WO2023079966A1 - 架橋性樹脂組成物、及び、硬化物 - Google Patents
架橋性樹脂組成物、及び、硬化物 Download PDFInfo
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- WO2023079966A1 WO2023079966A1 PCT/JP2022/039037 JP2022039037W WO2023079966A1 WO 2023079966 A1 WO2023079966 A1 WO 2023079966A1 JP 2022039037 W JP2022039037 W JP 2022039037W WO 2023079966 A1 WO2023079966 A1 WO 2023079966A1
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- acrylate
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
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- 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 crosslinkable resin composition and a cured product obtained by curing the crosslinkable resin composition.
- Cured products obtained from epoxy resins are excellent in heat resistance, mechanical strength, electrical properties, adhesiveness, etc., and are indispensable materials in various fields such as electricity / electronics, paints, and adhesives.
- thermosetting resins such as epoxy resins
- thermosetting resins such as epoxy resins cannot be dissolved in solvents (insoluble) and do not dissolve even at high temperatures (infusible). Since the cured product after use is waste, it is a challenge to reduce waste and reduce the burden on the environment.
- Patent Document 1 For cracks that occur in general resin cured products, for example, in Patent Document 1, a method that enables self-healing by using a fiber-reinforced plastic in which a plurality of capsules containing unsolidified adhesive is embedded. is disclosed.
- Patent Document 2 even if a crack or peeling occurs in a sealing material using an epoxy resin or the like, a micrometer containing a first thermosetting resin and a second thermosetting resin precursor is disclosed. A self-healing encapsulant is disclosed using encapsulated particles.
- the problem to be solved by the present invention is to have mechanical strength, and to express flexibility, repairability, and re-moldability in a low temperature range including room temperature, and eventually, to extend the life of the cured product itself and waste. It is an object of the present invention to provide a crosslinkable resin composition that can contribute to the reduction of
- the present inventors have made extensive studies and found that a cured product having a phase separation structure formed of a continuous phase and a discontinuous phase with different tensile elastic moduli can be formed.
- the inventors have found that by using a resin composition, the resulting cured product can exhibit mechanical strength, flexibility in a low temperature range including room temperature, repairability, and remoldability, and have completed the present invention.
- the present invention has the following aspects.
- a crosslinkable resin composition capable of forming a cured product having a phase separation structure formed from a continuous phase and a discontinuous phase, The discontinuous phase has a higher tensile modulus than the continuous phase, A crosslinkable resin composition containing a reversible bond in the continuous phase.
- the continuous phase contains a reaction product of the resin component A containing the reversible bond and a curing agent; wherein the discontinuous phase comprises a reaction product of resin component B and a curing agent;
- the continuous phase comprises a reaction product of the resin component A containing the reversible bond and a curing agent and/or a self-polymerization product of the resin component A containing the reversible bond;
- the discontinuous phase comprises a reaction product of resin component B and a curing agent and/or a self-polymerization product of resin component B;
- the functional group (a1) in the continuous phase is reactive with the functional group (b1) in the discontinuous phase,
- the crosslinkable resin composition according to the above [1] or [2], wherein the phase separation structure contains a reaction product of the functional group (a1) in the continuous phase and the functional group (b1) in the discontinuous phase.
- a crosslinkable resin composition wherein the crosslinkable resin composition according to any one of [1] to [5] is a composition for a repairing/remolding material.
- the crosslinkable resin composition of the present invention can form a cured product having a phase separation structure formed from a continuous phase and a discontinuous phase, and the discontinuous phase has a higher tensile modulus than the continuous phase. is high, and by containing reversible bonds in the continuous phase, the mechanical strength of the entire cured product can be expressed by the discontinuous phase with a high elastic modulus, while it is contained in the continuous phase with a low elastic modulus (introduced) Due to the reversible bonding, molecular mobility is good even at low temperatures including room temperature, flexibility is imparted, and even if cracks occur in the cured product, repairability and re-moldability can be exhibited. , It is useful because it can contribute to the extension of the life of the cured product itself and the reduction of waste.
- FIG. 1 is an SEM photograph of a cured product obtained in Example 1.
- FIG. 1 is a GPC chart of epoxy resin (Ep-1) obtained in Synthesis Example 2.
- FIG. 1 is a 1 H-NMR spectrum of the epoxy resin (Ep-1) obtained in Synthesis Example 2.
- FIG. 1 is a GPC chart of epoxy resin (Ep-1) obtained in Synthesis Example 2.
- the present invention is a crosslinkable resin composition capable of forming a cured product having a phase separation structure formed from a continuous phase and a discontinuous phase, The discontinuous phase has a higher tensile modulus than the continuous phase, The present invention relates to a crosslinkable resin composition containing reversible bonds in the continuous phase.
- the cured product obtained using the crosslinkable resin composition of the present invention has a phase separation structure formed of a continuous phase (sea portion) and a discontinuous phase (island portion), and the continuous phase (sea portion) is , the tensile modulus is lower than that of the discontinuous phase (island portion), and as the curing of the crosslinkable resin composition progresses, the cured product forms a phase-separated structure.
- the crosslinkable resin composition can form a cured product having a phase separation structure formed from a continuous phase and a discontinuous phase.
- the mechanical strength of the entire cured product is improved, while the continuous phase containing (introduced) reversible bonds has high molecular mobility, excellent flexibility, and can be used in a low temperature range including room temperature (23 ° C.) (e.g. , 0 to 100°C), these properties can be exhibited by reversible bonding, and repairability and re-moldability can be exhibited against damage such as cracks in the cured product, and the cured product itself has a long life. It is useful because it can contribute to the reduction of waste due to curing and the reduction of waste due to cured products.
- the continuous phase contains a reaction product of the resin component A containing the reversible bond and a curing agent, wherein the discontinuous phase comprises a reaction product of resin component B and a curing agent; It is preferable that the phase-separated structure includes a reaction product of the continuous phase, the discontinuous phase, and the curing agent.
- the reaction product (reaction product A) is obtained by the reaction of the resin component A with the curing agent, and the reaction product forms a structure that serves as the base of the continuous phase (island portion).
- reaction product B is obtained by the reaction of the resin component B and the curing agent, forming a structure that forms the basis of the discontinuous phase (sea portion), and both reaction products further
- a phase-separated structure can be formed by reacting with the curing agent (sea-island interface reaction). Since the resin component A and the resin component B are structurally different (difference in functional group concentration, etc.), the reactivity with the curing agent is different, and either the resin component A or the resin component B With respect to one resin component, the reactivity with the curing agent is high, the reaction proceeds easily, and the obtained cured product can form a phase separation structure.
- the continuous phase is a reaction product of the resin component A containing the reversible bond and a curing agent, and/or self-polymerization of the resin component A containing the reversible bond.
- the discontinuous phase comprises a reaction product of resin component B and a curing agent and/or a self-polymerization product of resin component B;
- the functional group (a1) in the continuous phase is reactive with the functional group (b1) in the discontinuous phase,
- the phase-separated structure includes a reaction product between the functional group (a1) in the continuous phase and the functional group (b1) in the discontinuous phase.
- the resin component A reacts with the curing agent to obtain a reaction product (reaction product A), or the resin component A alone (a curing accelerator or the like may be used) self- A self-polymerization product is obtained by polymerization, and the reaction product or the self-polymerization product forms a structure that serves as a base for a continuous phase (island portion),
- a reaction product (reaction product B) is obtained by the reaction of the resin component B with the curing agent, or self-polymerization with the resin component B alone (in some cases, a curing accelerator is used).
- a polymerization product is obtained, the reaction product or self-polymerization product forming a structure that is the basis of the discontinuous phase (sea);
- the functional group (a1) in the continuous phase is reactive with the functional group (b1) in the discontinuous phase, and the functional group (a1) in the continuous phase and the functional group in the discontinuous phase ( By reacting with b1), the resulting cured product can form a phase-separated structure (sea-island structure).
- the resin component A and the resin component B can be prepared into various phase-separated structures by combining their respective reactive functional groups, and can be used without particular limitation.
- anionic polymerization of an epoxy group and a phenolic hydroxyl group, an epoxy group and an amino group, and an epoxy group are preferable from the viewpoint of durability.
- the second embodiment specifically includes the following embodiments (2-1) to (2-4), but it should not be construed as being limited to the following embodiments.
- the continuous phase contains a reaction product of the resin component A containing the reversible bond and a curing agent, wherein the discontinuous phase comprises a reaction product of resin component B and a curing agent; the functional group (a1) in the continuous phase is reactive with the functional group (b1) in the discontinuous phase,
- the phase-separated structure can comprise reaction products of functional groups (a1) in the continuous phase and functional groups (b1) in the discontinuous phase.
- the continuous phase contains a self-polymerization product of the resin component A containing the reversible bond
- the discontinuous phase comprises a self-polymerization product of resin component B
- the functional group (a1) in the continuous phase is reactive with the functional group (b1) in the discontinuous phase
- the phase-separated structure can comprise reaction products of functional groups (a1) in the continuous phase and functional groups (b1) in the discontinuous phase.
- the continuous phase contains a reaction product of the resin component A containing the reversible bond and a curing agent
- the discontinuous phase comprises a self-polymerization product of resin component B
- the functional group (a1) in the continuous phase is reactive with the functional group (b1) in the discontinuous phase
- the phase-separated structure can comprise reaction products of functional groups (a1) in the continuous phase and functional groups (b1) in the discontinuous phase.
- the continuous phase contains a self-polymerization product of the resin component A containing the reversible bond, wherein the discontinuous phase comprises a reaction product of resin component B and a curing agent; the functional group (a1) in the continuous phase is reactive with the functional group (b1) in the discontinuous phase,
- the phase-separated structure can comprise reaction products of functional groups (a1) in the continuous phase and functional groups (b1) in the discontinuous phase.
- the present invention is characterized by containing a reversible bond in the continuous phase.
- the resin component A may contain (introduce) a reversible bond preferable.
- the resin component A containing a reversible bond for example, a monomer component or a polymer component (hereinafter sometimes referred to as "monomer component etc.") and a reversible bond having reactivity with the monomer component etc.
- a reversible bond can be contained (introduced) in the resin component A by reacting a compound capable of forming can contain (introduce)
- the compound C a single compound or a plurality of compounds can be used.
- a method for containing (introducing) a reversible bond in the resin component A a plurality of compounds (for example, “compound C′” and “compound C′′”) different from the monomer component etc. ) to form a reversible bond in the resin component A due to the plurality of other compounds.
- the resin component A when the resin component A is a polymer, it may be formed in either the side chain or the main chain, and from the viewpoint of flexibility, it is more preferably formed in the side chain. From the viewpoint of heat resistance, it is more preferably formed on the main chain.
- the structure of the resin component A is the same or similar, it is more preferably formed in the side chain from the viewpoint of repairability, and formed in the main chain from the viewpoint of remolding. more preferred.
- Resin Component A and Resin Component B Regarding the resin component (or resin composition) A capable of forming the continuous phase and the resin component (or resin composition) B capable of forming the discontinuous phase, each resin component (or resin composition) Due to the difference in tensile elastic modulus of the cured product, the compound C caused by the reversible bond introduced into the continuous phase, the difference in reactivity between the monomer component etc. and the compound C' and the compound C'', etc. It can be selected as appropriate.
- the resin component A and the resin component B include epoxy resin (epoxy compound), acrylic resin (acrylic polymer), silicone resin (silicone polymer), urethane resin (urethane polymer), Maleimide resins (maleimide compounds), phenol resins, unsaturated polyester resins, melamine resins, urea resins, diallyl phthalate resins, benzoxazine resins (polybenzoxazine), cyanate ester resins, and the like.
- the resin component A and the resin component B for example, an epoxy resin and another epoxy resin (each having a difference in tensile elastic modulus of a cured product obtained using a single epoxy resin)
- a combination of epoxy resin and other resins for example, acrylic resin, silicone resin, urethane resin, etc.
- Epoxy resin By using an epoxy resin for the crosslinkable resin composition, a cured product having excellent heat resistance, mechanical strength, adhesive strength, and electrical insulation can be obtained, which is useful.
- a method for preparing the epoxy resin a known and commonly used method can be adopted.
- epoxy resin examples include, but are not limited to, phenol novolak type epoxy resin, cresol novolak type epoxy resin, ⁇ -naphthol novolak type epoxy resin, ⁇ -naphthol novolak type epoxy resin, bisphenol A novolak type epoxy resin, and biphenyl novolak type epoxy resin.
- novolak type epoxy resins such as type epoxy resin; aralkyl type epoxy resins such as phenol aralkyl type epoxy resin, naphthol aralkyl type epoxy resin, phenol biphenyl aralkyl type epoxy resin; bisphenol A type epoxy resin, bisphenol AP type epoxy resin, bisphenol AF type Bisphenol types such as epoxy resin, bisphenol B type epoxy resin, bisphenol BP type epoxy resin, bisphenol C type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, tetrabromobisphenol A type epoxy resin Epoxy resin; biphenyl type epoxy resin such as biphenyl type epoxy resin, tetramethylbiphenyl type epoxy resin, epoxy resin having biphenyl skeleton and diglycidyloxybenzene skeleton; naphthalene type epoxy resin; naphthylene ether type epoxy resin; binaphthol type epoxy resin ; binaphthyl type epoxy resin; dicyclopenta
- epoxy resins contain a high concentration of an aromatic skeleton exemplified by benzene and naphthalene.
- phenol novolac type epoxy resins cresol novolak type epoxy resins, and ⁇ -naphthol novolak type epoxy resins that tend to give cured products with a high tensile modulus (for example, a cured product with a tensile modulus of 1500 MPa or more).
- ⁇ -naphthol novolac type epoxy resin bisphenol A novolac type epoxy resin, biphenyl novolac type epoxy resin, etc.
- phenol aralkyl type epoxy resin naphthol aralkyl type epoxy resin, phenol biphenyl aralkyl type epoxy resin, etc.
- Epoxy resin bisphenol A type epoxy resin, bisphenol AP type epoxy resin, bisphenol AF type epoxy resin, bisphenol B type epoxy resin, bisphenol BP type epoxy resin, bisphenol C type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin , bisphenol S-type epoxy resin, tetrabromobisphenol A-type epoxy resin and the like; Resin; Naphthalene type epoxy resin; Naphthylene ether type epoxy resin; Binaphthol type epoxy resin; Binaphthyl type epoxy resin; Dicyclopentadiene type epoxy resin such as dicyclopentadiene phenol type epoxy resin; -glycidylamine type epoxy resins such as p-aminophenol type epoxy resins and diaminodiphenylsulfone glycidylamine type epoxy resins; 2,6-naphthalenedicarboxylic acid diglycidyl ester type epoxy resins and hexahydrophthalic anhydride glycidyl ester type epoxy
- a flexible aliphatic skeleton (including one containing a heteroatom) is additionally introduced into a rigid aromatic skeleton, or an aromatic It can be realized by replacing the tribal skeleton with an aliphatic skeleton.
- the introduction of the aliphatic skeleton into the skeleton of the epoxy resin not only adjusts the rigidity of the molecule, but also reduces the crosslink density by introducing the aliphatic skeleton in the direction of the side chain. By additionally introducing it in the direction, it is possible to exhibit the effect of lowering the elastic modulus in terms of the higher-order structure of the cured product, such as increasing the cross-linking point distance in the obtained cured product, which is preferable.
- epoxy resins from which a cured product having a low elastic modulus for example, a cured product having a tensile elastic modulus of less than 1000 MPa
- Copolymerization type epoxy resins having a flexible skeleton in which the above atoms are linked in a straight chain and a rigid skeleton such as bisphenol are exemplified.
