KR20070039880A - Photocurable composition - Google Patents

Abstract

The photocurable composition which consists of hydrogenated polybutadiene which has a (meth) acryloyl group at the (A) terminal, (B) saturated aliphatic hydrocarbon type elastomer, and (C) photoinitiator shows the outstanding performance as an elastic sealing agent.

Seal

Description

Photocurable composition {PHOTOCURABLE COMPOSITION}

The present invention relates to a curable composition, and particularly to a photocurable composition which polymerizes rapidly by irradiation of active energy rays such as ultraviolet rays and visible light and is useful as an elastic sealant for various members.

As a method of assembling and sealing electric / electronic device parts, automobile parts, optical device parts, various mechanical parts, and the like, conventionally, a method of contact welding by interposing a molding gasket made of rubber or the like between the sealing surfaces and a liquid phase The method of sealing by interposing a sealant between sealing surfaces is adopted. Among these methods, the molding gasket has a problem such as high material loss due to punching and a high molding processing cost of the gasket, and long-term use of the gasket weakens durability and causes bolt tightening torque down and slippage. There is a problem. In addition, while applying an anaerobic liquid seal agent mainly composed of a room temperature curable silicone material (silicon RTV) or urethane (meth) acrylate, which is cured by reacting with moisture in the air on the flange surface, it is different as it is. The method of sticking and sealing is also used. However, these cannot be said that the hardening time of the sealant after sticking is enough, and the so-called initial-pressure-resistant fall that the uncured liquid sealant flows out by internal pressure and becomes a problem becomes a problem. In order to solve the said problem, in recent years, the method of hardening | curing rapidly by light and forming a sealing agent composition has been proposed and used variously.

As such a photocurable resin composition, the thing of various types is known.

Examples thereof include a polyfunctional (meth) acrylic acid ester, a bifunctional (meth) acrylic acid ester having a crosslinked ring structure, and a photocurable composition (Patent No. 2953598) comprising a photopolymerization initiator, a (meth) acryl group in a molecule thereof. Polyisobutylene having a hydrolyzable group, a light and moisture curable composition comprising a photopolymerization developer and a moisture curing catalyst (JP-A No. 2000-178535) Epoxy resin, rubbery polymer fine particles, inorganic filler, heat latent epoxy curing agent and high softening point Thermosetting compositions comprising polymer fine particles (JP-A No. 2000-347203), urethane (meth) acrylate (meth) acrylic ester monomers, photopolymerization initiators, and photocurable sealant compositions mainly comprising fillers (Japanese Patent Application Laid-Open No. 2001-163931). .

It is preferable that the sealing agent is generally excellent in solvent resistance, moisture barrier properties, etc., while maintaining the sufficient flexibility of the cured product and not impairing its function even under severe conditions such as high temperature.

Disclosure of the Invention

Purpose of the Invention

An object of the present invention is to provide a curable composition exhibiting excellent performance as a sealant.

Still another object of the present invention is that the cured product is particularly excellent in solvent resistance, moisture permeability barrier property, flexibility and impact resistance, and is a liquid crystal display device, an organic EL device, a dye-sensitized solar cell, an electronic paper, a lithium ion battery, a poriacene battery. And photocurable resin compositions particularly useful as sealing agents for oxylide batteries, capacitors, fuel cells and the like.

It is still another object of the present invention to provide a photocurable resin composition which is particularly useful as a sealant of a member whose cured product has a sufficient sealing function even under a high temperature condition and is easily susceptible to high heat such as an automobile engine part.

Summary of the Invention

The present invention is (a) a hydrogenated polybutadiene having a (meth) acryloyl group, (B) a saturated aliphatic hydrocarbon-based elastomer, and (C) a photopolymerization initiator. It is a chemical composition.

The present invention is the second,

General formula of component (A):

(Wherein, R ¹ and R ² each independently represent a hydrogen atom or a methyl group, R ³ and R ⁴ each independently represent a simple linking group, an oxygen atom or a divalent organic group having 1 to 16 carbon atoms, and x: y = 0 100: 100-0, n is 15-150), It is said 1st photocurable composition.

