TWI629291B - Resin composition - Google Patents

Abstract

The present invention provides an epoxy resin composition which is excellent in low-temperature quick-curing property and has a low Tg (glass transition point) of a cured product, and the Tg of the cured product hardly changes even after a long period of time after hardening.

The resin composition of the present invention contains (A) an epoxy resin containing no benzene ring, (B) a thiol compound having two or more thiol groups in the molecule, and (C) a latent curing agent. The component (B) is preferably blended in a ratio of a mercaptan equivalent ratio of 1.0 to 2.0 with respect to the epoxy equivalent of the above component (A).

Description

Resin composition

The present invention relates to an epoxy resin composition which is excellent in low-temperature quick-curing property and has a low Tg (glass transition point) of a cured product, and the Tg of the cured product hardly changes even after a long period of time after hardening.

A resin composition obtained from an epoxy resin, a thiol compound, and a curing accelerator, which is a resin composition which is excellent in low-temperature-speed hardening property which is hardened at a temperature of 0 to -20 ° C for a short period of time, and is used in Various uses such as a sealant for an adhesive and an electronic component. Patent Literatures 1 and 2 disclose examples of such resin compositions: a resin composition containing (1) an epoxy resin having two or more epoxy groups in a molecule, and (2) having two molecules in a molecule. The above thiol group-containing polythiol compound, and (3) a solid dispersion type latent curing accelerator. Patent Document 3 discloses an epoxy resin composition containing a bisphenol A type epoxy resin having a flexible skeleton and a polar bonding group, and a polythiol having two or more thiol groups.

[references] (Patent Literature)

Patent Document 1: Japanese Patent Publication No. 6-211969

Patent Document 2: Japanese Laid-Open Patent Publication No. Hei 6-211970

Patent Document 3: Japanese Laid-Open Patent Publication No. 2006-36935

However, when two parts having different coefficients of thermal expansion are joined to each other by an adhesive, thermal stress acts on the joint portion due to a change in ambient temperature, and cracks or the like are generated. Therefore, the adhesive used to join the parts must have flexibility to follow the degree of thermal deformation of the part, and the Tg (glass transition point) after the hardening of the adhesive is required to be low (i.e., the modulus of elasticity is low).

However, the epoxy resin compositions described in Patent Documents 1 and 2 have excellent low-temperature curability and storage stability, but there is a problem that Tg cannot be sufficiently lowered. Further, the epoxy resin composition described in Patent Document 3 can be cured at a low temperature, and the cured product can absorb stress because it has a certain degree of flexibility and flexibility. However, the cured product has the following problems: After hardening, the softness and flexibility are gradually lost.

The present invention has been made in view of the above problems, and an object thereof is to provide an epoxy resin composition which is excellent in low-temperature quick-curing property and has a low Tg (glass transition point) of a cured product, and a cured product after a long period of time after hardening. The Tg will hardly change.

The inventors of the present invention conducted various experiments to solve the above problems, and as a result, found that a resin composition containing an epoxy resin containing no benzene ring, a thiol compound having two or more thiol groups in the molecule, and a latent curing agent It is excellent in low-temperature quick-curing property and low in Tg of the cured product, and the Tg of the cured product hardly changes even after a long period of time after hardening.

The present invention is a resin composition comprising (A) an epoxy resin containing no benzene ring, (B) a thiol compound having two or more thiol groups in the molecule, and (C) a latent curing agent.

In the resin composition of the present invention, the component (A) is preferably a compound represented by the following formula (1).

(wherein R ₁ represents a linear or branched alkyl group having 1 to 15 carbon atoms; n is 1 to 20)

In the resin composition of the present invention, the component (A) is preferably a compound represented by the following formula (2).

(where m is 1 to 15)

Further, in the resin composition of the present invention, the component (A) is preferably a compound represented by the following formula (3).

(where l is 1 to 20)

In the resin composition of the present invention, the component (A) is preferably a compound represented by the following formula (4).

