WO2024071132A1 - 構造体の製造方法 - Google Patents

構造体の製造方法 Download PDF

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Publication number
WO2024071132A1
WO2024071132A1 PCT/JP2023/034977 JP2023034977W WO2024071132A1 WO 2024071132 A1 WO2024071132 A1 WO 2024071132A1 JP 2023034977 W JP2023034977 W JP 2023034977W WO 2024071132 A1 WO2024071132 A1 WO 2024071132A1
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Prior art keywords
compound
photoradical generator
less
adherend
light
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PCT/JP2023/034977
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English (en)
French (fr)
Japanese (ja)
Inventor
祐樹 宮本
真幸 和田
圭市 坂本
秀一 近藤
晃一 斉藤
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Resonac Corp
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Resonac Corp
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Priority to KR1020257013160A priority Critical patent/KR20250079167A/ko
Priority to JP2024550351A priority patent/JPWO2024071132A1/ja
Priority to CN202380080799.7A priority patent/CN120239736A/zh
Publication of WO2024071132A1 publication Critical patent/WO2024071132A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J181/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Adhesives based on polysulfones; Adhesives based on derivatives of such polymers
    • C09J181/02—Polythioethers; Polythioether-ethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers

Definitions

  • This disclosure relates to a method for manufacturing a structure.
  • Patent Document 1 discloses an image forming apparatus equipped with a recording member having a resin layer made of a photosoftening composition.
  • compositions that exhibit photosoftening properties are expected to be used, for example, as adhesives that allow the repair of components by irradiating them with light after assembling the components to create a structure.
  • adhesive joints that contain such adhesives it is required that photosoftening properties (photomelting properties) be expressed when repair is required, and that the expression of photosoftening properties (photomelting properties) be suppressed by a simple method when repair is not required.
  • the present disclosure therefore aims to provide a method for producing a structure that can suppress the development of photosoftening properties in an adhesive joint that contains a composition that exhibits photosoftening properties using a simple method.
  • the photosoftening composition contains a photosoftening (photomelting) resin (a resin that becomes a lower molecular weight when irradiated with light) and a photoradical generator.
  • a photosoftening (photomelting) resin a resin that becomes a lower molecular weight when irradiated with light
  • the inventors' studies have found that a certain photosoftening resin exhibits photosoftening properties when irradiated with light in the presence of a photoradical generator. Further studies by the inventors have found that the development of photosoftening (photomelting) properties can be suppressed by heating a photosoftening composition containing these and volatilizing at least a portion of the photoradical generator, which led to the completion of the present invention.
  • a method for producing a structure comprising: a first step of preparing a first structure, the first structure comprising a first adherend, a second adherend, and an adhesive part for adhering the first adherend and the second adherend to each other, the adhesive part containing a cured product of a curable composition comprising a compound A having two or more thiol groups, a compound B having two or more functional groups capable of reacting with the thiol groups, and a photoradical generator, and at least one of the compound A and the compound B having a disulfide bond in its molecule; and a second step of heating the first structure to volatilize at least a portion of the photoradical generator contained in the adhesive part to obtain a second structure.
  • the present disclosure provides a method for producing a structure that can suppress the development of photosoftening properties in an adhesive joint that contains a composition that exhibits photosoftening properties using a simple method.
  • FIG. 1 is a schematic cross-sectional view showing one embodiment of a first structure
  • FIG. 1(a), FIG. 1(b), and FIG. 1(c) are views showing various aspects of the first structure.
  • FIG. 2 shows test samples prepared for adhesive strength evaluation.
  • process refers not only to an independent process, but also to processes that cannot be clearly distinguished from other processes, as long as the intended effect of the process is achieved.
  • a numerical range indicated using “ ⁇ ” indicates a range that includes the numerical values written before and after " ⁇ " as the minimum and maximum values, respectively.
  • each component in the curable composition when there are multiple substances corresponding to each component in the curable composition, the content of each component means the total amount of the multiple substances, unless otherwise specified.
  • each of the example materials may be used alone or in combination of two or more types.
  • the upper or lower limit of a certain numerical range may be replaced with the upper or lower limit of another numerical range.
  • the upper or lower limit of the numerical range may be replaced with a value shown in the examples.
  • “A or B” may include either A or B, or may include both.
  • (meth)acryloyl group means a methacryloyl group or an acryloyl group.
  • “weight average molecular weight” is a polystyrene-equivalent value obtained by using a calibration curve of standard polystyrene in gel permeation chromatography (GPC). In this specification, "room temperature” means 25°C.
  • photosoftening refers to the property of softening (or melting) when irradiated with light.
  • the property of softening (or melting) includes, for example, a decrease in elastic modulus and an increase in loss tangent (tan ⁇ ).
  • softened material (melted material) refers to a material in which the elastic modulus is decreased or the loss tangent (tan ⁇ ) is increased based on the composition before light irradiation (cured material of a curable composition).
  • a composition that exhibits photosoftening (photomelting) refers to a composition that softens (melts) when irradiated with light to give a gel or liquid material.
  • a method for manufacturing a structure includes a first step and a second step.
  • This step is a step of preparing a first structure comprising a first adherend, a second adherend, and an adhesive portion that adheres the first adherend and the second adherend to each other, the adhesive portion containing a reaction product of a compound A having two or more thiol groups and a compound B having two or more functional groups capable of reacting with the thiol groups, and a photoradical generator, wherein at least one of compound A and compound B has a disulfide bond in the molecule.
