WO2023100863A1 - Couche d'agent collant et/ou couche d'adhésif - Google Patents

Couche d'agent collant et/ou couche d'adhésif Download PDF

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Publication number
WO2023100863A1
WO2023100863A1 PCT/JP2022/043960 JP2022043960W WO2023100863A1 WO 2023100863 A1 WO2023100863 A1 WO 2023100863A1 JP 2022043960 W JP2022043960 W JP 2022043960W WO 2023100863 A1 WO2023100863 A1 WO 2023100863A1
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Prior art keywords
adhesive layer
pressure
sensitive adhesive
polymer
mass
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PCT/JP2022/043960
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English (en)
Japanese (ja)
Inventor
駿 飛永
虎太朗 雨宮
大輔 水野
武史 仲野
智史 岩田
Original Assignee
日東電工株式会社
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Priority claimed from JP2022188635A external-priority patent/JP2023081330A/ja
Application filed by 日東電工株式会社 filed Critical 日東電工株式会社
Publication of WO2023100863A1 publication Critical patent/WO2023100863A1/fr

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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
    • C09J201/00—Adhesives based on unspecified macromolecular 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
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]

Definitions

  • the present invention relates to a pressure-sensitive adhesive layer and/or an adhesive layer, more specifically to a pressure-sensitive adhesive layer capable of exhibiting stickiness and/or an adhesive layer capable of exhibiting adhesiveness.
  • optical devices such as displays
  • thin and flexible displays typified by OLED are constructed by laminating a plurality of optical films and thin layer devices.
  • a device such as a pressure-sensitive sensor that requires flexibility is constructed by laminating a pressure-sensitive member and a substrate (Patent Document 1).
  • Liquid curable resins, pressure-sensitive adhesives, and adhesives are selected as interlayer fillers in these laminates.
  • An adhesive (adhesive, etc.) is preferably used.
  • the pressure-sensitive adhesive or the like has a function of dispersing and relieving the stress generated by bending/folding, especially in a flexible member, and it is said that the more flexible the pressure-sensitive adhesive or the like, the more efficiently the function is expressed (Patent Document 2) A flexible adhesive or the like is used.
  • the adhesive layer or adhesive layer has excellent handling properties before sticking or bonding to the member, and excellent flexibility during use, that is, after sticking or bonding to the member. It has been demanded.
  • the present invention is intended to solve such problems, and an object of the present invention is to provide a pressure-sensitive adhesive layer that has excellent handleability before adhesion or adhesion to a member and excellent flexibility after adhesion or adhesion to a member. and/or to provide an adhesive layer.
  • the present inventors have made diligent efforts, and as a result, according to the pressure-sensitive adhesive layer and the adhesive layer whose hardness is reduced by an external stimulus, it is excellent in handleability before sticking or bonding to a member. , it was found to be excellent in flexibility after being adhered or adhered to a member.
  • the present invention has been completed based on these findings.
  • the present invention provides a pressure-sensitive adhesive layer and/or adhesive layer whose hardness is reduced by an external stimulus. Since the pressure-sensitive adhesive layer or the adhesive layer has the property that the hardness is reduced by an external stimulus, the hardness can be made relatively high before applying the external stimulus, and the pressure-sensitive adhesive layer or the adhesive layer is used before use, i.e. Before sticking or adhering the pressure-sensitive adhesive layer or the adhesive layer to the member, it is difficult for the glue to ooze out or to be chipped, and the handleability can be excellent. On the other hand, after applying an external stimulus, the hardness can be made lower than before applying, and when using the adhesive layer or adhesive layer, that is, in the state where the adhesive layer or adhesive layer is adhered or adhered to the member It can be excellent in flexibility.
  • the hardness does not increase after the reduction.
  • Such a pressure-sensitive adhesive layer or the like does not increase in hardness in a state where the pressure-sensitive adhesive layer or the like is adhered or adhered to a member, and maintains flexibility.
  • the ratio [Young's modulus (E2)/Young's modulus (E1)] of the Young's modulus (E1) before applying the external stimulus and the Young's modulus (E2) after applying the external stimulus is preferably less than 0.95.
  • Such an adhesive layer has excellent flexibility before and after applying an external stimulus, excellent resistance to microdeformation, impact resistance, shape deformation resistance in a high speed range, step followability, adhesion, etc. is better.
  • the Young's modulus (E2) after applying an external stimulus is preferably less than 50 MPa.
  • Such a pressure-sensitive adhesive layer or the like is even more excellent in flexibility after application of an external stimulus.
  • the ratio of the breaking elongation (B1) before applying an external stimulus to the breaking elongation (B2) after applying an external stimulus [breaking elongation (B2)/breaking elongation (B1)] is preferably greater than 1.1. .
  • Such an adhesive layer or the like has excellent flexibility before and after application of an external stimulus, excellent resistance to microdeformation, and excellent impact resistance and shape deformation resistance in a high speed range.
  • the adhesive layer and the like are preferably used for optical applications.
  • the pressure-sensitive adhesive layer and/or adhesive layer of the present invention has excellent handleability before sticking or bonding to a member, and excellent flexibility after sticking or bonding to a member.
  • FIG. 1 shows a schematic cross-sectional view of a release liner-attached pressure-sensitive adhesive sheet or adhesive sheet 10 in which a pressure-sensitive adhesive layer or adhesive layer 1 of the present invention is formed on a release liner 2.
  • FIG. 1 shows a schematic cross-sectional view of a release liner-attached pressure-sensitive adhesive sheet or adhesive sheet 10 in which a pressure-sensitive adhesive layer or adhesive layer 1 of the present invention is formed on a release liner 2.
  • Adhesive layer, adhesive layer refers to the property that two surfaces adhere to each other and can be peeled off if necessary, based on the cohesive force based on the chemical structure of the composition, when external pressure is applied (e.g., microscopic pressure).
  • adhesive refers to the property of chemically reacting (curing) the composition to form a cured product, which is not intended to be peeled off, and which allows two surfaces to be firmly bonded.
  • the "adhesive layer” is a laminar adhesive layer that does not have fluidity
  • the “adhesive layer” is a laminar adhesive layer that does not have fluidity.
  • the pressure-sensitive adhesive layer and/or adhesive layer of the present invention has the property that its hardness is reduced by an external stimulus.
  • the hardness is preferably Young's modulus measured by, for example, a tensile compression tester. That is, the pressure-sensitive adhesive layer and/or adhesive layer of the present invention has the property that Young's modulus is reduced by an external stimulus.
  • the "adhesive layer and/or adhesive layer” may be referred to as "adhesive layer or the like".
  • the pressure-sensitive adhesive layer or the like of the present invention has a lower Young's modulus after applying an external stimulus than before applying an external stimulus.
  • a pressure-sensitive adhesive layer or the like is excellent in handleability before application of an external stimulus, and excellent in flexibility, impact resistance, and shape deformation resistance in a high speed range after application of an external stimulus.
  • the hardness does not increase after the reduction.
  • Such a pressure-sensitive adhesive layer or the like does not increase in hardness in a state where the pressure-sensitive adhesive layer or the like is adhered or adhered to a member, and maintains flexibility.
  • FIG. 1 is a schematic cross-sectional view of one embodiment of the pressure-sensitive adhesive layer, etc. of the present invention.
  • a pressure-sensitive adhesive layer or adhesive layer 1 shown in FIG. 1 is laminated on the release-treated surface of a release liner 2 to form a pressure-sensitive adhesive sheet or adhesive sheet 10 with a release liner.
  • the pressure-sensitive adhesive layer or the like of the present invention has a ratio of Young's modulus (E1) before application of an external stimulus to Young's modulus (E2) after application of an external stimulus [Young's modulus (E2)/Young's modulus (E1)] of 0.95. It is preferably less than (eg, 0.1 or more and less than 0.95), more preferably 0.8 or less (eg, 0.2 to 0.8), still more preferably 0.7 or less (eg, 0.3 to 0.0 .7).
  • the pressure-sensitive adhesive layer or the like is excellent in flexibility before and after application of an external stimulus, excellent in resistance to minute deformation, and more excellent in impact resistance, shape deformation resistance in a high speed range, conformability to steps, adhesion, and the like.
  • the pressure-sensitive adhesive layer, etc. of the present invention preferably has a Young's modulus (E1) of 200 MPa or less (eg, 0.03 to 200 MPa) before applying an external stimulus.
  • the pressure-sensitive adhesive layer or the like preferably has a Young's modulus (E2) of 50 MPa or less (eg, 0.001 to 50 MPa) after application of an external stimulus.
  • the pressure-sensitive adhesive layer or the like having the above Young's modulus has an appropriate hardness before application of an external stimulus, and is excellent in workability such as manufacturing/processing, storage and transportation.
  • the pressure-sensitive adhesive layer having the above Young's modulus is excellent in flexibility after application of an external stimulus, and is more excellent in step followability, adhesiveness, and the like.