(wherein R ₂ to R ₅ each represent a straight or branched alkyl group having 1 to 3 carbon atoms)

In the resin composition of the present invention, the component (B) is preferably blended in a ratio of a mercaptan equivalent ratio of 1.0 to 2.0 with respect to the epoxy equivalent of the component (A).

In the resin composition of the present invention, the component (B) is preferably at least one selected from the group consisting of tetraethylene glycol bis (3-mercaptopropionate) and tris(3-). Mercaptopropionic acid) trimethylolpropyl ester, tetrakis(3-mercaptopropionic acid) neopentyl glycol ester, and hexa(3-mercaptopropionic acid) dineopentalt tetraol ester.

The resin composition of the present invention preferably comprises a ruthenium dioxide filler, a decane coupling agent, an ion scavenger, a leveling agent, an antioxidant, an antifoaming agent, and a thixotropic agent. At least one additive selected by the group.

Further, the present invention provides an electronic component which is sealed by a sealant containing any of the above resin compositions.

Further, the present invention provides an adhesive comprising any of the above resin compositions.

According to the present invention, there is provided an epoxy resin composition which is excellent in low-temperature-speed hardenability and has a low Tg (glass transition point) of a cured product, and hardly changes even after a long period of time Tg after hardening.

Hereinafter, embodiments of the present invention will be described in detail.

The resin composition of the embodiment of the present invention contains (A) an epoxy resin containing no benzene ring, (B) a thiol compound having two or more thiol groups in the molecule, and (C) a latent curing agent.

The epoxy resin of the above component (A) is preferably a compound represented by the following formula (1).

(wherein R ₁ represents a linear or branched alkyl group having 1 to 15 carbon atoms. n is 1 to 20)

The compound represented by the above formula (1) is preferably a compound represented by the following formula (2) and/or (3), for example.

(where m is 1 to 15)

(where l is 1 to 20)

Further, the compound represented by the above formula (1) is preferably a compound represented by the following formula (4), for example.

Further, in the following formula (4), R ₂ to R _{5 are} preferably a methyl group.

(wherein R ₂ to R ₅ each represent a straight or branched alkyl group having 1 to 3 carbon atoms)

The thiol compound of the above component (B) may be one having two or more thiol groups per molecule. From the standpoint of preservation stability, it is preferred that the content of the alkaline impurities is as small as possible. Examples of such thiol compounds include thiol compounds obtained by esterification of a polyhydric alcohol with a mercapto organic acid: trimethylolpropane tris (thioglycolate), tetrakis (mercaptoacetic acid) neopentyl Tetraol ester, bis(mercaptoacetic acid) ethylene glycol ester, trimethylolpropane tris (β-thiopropionate), tetrakis (β-thiopropionic acid) neopentyl Tetraol ester, dipentaerythritol poly(β-thiopropionate), tris-[(3-mercaptopropoxy)-ethyl]-iso-cyanide Acid esters, etc.

Similarly, the thiol compound may be exemplified by 1,4-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol, 1,8-octanedithiol, 1,9-fluorene. An alkyl polythiol compound such as a dithiol or a 1,10-fluorene dithiol; a polyether having a terminal thiol group; a polythioether containing a terminal thiol group; and a thiol obtained by reacting an epoxy compound with hydrogen sulfide a compound; a thiol compound having a terminal thiol group obtained by reacting a polythiol compound with an epoxy compound; and the like. The reaction catalyst in the production step is a basic substance, and the thiol compound having two or more thiol groups in the molecule is preferably subjected to a dealumination treatment to have an alkali metal ion concentration of 50 ppm or less.

The latent curing agent of the above (C) component means an imidazole compound which is solid at normal temperature, which is a solid which is insoluble in an epoxy resin at room temperature, and is soluble by heating and has a hardening accelerator. The function and the solid adduct amine extender are potential hardening accelerators, and examples thereof include a reaction product of an amine compound and an epoxy compound (amine-epoxy adduct system), an amine compound and A reaction product (urea type adduct system) of an isocyanate compound or a urea compound.

