JP2022064622A - Sealing agent and article - Google Patents

Abstract

To provide a sealing agent excellent in sealability and quick curability, and an article obtained by using the sealing agent.SOLUTION: The sealing agent is a curable composition which contains a 2-cyanoacrylate compound represented by the following formula (1), and a cured product of the curable composition has a storage modulus at 23°C of 1.0×104 Pa or more and 1.0×108 Pa or less. In the formula (1), each L1 independently represents a C2-6 linear or branched alkylene group which may have a substituent; p represents an integer of 2-8; and R1 represents a C1-8 linear or branched alkyl group, an aryl group, an alkenyl group, or an alkynyl group which may have a substituent.SELECTED DRAWING: Figure 1

Description

The present invention relates to a sealant and an article.

Various sealing agents are used as materials for filling gaps and scratches between members. For example, Patent Document 1 describes a sealing agent containing an acrylic polymer having at least two reactive silyl groups as a main component. Further, it is described that this sealant can be cured at room temperature by the moisture in the air, the cured product after curing has rubber elasticity, and the adhesiveness to the adherend is also excellent.

Japanese Unexamined Patent Publication No. 2019-189772

When using a sealant, it is considered that the handleability is greatly improved if the time from filling to curing is short. However, in the examples of the invention described in Patent Document 1, it takes 7 days to cure, and shortening of the curing time of the sealing agent has not been studied.

Therefore, an object to be solved by the present invention is to provide a sealing agent having excellent sealing property and quick-curing property, and an article obtained by using this sealing agent.

式（１）中、Ｌ^１はそれぞれ独立に、置換基を有してもよい炭素数２～６の直鎖又は分岐アルキレン基を表し、ｐは２～８の整数を表し、Ｒ^１は置換基を有してもよい、炭素数１～８の直鎖若しくは分岐アルキル基、アリール基、アルケニル基、又は、アルキニル基を表す。
＜２＞前記硬化性組成物の硬化物のガラス転移温度が、６０℃以下である＜１＞に記載のシーリング剤。
＜３＞前記硬化性組成物の硬化物のプローブタック試験におけるタック値が、０．１Ｎ／ｃｍ^２以上１００Ｎ／ｃｍ^２以下である、＜１＞又は＜２＞に記載のシーリング剤。
＜４＞前記硬化性組成物の硬化物の応力－ひずみ曲線における伸び率が、３５０％以上である、＜１＞～＜３＞のいずれか１項に記載のシーリング剤。
＜５＞ＪＩＳ Ｚ ０２３７（２００９）に準拠して測定されるガラスと易接着性ポリエチレンテレフタレート基材とを前記硬化性組成物を硬化させて接着した接着物の１８０°引きはがし粘着力が、５Ｎ／２５ｍｍ以上１００Ｎ／２５ｍｍ以下である、＜１＞～＜４＞のいずれか１項に記載のシーリング剤。
＜６＞ＪＩＳ Ｚ ０２３７（２００９）に準拠して測定されるアルミニウム基材同士を前記硬化性組成物を硬化させて接着した接着物の１８０°引きはがし粘着力が、５Ｎ／２５ｍｍ以上５０Ｎ／２５ｍｍ以下である、＜１＞～＜５＞のいずれか１項に記載のシーリング剤。
＜７＞前記Ｌ^１がそれぞれ独立に、－ＣＨ_２ＣＨ_２－、－ＣＨ（Ｒ^２）ＣＨ_２－又は－ＣＨ_２ＣＨ（Ｒ^２）－であり、Ｒ^２が炭素数１～６のアルキル基である、＜１＞～＜６＞のいずれか１項に記載のシーリング剤。
＜８＞前記ｐが、２～６の整数である、＜１＞～＜７＞のいずれか１項に記載のシーリング剤。
＜９＞前記Ｒ^１が、炭素数１～６の直鎖又は分岐アルキル基である、＜１＞～＜８＞のいずれか１項に記載のシーリング剤。
＜１０＞前記硬化性組成物の２５℃における初期粘度が、３００Ｐａ・ｓ以下であり、
２５℃６０％ＲＨの環境下において、前記硬化性組成物０．１ｇに対し５体積％トリエタノールアミンのアセトン溶液１μＬ添加した時から前記硬化性組成物の硬化物の貯蔵弾性率が１．０×１０^４Ｐａ以上１．０×１０^８Ｐａ以下の範囲で略一定になるまでの時間が、６０分以下である、＜１＞～＜９＞のいずれか１項に記載のシーリング剤。
＜１１＞粘着付与剤、可塑剤、ゴム強化剤、抗酸化剤、及び、ポリマーよりなる群から選択される少なくとも１種の化合物を更に含む、＜１＞～＜１０＞のいずれか１項に記載のシーリング剤。
＜１２＞部材と、前記部材が有する隙間を充填する＜１＞～＜１１＞のいずれか１項に記載のシーリング剤の硬化物と、を備える物品。 The means for solving the above-mentioned problems include the following aspects.
<1> A curable composition, which is a curable composition.
It contains a 2-cyanoacrylate compound represented by the following formula (1).
A sealing agent, which is a curable composition having a storage elastic modulus of 1.0 × 10 ⁴ Pa or more and 1.0 × 10 ⁸ Pa or less at 23 ° C. of the cured product of the curable composition.