  • the pressure-sensitive adhesive layer preferably has a Young's modulus (E1) of 0.03 to 1.5 MPa, more preferably 0.05 to 1.0 MPa, still more preferably 0.1 to 0 .8 MPa.
  • E1 Young's modulus
  • the pressure-sensitive adhesive layer having the above Young's modulus (E1) has appropriate hardness before application of an external stimulus and is superior in handleability.
  • the above-mentioned adhesive layer preferably has a Young's modulus (E1) of 0.1 to 200 MPa, more preferably 0.3 to 100 MPa, and still more preferably 0.5 to 20 MPa before applying an external stimulus.
  • E1 Young's modulus
  • the adhesive layer having the above Young's modulus has appropriate hardness before application of an external stimulus, and is excellent in workability such as manufacturing/processing, storage and transportation.
  • the pressure-sensitive adhesive layer preferably has a Young's modulus (E2) of less than 1.0 MPa (for example, 0.001 MPa or more and less than 1.0 MPa), more preferably 0.5 MPa or less (for example, 0.001 MPa or more and less than 1.0 MPa) after application of an external stimulus. 005 to 0.5 MPa), more preferably 0.3 MPa or less (for example, 0.01 to 0.3 MPa).
  • E2 Young's modulus of less than 1.0 MPa (for example, 0.001 MPa or more and less than 1.0 MPa), more preferably 0.5 MPa or less (for example, 0.001 MPa or more and less than 1.0 MPa) after application of an external stimulus. 005 to 0.5 MPa), more preferably 0.3 MPa or less (for example, 0.01 to 0.3 MPa).
  • the pressure-sensitive adhesive layer having the above Young's modulus (E2) has excellent flexibility after application of an external stimulus, excellent resistance to microdeformation, impact resistance, shape deformation resistance in
  • the adhesive layer preferably has a Young's modulus (E2) of 50 MPa or less (eg, 0.01 MPa or more and less than 50 MPa) after application of an external stimulus, more preferably 10 MPa or less (eg, 0.05 to 10 MPa). It is preferably 5 MPa or less (eg, 0.1 to 5 MPa).
  • E2 Young's modulus
  • the adhesive layer having the above Young's modulus is excellent in flexibility after application of an external stimulus, and is more excellent in step followability, adhesion, and the like.
  • the adhesive layer or the like of the present invention preferably has a higher breaking elongation after applying an external stimulus than before applying an external stimulus.
  • the pressure-sensitive adhesive layer or the like does not have to be broken at 500% elongation before and after applying an external stimulus.
  • Such a pressure-sensitive adhesive layer or the like is excellent in handleability before application of an external stimulus, and excellent in resistance to minute deformation, impact resistance, and shape deformation resistance in a high-speed range after application of an external stimulus.
  • the pressure-sensitive adhesive layer or the like of the present invention preferably has a breaking elongation (B1) of 100 to 2000%, more preferably 100 to 1000%, still more preferably 120 to 900%, particularly preferably 120 to 900%, before applying an external stimulus. is 150-850%.
  • the pressure-sensitive adhesive layer or the like having the above breaking elongation (B1) has appropriate hardness before application of an external stimulus, and is excellent in handleability.
  • the adhesive layer or the like of the present invention preferably has a breaking elongation (B2) after application of an external stimulus of 100 to 1300%, more preferably 130 to 1100%, still more preferably 160 to 1000%.
  • the pressure-sensitive adhesive layer or the like having the above Young's modulus (B2) is excellent in flexibility after application of an external stimulus, excellent in resistance to minute deformation, and excellent in impact resistance and shape deformation resistance in a high speed range.
  • the ratio of the breaking elongation (B1) before applying an external stimulus to the breaking elongation (B2) after applying an external stimulus [breaking elongation (B2)/breaking elongation (B1)] is , preferably greater than 1.1 (eg, greater than 1.1 and 2.0 or less), more preferably 1.2 or greater (eg, 1.2 to 1.8), and still more preferably 1.3 or greater (eg, 1 .3 to 1.6).
  • the pressure-sensitive adhesive layer or the like is excellent in flexibility before and after application of an external stimulus, excellent in resistance to minute deformation, and excellent in impact resistance and shape deformation resistance in a high speed range.
  • the pressure-sensitive adhesive layer and the like of the present invention have the property that their hardness is reduced by an external stimulus.
  • the pressure-sensitive adhesive layer or the like having such properties include a pressure-sensitive adhesive layer or the like containing a polymer having a degradable bond in the molecule that is cleaved by an external stimulus.
  • the above polymer may contain only one type, or may contain two or more types.
  • a polymer having a degradable bond that can be cleaved by an external stimulus in its molecule may be referred to as "polymer (A)".
  • the degradable bond may be of only one type, or may be of two or more types.
  • Degradable bonds in the polymer (A) include bonds that can be cleaved by an external stimulus and then recombined (reversible degradable bonds) and bonds that are cleaved by an external stimulus and then not recombined (irreversible bonds). degradable bond).
  • the pressure-sensitive adhesive layer or the like of the present invention further contains a compound that suppresses recombination.
  • polymer (A1) the polymer having the irreversible degradable bond in the molecule
  • polymer (A2) the polymer having the irreversible degradable bond in the molecule
  • a compound that suppresses recombination is sometimes referred to as a “recombination-suppressing compound (B)".
  • the external stimulus is appropriately selected according to the hardness reduction means, and includes active energy ray irradiation, heat, and the like.
  • the polymer (A) is a thermosetting resin or an active energy ray-curable resin
  • the polymer ( It is preferably an external stimulus that is different from the type of curability when A) has curability.
  • the external stimulus is preferably active energy ray irradiation when the polymer (A) is a thermosetting resin, and preferably heat when the polymer (A) is an active energy ray-curable resin.
  • the active energy rays are not particularly limited, but include ionizing radiation such as ⁇ -rays, ⁇ -rays, ⁇ -rays, neutron beams and electron beams, ultraviolet light and visible light. Ultraviolet rays are particularly preferred.
  • the irradiation energy, irradiation time, irradiation method, etc. of the active energy ray are not particularly limited. Examples of light sources for ultraviolet light or visible light irradiation include low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, metal halide lamps, and LED lamps.
  • a known or commonly used bond can be applied, preferably a bond that is cleaved as a radical, particularly preferably a disulfide bond (-SS-).
  • the irreversibly degradable bond in the polymer (A2) a known or commonly used bond can be applied, preferably a bond containing a nitrobenzyl group.
  • the bond containing the nitrobenzyl group is preferably an ester bond formed by nitrobenzyl alcohol (preferably 2-nitrobenzyl alcohol) and a carboxylic acid having a polymerizable functional group.
  • thermoplastic resins examples include thermoplastic resins, thermosetting resins, and active energy ray-curable resins. Among them, thermoplastic resins and thermosetting resins are preferred.
  • a pressure-sensitive adhesive layer or the like containing a thermoplastic resin is capable of exerting adhesiveness such that it adheres under pressure from the outside, for example.
  • a pressure-sensitive adhesive layer or the like containing a thermosetting resin can be adhered to an adherend by being cured by heating, for example.
  • thermosetting resin examples include both resins having thermosetting properties (thermosetting resins) and resins obtained by curing the above thermosetting resins.
  • the thermosetting resin has a thermosetting functional group.
  • the number of thermosetting functional groups in the thermosetting resin is preferably 2 or more (for example, 2 to 4).
  • thermosetting resin examples include phenol-based resin, epoxy-based resin, urethane-based resin, melamine-based resin, and alkyd-based resin.
  • thermoplastic resin examples include polystyrene-based resin, vinyl acetate-based resin, polyester-based resin, polyolefin-based resin (polyethylene-based resin, polypropylene-based resin composition, etc.), polyimide-based resin, acrylic-based resin, and the like.
  • acrylic resins are preferable because they can impart cohesion and appropriate flexibility to the pressure-sensitive adhesive layer and the like.
  • acrylic resin designs There are various types of acrylic resin designs depending on the purpose. Accordingly, it is preferable to appropriately select the monomer species, copolymerization composition ratio, molecular weight, molecular weight distribution, cross-linking agent, compounding composition ratio, and the like.
  • An acrylic resin is a resin containing an acrylic monomer (a monomer having a (meth)acryloyl group in the molecule) as a monomer component that constitutes the resin. That is, the acrylic resin contains structural units derived from acrylic monomers.
  • the acrylic resin is preferably a polymer containing a (meth)acrylic acid alkyl ester as a monomer component constituting the polymer.
  • (meth)acrylic means “acrylic” and/or “methacrylic” (one or both of "acrylic” and “methacrylic"), and the same applies to others. .
  • a (meth)acrylic acid alkyl ester having a linear or branched alkyl group is preferably mentioned.
  • 1 type may be used for the said (meth)acrylic-acid alkyl ester, and 2 or more types may be used for it.