- the above epoxy resin when used in the crosslinkable resin composition of the present invention, it may contain a curing accelerator.
- a curing accelerator Various curing accelerators can be used, and examples include urea compounds, phosphorus compounds, tertiary amines, imidazoles, organic acid metal salts, Lewis acids, amine complex salts, quaternary ammonium salts, and tin carboxylic acid. Salts, organic peroxides and the like can be mentioned.
- inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid
- organic acids such as p-toluenesulfonic acid, monoisopropyl phosphate, and acetic acid
- sodium hydroxide, potassium hydroxide, etc. tetraisopropyl titanate of titanate esters
- Inorganic bases such as tetrabutyl titanate; 1,8-diazabicyclo[5.4.0]undecene-7 (DBU), 1,5-diazabicyclo[4.3.0]nonene-5 (DBN), 1,4 -diazabicyclo[2.2.2]octane (DABCO), tri-n-butylamine, dimethylbenzylamine, monoethanolamine, imidazole, 2-ethyl-4-methyl-imidazole, 1-methylimidazole, N,N-dimethyl -Compounds containing a basic nitrogen atom such as 4-aminopyridine (DMAP); urea
- the above epoxy resin when used in the crosslinkable resin composition of the present invention, it can be cured with active energy rays.
- a photocationic polymerization initiator may be used as the polymerization initiator. Visible light, ultraviolet rays, X-rays, electron beams, and the like can be used as active energy rays.
- photocationic polymerization initiator examples include aryl-sulfonium salts, aryl-iodonium salts, etc. Specific examples include arylsulfonium hexafluorophosphate, arylsulfonium hexafluoroantimonate, and arylsulfonium tetrakis(pentafluoro)boric acid. Salts, tri(alkylphenyl)sulfonium hexafluorophosphate, and the like can be used.
- the photocationic polymerization initiators may be used alone or in combination of two or more.
- a urea compound particularly 3-(3,4-dichlorophenyl)-1, is preferred because of its excellent workability and low-temperature curability.
- DCMU 1-dimethylurea
- the crosslinkable resin composition containing the epoxy resin is used as an electronic material such as a semiconductor encapsulating material, a printed circuit board, or a build-up board, curability, heat resistance, electrical properties, and moisture resistance reliability etc.
- triphenylphosphine is preferred as a phosphorus compound
- dimethylaminopyridine and imidazoles as tertiary amines
- benzyldimethylamine are preferred. .
- the above epoxy resin when used in the crosslinkable resin composition of the present invention, it may contain a curing agent.
- Various curing agents can be used, and examples thereof include amine compounds, acid anhydride compounds, amide compounds, phenol compounds and carboxylic acid compounds.
- amine compounds examples include aliphatic polyamines such as ethylenediamine, propylenediamine, butylenediamine, hexamethylenediamine, polypropyleneglycoldiamine, diethylenetriamine, triethylenetetramine, and pentaethylenehexamine; metaxylylenediamine; diaminodiphenylmethane; Aromatic polyamines such as diaminodiphenylsulfone and phenylenediamine; alicyclic polyamines such as 1,3-bis(aminomethyl)cyclohexane, isophoronediamine and norbornanediamine; and dicyandiamide.
- aliphatic polyamines such as ethylenediamine, propylenediamine, butylenediamine, hexamethylenediamine, polypropyleneglycoldiamine, diethylenetriamine, triethylenetetramine, and pentaethylenehexamine
- metaxylylenediamine dia
- acid anhydride compounds examples include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, polypropylene glycol maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, and methyl nadic anhydride. , hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, and the like.
- amide compounds examples include aliphatic polyamide synthesized from polycarboxylic acid and polyamine, aromatic polyamide obtained by introducing an aromatic ring into this, aliphatic polyamide adduct obtained by adding an epoxy compound to polyamide, aromatic family polyamide adducts, and the like.
- phenol-based compound examples include phenol novolak resin, cresol novolak resin, aromatic hydrocarbon formaldehyde resin-modified phenol resin, dicyclopentadiene phenol addition type resin, phenol aralkyl resin, naphthol aralkyl resin, trimethylolmethane resin, tetraphenyl Roll ethane resin, naphthol novolac resin, naphthol-phenol co-condensed novolac resin, naphthol-cresol co-condensed novolak resin, biphenyl-modified phenol resin, aminotriazine-modified phenol resin, modified products thereof, and the like.
- latent catalysts examples include imidazole, BF3-amine complexes, guanidine derivatives and the like.
- carboxylic acid-based compound examples include carboxylic acid-terminated polyesters, polyacrylic acid, carboxylic acid polymers such as maleic acid-modified polypropylene glycol, and active ester resins.
- curing agents can be used singly or in combination of two or more. Moreover, the content of the curing agent can be appropriately set according to the purpose, and is not limited to a specific range. In applications such as underfill materials and general paint applications, it is preferable to use the amine-based compound, carboxylic acid-based compound, and/or acid anhydride-based compound. Amine-based compounds, particularly dicyandiamide, are preferred for use as adhesives and flexible wiring boards in terms of workability, curability, and long-term stability. Further, in semiconductor encapsulation applications, a solid type phenolic compound is preferable from the viewpoint of heat resistance of the cured product.
- ⁇ Acrylic resin (acrylic polymer), etc.> By using an acrylic resin (acrylic polymer) or the like in the crosslinkable resin composition, rapid curability can be imparted, and a cured product having excellent flexibility can be obtained, which is useful.
- a method for preparing the acrylic resin or the like a known and commonly used method can be adopted. For example, when using only a monomer, in advance, a polymer obtained by polymerizing a monomer is used in combination with the monomer. In some cases, a case in which a polymer polymerized in advance is used can be exemplified.
- the monomer unit constituting the acrylic resin is not particularly limited, but examples include glycidyl (meth)acrylate, ⁇ -ethyl glycidyl (meth)acrylate, ⁇ -n-propyl glycidyl (meth)acrylate, ⁇ -n-butyl (meth)glycidyl acrylate, -3,4-epoxybutyl (meth)acrylate, -4,5-epoxypentyl (meth)acrylate, -6,7-epoxypentyl (meth)acrylate, ⁇ -ethyl (meth)acrylate-6,7-epoxypentyl, ⁇ -methylglycidyl (meth)acrylate, (meth)acrylate-3,4-epoxycyclohexyl, lactone-modified (meth)acrylate-3,4- epoxycyclohexyl, vinylcyclohexene oxide; (meth) methyl acrylate, eth
- Acrylic acid esters having a hydroxyalkyl group such as (meth) acrylic acid esters having a polyalkylene glycol group; Unsaturated dicarboxylic acid esters such as dimethyl fumarate, diethyl fumarate, dibutyl fumarate, dimethyl itaconate, dibutyl itaconate, methyl ethyl fumarate, methyl butyl fumarate, methyl ethyl itaconate; Styrene derivatives such as styrene, ⁇ -methylstyrene, chlorostyrene; diene compounds such as butadiene, isoprene, piperylene, dimethylbutadiene; Vinyl halides such as vinyl chloride and vinyl bromide, and vinylidene halides; unsaturated ketones such as methyl vinyl ketone, butyl vinyl ketone; vinyl esters such as vinyl acetate and vinyl butyrate; vinyl ethers such as methyl vinyl ether, butyl vinyl
- the monomer unit can prepare the acrylic resin (acrylic polymer) and the like by using a polymerization initiator.
- polymerization initiator examples include 2,2′-azobisisobutyronitrile, 2,2′-azobis-(2,4-dimethylvaleronitrile), 2,-azobis-(4-methoxy-2, 4-dimethylvaleronitrile) and other azo compounds; benzoyl peroxide, lauroyl peroxide, t-butylperoxypivalate, t-butylperoxyethylhexanoate, 1,1'-bis-(t-butylperoxy)cyclohexane, t -Amylperoxy-2-ethylhexanoate, t-hexylperoxy-2-ethylhexanoate and other organic peroxides and hydrogen peroxide.
- benzoyl peroxide lauroyl peroxide, t-butylperoxypivalate, t-butylperoxyethylhexanoate, 1,1'-bis-(t-butylperoxy)
- acrylic resins whose cured products tend to have a high tensile modulus include monomers with short fatty chains such as methyl methacrylate, and rigid resins such as isobornyl methacrylate, dicyclopentanyl methacrylate, and styrene. Increase the rigidity of the molecule by using many monomers with alicyclic or aromatic skeletons, or increase the cross-linking density by using monomers that act as cross-linking agents such as divinylbenzene and bisphenol A diglycidyl methacrylate.
- a cured product having a high elastic modulus can be obtained by, for example,
- acrylic resins whose cured products tend to have a low tensile modulus include 2-ethylhexyl acrylate, n-butyl acrylate, lauryl acrylate, and other flexible long-chain aliphatic skeletons (without heteroatoms).
- monomers that contain including those containing It is possible to exhibit the effect of lowering the modulus of elasticity of the cured product in terms of the higher-order structure, such as by enlarging it, which is preferable.
- the acrylic resin or the like described above when used in the crosslinkable resin composition of the present invention, it may contain a crosslinker.
- the cross-linking agent here can exhibit the same performance as the curing agent in the above (Embodiment 1) and (Embodiment 2), and can be rephrased as a curing agent.
- Various cross-linking agents can be used as the cross-linking agent.
- These cross-linking agents can be used singly or in combination of two or more.
- the content of the cross-linking agent can be appropriately set according to the desired degree of cross-linking, and is not limited to a specific range.
- Silicone-based polymer By using a silicone-based resin in the crosslinkable resin composition, a cured product having excellent flexibility and sealability is obtained, which is useful.
- a method for preparing the silicone-based resin a known and commonly used method can be employed.
- a silane compound having an alkoxy group represented by the following formula (1) can be used to prepare the silicone-based resin (eg, organopolysiloxane).
- Si(OR 1 ) n R 2 4-n (1)
- n 2, 3 or 4
- R 1 represents an alkyl group
- R 2 represents an organic group.
- Examples of the compound represented by formula (1) include dialkoxysilanes such as dimethyldimethoxysilane, dimethyldiethoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, diphenyldimethoxysilane, and diphenyldiethoxysilane; Trialkoxysilanes such as silane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane; tetraalkoxysilanes such as tetramethoxysilane, tetraethoxysilane, tetraisopropyloxysilane; (meth)acryloxyalkyltrialkoxysilanes such as ⁇ -(meth)acryloxypropyltrimethoxysilane and ⁇ -(meth)acryloxyprop
- organopolysiloxane examples include those represented by the following formula (2).
- n can be a numerical value corresponding to the molecular weight of the organopolysiloxane.
- the compound represented by the above formula (2) can be produced, for example, by modifying polysiloxane having silanol groups at both ends with tetramethoxysilane.
- the organopolysiloxane the one represented by the above formula (2) and the diorganopolysiloxane blocked with a hydrolytic condensate of alkoxysilane are preferable.
- methoxysilanes having a flexible skeleton in the main chain such as methoxysilane-terminated propylene glycol polymers, and those whose terminals are modified with aminopropyltrimethoxysilane or the like.
- the condensation catalyst that can be used in the preparation of the silicone resin (organopolysiloxane) is not particularly limited as long as it is a catalyst used for condensation of silanol groups and hydrolyzable silyl groups.
- the condensation catalyst can be metal salts; complexes; alcoholates; oxides; multimetallic oxides, salts and/or complexes thereof; or combinations thereof.
- the condensation catalyst is preferably a metal salt compound from the viewpoint of excellent room temperature stability and curability.
- the condensation catalyst is a metal compound containing at least one selected from the group consisting of Al, Zn, Sn, Zr, Hf, Ti and lanthanoids, from the viewpoint of excellent curability and room temperature stability.
- it is a metal salt compound.
- aluminum compounds include tris(acetylacetonate)aluminum, tris(ethylacetoacetate)aluminum, alkylacetoacetate aluminum diisopropylate such as ethylacetoacetate aluminum diisopropylate, and aluminum such as aluminum butoxybisethylacetoacetate.
- chelates aluminum salts such as aluminum octylate, compounds containing cyclic aluminum oxide, aluminum triacetate, aluminum tristearate; aluminum sec-butylate, aluminum triethoxide, aluminum triisopropoxide, alkoxyarylaluminates, etc. aluminum alcoholates.
- Zinc compounds include aliphatic carboxylic acids such as zinc acetate, zinc acetylacetate, zinc 2-ethylhexanoate, zinc octylate, zinc neodecanoate, zinc laurate, and zinc stearate.
- carboxylates such as zinc, alicyclic zinc carboxylates such as zinc naphthenate, zinc benzoate, zinc p-tert-butylbenzoate, and zinc aromatic carboxylates such as zinc salicylate; zinc (meth)acrylate; Zinc chelates such as zinc acetylacetonate [Zn(II) acetylacetonate, Zn(acac) 2 ], 2,2,6,6-tetramethyl-3,5-heptanedionate Zn.
- Zinc chelates such as zinc acetylacetonate [Zn(II) acetylacetonate, Zn(acac) 2 ], 2,2,6,6-tetramethyl-3,5-heptanedionate Zn.
- tetravalent tin such as dibutyltin diacetate, dibutyltin dioleate, dibutyltin dilaurate, dibutyltin oxyacetate, dibutyltinoxyoctylate, and dibutyltinoxylaurate is used from the viewpoint of excellent curability and room temperature stability.
- metal salt compounds of; divalent tin metal salt compounds such as bis(2-ethylhexanoic acid) tin are preferred.
- the zirconium compound is preferably an aliphatic carboxylate and/or an alicyclic carboxylate, more preferably an alicyclic carboxylate.
- aliphatic carboxylates such as zirconyl dioctylate and zirconyl dineodecanoate
- alicyclic carboxylates such as zirconyl naphthenate and zirconyl cyclohexanoate
- aromatic carboxylates such as zirconyl benzoate.
- lanthanoid compounds examples include lanthanoid 2-ethylhexanoate and lanthanoid naphthenate.
- 2-ethylhexanoate of lanthanum, cerium, dysprosium or ytterbium is preferable from the viewpoint that the composition of the present invention has excellent heat curability, and 2-ethylhexanoate of cerium (tris(2-ethylhexane acid) cerium) is more preferred.
- titanium compounds examples include alcoholates such as tetraethoxytitanium, tetraisopropoxytitanium, tetrabutoxytitanium and tetraoctoxytitanium; Metal salt compounds are mentioned.
- Silicone-based resins whose cured products tend to have a high tensile modulus include, for example, phenyltrimethoxysilane, phenyltriethoxysilane, and other monomers having a rigid aromatic skeleton. It is conceivable to increase cross-linking density by using a large amount of tetrafunctional alkoxysilane such as tetramethoxysilane, tetraethoxysilane, and tetraisopropyloxysilane.
- bifunctional alkoxysilanes such as dimethyldimethoxysilane, dimethyldiethoxysilane, diethyldimethoxysilane, and diethyldiethoxysilane are often used.
- the higher-order structure of the cured product such as reducing the crosslink density and increasing the crosslink point distance of the cured product by using a methoxysilane-terminated propylene glycol polymer or a linear polymer with a weight average molecular weight of 100,000 or more. It is possible to exhibit the effect of lowering the elastic modulus, which is preferable.
- the silicone-based resin when used in the crosslinkable resin composition of the present invention, it may contain a crosslinker.
- a crosslinking agent various agents can be used.
- a siloxane-based cross-linking agent sicone-based cross-linking agent having a hydrosilyl group (SiH group), a peroxide-based cross-linking agent, or the like can be used.