The imidazole compound which is solid at normal temperature used in the present invention may, for example, be 2-pyridyl imidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 2-undecylimidazole or 2-phenyl-4. -methyl-5-hydroxymethylimidazole, 2-phenyl-4-benzyl-5-hydroxymethylimidazole, 2,4-diamino-6-(2-methylimidazolyl-(1)) -ethyl-S-three (2,4-diamino-6-(2-methylimidazolyl-(1))-ethyl-S-triazine), 2,4-diamino-6-(2'-methylimidazolyl-(1)') -ethyl-S-three ‧Isocyanuric acid adduct, 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole-trimellitate, trimellitic acid (1-cyanoethyl-2-phenylimidazolium) ester , N-(2-methylimidazolyl-1-ethyl)-urea, N,N'-(2-methylimidazolyl-(1)-ethyl)-hexanediyldiamine (N, N'-(2-methylimidazolyl-(1)-ethyl)adipoyldiamide), etc., but is not limited thereto.

The epoxy compound used as one of the raw materials for the production of the latent amine-based adducts (amine-epoxy adducts) used in the present invention may, for example, be bisphenol A or Polyphenols such as phenol F, catechol, resorcinol, or polyepoxypropyl groups obtained by reacting glycerol and polyethylene glycol polyols with epichlorohydrin Ether; p-hydroxybenzoic acid, β-hydroxynaphthoic acid hydroxycarboxylic acid and epichlorohydrin reacted with epoxidized propyl ether ester; phthalic acid, terephthalic acid a polyepoxypropyl ester obtained by reacting epichlorohydrin; a glycidylamine compound obtained by reacting epichlorohydrin with 4,4'-diaminodiphenylmethane and m-aminophenol; Polyfunctional epoxy compound such as phenol novolac resin, epoxidized cresol novolac resin, epoxidized polyolefin, butyl epoxypropyl ether, phenyl epoxide a monofunctional epoxy compound such as a glycol ether or a glycidyl methacrylate, but not Within such.

The amine compound used in another raw material for producing a latent solid amine-based adduct which is a latent curing accelerator used in the present invention, as long as it has one or more activities capable of reacting with an epoxy group in its molecule Hydrogen, and having at least one functional group selected from the group consisting of a primary amine, a secondary amine, and a tertiary amine. These amine compounds are exemplified as follows, but are not limited thereto. That is, for example, di-ethyltriamine, tri-ethyltetramine, n-propylamine, (2-hydroxyethylamino)propylamine, cyclohexylamine, 4,4'-diamino-dicyclohexylmethane Aliphatic amines such as 4,4'-diaminodiphenylmethane, aromatic amine compounds such as 2-methylaniline; 2-ethyl-4-methylimidazole, 2-ethyl- 4-ethyl-4-methylimidazoline, 2,4-dimethylimidazoline, piperidine, piperidine A heterocyclic compound or the like containing a nitrogen atom.

Further, among them, in particular, a compound having a tertiary amino group in the molecule, which is a raw material which gives a latent hardening accelerator an excellent hardening-promoting ability, and examples of such a compound include dimethylaminopropylamine and diethylamino group. Propylamine, di-n-propylaminopropylamine, dibutylaminopropylamine, dimethylaminoethylamine, diethylaminoethylamine, N-methylpiperidone An amine compound; and an imidazole compound such as 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole or 2-phenylimidazole having a tertiary amine group or a secondary molecule in the molecule Amines; 2-dimethylaminoethanol, 1-methyl-2-dimethylaminoethanol, 1-phenoxymethyl-2-dimethylaminoethanol, 2-diethylamino Ethanol, 1-butoxymethyl-2-dimethylaminoethanol, 1-(2-hydroxy-3-phenoxypropyl)-2-methylimidazole, 1-(2-hydroxy-3- Phenoxypropyl)-2-ethyl-4-methylimidazole, 1-(2-hydroxy-3-butoxypropyl)-2-methylimidazole, 1-(2-hydroxy-3-butyl Oxypropyl)-2-ethyl-4-methylimidazole, 1-(2-hydroxy-3-phenoxypropyl)-2-phenylimidazoline, 1-(2-hydroxy-3-butyl Oxypropyl)-2-methylimidazoline, 2-(dimethylaminomethyl)phenol, 2,4,6-tris(dimethylaminomethyl)phenol, N-β-hydroxyethyl N-β-hydroxyethylmorpholine, 2-dimethylaminoethanethiol, 2-mercaptopyridine, 2-benzimidazole, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole ), 4-mercaptopyridine, N,N-dimethylaminobenzoic acid, N,N-dimethylglycine (N,N-dime) Thylglycine), nicotinic acid, isonicotinic acid, picolinic acid, N,N-dimethylglycinehydrazide, N,N-dimethylpropane Anthracene, nicotine, an isonicotinium, or the like, an alcohol having a tertiary amino group in the molecule, a phenol, a thiol, a carboxylic acid, and an anthracene.