  • the (meth)acrylic acid alkyl ester having a linear or branched alkyl group is not particularly limited, but examples include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, Isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, s-butyl (meth) acrylate, t-butyl (meth) acrylate, pentyl (meth) acrylate, (meth) ) isopentyl acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isooctyl (meth)acrylate, nonyl (meth)acrylate, ( meth) isononyl acrylate, decyl
  • (meth)acrylic acid alkyl ester having a linear or branched alkyl group among them, a linear or branched chain having 2 or more carbon atoms (preferably 2 to 18, more preferably 2 to 5) A (meth)acrylic acid alkyl ester having a triangular alkyl group is preferred.
  • the content of structural units derived from (meth)acrylic acid alkyl ester in the acrylic resin is preferably 70% by mass or more, more preferably 100% by mass, based on the total amount of the monomer components constituting the acrylic resin. It is 80% by mass or more. The above content is preferably 99% by mass or less, more preferably 98% by mass or less. Of course, depending on the application and required properties, the content ratio of the structural unit derived from the (meth)acrylic acid alkyl ester in the acrylic resin may be and may be less than 70% by mass.
  • the acrylic resin contains the (meth)acrylic acid alkyl ester and other monomers (copolymerizable monomers) copolymerizable with the (meth)acrylic acid alkyl ester as monomer components constituting the resin. good too. That is, the acrylic resin may contain a copolymerizable monomer as a structural unit.
  • the above copolymerizable monomers may be used alone or in combination of two or more.
  • Examples of the copolymerizable monomer include carboxy group-containing monomers, hydroxy group-containing monomers, epoxy group-containing monomers, keto group-containing monomers, alkoxy group-containing monomers, sulfonic acid group-containing monomers, phosphoric acid group-containing monomers, vinyl ester-based monomers, vinyl ether-based monomers, isocyanate group-containing monomers, aromatic vinyl compounds, alicyclic monomers, aromatic ring-containing (meth)acrylates, chlorine-containing monomers, nitrogen-containing monomers, and the like.
  • the content of structural units derived from copolymerizable monomers in the acrylic resin is preferably 0.1% by mass or more, more preferably 0%, based on the total amount of 100% by mass of the monomer components constituting the acrylic resin. .3% by mass or more.
  • the above content is preferably 30% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less.
  • the content ratio of the structural units derived from the copolymerizable monomer in the acrylic resin may be It may be less than 0.1% by mass.
  • the polymer (A) preferably forms a network structure.
  • a network structure refers to a state in which molecules are entangled with each other, or a state in which molecular chains form a long molecule through some bond. That is, the polymer (A) is preferably a polymer in which a network structure is formed by bonding or entanglement between molecules.
  • a pressure-sensitive adhesive layer or the like having such a structure forms a network structure through polymer-to-polymer bonding or polymer-to-polymer entanglement, and can have an appropriate degree of hardness. , the polymer structure is shredded and the flexibility is improved.
  • Micromolecules are entangled with each other refers to the state in which macromolecules form a network structure without covalent bonds. In order to form such an entangled structure, it is preferable to contain different types of polymers that are unlikely to cause a cross-linking reaction with each other. are preferably intertwined to form a structure. Such a configuration is suitable for an adhesive layer or the like that is relatively soft before application of an external stimulus because no covalent bond is involved.
  • the state in which the molecular chains form a long molecule through some kind of bond means that the polymer is a single macromolecular polymer.
  • a relatively hard adhesive layer can be formed. Suitable for adhesive layers with different properties.
  • the polymer (A1) is preferably a thermosetting resin.
  • the polymer (A1) which is a thermosetting resin, may be a resin in which a thermosetting resin and a thermoplastic resin are entangled to form a network structure.
  • Epoxy resin is preferable as the thermosetting resin.
  • the epoxy-based resin is a resin containing at least an epoxy-based monomer and a compound (a1) described later as a monomer component constituting the resin, and/or a compound (a1) is It is preferable to use a resin in which epoxy-based resins are cross-linked by acting as a cross-linking agent.
  • An acrylic resin is preferable as the thermoplastic resin.
  • crosslinking agent refers to a compound capable of forming crosslinks of a resin, and is sometimes referred to as a "curing agent".
  • the polymer (A2) is preferably a thermoplastic resin, more preferably an acrylic resin.
  • the acrylic resin is preferably a resin containing at least an acrylic monomer and a compound (a2) described below as monomer components constituting the resin.
  • the content of the thermosetting resin is not particularly limited. From the viewpoint of imparting hardness, it is preferably 3 to 95% by mass, more preferably 5 to 90% by mass, and still more preferably 6 to 85% by mass with respect to 100% by mass of the total amount of the adhesive layer of the present invention. is.
  • the content is preferably 50 to 95% by mass, more preferably 60 to 90% by mass, and still more preferably 65 to 85% by mass. be.
  • the content is preferably 3 to 80% by mass, more preferably 5 to 50% by mass, and still more preferably 6 to 30% by mass.
  • the amount of the thermosetting resin includes the amount of the thermosetting resin, its raw material monomer, the cross-linking agent, and the structural part derived from the cross-linking agent.
  • the content ratio of the thermoplastic resin is not particularly limited, but the pressure-sensitive adhesive layer or the like is provided with appropriate initial hardness and hardness after external stimulation. Therefore, it is preferably 50% by mass or more, more preferably 70% by mass or more, based on 100% by mass of the total amount of the pressure-sensitive adhesive layer and the like of the present invention.
  • the amount of the thermoplastic resin includes the amount of the thermoplastic resin, its raw material monomers, the cross-linking agent, and the structural portion derived from the cross-linking agent.
  • the content of the thermoplastic resin is 20 to 97% by mass with respect to 100% by mass of the total amount of the adhesive layer or the like of the present invention. is preferred, more preferably 50 to 95% by mass, and still more preferably 70 to 93% by mass.
  • the adhesive layer or the like of the present invention contains a thermosetting resin as a base polymer, the content is preferably 30% by mass or less, and may be 10% by mass or less, 5% by mass or less, or 1% by mass or less. , 0% by mass.
  • the content of the thermoplastic resin is 50% by mass or more with respect to 100% by mass of the total amount of the pressure-sensitive adhesive layer or the like of the present invention. It is preferably 70% by mass or more, still more preferably 80% by mass or more, and particularly preferably 90% by mass or more.
  • the pressure-sensitive adhesive layer, etc. of the present invention preferably has a shear storage modulus (G') that is reduced by an external stimulus (especially active energy ray irradiation).
  • G' shear storage modulus
  • Such a pressure-sensitive adhesive layer or the like is improved in flexibility by an external stimulus.
  • the shear storage modulus (G') does not increase after the decrease.
  • the pressure-sensitive adhesive layer or the like of the present invention preferably has a shear storage modulus (G') at 25° C. before application of an external stimulus of 1.0 ⁇ 10 3 to 1.0 ⁇ 10 8 Pa, more preferably 1.0 ⁇ 10 4 to 1.0 ⁇ 10 7 Pa, more preferably 1.0 ⁇ 10 4 to 1.0 ⁇ 10 6 Pa, particularly preferably 2.0 ⁇ 10 4 to 1.0 ⁇ 10 5 Pa is.
  • G' shear storage modulus
  • the pressure-sensitive adhesive layer having the shear storage elastic modulus described above has appropriate hardness before application of an external stimulus, and is excellent in handleability.
  • the pressure-sensitive adhesive layer, etc. of the present invention preferably has a shear storage modulus (G') at 50° C. before application of an external stimulus of 1.0 ⁇ 10 3 to 5.0 ⁇ 10 7 Pa, more preferably 7.0 ⁇ 10 3 to 1.0 ⁇ 10 6 Pa, more preferably 1.0 ⁇ 10 4 to 1.0 ⁇ 10 5 Pa.
  • G' shear storage modulus
  • the pressure-sensitive adhesive layer or the like having the above-mentioned shear storage modulus has appropriate hardness before application of an external stimulus and is excellent in handleability even when the temperature is slightly increased due to the environment.
  • the pressure-sensitive adhesive layer, etc. of the present invention preferably has a shear storage modulus (G') at 85° C. before application of an external stimulus of 1.0 ⁇ 10 2 to 1.0 ⁇ 10 6 Pa, more preferably 1.0 ⁇ 10 3 to 1.0 ⁇ 10 5 Pa, more preferably 5.0 ⁇ 10 3 to 1.0 ⁇ 10 5 Pa.
  • G' shear storage modulus
  • the pressure-sensitive adhesive layer or the like having the above-mentioned shear storage modulus has appropriate hardness before application of an external stimulus even when applied in a high-temperature environment, for example, and is excellent in handleability.
  • the pressure-sensitive adhesive layer, etc. of the present invention preferably has a shear storage modulus (G') at 25° C. after application of an external stimulus of 1.0 ⁇ 10 2 to 5.0 ⁇ 10 6 Pa, more preferably 1.0 ⁇ 10 3 to 5.0 ⁇ 10 5 Pa, more preferably 3.0 ⁇ 10 3 to 1.0 ⁇ 10 5 Pa, particularly preferably 5.0 ⁇ 10 3 to 5.0 ⁇ 10 4 Pa is.