In formula (1), L ¹ independently represents a linear or branched alkylene group having 2 to 6 carbon atoms which may have a substituent, p represents an integer of 2 to 8, and R ¹ represents a substituent. It represents a linear or branched alkyl group having 1 to 8 carbon atoms, an aryl group, an alkenyl group, or an alkynyl group which may have a group.
<2> The sealing agent according to <1>, wherein the cured product of the curable composition has a glass transition temperature of 60 ° C. or lower.
<3> The sealant according to <1> or <2>, wherein the tack value in the probe tack test of the cured product of the curable composition is 0.1 N / cm ² or more and 100 N / cm ² or less.
<4> The sealant according to any one of <1> to <3>, wherein the elongation rate of the cured product of the curable composition in the stress-strain curve is 350% or more.
<5> 180 ° peeling adhesive strength of the adhesive obtained by curing and adhering the curable composition between glass and an easily adhesive polyethylene terephthalate substrate measured in accordance with JIS Z 0237 (2009) is 5N. The sealing agent according to any one of <1> to <4>, which is 25 mm or more and 100 N / 25 mm or less.
<6> 180 ° peeling adhesive strength of an adhesive obtained by curing and adhering the curable composition between aluminum substrates measured in accordance with JIS Z 0237 (2009) is 5N / 25mm or more and 50N / 25mm. The sealing agent according to any one of <1> to <5>, which is described below.
<7> The L ¹ is independently -CH ₂ CH _2- , -CH (R ² ) CH _2- or -CH ₂ CH (R ² )-, and R ² is an alkyl having 1 to 6 carbon atoms. The sealing agent according to any one of <1> to <6>, which is a base.
<8> The sealing agent according to any one of <1> to <7>, wherein p is an integer of 2 to 6.
<9> The sealing agent according to any one of <1> to <8>, wherein R ¹ is a linear or branched alkyl group having 1 to 6 carbon atoms.
<10> The initial viscosity of the curable composition at 25 ° C. is 300 Pa · s or less.
In an environment of 25 ° C. and 60% RH, the storage elastic modulus of the cured product of the curable composition is 1.0 from the time when 1 μL of an acetone solution of 5% by volume triethanolamine is added to 0.1 g of the curable composition. The sealing agent according to any one of <1> to <9>, wherein the time required to become substantially constant in the range of × 10 ⁴ Pa or more and 1.0 × 10 ⁸ Pa or less is 60 minutes or less.
<11> In any one of <1> to <10>, further comprising at least one compound selected from the group consisting of a tackifier, a plasticizer, a rubber strengthening agent, an antioxidant, and a polymer. The sealant described.
An article comprising the <12> member and the cured product of the sealing agent according to any one of <1> to <11>, which fills the gap of the member.

According to the present invention, it is possible to provide a sealing agent having excellent sealing properties and quick-curing properties, and an article obtained by using this sealing agent.

The elongation rate in the stress-strain curve of the cured product of the curable composition of Examples 2 to 4 and Comparative Example 1 is shown.

The description of the constituent elements described below may be based on a representative embodiment of the present invention, but the present invention is not limited to such embodiments. In the specification of the present application, "-" is used to mean that the numerical values described before and after it are included as the lower limit value and the upper limit value.
In the numerical range described stepwise in the present specification, the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of another numerical range described stepwise. good. Further, in the numerical range described in the present specification, the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
In the present invention, "% by mass" and "% by weight" are synonymous, and "parts by mass" and "parts by weight" are synonymous.
Further, in the present invention, the combination of two or more preferred embodiments is a more preferred embodiment.
Hereinafter, the contents of the present invention will be described in detail.

The sealing agent of the present invention is a curable composition, which contains a 2-cyanoacrylate compound represented by the following formula (1), and has a storage elastic modulus of 1 at 23 ° C. of the cured product of the curable composition. It is a sealing agent which is a curable composition having a size of 0.0 × 10 ⁴ Pa or more and 1.0 × 10 ⁸ Pa or less.

In formula (1), L ¹ independently represents a linear or branched alkylene group having 2 to 6 carbon atoms which may have a substituent, p represents an integer of 2 to 8, and R ¹ represents a substituent. It represents a linear or branched alkyl group having 1 to 8 carbon atoms, an aryl group, an alkenyl group, or an alkynyl group which may have a group.

The curable composition which is the sealing agent of the present invention contains a 2-cyanoacrylate compound represented by the above formula (1) having 2 to 8 alkyleneoxy structures. This compound easily undergoes a polymerization reaction with moisture in the air, for example, and cures rapidly. Therefore, the sealant of the present invention is excellent in quick-curing property.

Further, the sealing agent of the present invention exhibits excellent sealing properties. The mechanism of action of this effect is not clear, but it is estimated as follows.
The curable composition as a sealing agent contains a 2-cyanoacrylate compound represented by the above formula (1) having 2 to 8 alkyleneoxy structures, and the storage elastic modulus of the cured product at 23 ° C. Within the above range, it is presumed that the product has appropriate flexibility even after curing and exhibits adhesive strength on the surface of the cured product. Therefore, for example, good sealing performance is maintained even when the member after filling is deformed by an external force.

<Store elastic modulus of cured product at 23 ° C>
The storage elastic modulus of the cured product of the curable composition as the sealing agent of the present invention at 23 ° C. is 1.0 × 10 ⁴ Pa or more and 1.0 × 10 ⁸ Pa or less, and the adhesiveness of the obtained cured product is high. From the viewpoint, it is preferably 1.0 × 10 ⁴ Pa or more and 5.0 × 10 ⁷ Pa or less, and more preferably 1.0 × 10 ⁴ Pa or more and 1.0 × 10 ⁶ Pa or less. It is particularly preferable that it is 0 × 10 ⁴ Pa or more and 5.0 × 10 ⁵ Pa or less.

<Glass transition temperature of cured product>
The glass transition temperature (Tg) of the cured product of the curable composition as the sealing agent of the present invention is preferably 60 ° C. or lower, preferably 35 ° C. or lower, from the viewpoint of the adhesiveness of the obtained cured product. More preferably, it is more preferably −20 ° C. or higher and 35 ° C. or lower, and particularly preferably −10 ° C. or higher and 10 ° C. or lower.

The storage elastic modulus and the glass transition temperature (Tg) of the cured product of the curable composition shall be measured by the following methods.
After injecting the curable composition between the jigs for the following dynamic viscoelasticity measuring device coated with triethanolamine, the frequency is used using the dynamic viscoelasticity measuring device (manufactured by Anton Pearl Co., Ltd., product name "MCR301"). The storage elastic modulus is measured under the conditions of 1 Hz, a temperature of 25 ° C., and a thickness of 300 μm. It should be noted that the cured product is obtained by confirming that the change in the storage elastic modulus has disappeared. Using the cured product, the storage elastic modulus (E'), loss elastic modulus (E "), and loss tangent (tan δ = E) due to shearing in the range of -50 ° C to 100 ° C at a frequency of 1 Hz and a temperature rise rate of 2 ° C / min. "/ E') is measured.
In the present invention, "there is no change in the storage elastic modulus" means that the storage elastic modulus change rate per minute is 1% or less of the final storage elastic modulus at 25 ° C.
Further, the glass transition temperature (Tg) of the cured product of the curable composition is determined by using the peak temperature of the loss tangent (tan δ) as an evaluation index. The storage elastic modulus uses the value at 23 ° C.