In order to further improve the storage stability of the epoxy resin composition of the present invention, when the epoxy compound and the amine compound are subjected to an addition reaction to produce the latent curing accelerator used in the present invention, two or more active hydrogens may be added in the molecule. The active hydrogen compound is used as the third component. Examples of such active hydrogen compounds are as follows, but are not limited thereto. That is, for example, polyphenols such as bisphenol A, bisphenol F, bisphenol S, hydroquinone, catechol, resorcin, pyrogallol, and phenol novolac resin, and trishydroxyl Polyols such as propane, polycarboxylic acids such as adipic acid and phthalic acid, 1,2-dimercaptoethane, 2-mercaptoethanol, 1-mercapto-3-phenoxy-2-propanol, fluorenyl Acetic acid, anthranilic acid, lactic acid, and the like.

The solid dispersion type amine adduct used in the present invention is a latent curing accelerator. Another isocyanate compound used as a raw material for production, for example, n-butyl isocyanate, isopropyl isocyanate, isocyanide a monofunctional isocyanate compound such as phenyl ester or benzyl isocyanate; hexamethylene diisocyanate, toluylene diisocyanate, 1,5-naphthyl diisocyanate, diphenylmethane-4, 4' -diisocyanate, isophorone diisocyanate, xylylene diisocyanate, p-phenylene diisocyanate, 1,3,6-hexamethylene triisocyanate, dicycloheptane triisocyanate A polyfunctional isocyanate compound such as (bicycloheptane triisocyanate); and a compound containing a terminal isocyanate group, etc., obtained by reacting a polyfunctional isocyanate compound with an active hydrogen compound. Examples of the terminal isocyanate group-containing compound include the following: an addition compound containing a terminal isocyanate group obtained by reacting a tolyl diisocyanate with trimethylolpropane, and a tolyl diisocyanate and pentaerythritol. The addition compound or the like containing a terminal isocyanate group is not limited thereto.

Further, examples of the urea compound include urea, thiourea, and the like, but are not limited thereto.

The solid dispersion type latent hardening accelerator used in the present invention is, for example, a combination of (a) a combination of the two components of the amine compound and the epoxy compound, and (b) a combination of the two components and the three components of the active hydrogen compound. Or (c) a combination of an amine compound and an isocyanate compound or/and a urea compound, or a combination of three components, which are mixed with each component and heated at room temperature to a temperature of 200 ° C, then cooled, solidified, and pulverized. Or methyl ethyl ketone, two After the reaction is carried out in a solvent such as dioxane or tetrahydrofuran, the solid component is pulverized by removing the solvent, whereby the solid dispersion type latent curing accelerator used in the present invention can be easily obtained.