- These cross-linking agents can be used singly or in combination of two or more.
- the content of the cross-linking agent can be appropriately set according to the desired degree of cross-linking, and is not limited to a specific range.
- the resin component A and the resin component B in addition to epoxy resins, acrylic resins, silicone resins, etc., the characteristics of the cured product obtained using the crosslinkable resin composition of the present invention are not impaired.
- Other resins can be used within the range.
- the other resin for example, when an epoxy resin is used as the resin component A or the resin component B, in a low temperature range, it dissolves with the epoxy resin to form a one-phase solution, while in a high temperature range, Examples include thermoplastic resins such as polyethersulfone, which are known to be immiscible, and liquid nitrile rubbers (such as CTBN and ATBN) that have carboxyl groups and amino groups at both ends and can react with epoxy groups. .
- the compound C is a compound already containing a reversible bond in its structure (skeleton), and the resin component A A reversible bond resulting from the compound C is directly introduced into the structure (skeleton) of the resin component A by reacting with .
- a method for containing (introducing) a reversible bond in the resin component A by reacting the compound C′ and the compound C′′, for example, together with the monomer component, etc. the compound C′ and the By mixing and reacting the compound C'', the reactive functional groups of the compound C' and the compound C'' react with each other, thereby indirectly forming a resin formed from the monomer components and the like.
- a reversible bond generated by the reaction between the compound C' and the compound C'' is introduced.
- the reactive functional group of the compound C′′ becomes the reactive functional group in the precursor.
- a case in which a reversible bond is contained (introduced) into the resin component A by reacting with a group is exemplified.
- a cured product obtained by using a resin component into which a reversible bond has been introduced in this way may be cut at the reversible bond portion when, for example, the cured product is impacted and cracks or pulverizes.
- the reversible bond is reversibly reshaped even in a low temperature range including room temperature, and can exhibit functions such as repairability and remolding, so it is suitable for low temperature repairability and low temperature remolding. It is useful because it can give an excellent cured product.
- reversible bonding can be achieved by placing it in a low temperature including room temperature or a heated/heated state. Based on this, the cured product can be repaired and reshaped.
- a covalent bond system and a non-covalent bond system are mentioned, and from the viewpoint of the durability of the cured product, a covalent bond system is preferable.
- a non-covalent bonding system is preferable from the viewpoint of a short recovery time after pulverization of the cured product and a short remolding time.
- the covalent bond system is not particularly limited.
- a furanone skeleton, an amide bond, and the like can be mentioned.
- an addition type structure by Diels-Alder reaction is preferable from the viewpoint of hydrolysis resistance of the cured product.
- the non-covalent bond system is not particularly limited, but includes, for example, van der Waals force, ionic bond, inclusion bond of cyclodextrin, hydrogen bond such as ureidopyrimidinone unit and polyetherthiourea. Among them, hydrogen bonding is preferable from the viewpoint of shortening the repair time and reforming time.
- the following compound here, corresponding to compound C
- Examples of compounds having an addition structure obtained by the Diels-Alder reaction include the compounds shown below.
- Examples of the compound containing the disulfide bond include the compounds shown below.
- Examples of the compound containing the alkoxyamine skeleton include the compounds shown below.
- Examples of the compound containing the diarylbibenzofuranone skeleton include the compounds shown below.
- Examples of the compound C' and the compound C'' include the following compounds (precursor compounds). It is preferable to use a compound that becomes a body.
- Examples of the precursor compound of the addition structure formed by the Diels-Alder reaction include the compounds shown below.
- examples of the precursor compounds include precursor compounds that form hydrogen bonds, and the compounds shown below are examples thereof.
- the molar concentration (mmol/g) of reversible bonds in the crosslinkable resin composition of the present invention is the total mass of resin component A, resin component B, and compound C (total of compound C′ and compound C′′). is preferably 0.10 mmol/g or more. According to such a configuration, both the repairability and remoldability of the crosslinkable resin cured product obtained by subjecting the crosslinkable resin composition to heat treatment are further improved.
- the molar concentration of the reversible bond is more preferably 0.10 to 3.00 mmol/g, still more preferably 0.15 to 2.00 mmol/g.
- the molar concentration of the reversible bond in the crosslinkable resin composition of the present invention is the resin component A, the resin component In addition to B and compound C (the sum of compound C' and compound C''), the total mass (g number) of the resin that can be used in combination is preferably 0.10 mmol/g or more , more preferably 0.10 to 3.00 mmol/g, still more preferably 0.15 to 2.00 mmol/g.
- the molar concentration of the reversible bond can be calculated by the following formula. The number of moles of reversible bonds is the theoretical number of moles.
- the molar concentration of the reversible bond is determined by the glass transition temperature (Tg) defined by the tan ⁇ peak top of a dynamic viscoelasticity measuring instrument (DMA) of the cured product obtained from the target crosslinkable resin composition. It can be selected as appropriate. For example, when the glass transition temperature (Tg) (° C.) is used as a guideline, when obtaining a cured product whose temperature is around room temperature, sufficient repairability and remolding function are expressed even at the low molar concentration side of the preferable range. easier. On the other hand, if the intended cured product has a glass transition temperature of more than 100° C. as a guide, the function is likely to be exhibited at the high molar concentration side of the preferred range.
- Tg glass transition temperature
- DMA dynamic viscoelasticity measuring instrument
- the glass transition temperature measured by a dynamic viscoelasticity analyzer is the temperature at which the dynamic elastic modulus of the cured product drops sharply, in a temperature range exceeding this temperature, the concentration of reversible bonds is Even if it is low, sufficient repairability and remolding functions are likely to be expressed, so it is also possible to appropriately adjust the aging temperature for repair and the heating temperature for remolding. can be adjusted, and the relationship between the glass transition temperature of the cured product and the molar concentration of the reversible bond is not limited to these.
- the crosslinkable resin composition of the present invention may further contain a filler.
- Fillers include inorganic fillers and organic fillers. Examples of inorganic fillers include inorganic fine particles.
- Examples of the inorganic fine particles having excellent heat resistance include alumina, magnesia, titania, zirconia, silica (quartz, fumed silica, precipitated silica, silicic anhydride, fused silica, crystalline silica, ultrafine powder-free Formed silica, etc.), etc.; those with excellent thermal conductivity include boron nitride, aluminum nitride, alumina oxide, titanium oxide, magnesium oxide, zinc oxide, silicon oxide, diamond, etc.; those with excellent conductivity include simple metals or alloys.
- metal fillers and/or metal-coated fillers metal fillers and/or metal-coated fillers; excellent barrier properties include mica and clay , kaolin, talc, zeolite, wollastonite, smectite, etc., potassium titanate, magnesium sulfate, sepiolite, xonolite, aluminum borate, calcium carbonate, titanium oxide, barium sulfate, zinc oxide, magnesium hydroxide; barium titanate, zirconia oxide, titanium oxide, etc.; those exhibiting photocatalytic properties include titanium, cerium, zinc, copper, aluminum, tin, indium, phosphorus, carbon, sulfur, terium, nickel, iron , cobalt, silver, molybdenum, strontium, chromium, barium, lead and other photocatalytic metals, composites of the above metals, oxides thereof, etc.; Metals, their composites and oxides, etc.
- examples thereof include titanium oxide and zinc oxide.
- These inorganic fine particles may be appropriately selected depending on the application, and may be used alone or in combination of multiple types. In addition, since the inorganic fine particles have various properties other than the properties listed as examples, they may be appropriately selected according to the intended use.
- silica fine particles such as powdered silica and colloidal silica can be used without any particular limitation.
- powdery silica fine particles include Aerosil 50 and 200 manufactured by Nippon Aerosil Co., Ltd., Sildex H31, H32, H51, H52, H121, H122 manufactured by Asahi Glass Co., Ltd., and E220A manufactured by Nippon Silica Industry Co., Ltd. , E220, SYLYSIA470 manufactured by Fuji Silysia Co., Ltd., SG flake manufactured by Nippon Sheet Glass Co., Ltd., and the like.
- colloidal silica includes, for example, Nissan Chemical Industries, Ltd. methanol silica sol, IPA-ST, MEK-ST, NBA-ST, XBA-ST, DMAC-ST, ST-UP, ST-OUP, ST-20, ST-40, ST-C, ST-N, ST-O, ST-50, ST-OL and the like can be mentioned.
- surface-modified silica fine particles may be used.
- the silica fine particles are surface-treated with a reactive silane coupling agent having a hydrophobic group, or modified with a compound having a (meth)acryloyl group.
- a reactive silane coupling agent having a hydrophobic group or modified with a compound having a (meth)acryloyl group.
- I can give you something.
- Commercially available powdery silica modified with a compound having a (meth)acryloyl group includes Aerosil RM50 and R711 manufactured by Nippon Aerosil Co., Ltd.
- Commercially available colloidal silica modified with a compound having a (meth)acryloyl group includes: Examples include MIBK-SD manufactured by Nissan Chemical Industries, Ltd., and the like.
- the shape of the silica fine particles is not particularly limited, and may be spherical, hollow, porous, rod-like, plate-like, fibrous, or amorphous.
- the primary particle size is preferably in the range of 5 to 200 nm. If the particle size is less than 5 nm, the inorganic fine particles are not sufficiently dispersed in the dispersion, and if the particle size exceeds 200 nm, the cured product may not have sufficient mechanical strength.
- titanium oxide fine particles not only extender pigments but also ultraviolet light-responsive photocatalysts can be used, such as anatase-type titanium oxide, rutile-type titanium oxide, and brookite-type titanium oxide. Furthermore, particles designed to respond to visible light by doping a different element into the crystal structure of titanium oxide can also be used.
- Anion elements such as nitrogen, sulfur, carbon, fluorine, and phosphorus, and cationic elements such as chromium, iron, cobalt, and manganese are preferably used as elements to be doped in titanium oxide.
- a powder, a sol dispersed in an organic solvent or water, or a slurry can be used as a form.
- Examples of commercially available powdery titanium oxide fine particles include Aerosil P-25 manufactured by Nippon Aerosil Co., Ltd., and ATM-100 manufactured by Tayca Corporation. Further, commercially available slurry-like titanium oxide fine particles include, for example, TKD-701 manufactured by Tayka Co., Ltd., and the like.
- the crosslinkable resin composition of the present invention may further contain a fibrous matrix.
- the fibrous substrate of the present invention is not particularly limited, but is preferably used for fiber-reinforced resins, and includes inorganic fibers and organic fibers.
- the inorganic fibers include inorganic fibers such as carbon fiber, glass fiber, boron fiber, alumina fiber, silicon carbide fiber, carbon fiber, activated carbon fiber, graphite fiber, glass fiber, tungsten carbide fiber, silicon carbide fiber (silicon carbide fiber). fibers), ceramic fibers, alumina fibers, natural fibers, mineral fibers such as basalt, boron fibers, boron nitride fibers, boron carbide fibers, and metal fibers.
- the metal fibers include aluminum fibers, copper fibers, brass fibers, stainless steel fibers, and steel fibers.
- organic fibers examples include synthetic fibers made of resin materials such as polybenzazole, aramid, PBO (polyparaphenylenebenzoxazole), polyphenylene sulfide, polyester, acrylic, polyamide, polyolefin, polyvinyl alcohol, and polyarylate, cellulose, and pulp. , natural fibers such as cotton, wool and silk, and regenerated fibers such as proteins, polypeptides and alginic acid.
- resin materials such as polybenzazole, aramid, PBO (polyparaphenylenebenzoxazole), polyphenylene sulfide, polyester, acrylic, polyamide, polyolefin, polyvinyl alcohol, and polyarylate, cellulose, and pulp.
- natural fibers such as cotton, wool and silk
- regenerated fibers such as proteins, polypeptides and alginic acid.
- carbon fiber and glass fiber are preferable as the fibrous substrate because of their wide industrial application.
- carbon fiber and glass fiber are preferable as the fibrous substrate because of their wide industrial application.
- only one type may be used, and multiple types may be used simultaneously.
- the fibrous substrate of the present invention may be an aggregate of fibers, and the fibers may be continuous or discontinuous, and may be woven or nonwoven. Moreover, it may be a fiber bundle in which fibers are aligned in one direction, or may be in the form of a sheet in which fiber bundles are arranged. Moreover, it may have a three-dimensional shape in which a fiber aggregate has a thickness.
- a dispersion medium may be used in the crosslinkable resin composition of the present invention for the purpose of adjusting the solid content and viscosity of the crosslinkable resin composition.
- the dispersion medium may be any liquid medium that does not impair the effects of the present invention, and includes various organic solvents, liquid organic polymers, and the like.
- organic solvent examples include ketones such as acetone, methyl ethyl ketone (MEK) and methyl isobutyl ketone (MIBK); cyclic ethers such as tetrahydrofuran (THF) and dioxolane; and esters such as methyl acetate, ethyl acetate and butyl acetate. , toluene, xylene, and other aromatics; carbitol, cellosolve, methanol, isopropanol, butanol, propylene glycol monomethyl ether, and other alcohols; these can be used alone or in combination; It is preferable from the viewpoint of volatility during processing and solvent recovery.
- ketones such as acetone, methyl ethyl ketone (MEK) and methyl isobutyl ketone (MIBK)
- cyclic ethers such as tetrahydrofuran (THF) and dioxolane
- esters such as
- the liquid organic polymer is a liquid organic polymer that does not directly contribute to the curing reaction, and examples thereof include carboxyl group-containing modified polymers (Floren G-900, NC-500: Kyoeisha), acrylic polymers (Floren WK-20: Kyoeisha). , amine salt of special modified phosphoric acid ester (HIPLAAD ED-251: Kusumoto Kasei), modified acrylic block copolymer (DISPERBYK2000; BYK-Chemie), and the like.
- carboxyl group-containing modified polymers Floren G-900, NC-500: Kyoeisha
- acrylic polymers Floren WK-20: Kyoeisha
- amine salt of special modified phosphoric acid ester HPLAAD ED-251: Kusumoto Kasei
- modified acrylic block copolymer DISPERBYK2000; BYK-Chemie
- the crosslinkable resin composition of the present invention may contain resins other than the various resins and compounds described above.
- resins known and commonly used resins may be blended as long as they do not impair the effects of the present invention.
- thermosetting resins and thermoplastic resins can be used.
- thermosetting resin is a resin that has the property of being substantially insoluble and infusible when cured by means of heat, radiation, or a catalyst.
- Specific examples thereof include phenol resins, urea resins, melamine resins, benzoguanamine resins, alkyd resins, unsaturated polyester resins, vinyl ester resins, diallyl terephthalate resins, silicone resins, urethane resins, furan resins, ketone resins, xylene resins, heat Examples include curable polyimide resins, benzoxazine resins, active ester resins, aniline resins, cyanate ester resins, styrene/maleic anhydride (SMA) resins, and maleimide resins.
- SMA styrene/maleic anhydride
- the thermoplastic resin refers to a resin that can be melt-molded by heating. Specific examples thereof include polyethylene resins, polypropylene resins, polystyrene resins, rubber-modified polystyrene resins, acrylonitrile-butadiene-styrene (ABS) resins, acrylonitrile-styrene (AS) resins, polymethyl methacrylate resins, acrylic resins, and polyvinyl chloride resins.
- thermoplastic resins examples include syndiotactic polystyrene resins and cyclic polyolefin resins. These thermoplastic resins can be used singly or in combination of two or more.
- the crosslinkable resin composition of the present invention may contain other ingredients.
