycidyl group, a methylglycidyl group, an epoxypropoxy group, an oxetanyl group, an oxetanemethyl group, or a C 1-10 alkoxy; n and m may each independently be 3, 4, 5, 6, 7, 8, 9, or 10; and i and j may each independently be 1, 2, or 3.

[0021] According to an embodiment of the present disclosure, C 1-10 The alkoxy group may be a linear or branched alkoxy group. 1-10 The alkoxy group may be methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, or an isomer thereof.

[0022] According to the embodiments of the present disclosure, when n and m are independently 1 or 2, the obtained epoxy compound has a shorter aliphatic chain in the molecule. Therefore, the obtained epoxy compound tends to have a higher melting point (greater than 90° C.) than the epoxy compound when n and m are independently 3, and has high viscosity even in the molten state. As a result, due to the poor fluidity, the composition containing the epoxy compound needs to be further combined with a solvent to meet the processability requirements, and therefore cannot be applied to solvent-free liquid packaging materials.

[0023] According to an embodiment of the present disclosure, the epoxy compound may be

[0024] Where R 1 and R 2Each of the groups may be independently a cyano group, an isocyanate group, an oxiranyl group, a methyloxiranyl group, a glycidyl group, a methylglycidyl group, an epoxypropoxy group, an oxetanyl group, an oxetanemethyl group, or a C 1-10 Alkoxy; Z can be -O-, R 3 and R 4 may each independently be hydrogen, fluorine, methyl, fluoromethyl, or ethyl; and n and m may each independently be 3, 4, 5, 6, 7, 8, 9, or 10.

[0025] According to an embodiment of the present disclosure, the epoxy compound may be

[0026]

[0027]

[0028]

[0029]

[0030] Wherein Z can be -O-, R 3 and R 4 may each independently be hydrogen, fluorine, methyl, fluoromethyl, or ethyl; and n and m may each independently be 3, 4, 5, 6, 7, 8, 9, or 10.

[0031] According to an embodiment of the present disclosure, the epoxy compound may be

[0032]

[0033]

[0034] Where R 1 and R 2Each of the groups may be independently a cyano group, an isocyanate group, an oxiranyl group, a methyloxiranyl group, a glycidyl group, a methylglycidyl group, an epoxypropoxy group, an oxetanyl group, an oxetanemethyl group, or a C 1-10 Alkoxy; Z can be -O-, R 3 and R 4 may each independently be hydrogen, fluorine, methyl, fluoromethyl, or ethyl; and i and j may each independently be 1, 2, or 3.

[0035] According to an embodiment of the present disclosure, the present disclosure also provides a composition (e.g., a composition not containing a solvent) having good processability and suitable for use as a liquid packaging material composition in the packaging of semiconductor components. According to an embodiment of the present disclosure, the composition described in the present disclosure may include an epoxy compound having a structure shown in formula (I) and a curing agent described in the present disclosure. According to an embodiment of the present disclosure, the ratio of the number of epoxy equivalents of the epoxy compound to the number of moles of the curing agent may be 1:0.7 to 1:1.3, so that the epoxy compound having a structure shown in formula (I) can fully react with the curing agent. According to an embodiment of the present disclosure, the weight ratio of the epoxy compound to the curing agent may be about 1:9 to 9:1 (e.g., about 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, or 8:1).

[0036] According to an embodiment of the present disclosure, the curing agent may be an isocyanate curing agent, a diamine curing agent, an anhydride curing agent, a phenol curing agent, an organic phosphonium curing agent, a thiol curing agent, or a combination thereof.

