WO2009028271A1 - Composition photodurcissable et thermodurcissable, produit durci obtenu à partir de celle-ci et procédé de durcissement - Google Patents

Composition photodurcissable et thermodurcissable, produit durci obtenu à partir de celle-ci et procédé de durcissement Download PDF

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Publication number
WO2009028271A1
WO2009028271A1 PCT/JP2008/062780 JP2008062780W WO2009028271A1 WO 2009028271 A1 WO2009028271 A1 WO 2009028271A1 JP 2008062780 W JP2008062780 W JP 2008062780W WO 2009028271 A1 WO2009028271 A1 WO 2009028271A1
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component
parts
weight
molecule
compound
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PCT/JP2008/062780
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English (en)
Japanese (ja)
Inventor
Toshihiko Anraku
Manabu Inoue
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Three Bond Co., Ltd.
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Publication of WO2009028271A1 publication Critical patent/WO2009028271A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
    • C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
    • C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
    • C08G59/1461—Unsaturated monoacids
    • C08G59/1466—Acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4064—Curing agents not provided for by the groups C08G59/42 - C08G59/66 sulfur containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

  • the present invention relates to a composition that is cured by light and heating. More specifically, the present invention relates to a light and thermosetting composition that can be temporarily fixed by light irradiation and that can be completely cured by heating. .
  • heat-curable one-component epoxy resin compositions are known to be able to set the heating temperature and heating time according to the application as desired.
  • the heating process itself is advantageous in that it is cured at a lower temperature than at a higher temperature because energy is saved and the adherence of the adherend is not wasted.
  • a shorter curing time is advantageous because it increases production efficiency.
  • the heating temperature is set low or the heating time is set short, the storage stability of the one-part epoxy resin composition will deteriorate and gel or thicken during storage, resulting in low-temperature rapid curing. There were limits. Therefore, in order to achieve quick curing at a relatively low temperature, an epoxy resin added with a polythiol compound is described in Japanese Patent Application Laid-Open No. 06-2 1 1 969.
  • the epoxy resin composition to which such a polythiol compound has been added must be fixed with a jig or a device in order to maintain the bonding posture while bonding even though it can be rapidly cured. Furthermore, the epoxy resin composition has a problem that the viscosity of the epoxy resin composition decreases due to the temperature rise of the composition during heating, and sagging occurs immediately before curing, or it flows out of the desired part.
  • an acrylate-based composition composed mainly of a compound having a (meth) acryloyl group can generally be made into a photocurable resin by adding a photopolymerization initiator. It is also easy to add heat curing properties by adding radical initiators such as organic peroxides. However, organic peroxides are unstable to heat, and it has been difficult to achieve both low temperature curability and storage stability in these acrylate-based compositions. Furthermore, a compound containing at least one glycidyl group in the molecule and a compound containing at least one (meth) acryloyl group in the molecule are mixed, and the compound containing glycidyl group is used as a thermosetting component.
  • compositions that function as a light- and heat-curable resin using a group-containing compound as a photocurable component are also known. Further, a compound having a glycidyl group and a (meth) acryloyl group in one molecule to which a radical photoinitiator and an epoxy thermosetting agent are added to form a light and heat curable sealant is disclosed in It is described in 1 6 0 8 7 2 publication.
  • An object of the present invention is to provide a curable composition, a cured product, and a curing method which have solved the above-described problems of the prior art.
  • the present invention provides, firstly, (1) a curable component composed of a compound having a glycidyl group and a (meth) atallyloyl group in one molecule, (2) component (1) 1 to 100 parts by weight A light and heat curable composition comprising 60 parts by weight of a polythiol compound having two or more thiol groups in one molecule and (3) an epoxy curing accelerator.
  • the present invention is a cured product obtained by curing the above composition.
  • the present invention is a curing method characterized by applying the composition described above to an object to be treated, applying the composition, irradiating it with light, and heat-treating it at the next stage.
  • the composition of the present invention can be cured by light irradiation and heating, and can be temporarily fixed by light and completely cured by heating. Therefore, a jig or the like is not required during the heating process, and heating is performed. There is no viscosity reduction of the composition during the process. Furthermore, the composition of the present invention generates a low amount of gas and can be used in applications where the gas becomes a problem.