<Tack value in probe tack test of cured product>
The tack value in the probe tack test of the cured product of the curable composition as the sealing agent of the present invention is 0.1 N / cm ² or more and 100 N / cm ² or less from the viewpoint of the adhesiveness of the obtained cured product. Preferably, it is preferably 1 N / cm ² or more and 100 N / cm ² or less, more preferably 10 N / cm ² or more and 100 N / cm ² or less, and 50 N / cm ² or more and 100 N / cm ² or less. Especially preferable.

The tack value in the probe tack test of the cured product of the curable composition shall be measured by the following method.
A 38 μm thick spacer (removable polyethylene terephthalate (PET) film (manufactured by Toyobo Film Solution Co., Ltd., product name “Purex A31”)) with a punched frame and a 125 μm thick easy-adhesive PET film (Toray (Toray) The adhesive composition was dropped into a spacer frame by placing it on a product name "Lumirror 125U34") manufactured by Co., Ltd. Another release PET film coated with triethanolamine is put on it and laminated, and allowed to stand at room temperature (25 ° C., the same applies hereinafter) for 24 hours to be completely cured. After curing, it is cut into a width of 15 mm and a length of 15 mm, and the release PET film is peeled off to obtain a test piece. Regarding this test piece, ASTM D2979: 2016 (partially compliant), Japanese Pharmacopoeia 6.12. (3.4.): Based on the 17th revised "Probe Tack Test Method", measured using a probe tack tester (manufactured by Tester Sangyo Co., Ltd., product name "TE-6002"), and the tack value (tack value ( Unit: N / cm ² ) is calculated.

<Stress of hardened material-elongation rate in strain curve>
The elongation rate in the stress-strain curve of the cured product of the curable composition as the sealing agent of the present invention is preferably 350% or more, preferably 500% or more, from the viewpoint of the adhesiveness and flexibility of the obtained cured product. Is more preferable, 750% or more is further preferable, and 900% or more is particularly preferable. The upper limit is preferably 10,000% or less.

The elongation in the stress-strain curve of the cured product of the curable composition shall be measured by the following method.
1 μL of triethanolamine was added to 1 g of the curable composition, and the mixture was stirred and then placed on a release PET film (manufactured by Toyobo Film Solution Co., Ltd., product name “Purex A31”) to form a 1 mm thick silicone rubber. Pour into the mold. Cover with a release film, sandwich it with a glass plate, and let it stand at room temperature for 24 hours to completely cure it. After curing, the mold and the release film are removed to prepare a cured product having a width of 5 mm, a length of 50 mm, and a thickness of 1 mm. Using a tensile tester (manufactured by Toyo Seiki Seisakusho Co., Ltd., product name "Strograph V20-C"), the stress-strain curve of this cured product is measured and the elongation rate is calculated.

<180 ° peeling adhesive strength of adhesive>
In the curable composition which is a sealing agent of the present invention, an adhesive obtained by curing and adhering a glass and an easily adhesive PET substrate measured in accordance with JIS Z 0237 (2009) by curing the curable composition. The 180 ° peeling adhesive strength is preferably 5N / 25mm or more and 100N / 25mm or less, and more preferably 10N / 25mm or more and 50N / 25mm or more, from the viewpoint of the adhesiveness and flexibility of the obtained cured product. It is more preferably 10 N / 25 mm or more and 35 N / 25 mm or less, and particularly preferably 10 N / 25 mm or more and 25 N / 25 mm or less.

Further, in the curable composition which is the sealing agent of the present invention, 180 ° of the adhesive obtained by curing and adhering the curable composition to the aluminum base materials measured according to JIS Z 0237 (2009). From the viewpoint of the adhesiveness and flexibility of the obtained cured product, the peeling adhesive strength is preferably 5N / 25 mm or more and 50N / 25mm or less, more preferably 5N / 25mm or more and 35N / 25mm or more, and 5N / It is particularly preferable that it is 25 mm or more and 25 N / 25 mm or less.

The "easy-adhesiveness" in the present invention means a property that the curable composition makes it easy to adhere and that peeling does not easily occur after the adhesive.

The 180 ° peeling adhesive strength of the curable composition shall be measured by the following method.

-Making an adhesive between glass and an easily adhesive PET substrate-
A 38 μm-thick spacer (release PET film (manufactured by Toyobo Film Solution Co., Ltd., product name “Purex A31”)) with a punched frame 25 mm wide and 150 mm long is mounted on a glass plate (AGC fabric) with a thickness of 1 mm. The curable composition is dropped onto the glass in the spacer frame on a product (product name "FL11AK") manufactured by Tech Co., Ltd. A 125 μm-thick, easy-adhesive PET film coated with triethanolamine (manufactured by Toray Industries, Inc., product name “Lumilar 125U34”) was placed on top of it, and the film was allowed to stand at room temperature for 24 hours to completely leave it. Cure. After curing, the spacer is removed to prepare a test piece having an adhesive layer having a thickness of 38 μm, a width of 25 mm, and a length of 150 mm, one side of which is a glass base material and the other side of which is an easy-adhesion PET base material.

-Making an adhesive between aluminum substrates-
A 38 μm-thick spacer (release PET film (manufactured by Toyobo Film Solution Co., Ltd., product name “Purex A31”)) with a 90 mm wide and 150 mm long punched frame is attached to a 0.1 mm thick aluminum plate. (Material specified in JIS A6061P) is placed, and the adhesive composition is dropped onto the aluminum plate in the spacer frame. A 1 mm-thick aluminum plate coated with triethanolamine is put on it and bonded, and the mixture is allowed to stand at room temperature for 24 hours to be completely cured. After curing, the spacer is removed and cut to a width of 25 mm to prepare a test piece having an adhesive layer having a thickness of 38 μm, a width of 25 mm and a length of 150 mm, and having an aluminum substrate on both sides.

-Measurement of peel strength-
For the test piece prepared under the above conditions, the end of the base material on one side (the easy-adhesive PET base material in the case of the adhesive between the glass and the easy-adhesive PET base material), and the aluminum base materials at a speed of 50 mm / min. The glass and the easy-adhesive PET base material are peeled off at a speed of 100 mm / min in the peeling direction of 180 °, and the adhesive force (resistance) (unit: N / 25 mm) to the adherend at that time is measured. The obtained measurement result is used as the 180 ° peeling adhesive strength of the curable composition.