  • FIG. 1 is a schematic cross-sectional view showing one embodiment of the first structure
  • FIG. 1(a), FIG. 1(b), and FIG. 1(c) are views showing various aspects of the first structure.
  • the first structure is not particularly limited as long as it includes a first adherend, a second adherend, and an adhesive portion for adhering the first adherend and the second adherend to each other.
  • the main surface 1a of the first adherend 1 and the main surface 2a of the second adherend 2 are adhered to each other via the adhesive portion 3.
  • the main surface 1a of the first adherend 1 and the side surface 2b of the second adherend 2 are adhered to each other via the adhesive portion 3.
  • the side surface 1b of the first adherend 1 and the side surface 2b of the second adherend 2 are adhered to each other via the adhesive portion 3. Since the first structure is heated to volatilize at least a portion of the photoradical generator contained in the adhesive portion, it is preferable that the proportion of the exposed surface of the adhesive portion is large.
  • first adherend 1 and the second adherend 2 examples include plastics such as polyolefin resin, polyamide resin, ABS (acrylonitrile butadiene styrene) resin, PC (polycarbonate) resin, PET (polyethylene terephthalate) resin, PPS (polyphenylene sulfide) resin, and acrylic resin; inorganic materials such as steel, stainless steel, metals (aluminum, copper, nickel, chromium, etc.) or alloys of these metals, glass, and silicon wafers; wood; and rubber.
  • plastics such as polyolefin resin, polyamide resin, ABS (acrylonitrile butadiene styrene) resin, PC (polycarbonate) resin, PET (polyethylene terephthalate) resin, PPS (polyphenylene sulfide) resin, and acrylic resin
  • inorganic materials such as steel, stainless steel, metals (aluminum, copper, nickel, chromium, etc.) or alloys of
  • the thickness of the first adherend 1 and the second adherend 2 is not particularly limited, but may be 0.05 to 20 mm, 0.1 to 10 mm, or 0.5 to 5 mm.
  • the adhesive portion 3 contains a cured product of a curable composition containing a compound A, a compound B, and a photoradical generator.
  • the curing of the curable composition mainly proceeds by the reaction (thermal reaction or photoreaction) between compound A and compound B. That is, it can be said that the adhesive portion 3 contains at least a reaction product (thermal reaction product or photoreaction product) of compound A and compound B, and a photoradical generator.
  • the cured product of the curable composition may be a cured product of a thermosetting composition or a cured product of a photocurable composition.
  • the thermosetting composition may contain compound A, compound B, a photoradical generator, and, if necessary, a curing catalyst.
  • the curing catalyst may be a component that mainly contributes to the reaction between compound A and compound B.
  • the photoradical generator may be a component that mainly contributes to the low molecular weight of the reaction product of compound A and compound B.
  • the photocurable composition may contain compound A, compound B, a first photoradical generator, and a second photoradical generator.
  • the first photoradical generator may be a component that mainly contributes to the reaction between compound A and compound B.
  • the second photoradical generator may be a component that mainly contributes to the degradation of the reaction product of compound A and compound B into lower molecular weight compounds.
  • Compound A is a compound having two or more thiol groups (-SH) in one molecule.
  • the upper limit of the number of thiol groups of compound A per molecule may be, for example, 10 or less, 8 or less, 6 or less, or 4 or less.
  • Compound A may be a compound having two thiol groups.
  • Compound A may have a disulfide bond in the molecule.
  • the molecular weight or weight average molecular weight of compound A may be 300 or more, 500 or more, or 1000 or more, and may be 50000 or less, 10000 or less, or 5000 or less.
  • the number of disulfide bonds in one molecule may be, for example, 1 to 1000 or 4 to 50.
  • Compound A may be a compound (e.g., a polymer or oligomer) having a linear molecular chain and terminal groups, with disulfide bonds in the molecular chain.
  • the terminal group in compound A may be a thiol group.
  • the molecular chain in compound A may contain a disulfide bond and a polyether chain, or may be composed of a disulfide bond and a polyether chain.
  • Compound A may be, for example, a compound represented by formula (1): HS-(A-S-S) p -A-SH (compound (1)).
  • A represents a polyether chain.
  • a plurality of As may be the same or different.
  • p represents an integer of 1 or more.
  • p may be, for example, 1 or more, or 4 or more, or 1000 or less.
  • Compound A may be a compound obtained by chain extension of compound (1).
  • the polyether chain represented by A may be, for example, a polyoxyalkylene chain.
  • the polyether chain represented by A may be, for example, a group represented by -A 1 -O-A 2 -O-A 3 -.
  • a 1 to A 3 may each independently be an alkylene group, or an alkylene group having 1 to 2 carbon atoms (for example, a methylene group, an ethylene group).
  • An example of the polyether chain represented by A is -CH 2 CH 2 -O-CH 2 -O-CH 2 CH 2 -.
  • Compound A may be used alone or in combination of two or more types.
  • Compound A can also be obtained by converting the reactive functional group of a compound having a reactive functional group (e.g., a carboxy group, a hydroxy group) and a disulfide bond at its terminal into a thiol group.