This invention is the said 1st and 2nd photocurable composition which contains (D) chain aliphatic or alicyclic monofunctional (meth) acrylate more than 3rd furthermore.

In the fourth aspect of the present invention, the component (B) is 20 to 80 parts by weight, the component (C) is 0.5 to 5 parts by weight and the component (D) is 0 to 80 parts by weight based on 100 parts by weight of the component (A). It is the said 1st-3rd photocurable composition which is the following.

This invention is the said 1st-4th photocurable composition which is at least 1 sort (s) selected from hydrogenated polybutadiene and polyisobutylene in 5th.

This invention is the said, 1st-5th photocurable composition in which (B) component has the molecular weight of 5,000 or less in 6th.

This invention is the said 1st and 2nd invention which the (B) component is polyisobutylene of molecular weight 500-50,000 in 7th, and (A) component is 20-60 weight part with respect to 100 weight part of (B) component. Photocurable composition.

This invention is the said 7th photocurable composition of Claim 8 whose compressive permanent distortion of 150 degreeC is 20% or less in JISK6262 test of the hardened | cured material of a photocurable composition.

The ninth aspect of the present invention provides the general formula of the component (B):

(R l, R 2 는 알킬기 또는 알케닐기를 나타내고, m은 8 ~ 800을 나타낸다.)

(R 1 and R 2 represent an alkyl group or an alkenyl group, and m represents 8 to 800.)

It is the said 7th and 8th photocuring compositions which are polyisobutylene shown by the following.

This invention is tenth, The said 7th-9th photocurable composition whose molecular weight of (B) component is 2,000-50,000.

The present invention is characterized by applying the photocurable composition of any of the first to the tenth to a solid substrate to be bonded and sealed to eleventh, and curing the composition by irradiating with light. It is a sealing method to use.

Embodiment of invention

(A) component of the curable composition of this invention is hydrogenated polybutadiene which has a (meth) acryloyl group. The term "(meth) acryloyl group" here means acryloyl group and / or methacryloyl group.

The component (A) has a polybutadiene skeleton in which the main skeleton is hydrogenated (hydrogenated) as a molecular structure, and has a (meth) acryloyl group at its terminal, and is directly or appropriate with the hydrogenated polybutadiene molecule and the (meth) acryloyl group. It is bound to a divalent bond group. A typical example thereof is shown in the general formula (1) above. The hydrogenated butadiene units constituting the repeating unit of hydrogenated polybutadiene of the main skeleton may be hydrogenated l, 2-butadiene unit alone, hydrogenated l, 4-butadiene unit alone, or a combination of both. (That is, ｘ: ｙ = 0 to 100: 100 to 0) is preferably hydrogenated l, 2-butadiene unit hydrogenated l, 4-butadiene unit (xy) = 10 to 100: 90 to 0, particularly 20 95: 80: 5 combination system is preferable. The component (A) is usually polymerized by butadiene by anionic polymerization using a sodium catalyst or cation polymerization using a Friedel-Crafts catalyst to form a liquid polybutadiene, and in the presence of a hydrogenation catalyst such as a transition metal. It is a liquid substance manufactured by adding a (meth) acryloyl group to the terminal after hydrogenation, It can select from a commercial item suitably, and can use.

The saturated aliphatic hydrocarbon elastomer of component (B) refers to an elastomer in which the main skeleton is saturated aliphatic hydrocarbon, and the terminal of the molecule may be an unsaturated group such as an allyl group depending on the production method or the like. It is preferable that (B) component is excellent in compatibility with (A) component, and shows rubber elasticity also at normal temperature, and especially hydrogenated polybutadiene and polybutylene are preferable.