[0037] According to an embodiment of the present disclosure, the isocyanate curing agent may be an isocyanate curing agent known in the art for epoxy resin compositions, such as toluenediisocyanate (TDI), phenylene diisocyanate, 4,4'-diphenyl diisocyanate (4,4'-diphenyl diisocyanate), 1,5-naphthalene diisocyanate (naphthalene diisocyanate, NDI), diphenylmethane diisocyanate (diphenylmethane diisocyanate, MDI), toluidine diisocyanate (toluidine diisocyanate, TODI), 4,4'-diphenyl ether diisocyanate (4,4'-diphenyl ether diisocyanate), xylylene diisocyanate (xylylene diisocyanate, XDI), tetramethyl xylylene diisocyanate (tetramethyl xylylene diisocyanate, diisocyanate, TMXDI), ω,ω′-diisocyanate-1,4-diethylbenzene, trimethylene diisocyanate, 1,2-propylene diisocyanate, butylene diisocyanate, pentamethylene diisocyanate (pentamethylene diisocyanate, PDI), hexamethylene diisocyanate (hexamethylene diisocyanate, HDI), trimethylhexamethylene diisocyanate, 2,6-diisocyanate methyl caprate, 1,3-cyclopentane diisocyanate, 1,3-cyclopentene diisocyanate ...ane diisocyanate, 1,3-cyclopentene diisocyanate, 1,3-cyclopentane diisocyanate, 1,3-cyclopentane diisocyanate, 1,3-cyclopentene diisocyanate, 1,3-cyclopentane diisocyanate, 1,3-cyclopentane diisocyanate, 1,3-cyclopentene diisocyanate, 1,3-cyclopentane diisocyanate, 1,3-cyclopentane diisocyanate, 1,3-cyclopentene diisocyanate,3-cyclopentene diisocyanate), cyclohexane diisocyanate (cyclohexane diisocyanate), isophorone diisocyanate (IPDI), methylene bis (cyclohexyl isocyanate) (H12MDI), methyl cyclohexane diisocyanate (methyl cyclohexane diisocyanate), norbornane diisocyanate (NBDI), bis (isocyanatomethyl) cyclohexane (bis (isocyanatomethyl) cyclohexane, H6XDI), or a combination thereof.

[0038] According to an embodiment of the present disclosure, the diamine curing agent may be a diamine curing agent known in the art for epoxy resin compositions. According to an embodiment of the present disclosure, the diamine curing agent may have two primary amine groups. According to an embodiment of the present disclosure, the diamine curing agent may be diaminodiphenylmethane, diaminodiphenyl sulfone, diaminodiphenyl ether, or diaminodiphenyl ether. ether), p-phenylenediamine, m-phenylenediamine, o-phenylenediamine, 1,3-cyclohexanebis(methylamine), 4,4'-diaminodicyclohexylmethane, 4,4'-methylenebis(2-methylcyclohexylamine), 4,4'-methylenebis(2-methylcyclohexylamine), methylaniline), 4,4′-methylenebis(2-ethylaniline), 1,5-diaminonaphthalene, m-xylylenediamine, ethylenediamine, diaminopropane, diaminobutane, pentamethylenediamine, hexamethylenediamine, isophoronediamine, polyether diamine, dicyandiamide, or a combination thereof.

[0039] According to an embodiment of the present disclosure, when the composition of the present disclosure comprises the epoxy compound of the present disclosure and the diamine curing agent, the cured product of the composition has good thermal conductivity.

[0040] According to an embodiment of the present disclosure, the anhydride curing agent may be an anhydride curing agent known in the art for epoxy resin compositions, such as phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic acid anhydride, ethylene glycol trimellitic anhydride, biphenyl tetracarboxylic acid anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, nadic anhydride, himic anhydride, or a combination thereof.

[0041] According to an embodiment of the present disclosure, the phenol curing agent may be a phenol curing agent known in the art for epoxy resin compositions, such as bisphenol A, bisphenol F, bisphenol S, 4,4′-biphenylphenol, tetramethyl bisphenol A, dimethyl bisphenol A, tetramethyl bisphenol F, dimethyl bisphenol F, tetramethyl bisphenol S, dimethyl bisphenol S ... A, dimethyl bisphenol A, dimethyl bisphenol F, dimethyl bisphenol F, dimethyl bisphenol F, dimethyl bisphenol S, dimethyl bisphenol S, dimethyl bisphenol S, dimethyl bisphenol S, dimethyl bisphenol S, dimethyl bisphenol S, dimethyl bisphenol S, dimethyl bisphenol S, dimethyl bisphenol S, dimethyl bis S), tetramethyl-4,4'-biphenol, dimethyl-4,4'-biphenylphenol, 1-(4-hydroxyphenyl)-2-[4-(1,1-bis-(4-hydroxyphenyl)ethyl)phenyl]propane, 2,2'-methylene-bis(4-methyl-6-tert-butyl)phenol phenol) (2,2′-methylene-bis(4-methyl-6-tert-butylphenol)), 4,4′-butylidene-bis(3-methyl-6-tert-butylphenol)), trishydroxyphenylmethane, resorcinol, hydroquinone, pyrogallol, or a combination thereof.