<Viscosity of curable composition>
The viscosity of the curable composition, which is the sealing agent of the present invention, at 25 ° C. is preferably 300 Pa · s or less, preferably 100 Pa · s or less, from the viewpoint of coatability and the adhesiveness of the obtained cured product. More preferably, it is more preferably 50 Pa · s or less, and particularly preferably 10 Pa · s or more and 50 Pa · s or less.
The viscosity of the curable composition shall be measured under the conditions of 25 ° C. and 100 rpm using an E-type viscometer manufactured by Tokimec Co., Ltd.

<Curing time>
In the curable composition which is the sealing agent of the present invention, the curability is obtained from the time when 1 μL of an acetone solution of 5% by volume triethanolamine is added to 0.1 g of the curable composition in an environment of 25 ° C. and 60% RH. The time until the storage elastic modulus of the cured product of the composition becomes substantially constant in the range of 1.0 × 10 ⁴ Pa or more and 1.0 × 10 ⁸ Pa or less is the coatability and the adhesiveness of the obtained cured product. From the above viewpoint, it is preferably 60 minutes or less, more preferably 30 minutes or less, further preferably 20 minutes or less, and particularly preferably 10 minutes or less.
The time until the storage elastic modulus of the cured product becomes substantially constant is the time until the storage elastic modulus change rate per minute becomes 1% or less of the final storage elastic modulus at 25 ° C. do.
The method for measuring the storage elastic modulus of the cured product is as described above.

<2-Cyanoacrylate compound represented by the formula (1)>
The curable composition which is the sealing agent of the present invention contains the 2-cyanoacrylate compound represented by the above formula (1).
Examples of the substituent that L ¹ in the formula (1) may have include an aryl group, a halogen atom, an alkoxy group, an aryloxy group, a cyano group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group and an acyloxy group. Be done.
L ¹ in the formula (1) is independently represented by -CH ₂ CH _2- , -CH (R ² ) CH _2- or -CH ₂ CH (R ² )-from the viewpoint of the adhesiveness of the obtained cured product. It is preferably -CH (R ² ) CH _2- or -CH ₂ CH (R ² )-more preferably.
The R ² represents an alkyl group having 1 to 6 carbon atoms, and is preferably an alkyl group having 1 to 3 carbon atoms, and more preferably a methyl group, from the viewpoint of the adhesiveness of the obtained cured product.
Further, it is preferable that all R ² in the formula (1) have the same group.
Specifically, L ¹ in the formula (1) is an ethylene group, a 1,2-propylene group, a 1,3-propylene group, a 2,3-propylene group, a 1,2-butylene group, 1,3-. Butylene group, 1,4-butylene group, 2,3-butylene group, 2,4-butylene group, 3,4-butylene group, 1,2-pentylene group, 1,3-pentylene group, 1,4-pentylene group Examples thereof include a group, a 2,3-pentylene group, a 2,4-pentylene group, a 2,5-pentylene group, a 3,4-pentylene group, a 3,5-pentylene group, a 4,5-pentylene group and the like.
Above all, from the viewpoint of the adhesiveness of the obtained cured product, an ethylene group, a 1,2-propylene group, a 1,3-propylene group, a 2,3-propylene group, a 1,2-butylene group and a 1,3-butylene group , 1,4-butylene group, 2,3-butylene group, 2,4-butylene group or 3,4-butylene group, preferably 1,2-propylene group, 1,3-propylene group, 2, It is more preferably a 3-propylene group or a 1,2-butylene group, and particularly preferably a 1,2-propylene group or a 2,3-propylene group.

The substituent that R ¹ may have in the formula (1) is the same as the substituent that L ¹ may have.
The ^R1 in the formula (1) is a linear or branched alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a direct group having 2 to 8 carbon atoms from the viewpoint of the adhesiveness of the obtained cured product. It is preferably a chain or a branched alkenyl group, or an alkynyl group having 2 to 8 carbon atoms, more preferably a linear or branched alkyl group having 1 to 8 carbon atoms, and a straight chain or a branched alkyl group having 1 to 6 carbon atoms. A branched alkyl group is more preferable, and a linear or branched alkyl group having 1 to 4 carbon atoms is particularly preferable. Further, the alkyl group is preferably a linear alkyl group.
Specifically, R ¹ in the formula (1) includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, an n-hexyl group and a 2-ethylhexyl group. Examples thereof include 1-octyl group, 2-octyl group, allyl group, phenyl group and benzyl group.
Of these, from the viewpoint of the adhesiveness of the obtained cured product, it is preferably a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, or an n-hexyl group, preferably a methyl group or an ethyl group. More preferably, it is a group, an n-propyl group, or an n-butyl group.

From the viewpoint of the adhesiveness of the obtained cured product, p in the formula (1) is preferably an integer of 2 to 6, more preferably an integer of 2 to 4, and further preferably 3 or 4. It is preferably 3, and particularly preferably 3. Further, p is preferably 3 or more from the viewpoint of the adhesiveness and flexibility of the obtained cured product.

Specific examples of the 2-cyanoacrylate compound represented by the formula (1) include 2- (2-methoxyethoxy) ethyl 2- (2-methoxyethoxy) ethyl and 2- (2-ethoxyethoxy) ethyl 2-cyanoacrylic acid. (2-Propyloxyethoxy) ethyl, 2- (2-butoxyethoxy) ethyl, 2- (2-pentyloxyethoxy) ethyl, 2- (2-hexyloxyethoxy) ethyl, 2- [2- (2-methoxy) Ethoxy) ethoxy] ethyl, 2- [2- (2-ethoxyethoxy) ethoxy] ethyl, 2- [2- (2-propyloxyethoxy) ethoxy] ethyl, 2- [2- (2-butyloxyethoxy) ethoxy ] Ethyl, 2- [2- (2-pentyloxyethoxy) ethoxy] ethyl, 2- [2- (2-hexyloxyethoxy) ethoxy] ethyl, 1- (2-methoxy-1-methylethoxy) propyl-2 -Il, 1- (2-methoxy-2-methylethoxy) propyl-2-yl, 2- (2-methoxy-2-methylethoxy) propyl-1-yl, 2- (2-methoxy-1-methylethoxy) ) Propyl-2-yl, 1- (2-ethoxy-1-methylethoxy) propyl-2-yl, 1- (2-ethoxy-2-methylethoxy) propyl-2-yl, 2- (2-ethoxy-) 2-Methylethoxy) propyl-1-yl, 2- (2-ethoxy-1-methylethoxy) propyl-2-yl, 1- (2-propoxy-1-methylethoxy) propyl-2-yl, 1-( 2-Propyl-2-methylethoxy) propyl-2-yl, 2- (2-propoxy-2-methylethoxy) propyl-1-yl, 2- (2-propoxy-1-methylethoxy) propyl-2-yl , 1- (2-butoxy-1-methylethoxy) propyl-2-yl, 1- (2-butoxy-2-methylethoxy) propyl-2-yl, 2- (2-butoxy-2-methylethoxy) propyl -1-yl, 2- (2-butoxy-1-methylethoxy) propyl-2-yl, 1- (2-hexyloxy-1-methylethoxy) propyl-2-yl, 1- (2-hexyloxy-) 2-Methylethoxy) propyl-2-yl, 2- (2-hexyloxy-2-methylethoxy) propyl-1-yl, 2- (2-hexyloxy-1-methylethoxy) propyl-2-yl,