As a photoinitiator of (C) component, generally known radical photopolymerization initiator can be used suitably. Such photoinitiators are classified into an intramolecular cleavage type (P1 type) and a hydrogen extraction type (P2 type) by the difference in chemical structure (molecular bond enel group). Specific examples of the Pl type include 4-phenoxydichloroacetphenone, 4-t-butyldichloroacetphenone, 4-t-butyltrichloroacetphenone, diethoxyacetphenone, 2-hydroxy-2-methyl-l-phenyl Propane-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-l-one, 1- (4-dodecylphenyl) -2-hydroxy-2-methylpropane- Acetphenones such as 1-one, 4- (2-hydroxyethoxy) -phenyl (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, benzoin, benzoin methyl ether, Benzoin, such as benzoin ethyl ether and benzyl dimethyl ketal, an acylpocipine oxide, a titanocene compound, etc. are mentioned. Moreover, as a specific example of P <2> type, benzophenone, benzoyl benzoic acid, benzoyl benzoic acid methyl ether, 4-phenyl benzophenone, hydroxy benzophenone, 4-benzol-4'- methyl diphenyl sulfide, 3, 3 Such as benzophenones such as' -methyl-4-methoxy benzophenone, thioxanthone, 2-chlorothioxanthone, 2-methyl thioxanthone, 2,4-dimethyl thioxanthone and isopropyl thioxanthone Thioxanthones; and the like. An optical radical polymerization initiator may be used by 1 type, or may use 2 or more types together, and may use PI types, P2 types, or P1 type and P2 type together.

The amount of the photopolymerization initiator may be used in an amount sufficient to perform photopolymerization, preferably 0.1 to 10 parts by weight, in particular 0.5 to 5 parts by weight, per 100 parts by weight of the resin component in the composition.

Component (D) is a linear aliphatic or alicyclic monofunctional (meth) acrylate monomer having a single minor number of 5 or more, and the linear carbon of the aliphatic chain portion preferably has 5 to 20 carbon atoms, and 8 to 8 16 is more preferable. The monofunctional (meth) acrylate used in the present invention is not suitable for structures having polarities such as hydroxyl groups and amino groups. Therefore, it is preferable that the chain aliphatic which is an ester part and an alicyclic part become a hydrocarbon. Specific examples of the chain aliphatic monofunctional (meth) acrylate monomers include 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate and disil. (Meth) acrylate, dodecyl (meth) acrylate, stearyl (meth) acrylate, hexadiyl (meth) acrylate, etc. are mentioned. Moreover, as a specific example of an alicyclic (meth) acrylate component, cyclohexyl (meth) acrylate, norbornyl (meth) acrylate, a dicyclopentanyl (meth) acrylate, a dicyclopentenyl (meth) acrylate, iso Boronyl (meth) acrylate etc. are mentioned.

You may mix | blend suitably the other additive with the photocurable composition of this invention in the range which does not impair the characteristic of the resin composition of this invention. Examples of other additives include colorants such as sensitizers, pigments and dyes, polymerization inhibitors, eye drops, antifoaming agents, coupling agents, organic and inorganic fillers, and the like.

The photocurable composition of the present invention is suitably used as a sealant in various fields by applying to a substrate to be bonded as a liquid sealant and irradiating and curing it by a conventional method, but depending on the required properties of the sealant, It is preferable to select the amount.

In the first aspect, the cured product is excellent in solvent resistance, moisture permeability barrier property, flexibility and impact resistance, so that the liquid crystal display device, the organic EL device, the dye-sensitized solar cell, the electronic paper, the lithium ion battery, the poriacene battery, the oxylide It is a photocurable composition especially useful as a sealing agent of a battery, a capacitor, a fuel cell.

In this case, with respect to 100 weight part of (A) component, (B) component is 20-80 weight part, (C) component is catalyst amount, especially 0.5-5 weight part, (D) component 0-80 weight part, More preferably, the compounding ratio of 20-60 weight part is preferable, and it is preferable to use the low molecular weight whose molecular weight is 500-5,000 as (A) component.