  • G' shear storage modulus
  • the pressure-sensitive adhesive layer or the like of the present invention is more excellent in flexibility after application of an external stimulus, and is more excellent in step followability, adhesiveness, and the like.
  • the pressure-sensitive adhesive layer, etc. of the present invention preferably has a shear storage modulus (G') at 50° C. after application of an external stimulus of 1.0 ⁇ 10 2 to 1.0 ⁇ 10 6 Pa, more preferably 5.0 ⁇ 10 2 to 3.0 ⁇ 10 5 Pa, more preferably 1.0 ⁇ 10 3 to 1.0 ⁇ 10 5 Pa, particularly preferably 2.0 ⁇ 10 3 to 8.0 ⁇ 10 4 Pa is.
  • G' shear storage modulus
  • the shear storage elastic modulus is within the above range, after application of an external stimulus, for example, when the temperature is slightly increased due to the environment, the flexibility, step conformability, adhesion, etc. are superior.
  • the pressure-sensitive adhesive layer, etc. of the present invention preferably has a shear storage modulus (G') at 85° C. after application of an external stimulus of 1.0 ⁇ 10 2 to 8.0 ⁇ 10 5 Pa, more preferably 3.0 ⁇ 10 2 to 1.0 ⁇ 10 5 Pa, more preferably 5.0 ⁇ 10 2 to 1.0 ⁇ 10 5 Pa, particularly preferably 1.0 ⁇ 10 2 to 7.0 ⁇ 10 4 Pa is.
  • G' shear storage modulus
  • the shear storage elastic modulus is within the above range, after application of an external stimulus, for example, when subjected to a high-temperature environment, the film is more excellent in flexibility, step followability, adhesion, and the like.
  • the pressure-sensitive adhesive layer, etc. of the present invention has a ratio of the shear storage modulus (G') at 25°C before applying an external stimulus to the shear storage modulus (G') at 25°C after applying an external stimulus [after applying an external stimulus / before application of external stimulus] is preferably less than 0.95 (eg, 0.01 or more and less than 0.95), more preferably 0.8 or less (eg, 0.05 to 0.8), still more preferably 0.7 or less (eg 0.1 to 0.7), particularly preferably 0.6 or less (eg 0.2 to 0.6).
  • 0.95 eg, 0.01 or more and less than 0.95
  • more 0.8 or less eg, 0.05 to 0.8
  • still more preferably 0.7 or less eg 0.1 to 0.7
  • particularly preferably 0.6 or less eg 0.2 to 0.6
  • the pressure-sensitive adhesive layer, etc. of the present invention has a ratio of the shear storage modulus (G') at 50 ° C. before applying an external stimulus to the shear storage modulus (G') at 50 ° C. after applying an external stimulus [after applying an external stimulus / before application of external stimulus] is preferably less than 0.95 (eg, 0.01 or more and less than 0.95), more preferably 0.8 or less (eg, 0.05 to 0.8), still more preferably 0.7 or less (eg 0.1 to 0.7), particularly preferably 0.6 or less (eg 0.2 to 0.6).
  • 0.95 eg, 0.01 or more and less than 0.95
  • more 0.8 or less eg, 0.05 to 0.8
  • still more preferably 0.7 or less eg 0.1 to 0.7
  • particularly preferably 0.6 or less eg 0.2 to 0.6
  • the pressure-sensitive adhesive layer, etc. of the present invention has a ratio of the shear storage modulus (G') at 85°C before applying an external stimulus to the shear storage modulus (G') at 85°C after applying an external stimulus [after applying an external stimulus / before application of external stimulus] is preferably less than 0.95 (eg, 0.01 or more and less than 0.95), more preferably 0.8 or less (eg, 0.05 to 0.8), still more preferably 0.7 or less (eg 0.1 to 0.7), particularly preferably 0.6 or less (eg 0.2 to 0.6).
  • 0.95 eg, 0.01 or more and less than 0.95
  • more 0.8 or less eg, 0.05 to 0.8
  • still more preferably 0.7 or less eg 0.1 to 0.7
  • particularly preferably 0.6 or less eg 0.2 to 0.6
  • the pressure-sensitive adhesive layer, etc. of the present invention have the property of reducing stress due to an external stimulus.
  • the stress does not increase after reduction.
  • Such a pressure-sensitive adhesive layer or the like does not increase stress in a state in which the pressure-sensitive adhesive layer or the like is adhered or adhered to a member, and maintains its flexibility.
  • the stress examples include the stress (distortion stress) when pulled at an arbitrary magnification, which is measured by a tension/compression tester.
  • the stress (distortion stress) when pulled at the above-mentioned specific magnification may be reduced as long as the stress (distortion stress) when pulled at at least one magnification is reduced.
  • the strain stress at at least one of the tensile ratios of 100 to 500% is reduced, and the strain at one or more tensile ratios selected from the group consisting of 100%, 200%, 300%, and 500%.
  • a reduction in stress is particularly preferred. Preferred ranges of stress at each tensile magnification are described below, and these values are preferred ranges when no breakage occurs at each tensile magnification.
  • the pressure-sensitive adhesive layer, etc. of the present invention has a ratio [ S2(100)/S1(100)] is preferably less than 0.95 (for example, 0.1 or more and less than 0.95), more preferably 0.9 or less, still more preferably 0.8 or less .
  • Such an adhesive layer or the like shows that the relatively weak tensile stress is further reduced by applying an external stimulus, and the repulsive force when pulled is low, making it suitable for relatively low load applications such as foldable members. .
  • the pressure-sensitive adhesive layer or the like of the present invention preferably has a stress (100% strain stress) (S1(100)) before application of an external stimulus of 0.01 MPa or more (for example, 0.01 to 10 MPa), more preferably It is 0.03 MPa or more (eg, 0.03 to 6 MPa), more preferably 0.05 MPa or more (eg, 0.05 to 3 MPa).
  • a stress (100% strain stress) S1(100)
  • S1(100) stress (100% strain stress) before application of an external stimulus of 0.01 MPa or more (for example, 0.01 to 10 MPa), more preferably It is 0.03 MPa or more (eg, 0.03 to 6 MPa), more preferably 0.05 MPa or more (eg, 0.05 to 3 MPa).
  • Such a pressure-sensitive adhesive layer or the like is even more excellent in flexibility after application of an external stimulus.
  • the pressure-sensitive adhesive layer or the like of the present invention preferably has a stress (100% strain stress) (S2(100)) after application of an external stimulus of 10 MPa or less (eg, 0.01 to 10 MPa), more preferably 6 MPa or less. (eg, 0.02 to 6 MPa), more preferably 3 MPa or less (eg, 0.03 to 3 MPa).
  • a stress (100% strain stress) S2(100)
  • 10 MPa or less eg, 0.01 to 10 MPa
  • 6 MPa or less eg, 0.02 to 6 MPa
  • 3 MPa or less eg, 0.03 to 3 MPa
  • the pressure-sensitive adhesive layer, etc. of the present invention has a ratio [ S2(200)/S1(200)] is preferably less than 0.95 (for example, 0.1 or more and less than 0.95), more preferably 0.8 or less, still more preferably 0.7 or less .
  • a pressure-sensitive adhesive layer or the like shows that the relatively weak tensile stress is further reduced by applying an external stimulus, has a low repulsive force when pulled, and is suitable for relatively low-load applications such as foldable members. .
  • the pressure-sensitive adhesive layer or the like of the present invention preferably has a stress (200% strain stress) (S1(200)) before application of an external stimulus of 0.03 MPa or more (eg, 0.03 to 10 MPa), more preferably It is 0.04 MPa or more (eg, 0.04 to 4 MPa), more preferably 0.06 MPa or more (eg, 0.06 to 2 MPa).
  • a stress (200% strain stress) S1(200)
  • S1(200) stress (200% strain stress) before application of an external stimulus of 0.03 MPa or more (eg, 0.03 to 10 MPa), more preferably It is 0.04 MPa or more (eg, 0.04 to 4 MPa), more preferably 0.06 MPa or more (eg, 0.06 to 2 MPa).
  • Such a pressure-sensitive adhesive layer or the like is even more excellent in flexibility after application of an external stimulus.
  • the pressure-sensitive adhesive layer or the like of the present invention preferably has a stress (200% strain stress) (S2(200)) after application of an external stimulus of 10 MPa or less (eg, 0.01 to 10 MPa), more preferably 4 MPa or less. (eg, 0.03 to 4 MPa), more preferably 2 MPa or less (eg, 0.04 to 2 MPa).
  • S2(200) stress (200% strain stress
  • Such a pressure-sensitive adhesive layer or the like is even more excellent in flexibility after application of an external stimulus.
  • the pressure-sensitive adhesive layer, etc. of the present invention has a ratio [ S2(300)/S1(300)] is preferably less than 0.950 (for example, 0.1 or more and less than 0.950), more preferably 0.8 or less, still more preferably 0.7 or less .
