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WO2014141819A1 - Composition de résine durcissable - Google Patents

Composition de résine durcissable Download PDF

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Publication number
WO2014141819A1
WO2014141819A1 PCT/JP2014/053648 JP2014053648W WO2014141819A1 WO 2014141819 A1 WO2014141819 A1 WO 2014141819A1 JP 2014053648 W JP2014053648 W JP 2014053648W WO 2014141819 A1 WO2014141819 A1 WO 2014141819A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
meth
polysiloxane
silicone resin
resin composition
Prior art date
Application number
PCT/JP2014/053648
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English (en)
Japanese (ja)
Inventor
つばさ 伊藤
石川　和憲
Original Assignee
横浜ゴム株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 横浜ゴム株式会社 filed Critical 横浜ゴム株式会社
Priority to CN201480009305.7A priority Critical patent/CN105164168A/zh
Priority to KR1020157022469A priority patent/KR102180721B1/ko
Priority to JP2015505338A priority patent/JP6269652B2/ja
Publication of WO2014141819A1 publication Critical patent/WO2014141819A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C09J183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking
    • C08L2312/06—Crosslinking by radiation

Definitions

  • the present invention relates to a curable resin composition that can be suitably used as an adhesive for electronic devices such as liquid crystal displays.
  • Adhesives are used in various parts of electronic devices such as liquid crystal displays.
  • Examples of such an adhesive include a photocurable resin composition containing an acrylic monomer or an acrylic oligomer.
  • Patent Document 1 discloses a photocurable resin composition containing (meth) acrylate oligomer (so-called urethane acrylate) having polyurethane as a skeleton as an adhesive for bonding a display body such as a liquid crystal display and an optical functional material. (Claim 5 etc.).
  • an object of this invention is to provide the curable resin composition which is excellent in the heat resistance of hardened
  • the inventor of the present invention uses a polysiloxane having a (meth) acryloyl group and a silicone resin represented by a specific average unit formula, whereby the heat resistance of the cured product is improved.
  • the inventors have found that an excellent curable resin composition can be obtained, and have reached the present invention. That is, the present inventors have found that the above problem can be solved by the following configuration.
  • R 1 SiO 3/2 a (R 2 2 SiO 2/2 ) b (R 3 3 SiO 1/2 ) c (SiO 4/2 ) d (X 1 O 1/2 ) e
  • R 1 , R 2 and R 3 each independently comprise an aryl group, a (meth) acryloyl group-containing group, an alkyl group, a cycloalkyl group, a vinyl group-containing group and an epoxy group-containing group.
  • X 1 represents a group selected from the group consisting of a hydrogen atom and an alkyl group
  • a, b, c, d and e are 0 ⁇ a ⁇ 1, 0 ⁇ b ⁇ 1, 0 ⁇ c ⁇ 1, 0 ⁇ d ⁇ 1, 0 ⁇ e ⁇ 1, 0 ⁇ b / a ⁇ 10, 0 ⁇ c / a ⁇ 5, 0 ⁇ d / (a + b + c + d) ⁇ 0.3, 0 ⁇ e / (a + b + c + d) ⁇ 0.4 Is satisfied.
  • the curable resin composition of the present invention (hereinafter, also simply referred to as the composition of the present invention) will be described.
  • a numerical range represented by using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • the composition of the present invention contains a polysiloxane (A) having at least one (meth) acryloyl group in one molecule and a silicone resin (B) represented by an average unit formula (1) described later. It is an adhesive resin composition.
  • the composition of the present invention is considered to exhibit excellent heat resistance when the composition has such a configuration. This is not clear in detail, but is estimated to be as follows.
  • the composition of the present invention uses a specific polysiloxane (A) and a specific silicone resin (B) in combination.
  • the silicone resin (B) used in the present invention has a branched structure. Since the composition of the present invention uses these two components in combination, the cured product is a composite of a siloxane skeleton in which a polysiloxane having a (meth) acryloyl group crosslinked and a specific silicone resin having a branched structure are entangled. And chemical durability such as radical resistance is improved. Such an improvement in chemical durability is considered to contribute to an improvement in heat resistance.
  • the present invention is characterized in that in the silicone resin (B), the aryl group ratio described later is 15 mol% or more.
  • the polysiloxane (A) used in the composition of the present invention is not particularly limited as long as it is a polysiloxane having at least one (meth) acryloyl group in one molecule.