  • a compound having a reactive functional group e.g., a carboxy group, a hydroxy group
  • examples of compounds having a reactive functional group and a disulfide bond at its terminal include 3,3'-dithiodipropionic acid, dithiodiethanol, and cystamine.
  • the content of compound A may be 20 mass% or more, 40 mass% or more, or 60 mass% or more, and may be 95 mass% or less, 92 mass% or less, or 90 mass% or less, based on the total amount of the curable composition (solid content excluding the solvent).
  • Compound B is a compound having two or more functional groups capable of reacting with a thiol group.
  • the upper limit of the number of functional groups in compound B may be, for example, 10 or less, 8 or less, 6 or less, or 4 or less per molecule.
  • Compound B may be a compound having two or three functional groups.
  • compound B may be compound B1 having two or more isocyanate groups.
  • Compound B1 may contain, for example, compound B1(1) having two isocyanate groups and compound B1(2) having three or more isocyanate groups.
  • compound B1(1) examples include aliphatic diisocyanates such as ethylene diisocyanate, propylene diisocyanate, butylene diisocyanate, hexamethylene diisocyanate, and trimethylhexamethylene diisocyanate; alicyclic diisocyanates such as isophorone diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, norbornane diisocyanate, 1,4-isocyanatocyclohexane, 1,3-bis(isocyanatomethyl)-cyclohexane, and 1,3-bis(2-isocyanatopropyl-2yl)-cyclohexane; and aromatic diisocyanates such as tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, xylene diisocyanate, and 1,5-naphthalene diisocyanate.
  • compound B1(1) may be an aliphatic diis
  • Examples of compound B1(2) include triphenylmethane-4,4',4''-triisocyanate, 1,3,5-triisocyanatobenzene, 1,3,5-tris(isocyanatomethyl)cyclohexane, 1,3,5-tris(isocyanatomethyl)benzene, and 2,6-diisocyanatocaproic acid-2-isocyanatoethyl.
  • Examples of compound B1(2) include the trimer of compound B1(1) above. Among these, compound B1(2) may be a trimer of an aliphatic diisocyanate or a trimer of hexamethylene diisocyanate (HDI).
  • the isocyanate group may be protected with a blocking agent.
  • a blocking agent Compounds in which the isocyanate group is protected with a blocking agent are usually stable at room temperature, but when heated to a temperature equal to or higher than the dissociation temperature of the blocking agent, free isocyanate groups are generated.
  • blocking agents include methyl ethyl ketone oxime (MEKO, dissociation temperature 130°C), dimethylpyrazole (DMP, dissociation temperature 110°C), diethyl malonate (DEM, dissociation temperature 110°C), and active methylene compounds (dissociation temperature 90°C).
  • the molecular weight or weight average molecular weight of compound B1 may be 150 or more, and may be 10,000 or less, 1,000 or less, or 600 or less.
  • compound B may be compound B2 having two or more ethylenically unsaturated groups.
  • Compound B2 may be, for example, a compound having two or more groups selected from the group consisting of an allyl group (H 2 C ⁇ CH—CH 2 —), a vinyloxy group (H 2 C ⁇ CH—O—), and a (meth)acryloyl group.
  • One aspect of compound B2 may be compound B2a having two or more groups selected from the group consisting of an allyl group and a vinyloxy group, since this has better photocurability.
  • Compound B2a may include, for example, compound B2a(1) having two groups selected from the group consisting of allyl groups and vinyloxy groups, and compound B2a(2) having three or more groups selected from the group consisting of allyl groups and vinyloxy groups.
  • Examples of compound B2a(1) include compounds having two allyl groups, such as diallyl isophthalate and diallyl terephthalate; and compounds having two vinyloxy groups, such as triethylene glycol divinyl ether, 1,4-cyclohexanedimethanol divinyl ether, diethylene glycol divinyl ether, and 1,4-butanediol divinyl ether.
  • Examples of compound B2a(2) include triallyl isocyanurate, triallyl trimellitate, triallyl citrate, and pentaerythritol tetraallyl ether.
  • the molecular weight or weight average molecular weight of compound B2a may be 150 or more, and may be 10,000 or less, 1,000 or less, or 600 or less.
  • compound B2 may be compound B(2b) having two or more (meth)acryloyl groups, since it has better thermosetting properties.
  • Compound B2b may include, for example, compound B2b(1) having two (meth)acryloyl groups and compound B2b(2) having three or more (meth)acryloyl groups.
  • Compound B2b(1) may be, for example, a compound represented by the following formula (x1):
  • R 2 represents a hydrogen atom or a methyl group.
  • L 2 represents an alkylene group.
  • a plurality of R 2s may be the same or different.
  • the number of carbon atoms of the alkylene group represented by L 2 may be 2 or more, and may be 10 or less, 6 or less, or 3 or less.
  • the alkylene group represented by L 2 may be, for example, an ethylene group (-CH 2 -CH 2 -).
  • m represents an integer of 1 or more.
  • m may be 2 or more, or 3 or more.
  • the upper limit of m may be, for example, 10 or less, 8 or less, 6 or less, or 5 or less.
  • a plurality of L 2s may be the same or different.
  • Examples of compound B2b(2) include compounds having a trimethylolpropane skeleton and three or more (meth)acryloyl groups, compounds having a pentaerythritol skeleton and three or more (meth)acryloyl groups, and compounds having an isocyanurate skeleton and three or more (meth)acryloyl groups.