[0042] According to an embodiment of the present disclosure, the organic phosphonium curing agent may be an organic phosphonium curing agent known in the art for epoxy resin compositions, such as tetraphenylphosphonium tetra-p-tolylborate, tetraphenylphosphonium tetraphenylborate, or a combination thereof.

[0043] According to an embodiment of the present disclosure, the thiol curing agent may be a thiol curing agent known in the art for epoxy resin compositions, such as pentaerythritol tetrakis(3-mercaptobutyrate), trimethylolpropane tris(3-mercaptopropionate), 1,3,4-thiadiazole-2,5-dithiol (1,3,4-thiadiazole-2,5-dithiol, (polyethylene glycol) dithiol), toluene dithiol, benzene dithiol, 1,2-ethanedithiol, tris[2-(3-mercaptopropionyloxy)ethyl]isocyanurate, or a combination thereof.

[0044] According to an embodiment of the present disclosure, if an initiator (eg, a photoinitiator, a thermal initiator, or a combination thereof) is used to replace the curing agent described in the present disclosure, the cured product of the resulting composition will have poor thermal conductivity.

[0045] According to an embodiment of the present disclosure, the composition may further include an epoxy resin, wherein the weight ratio of the epoxy resin to the epoxy compound may be 1:9 to 9:1 (e.g., about 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, or 8:1). According to an embodiment of the present disclosure, by adding the epoxy resin, the reactivity or viscosity of the composition can be adjusted, thereby increasing the processability of the resulting composition. According to an embodiment of the present disclosure, the composition described in the present disclosure may include the epoxy compound described in the present disclosure, a curing agent, and an epoxy resin. According to an embodiment of the present disclosure, the amount of the curing agent is not limited, and those with ordinary knowledge in the art can adjust it according to actual needs so that the epoxy compound and epoxy resin described in the present disclosure can fully react with the curing agent. According to an embodiment of the present disclosure, the composition described in the present disclosure may be composed of the epoxy compound described in the present disclosure, a curing agent, and an epoxy resin.

[0046] According to an embodiment of the present disclosure, the epoxy resin may be bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, novolac epoxy resin, naphthalene epoxy resin, anthracene epoxy resin, bisphenol A diglycidyl ether epoxy resin, ethylene glycol diglycidyl ether epoxy resin, propylene glycol diglycidyl ether epoxy resin, 1,4-butanediol diglycidyl ether epoxy resin, biphenyl epoxy resin, cyclopentadiene epoxy resin, or a combination thereof.

[0047] According to an embodiment of the present disclosure, the composition of the present disclosure may further include an additive. The additive may be a known additive in a resin composition (e.g., an epoxy resin composition), such as a leveling agent, a filler, a colorant, a dye, a defoamer, a flame retardant, a viscosity modifier, a thixotropic agent, a dispersant, a stabilizer, or a combination thereof. According to an embodiment of the present disclosure, the amount of the additive added is not particularly limited, and may be about 0.1 wt % to 30 wt % (e.g., about 0.2 wt %, 0.5 wt %, 0.8 wt %, 1 wt %, 1.5 wt %, 2 wt %, 2.5 wt %, 3 wt %, 4 wt %, 5 wt %, 6 wt %, 7 wt %, 8 wt %, 9 wt %, 10 wt %, 11 wt %, 12 wt %, 13 wt %, 14 wt %, 15 wt %, 16 wt %, 17 wt %, 18 wt %, 19 wt %, 20 wt %, 25 wt %, or 28 wt %), based on the total weight of the epoxy compound and the curing agent.

[0048] According to the embodiments of the present disclosure, since the epoxy compound used has fluidity at low temperatures (eg, 25° C. to 90° C.), the composition of the present disclosure does not contain a solvent when used as a packaging material composition and can be directly used in a packaging process.

[0049] According to an embodiment of the present disclosure, the present disclosure also provides a cured product of the composition described in the present disclosure. According to an embodiment of the present disclosure, the cured product may be a product obtained after the composition described in the present disclosure undergoes a curing process.

[0050] The preparation method of the cured product described in the present disclosure may include the following steps. First, the composition described in the present disclosure is provided. Then, the composition is filled into a mold. Then, the filled mold is subjected to a curing process to obtain the cured product. The temperature of the curing process may be about 80° C. to 200° C., and the time of the curing process may be 30 minutes to 8 hours. In addition, the curing process may include multiple heating stages.

[0051] In order to make the above contents and other purposes, features, and advantages of the present disclosure more obvious and understandable, preferred embodiments are given and described in detail as follows.