  • the (meth) acryloyl group represents an acryloyl group or a methacryloyl group.
  • the polysiloxane refers to a compound having two or more siloxane structures (—Si—O—) in the main chain.
  • the polysiloxane (A) is crosslinked by the reaction between the (meth) acryloyl groups of the polysiloxane (A) at the time of curing.
  • the silicone resin (B) mentioned later has a (meth) acryloyl group, not only polysiloxane (A) but also silicone resin (B) are bridge
  • the polysiloxane (A) may be a linear polysiloxane or a branched polysiloxane. Among these, a linear polysiloxane (linear polysiloxane) is preferable because the elongation of the cured product is excellent.
  • the position having the (meth) acryloyl group is not particularly limited.
  • the polysiloxane (A) may have a (meth) acryloyl group at the terminal or a (meth) acryloyl group in the side chain.
  • polysiloxane (A) is a linear polysiloxane, it is preferable that it has (meth) acryloyl groups at both ends.
  • Examples of the group bonded to the silicon atom in the polysiloxane (A) include a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group, and a hydrocarbon group which may have a hetero atom.
  • a halogen atom a fluorine atom, a chlorine atom, a bromine atom, an iodine atom etc. are mentioned, for example.
  • the hetero atom of the hydrocarbon group that may have a hetero atom include an oxygen atom, a nitrogen atom, a sulfur atom, and a phosphorus atom.
  • hydrocarbon group of the hydrocarbon group that may have a hetero atom examples include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or a group in which these are combined.
  • the aliphatic hydrocarbon group may be linear, branched or cyclic.
  • Specific examples of the aliphatic hydrocarbon group include a linear or branched alkyl group (particularly, having 1 to 10 carbon atoms), a linear or branched alkenyl group (having 2 to 10 carbon atoms), and a linear chain.
  • linear or branched alkynyl groups particularly 2 to 10 carbon atoms
  • linear or branched cycloalkyl groups and the like.
  • Examples of the aromatic hydrocarbon group include an aromatic hydrocarbon group having 6 to 20 carbon atoms, and more specifically, an aryl group and a naphthyl group.
  • Examples of the aryl group include a phenyl group (hereinafter sometimes referred to as “Ph”), an aryl group having 6 to 18 carbon atoms such as a tolyl group, and a xylyl group. It is preferable.
  • the polysiloxane (A) preferably has an aryl group.
  • Specific examples and preferred embodiments of the aryl group are as described above. Among them, 5 to 50 mol% of the group bonded to the silicon atom of the polysiloxane (A) is preferably an aryl group, and more preferably 10 to 30 mol% is an aryl group.
  • the polysiloxane (A) preferably has an alkoxy group because of its excellent adhesion to the adherend.
  • the polysiloxane (A) preferably has an aryl group and an alkoxy group from the viewpoint of transparency.
  • the polysiloxane (A) preferably has a urethane bond because hydrogen bonds are formed in the cured product to improve the adhesion of the cured product.
  • polysiloxane (A) As a suitable aspect of polysiloxane (A), the compound etc. which are represented by a following formula (A1) are mentioned, for example.
  • R 21 represents a hydrogen atom or a methyl group (hereinafter sometimes referred to as “Me”). A plurality of R 21 may be the same or different.
  • R 22 represents a hydrocarbon group (preferably having 1 to 6 carbon atoms). Specific examples of the hydrocarbon group are as described above. A plurality of R 22 may be the same or different.
  • R 23 represents a hydrogen atom or a hydrocarbon group (preferably having 1 to 18 carbon atoms). Specific examples of the hydrocarbon group are as described above. A plurality of R 23 may be the same or different.
  • R 24 represents a divalent organic group.
  • divalent organic group examples include a substituted or unsubstituted aliphatic hydrocarbon group (for example, an alkylene group, preferably 1 to 8 carbon atoms), a substituted or unsubstituted aromatic hydrocarbon group (for example, an arylene group).
  • aliphatic hydrocarbon group for example, an alkylene group, preferably 1 to 8 carbon atoms
  • aromatic hydrocarbon group for example, an arylene group
  • R 25 and R 26 represents a hydrocarbon group which may have a hetero atom. Specific examples of the hydrocarbon group which may have a hetero atom are as described above. R 25 and R 26 may be the same or different.
  • l represents a positive integer. Among these, an integer of 1 to 500 is preferable, and an integer of 3 to 300 is more preferable.