- catalysts other than those mentioned above polymerization initiators, inorganic pigments, organic pigments, extenders, clay minerals, waxes, surfactants, stabilizers, flow modifiers, coupling agents, dyes, leveling agents, rheology control agents , ultraviolet absorbers, antioxidants, flame retardants, plasticizers, reactive diluents, and the like.
- the difference in tensile modulus between the discontinuous phase and the continuous phase is preferably 1000 MPa or more, more preferably 1500 MPa or more, and 2000 MPa or more. More preferred. Having the above difference in tensile modulus is useful because it is possible to achieve both mechanical strength and flexibility.
- the continuous phase preferably has a tensile modulus of less than 1000 MPa, more preferably 0.1 MPa to 500 MPa, even more preferably 0.1 MPa to 100 MPa. It is preferable that the tensile modulus of the continuous phase is within the above range because the repairability effect is enhanced.
- the discontinuous phase preferably has a tensile modulus of 1500 MPa to 6000 MPa, more preferably 2000 MPa to 5000 MPa, and even more preferably 2000 MPa to 4000 MPa.
- the heat distortion temperature is increased, which is preferable.
- the crosslinkable resin composition of the present invention is preferably a composition for repair/remolding materials.
- the crosslinkable resin composition forms a phase-separated structure when a cured product is formed, and can exhibit mechanical strength due to the discontinuous phase with a high elastic modulus, while reversibly bonding to the continuous phase with a low elastic modulus.
- the molecular mobility becomes good, flexibility is imparted, and even if cracks occur in the cured product, it exhibits repairability and re-moldability. Therefore, it is useful as a composition for repair and remolding materials.
- the present invention relates to a cured product obtained by curing the crosslinkable resin composition.
- the cured product has a phase separation structure (sea-island structure) formed from a continuous phase (sea portion) and a discontinuous phase (island portion), and the continuous phase (sea portion) is formed from the discontinuous phase (island portion). ), the cured product has a low tensile modulus and forms a phase-separated structure with the progress of curing of the crosslinkable resin composition.
- a cured product having such a structure can exhibit mechanical strength due to the discontinuous phase with a high elastic modulus, and on the other hand, by introducing reversible bonds into the continuous phase with a low elastic modulus, it can be used at low temperatures including room temperature. Also, it has good molecular mobility and flexibility, and even if cracks occur in the cured product, it can exhibit repairability and re-moldability. It can contribute to reduction and is useful.
- the crosslinkable resin composition When curing the crosslinkable resin composition, it may be cured at room temperature or by heating.
- a known or commonly used curing catalyst may be used.
- heat curing When heat curing is performed, it may be cured by heating once, or may be cured through a multi-step heating process.
- the crosslinkable resin composition of the present invention can also be cured with active energy rays.
- a photocationic polymerization initiator may be used as the polymerization initiator. Visible light, ultraviolet rays, X-rays, electron beams, and the like can be used as active energy rays.
- the cured product has a phase separation structure (sea-island structure) formed from a continuous phase (sea portion) and a discontinuous phase (island portion).
- a phase separation structure (sea-island structure) formed from a continuous phase (sea portion) and a discontinuous phase (island portion).
- the ratio of continuous phase (sea portion):discontinuous phase (island portion) is preferably 70:30 to 30:70, more preferably 60:40 to 40:60. Within the above range, the balance between repairability, re-moldability and mechanical strength is excellent and useful.
- the ratio of continuous phase (sea portion):discontinuous phase (island portion) is preferably 60:40 to 10:90, more preferably 50:50 to 10:90.
- the balance between restorability, re-moldability and heat resistance is excellent and useful.
- the ratio of continuous phase (sea portion):discontinuous phase (island portion) is preferably 90:10 to 50:50, more preferably 90:10 to 60. :40.
- the repairability and remolding properties are excellent and useful.
- the content ratio (area fraction (%)) of the continuous phase (sea part) and the discontinuous phase (island part) can be calculated by image processing from the SEM photograph (image analysis type particle size distribution measurement software Mac-View Ver. Area fraction (%) can be calculated from image processing using 4.0.).
- the cured product obtained using the crosslinkable resin composition of the present invention can achieve both heat resistance, flexibility and mechanical strength, and is excellent in repairability and remoldability, so it can be used in various applications. Specifically, it is useful for the following uses.
- the present invention relates to a laminate having a substrate and a layer containing the cured product.
- an inorganic material such as metal or glass, or an organic material such as plastic or wood may be used as appropriate depending on the application. It may have a three-dimensional structure and may be three-dimensional. It may have any shape according to the purpose, such as one having a curvature on the entire surface or a part thereof. Moreover, there are no restrictions on the hardness, thickness, etc. of the base material.
- the cured product of the present invention may be used as a base material, and the cured product of the present invention may be laminated thereon.
- the layer containing the cured product may be formed by direct coating or molding on the substrate, or may be formed by laminating an already molded product.
- the coating method is not particularly limited, and includes a spray method, spin coating method, dipping method, roll coating method, blade coating method, doctor roll method, doctor blade method, curtain coating method, slit coating method, A screen printing method, an inkjet method, and the like can be mentioned.
- Direct molding includes in-mold molding, insert molding, vacuum molding, extrusion lamination molding, press molding, and the like.
- an uncured or semi-cured composition layer may be laminated and then cured, or a cured product layer obtained by completely curing the composition may be laminated on the substrate. good.
- a layer containing the cured product (cured product layer) may be laminated by coating and curing a precursor that can be a base material, or a precursor that can be a base material, or the present invention.
- the crosslinkable resin composition may be adhered in an uncured or semi-cured state and then cured.
- Precursors that can serve as base materials are not particularly limited, and various curable resin compositions and the like are used.
- the cured product obtained using the crosslinkable resin composition of the present invention has particularly high adhesion to metals and/or metal oxides due to the combination of a flexible continuous phase and a mechanically strong discontinuous phase. Therefore, it can be used particularly well as a primer for metals.
- Metals include copper, aluminum, gold, silver, iron, platinum, chromium, nickel, tin, titanium, zinc, various alloys, and composite materials thereof, and metal oxides include single oxides of these metals and / Or a composite oxide is mentioned. In particular, it has excellent adhesion to iron, copper, and aluminum, so it can be used favorably as an adhesive for iron, copper, and aluminum.
- the cured product obtained using the crosslinkable resin composition of the present invention has a flexible continuous phase, stress can be relaxed, so it is particularly preferably used for bonding different materials. It is possible. For example, even when used to bond dissimilar materials such as between metals and non-metals, high adhesiveness can be maintained without being affected by changes in the temperature environment, and peeling or the like is less likely to occur.
- it can be suitably used as an adhesive for structural members in the fields of automobiles, trains, civil engineering and construction, electronics, aircraft, and the space industry.
- the adhesive can also be used as an adhesive for general office, medical, carbon fiber, storage battery cells, modules, and cases.
- mounting adhesives printed wiring board mounting adhesives, die bonding adhesives, semiconductor adhesives such as underfills, BGA reinforcing underfills, anisotropic conductive films, and mounting adhesives such as anisotropic conductive pastes can be used as an agent.
- the crosslinkable resin composition of the present invention contains a fibrous substrate and the fibrous substrate is reinforcing fibers
- the crosslinkable resin composition containing the fibrous substrate can be used as a fiber-reinforced resin.
- the method for incorporating the fibrous substrate into the crosslinkable resin composition is not particularly limited as long as it does not impair the effects of the present invention. Compositing methods such as coating, impregnation, injection, and compression bonding can be mentioned, and can be appropriately selected depending on the form of the fiber and the application of the fiber-reinforced resin.
- the method for molding the fiber-reinforced resin is not particularly limited. If a plate-like product is to be manufactured, extrusion molding is generally used, but flat pressing is also possible. In addition, it is also possible to use extrusion molding, blow molding, compression molding, vacuum molding, injection molding, and the like. In addition, if a film-shaped product is to be produced, a solution casting method can be used in addition to the melt extrusion method. Examples include molding, fiber molding, blow molding, injection molding, rotational molding, coating molding, and the like. Moreover, in the case of a resin that is cured by an active energy ray, a cured product can be produced using various curing methods using an active energy ray.
- thermosetting resin when used as the main component of the matrix resin, there is a molding method in which the molding material is prepregized and pressurized and heated by a press or an autoclave.
- VaRTM Vauum Assist Resin Transfer Molding
- lamination molding hand lay-up molding and the like can be mentioned.
- a cured product obtained using the crosslinkable resin composition of the present invention especially a cured product using an epoxy resin has excellent heat resistance, and can exhibit repairability and re-moldability, so it can be used in large cases and case interiors. It can be used for casting materials, molding materials such as gears and pulleys. These may be cured resins alone or fiber-reinforced cured materials such as glass chips.
- a cured product obtained using the crosslinkable resin composition of the present invention (especially a cured product using an epoxy resin) has excellent heat resistance, flexibility, mechanical strength, and further, repairability and remoldability. It can also be used as materials and electronic materials. In particular, it can be suitably used for semiconductor sealing materials, semiconductor devices, prepregs, printed circuit boards, flexible boards, build-up films, build-up boards, conductive pastes, adhesives, resist materials, and the like. It can also be suitably used as a matrix resin for fiber-reinforced resins, and is particularly suitable as a highly heat-resistant prepreg.
- the cured product obtained using the crosslinkable resin composition can be suitably used for various applications such as heat-resistant members and electronic members.
- parts, aerospace-related parts, electronic/electrical parts, building materials, containers/packaging materials, daily necessities, sports/leisure goods, housing materials for wind power generation, etc. but not limited to these.
- a resin component having excellent heat resistance such as epoxy resin, it is particularly useful as a heat-resistant member.
- the crosslinkable resin composition is added with a curing accelerator, an inorganic filler, and other compounding agents as necessary.
- a method of sufficiently melt-mixing using an extruder, a kneader, a roll, or the like until the mixture becomes uniform is exemplified.
- fused silica is usually used as the inorganic filler, but when it is used as a high thermal conductive semiconductor encapsulant for power transistors and power ICs, crystalline silica, alumina, and nitride, which have higher thermal conductivity than fused silica, are used.
- High filling of silicon or the like, or fused silica, crystalline silica, alumina, silicon nitride, or the like may be used.
- the filling rate is preferably in the range of 30 to 95 parts by mass of the inorganic filler per 100 parts by mass of the crosslinkable resin composition. is more preferably 70 parts by mass or more, and more preferably 80 parts by mass or more.
- the above semiconductor sealing material is cast, or molded using a transfer molding machine, an injection molding machine, etc., and the temperature is set at 50 to 250 ° C. and heating for 2 to 10 hours.
- Prepreg Fiber reinforced resins can form a state called uncured or semi-cured prepreg. After the product is distributed in the prepreg state, final curing may be performed to form a cured product. In the case of forming a laminate, it is preferable to form a prepreg, laminate other layers, and then perform final curing, since a laminate in which each layer adheres can be formed.
- the mass ratio of the composition and the fibrous substrate used at this time is not particularly limited, but it is usually preferable to prepare the prepreg so that the resin content is 20 to 60 mass %.
- the above prepregs are laminated by a conventional method, appropriately overlaid with copper foil, and heated at 170 to 300° C. under a pressure of 1 to 10 MPa. A method of thermocompression bonding for 10 minutes to 3 hours can be used.
- the first step is a step of applying a crosslinkable resin composition containing a resin component, an organic solvent, etc., to an electrically insulating film using a coating machine such as a reverse roll coater or a comma coater. uses a heater to heat an electrically insulating film coated with a crosslinkable resin composition at 60 to 170° C. for 1 to 15 minutes to volatilize the solvent from the electrically insulating film to obtain a crosslinkable resin.
- a coating machine such as a reverse roll coater or a comma coater.
- the third step is to apply heat to the electrically insulating film in which the crosslinkable resin composition has been B-staged, using a heating roll or the like to heat the metal foil as the adhesive. It is a step of crimping (preferably a crimping pressure of 2 to 200 N/cm and a crimping temperature of 40 to 200° C.). If sufficient adhesion performance is obtained by going through the above three steps, it may be finished here, but if complete adhesion performance is required, conditions of 100 to 200 ° C. for 1 to 24 hours are required. is preferably post-cured with.
- the thickness of the resin composition layer after final curing is preferably in the range of 5 to 100 ⁇ m.
- Examples of the method for obtaining a build-up substrate from the crosslinkable resin composition of the present invention include the following steps. First, a step of applying the crosslinkable resin composition properly containing rubber, filler, etc. to a circuit board having a circuit formed thereon by using a spray coating method, a curtain coating method, or the like, and then curing (step 1). After that, after drilling a predetermined through hole portion etc. as necessary, it is treated with a roughening agent, the surface is washed with hot water to form unevenness, and a step of plating a metal such as copper (step 2). Step 3 of alternately building up and forming resin insulating layers and conductor layers having a predetermined circuit pattern by repeating such operations as desired (step 3).
- the through-hole portion is formed after the outermost resin insulation layer is formed.
- the build-up board of the present invention is obtained by heat-pressing a resin-coated copper foil obtained by semi-curing the resin composition on a copper foil onto a wiring board on which a circuit is formed at 170 to 300 ° C. It is also possible to produce a build-up board by omitting the steps of forming a hardened surface and plating.
- the crosslinkable resin composition is applied to the surface of a support film as a substrate, and then heated or blown with hot air. It can be produced by drying the organic solvent to form a layer of the crosslinkable resin composition.
- organic solvent used here examples include ketones such as acetone, methyl ethyl ketone and cyclohexanone, acetic acid esters such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate and carbitol acetate, cellosolve and butyl carbitol.
- ketones such as acetone, methyl ethyl ketone and cyclohexanone
- acetic acid esters such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate and carbitol acetate, cellosolve and butyl carbitol.
- Carbitols, toluene, aromatic hydrocarbons such as xylene, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, etc. are preferably used, and the nonvolatile content
- the thickness of the crosslinkable resin composition layer to be formed is usually greater than or equal to the thickness of the conductor layer. Since the thickness of the conductor layer of the circuit board is usually in the range of 5 to 70 ⁇ m, the thickness of the layer of the crosslinkable resin composition is preferably 10 to 100 ⁇ m.
- the layer of the crosslinkable resin composition may be protected with a protective film, which will be described later. By protecting the surface of the resin composition layer with a protective film, it is possible to prevent the surface of the resin composition layer from being dusted or scratched.
- the support film and protective film described above are polyolefins such as polyethylene, polypropylene, and polyvinyl chloride; Paper patterns and metal foils such as copper foils and aluminum foils can be used.
- the support film and protective film may be subjected to release treatment in addition to mud treatment and corona treatment.
- the thickness of the support film is not particularly limited, it is usually 10 to 150 ⁇ m, preferably 25 to 50 ⁇ m. Also, the thickness of the protective film is preferably 1 to 40 ⁇ m.
- the support film is peeled off after lamination on the circuit board, or after heat curing to form an insulating layer. If the support film is peeled off after the layer of the crosslinkable resin composition that constitutes the build-up film is cured by heating, it is possible to prevent the adhesion of dust and the like during the curing process. When peeling after curing, the support film is normally subjected to a release treatment in advance.
- a multilayer printed circuit board can be manufactured using the build-up film obtained as described above.
- the layer of the crosslinkable resin composition is protected by a protective film, after peeling these off, the layer of the crosslinkable resin composition is applied to one or both sides of the circuit board so as to be in direct contact with the circuit board, for example, vacuum Laminate by lamination method.
- the method of lamination may be a batch type or a continuous roll type. If necessary, the build-up film and the circuit board may be heated (preheated) before lamination.