Examples of the commercially available product of the solid dispersion type latent curing accelerator are as follows, but are not limited thereto. For example, the amine-epoxy adduct system (amine adduct system) includes "AJICURE PN-23" (trade name of Ajinomoto Co., Ltd.) and "AJICURE PN-40" (Ajinomoto Co., Ltd.) Company name), "HARDENER X-3661S" (trade name of ACR Co., Ltd.), "HARDENER X-3670S" (trade name of ACR Co., Ltd.), "NOVACURE HX-3742" (trade name of Asahi Kasei Co., Ltd.), "NOVACURE HX -3721" (product name of Asahi Kasei Co., Ltd.), etc., and the "FUJICURE FXE-1000" (Fuji Chemical Co., Ltd. product name) and "FUJICURE FXR-1030" (Fuji Chemical Co., Ltd.), etc. .

The preparation of the resin composition of the present invention using the components (A) to (C) as a raw material is not particularly difficult, and can be determined by a conventionally known method. The resin composition of the present invention can be prepared, for example, by mixing with a mixer such as a Henschel mixer.

Further, it is not particularly difficult to harden the resin composition of the present invention, and a conventionally known method can be used. The resin composition of the present invention can be cured, for example, by heating at 50 to 120 °C.

Further, the resin composition of the present invention is characterized by containing the above components (A) to (C). Thereby, a resin composition which is excellent in low-temperature quick-curing property and has a low Tg (glass transition point) of the cured product can be obtained. Further, a resin composition which hardly changes to a Tg of a cured product after a long period of time by curing the resin composition by heating the resin composition can be obtained.

The reason why the resin composition is obtained is as follows: the epoxy resin molecule of the above (A) component does not contain a benzene ring; or the ring of the compound represented by the above formula (2) and formula (3) The oxygen equivalent is higher; or the compound represented by the above formula (4) has a fluorene resin skeleton present in the molecule.

In the resin composition of the present invention, the component (B) is preferably blended in a ratio of a mercaptan equivalent ratio of 1.0 to 2.0 (1.0 or more and 2.0 or less) based on the epoxy equivalent of the component (A). Here, "epoxy equivalent" means a value obtained by dividing the molecular weight of an epoxy resin by the number of epoxy groups in one molecule. The "thiol equivalent" means a value obtained by dividing the molecular weight of a thiol compound by the number of thiol groups in one molecule. That is, with respect to the epoxy equivalent of the above component (A), the above (B) component has a mercaptan equivalent ratio of 1.0 to 2.0, and represents a number of thiol groups of from 1.0 to 2.0 with respect to the number of epoxy groups.

By setting the blending ratio of the component (A) and the component (B) in the above range, the resin composition can be hardened into a cured product, and the Tg of the cured product is hardly changed even after a long period of time. Resin composition. It is considered that the reason why such a resin composition can be obtained is that the thiol equivalent ratio of the component (B) is set to an appropriate range with respect to the epoxy equivalent of the component (A). That is, when the thiol equivalent ratio of the component (B) is less than 1.0 with respect to the epoxy equivalent of the component (A), since a part of the epoxy group does not react with the thiol group, it is considered that the remaining epoxy group is The reason why the hardened material is hardened. On the other hand, when the thiol equivalent ratio of the component (B) is more than 2.0 with respect to the epoxy equivalent of the component (A), since a part of the thiol group does not react with the epoxy group, it remains as the remaining sulfur. The alcohol group is the cause of hardening of the hardened material.

The resin composition of the present invention may further comprise at least one selected from the group consisting of a ceria filler, a decane coupling agent, an ion scavenger, a leveling agent, an antioxidant, an antifoaming agent, and a rocking agent. additive. Further, it may contain a viscosity modifier, a fire retardant or a solvent.

The resin composition of the present invention can be used as an adhesive for bonding parts to each other or a raw material thereof.

The resin composition of the present invention can be used as a sealant for electronic parts or a raw material thereof.

The adhesive agent using the resin composition of the present invention preferably has an elastic modulus of from 0.01 to 1.5 GPa, more preferably from 0.4 to 0.8 GPa.

When the modulus of elasticity is less than 0.01 GPa, the hardened portion of the adhesive becomes brittle. When the modulus of elasticity is larger than 1.5 GPa, the shrinkage stress of the adhesive may cause cracks in the cured product.