  • the curable component of component (1) used in the present invention is composed of a monomeric or polymeric compound having at least one glycidyl group and at least one (meth) acryloyl group in one molecule (hereinafter, It may be called “epoxy acrylate compound”).
  • This epoxy acrylate compound is a compound that has two or more glycidyl groups in one molecule (hereinafter sometimes referred to as “polyfunctional epoxy resin”). It corresponds to a compound obtained by esterification with a carboxylic acid having a group (a typical example is (meth) acrylic acid).
  • (meth) acryloyl group” is a generic term for acryloyl group and methacryloyl group
  • (meth) acrylic acid” is a generic term for acrylic acid and methacrylic acid.
  • the polyfunctional epoxy resin that is a precursor of the above partial esterification reaction is an epoxy resin having at least 2 and preferably (on average) 2 to 4 epoxy groups in one molecule.
  • aliphatic polyfunctional liquid epoxy resins such as 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, or trimethylolpropane tridaricidyl ether, bisphenol A diglycidyl ether ⁇ / Bisphenolate epoxy resin such as bisphenol ⁇ / F diglycidinoreate, phenol novolac epoxy resin such as condensate of formaldehyde and phenol, cresol novolac epoxide such as condensate of formaldehyde and cresol Resin, bisphenol type novolak epoxy resin such as bisphenol type novolak epoxy resin, novolak type epoxy resin containing alicyclic skeleton such as novolak type epoxy resin of dicyclopentagen and benzene derivative having
  • Examples thereof include naphthalene skeleton-containing novolak epoxy resins such as a poxy resin and a novolak epoxy resin of naphthalene and a benzene derivative having a phenolic hydroxyl group.
  • a bisphenol epoxy resin is preferable.
  • the compound used for partial esterification of these polyfunctional epoxy resins is a carboxylic acid having a (meth) acryloyl group as described above, but acrylic acid or methacrylic acid, that is, (meth) acrylic acid is preferred. .
  • the epoxy acrylate compound as an essential component constituting the curable component of the component (1) of the present invention is typically a compound having one epoxy group and one (meth) attalyloyl group.
  • This compound is obtained by reacting the compound having two glycidyl groups and (meth) acrylic acid in a stoichiometry (0.5 equivalent of carboxyl group to 1 equivalent of glycidyl group) in the partial esterification reaction described above.
  • a compound in which two glycidyl groups are co-esterified is also mixed, and these mixed products constitute the curable component of the component (1) of the present invention. .
  • Epoxy resins are preferably used. As long as the epoxy acrylate compound is liquid, the molecular weight is not particularly limited.
  • the partial esterification reaction can be performed according to a conventional method. Typically, both components can be reacted easily and quantitatively by heating and mixing in the presence of a basic catalyst. Epoxy acrylate compounds can also be obtained as industrial materials. Examples of such products include “UVACURE 1 5 6 1” manufactured by Daicel Cytec Co., Ltd.
  • Component (2) used in the present invention is a polythiol having 2 or more, preferably 2 to 4, thiol groups in one molecule.
  • Component (2) is a component having both a function as a curing agent for heat curing of a glycidyl group and a function as a curing agent for a (meth) acryloyl group.
  • the (meth) atalyloyl group it can be cured by irradiation with light such as ultraviolet rays or by heating.
  • the amount of component (2) relative to component (1) 100 parts by weight is 1 to 60 parts by weight, preferably 5 to 40 parts by weight.
  • a curing agent / curing accelerator usually used for epoxy resins can be used.
  • a latent curing agent it is preferable to use a latent curing agent. Any latent curing accelerator can be used without particular limitation as long as it exhibits an activity that promotes the reaction between epoxy groups or between epoxy groups and mercapto groups at the reaction temperature.
  • 2-methylimidazole Alkyl imidazole compounds such as 2-ethylimidazole and 2-propylimidazole, arylimidazole compounds such as phenylimidazole and naphthylimidazole, and amino such as 2-aminoethylimidazole and 2-aminopropylimidazole Alkylimidazole compounds, adipic acid dihydrazide, eicosane diacid dihydrazide, 7, 11 1-octadecadiene 1, 1,8-dicarbohydrazide, 1,3 bis (hydrazino carboethyl) 5-isopropylhydantoin, etc.
  • latent curing accelerators are high in polyurethane, polyester, etc. It was coated with an inorganic material, a metal thin film such as Ni or Cu, and an inorganic material such as calcium silicate, or was made into an adduct by reacting with an equivalent amount of epoxy resin. May be. These uses are preferable from the viewpoint of extending the pot life. With these latent curing accelerators, the activity of the polythiol compound of component (2) is increased catalytically, fast curability is obtained, and the necessary adhesive strength is obtained even if the heating temperature during curing is lowered. be able to.