  • a pressure-sensitive adhesive layer or the like shows that the tensile stress is reduced by applying an external stimulus, and is suitable for relatively low-load applications such as foldable members.
  • the pressure-sensitive adhesive layer or the like of the present invention preferably has a stress (300% strain stress) (S1(300)) before application of an external stimulus of 0.03 MPa or more (eg, 0.03 to 10 MPa), more preferably It is 0.05 MPa or more (eg, 0.05 to 4 MPa), more preferably 0.07 MPa or more (eg, 0.07 to 2 MPa).
  • a stress-sensitive adhesive layer or the like is even more excellent in flexibility after application of an external stimulus.
  • the pressure-sensitive adhesive layer or the like of the present invention preferably has a stress (300% strain stress) (S2(300)) of 10 MPa or less (eg, 0.01 to 10 MPa) after application of an external stimulus, more preferably 4 MPa or less. (eg, 0.03 to 4 MPa), more preferably 2 MPa or less (eg, 0.04 to 2 MPa).
  • S2(300) stress (300% strain stress)
  • 10 MPa or less eg, 0.01 to 10 MPa
  • 4 MPa or less eg, 0.03 to 4 MPa
  • 2 MPa or less eg, 0.04 to 2 MPa
  • the pressure-sensitive adhesive layer or the like has a ratio [S2 ( 500)/S1(500)] is preferably less than 0.950 (for example, 0.1 or more and less than 0.950), more preferably 0.8 or less, still more preferably 0.7 or less.
  • Such an adhesive layer or the like shows that a relatively strong tensile stress is reduced by the application of an external stimulus, and has a low repulsive force when pulled, and can be used as a folding type (especially a winding type such as a rollable) member. Suitable for relatively high load applications.
  • the pressure-sensitive adhesive layer or the like of the present invention preferably has a stress (500% strain stress) (S1(500)) before application of an external stimulus of 0.05 MPa or more (for example, 0.05 to 10 MPa), more preferably It is 0.07 MPa or more (eg, 0.07 to 4 MPa), more preferably 0.1 MPa or more (eg, 0.1 to 2 MPa).
  • a stress-sensitive adhesive layer or the like is even more excellent in flexibility after application of an external stimulus.
  • the pressure-sensitive adhesive layer or the like of the present invention preferably has a stress (500% strain stress) (S2(500)) of 10 MPa or less (eg, 0.01 to 10 MPa) after application of an external stimulus, more preferably 4 MPa or less. (eg, 0.03 to 4 MPa), more preferably 2 MPa or less (eg, 0.04 to 2 MPa).
  • S2(500) stress (500% strain stress)
  • Such a pressure-sensitive adhesive layer or the like is even more excellent in flexibility after application of an external stimulus.
  • the pressure-sensitive adhesive layer and the like of the present invention may have the property of reducing the peak strength (stress peak strength) in the stress-strain curve and the stress at break due to an external stimulus.
  • the pressure-sensitive adhesive layer or the like of the present invention preferably has a peak strength (stress peak strength) in a strain curve (stress at break if broken) of 0.07 MPa or more, more preferably, before applying an external stimulus. It is 0.1 MPa or more, more preferably 0.2 MPa or more. When the stress peak strength is 0.07 MPa or more, the pressure-sensitive adhesive layer or the like has appropriate hardness before application of an external stimulus, and is excellent in handleability.
  • the pressure-sensitive adhesive layer or the like of the present invention preferably has a peak strength (stress peak strength) in a stress-strain curve (stress at break when breaking) of 0.01 to 1.0 MPa after application of an external stimulus. More preferably 0.03 to 0.8 MPa, still more preferably 0.04 to 0.5 MPa.
  • stress peak intensity is within the above range, the flexibility, step conformability, adhesion, etc. are more excellent after application of an external stimulus.
  • the pressure-sensitive adhesive layer or the like of the present invention is the stress before applying an external stimulus - the peak strength in the strain curve and the stress after applying the external stimulus - the ratio of the peak strength in the strain curve (when breaking, the ratio of the stress at break) [external After application of stimulus/before application of external stimulus] is preferably less than 0.95 (eg, 0.05 or more and less than 0.95), more preferably 0.8 or less (eg, 0.1 to 0.8), More preferably, it is 0.7 or less (eg, 0.3 to 0.7). In this case, there is a tendency that the flexibility, step followability, and adhesion of the pressure-sensitive adhesive layer, etc., change more significantly before and after the application of the external stimulus.
  • the thickness of the pressure-sensitive adhesive layer of the present invention is not particularly limited, it is, for example, about 5 to 250 ⁇ m, more preferably 7 to 200 ⁇ m, even more preferably 10 to 100 ⁇ m, particularly preferably 10 to 50 ⁇ m.
  • the polymer (A) can be obtained using a compound (sometimes referred to as "compound (a)") capable of introducing the degradable bond into the polymer.
  • the compound (a) includes, for example, a monomer component, an oligomer component, a cross-linking agent, and the like having the decomposable bond. That is, the polymer (A) may contain a structural unit derived from a monomer component and/or an oligomer component having a degradable bond, and may contain a structural portion derived from the cross-linking agent.
  • the polymer (A) having the decomposable bond is obtained by polymerizing the above monomer component or oligomer component or copolymerizing it with another monomer component. Only one kind of the compound (a) may be used, or two or more kinds thereof may be used.
  • the decomposable bond may be present in the portion constituting the side chain in the polymer (A), or may be present in the portion constituting the main chain. good.
  • the side chain is present in the portion constituting the side chain, it is preferable from the viewpoint that stress is less likely to be applied when it is greatly deformed, and the handleability in the actual use temperature range (assuming room temperature) is maintained.
  • the molecular weight of the polymer is further reduced after the degradable bond is cleaved, the flexibility is further improved, and a large change in physical properties can be exhibited.
  • the compound (a) preferably has a functional group (functional group (L1)) other than the decomposable bond.
  • a functional group (functional group (L1)) when having two or more functional groups (L1), the compound (a) functions as a cross-linking agent.
  • the functional group (L1) is a polymerizable functional group, the compound (a) functions as a monomer component or an oligomer component.
  • polymerizable functional groups examples include cationic polymerizable groups, anionic polymerizable groups, and radically polymerizable groups. Among them, a radically polymerizable group is preferred.
  • radically polymerizable group examples include radically polymerizable carbon-carbon double bonds such as (meth)acryloyl group and vinyl group.
  • a thiol group, a carboxyl group, a hydroxy group, an amino group, an epoxy group, and isocyanate are used from the viewpoint of securing a certain degree of flexibility of the pressure-sensitive adhesive layer with an appropriate crosslinking density. and the like.
  • the number of functional groups of the compound (a) increases the molecular weight of the polymer (A) after introduction into the polymer (A), giving the polymer a certain degree of hardness before applying an external stimulus, while reducing the molecular weight of the polymer after cleavage to make it flexible. From the viewpoint of exhibiting properties, the number is preferably two or more. On the other hand, if the number of functional groups increases, it will crosslink with a large number of polymers, making it difficult to obtain the effect of cleaving the degradable bond. , the number of functional groups is preferably 4 or less, more preferably 3 or less.
  • Examples of the compound (a) having a reversible degradable bond include compounds having a disulfide bond.
  • Examples of the compound having a disulfide bond include 4,4'-dithiodibutyric acid, 4,4'-dithiodiphenol (bis(4-hydroxyphenyl)disulfide), 2,2'-dithiodianiline, 4,4' -dithiodianiline, 3,3'-dithiodipropionic acid, dithiodiethanol and the like.
  • 4,4'-dithiodibutyric acid, 4,4'-dithiodiphenol, and 4,4'-dithiodianiline are particularly preferred from the viewpoint of better solubility.
  • the compound (a1) preferably does not have an aromatic ring from the viewpoint of suppressing coloration of the pressure-sensitive adhesive layer or the like over time.
  • one having an aromatic ring may be preferable when adjusting other properties such as refractive index.
  • compound (a2) As the compound (a) having an irreversible bond (sometimes referred to as "compound (a2)"), a monomer in which a nitrobenzyl group and a polymerizable functional group are bonded via a linking group (nitrobenzyl monomer) are preferred.
  • the linking group is not particularly limited, an ester bond is preferable.
  • a nitrobenzyl-based monomer in which the linking group is an ester bond is sometimes referred to as a "nitrobenzyl ester-based monomer.”
  • the nitrobenzyl ester-based monomers include, for example, an esterified product of a compound having a nitrobenzyl alcohol skeleton and a compound having a polymerizable functional group and a carboxy group, or a compound having a nitrophenylacetic acid skeleton and a polymerizable functional group and a hydroxy group.
  • Examples include esterified products with compounds having
  • Examples of compounds having a nitrobenzyl alcohol skeleton include 2-nitrobenzyl alcohol and 2-nitro-1,3-bis(hydroxymethyl)benzene.