1- [2- (2-Methyl-1-methylethoxy) -1-methylethoxy] propyl-2-yl, 1- [2- (2-methoxy-2-methylethoxy) -1-methylethoxy] propyl- 2-yl, 1- [2- (2-methoxy-1-methylethoxy) -2-methylethoxy] propyl-2-yl, 1- [2- (2-methoxy-2-methylethoxy) -2-methyl Ethoxy] propyl-2-yl, 2- [2- (2-methoxy-1-methylethoxy) -1-methylethoxy] propyl-1-yl, 2- [2- (2-methoxy-2-methylethoxy) -1-Methylethoxy] propyl-1-yl, 2- [2- (2-methoxy-1-methylethoxy) -2-methylethoxy] propyl-1-yl, 2- [2- (2-methoxy-2) -Methylethoxy) -2-methylethoxy] propyl-1-yl, 1- [2- (2-ethoxy-1-methylethoxy) -1-methylethoxy] propyl-2-yl, 1- [2- (2) -Ethoxy-2-methylethoxy) -1-methylethoxy] propyl-2-yl, 1- [2- (2-ethoxy-1-methylethoxy) -2-methylethoxy] propyl-2-yl, 1-[ 2- (2-ethoxy-2-methylethoxy) -2-methylethoxy] propyl-2-yl, 2- [2- (2-ethoxy-1-methylethoxy) -1-methylethoxy] propyl-1-yl , 2- [2- (2-ethoxy-2-methylethoxy) -1-methylethoxy] propyl-1-yl, 2- [2- (2-ethoxy-1-methylethoxy) -2-methylethoxy] propyl -1-yl, 2- [2- (2-ethoxy-2-methylethoxy) -2-methylethoxy] propyl-1-yl, 1- [2- (2-propoxy-1-methylethoxy) -1- Methylethoxy] propyl-2-yl, 1- [2- (2-propoxy-2-methylethoxy) -1-methylethoxy] propyl-2-yl, 1- [2- (2-propoxy-1-methylethoxy) 1- [2- (2-propoxy-1-methylethoxy) ) -2-Methylethoxy] propyl-2-yl, 1- [2- (2-propoxy-2-methylethoxy) -2-methylethoxy] propyl-2-yl, 2- [2- (2-propoxy-) 1-Methylethoxy) -1-methylethoxy] propyl-1-yl, 2- [2- (2-propoxy-2-methylethoxy) -1-methylethoxy] propyl-1-yl, 2- [2-( 2-propoxy-1-methylethoxy) -2 -Methylethoxy] propyl-1-yl, 2- [2- (2-propoxy-2-methylethoxy) -2-methylethoxy] propyl-1-yl,

1- [2- (2-Butoxy-1-methylethoxy) -1-methylethoxy] propyl-2-yl, 1- [2- (2-Butoxy-2-methylethoxy) -1-methylethoxy] propyl- 2-yl, 1- [2- (2-butoxy-1-methylethoxy) -2-methylethoxy] propyl-2-yl, 1- [2- (2-butoxy-2-methylethoxy) -2-methyl Ethoxy] propyl-2-yl, 2- [2- (2-butoxy-1-methylethoxy) -1-methylethoxy] propyl-1-yl, 2- [2- (2-butoxy-2-methylethoxy) -1-Methylethoxy] propyl-1-yl, 2- [2- (2-butoxy-1-methylethoxy) -2-methylethoxy] propyl-1-yl, 2- [2- (2-butoxy-2) -Methylethoxy) -2-methylethoxy] propyl-1-yl, 1- [2- (2-hexyloxy-1-methylethoxy) -1-methylethoxy] propyl-2-yl, 1- [2-( 2-Hexyloxy-2-methylethoxy) -1-methylethoxy] propyl-2-yl, 1- [2- (2-hexyloxy-1-methylethoxy) -2-methylethoxy] propyl-2-yl, 1- [2- (2-hexyloxy-2-methylethoxy) -2-methylethoxy] propyl-2-yl, 2- [2- (2-hexyloxy-1-methylethoxy) -1-methylethoxy] Propyl-1-yl, 2- [2- (2-hexyloxy-2-methylethoxy) -1-methylethoxy] propyl-1-yl, 2- [2- (2-hexyloxy-1-methylethoxy) -2-Methylethoxy] propyl-1-yl, 2- [2- (2-hexyloxy-2-methylethoxy) -2-methylethoxy] propyl-1-yl, tetrapropylene glycol monomethyl ether, tetrapropylene glycol mono Preferred examples include esters such as ethyl ether, tetrapropylene glycol monopropyl ether, tetrapropylene glycol monobutyl ether, tetrapropylene glycol monopentyl ether, and tetrapropylene glycol monohexyl ether.

As the 2-cyanoacrylate compound represented by the above formula (1) contained in the curable composition, only one kind may be used, or two or more kinds may be used in combination.
The content of the 2-cyanoacrylate compound represented by the above formula (1) in the curable composition is 40% by mass or more and 100% by mass with respect to the total mass of the curable composition from the viewpoint of adhesiveness and curability. It is preferably 50% by mass or more, 99.5% by mass or less, more preferably 60% by mass or more and 90% by mass or less, and 70% by mass or more and 85% by mass or less. Is particularly preferable.