- the pressure bonding temperature (laminating temperature) is 70 to 140° C., and the pressure bonding pressure is 1 to 11 kgf/cm 2 (9.8 ⁇ 10 4 to 107.9 ⁇ 10 4 N/m 2 ). It is preferable to laminate under a reduced pressure of 20 mmHg (26.7 hPa) or less.
- a method of obtaining a conductive paste from the crosslinkable resin composition of the present invention includes, for example, a method of dispersing conductive particles in the crosslinkable resin composition.
- the conductive paste can be a paste resin composition for circuit connection or an anisotropic conductive adhesive, depending on the type of conductive particles used.
- cured products can also be produced from the crosslinkable resin composition.
- Other cured products can be produced by conforming to a general curing method for a crosslinkable resin composition.
- the heating temperature conditions may be appropriately selected according to the type of curing agent to be combined, the application, and the like.
- GPC "HLC-8320GPC” manufactured by Tosoh Corporation Column: “TSK-GEL G2000HXL” + “TSK-GEL” manufactured by Tosoh Corporation G3000HXL” + “TSK-GEL G4000HXL” Detector: RI (indicative refractometer) Measurement conditions: 40°C Mobile phase: Tetrahydrofuran Flow rate: 1 ml/min Standard: "PStQuick A", “PStQuick B", “PStQuick E”, "PStQuick F” manufactured by Tosoh Corporation
- the epoxy equivalent of the synthesized epoxy resin was measured according to JIS K7236, and the epoxy equivalent (g/eq) was calculated.
- Examples of methods for calculating the number of repeating units include GPC molecular weight measurement and calculation from the results of various appropriate instrumental analyses, such as FD-MS and NMR.
- the hydroxyl equivalent is 2000 g/eq, and the average value of m in the structural formula (b-1) calculated from the hydroxyl equivalent is 6. was 9.
- the average value of m in the following structural formula (A-1) was 8.0. Further, according to the 1 H-NMR spectrum (see FIG.
- the Diels-Alder reaction adduct obtained (10.0 g, 22.9 mmol) was first dissolved in dichloromethane (100 mL) at 0° C., then trifluoroacetic acid (40 mL) was added and stirred for 3 hours while stirring. The solution was allowed to reach room temperature. The mixture was concentrated and washed with diethyl ether four times (30 mL). After evaporating the remaining solvent, the resulting white powder was dissolved in 30 mL of methanol. The methanol solution turned pale yellow after flushing the ion exchange resin several times. The resulting solution was filtered through alkaline alumina and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure at 35° C. to give Diamine DA Adduct Cross-Linker (4.3 g, 80%) as a brown viscous liquid.
- N-(Propyltriethoxysilane)maleimide (TESiM) was obtained according to the synthetic method described in "Nucleosides, Nucleotides and Nucleic Acids" (24, 1076-1077 (2005)). From what was obtained, the structure was confirmed. As a specific synthesis method, N-propyltriethoxysilane was mixed with maleic anhydride in dichloromethane as a solvent to obtain N-(propyltriethoxysilane)maleic acid as an intermediate (reaction time was 1 time). The white crystalline product was then isolated by removing the solvent used.
- N-(propyltriethoxysilane)maleic acid was mixed with zinc chloride and hexametaldisalazane and heated to 80° C. to react, N-(Propyltriethoxysilane)maleimide (TESiM) was obtained.
- the resulting crosslinkable resin composition was sandwiched between aluminum mirror plates (“JIS H 4000 A1050P” manufactured by Engineering Test Service Co., Ltd.) using silicon tubes as spacers, and the curing conditions and A curing reaction was performed under aging conditions to obtain a cured product having a thickness of 4 mm for heat distortion temperature measurement and a cured product having a thickness of 0.8 mm for restorability evaluation.
- aluminum mirror plates (“JIS H 4000 A1050P” manufactured by Engineering Test Service Co., Ltd.) using silicon tubes as spacers
- EPICLON 850S Bisphenol A epoxy resin (manufactured by DIC Corporation, epoxy equivalent 188 g / eq) Furfuryl glycidyl ether: (manufactured by Kanto Kagaku Co., Ltd.)
- EP-001 (main agent) Epoxy/modified silicone-based reaction-induced phase separation type two-component adhesive (manufactured by Cemedine Co., Ltd.), an epoxy resin composition containing bisphenol A type epoxy resin as the main component, and a silicone resin containing a tin compound that is a curing catalyst)
- EP-001 (curing agent) Curing agent (manufactured by Cemedine Co., Ltd.), EP-001 (main agent) (modified silicone resin) compounded with tertiary amine, which is a curing catalyst for epoxy resin DICY: dicyandiamide (Mitsubishi "DICY7" manufactured by Chemical Co., Ltd.)
- DDM diamin
- Example 1 epoxy resin (Ep-1) and Diamine DA Adduct Cross-Linker were mixed in advance at 50°C for 24 hours.
- a schematic diagram of the reaction pathway in Example 1 is shown below.
- Example 2 acrylic polymer (AP-1) and 4-HPM were mixed in advance at 50°C for 24 hours. A schematic diagram of the reaction pathway in Example 2 is shown below.
- Example 3 TESiM and furfuryl glycidyl ether were mixed in advance at 50°C for 24 hours.
- a schematic diagram of the reaction pathway in Example 3 is shown below.
- reaction product of TESiM and furfuryl glycidyl ether has a function corresponding to compound C (containing a reversible bond).
- ⁇ Heat distortion temperature> A cured product of 80 mm x 10 mm x 4 mm thick was used for the measurement. The measurement was carried out flatwise in accordance with JIS K7191-1,2:2015. Specifically, using an HDT test device "Auto-HDT3D-2" (manufactured by Toyo Seiki Seisakusho Co., Ltd.), the distance between fulcrums was 64 mm, the load was 1.80 MPa (high load) and 0.45 MPa (low load), The heat distortion temperature (°C) was measured at a heating rate of 120°C/hour.
- phase separation structure A cross section of the obtained cured product was prepared with an ultramicrotome, and the phase separation structure was observed. A specific observation method was performed using a scanning electron microscope (SEM) (for example, see FIG. 1 of Example 1). By SEM observation, the presence or absence of a phase separation structure in the cured product can be confirmed. If the cured product has a phase separation structure and the structure forms a sea-island structure, the average Particle size ( ⁇ m) was measured. Regarding the average grain size, 50 island portions (discontinuous phase) are arbitrarily extracted from the island portions (discontinuous phase) in the field of view of 200 ⁇ m ⁇ 260 ⁇ m, and the grain size is measured.
- SEM scanning electron microscope
- the diameter was determined (in the case of Example 1, the domain average particle diameter of the island part was 1.2 ⁇ m, and the area fraction of the island part was obtained using image analysis type particle size distribution measurement software Mac-View Ver. 4.0. Therefore, the area fraction (%) can be calculated from the image processing, and the result of the calculation from the image processing was 47%.).
- the conditions for curing the crosslinkable resin composition ranged from room temperature (23 ° C.) to high temperature (160 ° C.), and a cured product having a phase separation structure was obtained. It was confirmed that the heat resistance (heat distortion temperature), mechanical strength (tensile properties), and repair rate are excellent.
- the heat distortion temperature tends to be lower than in Example 1, etc., but in fact, the silicone resin used in Example 3 as a base before the introduction of a reversible bond
- Example 3 the heat distortion temperature was increased, and it was confirmed that the heat resistance was excellent.