  • Examples of compounds having a nitrophenylacetic acid skeleton include 2-nitroisophthalic acid.
  • As the nitrobenzyl ester-based monomer 2-nitro-1,3-bis((meth)acryloyloxymethylene)benzene is preferred.
  • the nitrobenzyl ester-based monomer is a carboxylic acid having a polymerizable functional group (e.g. (meth) acrylic acid) and a compound having a nitrobenzyl alcohol skeleton to esterify, a compound having a polymerizable functional group and a hydroxy group and a compound having a nitrophenylacetic acid skeleton can be esterified.
  • a polymerizable functional group e.g. (meth) acrylic acid
  • a compound having a nitrobenzyl alcohol skeleton to esterify e.g. (meth)
  • the content of the polymer (A) in the adhesive layer or the like of the present invention is preferably 50% by mass or more, more preferably 60% by mass or more, and further It is preferably 65% by mass or more, particularly preferably 70% by mass or more.
  • the amount of the polymer (A) includes the amount of the polymer (A), its raw material monomer, the cross-linking agent, and the structural part derived from the cross-linking agent.
  • the content of the polymer (A1) in the pressure-sensitive adhesive layer or the like of the present invention is It is preferably 30 to 99% by mass, more preferably 40 to 97% by mass, even more preferably 50 to 95% by mass, and particularly preferably 70 to 95% by mass.
  • the content is 30% by mass or more, it is easy to impart adhesiveness to the pressure-sensitive adhesive layer and the like.
  • the content is 99% by mass or less, it is easy to design the composition by blending the cross-linking agent and the recombination-inhibiting compound (B).
  • the amount of the polymer (A1) includes the amount of the polymer (A1), its raw material monomer, the cross-linking agent, and the structural portion derived from the cross-linking agent.
  • the content of the polymer (A2) in the pressure-sensitive adhesive layer or the like of the present invention is It is preferably 50% by mass or more, more preferably 70% by mass or more, still more preferably 80% by mass or more, and particularly preferably 90% by mass or more.
  • the amount of the polymer (A2) includes the amount of the polymer (A2), its raw material monomer, the cross-linking agent, and the structural part derived from the cross-linking agent.
  • the content ratio of one or more selected from the group consisting of structural units derived from the compound (a1) and structural units derived from the compound (a1) in the polymer (A1) is cleaved and shredded after application of an external stimulus. From the viewpoint of exhibiting sufficient flexibility, it is preferably 0.5% by mass or more, more preferably 1.0% by mass or more, and still more preferably 1.5% by mass with respect to 100% by mass of the total amount of the polymer (A1). % by mass or more. Moreover, in order to make the crosslink density appropriate and to impart appropriate flexibility to the resin before applying an external stimulus, it is preferably 50% by mass or less, more preferably 30% by mass or less, and even more preferably 20% by mass or less. In addition, in this specification, when two or more types of polymers are entangled, the entangled polymer is converted into one polymer.
  • the content of the cross-linking agent in the pressure-sensitive adhesive layer or the like of the present invention and/or the structural portion derived from the cross-linking agent is the total amount of the polymer (A1) of 100 mass. %, preferably 0.5 to 40% by mass, more preferably 1 to 35% by mass, still more preferably 1.5 to 30% by mass.
  • the compound (a1) is a cross-linking agent
  • the content includes the amount of the compound (a1) and the structural portion derived from the compound (a1).
  • the content ratio of one or more selected from the group consisting of structural units derived from the compound (a2) and structural units derived from the compound (a2) in the polymer (A2) is cleaved and shredded after application of an external stimulus.
  • the polymer (A2) is preferably 0.1 to 15% by mass, more preferably 0.2 to 10% by mass, and still more preferably 0 .5 to 5% by weight, particularly preferably 1 to 3% by weight.
  • the content of the cross-linking agent in the pressure-sensitive adhesive layer or the like of the present invention and/or the structural portion derived from the cross-linking agent is the total amount of the polymer (A2) of 100 mass. %, preferably 0.1 to 15% by mass, more preferably 0.2 to 10% by mass, still more preferably 0.5 to 5% by mass, and particularly preferably 1 to 3% by mass.
  • the compound (a2) is a cross-linking agent
  • the content includes the amount of the compound (a2) and the structural portion derived from the compound (a2).
  • the recombination-inhibiting compound (B) is a compound capable of suppressing recombination of cleavage of the polymer (A1) caused by an external stimulus, and is not particularly limited, but when the cleavage of the polymer (A1) generates a radical , a compound having radical scavenging ability (radical scavenger) is preferred.
  • a compound having radical scavenging ability include photoradical polymerization initiators, spin scavengers, antioxidants, polymerization inhibitors, and hydrogen donors.
  • photoradical polymerization initiator examples include, but are not limited to, benzoin ether-based photopolymerization initiators, acetophenone-based photopolymerization initiators, ⁇ -ketol-based photopolymerization initiators, aromatic sulfonyl chloride-based photopolymerization initiators, Photoactive oxime photoinitiators, benzoin photoinitiators, benzyl photoinitiators, benzophenone photoinitiators, ketal photoinitiators, thioxanthone photoinitiators, acylphosphine oxide photoinitiators initiators, and the like.
  • benzoin ether-based photopolymerization initiator examples include benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 2,2-dimethoxy-1,2-diphenylethan-1-one, anisole methyl ether and the like.
  • acetophenone-based photopolymerization initiator examples include 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1-hydroxycyclohexylphenylketone, 4-phenoxydichloroacetophenone, 4-(t-butyl ) and dichloroacetophenone.
  • Examples of the ⁇ -ketol photopolymerization initiator include 2-methyl-2-hydroxypropiophenone, 1-[4-(2-hydroxyethyl)phenyl]-2-methylpropan-1-one, and the like. be done.
  • Examples of the aromatic sulfonyl chloride photopolymerization initiator include 2-naphthalenesulfonyl chloride.
  • Examples of the photoactive oxime-based photopolymerization initiator include 1-phenyl-1,1-propanedione-2-(o-ethoxycarbonyl)-oxime.
  • Examples of the benzoin-based photopolymerization initiator include benzoin.
  • Examples of the benzyl-based photopolymerization initiator include benzyl.
  • benzophenone-based photopolymerization initiator examples include benzophenone, benzoylbenzoic acid, 3,3'-dimethyl-4-methoxybenzophenone, polyvinylbenzophenone, and ⁇ -hydroxycyclohexylphenyl ketone.
  • ketal photopolymerization initiator examples include benzyl dimethyl ketal.
  • thioxanthone-based photopolymerization initiator examples include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, and dodecylthioxanthone.
  • acylphosphine oxide-based photopolymerization initiator examples include bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,4-di-n-butoxy phenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide and the like.
  • the content of the recombination-inhibiting compound (B) is determined by It is preferably 10 to 1000 parts by mass, more preferably 50 to 500 parts by mass, still more preferably 75 to 400 parts by mass, particularly preferably 100 parts by mass with respect to 100 parts by mass in total of one or more selected from the group consisting of ⁇ 300 parts by mass.
  • the pressure-sensitive adhesive layer and the like of the present invention may contain other components other than the components described above, if necessary.
  • the other components include resins other than the polymer (A), curing catalysts, cross-linking agents (including polyfunctional (meth)acrylates), cross-linking accelerators, polymerization initiators, tackifying resins (rosin derivatives, polyterpene resins , petroleum resin, oil-soluble phenol, etc.), oligomers, antioxidants, fillers (metal powder, organic fillers, inorganic fillers, etc.), coloring agents (pigments, dyes, etc.), antioxidants, plasticizers, softeners , Surfactant, Antistatic agent, Surface lubricant, Leveling agent, Light stabilizer, UV absorber, Sensitizer, Polymerization inhibitor, Granular material, Foil material, Flame retardant, Silane coupling agent, Ion trapping agent etc. Only one kind of each of the other components may be used, or two or more kinds thereof may be used.
  • Examples of the curing catalyst include organic titanium compounds and organic zirconium compounds.
  • Examples of the organic titanium compound include titanium alkoxide, titanium chelate, and titanium acylate.
  • Examples of the organic zirconium compounds include zirconium alkoxides, zirconium chelates, zirconium acylates, and the like.
  • Titanium alkoxides include tetraisopropyl titanate, tetra-normal butyl titanate, butyl titanate dimer, and tetraoctyl titanate.
  • Titanium chelates include titanium acetylacetonate, titanium tetraacetylacetonate, titanium ethylacetoacetate, and titanium octylene glycolate.
  • Titanium acylate includes titanium isostearate.
  • Zirconium alkoxides include normal propyl zirconate and normal butyl zirconate.
  • Zirconium chelates include zirconium tetraacetylacetonate and zirconium monoacetylacetonate.
  • Zirconium acylate includes zirconium stearate.