[0052] Epoxides

[0053] Table 1 lists the epoxy compounds having the structure shown in formula (I) obtained in the examples of the present disclosure, and their respective chemical structures are listed in detail in the table.

[0054] Table 1

[0055]

[0056]

[0057] To further illustrate the epoxy compounds described in the present disclosure, the preparation process of the epoxy compounds described in Examples 1-3 is listed below.

[0058] Example 1: Epoxy compound (1)

[0059] 1,6-dibromohexane (86.5g), NaOH (10g), and acetone (400ml) are placed in a reaction flask. Next, 6-cyano-2-naphthol (20g) is dissolved in acetone (100ml) to obtain a 6-cyano-2-naphthol solution. Next, the 6-cyano-2-naphthol solution is slowly dripped into the reaction flask (the dripping is completed within 3 hours). After reacting at 25°C for 8 hours, the resultant is filtered and the filtrate is collected. After the obtained filtrate is concentrated, the resultant is dripped into methanol, and a precipitate can be observed. The precipitate is collected and dried to obtain compound (1) (white solid). The reaction formula of the above reaction is as follows:

[0060]

[0061] Compound (1) was analyzed by nuclear magnetic resonance spectroscopy, and the obtained spectral information was as follows: 1 H-NMR (500MHz, CDCl3): δ1.50~2.00(m,4H),1.80~2.00(m,4H),3.43(br.t,2H),4.10(b r.t,2H),7.15(s,1H),7.20~6.25(m,1H),7.58(b,1H),7.75~7.80(m,2H),8.15(s,1H).

[0062] 2,2'-diallylbisphenol A (8.46 g) and acetone (600 ml) were added to the reaction flask. Then, sodium hydroxide (NaOH) (10 g) was added to the reaction flask. After stirring for half an hour, compound (1) (15.5 g) was added to the reaction flask and reacted at 25°C. The conversion rate of compound (1) was monitored by nuclear magnetic resonance spectroscopy (NMR), and the reaction was terminated when the conversion rate reached 97% or more. Then, the resultant was filtered and the filtrate was collected. After the filtrate was concentrated, the resultant was added to dichloromethane, extracted three times with water, and the organic layer was collected. Then, the organic layer was dehydrated with magnesium sulfate and concentrated to obtain compound (2) (viscous liquid). The reaction formula of the above reaction is as follows:

[0063]

[0064] Compound (2) was analyzed by nuclear magnetic resonance spectroscopy, and the obtained spectral information was as follows: 1 H-NMR (500MHz, CDCl3): δ1.50~1.70(m,14H),1.80~2.00(m,8H),3.33(br.d,4H),3.95(br.t,4H),4.10(br.t,4H),4.95~5.05(m,4H),5. 85~6.00(m,2H),6.70~7.80(m,2H),6.95~7.05(m,4H),7.15(s,2H),7.20~6.25(m,2H),7.58(br.d,2H),7.75~7.80(m,4H),8.15(s,2H).

[0065] Compound (2) (17 g) and dichloromethane (100 g) are added to a reaction flask. 3-chloroperoxybenzoic acid (m-CPBA) (70%, 20 g) is slowly added to the reaction flask at 0°C. Then, stirring is continued at 25°C, and the conversion rate of compound (2) is monitored by nuclear magnetic resonance spectroscopy (NMR), and the reaction is terminated when the conversion rate reaches more than 97%. Saturated sodium bicarbonate (NaHCO3) aqueous solution (100 ml) is added to the reaction flask, the organic layer is collected and extracted three times with water. Then, the organic layer is dehydrated with magnesium sulfate and concentrated to obtain the epoxy compound (1) (brown product). The reaction formula of the above reaction is as follows:

[0066]

[0067] The epoxide compound (1) was analyzed by nuclear magnetic resonance spectroscopy, and the obtained spectral information was as follows: 1H-NMR (500MHz, CDCl3): δ1.50~1.70(m,14H),1.80~2.00(m,8H),2.50~2.55(m,2H),2.60~2.80(m,4H),2.85~3.00(m,2H),3.15(br.s,2H),3.95(b r.t,4H),4.10(br.t,4H),6.70~7.80(m,2H),6.95~7.05(m,4H),7.15(s, 2H),7.20~6.25(m,2H),7.58(br.d,2H),7.75~7.80(m,4H),8.15(s,2H).