- the cured product did not form the desired phase separation structure, and even when a compound corresponding to compound C was used, the function of reversible bonding was not sufficiently exhibited, and heat resistance Either (heat distortion temperature) or mechanical strength (tensile properties) is low, or is so low that it cannot be evaluated, and compared to the examples, heat resistance, mechanical strength, repairability, and remolding I could't find anything that satisfies both sex and sex.
- the cured product obtained using the crosslinkable resin composition of the present invention improves the mechanical strength of the entire cured product due to the discontinuous phase with a high elastic modulus, and the continuous phase with a low elastic modulus improves the mechanical strength of the cured product.
- the inclusion of bonds improves molecular mobility even at low temperatures, including room temperature, and provides flexibility.
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Abstract
Description
前記不連続相が、前記連続相よりも引張弾性率が高く、
前記連続相中に、可逆結合を含有する架橋性樹脂組成物。
前記不連続相が、樹脂成分Bと硬化剤との反応生成物を含み、
前記相分離構造が、前記連続相及び前記不連続相と、前記硬化剤との反応生成物を含む前記〔1〕記載の架橋性樹脂組成物。
前記不連続相が、樹脂成分Bと硬化剤の反応生成物、及び/または、樹脂成分Bの自己重合生成物を含み、
前記連続相中の官能基(a1)が、前記不連続相中の官能基(b1)と反応性を有し、
前記相分離構造が、前記連続相中の官能基(a1)と前記不連続相中の官能基(b1)との反応生成物を含む前記〔1〕又は〔2〕記載の架橋性樹脂組成物。
本発明は、連続相、及び、不連続相から形成される相分離構造を有する硬化物を形成可能な架橋性樹脂組成物であって、
前記不連続相が、前記連続相よりも引張弾性率が高く、
前記連続相中に、可逆結合を含有する架橋性樹脂組成物に関する。
本発明の架橋性樹脂組成物を用いて得られる硬化物は、連続相(海部)、及び、不連続相(島部)から形成される相分離構造を有し、前記連続相(海部)は、前記不連続相(島部)に対して、引張弾性率が低く、前記架橋性樹脂組成物の硬化進行に伴い、相分離構造を形成した硬化物となる。
また、前記架橋性樹脂組成物は、連続相、及び、不連続相から形成される相分離構造を有する硬化物を形成が可能であり、その結果、引張弾性率の高い不連続相により、得られる硬化物全体における機械的強度が向上し、一方で、可逆結合を含有(導入)された連続相は、分子運動性が高く、柔軟性に優れ、室温(23℃)を含む低温領域(例えば、0~100℃)においても、可逆結合により、これらの性能を発揮することができ、硬化物のクラックなどの破損に対して、修復性や再成形性を発揮でき、硬化物自体の長寿命化や、硬化物による廃棄物の削減に貢献でき、有用である。
本発明の架橋性樹脂組成物としては、前記連続相が、前記可逆結合を含有する樹脂成分Aと硬化剤との反応生成物を含み、
前記不連続相が、樹脂成分Bと硬化剤との反応生成物を含み、
前記相分離構造が、前記連続相及び前記不連続相と、前記硬化剤との反応生成物を含むことが好ましい。
上記実施形態においては、樹脂成分Aが硬化剤との反応により、反応生成物(反応生成物A)が得られ、前記反応生成物が、連続相(島部)の基となる構造を形成し、樹脂成分Bと硬化剤との反応により、反応生成物(反応生成物B)が得られ、不連続相(海部)の基となる構造を形成し、更に、両反応生成物が、更に、前記硬化剤とそれぞれ反応(海島界面の反応)することにより、相分離構造(海島構造)を形成することができる。
なお、樹脂成分Aと樹脂成分Bとは、樹脂成分が構造的(官能基濃度の違いなど)に異なるため、硬化剤との反応性が異なり、樹脂成分Aまたは樹脂成分Bのいずれかが、一方の樹脂成分に対して、硬化剤との反応性が高く、反応が進行し易く、得られる硬化物は、相分離構造を形成することができる。
本発明の架橋性樹脂組成物は、前記連続相が、前記可逆結合を含有する樹脂成分Aと硬化剤との反応生成物、及び/または、前記可逆結合を含有する樹脂成分Aの自己重合生成物を含み、
前記不連続相が、樹脂成分Bと硬化剤の反応生成物、及び/または、樹脂成分Bの自己重合生成物を含み、
前記連続相中の官能基(a1)が、前記不連続相中の官能基(b1)と反応性を有し、
前記相分離構造が、前記連続相中の官能基(a1)と前記不連続相中の官能基(b1)との反応生成物を含むことが好ましい。
上記実施形態においては、樹脂成分Aが硬化剤との反応により、反応生成物(反応生成物A)が得られ、もしくは、樹脂成分A単独(硬化促進剤などを使用する場合はある)で自己重合することで、自己重合生成物が得られ、前記反応生成物または自己重合生成物により、連続相(島部)の基となる構造を形成し、
樹脂成分Bが硬化剤との反応により、反応生成物(反応生成物B)が得られ、もしくは、樹脂成分B単独(硬化促進剤などを使用する場合はある)で自己重合することで、自己重合生成物が得られ、前記反応生成物または自己重合生成物により、不連続相(海部)の基となる構造を形成し、
前記連続相中の官能基(a1)が、前記不連続相中の官能基(b1)と反応性を有し、前記連続相中の官能基(a1)と前記不連続相中の官能基(b1)との反応することにより、得られる硬化物は、相分離構造(海島構造)を形成することができる。
なお、樹脂成分Aと樹脂成分Bとは、それぞれの反応性を有する官能基を組み合わせることで、様々な相分離構造に調製することができ、特に制限なく使用できる。例えば、エポキシ基とフェノール性水酸基、エポキシ基とアミノ基、エポキシ基とカルボキシル基、エポキシ基と酸無水物基、エポキシ基とチオール基、マレイミド基と二重結合(エン反応)、チオールと二重結合、イソシアネートとアルコール性水酸基、カルボキシル基とアルコール性水酸基、アミノ基とカルボキシル基、SiH基と二重結合(ヒドロシリル化)などの組合せや、エポキシ基のアニオン重合、エポキシ基のカチオン重合、マレイミドの重合、アクリロイル基の重合、アルコキシシランの加水分解重縮合などが例示できる。これらの中でも、特に耐久性の観点から、エポキシ基とフェノール性水酸基、エポキシ基とアミノ基、及び、エポキシ基のアニオン重合が好ましい。
本発明の架橋性樹脂組成物は、前記連続相が、前記可逆結合を含有する樹脂成分Aと硬化剤との反応生成物を含み、
前記不連続相が、樹脂成分Bと硬化剤との反応生成物を含み、
前記連続相中の官能基(a1)が、前記不連続相中の官能基(b1)と反応性を有し、
前記相分離構造が、前記連続相中の官能基(a1)と前記不連続相中の官能基(b1)との反応生成物を含むことができる。
本発明の架橋性樹脂組成物は、前記連続相が、前記可逆結合を含有する樹脂成分Aの自己重合生成物を含み、
前記不連続相が、樹脂成分Bの自己重合生成物を含み、
前記連続相中の官能基(a1)が、前記不連続相中の官能基(b1)と反応性を有し、
前記相分離構造が、前記連続相中の官能基(a1)と前記不連続相中の官能基(b1)との反応生成物を含むことができる。
本発明の架橋性樹脂組成物は、前記連続相が、前記可逆結合を含有する樹脂成分Aと硬化剤との反応生成物を含み、
前記不連続相が、樹脂成分Bの自己重合生成物を含み、
前記連続相中の官能基(a1)が、前記不連続相中の官能基(b1)と反応性を有し、
前記相分離構造が、前記連続相中の官能基(a1)と前記不連続相中の官能基(b1)との反応生成物を含むことができる。
本発明の架橋性樹脂組成物は、前記連続相が、前記可逆結合を含有する樹脂成分Aの自己重合生成物を含み、
前記不連続相が、樹脂成分Bと硬化剤との反応生成物を含み、
前記連続相中の官能基(a1)が、前記不連続相中の官能基(b1)と反応性を有し、
前記相分離構造が、前記連続相中の官能基(a1)と前記不連続相中の官能基(b1)との反応生成物を含むことができる。
(以下、「モノマー成分等」と称する場合がある。)と、前記モノマー成分等と反応性を有し、かつ、可逆結合を形成可能な化合物(以下、「化合物C」と称する場合がある。)を反応させることで、樹脂成分A中に可逆結合を含有(導入)することができ、ひいては、連続相中に可逆結合を含有(導入)することができる。
前記化合物Cとしては、単独もしくは複数の化合物を使用することができる。
また、前記樹脂成分A中に、可逆結合を含有(導入)する方法として、モノマー成分等と共に、モノマー成分等とは別の複数の化合物(例えば、「化合物C’」と「化合物C’’」)を反応させることで、前記別の複数の化合物に起因して、樹脂成分A中に可逆結合を形成する場合も含むものである。
なお、可逆結合については、樹脂成分Aがポリマーの場合は、その側鎖や主鎖のいずれに形成されていてもよく、柔軟性の観点から、側鎖に形成されていることがより好ましく、耐熱性の観点から、主鎖に形成されていることがより好ましい。また、樹脂成分Aの構造が同一あるいは類似の場合は、修復性の観点からは、側鎖に形成されていることがより好ましく、再成形の観点からは、主鎖に形成されていることがより好ましい。
前記連続相を形成し得る樹脂成分(または樹脂組成物)A、及び、前記不連続相を形成し得る樹脂成分(又は樹脂組成物)Bに関しては、それぞれの樹脂成分(又は樹脂組成物)の硬化物の引張弾性率の差や、前記連続相中に導入される可逆結合に起因する化合物Cや、前記モノマー成分等と前記化合物C’、前記化合物C”との反応性の違い等により、適宜選択することができる。
前記架橋性樹脂組成物にエポキシ樹脂を使用することで、耐熱性、機械的強度、接着強度、電気絶縁性に優れる硬化物が得られ、有用となる。なお、前記エポキシ樹脂を調製する方法としては、公知・慣用の方法を採用することができる。
また、前記エポキシ樹脂を含有する架橋性樹脂組成物を半導体封止材料用途やプリント回路基板、ビルドアップ基板などの電子材料として使用する場合には、硬化性、耐熱性、電気特性、耐湿信頼性等に優れる点から、リン系化合物ではトリフェニルホスフィン、第3級アミンではジメチルアミノピリジンやイミダゾール類、1,8-ジアザビシクロ-[5.4.0]-ウンデセン(DBU)、ベンジルジメチルアミンが好ましい。
前記架橋性樹脂組成物にアクリル系樹脂(アクリル系ポリマー)等を使用することで、速硬化性が付与でき、柔軟性に優れた硬化物が得られ、有用となる。なお、前記アクリル系樹脂等を調製する方法としては、公知・慣用の方法を採用することができ、例えば、モノマーのみを使用する場合や、事前に、モノマーを重合したポリマーと、モノマーと併用する場合、事前にポリマー化したものを用いる場合などが例示できる。
(メタ)アクリル酸メチル、(メタ)アクリル酸エチル、(メタ)アクリル酸プロピル、(メタ)アクリル酸-n-ブチル、(メタ)アクリル酸-t-ブチル、(メタ)アクリル酸ヘキシル、(メタ)アクリル酸ヘプシル、(メタ)アクリル酸オクチル、(メタ)アクリル酸ノニル、(メタ)アクリル酸デシル、(メタ)アクリル酸ドデシル、(メタ)アクリル酸テトラデシル、(メタ)アクリル酸ヘキサデシル、(メタ)アクリル酸ステアリル、(メタ)アクリル酸オクタデシル、(メタ)アクリル酸ドコシル等の炭素数1~22のアルキル基を持つ(メタ)アクリル酸エステル;
(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸イソボロニル、(メタ)アクリル酸ジシクロペンタニル、(メタ)アクリル酸ジシクロペンテニルオキシエチル等の脂環式のアルキル基を有する(メタ)アクリル酸エステル;
(メタ)アクリル酸ベンゾイルオキシエチル、(メタ)アクリル酸ベンジル、(メタ)アクリル酸フェニルエチル、(メタ)アクリル酸フェノキシエチル、(メタ)アクリル酸フェノキシジエチレングリコール、(メタ)アクリル酸2-ヒドロキシ-3-フェノキシプロピル等の芳香環を有する(メタ)アクリル酸エステル;
(メタ)アクリル酸ヒドロキエチル;
(メタ)アクリル酸ヒドロキシプロピル、(メタ)アクリル酸ヒドロキシブチル、(メタ)アクリル酸グリセロール;ラクトン変性(メタ)アクリル酸ヒドロキシエチル、(メタ)アクリル酸ポリエチレングリコール、(メタ)アクリル酸ポリプロピレングリコールなどのポリアルキレングリコール基を有する(メタ)アクリル酸エステル等のヒドロキシアルキル基を有するアクリル酸エステル;
フマル酸ジメチル、フマル酸ジエチル、フマル酸ジブチル、イタコン酸ジメチル、イタコン酸ジブチル、フマル酸メチルエチル、フマル酸メチルブチル、イタコン酸メチルエチルなどの不飽和ジカルボン酸エステル;
スチレン、α-メチルスチレン、クロロスチレンなどのスチレン誘導体;
ブタジエン、イソプレン、ピペリレン、ジメチルブタジエンなどのジエン系化合物;
塩化ビニル、臭化ビニルなどのハロゲン化ビニルやハロゲン化ビニリデン;
メチルビニルケトン、ブチルビニルケトンなどの不飽和ケトン;
酢酸ビニル、酪酸ビニルなどのビニルエステル;
メチルビニルエーテル、ブチルビニルエーテルなどのビニルエーテル;
アクリロニトリル、メタクリロニトリル、シアン化ビニリデンなどのシアン化ビニル;アクリルアミドやそのアルキド置換アミド;
N-フェニルマレイミド、N-シクロヘキシルマレイミドなどのN-置換マレイミド;
フッ化ビニル、フッ化ビニリデン、トリフルオロエチレン、クロロトリフルオロエチレン、ブロモトリフルオロエチレン、ペンタフルオロプロピレンもしくはヘキサフルオロプロピレンの如きフッ素含有α-オレフィン;
トリフルオロメチルトリフルオロビニルエーテル、ペンタフルオロエチルトリフルオロビニルエーテルもしくはヘプタフルオロプロピルトリフルオロビニルエーテルの如き(パー)フルオロアルキル基の炭素数が1から18の範囲である(パー)フルオロアルキル・パーフルオロビニルエーテル;
2,2,2-トリフルオロエチル(メタ)アクリレート、2,2,3,3-テトラフルオロプロピル(メタ)アクリレート、1H,1H,5H-オクタフルオロペンチル(メタ)アクリレート、1H,1H,2H,2H-ヘプタデカフルオロデシル(メタ)アクリレートもしくはパーフルオロエチルオキシエチル(メタ)アクリレートの如き(パー)フルオロアルキル基の炭素数が1から18の範囲である(パー)フルオロアルキル(メタ)アクリレート;
3-メタクリロキシプロピルトリメトキシシラン等のシリル基含有(メタ)アクリレート;
N,N-ジメチルアミノエチル(メタ)アクリレート、N,N-ジエチルアミノエチル(メタ)アクリレートもしくはN,N-ジエチルアミノプロピル(メタ)アクリレート等のN,N-ジアルキルアミノアルキル(メタ)アクリレートなどが挙げられる。
(メタ)アクリル酸、(アクリロイルオキシ)酢酸、アクリル酸2-カルボキシエチル、アクリル酸3-カルボキシプロピル、コハク酸1-[2-(アクリロイルオキシ)エチル]、フタル酸1-(2-アクリロイルオキシエチル)、ヘキサヒドロフタル酸水素2-(アクリロイルオキシ)エチル及びこれらのラクトン変性物等の不飽和モノカルボン酸; マレイン酸等の不飽和ジカルボン酸;
無水コハク酸や無水マレイン酸等の酸無水酸と、ペンタエリスリトールトリアクリレート等の水酸基含有多官能(メタ)アクリレートモノマーとを反応させて得られるカルボキシル基含有多官能(メタ)アクリレート等;
2-アクリロイルオキシエチルイソシアネート、2-メタクリロイルオキシエチルイソシアネート、1,1-ビス(アクリロイルオキシメチル)エチルイソシアネート;
2-ヒドロキシエチルアクリレート、2-ヒドロキシプロピルアクリレート、4-ヒドロキシブチルアクリレート、グリセリンジアクリレート、トリメチロールプロパンジアクリレート、ペンタエリスリトールトリアクリレート、ジペンタエリスリトールペンタアクリレート等の脂肪族(メタ)アクリレート化合物;
アクリル酸4-ヒドロキシフェニル、アクリル酸β-ヒドロキシフェネチル、アクリル酸4-ヒドロキシフェネチル、アクリル酸1-フェニル-2-ヒドロキシエチル、アクリル酸3-ヒドロキシ-4-アセチルフェニル、2-ヒドロキシ-3-フェノキシプロピルアクリレート等;
(メタ)アクリル酸、(アクリロイルオキシ)酢酸、アクリル酸2-カルボキシエチル、アクリル酸3-カルボキシプロピル、コハク酸1-[2-(アクリロイルオキシ)エチル]、フタル酸1-(2-アクリロイルオキシエチル)、ヘキサヒドロフタル酸水素2-(アクリロイルオキシ)エチル及びこれらのラクトン変性物等の不飽和モノカルボン酸; マレイン酸等の不飽和ジカルボン酸;無水コハク酸や無水マレイン酸等の酸無水酸と、ペンタエリスリトールトリアクリレート等の水酸基含有多官能(メタ)アクリレートモノマーとを反応させて得られるカルボキシル基含有多官能(メタ)アクリレート;