<Other ingredients>
The curable composition which is the sealing agent of the present invention may contain other components other than the 2-cyanoacrylate compound represented by the above formula (1).
For example, tackifiers, stabilizers, curing accelerators, photopolymerization initiators, plasticizers, thickeners, particles, colorants, fragrances, solvents, strength improvers, rubber strengtheners, antioxidants, polymers, etc. Depending on the purpose, an appropriate amount can be blended within a range that does not impair the curability of the curable composition and the adhesiveness of the obtained cured product.
When the sealant of the present invention contains other components, it is preferable that it does not have the property of curing the 2-cyanoacrylate compound.
The content of the other components is preferably less than the content of the 2-cyanoacrylate compound, preferably 30% by mass or less, and preferably 20% by mass or less, based on the total mass of the curable composition. It is more preferable to have.

As the tackifier, rosin derivatives such as rosin ester, gum rosin, tall oil rosin, hydrogenated rosin ester, maleated rosin, and disproportionated rosin ester; mainly terpene phenol resin, α-pinene, β-pinene, limonene and the like. Examples thereof include terpene-based resins; (hydrogenated) petroleum resins; kumaron-inden-based resins; hydrogenated aromatic copolymers; styrene-based resins; xylene-based resins; (meth) acrylic-based polymers.

Examples of the plasticizing agent include triethyl acetyl citrate, tributyl acetyl citrate, dimethyl adipate, diethyl adipate, dimethyl sebacate, dimethyl phthalate, diethyl phthalate, dibutyl phthalate, diisodecyl phthalate, dihexyl phthalate, and phthalate. Diheptyl acid, dioctyl phthalate, bis (2-ethylhexyl) phthalate, diisononyl phthalate, diisotridecyl phthalate, dipentadecyl phthalate, dioctyl terephthalate, diisononyl isophthalate, decyl torulate, bis succinate (2-ethylhexyl), 2 -Examples include ethylhexylcyclohexylcarboxylate, diisobutyl fumarate, diisobutyl maleate, triglyceride caproate, 2-ethylhexyl benzoate, dipropylene glycol dibenzoate and the like. Among these, tributyl acetylcitrate, dimethyl adipate, dimethyl phthalate, 2-ethylhexyl benzoate, dipropylene glycol di from the viewpoint of good compatibility with 2-cyanoacrylate compounds and high plasticization efficiency. Benzoate is preferred. Only one kind of these plasticizers may be used, or two or more kinds thereof may be used in combination.

As the rubber strengthening agent, a known rubber strengthening agent can be used, and among them, ethylene acrylic acid elastomer is preferably mentioned. As the ethylene acrylic acid elastomer, for example, a VAMAC elastomer manufactured by DuPont can be used.
The rubber toughening agent is preferably 1.5% by mass to 20% by mass, more preferably 5% by mass to 15% by mass, and 8% by mass to 10% by mass with respect to the total mass of the curable composition. % Is particularly preferable.

As the antioxidant, a known antioxidant can be used, and among them, a hindered phenol compound is preferably mentioned.

The polymer may be a homopolymer (homopolymer) or a copolymer (copolymer), and a copolymer is preferable.
Specific examples of the polymer include poly (meth) acrylate, polyvinyl ether, natural rubber, polyisoprene, polybutadiene, polyisobutylene, polychloroprene, butadiene acrylonitrile polymer, thermoplastic elastomer, styrene-isoprene, styrene isoprene-styrene block copolymer, and ethylene. Examples thereof include polymers selected from the group consisting of -propylene-diene polymers, styrene-butadiene polymers, poly-α-olefins, silicones, ethylene-containing copolymers, ethylene vinyl acetates, and combinations thereof. Of these, poly (meth) acrylate or ethylene vinyl acetate copolymer is preferable.

Stabilizers include (1) aliphatic sulfonic acids such as sulfur dioxide and methanesulfonic acid, aromatic sulfonic acids such as p-toluenesulfonic acid, trifluorination of boron trifluorinated methanol, boron trifluorinated diethyl ether and the like. Examples thereof include anionic polymerization prohibiting agents such as boron complex, HBF ₄ , trialkylborate, and (2) radical polymerization prohibiting agents such as hydroquinone, hydroquinone monomethyl ether, t-butylcatechol, catechol and pyrogallol. Only one of these stabilizers may be used, or two or more of these stabilizers may be used in combination.

As the curing accelerator, any one that promotes anionic polymerization of the 2-cyanoacrylate-based curable composition can be used. Examples of the curing accelerator include polyether compounds, calix allenes, thia calix allenes, pyrogallol allenes, onium salts and the like. Only one kind of these curing accelerators may be used, or two or more kinds thereof may be used in combination.

Examples of the thickener include polymethyl methacrylate, a copolymer of methyl methacrylate and an acrylic acid ester, a copolymer of methyl methacrylate and another methacrylic acid ester, acrylic rubber, polyvinyl acetate, and polyvinyl chloride. Examples thereof include polyurethane resin, polyamide resin, polystyrene, cellulose ester, polyalkyl-2-cyanoacrylic acid ester, and ethylene-vinyl acetate copolymer. Only one of these thickeners may be used, or two or more of these thickeners may be used in combination.

The particles that may be blended into the curable composition are for adjusting the thickness of the adhesive layer when the curable composition is used.
The average particle size of the particles is preferably 10 μm to 200 μm, more preferably 15 μm to 200 μm, and even more preferably 15 μm to 150 μm.
The material of the particles is not particularly limited as long as it is insoluble in the 2-cyanoacrylate compound used and does not cause deterioration such as polymerization. For example, thermoplastic resins such as polyethylene, polypropylene, polymethylpentene, acrylic resin, polyvinyl chloride, polytetrafluoroethylene, polyethylene terephthalate, polybutylene terephthalate, polysulfone, polyphenylene oxide; unsaturated polyester, divinylbenzene polymer, divinylbenzene. -Cross-linked resin such as styrene copolymer, divinylbenzene- (meth) acrylic acid ester copolymer, diallyl phthalate polymer; inorganic compounds such as spherical silica, glass beads, glass fiber; silicone compound; organic polymer skeleton and polysiloxane Examples thereof include organic-inorganic composite particles containing a skeleton.
The content of the particles is not particularly limited, but when the content of the 2-cyanoacrylate compound is 100 parts by mass, it is preferably 0.1 part by mass to 10 parts by mass, and 1 part by mass to 5 parts by mass. It is more preferably 1 part by mass to 3 parts by mass. When it is in the range of 0.1 part by mass to 10 parts by mass, the influence on the curing speed and the adhesive strength can be reduced.
The average particle size of the particles in the present invention is a volume-based average value measured by a laser diffraction type particle size distribution measuring device.