  • n represents an integer of 0 to 2. Especially, since it is excellent in adhesiveness with a to-be-adhered body, it is preferable that it is an integer greater than or equal to 1.
  • the compound represented by the above formula (A1) is preferably a compound in which 5 to 50 mol% of the groups bonded to the silicon atom are aryl groups because the cured product is more excellent in heat resistance and toughness. More preferably, ⁇ 30 mol% is an aryl group.
  • the weight average molecular weight (Mw) of the polysiloxane (A) is not particularly limited, but is preferably from 100 to 1,000,000, and preferably from 500 to 50,000, because the toughness and elongation of the cured product are excellent. Is more preferable.
  • a weight average molecular weight is taken as the weight average molecular weight of polystyrene conversion measured by the gel permeation chromatography (GPC) which uses chloroform as a solvent.
  • the viscosity of the polysiloxane (A) at 25 ° C. is preferably 20 to 1,000,000 mPa ⁇ s, more preferably 200 to 100,000 mPa ⁇ s. In the present application, the viscosity is measured at 25 ° C. according to JIS K7117-1 4.1 (Brookfield rotary viscometer).
  • the content of the polysiloxane (A) is not particularly limited, but is preferably 10 to 90% by mass, and preferably 30 to 70% by mass because of excellent toughness and elongation of the cured product. It is more preferable.
  • the method for synthesizing the polysiloxane (A) is not particularly limited.
  • the polysiloxane (a1) and the monomer (a2) having a (meth) acryloyl group are reacted to form at least one (meth) acryloyl in one molecule.
  • a method for obtaining a polysiloxane having a group a method of reacting a polysiloxane (a11) having a silanol group at the terminal (preferably both terminals) and an alkoxysilane (a21) having a (meth) acryloyl group is preferable.
  • the alkoxysilane (a21) having a (meth) acryloyl group preferably has two or more alkoxy groups from the viewpoint of excellent adhesion to the adherend.
  • the method of synthesizing the polysiloxane (A) by reacting the polysiloxane (a1) and the monomer (a2) having a (meth) acryloyl group for example, at the terminals (preferably both terminals)
  • Examples thereof include a method of reacting a polysiloxane (a12) having a hydroxyalkyl group (—R—OH: R is an alkylene group) with an isocyanate (a22) having a (meth) acryloyl group.
  • Another preferred embodiment of the method for synthesizing the polysiloxane (A) by reacting the polysiloxane (a1) with the monomer (a2) having a (meth) acryloyl group includes a polysiloxane having an epoxy group (a13). ) And (meth) acrylic acid.
  • the polysiloxane (a1) used for the synthesis of the polysiloxane (A) is preferably one having an aryl group because the cured product has excellent transparency and the cured product has more excellent heat resistance. . Specific examples and preferred embodiments of the aryl group are as described above.
  • the silicone resin (B) used in the composition of the present invention is a silicone resin represented by the following average unit formula (1).
  • the following average unit formula (1) represents the number of moles of each siloxane unit when the total number of siloxane units constituting the silicone resin (B) is 1 mole.
  • R 1 , R 2 and R 3 are each independently an aryl group, a (meth) acryloyl group-containing group, an alkyl group (preferably having 1 to 10 carbon atoms), a cycloalkyl group or a vinyl group.
  • a plurality of R 2 and R 3 may be the same or different.
  • one unit (R 1 SiO 3/2 ) and another unit (R 1 SiO 3/2 ) are the same. Or different.
  • R 1 of a certain unit (R 1 SiO 3/2) of R 1 and other units (R 1 SiO 3/2) may be different even in the same.
  • the (meth) acryloyl group-containing group is not particularly limited as long as it is a group containing a (meth) acryloyl group, but is a hydrocarbon group having a (meth) acryloyloxy group as a substituent from the viewpoint of curability. And an alkyl group (particularly having 1 to 10 carbon atoms) having a (meth) acryloyloxy group as a substituent is more preferable.
  • R 11 represents a hydrogen atom or a methyl group.
  • R 12 represents a divalent organic group. Specific examples and preferred embodiments of the divalent organic group are the same as R 24 in formula (A1) described above.
  • * represents a bonding position.
  • the vinyl group-containing group is not particularly limited as long as it is a group containing a vinyl group (CH 2 ⁇ CH—) (hereinafter sometimes referred to as “Vi”).
  • a vinyl group containing group a vinyl group, an allyl group, etc. are mentioned, for example, It is preferable that it is a vinyl group especially.