  • the molecular weight or weight average molecular weight of compound B2b may be 150 or more, 500 or more, or 1000 or more, and may be 50000 or less, 10000 or less, or 2000 or less.
  • compound B may be compound B3 having two or more epoxy groups.
  • An example of compound B3 is an epoxy resin.
  • Epoxy resins include, for example, novolac type epoxy resins (phenol novolac type epoxy resins, orthocresol novolac type epoxy resins, etc.); triphenylmethane type epoxy resins; copolymer type epoxy resins; diphenylmethane type epoxy resins; biphenyl type epoxy resins; stilbene type epoxy resins; glycidyl ester type epoxy resins; glycidylamine type epoxy resins; dicyclopentadiene type epoxy resins; aliphatic type epoxy resins (polyethylene glycol diglycidyl ether, sorbitol polyglycidyl ether, etc.); alicyclic type epoxy resins (vinylcyclohexene diepoxide, 3,4-epoxycyclohexene These include silylmethyl-3,4-epoxycyclohexanecarboxylate, 2-(3,4-epoxy)cyclohexyl-5,5-spiro(3,4-epoxy)
  • the molecular weight or weight average molecular weight of compound B3 may be 150 or more, 500 or more, or 1000 or more, and may be 50000 or less, 10000 or less, or 2000 or less.
  • the number of disulfide bonds in one molecule may be, for example, 1 to 1000 or 4 to 50.
  • the content of compound B may be 1 mass% or more, 2 mass% or more, or 3 mass% or more, and may be 30 mass% or less, 20 mass% or less, or 10 mass% or less, based on the total amount of the curable composition (solid content excluding the solvent).
  • the ratio of the total number of moles of thiol groups in compound A to the total number of moles of functional groups in compound B may be, for example, 0.90 or more, or 0.95 or more, and may be 1.10 or less, or 1.05 or less.
  • the photoradical generator is a component that generates radicals by irradiation with light.
  • a component used as a photopolymerization initiator can be used as the photoradical generator.
  • the photoradical generator include an intramolecular cleavage type photoradical polymerization initiator that is photocleaved by irradiation with light to generate two radicals.
  • intramolecular cleavage type photoradical generators examples include benzyl ketal-based photoradical generators, ⁇ -aminoalkylphenone-based photoradical generators, ⁇ -hydroxyalkylphenone-based photoradical generators, ⁇ -hydroxyacetophenone-based photoradical generators, and acylphosphine oxide-based photoradical generators.
  • the 5% weight loss temperature of the photoradical generator may be 180°C or lower.
  • the 5% weight loss temperature means the temperature at which the mass of the sample is reduced by 5% from the initial mass in a thermogravimetric analysis in which the change in mass of the sample is measured while the temperature is increased.
  • the 5% weight loss temperature of the photoradical generator may be 170°C or lower, 160°C or lower, 150°C or lower, 140°C or lower, 130°C or lower, 120°C or lower, or 110°C or lower, since this can more sufficiently suppress the softening (melting) of the adhesive portion due to light irradiation.
  • the lower limit of the 5% weight loss temperature of the photoradical generator may be, for example, 80°C or higher.
  • photoradical generators with a 5% weight loss temperature of 180°C or less examples include 2-hydroxy-2-methyl-1-phenyl-propan-1-one (Omnirad-1173, 5% weight loss temperature: 101°C), 1-hydroxy-cyclohexyl-phenyl-ketone (Omnirad-184, 5% weight loss temperature: 155°C), and 2,2-dimethoxy-1,2-diphenylethan-1-one (Omnirad-651, 5% weight loss temperature: 170°C).
  • the photoradical generator may be 2-hydroxy-2-methyl-1-phenyl-propan-1-one (Omnirad-1173).
  • the content of the photoradical generator may be 1 mass% or more, 3 mass% or more, or 5 mass% or more based on the total amount of the curable composition (solid content excluding the solvent), and may be 30 mass% or less, 20 mass% or less, or 15 mass% or less.
  • the ratio of the number of moles of the photoradical generator to the number of moles of compound A may be 0.1 or more, 0.2 or more, or 0.3 or more, since this further improves the photosoftening properties.
  • the thermosetting composition may be a combination of compound A, compound B1, and a photoradical generator, a combination of compound A, compound B2, and a photoradical generator, or a combination of compound A, compound B3, and a photoradical generator.
  • These combinations may contain a curing catalyst as necessary.
  • the curing catalyst is a component for promoting the reaction between compound A and compound B.
  • the curing catalyst include amine compounds and phosphorus compounds.
  • the curing catalyst may be an amine compound.
  • the amine compound may be, for example, a secondary amine compound or a tertiary amine compound.
  • the amine compound include dicyandiamide, trimethylamine, triethylamine, tripropylamine, tributylamine, tri-n-octylamine, dimethylethylamine, dimethylpropylamine, dimethylbutylamine, dimethyl-n-octylamine, 1,4-diazabicyclo[2.2.2]octane, 1,8-diazabicyclo[5.4.0]undec-7-ene, benzyldimethylamine, 4-methyl-N,N-dimethylbenzylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and 4-dimethylaminopyridine.