[0068] The viscosity of the epoxy compound (1) was analyzed, and the viscosity of the epoxy compound (1) was measured to be 26.4 Pa.s at 50° C. and 2.54 Pa.s at 90° C. The viscosity was measured using a high shear rate viscometer (Brookfield CAP2000 H).

[0069] Example 2: Epoxy Compound (2)

[0070] 1,3-dibromopropane (71.6 g), sodium hydroxide (NaOH) (10 g), and acetone (400 ml) are placed in a reaction flask. Next, 6-cyano-2-naphthol (20 g) is dissolved in acetone (100 ml) to obtain a 6-cyano-2-naphthol solution. Next, the 6-cyano-2-naphthol solution is slowly dripped into the reaction flask (the dripping is completed within 3 hours). After reacting at 25°C for 8 hours, the resultant is filtered and the filtrate is collected. After the obtained filtrate is concentrated, the resultant is dripped into methanol, and a precipitate is observed. The precipitate is collected and dried to obtain compound (3) (white solid). The reaction formula of the above reaction is as follows:

[0071]

[0072] Compound (3) was analyzed by nuclear magnetic resonance spectroscopy, and the obtained spectral information was as follows: 1 H-NMR (500MHz, CDCl3): δ2.30~2.40(m,2H),3.63(br.t,2H),4.26(br.t,2H), 7.18(s,1H),7.20~6.25(m,1H),7.58(m,1H),7.75~7.80(m,2H),8.15(s,1H).

[0073] 2,2'-diallylbisphenol A (9.72 g) and acetone (600 ml) were added to the reaction flask. Then, sodium hydroxide (NaOH) (15 g) was added to the reaction flask. After stirring for half an hour, compound (3) (16.4 g) was added to the reaction flask and reacted at 25°C. The conversion rate of compound (3) was monitored by nuclear magnetic resonance spectroscopy (NMR), and the reaction was terminated when the conversion rate reached 97% or more. Then, the resultant was filtered and the filtrate was collected. After the filtrate was concentrated, the resultant was added to dichloromethane, extracted three times with water, and the organic layer was collected. Then, the organic layer was dehydrated with magnesium sulfate and concentrated to obtain compound (4) (viscous liquid). The reaction formula of the above reaction is as follows:

[0074]

[0075] Compound (4) was analyzed by nuclear magnetic resonance spectroscopy, and the obtained spectral information was as follows: 1 H-NMR (500MHz, CDCl3): δ1.60(br.s,6H),2.30~2.40(m,4H),3.33(br.d,4H),4.18(br.t,4H),4.37(br.t,4H),4.90~5.00(m,4H),5.8 5~6.00(m,2H),6.70~7.80(m,2H),6.95~7.05(m,4H),7.18(s,2H),7.20~6.25(m,2H),7.58(br.d,2H),7.75~7.80(m,4H),8.15(s,2H).

[0076] Compound (4) (21.7 g) and dichloromethane (110 g) are added to a reaction flask. Meta-chloroperbenzoic acid (m-CPBA) (70%, 37 g) is slowly added to the reaction flask at 0°C. Then, stirring is continued at 25°C, and the conversion rate of compound (4) is monitored by nuclear magnetic resonance spectroscopy (NMR), and the reaction is terminated when the conversion rate reaches more than 97%. Saturated sodium bicarbonate (NaHCO3) aqueous solution (100 ml) is added to the reaction flask, the organic layer is collected and extracted three times with water. Then, the organic layer is dehydrated with magnesium sulfate and concentrated to obtain epoxy compound (2) (brown product). The reaction formula of the above reaction is as follows:

[0077]

[0078] The epoxide (2) was analyzed by nuclear magnetic resonance spectroscopy, and the obtained spectral information was as follows: 1H-NMR (500MHz, CDCl3): δ1.60(br.s,6H),2.30~2.40(m,4H),2.40~2.50(m,2H),2.60~3.00(m,6H),3.15(br.s,2H),4.18(br.t,4H),4 .37(br.t,4H),6.70~7.80(m,2H),6.95~7.05(m,4H),7.18(s,2H),7.20~6.25(m,2H),7.58(br.d,2H),7.75~7.80(m,4H),8.15(s,2H).

[0079] The viscosity of the epoxy compound (2) was analyzed, and the viscosity of the epoxy compound (2) at 90° C. was measured to be 18.2 Pa.s.