  • the ratio of aryl groups (in the total organic groups) to the total organic groups represented by R 1 , R 2 and R 3 (hereinafter also referred to as aryl group ratio) is 15 mol% or more. Especially, it is preferable that it is 25 mol% or more from the reason which the adhesiveness and transparency of hardened
  • the upper limit is not particularly limited, but is usually 80 mol% or less, and preferably 70 mol% or less.
  • X 1 represents a group selected from the group consisting of a hydrogen atom and an alkyl group (preferably having 1 to 10 carbon atoms).
  • the alkyl group may be linear, branched or cyclic.
  • a, b, c, d and e are 0 ⁇ a ⁇ 1, 0 ⁇ b ⁇ 1, 0 ⁇ c ⁇ 1, 0 ⁇ d ⁇ 1, 0 ⁇ e ⁇ 1, 0 ⁇ b / a ⁇ 10, 0 ⁇ c / a ⁇ 5, 0 ⁇ d / (a + b + c + d) ⁇ 0.3, 0 ⁇ e / (a + b + c + d) ⁇ 0.4 Is satisfied.
  • b / a is preferably 0 to 1.0.
  • c / a is preferably 0 to 1.0, and more preferably 0.5 to 0.7.
  • d / (a + b + c + d) is preferably 0 to 1.0.
  • e / (a + b + c + d) is preferably 0 to 1.0.
  • a is a positive number (> 0). That is, the silicone resin (B) has a branched structure represented by (R 1 SiO 3/2 ).
  • the silicone resin (B) preferably has the (meth) acryloyl group-containing group described above for the reason of excellent adhesion of the cured product.
  • the weight average molecular weight (Mw) of the silicone resin (B) is not particularly limited, but is preferably 1,000 to 300,000, and preferably 1,500 to 100,000 from the viewpoint of toughness and rigidity of the cured product. It is more preferable.
  • the method for synthesizing the silicone resin (B) is not particularly limited, and examples thereof include a method of dealcoholizing a trialkoxysilane having an aryl group.
  • Preferred embodiments of the method for synthesizing the silicone resin (B) include trialkoxysilane (b1) having an aryl group, trialkoxysilane (b2) having a (meth) acryloyl group-containing group, and a polymerizable group (preferably vinyl).
  • the definition and preferred embodiments of the (meth) acryloyl group-containing group are as described above.
  • composition of the present invention preferably further contains a monofunctional (meth) acrylic monomer (C) for the reason that the cured product is excellent in flexibility.
  • a (meth) acryl monomer represents an acrylic monomer or a methacryl monomer.
  • the monofunctional (meth) acrylic monomer (C) is not particularly limited, but ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, tridecyl (meth) acrylate , Hexadecyl (meth) acrylate, octadecyl (meth) acrylate, isoamyl (meth) acrylate, isodecyl (meth) acrylate, isostearyl (meth) acrylate, ethoxyethoxyethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 3 -Aliphatic (meth) acrylates such as chloro-2-hydroxypropyl (meth) acrylate, methoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate, benzy
  • the monofunctional (meth) acrylic monomer (C) does not include a monofunctional (meth) acrylic monomer having a plurality of ester groups.
  • the content of the monofunctional (meth) acrylic monomer (C) is not particularly limited, but is 10 to 30% by mass with respect to the total amount of the composition from the viewpoint of toughness and flexibility of the cured product. It is preferable.
  • the ester group-containing (meth) acrylate monomer (D) is not particularly limited, but is a compound represented by the following formula (D1) from the viewpoint of toughness and flexibility of the cured product and adhesion to the adherend. It is preferable that
  • R 11 represents a hydrogen atom or a methyl group.
  • R 12 represents a single bond or a divalent organic group. Specific examples and preferred embodiments of the divalent organic group are the same as R 24 in formula (A1) described above.
  • n represents an integer of 1 to 25.
  • the content of the ester group-containing (meth) acrylate monomer (D) is not particularly limited, but from the viewpoint of toughness and flexibility of the cured product and adhesion to the adherend, The content is preferably 5 to 30% by mass with respect to the total amount.
  • the composition of the present invention may further contain a photopolymerization initiator.
  • the photopolymerization initiator is not particularly limited, and examples thereof include acetophenones, benzoins, benzophenones (such as 1-hydroxy-1,2,3,4,5,6-hexahydrobenzophenone), phosphine oxides, ketals.
  • Anthraquinones thioxanthones, azo compounds, peroxides, 2,3-dialkyldione compounds, disulfide compounds, fluoroamine compounds, aromatic sulfoniums, lophine dimers, onium salts, borate salts, activity Examples include esters, active halogens, inorganic complexes, and coumarins.