<How to use the sealant>
The method of using the sealant of the present invention is not particularly limited as long as it is a method of causing a polymerization reaction of a 2-cyanoacrylate compound to cure it. For example, it may be cured by moisture such as humidity, or it may be cured by adding a photopolymerization initiator and light, but it is preferably cured by moisture such as moisture.

The sealant of the present invention can be used for the purpose of filling the gaps of all members. The method of filling the gap of the member with a sealing agent is not particularly limited, and for example, a dispenser, a spatula, a trowel or the like may be used.
The sealant of the present invention may be used to fill gaps between members of the same material or may be used to fill gaps between members of different materials.
If necessary, a treatment for reducing the adhesiveness of the surface of the sealing agent after curing may be performed, or a primer agent or the like may be used in combination.

<Article>
The article of the present invention is an article comprising a member and a cured product of the above-mentioned sealing agent that fills the gaps of the member.
Examples of the material of the member include plastic, rubber, wood, metal, inorganic material, paper and the like.
Specific examples of the plastic include polyolefin resins such as polypropylene and polyethylene, polyacetal resins, fluororesins such as polytetrafluoroethylene (PTFE), polyvinyl alcohol, cellulose acetate resins such as triacetyl cellulose and diacetyl cellulose, and acrylic resins. Polyester resins such as polyethylene terephthalate, polycarbonate, and polyarylate, cyclic polyolefin resins using cyclic olefins such as polyether sulfone and norbornene as monomers, polyvinyl chloride, epoxy resins, polyurethane resins, polyamide resins, polyimide resins, and polystyrene resins are available. Can be mentioned.
Specific examples of the rubber include ethylene propylene diene rubber (EPDM), silicone rubber, natural rubber, styrene butadiene rubber (SBR) and the like.
Specific examples of wood include natural wood and synthetic wood.
Specific examples of the metal include steel plates, metals such as aluminum and chromium, and metal oxides such as zinc oxide (ZnO) and indium tin oxide (ITO).
Specific examples of the inorganic material include glass, mortar, concrete, stone, ceramics, semiconductors and the like.
Specific examples of the paper include high-quality paper, coated paper, art paper, imitation paper, thin paper, thick paper and other papers, and various synthetic papers.
Above all, since the sealing agent of the present invention has excellent adhesiveness to the resin member, it can be particularly preferably used as a sealing agent for filling the gap between the resin members.

The type of the member included in the article may be only one type or two or more types.
The type of the article is not particularly limited, and examples thereof include electronic parts, home appliances, medical supplies, arts and crafts, containers, packaging bags, furniture, and buildings (joints, walls, etc.).

Hereinafter, the present invention will be specifically described based on examples. The present invention is not limited to these examples. Further, in the following, "parts" and "%" mean "parts by mass" and "% by mass", respectively, unless otherwise specified.

(Examples 1 to 4 and Comparative Example 1)
The 2-cyanoacrylate compound shown in Table 1 or Table 2 was used as a curable composition.
Using the obtained curable composition, the following physical property values were measured and evaluated. The evaluation results are shown in Table 1 or Table 2.

<Measurement of glass transition temperature and storage elastic modulus of cured product>
The glass transition temperature (Tg) and storage elastic modulus of the cured product of the curable composition were measured by the following methods.
After injecting the curable composition between the jigs for the following dynamic viscoelasticity measuring device coated with triethanolamine, the frequency is used using the dynamic viscoelasticity measuring device (manufactured by Anton Pearl Co., Ltd., product name "MCR301"). The storage elastic modulus was measured under the conditions of 1 Hz, a temperature of 25 ° C., and a thickness of 300 μm. A cured product was used after confirming that the change in storage elastic modulus had disappeared. Using the cured product, the storage elastic modulus (E'), loss elastic modulus (E "), and loss tangent (tan δ = E) due to shearing in the range of -50 ° C to 100 ° C at a frequency of 1 Hz and a temperature rise rate of 2 ° C / min. "/ E') was measured. The glass transition temperature (Tg) was determined by using the peak temperature of the loss tangent (tan δ) as an evaluation index. The storage elastic modulus used the value at 23 ° C.

<Measurement of tack value in probe tack test of cured product>
A 38 μm thick spacer (removable polyethylene terephthalate (PET) film (manufactured by Toyobo Film Solution Co., Ltd., product name “Purex A31”)) with a punched frame and a 125 μm thick easy-adhesive PET film (Toray (Toray) The adhesive composition was dropped into a spacer frame by placing it on a product name "Lumirror 125U34") manufactured by Co., Ltd. Another release PET film coated with triethanolamine was put on it and laminated, and the mixture was allowed to stand at room temperature (25 ° C., the same applies hereinafter) for 24 hours to be completely cured. After curing, it was cut into a width of 15 mm and a length of 15 mm, and the release PET film was peeled off to obtain a test piece. Regarding this test piece, ASTM D2979: 2016 (partially compliant), Japanese Pharmacopoeia 6.12. (3.4.): Measured using a probe tack tester (manufactured by Tester Sangyo Co., Ltd., product name "TE-6002") in accordance with the 17th revised "Probe Tack Test Method", and the tack value (tack value () Unit: N / cm ² ) was calculated.

<Stress of hardened material-Measurement of elongation in strain curve>
1 μL of triethanolamine was added to 1 g of the curable composition, and after stirring, a silicone having a thickness of 1 mm was placed on a release PET film (manufactured by Toyobo Film Solution Co., Ltd., product name “Purex A31”). It was poured into a rubber mold. A release film was put on top of the film, sandwiched between glass plates, and allowed to stand at room temperature for 24 hours to completely cure. After curing, the mold and the release film were removed to prepare a cured product having a width of 5 mm, a length of 50 mm, and a thickness of 1 mm. The stress-strain curve of this cured product was measured using a tensile tester (manufactured by Toyo Seiki Seisakusho Co., Ltd., product name "Strograph V20-C"), and the elongation rate was calculated.

<Viscosity of curable composition>
The viscosity of the curable composition was measured using an E-type viscometer manufactured by Tokimec Co., Ltd. under the conditions of 25 ° C. and 100 rpm.