(メタ)アクリル酸グリシジル、α-エチル(メタ)アクリル酸グリシジル、α-n-プロピル(メタ)アクリル酸グリシジル、α-n-ブチル(メタ)アクリル酸グリシジル、(メタ)アクリル酸-3,4-エポキシブチル、(メタ)アクリル酸-4,5-エポキシペンチル、(メタ)アクリル酸-6,7-エポキシペンチル、α-エチル(メタ)アクリル酸-6,7-エポキシペンチル、β-メチルグリシジル(メタ)アクリレート、(メタ)アクリル酸-3,4-エポキシシクロヘキシル、ラクトン変性(メタ)アクリル酸-3,4-エポキシシクロヘキシル、ビニルシクロヘキセンオキシド等;
2-ヒドロキシエチルアクリレート、2-ヒドロキシプロピルアクリレート、4-ヒドロキシブチルアクリレート、2,3-ジヒドロキシプロピルアクリレート、2-ヒドロキシエチルメタクリレート、2-ヒドロキシプロピルメタクリレート、4-ヒドロキシブチルメタクリレート、2,3-ジヒドロキシプロピルメタクリレート等;
(メタ)アクリレートとしては、例えば、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、2-ヒドロキシブチル(メタ)アクリレート、n-ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、t-ブチル(メタ)アクリレート、グリシジル(メタ)アクリレート、アクリロイルモルフォリン、N-ビニルピロリドン、テトラヒドロフルフリールアクリレート、シクロヘキシル(メタ)アクリレート、2-エチルヘキシル(メタ)アクリレート、イソボルニル(メタ)アクリレート、イソデシル(メタ)アクリレート、ラウリル(メタ)アクリレート、トリデシル(メタ)アクリレート、セチル(メタ)アクリレート、ステアリル(メタ)アクリレート、ベンジル(メタ)アクリレート、2-エトキシエチル(メタ)アクリレート、3-メトキシブチル(メタ)アクリレート、エチルカルビトール(メタ)アクリレート、リン酸(メタ)アクリレート、エチレンオキサイド変性リン酸(メタ)アクリレート、フェノキシ(メタ)アクリレート、エチレンオキサイド変性フェノキシ(メタ)アクリレート、プロピレンオキサイド変性フェノキシ(メタ)アクリレート、ノニルフェノール(メタ)アクリレート、エチレンオキサイド変性ノニルフェノール(メタ)アクリレート、プロピレンオキサイド変性ノニルフェノール(メタ)アクリレート、メトキシジエチレングリコール(メタ)アクリレート、メトキシポリチレングリコール(メタ)アクリレート、メトキシプロピレングリコール(メタ)アクリレート、2-(メタ)アクリロイルオキシエチル-2-ヒドロキシプロピルフタレート、2-ヒドロキシ-3-フェノキシプロピル(メタ)アクリレート、2-(メタ)アクリロイルオキシエチルハイドロゲンフタレート、2-(メタ)アクリロイルオキシプロピルハイドロゲンフタレート、2-(メタ)アクリロイルオキシプロピルヘキサヒドロハイドロゲンフタレート、2-(メタ)アクリロイルオキシプロピルテトラヒドロハイドロゲンフタレート、ジメチルアミノエチル(メタ)アクリレート、トリフルオロエチル(メタ)アクリレート、テトラフルオロプロピル(メタ)アクリレート、ヘキサフルオロプロピル(メタ)アクリレート、オクタフルオロプロピル(メタ)アクリレート、オクタフルオロプロピル(メタ)アクリレート、アダマンチルモノ(メタ)アクリレート等の単官能(メタ)アクリレート単量体等;を挙げることができる。
前記架橋剤としては、種々のものが使用できるが、例えば、イソシアネート系架橋剤、カルボジイミド系架橋剤、エポキシ系架橋剤、メラミン系架橋剤、過酸化物系架橋剤、尿素系架橋剤、金属アルコキシド系架橋剤、金属キレート系架橋剤、金属塩系架橋剤、オキサゾリン系架橋剤、アジリジン系架橋剤、および、アミン系架橋剤等が挙げられる。これら架橋剤は、1種を単独でまたは2種以上を組み合わせて使用することができる。また、架橋剤の含有量は、目的とする架橋度に応じて適切に設定することができ、特定の範囲に限定されない。
前記架橋性樹脂組成物にシリコーン系樹脂を使用することで、柔軟性やシール性に優れる硬化物となり、有用となる。なお、前記シリコーン系樹脂を調製する方法としては、公知・慣用の方法を採用することができる。
(1)で表されるアルコキシ基を有するシラン化合物を用いることができる。
Si(OR1)nR2 4-n (1)
上記式(1)中、nは2、3または4を示し、R1はアルキル基を示し、R2は有機基を示す。
なお、(メタ)アクリロキシトリアルコキシシランは、アクリロキシトリアルコキシシランまたはメタクリロキシトリアルコキシシランであることを意味する。(メタ)アクリレート基、(メタ)アクリロキシアルキル基についても同様である。
上記式(2)で表される化合物は、例えば、両末端にシラノール基を有するポリシロキサンを、テトラメトキシシランで変性することによって製造することができる。
前記樹脂成分A、及び、前記樹脂成分Bとしては、エポキシ樹脂やアクリル系樹脂等、シリコーン系樹脂などに加えて、本発明の架橋性樹脂組成物を用いて得られる硬化物の特性を損なわない範囲であれば、その他の樹脂を使用することができる。前記その他の樹脂としては、例えば、前記樹脂成分Aまたは樹脂成分Bにエポキシ樹脂を使用する場合には、低温域では、前記エポキシ樹脂と相互に溶け合って一相溶液となり、一方、高温域では、溶け合わないことが知られているポリエーテルスルホンなどの熱可塑性樹脂や、両末端にカルボキシル基やアミノ基を持ち、エポキシ基と反応することができる液状ニトリルゴム(CTBNやATBNなど)が挙げられる。
前記連続相中に、可逆結合を含有(導入)するため、例えば、前記樹脂成分A中に、可逆結合を含有(導入)することが好ましく、前記可逆結合に起因する化合物Cや、化合物Cとは別に、複数の化合物として、例えば、化合物C’と化合物C’’を反応させることで、前記樹脂成分A中に可逆結合を含有(導入)することができ、ひいては、連続相中に可逆結合を含有(導入)することができる。
前記化合物Cを用いて、前記樹脂成分A中に可逆結合を含有(導入)する方法としては、前記化合物Cは、その構造(骨格)中に既に可逆結合を含有する化合物であり、樹脂成分Aと反応することで、直接的に、樹脂成分Aの構造(骨格)中に、化合物Cに起因する可逆結合が導入されるものである。
また、前記化合物C’と前記化合物C’’を反応させることで、前記樹脂成分A中に可逆結合を含有(導入)する方法としては、例えば、前記モノマー成分等と共に、前記化合物C’と前記化合物C’’を混合し、反応させることで、前記化合物C’と前記化合物C’’の反応性を有する官能基同士が反応することで、間接的に、前記モノマー成分等から形成される樹脂成分Aの構造(骨格)中に、前記化合物C’と前記化合物C’’との反応により生成される可逆結合が導入されるものである。例えば、前記モノマー成分等と、前記化合物C’が反応(結合)した状態(前駆体形成)に対して、前記化合物C’’の反応性の官能基が、前記前駆体中の反応性の官能基と反応することで、前記樹脂成分A中に可逆結合を含有(導入)する場合が挙げられる。
また、本発明の架橋性樹脂組成物が、上記もしくは下記の併用可能な他の樹脂を含む場合は、本発明の架橋性樹脂組成物中における可逆結合のモル濃度は、樹脂成分A、樹脂成分B、及び、化合物C(化合物C’と前記化合物C’’の合計)に加えて、前記併用可能な樹脂との合計した質量(g数)に対して、好ましくは、0.10mmol/g以上であり、より好ましくは0.10~3.00mmol/gであり、更に好ましくは0.15~2.00mmol/gである。前記可逆結合のモル濃度は以下の式により算出できる。なお、可逆結合のモル数は、理論モル数である。
(可逆結合のモル濃度)(mmol/g)=(可逆結合のモル数)/(樹脂成分A+樹脂成分B+化合物C(または、化合物C’+前記化合物C’’の合計g数))の合計g数)
本発明の架橋性樹脂組成物は、更に充填剤を含有してもよい。充填剤としては、無機充填剤と有機充填剤が挙げられる。無機充填剤としては、例えば、無機微粒子が挙げられる。
これらの無機微粒子は、用途によって適時選択すればよく、単独で使用しても、複数種組み合わせて使用してもかまわない。また、上記無機微粒子は、例に挙げた特性以外にも様々な特性を有することから、適時用途に合わせて選択すればよい。
(株)製シルデックスH31、H32、H51、H52、H121、H122、日本シリカ工業(株)製E220A、E220、富士シリシア(株)製SYLYSIA470、日本板硝子(株)製SGフレ-ク等を挙げることができる。また、市販のコロイダルシリカとしては、例えば、日産化学工業(株)製メタノ-ルシリカゾル、IPA-ST、MEK-ST、NBA-ST、XBA-ST、DMAC-ST、ST-UP、ST-OUP、ST-20、ST-40、ST-C、ST-N、ST-O、ST-50、ST-OL等を挙げることができる。
本発明の架橋性樹脂組成物は、更に繊維質基質を含有してもよい。本発明の繊維質基質は、特に限定はないが、繊維強化樹脂に用いられるものが好ましく、無機繊維や有機繊維が挙げられる。
本発明の架橋性樹脂組成物は、架橋性樹脂組成物の固形分量や粘度を調整する目的として、分散媒を使用してもよい。分散媒としては、本発明の効果を損ねることのない液状媒体であればよく、各種有機溶剤、液状有機ポリマー等が挙げられる。
本発明の架橋性樹脂組成物は、上述した各種樹脂や化合物以外の樹脂を含有していてもよい。このような樹脂としては、本発明の効果を損なわない範囲であれば公知・慣用の樹脂を配合すればよく、例えば、熱硬化性樹脂や熱可塑性樹脂を用いることができる。
本発明の架橋性樹脂組成物は、その他の配合物を含有していてもよい。例えば、上述したもの以外の触媒、重合開始剤、無機顔料、有機顔料、体質顔料、粘土鉱物、ワックス、界面活性剤、安定剤、流動調整剤、カップリング剤、染料、レベリング剤、レオロジーコントロール剤、紫外線吸収剤、酸化防止剤、難燃剤、可塑剤、反応性希釈剤等が挙げられる。
本発明は、前記架橋性樹脂組成物を硬化してなる硬化物に関する。前記硬化物は、連続相(海部)、及び、不連続相(島部)から形成される相分離構造(海島構造)を有し、前記連続相(海部)は、前記不連続相(島部)に対して、引張弾性率が低く、前記架橋性樹脂組成物の硬化進行に伴い、相分離構造を形成した硬化物であることを特徴とする。このような構造を有する硬化物は、高弾性率の不連続相により機械的強度を発現でき、一方で、低弾性率の連続相に可逆結合が導入されることで、室温を含む低温領域においても、分子運動性が良好となり、柔軟性が付与され、硬化物にクラックなどが発生した場合であっても、修復性や再成形性を発揮でき、硬化物自体の長寿命化や廃棄物の削減に貢献でき、有用である。
また、耐熱性の観点から、好ましくは、連続相(海部):不連続相(島部)が、60:40~10:90であり、より好ましくは、50:50~10:90である。前記範囲内であると、修復性や再成形性と耐熱性のバランスに優れ、有用である。
また、修復性や再成形性を優先する観点から、好ましくは、連続相(海部):不連続相
(島部)=90:10~50:50であり、より好ましくは、90:10~60:40である。前記範囲内であると、修復性や再成形性に優れ、有用である。
なお、前記範囲内に調製する方法としては、樹脂成分Aと樹脂成分Bの及び化合物Cの配合割合の調整や、樹脂成分Aと樹脂成分Bの硬化速度差の調整、樹脂成分Aと樹脂成分Bの粘度差の調整、樹脂成分Aと樹脂成分Bの相溶性の調整、その他、一般的に相分離構造の調整に用いられる諸条件の、硬化温度の変更、樹脂成分の配合順序、触媒種の選定、結晶性物質の活用や結晶化速度差などの活用などが挙げられる。
なお、連続相(海部)と不連続相(島部)の含有割合(面積分率(%))は、SEM写真からの画像処理により算出できる(画像解析式粒度分布測定ソフトウェアMac-View Ver.4.0を用いて画像処理から、面積分率(%)を算出可能である。)。
本発明の架橋性樹脂組成物を用いて得られる硬化物は、耐熱性、柔軟性及び機械的強度を両立でき、更に、修復性及び再成形性に優れるため、様々な用途に使用でき、具体的には、以下に示す用途に有用である。
本発明は、基材と、前記硬化物を含む層と、を有する積層体に関する。前記積層体の基材としては、金属やガラス等の無機材料や、プラスチックや木材といった有機材料等、用途によって適時使用すればよく、積層体の形状であってもよく、平板、シート状、あるいは三次元構造を有していてもよく、立体状であってもよい。全面にまたは一部に曲率を有するもの等、目的に応じた任意の形状であってもよい。また、基材の硬度、厚み等にも制限はない。また、本発明の硬化物を基材とし、更に本発明の硬化物を積層してもよい。
本発明の架橋性樹脂組成物を用いて得られる硬化物は、金属及び/または金属酸化物に対する接着性が、柔軟性に富む連続相と機械的強度の高い非連続相の組み合わせにより、特に高いため、金属用のプライマーとして特に良好に使用可能である。金属としては銅、アルミ、金、銀、鉄、プラチナ、クロム、ニッケル、錫、チタン、亜鉛、各種合金、及びこれらを複合した材料が挙げられ、金属酸化物としてはこれら金属の単独酸化物及び/または複合酸化物が挙げられる。特に鉄、銅、アルミに対しての接着力に優れるため、鉄、銅、アルミ用の接着剤として良好に使用可能である。
また、本発明の架橋性樹脂組成物を用いて得られる硬化物は、柔軟性に富む連続相を有していることより、応力を緩和することができることから、特に異種素材の接着に好ましく利用可能である。例えば、金属-非金属間のような異種素材の接着に用いた場合にも、温度環境の変化に影響されず高い接着性を維持することができ、剥がれ等が生じ難い。具体的な用途としては、自動車、電車、土木建築、エレクトロニクス、航空機、宇宙産業分野の構造部材の接着剤として好適に用いることができる。また、前記接着剤は、構造部材用途の他、一般事務用、医療用、炭素繊維、蓄電池のセルやモジュールやケース用などの接着剤としても使用でき、光学部品接合用接着剤、光ディスク貼り合わせ用接着剤、プリント配線板実装用接着剤、ダイボンディング接着剤、アンダーフィルなどの半導体用接着剤、BGA補強用アンダーフィル、異方性導電性フィルム、異方性導電性ペーストなどの実装用接着剤として使用することができる。
本発明の架橋性樹脂組成物が繊維質基質を含有し、前記繊維質基質が強化繊維の場合、繊維質基質を含有する架橋性樹脂組成物は、繊維強化樹脂として用いることができる。前記架橋性樹脂組成物に、前記繊維質基質を含有させる方法としては、本発明の効果を損なわない範囲であれば、特に限定されず、繊維質基質と架橋性樹脂組成物とを、混練、塗布、含浸、注入、圧着等の方法で複合化する方法が挙げられ、繊維の形態及び繊維強化樹脂の用途によって、適時選択することができる。
本発明の架橋性樹脂組成物を用いて得られる硬化物として、特にエポキシ樹脂を用いた硬化物は、耐熱性に優れ、更に、修復性や再成形性を発揮できるため、大型ケースやケース内部の注型材、ギアやプーリー等の成形材料に使用することができる。これらは樹脂単独の硬化物でも良く、ガラスチップなどの繊維強化された硬化物でも良い。
本発明の架橋性樹脂組成物を用いて得られる硬化物(特にエポキシ樹脂を用いた硬化物)が、耐熱性や柔軟性、機械的強度、更に、修復性や再成形性に優れるため、耐熱材料及び電子材料としても使用可能である。特に、半導体封止材料、半導体装置、プリプレグ、プリント回路基板、フレキシブル基板、ビルドアップフィルム、ビルドアップ基板、導電性ペースト、接着剤やレジスト材料等に好適に使用可能である。また、繊維強化樹脂のマトリクス樹脂にも好適に使用可能であり、高耐熱性のプリプレグとして特に適している。
また、前記架橋性樹脂組成物を用いて得られる硬化物は、耐熱部材や電子部材として、各種用途に好適に使用可能であり、例えば、産業用機械部品、一般機械部品、自動車・鉄道・車両等部品、宇宙・航空関連部品、電子・電気部品、建築材料、容器・包装部材、生活用品、スポーツ・レジャー用品、風力発電用筐体部材等が挙げられ、特にこれらに限定されるものではないが、エポキシ樹脂などの耐熱性に優れる樹脂成分を使用する際には、耐熱部材として、特に有用である。
本発明の架橋性樹脂組成物からから半導体封止材料を得る方法としては、前記架橋性樹脂組成物に、硬化促進剤、及び無機充填剤等の配合剤とを必要に応じて押出機、ニ-ダ、ロ-ル等を用いて均一になるまで充分に溶融混合する方法が挙げられる。その際、無機充填剤としては、通常、溶融シリカが用いられるが、パワートランジスタ、パワーIC用高熱伝導半導体封止材として用いる場合は、溶融シリカよりも熱伝導率の高い結晶シリカ、アルミナ、窒化ケイ素などの高充填化、又は溶融シリカ、結晶性シリカ、アルミナ、窒化ケイ素などを用いるとよい。その充填率は架橋性樹脂組成物100質量部当たり、無機充填剤を30~95質量部の範囲で用いることが好ましく、中でも、難燃性や耐湿性や耐ハンダクラック性の向上、線膨張係数の低下を図るためには、70質量部以上がより好ましく、80質量部以上であることがさらに好ましい。
本発明の架橋性樹脂組成物から半導体装置を得る半導体パッケージ成形としては、上記半導体封止材料を注型、或いはトランスファー成形機、射出成形機などを用いて成形し、さらに50~250℃で、2~10時間の間、加熱する方法が挙げられる。
繊維強化樹脂は、未硬化あるいは半硬化のプリプレグと呼ばれる状態を形成することができる。プリプレグの状態で製品を流通させた後、最終硬化をおこなって硬化物を形成してもよい。積層体を形成する場合は、プリプレグを形成した後、その他の層を積層してから最終硬化を行うことで、各層が密着した積層体を形成できるため、好ましい。このとき用いる組成物と繊維質基質の質量割合としては、特に限定されないが、通常、プリプレグ中の樹脂分が20~60質量%となるように調製することが好ましい。