  • the content of the curing catalyst may be 0.001% by mass or more, 0.01% by mass or more, or 0.015% by mass or more, and may be 3% by mass or less, 2% by mass or less, or 1% by mass or less, based on the total amount of the curable composition (solid content excluding the solvent).
  • the photocurable composition may be a combination of compound A, compound B2, a first photoradical generator, and a second photoradical generator.
  • the first photoradical generator may be an intramolecular cleavage type photoradical generator having an absorption coefficient at the first wavelength of 1.0 ⁇ 10 2 mL/(g cm) or more
  • the second photoradical generator may be an intramolecular cleavage type photoradical generator having an absorption coefficient at the first wavelength of less than 1.0 ⁇ 10 2 mL/(g cm).
  • the absorption coefficient is a value measured in methanol or acetonitrile.
  • the photocurable composition contains a first photoradical generator and a second photoradical generator
  • the cured product of the photocurable composition obtained by irradiating the first light containing light of a first wavelength with a second light containing light of a wavelength (second wavelength) different from the first wavelength can be softened (melted).
  • the second light may contain light of a second wavelength that is shorter than the first wavelength.
  • the first wavelength may be, for example, 447 nm or 405 nm. If the first wavelength is 447 nm, the second wavelength may be 405 nm or 365 nm. If the first wavelength is 405 nm, the second wavelength may be 365 nm.
  • the first photoradical generator may be a photoradical generator having an absorption coefficient at a wavelength of 447 nm of 1.0 ⁇ 10 2 or more.
  • An example of such a first photoradical generator is bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (Omnirad-819).
  • the first photoradical generator may be a photoradical generator having an absorption coefficient at a wavelength of 447 nm of less than 1.0 ⁇ 10 2 and an absorption coefficient at a wavelength of 405 nm of 1.0 ⁇ 10 2 or more.
  • Examples of such a first photoradical generator include 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1 (Omnirad-369) and 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (Omnirad-TPO).
  • the second photoradical generator may be a component corresponding to the photoradical generator in the thermosetting composition.
  • the second photoradical generator may be a photoradical generator having an absorption coefficient at a wavelength of 447 nm and an absorption coefficient at a wavelength of 405 nm of less than 1.0 ⁇ 10 2 and a 5% weight loss temperature of 180 ° C. or less.
  • Examples of such second photoradical generators include 2-hydroxy-2-methyl-1-phenyl-propan-1-one (Omnirad-1173, 5% weight loss temperature: 101 ° C.), 1-hydroxy-cyclohexyl-phenyl-ketone (Omnirad-184, 5% weight loss temperature: 155 ° C.), 2,2-dimethoxy-1,2-diphenylethan-1-one (Omnirad-651, 5% weight loss temperature: 170 ° C.), and the like.
  • Suitable combinations of the first photoradical generator and the second photoradical generator include, for example, a combination of Omnirad-819 and Omnirad-1173, a combination of Omnirad-369 and Omnirad-1173, and a combination of Omnirad-TPO and Omnirad-1173.
  • the content of the first photoradical generator may be 0.1 mass% or more, 0.5 mass% or more, or 1 mass% or more, and may be 10 mass% or less, 5 mass% or less, or 3 mass% or less, based on the total amount of the curable composition (solid content excluding the solvent).
  • the content of the second photoradical generator may be the same as the content of the photoradical generator described above, and may be 1 mass% or more, 3 mass% or more, or 5 mass% or more based on the total amount of the curable composition (solid content excluding solvent), and may be 30 mass% or less, 20 mass% or less, or 15 mass% or less.
  • the curable composition may further contain compound A, compound B, photoradical generators (first photoradical generator and second photoradical generator), and components that do not fall under the category of curing catalysts (other components).
  • the other components include additives such as plasticizers, tackifiers and other tackifiers, antioxidants, leuco dyes, sensitizers, adhesion improvers such as coupling agents, polymerization inhibitors, light stabilizers, defoamers, fillers, chain transfer agents, thixotropy-imparting agents, flame retardants, release agents, surfactants, lubricants, and antistatic agents.
  • additives may be known ones.
  • the total content of the other components may be 0 to 95% by mass, 0.01 to 50% by mass, or 0.1 to 10% by mass based on the total amount of the curable composition.
  • the curable composition may be used as a varnish of the curable composition diluted with a solvent.
  • the solvent include aromatic hydrocarbons such as toluene, xylene, mesitylene, cumene, and p-cymene; aliphatic hydrocarbons such as hexane and heptane; cyclic alkanes such as methylcyclohexane; cyclic ethers such as tetrahydrofuran and 1,4-dioxane; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and 4-hydroxy-4-methyl-2-pentanone; esters such as methyl acetate, ethyl acetate, butyl acetate, methyl lactate, ethyl lactate, and ⁇ -butyrolactone; carbonates such as ethylene carbonate and propylene carbonate; and amides such as N,N-
  • the curable composition can be prepared, for example, by a method including a step of mixing or kneading the above-mentioned components.
  • Mixing and kneading can be performed by appropriately combining a conventional mixer, a mixing machine, a triple roll mill, a ball mill, a bead mill, or other dispersing machine.
  • the reaction temperature of compound A and compound B may be, for example, 0 to 50°C, or may be 5 to 45°C or 10 to 40°C.