  • the amount of the latent curing accelerator used as the component (C) is preferably from 0.001 to 50 parts by weight based on 100 parts by weight of the component (1). If this amount is less than 0.01 parts by weight, the effect of promoting hardening tends to be insufficient, and if it exceeds 50 parts by weight, the compatibility tends to decrease.
  • a radical photoinitiator may be added as a component (4) to the composition of the present invention.
  • component (4) when component (4) is added in a large amount, it causes the outgas to be released from the cured product.
  • the component (4) since it is used in combination with the component (3), the component (4) can be greatly improved in photocurability by adding a small amount.
  • radical photoinitiator of component (4) include 1-hydroxycyclohexyl ⁇ / phenenoleketone, 2-hydroxy-2-methynolee 1 monophenyl / repropane 1-1, diethoxyacetophenone, 1 1 (4-Isopropylphenyl) 1 2 -Hydroxy 1 2 -Methylpropane 1 1-one, 1- (4 -Dodecylphenyl) 1 2 -Hydroxy 1 -Methylolepropane _ 1 _On, 4 — (2-Hydroxyethoxy) monophenyl (2-Hydroxy-1-2-propyl) Ketone, 2-Methyl-1- 1- [4- (Metinorethio) Feninore]
  • 2-Mono-Relinopronone 1, benzoin, benzoin methylenole etherol, benzoin ethylenoateol, benzoin iso
  • the amount of the photoinitiator is preferably from 0.01 to 5 parts by weight, particularly preferably from 0.1 to 2 parts by weight, per 100 parts by weight of the component (1). If it exceeds 2 parts by weight, the amount of gas generated will increase, but if it is a point where it is acceptable to generate gas, it may be used in excess of 2 parts by weight. However, addition of more than 5 parts by weight is not preferred because it tends to impair storage stability.
  • an appropriate amount of acidic substance or radical trapping agent may be added.
  • acidic substances include, but are not limited to, phosphoric acid, boric acid, acrylic acid, malic acid, and the like.
  • radical trapping agents include, but are not limited to, dibutylhydroxytoluene, 4-methoxyphenol, 2,6-di-tert-butyl-p-cresol, hydroquinone, and 1,7-dihydroxynaphthalene. It is not something.
  • the curable composition of the present invention may contain various additives such as a filler, a diluent, a solvent, a coupling agent, a colorant, a thixotropic agent, and an antifoaming agent as necessary.
  • the curable composition of the present invention can be used for a wide range of applications such as adhesives, sealing agents, castings, etc., as in the case of conventionally known one-component epoxy resin compositions. There are appropriate ones for each application.
  • One specific example is a liquid crystal display panel, and the curable composition of the present invention is suitably used as a sealing agent for bonding substrates together.
  • Component (1) The following commercially available products and the products produced in Production Examples 1 and 2 were used. (Commercially available product) Daicel Cytec Co., Ltd.'s "UVACURE 1 56 1" is a compound containing one glycidyl group and one acryloyl group in one molecule, which is a partial esterification of bisphenol A type epoxy resin with acrylic acid. used.
  • j ER828 bisphenol A type epoxy resin manufactured by Japan Epoxy Resin Co., Ltd., which is an epoxy resin having two glycidyl groups in one molecule, was used.
  • Component (2) QX 30 which is a trifunctional thiol compound manufactured by Japan Epoxy Resin Co., Ltd., QX 40 which is a tetrafunctional thiol compound, and QX 60 which is a hexafunctional thiol compound were used as thiol compounds.
  • Ingredient (3) “Amicure PN23” manufactured by Ajinomoto Fine Techno as a solid (powder) latent curing agent at room temperature, and “1 B 2MZ” (Imidazol) manufactured by Shikoku Kasei Co., Ltd. as a liquid curing agent used.
  • dibutylhydroxytoluene (BHT) was used as the radical trapping agent, and “L-1 07N” (cyclic boric acid compound) manufactured by Shikoku Kasei Co., Ltd. was used as the acidic substance.
  • DCP-A dicyclopentadienyl acrylate
  • IBX-A isobornyl acrylate
  • Photocurability 5 g of each composition was dropped into a transparent container made of polyethylene with a diameter of 3 cm and a depth of 1 cm, and irradiated with 3000 m jZcm 2 of ultraviolet light with a high-pressure mercury lamp. The surface condition after irradiation was observed by finger touch. (Completely cured: ⁇ , cured but somewhat tacky: ⁇ , cured to non-fluidity: ⁇ , uncured: X)
  • Heat-curing property 1 Place an aluminum plate on a hot plate set at 20 ° C, hang about 1 Omg of the sample on an aluminum foil plate, and measure the time to gelation. (Unit: seconds)
  • Examples 1 to 5 were blends of the present invention, and the desired compositions could be obtained in all of the items of low temperature curability, UV curability, 120 ° C. gel time, and shelf life preservability.
  • Comparative Example 1 the power given by using j ER 828 instead of UVACURE 1 56 1; there is no UV curability.
  • Comparative Example 2 j ER 828 and DC P—A were mixed at 1: 1 (parts by weight), but the low temperature curability was poor, and the 120 ° C gel time was significantly delayed.
  • Comparative Example 3 the amount of thiol is added in an amount exceeding the regulation of the present invention.
  • Comparative Example 4 showed a system in which no thiol was added, but the 120 ° C. gel time was delayed.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epoxy Resins (AREA)