[0080] Example 3: Epoxy Compound (3)

[0081] 2,7-dihydroxynaphthalene (20 g), sodium hydroxide (4.7 g), and acetone (300 ml) were added to the reaction flask. Then, allyl bromide (14 g) was added to the reaction flask. After reacting at 25° C. for 8 hours, the resultant was filtered and the filtrate was collected. After the filtrate was concentrated, the resultant was dropped into dichloromethane. The resultant was filtered, the filtrate was collected and concentrated to obtain compound (5). The reaction formula of the above reaction is as follows:

[0082]

[0083] Compound (5) was analyzed by nuclear magnetic resonance spectroscopy, and the obtained spectral information was as follows: 1 H-NMR (500MHz, CDCl3): δ4.60~4.70(br.d,2H), 5.34(br.d,1H), 5.48(br.d,1H), 6.08~6.20(m,1H), 6.90~7.10(m,4H), 7.60~7.70(m,2H).

[0084] Place 1,3-dibromopropane (55g), sodium hydroxide (10g), and acetone (400ml) in a reaction flask. Then, dissolve compound (5) (15.7g) in acetone (100ml) to obtain a 6-cyano-2-naphthol solution. Then, slowly drip the 6-cyano-2-naphthol solution into the reaction flask (the dripping is completed within 3 hours). After reacting at 25°C for 8 hours, filter the resultant and collect the filtrate. After concentrating the filtrate, drip the resultant into methanol, and precipitate can be observed. Collect the precipitate and dry it to obtain compound (6). The reaction formula of the above reaction is as follows:

[0085]

[0086] Compound (6) was analyzed by nuclear magnetic resonance spectroscopy, and the obtained spectral information was as follows: 1 H-NMR (500MHz, CDCl3): δ2.30~2.45(m,2H),3.63(br.t,2H),4.20(br.t,2H),4.60~4.70(br.d, 2H),5.34(br.d,1H),5.48(br.d,1H),6.08~6.20(m,1H),6.90~7.10(m,4H),7.60~7.70(m,2H).

[0087] 2,2'-diallylbisphenol A (7.72 g) and acetone (600 ml) were added to the reaction flask. Then, sodium hydroxide (6.5 g) was added to the reaction flask. After stirring for half an hour, compound (6) (18.1 g) was added to the reaction flask and reacted at 25°C. The conversion rate of compound (6) was monitored by nuclear magnetic resonance spectroscopy (NMR), and the reaction was terminated when the conversion rate reached 97% or more. Then, the resultant was filtered and the filtrate was collected. After the filtrate was concentrated, the resultant was added to dichloromethane, extracted three times with water, and the organic layer was collected. Then, the organic layer was dehydrated with magnesium sulfate and concentrated to obtain compound (7). The reaction formula of the above reaction is as follows:

[0088]

[0089] Compound (7) was analyzed by nuclear magnetic resonance spectroscopy, and the obtained spectral information was as follows: 1H-NMR (500MHz, CDCl3): δ1.60(br.s,6H),2.30~2.40(m,4H),3.33(br.d,4H),4.18(br.t,4H),4.37(br.t,4H),4.60~4.70(br.d,4H),5.90~5 .10(m,4H),5.34(br.d,2H),5.48(br.d,2H),5.85~6.10(m,2H),6.10~ 6.20(m,2H),6.70~7.80(m,2H),6.90~7.20(m,12H),7.60~7.70(m,4H).

[0090] Compound (7) (5 g) and dichloromethane (100 g) are added to a reaction flask. Meta-chloroperbenzoic acid (m-CPBA) (70%, 12.5 g) is slowly added to the reaction flask at 0°C. Then, stirring is continued at 25°C, and the conversion rate of compound (7) is monitored by nuclear magnetic resonance spectroscopy (NMR), and the reaction is terminated when the conversion rate reaches more than 97%. Then, a saturated sodium bicarbonate aqueous solution (100 ml) is added to the reaction flask, the organic layer is collected and extracted three times with water. Then, the organic layer is dehydrated with magnesium sulfate and concentrated to obtain an epoxy compound (3) (brown product). The reaction formula of the above reaction is shown below:

[0091]

[0092] The epoxide (3) was analyzed by nuclear magnetic resonance spectroscopy, and the obtained spectral information was as follows: 1 H-NMR (500MHz, CDCl3): δ1.60 (br.s, 6H), 2.30~2.40 (m, 4H), 2.40~3.20 (m, 20H), 3.85 (br.t,4H),4.08(br.t,4H),6.70~7.80(m,2H),6.90~7.20(m,12H),7.60~7.70(m,4H).