When the photocurable composition of this 1st aspect is used as a sealing agent in the use which can give the hardened | cured material which combined solvent resistance, moisture permeability barrier property, flexibility, and impact resistance, and can be adhere | attached with a dye-sensitized solar cell etc., a heat cycle This can be followed by expansion and contraction of the adherend, and the stress generated on the adhesive interface can be absorbed and alleviated. When the component (D) is used in combination, furthermore, it is possible to use very suitably for the site where the surface of the CIPG or the sealing agent is opened due to the reduction of the surface tuckiness at the time of curing.

A 2nd aspect is the photocurable composition which hardened | cured material has a sufficient sealing function even under high temperature conditions, and is especially useful as a sealing agent of the member which is easy to catch high heat, such as an automobile engine part.

In this case, a composition becomes (A) component-(C) component, (B) component is polyisobutylene of molecular weight 500-50,000, Preferably 2,000-50,000, with respect to 100 weight part of (B) component It is preferable that (A) component is 20-60 weight part and (C) component is a catalyst amount, especially the mixing ratio of 0.5-5 weight part.

Typical examples of polyisobutylene are represented by the above general formula (2), and can be appropriately selected from commercially available products.

The composition of this 2nd aspect can provide the elastic seal agent whose hardened | cured material has 20% or less of compression set at 150 degreeC in JISK6262 test, and is especially effective for the sealing of members which require heat resistance, such as an automobile engine part. Is used.

The present invention will be described in detail with reference to the following examples, but the present invention is not limited by the following examples.

Embodiments of the first aspect:

The used material is as follows. As a hydrogenated polybutadiene (A) which has a (meth) acryloyl group at the terminal, "TEAI1000" (made by Nippon Sodatsu Co., Ltd.), "SPBDA" (made by Osaka Yuki Co., Ltd.), and "TEAl000" as a comparison of a component (A) Un hydrogenated polybutadiene having a (meth) acryloyl group at the terminal made by Sodatsu Corporation) `` UE8200 '' (epoxy acrylate made by Dainippon Ink, Inc.), `` UE800l '' (urethane acrylate made by Kyoeisha Chemical Co., Ltd.), saturated aliphatic elastomer As (B) hydrogenated polybutadiene ("BI2000": Nippon Sodatsu Co., Ltd.), polyisobutylene ("G1000" and "G3000": a non-hydrogenated polybutadiene "BI2000" as a comparison of BASF Japan company, component (C): Nippon Sodatsu Co., Ltd.), polyisoprene (LIR-30): Kuraray Co., Ltd., "Irgacure" 184 (# 184, Chiba Specialty Chemicals Co., Ltd.), carbon number as a photoinitiator (C) Is 5 or more chain aliphatic and alicyclic monofunctional (meth) acrylate component (D) N-butylacrylate (n-BA), 2-hydroxyethyl acrylate as a comparison of isobornyl acrylate (IBXA), isononyl acrylate (INA), lauryl acrylate (LA), component (D) (HEMA) N, N-dimethylaminoethyl methacrylate (DMMA).

These materials were mix | blended as shown to Tables 1-3 (the compounding quantity described in a table means a weight part), and it stirred at 50 degreeC using the mixer for 1 hour, and obtained each composition. Each obtained composition was evaluated in accordance with each test method shown below, and the meaning was combined with Table 1-Table 3, and was described.

Compatibility Test

The compatibility was confirmed by putting about 20 g of each composition based on the Example and the comparative example into a 50 mL glass bottle, visually confirming the separation state after standing at 25 ° C. for 24 hours, and determining that no separation was detected as × and separation.

[Hardness test]

The resin hardness was placed in a polycap of 25 φ about 2 g of each composition based on the Examples and Comparative Examples, cured by irradiating ultraviolet light at 3000 mJ / cm 2, measuring five arbitrary points with a hardness tester (Tyrometa Type A), and making the average of the values. . The target value was 50 or less.