  • the time for which the reaction temperature is maintained may be, for example, 0.1 to 168 hours, or may be 72 hours or less, 24 hours or less, 12 hours or less, 6 hours or less, 4 hours or less, 3 hours or less, or 2 hours or less.
  • the light used to form a cured product may be, for example, ultraviolet light or visible light.
  • the wavelength of the curing light can be appropriately selected depending on, for example, the type of intramolecular cleavage type photoradical generator used.
  • the wavelength of the curing light may be, for example, 150 to 830 nm.
  • the curing light may include, for example, light with a wavelength of 447 nm, 405 nm, or 365 nm.
  • the light irradiation can be performed, for example, using a light irradiation device under conditions of an irradiation amount of 100 mJ/ cm2 or more.
  • the irradiation amount can be appropriately set, for example, depending on the wavelength of the light for curing.
  • the irradiation amount may be, for example, 1000 mJ/ cm2 or more, 2000 mJ/ cm2 or more, or 3000 mJ/ cm2 or more, and may be 10000 mJ/ cm2 or less, 7000 mJ/ cm2 or less, or 5000 mJ/ cm2 or less.
  • the amount of irradiation means the product of illuminance and irradiation time (seconds).
  • Examples of light sources for irradiating ultraviolet light or visible light include low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, metal halide lamps, LED lamps, etc.
  • the light irradiation may be performed directly on the photocurable composition or through glass, etc.
  • the cured product of the curable composition is formed by the progress of a reaction (thermal reaction or photoreaction) between compound A and compound B in the curable composition. It can be said that the adhesive part 3 contains at least a reaction product (thermal reaction product or photoreaction product) of compound A and compound B, and a photoradical generator (second photoradical generator).
  • * indicates a bond.
  • the disulfide bond may be present in at least one of the main chain and side chain of the reaction product. Since this further improves the photosoftening properties, the disulfide bond may be present in the main chain of the reaction product.
  • the reaction product of compound A and compound B2 is formed by a reaction between a thiol group in compound A and an ethylenically unsaturated group in compound B2 (enethiol reaction or Michael addition reaction). That is, the reaction product of compound A and compound B has a structure represented by formula (II): *-CH 2 -CH 2 -S-* or *-C( ⁇ O)-CHR-CH 2 -S-*, and a disulfide bond.
  • * represents a bond.
  • the disulfide bond may be present in at least one of the main chain and the side chain of the reaction product. Since the photosoftening property is further improved, the disulfide bond may be present in the main chain of the reaction product.
  • the reaction product of compound A and compound B3 is formed by a reaction (ring-opening reaction) between a thiol group in compound A and an epoxy group in compound B3. That is, the reaction product of compound A and compound B has a structure represented by formula (III): *-CH(OH)-CH 2 -S-* or *-CH(CH 2 OH)-S-*, and a disulfide bond.
  • * represents a bond.
  • the disulfide bond may be present in at least one of the main chain and the side chain of the reaction product. Since the photosoftening property is further improved, the disulfide bond may be present in the main chain of the reaction product.
  • the thickness of the adhesive portion 3 may be 10 to 2000 ⁇ m, 30 to 1000 ⁇ m, or 50 to 500 ⁇ m.
  • the cured product of the curable composition contains a reaction product (thermal reaction product or photoreaction product) of compound A and compound B, which exhibits photosoftening (photomelting). Therefore, the cured product of the curable composition can be photosoftened (photomelted) by irradiating it with light in the presence of a photoradical generator (second photoradical generator).
  • the mechanism by which the cured product of the curable composition is photomelted is not necessarily clear, but the following mechanisms are possible. However, the mechanisms are not limited to these. At least one of compound A and compound B has a disulfide bond in the molecule, so the cured product of the curable composition contains a compound (a reaction product of compound A and compound B) having a disulfide bond.
  • the disulfide bond in the cured product is decomposed (cleaved) and a thiyl radical is generated.
  • a photoradical generator intramolecular cleavage type photoradical generator
  • the thiyl radical reacts with the photoradical generator, and the thiyl radical is capped by the photoradical generator. It is believed that this causes the compound with disulfide bonds to become low molecular weight, and the cured product is photosoftened (photomelted).
  • photoinduced radicals caused by a photoradical generator (intramolecular cleavage-type photoradical generator) react directly with disulfide bonds, forming a photoinduced radical-thioether bond and generating a thiyl radical, which then reacts with another photoinduced radical, causing the compound with disulfide bonds itself to become low molecular weight and soften the photocured product.
  • the reaction in which disulfide bonds are cleaved can be said to be an irreversible reaction.
  • the first structures 10, 20, 30 can be obtained, for example, by a method including a step of preparing a structural precursor obtained by bonding a first adherend 1 and a second adherend 2 via a curable composition, and a step of reacting compound A and compound B contained in the curable composition in the structural precursor to form a cured product (adhesive portion) of the curable composition.
  • the reaction conditions reaction temperature, holding time, etc.
  • the reaction conditions wavelength, irradiation amount, etc.
  • photoreacting compound A and compound B may be the same as above.
  • the adhesive portion of the first structure contains a cured product of the curable composition, so that the adhesive portion becomes softenable (meltable) when irradiated with light, allowing the first adherend to be easily peeled away from the second adherend.
  • the light (melting light) used to soften (melt) the cured product of the curable composition may be, for example, ultraviolet light or visible light.