[0093] The viscosity of the epoxy compound (3) was analyzed, and the viscosity of the epoxy compound (3) at 90° C. was measured to be 105.9 Pa.s.

[0094] It can be seen from Examples 1-3 that the epoxy compound described in the present disclosure has a relatively low viscosity at 90° C., and thus has good fluidity.

[0095] Composition

[0096] Embodiment 11

[0097] 8.46 parts by weight of bisphenol F epoxy resin (product number EXA-830LVP, manufactured and sold by DIC), 6 parts by weight of epoxy compound (1), and 4.66 parts by weight of 4,4'-methylenebis(2-methylaniline) (as a curing agent) were mixed to obtain a composition (1).

[0098] Example 12

[0099] 8.46 parts by weight of bisphenol F epoxy resin (product number EXA-830LVP, manufactured and sold by DIC), 6 parts by weight of epoxy compound (1), and 1.89 parts by weight of 1,5-pentanediamine (1,5-diaminopentane) (as a curing agent) were mixed to obtain a composition (2).

[0100] Example 13

[0101] 9.04 parts by weight of bisphenol F epoxy resin (product number EXA-830LVP, manufactured and sold by DIC), 6 parts by weight of epoxy compound (2), and 4.98 parts by weight of 4,4'-methylenebis(2-methylaniline) (as a curing agent) were added to obtain a composition (3).

[0102] Embodiment 14

[0103] 9.04 parts by weight of bisphenol F epoxy resin (product number EXA-830LVP, manufactured and sold by DIC), 6 parts by weight of epoxy compound (1), and 2.02 parts by weight of 1,5-pentanediamine (1,5-diaminopentane) (as a curing agent) were mixed to obtain a composition (4).

[0104] Embodiment 15

[0105] 8.05 parts by weight of bisphenol F epoxy resin (product number EXA-830LVP, manufactured and sold by DIC), 3 parts by weight of epoxy compound (3), and 4.43 parts by weight of 4,4'-methylenebis(2-methylaniline) (as a curing agent) were added to obtain a composition (5).

[0106] Example 16

[0107] 9.04 parts by weight of bisphenol F epoxy resin (product number EXA-830LVP, manufactured and sold by DIC), 3 parts by weight of epoxy compound (3), and 1.80 parts by weight of 1,5-pentanediamine (1,5-diaminopentane) (as a curing agent) were mixed to obtain a composition (6).

[0108] Comparative Example 1

[0109] 7.1 parts by weight of bisphenol F epoxy resin (product number EXA-830LVP, manufactured and sold by DIC) and 3.15 parts by weight of 4,4'-methylenebis(2-methylaniline) (as a curing agent) were mixed to obtain a composition (7).

[0110] Comparative Example 2

[0111] 8.46 parts by weight of bisphenol F epoxy resin (product number EXA-830LVP, manufactured and sold by DIC), 6 parts by weight of epoxy compound (1), and 0.145 parts by weight of 1-methylimidazole (initiator) were mixed to obtain a composition (8).

[0112] The reaction exothermic curves of compositions (1), (3), (5) and (7) were measured using a differential scanning calorimeter (DSC 7, sold by Perkin Elmer) (heating rate of 10°C / min), and the exothermic peak temperature of the epoxy composition was measured. The results are shown in Table 2.

[0113] Table 2

[0114] DSC exothermic peak temperature (℃) Composition (1) 170 Composition (3) 160 Composition (5) 168 Composition (7) 180

[0115] It can be seen from Table 2 that the epoxy compound described in the present disclosure can reduce the curing temperature of the composition described in the present disclosure, so that the composition described in the present disclosure can be cured at a lower curing process temperature.

[0116] Test of properties of cured products

[0117] The compositions (1), (3), (5), and (7) were respectively poured into a mold (30 mm x 30 mm). Then, the compositions were cured at 100° C. for 1 hour, at 130° C. for 3 hours, and at 160° C. for 3 hours to obtain cured products of the compositions (1), (3), (5), and (7).

[0118] The epoxy compositions (2), (6), and (4) were poured into molds (30 mm x 30 mm) respectively, and then cured at 70° C. for 3 hours and at 110° C. for 2 hours to obtain cured products of the epoxy compositions (2) and (4).

[0119] The epoxy composition (8) was poured into a mold (30 mm x 30 mm) and then cured at 100°C for 1 hour, at 140°C for 4 hours, and at 180°C for 3 hours to obtain a cured product of the composition (8).