本発明の架橋性樹脂組成物からプリント配線基板を得る方法としては、上記プリプレグを、常法により積層し、適宜銅箔を重ねて、1~10MPaの加圧下に170~300℃で10分~3時間、加熱圧着させる方法が挙げられる。
本発明の架橋性樹脂組成物からフレキシルブル基板を製造する方法としては、以下に示す3つの工程からなる方法で製造されるものが挙げられる。第1の工程は、樹脂成分や有機溶剤等を配合した架橋性樹脂組成物を、リバースロールコータ、コンマコータ等の塗布機を用いて、電気絶縁性フィルムに塗布する工程であり、第2の工程は、加熱機を用いて60~170℃で1~15分間の間、架橋性樹脂組成物が塗布された電気絶縁性フィルムを加熱し、電気絶縁性フィルムから溶剤を揮発させて、架橋性樹脂組成物をB-ステージ化する工程であり、第3の工程は、架橋性樹脂組成物がB-ステージ化された電気絶縁性フィルムに、加熱ロール等を用いて、接着剤に金属箔を熱圧着(圧着圧力は2~200N/cm、圧着温度は40~200℃が好ましい)する工程である。なお、上記3つの工程を経ることで、十分な接着性能が得られれば、ここで終えても構わないが、完全接着性能が必要な場合は、さらに100~200℃で1~24時間の条件で後硬化させることが好ましい。最終的に硬化させた後の樹脂組成物層の厚みは、5~100μmの範囲が好ましい。
本発明の架橋性樹脂組成物からビルドアップ基板を得る方法としては、例えば、以下の工程が挙げられる。まず、ゴム、充填剤などを適宜配合した前記架橋性樹脂組成物を、回路を形成した回路基板にスプレーコーティング法、カーテンコーティング法等を用いて塗布した後、硬化させる工程(工程1)。その後、必要に応じて所定のスルーホール部等の穴あけを行った後、粗化剤により処理し、その表面を湯洗することによって凹凸を形成させ、銅などの金属をめっき処理する工程(工程2)。このような操作を所望に応じて順次繰り返し、樹脂絶縁層及び所定の回路パターンの導体層を交互にビルドアップして形成する工程(工程3)。なお、スルーホール部の穴あけは、最外層の樹脂絶縁層の形成後に行う。また、本発明のビルドアップ基板は、銅箔上で当該樹脂組成物を半硬化させた樹脂付き銅箔を、回路を形成した配線基板上に、170~300℃で加熱圧着することで、粗化面を形成、メッキ処理の工程を省き、ビルドアップ基板を作製することも可能である。
本発明の架橋性樹脂組成物からビルドアップフィルムを得る方法としては、基材である支持フィルムの表面に、前記架橋性樹脂組成物を塗布し、更に加熱、あるいは熱風吹きつけ等により有機溶剤を乾燥させて架橋性樹脂組成物の層を形成させることにより製造することができる。
本発明の架橋性樹脂組成物から導電性ペーストを得る方法としては、例えば、導電性粒子を前記架橋性樹脂組成物中に分散させる方法が挙げられる。前記導電性ペーストは、用いる導電性粒子の種類によって、回路接続用ペースト樹脂組成物や異方性導電接着剤とすることができる。
上記で半導体封止材料等を製造する方法について説明したが、架橋性樹脂組成物からその他の硬化物を製造することもできる。その他の硬化物の製造方法としては、一般的な架橋性樹脂組成物の硬化方法に準拠することにより製造することができる。例えば加熱温度条件は、組み合わせる硬化剤の種類や用途等によって、適宜選択すればよい。
磁場強度:600MHz
積算回数:32回
溶媒:DMSO-d6
試料濃度:30質量%
測定範囲:m/z=50.00~2000.00
変化率:25.6mA/min
最終電流値:40mA
カソード電圧:-10kV
カラム:東ソー株式会社製「TSK-GEL G2000HXL」+「TSK-GEL
G3000HXL」+「TSK-GEL G4000HXL」
検出器:RI(示唆屈折率計)
測定条件:40℃
移動相:テトラヒドロフラン
流速:1ml/min
標準:東ソー株式会社製「PStQuick A」、「PStQuick B」、「PStQuick E」、「PStQuick F」
温度計、撹拌機を取り付けたフラスコに1,12-ドデカンジオールのジグリシジルエーテル(四日市合成株式会社製:エポキシ当量210g/eq)210g(0.5モル)とビスフェノールA(水酸基当量114g/eq)119.7g(0.53モル)を仕込み、140℃まで30分間要して昇温した後、20%水酸化ナトリウム水溶液3.2gを仕込んだ。その後、30分間を要して150℃まで昇温し、さらに150℃で16時間反応させた。その後、中和量のリン酸ソーダを添加し、ヒドロキシ化合物(Ph-1)を320g得た。
前記ヒドロキシ化合物(Ph-1)は、マススペクトル(FD-MSスペクトル)で測定し、下記構造式(b-1)で示され、下記構造式(b-1)中のm=1、n=12の理論構造に相当するM+=771のピークが得られたことから、構造式(b-1)で表される構造のヒドロキシ化合物を含有することが確認された。
前記ヒドロキシ化合物(Ph-1)の1H-NMR、および、GPCにより算出し、水酸基当量は2000g/eq、水酸基当量から算出した前記構造式(b-1)中のmの平均値は6.9であった。
温度計、滴下ロート、冷却管,撹拌機を取り付けたフラスコに、窒素ガスパージを施しながら、合成例1で得られたヒドロキシ化合物(Ph-1)を200g,エピクロルヒドリン437g(4.72モル)、n-ブタノール118gを仕込み溶解させた。65℃に昇温した後、共沸する圧力まで減圧して、49%水酸化ナトリウム水溶液6.66g(0.08モル)を5時間かけて滴下した。その後、同条件で0.5時間撹拌を続けた。この間、共沸によって留出してきた留出分をディーンスタークトラップで分離し、水層を除去し、油層を反応系内に戻しながら、反応を行った。その後、未反応のエピクロルヒドリンを減圧蒸留によって留去させた。それで得られた粗エポキシ樹脂にメチルイソブチルケトン150gとn-ブタノール150gとを加え溶解した。更に、この溶液に10%水酸化ナトリウム水溶液10gを添加して80℃で2時間反応させた後に、洗浄液のpHが中性となるまで水50gで水洗を3回繰り返した。次いで共沸によって系内を脱水し、精密濾過を経た後に,溶媒を減圧下で留去して、エポキシ樹脂(Ep-1)を190g得た。
前記エポキシ樹脂(Ep-1)のエポキシ当量は2320g/eqであった。
また、前記エポキシ樹脂(Ep-1)は、マススペクトルで測定し、下記構造式(A-1)で示され、下記構造式(A-1)中のm=1、n=12、p1=0、p2=0、q=1の理論構造に相当するM+=883のピークが得られたことから、下記構造式(A-1)で表される構造のエポキシ樹脂(Ep-1)を含有することが確認された。
また、前記エポキシ樹脂(Ep-1)は、下記構造式(A-1)において、q=0の化合物を含んでおり、GPC(図2参照)で確認したところ、q=0の化合物を0.7質量%の割合で含有するものであり、下記構造式(A-1)中のmの平均値は8.0であった。
また、1H-NMRスペクトル(図3参照)により、1.19および1.44ppm付近にドデカン鎖由来のピーク、1.55ppm付近にビスフェノールA構造に含まれるイソプロピリデン結合由来のピーク、2.69~2.82ppmにエポキシ基由来のピーク、5.02ppm付近に脂肪族性水酸基のピーク、6.80~7.06ppmに芳香環由来のピークにより、下記構造式(A-1)で表される構造のエポキシ樹脂(Ep-1)を含有することを確認した。
「J.Polym.Sci.,Part A:Polym.Chem.,53,2094(2015)」に記載の合成方法に従って、Diels-Alder反応付加体(Diamine DA Adduct Cross-Linker)を得た。マススペクトルでM+=237のピークが得られたことから、構造を確認した。
具体的な合成方法としては、定法にてN-Boc-ethylenediamineと無水マレイン酸を酢酸溶媒中でマレイミド化したものと、Boc保護したフルフリルアミンを準備した。これらを酢酸エチル中、室温下で24時間Diels-Alder反応を進めた。得られたDiels-Alder反応付加体(10.0g、22.9mmol)を、最初に0℃でジクロロメタン(100mL)に溶解し、次にトリフルオロ酢酸(40mL)を加えて3時間撹拌し、その間に溶液を室温に到達させた。混合物を濃縮し、ジエチルエーテルで4回(30mL)洗浄した。残った溶媒を蒸発させた後、得られた白色粉末を30mLのメタノールに溶解した。このメタノール溶液は、イオン交換樹脂を数回フラッシュした後、淡黄色に変化した。得られた溶液をアルカリアルミナで濾過し、無水硫酸ナトリウムで乾燥させた。溶媒を減圧下で35℃で蒸発させて、Diamine DA Adduct Cross-Linker(4.3g、80%)を褐色の粘稠な液体として得た。
攪拌機、還流冷却管、窒素導入管、温度計を備えた反応容器に、n-ブチルアクリレート400質量部、エチルアクリレート200質量部、アクリロニトリル200質量部、グリシジルメタクリレート40質量部、フルフリルメタクリレート160質量部、酢酸エチル1000質量部を仕込み、攪拌下、窒素を吹き込みながら70℃まで昇温した。1時間後に、予め酢酸エチルにて溶解した2,2’-アゾビス(2-メチルブチロニトリル)溶液10質量部(固形分5%)を添加した。その後、攪拌下70℃にて8時間ホールドした後、150℃まで昇温し、減圧下で酢酸エチルを留去した。内容物を冷却し、重量平均分子量80万のアクリルポリマー(AP-1)を得た。
「Polymer Vol.37、No.16、3721-3727;1996」に記載の方法に従って、4-アミノフェノールを原料として、4-ヒドロキシフェニルマレイミド(4-HPM)を合成した。マススペクトルでM+=189のピークが得られたことから、構造を確認した。
具体的な合成方法としては、温度計、冷却管、ディーンスタークトラップ、攪拌機を取り付けた3Lフラスコに無水マレイン酸76.5g(0.78mol)、トルエン1.8Lを仕込み室温で攪拌した。次に4-アミノフェノール38.7g(0.35mol)とDMF200mLの混合溶液を1時間かけて滴下した。滴下終了後、室温でさらに2時間反応させた。p-トルエンスルホン酸一水和物9.82gを加え、反応液を加熱し還流下で共沸してくる水とトルエンを冷却・分離した後、トルエンだけを系内に戻して、脱水反応を8時間行った。室温まで空冷後、これを蒸留水に再沈させ、析出した反応物を濾別しつつ、かけ洗いにて洗浄した。反応物を80℃で4時間真空乾燥を行い4-ヒドロキシフェニルマレイミド(4-HPM)を50g得た。
「Nucleosides,Nucleotides and Nucleic Acids」(24、1076~1077(2005)」に記載の合成方法に従って、N-(プロピルトリエトキシシラン)マレイミド(TESiM)を得た。マススペクトルでM+=301のピークが得られたことから、構造を確認した。
具体的な合成方法としては、N-プロピルトリエトキシシランを、溶媒であるジクロロメタン中の無水マレイン酸と混合し、中間体としてN-(プロピルトリエトキシシラン)マレイン酸を得た(反応時間は1時間程度)。続いて、使用した溶媒を除去することで、白色結晶の生成物を単離した。
続いて、N-(プロピルトリエトキシシラン)マレイン酸をマレイミド環化するため、N-(プロピルトリエトキシシラン)マレイン酸を塩化亜鉛とヘキサメタルジサラザンと共に混合し、80℃に加熱し反応させ、N-(プロピルトリエトキシシラン)マレイミド(TESiM)を得た。
[架橋性樹脂組成物及び硬化物の作製]
表1及び表2に従った配合で、エポキシ樹脂などの樹脂、硬化剤、及び、硬化促進剤などを混合機(株式会社シンキー製「あわとり練太郎ARV-200」)にて均一混合して、架橋性樹脂組成物を得た。
得られた架橋性樹脂組成物を、シリコンチューブをスペーサーとして、アルミニウム鏡面板(株式会社エンジニアリングテストサービス製「JIS H 4000 A1050P」)にて挟み込み、それぞれ表1及び表2に記載の硬化条件、及び、エージング条件で硬化反応を行い、熱変形温度測定用に厚さ4mm、修復性評価用に厚さ0.8mmの硬化物を得た。
EPICLON 850S:ビスフェノールA型エポキシ樹脂(DIC株式会社製、エポキシ当量188g/eq)
フルフリルグリシジルエーテル:(関東化学株式会社製)
EP-001(主剤):エポキシ・変性シリコーン系の反応誘発相分離型の二液型接着剤
(セメダイン株式会社製)、ビスフェノールA型エポキシ樹脂を主成分としたエポキシ樹脂組成物にシリコーン樹脂用の硬化触媒である錫化合物が配合されたもの)
EP-001(硬化剤):硬化剤(セメダイン株式会社製)、EP-001(主剤)(変性シリコーン樹脂)にエポキシ樹脂用の硬化触媒である三級アミンが配合されたもの
DICY:ジシアンジアミド(三菱ケミカル株式会社製、「DICY7」)
DDM:ジアミノジフェニルメタン(関東化学株式会社製)
DCMU:3-(3,4-ジクロロフェニル)-1,1-ジメチルウレア(DIC株式会社製、「B-605-IM」)
樹脂硬化物を打抜き刃にてダンベル形状(JIS K 7161-2-1BA)に打ち抜き、これを試験片とした。この試験片を引張試験機(株式会社島津製作所製「オートグラフAG-IS」)を用いて、JIS K 7162-2に従って行ない、測定環境23℃における最大点応力(MPa)、最大点歪み率(%)、および、引張弾性率(MPa)を評価した(試験速度:2mm/min)。
80mm×10mm×厚さ4mmの硬化物を測定に使用した。測定はJIS K7191-1,2:2015に準拠して、フラットワイズでの試験を実施した。具体的には、HDT試験装置「Auto-HDT3D-2」((株)東洋精機製作所製)を用いて、支点間距離64mm、荷重1.80MPa(高荷重)及び0.45MPa(低荷重)、昇温速度120℃/時間の条件にて熱変形温度(℃)を測定した。
再成形前の硬化物(初期値)、および、これを粉砕後に再成形(条件:60℃で24時間、但し、実施例3のみ10℃で24時間)したものを、それぞれを打抜き刃にてダンベル形状(JIS K 7161-2-1BA)に打ち抜き、これを試験片とした。この試験片を引張試験機(株式会社島津製作所製「オートグラフAG-IS」)を用いて、JIS K 7162-2に従って行ない、測定環境23℃における最大点応力(MPa)、及び、最大点歪み率(%)を評価し(試験速度:2mm/min)、「再成形品値/初期値×100」にて、最大点応力修復率(%)、および、最大点歪み率修復率(%)を算出した。
得られた硬化物を、ウルトラミクロトームで断面を作製し、相分離構造の観察を行なった。具体的な観察方法は、走査型電子顕微鏡(SEM)(例えば、実施例1の図1を参照)を用いて行った。
SEM観察により、硬化物中の相分離構造の有無を確認することができ、硬化物が相分離構造を有し、その構造が海島構造を形成する場合は、島部(不連続相)の平均粒径(μm)を測定した。なお、平均粒径については、200μm×260μmの視野の中にある島部(不連続相)から、50個の島部(不連続相)を任意に抽出して粒径を測定し、平均粒径を求めた(実施例1の場合、島部のドメイン平均粒径は1.2μmであり、島部の面積分率は、画像解析式粒度分布測定ソフトウェアMac-View Ver.4.0を用いて、画像処理から、面積分率(%)を算出可能である。画像処理から算出した結果、47%であった。)。
使用機種:日本電子製JSM-7800F、
加速電圧:5kV
一方、比較例においては、硬化物が所望の相分離構造を形成しておらず、化合物Cに相当する化合物を使用した場合であっても、可逆結合の機能が十分に発揮されず、耐熱性(熱変形温度)や機械的強度(引張特性)のいずれかが低い、もしくは、評価することができないほど低く、実施例と比較して、耐熱性や機械的強度、修復性、及び、再成形性を同時に満足でいるものは得られなかった。
Claims (9)
- 連続相、及び、不連続相から形成される相分離構造を有する硬化物を形成可能な架橋性樹脂組成物であって、
前記不連続相が、前記連続相よりも引張弾性率が高く、
前記連続相中に、可逆結合を含有する架橋性樹脂組成物。 - 前記連続相が、前記可逆結合を含有する樹脂成分Aと硬化剤との反応生成物を含み、
前記不連続相が、樹脂成分Bと硬化剤との反応生成物を含み、
前記相分離構造が、前記連続相及び前記不連続相と、前記硬化剤との反応生成物を含む請求項1に記載の架橋性樹脂組成物。 - 前記連続相が、前記可逆結合を含有する樹脂成分Aと硬化剤との反応生成物、及び/または、前記可逆結合を含有する樹脂成分Aの自己重合生成物を含み、
前記不連続相が、樹脂成分Bと硬化剤の反応生成物、及び/または、樹脂成分Bの自己重合生成物を含み、
前記連続相中の官能基(a1)が、前記不連続相中の官能基(b1)と反応性を有し、
前記相分離構造が、前記連続相中の官能基(a1)と前記不連続相中の官能基(b1)との反応生成物を含む請求項1に記載の架橋性樹脂組成物。 - 前記不連続相と、前記連続相の引張弾性率の差が、1000MPa以上である請求項1~3のいずれか1項に記載の架橋性樹脂組成物。
- 前記連続相の引張弾性率が、1000MPa未満である請求項4記載の架橋性樹脂組成物。
- 請求項1~3のいずれか1項に記載の架橋性樹脂組成物が、修復・再成形材料用組成物である架橋性樹脂組成物。
- 請求項1~3のいずれか1項に記載の架橋性樹脂組成物を硬化してなる硬化物。
- 基材と、請求項7に記載の硬化物を含む層と、を有する積層体。
- 請求項7に記載の硬化物を含有する耐熱部材。
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