Abstract

La présente invention concerne une composition photodurcissable et thermodurcissable contenant (1) un composant durcissable constitué d'un composé comportant un groupe glycidyle et un groupe (méth)acryloyle dans une molécule, (2) un composé de polythiol comportant au moins deux groupes thiols dans une molécule et qui est présent à hauteur de 1 à 60 parties en poids par rapport au composant (3) et, (3) un accélérateur de durcissement à base d'époxy. Comme cette composition n'a pas besoin de gabarit et qu'elle ne subit pas de baisse de sa viscosité au cours du durcissement, elle se révèle remarquable tant en termes d'aptitude au façonnage que de qualité du produit durci.
PCT/JP2008/062780 2007-08-28 2008-07-09 Composition photodurcissable et thermodurcissable, produit durci obtenu à partir de celle-ci et procédé de durcissement WO2009028271A1 (fr)

Applications Claiming Priority (2)

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JP2007220583A JP2009051954A (ja) 2007-08-28 2007-08-28 光および加熱硬化性組成物とその硬化物
JP2007-220583 2007-08-28

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WO2015098875A1 (fr) * 2013-12-24 2015-07-02 株式会社ブリヂストン Feuille adhésive, son procédé de fabrication et stratifié
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WO2015098875A1 (fr) * 2013-12-24 2015-07-02 株式会社ブリヂストン Feuille adhésive, son procédé de fabrication et stratifié
JPWO2015098875A1 (ja) * 2013-12-24 2017-03-23 株式会社ブリヂストン 接着シート、その製造方法及び積層体
EP4098680A1 (fr) * 2021-06-04 2022-12-07 Henkel AG & Co. KGaA Composition de vulcanisation double à base composés fonctionnels d'acrylate
WO2022253878A1 (fr) * 2021-06-04 2022-12-08 Henkel Ag & Co. Kgaa Composition à double durcissement à base de composés à fonctionnalité acrylate
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