  • the wavelength of the melting light may be appropriately selected depending on, for example, the type of photoradical generator used.
  • the wavelength of the melting light may be, for example, 150 to 830 nm.
  • the melting light may include, for example, light with a wavelength of 405 nm or 365 nm.
  • the light irradiation can be performed, for example, using a light irradiation device under conditions where the irradiation amount is more than 3000 mJ/cm 2.
  • the irradiation amount can be appropriately set, for example, depending on the wavelength of the light for melting.
  • the irradiation amount may be, for example, 15000 mJ/cm 2 or more, 20000 mJ/cm 2 or more, or 25000 mJ/cm 2 or more, and may be 100000 mJ/cm 2 or less, 50000 mJ/cm 2 or less, or 35000 mJ/cm 2 or less.
  • This step is a step of heating the first structure and volatilizing at least a part of the photoradical generator (second photoradical generator) contained in the adhesive portion to obtain a second structure.
  • the second structure corresponds to the "structure” in the method for producing a structure of this embodiment. This makes it possible to obtain a structure (second structure) in which the amount of photoradical generator contained in the adhesive portion is less than the amount of photoradical generator contained in the adhesive portion of the first structure.
  • the present inventors speculate that by volatilizing at least a part of the photoradical generator (second photoradical generator) in the first structure, the amount of photoradical generator (second photoradical generator) required for the development of photosoftening (photomelting) becomes insufficient, and as a result, the development of photosoftening (photomelting) can be suppressed.
  • the atmosphere in which the first structure is heated is not particularly limited, but may be, for example, an air atmosphere or an inert gas atmosphere such as nitrogen or argon.
  • the atmospheric pressure conditions when the first structure is heated are not particularly limited, but may be atmospheric pressure conditions or reduced pressure (negative pressure) conditions.
  • the heating temperature when heating the first structure is not particularly limited and can be set arbitrarily according to the properties of the photoradical generator.
  • the heating temperature may be, for example, a temperature higher than the 5% weight loss temperature of the photoradical generator contained in the adhesive portion. Heating under such temperature conditions can more fully volatilize the photoradical generator.
  • the heating temperature may be a temperature 5°C higher than the 5% weight loss temperature of the photoradical generator, or may be a temperature 10°C higher than the 5% weight loss temperature of the photoradical generator.
  • the heating temperature may be, for example, higher than 110°C, 120°C or higher, 300°C or lower, or 200°C or lower.
  • the time for which the heating temperature is maintained may be, for example, 0.1 to 72 hours, and may be 0.5 hours or more, 1 hour or more, 1.5 hours or more, or 2 hours or more, and may be 36 hours or less, 24 hours or less, 12 hours or less, or 8 hours or less.
  • the heating device used to heat the first structure is not particularly limited, but an oven, a hot plate, or the like can be used. Since the first structure can be heated, the heating device may be, for example, an oven capable of controlling the temperature.
  • a structure (second structure) that has an adhesive portion in which the softening (melting) property caused by light irradiation is suppressed.
  • the softening (melting) property caused by light irradiation of the adhesive portion is suppressed, so that when the adhesive portion is irradiated with light, the first adherend and the second adherend are less likely to peel off than with the first structure.
  • B1(2)-1 1,3,5-tris(6-isocyanatohex-1-yl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (des Module N-3300 (HDI trimmer), manufactured by Sumika Covestro Urethane Co., Ltd., molecular weight 504.6)
  • Curing catalyst D-1 Triethylamine (TEA, manufactured by Tokyo Chemical
  • thermosetting composition The test materials were blended according to the following procedure with the composition ratio shown in Table 1. First, compound A and the curing catalyst were blended in a 30 mL plastic ointment pot. At this time, the blending amount of compound A was adjusted so that the content of the curing catalyst was 1 mass% based on the total amount of compound A and the curing catalyst. Next, the blend was stirred for 1.5 minutes at a rotation speed of 2000 rpm using a self-revolving mixer (Awatori Rentaro ARE-310, manufactured by Thinky Corporation) to obtain a mixture a.
  • a self-revolving mixer Alwatori Rentaro ARE-310, manufactured by Thinky Corporation
  • thermosetting composition of Production Example 1 the remaining compound A, compound B, and photoradical generator were blended in a 30 mL plastic ointment pot, and the blend was stirred for 1.5 minutes at a rotation speed of 2000 rpm using the same self-revolving mixer to obtain a mixture b.
  • the mixture a and the mixture b were blended in a 30 mL plastic ointment pot, and the blend was stirred for 1.5 minutes at a rotation speed of 2000 rpm to prepare a thermosetting composition of Production Example 1.
  • UV irradiation For UV irradiation, a UV irradiation device (manufactured by Panasonic Device SUNX Co., Ltd., power supply: Aicure UJ30, 365 nm LED head: ANUJ6186) was used. The irradiation conditions were as follows: a 365 nm light receiver was used with a luminometer UIT-250 (manufactured by Ushio Inc.).
  • thermosetting composition of Production Example 1 was sandwiched between the two slide glasses so as to have a length of 65 mm, a width of 2.0 mm, and a thickness of 100 ⁇ m, as shown in FIG. 2, and cured at room temperature for one week to obtain a plurality of shear test samples (1a).
  • the adhesive joint of the obtained shear test sample (1a) was irradiated with LED light having a wavelength of 365 nm at an illuminance of 1000 mW/cm 2 for 10 seconds to obtain a shear test sample (1b).