Further, the Tg of the resin composition of the present invention preferably has a Tg of from -20 to -55 ° C, more preferably from -30 to -38 ° C.

When the Tg is higher than -20 ° C, the hardened portion of the adhesive may have cracks. Further, depending on the strength of the adhesion to the adherend, there is a case where the adherend is cracked. When the Tg is lower than -55 ° C, the hardened portion becomes brittle.

(Example)

The following describes the embodiments of the present invention, but the present invention is not limited thereto.

(modulating resin composition)

The components of the compositions of Examples 1 to 20 were prepared by mixing the components in the combination shown in the following Tables 1 and 2.

The components of Comparative Examples 1 to 4 were prepared by mixing the components in the combination shown in Table 3 below.

Further, in Tables 1 to 3, the numbers indicating the blending ratios of the components (A) to (F) represent parts by weight.

In Tables 1 to 3, the specific substance names of the respective components are as follows.

(A1) Epoxy Resin 1: "YDF8170" manufactured by Nippon Steel Chemical Co., Ltd., bisphenol F-type epoxy resin, and having a weight average molecular weight of 165.

(A2) Epoxy Resin 2: "YL7410" (epoxy resin of the above formula (2)) manufactured by Japan Epoxy Resins Co., Ltd., and having a weight average molecular weight of 435.

(A3) Epoxy Resin 3: "PP300P" (epoxy resin of the above formula (3)) manufactured by Sanyo Chemical Industries Co., Ltd., and having a weight average molecular weight of 181.3.

(A4) Epoxy Resin 4: "TSL9906" manufactured by Momentive Performance Materials Co., Ltd. (in the above formula (4), R ₂ to R ₅ are epoxy resins of a methyl group), and the weight average molecular weight is 296.

(B1) thiol compound 1: "PEMP" tetrakis(3-mercaptopropionic acid) pentaerythritol ester manufactured by SC Organic Chemical Co., Ltd., weight average molecular weight 489.

(B2) Thiol compound 2: "TMMP" tris(3-mercaptopropionic acid) trimethylolpropyl ester manufactured by SC Organic Chemical Co., Ltd., weight average molecular weight 398.

(B3) Mercaptan compound 3: "DPMP" hexa(3-mercaptopropionic acid) dipivalol ester manufactured by SC Organic Chemical Co., Ltd., weight average molecular weight 783.

(C) Potential hardener: "PN40J" epoxy resin amine adduct manufactured by Ajinomoto Fine-Techno.

(D) Stabilizer: "L07N" manufactured by Shikoku Chemicals Co., Ltd., bisphenol A type epoxy resin / phenol resin / boric acid ester.

(E) Shaker: "R805" manufactured by Japan AEROSIL Co., Ltd., fumed silica.

(F) Coupling agent: "KBM403", 3-(glycidoxy)propyltrimethoxydecane manufactured by Shin-Etsu Chemical Co., Ltd.

(3-glycidoxypropyltrimethoxysilane) (production of hardened material)

Each of the resin compositions of Examples 1 to 20 and Comparative Examples 1 to 4 was heated at 80 ° C for 10 minutes. As a result, Examples 1 to 20 and Comparative Example 1 obtained a hardened cured product of a resin composition. Comparative Examples 2 to 4 did not obtain a cured product because the resin composition was not cured.

(measuring Tg and modulus of elasticity)

The elastic modulus [GPa] of the cured product obtained by curing the resin composition, the elastic modulus [GPa] after standing at 120 ° C for 48 hours, the glass transition point Tg [° C], and the temperature at 120 ° C after hardening were respectively measured. The glass transition point Tg [° C.] after 48 hours of standing, and the subsequent strength [N/mm ² ]. The results of the measurements are shown in Tables 1 to 3.

The modulus of elasticity was measured according to Japanese Industrial Standard JIS C6481 using a dynamic thermal mechanical analyzer (DMA) manufactured by Seiko Instruments Co., Ltd. at -40 °C.

Tg was measured according to Japanese Industrial Standard JIS C6481 using a dynamic thermal mechanical analyzer (DMA) manufactured by Seiko Instruments.