<180 ° peel strength test of adhesive>
-Preparation of adhesive between glass and easy-adhesive PET base material-
A 38 μm-thick spacer (release PET film (manufactured by Toyobo Film Solution Co., Ltd., product name “Purex A31”)) with a punched frame 25 mm wide and 150 mm long is mounted on a glass plate (AGC fabric) with a thickness of 1 mm. It was placed on a product (product name "FL11AK") manufactured by Tech Co., Ltd., and the obtained curable composition was dropped onto the glass in the spacer frame. A 125 μm-thick easy-adhesive PET film coated with triethanolamine (manufactured by Toray Industries, Inc., product name “Lumilar 125U34”) was placed on top of it, and the film was allowed to stand at room temperature for 24 hours to completely cure. I let you. After curing, the spacer was removed to prepare a test piece having an adhesive layer having a thickness of 38 μm, a width of 25 mm, and a length of 150 mm, one side being a glass base material and the other side being an easy-adhesion PET base material.

-Making an adhesive between aluminum substrates-
A 38 μm-thick spacer (release PET film (manufactured by Toyobo Film Solution Co., Ltd., product name “Purex A31”)) with a 90 mm wide and 150 mm long punched frame is attached to a 0.1 mm thick aluminum plate. (Material specified in JIS A6061P) was placed, and the adhesive composition was dropped onto an aluminum plate in a spacer frame. A 1 mm-thick aluminum plate coated with triethanolamine was put on it and bonded, and the mixture was allowed to stand at room temperature for 24 hours to be completely cured. After curing, the spacer was removed and cut to a width of 25 mm to prepare a test piece having an adhesive layer having a thickness of 38 μm, a width of 25 mm and a length of 150 mm, and having an aluminum substrate on both sides.

-Measurement of peel strength-
For the test piece prepared under the above conditions, the end of the base material on one side (the easy-adhesive PET base material in the case of an adhesive between the glass and the easy-adhesive PET base material), and the aluminum base materials at a speed of 50 mm / min. The glass and the easy-adhesive PET base material are peeled off at a speed of 100 mm / min in the peeling direction of 180 °, and the 180 ° peeling adhesive force (resistance) (unit: N / 25 mm) to the adherend at that time is measured. bottom.

In the chemical structural formulas of Tables 1 and 2, Me represents a methyl group, Bu represents an n-butyl group, and C ₃ H ₆ O represents -CH (CH ₃ ) CH ₂ O- and-. CH ₂ Represents a mixed group of CH (CH ₃ ) O−. The 2-cyanoacrylate compound used in Example 1 is a mixture of position and optical isomers.
Further, FIG. 1 shows the elongation rate in the stress-strain curve of the cured product of Examples 2 to 4 and Comparative Example 1.
The vertical axis of FIG. 1 represents stress (stress, unit: N / mm ² ), and the horizontal axis represents strain (strain = elongation rate, unit:%).
The details of the abbreviations in FIG. 1 are as follows: ME3CA: methoxyethoxyethoxyethyl cyanoacrylate (Example 2).
MEECA: Methoxyethoxyethyl cyanoacrylate (Example 3)
BEECA: Butoxyethoxyethyl cyanoacrylate (Example 4)
EECA: ethoxyethyl cyanoacrylate (Comparative Example 1)

As shown in Table 1, the curable compositions of Examples 1 to 4 were able to be superior in the adhesiveness of the obtained cured product as compared with the curable composition of Comparative Example 1.
Further, as shown in Tables 1 and 2, the curable compositions of Examples 1 to 4 were excellent in the curing rate and also in the flexibility of the obtained cured product.

The sealant of the present invention can be used to fill gaps between any member. In addition, it is easy to handle because it cures quickly after filling.

Claims (12)

It is a curable composition and
It contains a 2-cyanoacrylate compound represented by the following formula (1).
A sealing agent, which is a curable composition having a storage elastic modulus of 1.0 × 10 ⁴ Pa or more and 1.0 × 10 ⁸ Pa or less at 23 ° C. of the cured product of the curable composition.

In formula (1), L ¹ independently represents a linear or branched alkylene group having 2 to 6 carbon atoms which may have a substituent, p represents an integer of 2 to 8, and R ¹ represents a substituent. It represents a linear or branched alkyl group having 1 to 8 carbon atoms, an aryl group, an alkenyl group, or an alkynyl group which may have a group. The sealing agent according to claim 1, wherein the cured product of the curable composition has a glass transition temperature of 60 ° C. or lower. The sealant according to claim 1 or 2, wherein the tack value in the probe tack test of the cured product of the curable composition is 0.1 N / cm ² or more and 100 N / cm ² or less. The sealant according to any one of claims 1 to 3, wherein the elongation rate of the cured product of the curable composition in the stress-strain curve is 350% or more. 180 ° peeling adhesive strength of the adhesive obtained by curing and adhering the curable composition to glass and an easily adhesive polyethylene terephthalate substrate measured in accordance with JIS Z 0237 (2009) is 5N / 25 mm or more. The sealing agent according to any one of claims 1 to 4, which is 100 N / 25 mm or less. The 180 ° peeling adhesive strength of the adhesive obtained by curing and adhering the curable composition between aluminum substrates measured in accordance with JIS Z 0237 (2009) is 5N / 25mm or more and 50N / 25mm or less. , The sealing agent according to any one of claims 1 to 5. The L ¹ is independently -CH ₂ CH _2- , -CH (R ² ) CH _2- or -CH ₂ CH (R ² )-, and R ² is an alkyl group having 1 to 6 carbon atoms. , The sealing agent according to any one of claims 1 to 6. The sealing agent according to any one of claims 1 to 7, wherein p is an integer of 2 to 6. The sealing agent according to any one of claims 1 to 8, wherein R ¹ is a linear or branched alkyl group having 1 to 6 carbon atoms. The initial viscosity of the curable composition at 25 ° C. is 300 Pa · s or less.
In an environment of 25 ° C. and 60% RH, the storage elastic modulus of the cured product of the curable composition is 1.0 from the time when 1 μL of an acetone solution of 5% by volume triethanolamine is added to 0.1 g of the curable composition. The sealing agent according to any one of claims 1 to 9, wherein the time required to become substantially constant in the range of × 10 ⁴ Pa or more and 1.0 × 10 ⁸ Pa or less is 60 minutes or less. The sealing according to any one of claims 1 to 10, further comprising at least one compound selected from the group consisting of a tackifier, a plasticizer, a rubber strengthening agent, an antioxidant, and a polymer. Agent. An article comprising a member and a cured product of the sealing agent according to any one of claims 1 to 11, which fills the gap of the member.

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