  • the obtained shear test sample (1a) was heated in a small high temperature chamber (ST-120, manufactured by Espec Corporation) at 120° C. for 2 hours.
  • the adhesive joint of the heated shear test sample (1a) was irradiated with LED light having a wavelength of 365 nm at an illuminance of 1000 mW/cm 2 for 10 seconds to obtain a shear test sample (1c).
  • the shear adhesive strength of the obtained shear test samples (1a) to (1c) was measured at room temperature (25°C) at a tensile speed of 10 mm/min using an autograph AGS-X manufactured by Shimadzu Corporation. The results are shown in Table 1.
  • UV irradiation For UV irradiation, a UV irradiation device (manufactured by Panasonic Industrial Devices SUNX Co., Ltd., power supply: Aicure UJ30, 405 nm LED head: ANUJ6189, 365 nm LED head: ANUJ6186) was used. The irradiation conditions were as follows: 405 nm and 365 nm receivers were used with an illuminometer UIT-250 (manufactured by Ushio Inc.).
  • the adhesive joints of the obtained shear test samples (2a) and (3a) were irradiated with LED light having a wavelength of 365 nm at an illuminance of 1000 mW/ cm2 for 10 seconds to obtain shear test samples (2b) and (3b).
  • the obtained shear test samples (2a) and (3a) were heated in a small high temperature chamber (ST-120, manufactured by Espec Corporation) at 120° C. for 2 hours. After heating, the adhesive joints of the shear test samples (2a) and (3a) were irradiated with LED light having a wavelength of 365 nm at an illuminance of 1000 mW/cm 2 for 10 seconds to obtain shear test samples (2c) and (3c).
  • the obtained shear test samples (2a) and (3a) were heated in a small high temperature chamber (ST-120, manufactured by Espec Corporation) at 120° C. for 4 hours. After heating, the adhesive joints of the shear test samples (2a) and (3a) were irradiated with LED light having a wavelength of 365 nm at an illuminance of 1000 mW/cm 2 for 10 seconds to obtain shear test samples (2d) and (3d).
  • the obtained shear test sample (3a) was heated in a small high temperature chamber (ST-120, manufactured by Espec Corporation) at 120° C. for 6 hours.
  • the adhesive joint of the heated shear test sample (3a) was irradiated with LED light having a wavelength of 365 nm at an illuminance of 1000 mW/cm 2 for 10 seconds to obtain a shear test sample (3e).
  • the shear adhesive strength of the obtained shear test samples (2a) to (2d) and (3a) to (3e) was measured at a tensile speed of 10 mm/min in an environment of 25°C using an autograph AGS-X manufactured by Shimadzu Corporation. The results are shown in Tables 2 and 3.
  • the shear test samples (1a), (2a), and (3a) corresponding to the first structure showed a significant decrease in shear adhesive strength when irradiated with light, as shown by the results of the shear test samples (1b), (2b), and (3b). This is believed to be due to photosoftening (photomelting) of the adhesive portion.
  • the shear test samples (1c), (2c), (2d), (3c), (3d), and (3e) corresponding to the second structure showed a suppressed decrease in shear adhesive strength. This is believed to be due to the volatilization of at least a portion of the photoradical generator (second photoradical generator) contained in the adhesive portion. From the above, it was confirmed that, according to the manufacturing method of the structure disclosed herein, it is possible to suppress the development of photosoftening properties in an adhesive portion containing a composition exhibiting photosoftening properties by a simple method.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Lining Or Joining Of Plastics Or The Like (AREA)
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010168452A (ja) * 2009-01-22 2010-08-05 Nippon Steel Chem Co Ltd ポリエン／ポリチオール系感光性樹脂組成物
WO2022043158A1 (en) * 2020-08-31 2022-03-03 Henkel Ag & Co. Kgaa Resin composition and cured product thereof
WO2022080405A1 (ja) * 2020-10-14 2022-04-21 昭和電工マテリアルズ株式会社 光硬化性組成物及びその硬化物、光融解性樹脂組成物、並びに接着剤セット
WO2023276773A1 (ja) * 2021-06-28 2023-01-05 ナミックス株式会社 樹脂組成物及び接着剤
WO2023167067A1 (ja) * 2022-03-01 2023-09-07 パナソニックＩｐマネジメント株式会社 硬化性組成物

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JP5453144B2 (ja) 2010-03-15 2014-03-26 東洋ゴム工業株式会社 空気ばね

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010168452A (ja) * 2009-01-22 2010-08-05 Nippon Steel Chem Co Ltd ポリエン／ポリチオール系感光性樹脂組成物
WO2022043158A1 (en) * 2020-08-31 2022-03-03 Henkel Ag & Co. Kgaa Resin composition and cured product thereof
WO2022080405A1 (ja) * 2020-10-14 2022-04-21 昭和電工マテリアルズ株式会社 光硬化性組成物及びその硬化物、光融解性樹脂組成物、並びに接着剤セット
WO2023276773A1 (ja) * 2021-06-28 2023-01-05 ナミックス株式会社 樹脂組成物及び接着剤
WO2023167067A1 (ja) * 2022-03-01 2023-09-07 パナソニックＩｐマネジメント株式会社 硬化性組成物

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