The bonding strength was determined using the following test method.

(1) The sample was stenciled on a glass epoxy substrate at a size of 2 mm.

(2) A 2 mm × 2 mm Si wafer was placed on the printed sample. It was hardened at 180 ° C for 60 minutes using a blow dryer.

(3) Shear strength was measured on a table universal testing machine (1605 HTP manufactured by Aikoh Engineering Co., Ltd.).

Evaluation method

When the cured product was placed at 120 ° C for 48 hours, if the change in Tg was within ± 5 ° C, the change in Tg was evaluated as "none".

When the cured product was placed at 120 ° C for 48 hours, if the change in the elastic modulus was within ±0.1 GPa, the change in the elastic modulus was evaluated as "none".

As a result of observing Examples 1 to 20, it was found that the resin composition of the present invention can be cured in a short time under heating at 80 ° C, and is excellent in low-temperature-speed hardenability. On the other hand, as a result of observing Comparative Examples 2 to 4, it was found that the resin composition of the comparative example had an excessively small thiol equivalent ratio with respect to the epoxy equivalent of 0.5, so that it was not sufficiently cured under heating at 80 °C.

As a result of observing the results of the examples 1 to 20, it is understood that the cured product of the resin composition of the present invention has an elastic modulus of from 0.1 to 0.8 [GPa] at -40 ° C, and a cured product having a small modulus of elasticity can be obtained. On the other hand, as a result of observing the results of Comparative Example 1, it was found that the resin composition of the comparative example had an elastic modulus of 4.0 [GPa] at -40 ° C, and a cured product having a small modulus of elasticity could not be obtained.

When the results of Examples 1 to 20 were observed, it was found that the resin composition of the present invention had a Tg of -50 ° C to -30 ° C, and it was found that the Tg of the cured product was low. On the other hand, as a result of observing Comparative Example 1, it was found that the resin composition Tg of the comparative example was 40 ° C, and a cured product having a low Tg could not be obtained.

The results of Examples 1 to 17 were observed, and it was found that the elastic modulus and Tg of the cured product hardly changed even after being cured at 120 ° C for 48 hours after the resin composition of the present invention was cured. From this, it can be confirmed that the Tg of the resin composition of the present invention hardly changes even after a long period of time after hardening.

Claims (8)

A resin composition containing the following (A) to (C) components: (A) an epoxy resin containing no benzene ring, (B) a thiol compound having two or more thiol groups in a molecule, and (C) a latent hardener; wherein, in the epoxy equivalent of the above component (A), the component (B) is formulated in a ratio of a mercaptan equivalent ratio of from 1.5 to 2.0, and the modulus of elasticity of the cured product at -40 ° C is 0.3. To 0.8GPa. The resin composition according to the first aspect of the invention, wherein the component (A) is a compound represented by the following formula (1) (wherein R ₁ represents a linear or branched alkyl group having 1 to 15 carbon atoms; n is 1 to 20). The resin composition according to the second aspect of the invention, wherein the component (A) is a compound represented by the following formula (2) (where m is 1 to 15). The resin composition according to claim 2, wherein the component (A) is a compound represented by the following formula (3) (where l is 1 to 20). The resin composition according to any one of claims 1 to 4, wherein the component (B) is selected from the group consisting of bis(3-mercaptopropionic acid) tetraethylene glycol ester, and tris(3-) At least one of mercaptopropionic acid) trimethylolpropyl ester, tetrakis(3-mercaptopropionic acid) neopentyl glycol ester, and hexa(3-mercaptopropionic acid) dineopentalol ester. The resin composition according to any one of the preceding claims, wherein the resin composition is selected from the group consisting of a ceria filler, a decane coupling agent, an ion scavenger, a leveling agent, an antioxidant, and a defoaming agent. At least one additive in the group of agents and shakers. An electronic component which is sealed with a sealant containing the resin composition according to any one of claims 1 to 6. An adhesive comprising the resin composition according to any one of claims 1 to 6.