[0120] Next, the thermal conductivity of the cured products of the epoxy compositions (1) to (8) was measured, and the results are shown in Table 3. The thermal conductivity was evaluated using a laser flash thermal constant measuring device (TC-7000, manufactured by LVAC-RIKO) in accordance with ASTM-E1461.

[0121] Table 3

[0122]

[0123]

[0124] It can be seen from Table 3 that the thermal conductivity of the cured product of the composition of the present disclosure can be improved by using the epoxy compound of the present disclosure.

[0125] In summary, by introducing the epoxy compound with a specific structure of the present disclosure, the composition of the present disclosure has a lower curing temperature and processability. In addition, the composition of the present disclosure can be applied to liquid packaging materials, and its cured product has a higher thermal conductivity, meeting the requirements of thermal conductive packaging materials.

[0126] Although the present disclosure has been disclosed in multiple embodiments as above, it is not intended to limit the present disclosure. Any person with ordinary knowledge in the technical field can make any changes and modifications without departing from the spirit and scope of the present disclosure. Therefore, the scope of protection of the present disclosure shall be determined by the appended claims.

Claims

1. An epoxy compound having a structure shown in formula (I) Where R 1 and R 2 Each is independently cyano, isocyanate, oxiranyl, methyloxiranyl, glycidyl, methylglycidyl, glycidoxy, oxetanyl, oxetanylmethyl, or C 1-10 Alkoxy; Z is -O-, R 3 and R 4 each is independently hydrogen, fluorine, methyl, fluoromethyl, or ethyl; n and m are each independently 3, 4, 5, 6, 7, 8, 9, or 10; and i and j are each independently 1, 2, or 3.

2. The epoxy compound according to claim 1, wherein the epoxy compound is Where R 1 and R 2 Each is independently cyano, isocyanate, oxiranyl, methyloxiranyl, glycidyl, methylglycidyl, glycidoxy, oxetanyl, oxetanylmethyl, or C 1-10 alkoxy; n and m are each independently 3, 4, 5, 6, 7, 8, 9, or 10; and i and j are each independently 1, 2, or 3.

3. The epoxy compound according to claim 1, wherein the epoxy compound is Where R 1 and R 2 Each is independently cyano, isocyanate, oxiranyl, methyloxiranyl, glycidyl, methylglycidyl, glycidoxy, oxetanyl, oxetanylmethyl, or C 1-10 Alkoxy; Z is -O-, R 3 and R 4 each is independently hydrogen, fluorine, methyl, fluoromethyl, or ethyl; and n and m are each independently 3, 4, 5, 6, 7, 8, 9, or 10.

4. The epoxy compound according to claim 1, wherein the epoxy compound is Where Z is -O-, R 3 and R 4 each is independently hydrogen, fluorine, methyl, fluoromethyl, or ethyl; and n and m are each independently 3, 4, 5, 6, 7, 8, 9, or 10.

5. The epoxy compound according to claim 1, wherein the epoxy compound is Where R 1 and R 2 Each is independently cyano, isocyanate, oxiranyl, methyloxiranyl, glycidyl, methylglycidyl, glycidoxy, oxetanyl, oxetanylmethyl, or C 1-10 Alkoxy; Z is -O-, R 3 and R 4 each is independently hydrogen, fluorine, methyl, fluoromethyl, or ethyl; and i and j are each independently 1, 2, or 3.

6. A composition comprising: The epoxy compound according to any one of claims 1 to 5; and The curing agent, wherein the weight ratio of the epoxy compound to the curing agent is 1:9 to 9:

1.

7. The composition of claim 6, wherein the curing agent is an isocyanate curing agent, a diamine curing agent, an anhydride curing agent, a phenol curing agent, an organic phosphonium curing agent, a thiol curing agent, or a combination thereof.

8. The composition of claim 6, further comprising: The epoxy resin comprises a weight ratio of the epoxy resin to the epoxy compound of 1:9 to 9:

1.

9. The composition of claim 8, wherein the epoxy resin is bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, novolac epoxy resin, naphthyl epoxy resin, anthracene epoxy resin, bisphenol A diglycidyl ether epoxy resin, ethylene glycol diglycidyl ether epoxy resin, propylene glycol diglycidyl ether epoxy resin, 1,4-butanediol diglycidyl ether epoxy resin, biphenyl type epoxy resin, cyclopentadiene type epoxy resin, or a combination thereof. 10 . A cured product, which is a cured product of the composition according to claim 6 .

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