Solvent Resistance Test

About 2 g of each composition based on an Example and a comparative example was put into the polycap of 25 phi, it irradiated with ultraviolet-ray 3000mJ / cm <2>, and it hardened | cured, and the hardened | cured material for the acetonitrile was immersed after weight measurement (condition: 60 degreeCx 96 hours). Then, the hardened | cured material was taken out, it wiped lightly on the surface, the weight was measured, and the weight change rate before immersion was calculated | required. The target value was set to ± 15% or less by weight fraction.

[Water vapor transmission test]

The measurement was performed based on JIS Z 0208 (measurement condition: 60 degreeC x 95% RH).

The measurement film was made by coating a resin on a polyfluorinated ethylene plate (about 100 microns of film thickness), cutting the cured product by irradiating ultraviolet light at 3000 mJ / cm 2, and cutting it into a designated container shape, and curing calcium chloride in about 1 g of container. . The measurement was based on the weight after 24 hours, and made into the end point the time after which a weight change was saturated over time. The target value was 80 g / cm 2 · 24h.

Table 1

Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 TEAI1000 100 100 100 100 100 100 100 SPBDA 100 TEA1000 UF8001 UE8200 G1000 20 40 50 60 80 50 G3000 50 BI2000 50 EP600A LIR-30 Irgacure184 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 Compatibility ○ ○ ○ ○ ○ ○ ○ ○ Hardness (A) 50 42 33 27 19 32 27 30 Solvent resistance (%) 14.7 12.5 9.1 5.2 4.7 7.1 11.0 10.1 Water vapor permeability (g / ㎠ · 4h) 54.0 49.4 48.7 44.4 37.9 53.2 27.2 68.0

Table 2

Example 9 Example 10 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 TEAI1000 100 100 100 SPBDA TEA1000 100 UF8001 100 UE8200 100 G1000 15 85 50 50 50 G3000 BI2000 EP600A LIR-30 50 Irgacure 184 2.5 2.5 2.5 2.5 2.5 2.5 Compatibility ○ ○ ○ × × × Hardness (A) 67 18 48 - - - Solvent resistance (%) 27.7 6.4 18.2 - - - Water vapor permeability (g / ㎠ · 4h) 66.7 118.8 198.8 - - -

As shown in Tables 1 and 2, in the case of the non-hydrogenated polybutadiene having a (meth) acryloyl group at both ends, the solvent resistance and the moisture permeability are both sufficient in comparison with the case of the hydrogenated polybutadiene having a main chain. Can't. On the other hand, when a polymer main chain is urethane acrylate or an epoxy acrylate, compatibility with (B) component worsens. If there is little saturated aliphatic elastomer, solvent resistance will fall, and too much, moisture permeability will fall. Moreover, compatibility becomes poor in the polyisopropene whose main chain of a saturated aliphatic elastomer consists of a C5 repeating unit.

Table 3

Example 11 Example 12 Example 13 Example 14 Example 15 Example 16 TEAI1000 100 100 100 100 100 100 SPBDA TEA1000 UF8001 UE8200 IBXA 25 50 75 50 INA 50 LA 50 n-BA HEMA DMMA G1000 50 50 50 50 50 G3000 50 Irgacure184 2.5 2.5 2.5 2.5 2.5 2.5 Compatibility ○ ○ ○ ○ ○ ○ Hardness (A) 35 47 66 35 22 20 Solvent resistance (%) 5.0 6.4 9.2 14.0 9.8 10.1 Water vapor permeability (g / ㎠ · 4h) 43.9 43.9 43.5 59.8 77.9 71.9

Comparative Example 5 Comparative Example 6 Comparative Example 7 Comparative Example 8 TEAI1000 100 100 100 100 SPBDA TEA1000 UF8001 UE8200 IBXA 85 INA LA n-BA 50 HEMA 50 DMMA 25 G1000 50 50 50 25 G3000 Irgacure184 2.5 2.5 2.5 2.5 Compatibility ○ ○ ○ × Hardness (A) 80 30 56 - Solvent resistance (%) 14.1 18.9 6.7 - Moisture permeability (g / cm 2 · 4h) 36.2 86.6 88.1 -

As shown in Table 3, when 80 or more parts by weight of a chain aliphatic or alicyclic monofunctional (meth) acrylate having 5 or more carbon atoms is added to the component (A), solvent resistance and moisture permeability are excellent, but flexibility cannot be obtained. Moreover, when carbon number (meth) acrylate component of less than 5 is added, compatibility of resin will worsen and moisture permeability will also fall.