  • the content of the curing catalyst is not particularly limited, but from the viewpoint of imparting an appropriate initial hardness to the adhesive layer and the like and hardness after external stimulation, the total amount of the adhesive layer and the like of the present invention is 100% by mass. On the other hand, it is preferably 0.005 to 3% by mass, more preferably 0.01 to 1% by mass, still more preferably 0.05 to 1% by mass.
  • the above-mentioned cross-linking agent is not particularly limited as long as it cross-links the polymer.
  • (Meth)acrylate and the like examples include bifunctional or higher (meth)acrylic acid esters, such as trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, di pentaerythritol hexa(meth)acrylate and the like.
  • the adhesive layer of the present invention is formed from an adhesive composition. Also, the adhesive layer is formed from the adhesive composition.
  • the pressure-sensitive adhesive composition and the like preferably contain at least a base polymer and/or a raw material monomer thereof. Among them, it is preferable to include a base polymer from the viewpoint of exhibiting adhesiveness in the pressure-sensitive adhesive layer or the like to be obtained.
  • the base polymer is polymer (A) and/or other polymers (ie polymers without degradable bonds).
  • the pressure-sensitive adhesive composition and the like further contain compound (a). Only one type of the base polymer may be used, or two or more types may be used.
  • the pressure-sensitive adhesive composition or the like further contains compound (a).
  • a monomer component (sometimes referred to as "monomer component (c)") having reactivity with the compound (a) may also be included.
  • Compound (a) is reactive with the other polymer and/or monomer component (c).
  • the other polymer reacts with the compound (a) in the pressure-sensitive adhesive layer or the like by heat, active energy ray irradiation, or the like to form, for example, a polymer chain, The polymer chain and the other polymer combine to form a network structure, and a pressure-sensitive adhesive layer or the like containing the polymer (A) is obtained.
  • the compound (a) and the monomer component (c) react with heat, active energy ray irradiation, or the like in the adhesive layer or the like to form, for example, a polymer chain.
  • the polymer chains and the above-mentioned other polymers are entangled to form a network structure, and a pressure-sensitive adhesive layer or the like containing the polymer (A) is obtained.
  • Monomer component (c) may use only 1 type, and may use 2 or more types.
  • the compound (a) is incorporated into the base polymer when the raw material monomer is polymerized to form the polymer (A).
  • the raw material monomer is polymerized to form the other polymer, which is then reacted with compound (a) to form polymer (A).
  • the above-mentioned pressure-sensitive adhesive composition mainly includes (i) a pressure-sensitive adhesive composition containing the polymer (A), (ii) a pressure-sensitive adhesive composition containing the polymer (A) and the other polymer, and (iii) the above Other polymers, compound (a), pressure-sensitive adhesive composition containing monomer component (c) as necessary, (iv) raw material monomer, compound (a), pressure-sensitive adhesive containing monomer component (c) as necessary composition and the like.
  • the polymer (A) is the polymer (A1)
  • the pressure-sensitive adhesive compositions (i) to (iv) further contain the recombination inhibiting compound (B).
  • polymer (A) may be a reaction product of the other polymer, compound (a), and monomer (c), and a reaction product of the other polymer and the other polymer and compound (a). It may be a polymer comprising (particularly entangled) the Moreover, when the base polymer is polymer (A), the pressure-sensitive adhesive layer and the like may contain unreacted compound (a) and/or unreacted monomer (c).
  • the adhesive composition and the like may contain other components other than the components described above.
  • the other components include those exemplified and explained as other components that the pressure-sensitive adhesive layer of the present invention may contain, and solvents such as organic solvents. Only one kind of each of the other components may be used, or two or more kinds thereof may be used.
  • the pressure-sensitive adhesive composition or the like (sometimes referred to as "pressure-sensitive adhesive composition or the like (M1)") forming the pressure-sensitive adhesive layer or the like of the present invention containing the polymer (A1) further contains the recombination inhibiting compound (B).
  • the base polymer that may be contained in the pressure-sensitive adhesive composition (M1) is preferably the other polymer described above.
  • the base polymer examples include the thermoplastic resin, the thermosetting resin, the active energy ray-curable resin, and the like. Among them, thermoplastic resins and thermosetting resins are preferred.
  • a pressure-sensitive adhesive layer or the like containing a thermoplastic resin is capable of exerting adhesiveness such that it adheres under pressure from the outside, for example.
  • a pressure-sensitive adhesive layer or the like containing a thermosetting resin can be adhered to an adherend by being cured by heating, for example.
  • the compound (a1) includes a monomer component, an oligomer component, a cross-linking agent, and the like having the reversible degradable bond.
  • a cross-linking agent is preferable, and a cross-linking agent having a disulfide bond is more preferable.
  • the functional group (L1) possessed by the compound (a1) as the cross-linking agent is preferably a hydroxy group or a carboxy group from the viewpoint that the cross-linking density of the polymer (A1) is moderate.
  • the other polymer When the compound (a1) is reactive with the other polymer, the other polymer has a functional group (L2) that can react with the functional group (L1) in the compound (a1).
  • the functional group (L2) is appropriately selected according to the type of the functional group (L1) described above. ) acryloyl group, amino group, aldehyde group and the like.
  • Combinations of the functional group (L1) and the functional group (L2) include a carboxy group and a group containing a cyclic ether, a group containing a cyclic ether and a carboxy group, a carboxy group and an aziridyl group, an aziridyl group and a carboxy group, and a hydroxy group and isocyanate.
  • group, isocyanate group and hydroxy group, (meth)acryloyl group and (meth)acryloyl group, hydroxy group and amino group, amino group and hydroxy group, group containing cyclic ether and hydroxy group, hydroxy group and group containing cyclic ether, etc. is mentioned.
  • a combination of a carboxy group and a group containing a cyclic ether, a combination of a group containing a cyclic ether and a carboxy group, a combination of a group containing a cyclic ether and a hydroxy group, a combination of a hydroxy group and a cyclic Combinations of ether-containing groups are preferred. That is, it is preferable that the functional group (L1) is a hydroxyl group or a carboxy group, and the functional group (L2) is a group containing a cyclic ether (especially an epoxy group).
  • the number of functional groups (L2) in the other polymer having a functional group (L2) is 2, from the viewpoint of increasing the molecular weight after introduction into the polymer (a1) and further decreasing the molecular weight of the polymer after cleavage. It may be one or more (eg, 2 to 4). On the other hand, the number of functional groups (L2) is preferably 3 or less, more preferably 2, from the viewpoint of ensuring a certain degree of flexibility of the pressure-sensitive adhesive layer and the like with an appropriate crosslinking density.
  • the monomer component (c) is a compound having two or more polymerizable functional groups.
  • the polymerizable functional group is preferably a functional group (L3) capable of reacting with the functional group (L1) of the compound (a1) as a cross-linking agent.
  • the monomer (c) is crosslinked by the compound (a1) while being polymerized, thereby forming a polymer chain having a reversible degradable bond in the molecule.
  • the functional group (L3) can react with the functional group (L2).
  • the functional group (L3) is appropriately selected according to the type of the functional group (L1) or the functional group (L2) described above. , an isocyanate group, a (meth)acryloyl group, an amino group, an aldehyde group, and the like.
  • Examples of the combination of the functional group (L1) and the functional group (L3) include those exemplified and explained as the combination of the functional group (L1) and the functional group (L2) described above. Among them, from the viewpoint of ease of reaction tracking, a combination of a carboxy group and a group containing a cyclic ether, a combination of a group containing a cyclic ether and a carboxy group, a combination of a group containing a cyclic ether and a hydroxy group, and a hydroxy group and a cyclic ether Combinations of groups containing are preferred. That is, it is preferable that the functional group (L1) is a hydroxyl group or a carboxy group, and the functional group (L3) is a group containing a cyclic ether (especially an epoxy group).
  • the number of functional groups (L3) in the monomer component (c) is 2 or more (for example, 2 to 4).
  • the number of functional groups (L3) is preferably 3 or less, more preferably 2, from the viewpoint of ensuring a certain degree of flexibility of the pressure-sensitive adhesive layer and the like with an appropriate crosslinking density.
  • the functional group (L3) is preferably a group having a cyclic ether group, and particularly preferably an epoxy group. That is, an epoxy compound is preferable as the monomer component (c).
  • epoxy compounds include, for example, 4,4'-isopropylidenedicyclohexanol and (chloromethyl)oxirane.
  • the equivalent weight of the polymerizable functional group of the monomer component (c) is preferably 100 to 10,000 eq/g, more preferably 150 to 9,000 eq/g, from the viewpoint of making the crosslinked structure moderate and not too dense.
  • the content of the monomer component (c) in the pressure-sensitive adhesive composition (M1) is preferably 5 to 600 parts by mass with respect to 100 parts by mass of the total amount of the base polymer. , more preferably 7 to 500 parts by mass.
  • the other polymer is a thermosetting resin
  • the content is preferably 200 to 600 parts by mass, more preferably 300 to 500 parts by mass, and even more preferably 350 to 450 parts by mass.