  • the content of the photoinitiator polymerization initiator is not particularly limited, but is preferably 1 to 5% by mass from the viewpoint of curability and storage stability.
  • the composition of the present invention may further contain an additive within a range not impairing its effects and purposes.
  • additives include inorganic fillers, antioxidants, lubricants, ultraviolet absorbers, thermal light stabilizers, dispersants, antistatic agents, polymerization inhibitors, antifoaming agents, curing accelerators, solvents, inorganic phosphors, Anti-aging agent, radical inhibitor, adhesion improver, flame retardant, surfactant, storage stability improver, ozone anti-aging agent, thickener, plasticizer, radiation blocker, nucleating agent, coupling agent, conductive
  • properties-imparting agents phosphorus peroxide decomposers, pigments, metal deactivators, and physical property modifiers.
  • Various additives are not particularly limited. For example, a conventionally well-known thing is mentioned.
  • the method for producing the composition of the present invention is not particularly limited, and examples thereof include a method for producing the composition by mixing the above-described essential components and optional components.
  • composition of the present invention can be suitably used for adhesives, primers, sealing materials and the like for electronic devices such as liquid crystal displays, recording media, optical devices, and semiconductor integrated circuits.
  • polysiloxane A2 has the following structure, has an aryl group (phenyl group) and a urethane bond, and further has an acryloyl group at both ends. In addition, polysiloxane A2 does not have an alkoxy group.
  • silicone resin B1 silicone resin B1.
  • the average unit formula was as follows.
  • Silicone resin B1 has an acryloyl group.
  • the aryl group ratio of the silicone resin B1 is 30 mol%.
  • silicone resin B2 A silicone resin was obtained according to the same procedure as the synthesis of silicone resin B1, except that the amount of KBM103 was 94.5 g and the amount of KBM5103 was 76 g. Let the obtained silicone resin be silicone resin B2.
  • the average unit formula was as follows. (PhSiO 3/2 ) 0.32 (AcSiO 3/2 ) 0.22 (ViMe 2 SiO 1/2 ) 0.46
  • Ac represents —C 3 H 6 OC ( ⁇ O) CH ⁇ CH 2 .
  • Silicone resin B2 has an acryloyl group. The aryl group ratio of the silicone resin B2 is 17 mol%.
  • silicone resin B3 A silicone resin was obtained according to the same procedure as the synthesis of silicone resin B1, except that KBM5103 was not added. Let the obtained silicone resin be silicone resin B3. When NMR analysis was performed on the silicone resin B3, the average unit formula was as follows. (PhSiO 3/2 ) 0.58 (ViMe 2 SiO 1/2 ) 0.42 Silicone resin B3 does not have a (meth) acryloyl group. The aryl group ratio of the silicone resin B3 is 32 mol%.
  • ⁇ Adhesive strength> The obtained curable resin composition was applied to a glass plate (application area: ⁇ 5 mm, application thickness: 0.3 mm), and another glass plate was bonded to the applied part in a cross shape. Thereafter, light irradiation (integrated light amount: 3,000 mJ / cm 2 ) was performed using a light irradiation device (device name: GS UVSYSTEM TYPE S250-01, light source: metal hydrolamp, manufactured by GS Yuasa Lighting Co., Ltd.) and cured. . In this way, a sample for evaluating the adhesive strength was prepared. The adhesive strength was evaluated by the tensile test about the produced sample.
  • the adhesive strength maintenance rate is preferably 80% or more.
  • Examples 1 to 5, 7 and 9 in which the silicone resin (B) has a (meth) acryloyl group had higher adhesive strength before the high-temperature and high-humidity environment test and excellent adhesion. From the comparison between Examples 1 and 2, an example in which the silicone resin (B) has an aryl group ratio of 25 mol% or more as compared with Example 2 in which the silicone resin (B) has an aryl group ratio of less than 25 mol%. No. 1 (both before and after the high temperature and high humidity environment test) had higher adhesive strength and excellent adhesion. Moreover, the transmittance was high and the transparency was excellent.
  • the polysiloxane (A) is urethane compared to Examples 6 and 10 where the polysiloxane (A) does not have a urethane bond.
  • Examples 5 and 9 having a bond had higher adhesive strength (before and after the high-temperature and high-humidity environment test) and were excellent in adhesion.
  • Examples 1 to 4 and 8 in which the polysiloxane (A) has an aryl group and an alkoxy group have high transmittance and excellent transparency.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