Embodiment of the second aspect:

The material used is as follows. EP600A (terminated arylated polyisobutylene manufactured by Kanefuchi Chemical Co., Ltd.) (molecular weight 20,000), EP400A (terminated arylated polyisobutylene manufactured by Kanefuchi Chemical Co., Ltd. (molecular weight 10,000)), EP200A (terminated arylated polycarbonate produced by Kanefuchi Chemical Co., Ltd.) Polyisobutylene (molecular weight 5,000)), G3000 (polyisobutylene (molecular weight 2,200) by BASF Corporation), EP100S (terminal alkoxysilylated polyisobutylene by Kanefuchi Chemical Co., Ltd.), SPBDA (terminal acryloylation by Osaka Corporation) Hydrogenated polybutadiene (molecular weight 6,000)), L-1253 (fractionated end methacryloylated hydrogenated polybutadiene made by Krayton Polymer Japan Co., Ltd.), BAC-45 (terminal acryloylated unhydrogenated polybutadiene made by Osaka Yuki Co., Ltd.), UC-02 ( Terminal acryloylated hydrogenated polyisoprene made by clare Corporation, L-207 (terminal epoxidized hydrogenated polybutadiene made by Krayton Polymer Zappen Corporation), Darocure 1173 (Photoradical polymerization initiator by Nippon Chiba Co., Ltd. (2 -Hydroxy-2-methyl-1-phenyl-propane 1-one), Rhodorsil 2074 (photo cationic polymerization initiator ((trick) iodonium tetrakis (pentafluorophenyl) borate manufactured by Rhodia))).

These materials were mixed and stirred as shown in Table 4, and each sample was prepared. About each sample obtained, the evaluation test shown in the following item is done, and the result is shown in Table 5. FIG.

Compatibility Test

The compatibility was confirmed by observing the state of the liquid after leaving about 20 g of each composition based on an Example and a comparative example in a 50 mL glass bottle and leaving it to stand at 25 degreeC for 24 hours.

Photocurability Test

Photocurability was put into about 25 g of polycaps of each composition based on an Example and a comparative example, it hardened at 3,000 mJ / cm <2>, and the hardening state was visually observed.

[Hardness test]

Resin hardness superimposed two sheets of hardened | cured material used for the photocurability confirmation test, and made it the average of the measurement value of arbitrary five points by the hardness meter (tyrometa type A or C).

[State of Cured Product after Compression Permanent Distortion Test, Compression Permanent Distortion Test]

The compression permanent distortion test was performed by the following operation (JIS K6262 test). That is, each composition hardened on a disk having a diameter of 29.0 ± 0.5 mm and a thickness of 12.5 ± 0.3 mm is sandwiched between stainless steel sheets having a smooth surface, and a mild steel spanner having a thickness of 9.38 ± 0.01 mm by bolts / nacs. Compress until thick. After leaving this test piece for 72 hours in a 150 degreeC thermostat, it is quickly taken out from a compression apparatus and left for about 30 minutes at 23 +/- 5 degreeC. After the lapse of a predetermined time, the appearance observation and the thickness measurement of the cured product are performed. In addition, the compression set was calculated by the following equation.