L'invention a pour objet une composition de résine durcissable ayant une excellente résistance à la chaleur du produit durci. Cette composition de résine durcissable contient un polysiloxane (A) ayant au moins un groupe (méth)acryloyle dans la molécule et une résine de silicone (B) représentée par une formule unitaire moyenne particulière.
PCT/JP2014/053648 2013-03-15 2014-02-17 Composition de résine durcissable WO2014141819A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201480009305.7A CN105164168A (zh) 2013-03-15 2014-02-17 固化性树脂组合物
KR1020157022469A KR102180721B1 (ko) 2013-03-15 2014-02-17 경화성 수지 조성물
JP2015505338A JP6269652B2 (ja) 2013-03-15 2014-02-17 硬化性樹脂組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2013-053475 2013-03-15
JP2013053475 2013-03-15

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WO2014141819A1 true WO2014141819A1 (fr) 2014-09-18

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PCT/JP2014/053648 WO2014141819A1 (fr) 2013-03-15 2014-02-17 Composition de résine durcissable

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JP (1) JP6269652B2 (fr)
KR (1) KR102180721B1 (fr)
CN (1) CN105164168A (fr)
TW (1) TWI613271B (fr)
WO (1) WO2014141819A1 (fr)

Cited By (1)

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JP2023521261A (ja) * 2021-03-16 2023-05-24 モメンティブ・パフォーマンス・マテリアルズ・コリア・カンパニー・リミテッド シリコーン系組成物及びその硬化物

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JP6481647B2 (ja) * 2016-03-22 2019-03-13 信越化学工業株式会社 紫外線硬化性シリコーン組成物、その硬化物、及び該組成物からなる光学素子封止材、並びに該光学素子封止材により封止された光学素子
US20190233670A1 (en) * 2016-06-30 2019-08-01 Shin-Etsu Chemical Co., Ltd. Ultraviolet curable silicone composition and cured product of same
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