                              Table 4

Example 17 Example 18 Example 19 Example 20 Example 21 Example 22 Example 23 EP600A 100 100 100 100 EP400A 100 EP200A 100 G3000 100 EP100S SPBDA 20 40 60 40 40 40 L-1253 40 BAC-45 UC-102 L-207 Darocure 1173 2 2 2 2 2 2 2 Rhodial 2074

Example 24 Example 25 Comparative Example 9 Comparative Example 10 Comparative Example 11 Comparative Example 12 Comparative Example 13 EP600A 100 100 100 100 100 100 EP400A EP200A G3000 EP100S 100 SPBDA 15 65 40 L-1253 BAC-45 40 UC-102 40 L-207 40 60 Darocure 1173 2 2 2 2 2 Rhodial 2074 2 2

                                     Table 5

Example 17 Example 18 Example 19 Example 20 Example 21 Example 22 Example 23 Compatibility Good Good Good Good Good Good Good Photocurable Good Good Good Good Good Good Good Hardness 10 (C) 2 (A) 12 (A) 3 (A) 4 (A) 10 (C) 5 (A) Hardened state after permanent compression distortion test  Good  Good  Good  Good  Good  Good  Good Permanent compression distortion (%) 0 0 5.0 8.3 8.3 2.0 1.5

Example 24 Example 25 Comparative Example 9 Comparative Example 10 Comparative Example 11 Comparative Example 12 Comparative Example 13 Compatibility Good Good Good detach White cloud White cloud White cloud Photocurable Gel Good Good Not hardened Not hardened Not hardened Gel Hardness Inability to measure 15 (A) 3 (A) - - - Inability to measure Hardened state after permanent compression distortion test  Bleed  collapse  collapse  -  -  -  Bleed Permanent compression distortion (%) - - - - - - 260

-Indicates no measurement

As apparent from the above results, when 20 to 60 parts by weight of a hydrogenated polybutadiene having a (meth) acryloyl group is added to 100 parts by weight of relatively high molecular weight polyisobutylene, the compatibility is good and the photocurability is also good. It was found that the compression permanent warpage test results were also good.

The photocurable composition of the present invention is susceptible to high temperatures such as liquid crystal display devices, organic EL devices, dye-sensitized solar cells, electronic papers, lithium ion batteries, poracene batteries, oxyride batteries, capacitors, fuel cells, and automotive engine parts. Used as a sealant for members and the like.

Claims (11)

(A) Hydrogenated polybutadiene which has a (meth) acryloyl group, (B) Saturated aliphatic hydrocarbon-type elastomer, and (C) Photoinitiator, The photocurable composition characterized by the above-mentioned. The general formula of component (A) according to claim 1:

(Wherein R ¹ And R ² Each independently represents a hydrogen atom or a methyl group, R ³ and R ⁴ Each independently represents a simple linking group, an oxygen atom, or a divalent organic group having 1 to 16 carbon atoms, wherein x: y = 0 to 100: 100 to 0, and n is 15 to 150. The photocurable composition according to claim 1 or 2, further comprising (D) a C5 or more chain aliphatic or alicyclic monofunctional (meth) acrylate. (B) Component is 20-80 weight part, (C) component is 0.5-5 weight part, (D) component is 0-80 with respect to any one of Claims 1-3. Photocurable composition which is below a weight part. The photocurable composition according to any one of claims 1 to 4, wherein the component (B) is at least one member selected from hydrogenated polybutadiene and polyisobutylene. The photocurable composition according to any one of claims 1 to 5, wherein component (B) has a molecular weight of 5,000 or less. The photocurable composition of Claim 1 or 2 whose component (B) is polyisobutylene of the molecular weight 500-50,000, and (A) component is 20-60 weight part with respect to 100 weight part of (B) component. The photocurable composition of Claim 7 whose compression set distortion at 150 degreeC is 20% or less in JISK6262 test of the hardened | cured material of a photocurable composition. The general formula of component (B) according to claim 7 or 8:

(R1, R2 represents an alkyl group or an alkenyl group, and m represents 8 to 800.) The photocuring composition which is polyisobutylene represented by. The photocurable composition of any one of Claims 7-9 whose molecular weight of (B) component is 2,000-50,000. A sealing method comprising applying the photocurable composition according to any one of claims 1 to 10 on a solid substrate to be bonded and sealed, and irradiating light to cure the composition.