  • the other polymer is a thermoplastic resin
  • the content is preferably 5 to 80 parts by mass, more preferably 5 to 50 parts by mass, and even more preferably 7 to 30 parts by mass.
  • the content of the monomer component (c) in the adhesive composition (M1) is 5 to 95% by mass with respect to 100% by mass of the total amount of the polymer (A1). is preferred, and more preferably 7 to 90% by mass.
  • the polymer (A1) is a thermosetting resin
  • the content is preferably 50 to 95% by mass, more preferably 60 to 90% by mass, still more preferably 65 to 85% by mass.
  • the polymer (A1) is a thermoplastic resin
  • the content is preferably 3 to 50% by mass, more preferably 5 to 40% by mass, still more preferably 6 to 30% by mass.
  • the content of the other polymers in the adhesive composition (M1) is based on 100% by mass of the total amount of the adhesive composition (M1) (excluding components such as organic solvents that do not remain when forming the layer). is preferably 5 to 99% by mass, more preferably 10 to 95% by mass.
  • the other polymer is a thermosetting resin
  • the content is preferably 5 to 50% by mass, more preferably 7 to 40% by mass, still more preferably 10 to 30% by mass.
  • the other polymer is a thermoplastic resin
  • the content is preferably 30 to 99% by mass, more preferably 50 to 95% by mass, still more preferably 60 to 90% by mass.
  • the content is 5% by mass or more, it is easy to impart adhesiveness to the pressure-sensitive adhesive layer and the like.
  • the content is 99% by mass or less, it is easy to design the composition by blending the cross-linking agent and the recombination-inhibiting compound (B) component.
  • the content of the cross-linking agent and/or the structural portion derived from the cross-linking agent in the pressure-sensitive adhesive composition (M1) is 0.00 parts per 100 parts by mass of the other polymer and/or monomer component (c). It is preferably 5 to 40 parts by mass, more preferably 1 to 35 parts by mass, still more preferably 1.5 to 30 parts by mass.
  • the content includes the amount of the compound (a1).
  • the base polymer that can be included in the adhesive composition, etc. (sometimes referred to as "adhesive composition, etc. (M2)") that forms the adhesive layer, etc. of the present invention containing the polymer (A2) is, among others, the polymer (A2 ), more preferably the polymer (A2) and the above other polymers.
  • the polymer (A2) is preferably a curable resin.
  • the curability of the curable resin is appropriately selected according to the type of the irreversibly decomposable bond, and when the irreversibly decomposable bond can be cleaved by active energy rays, it is preferably a thermosetting resin.
  • the polymer (A2) which is the curable resin, is preferably a resin (prepolymer) having a polymerizable functional group.
  • a resin prepolymer
  • polymerization of the polymerizable functional groups proceeds by heat or active energy ray irradiation after application of the adhesive composition or the like. , can form a network structure by entangling with other polymers. That is, the polymer (A2) is preferably a polymer capable of forming the above network structure.
  • the base polymer examples include the thermoplastic resin, the thermosetting resin, the active energy ray-curable resin, and the like.
  • the polymer (A2) as the base polymer is preferably a curable resin, more preferably a thermosetting resin.
  • Thermoplastic resins are preferable as the other polymers.
  • a pressure-sensitive adhesive layer or the like containing a thermoplastic resin is capable of exerting adhesiveness such that it adheres under pressure from the outside, for example.
  • An adhesive composition or the like containing a curable resin can form a network structure by being cured, for example, by heating.
  • the other polymer may be a curable resin, and in this case, the polymer (A2), which is also a curable resin, and the other polymer form a bond between the two resins by heat, active energy ray irradiation, or the like. It becomes possible to form a network structure.
  • the compound (a2) includes a monomer component, an oligomer component, a cross-linking agent, and the like having the irreversibly degradable bond.
  • the monomer component that is, the compound having the polymerizable functional group
  • the nitrobenzyl-based monomer is more preferred
  • the nitrobenzyl ester-based monomer is even more preferred.
  • the content of the polymer (A2) in the base polymer is preferably 10 to 90% by mass, more preferably 30 to 70% by mass, more preferably 40 to 90% by mass, relative to the total amount (100% by mass) of the base polymer. 60% by mass.
  • the content is 10% by mass or more, a sufficient amount of the irreversible degradable bond is cleaved by an external stimulus.
  • the content is 90% by mass or less, appropriate tackiness and/or adhesiveness can be maintained even after application of an external stimulus.
  • the content of the other polymer in the base polymer is preferably 10 to 90% by mass, more preferably 30 to 70% by mass, more preferably 40 to 90% by mass, relative to the total amount (100% by mass) of the base polymer. 60% by mass.
  • the content is 10% by mass or more, appropriate tackiness and/or adhesiveness can be maintained even after application of an external stimulus.
  • the polymer (A2) can be sufficiently blended, whereby a sufficient amount of irreversible degradable bonds are cleaved by an external stimulus.
  • the content of structural units derived from the compound (a2) in the polymer (A2) is preferably 0.2 to 30% by mass, more preferably 0.5 to 30% by mass, relative to 100% by mass of the total amount of the polymer (A2). 15% by mass, more preferably 0.8 to 10% by mass.
  • the pressure-sensitive adhesive composition or the like (M2) contains raw material monomers constituting the base polymer
  • the content of the compound (a2) in all the monomer components constituting the polymer (A2) is preferably within the above range.
  • the content of structural units derived from acrylic monomers in the polymer (A2) is 70 to 99.8 with respect to 100% by mass of the total amount of the polymer (A2). % by mass is preferable, more preferably 85 to 99.5% by mass, and still more preferably 90 to 99.2% by mass.
  • the pressure-sensitive adhesive composition or the like (M2) contains raw material monomers constituting the base polymer, the content of the acrylic monomer in all the monomer components constituting the polymer (A2) is preferably within the above range.
  • the content of structural units derived from the compound (a2) in the base polymer is 100% by mass in the total amount of the base polymer in order to exhibit sufficient flexibility by being cleaved and shredded after application of an external stimulus. is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, still more preferably 0.5% by mass or more, and particularly preferably 1% by mass or more. Also, in order to make the crosslink density appropriate and to impart appropriate flexibility to the resin before applying an external stimulus, the amount is preferably 15% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less.
  • the pressure-sensitive adhesive composition or the like (M2) contains raw material monomers constituting the base polymer
  • the content of the compound (a2) in all the monomer components constituting the base polymer is preferably within the above range.
  • the content of structural units derived from acrylic monomers in the base polymer is preferably 85 to 99.9% by mass with respect to 100% by mass of the total amount of the base polymer. , more preferably 90 to 99.8% by mass, more preferably 95 to 99.5% by mass.
  • the pressure-sensitive adhesive composition or the like (M2) contains raw material monomers constituting the base polymer, the content of the acrylic monomer in all the monomer components constituting the base polymer is preferably within the above range.
  • the content of the base polymer in the adhesive composition (M2) is based on 100% by mass of the total amount of the adhesive composition (M2) (excluding components such as organic solvents that do not remain during layer formation). It is preferably 50% by mass or more, more preferably 70% by mass or more, still more preferably 80% by mass or more, and particularly preferably 90% by mass or more.
  • the release liner protects the pressure-sensitive adhesive surface and/or adhesive surface with which the pressure-sensitive adhesive layer or the like of the present invention comes into contact until use, and is peeled off when the pressure-sensitive adhesive layer or the like is used.
  • base materials for the release liner include polyethylene film, polypropylene film, polybutene film, polybutadiene film, polymethylpentene film, polyvinyl chloride film, vinyl chloride copolymer film, polyethylene terephthalate film, polyethylene naphthalate film, poly Butylene terephthalate film, polyurethane film, ethylene vinyl acetate film, ionomer resin film, ethylene/(meth)acrylic acid copolymer film, ethylene/(meth)acrylic acid ester copolymer film, polystyrene film, polycarbonate film, polyimide film, A fluorine resin film etc. are mentioned. Moreover, these crosslinked films are also mentioned. Furthermore, a laminated film of these may be used.
  • the release surface of the release liner (especially the surface in contact with the pressure-sensitive adhesive layer, etc.) is preferably subjected to a release treatment.
  • release agents used in the release treatment include alkyd-based, silicone-based, fluorine-based, unsaturated polyester-based, polyolefin-based, and wax-based release agents.
  • the thickness of the release liner is not particularly limited, it is, for example, about 20 to 150 ⁇ m.
  • the pressure-sensitive adhesive sheet with a release liner or adhesive sheet 10 shown in FIG. 1 can be produced by the following method. After forming a coating layer by applying a pressure-sensitive adhesive composition or the like for forming the pressure-sensitive adhesive layer or the like 1 to the base material layer or the release-treated surface of the release liner 2 that has been subjected to the release treatment, the solvent is removed by heating, or It can be prepared by hardening the coating layer by heat curing or curing by irradiation with active energy rays. In addition, when performing active energy ray irradiation, it is performed after bonding a separate release liner on the coating layer.
  • the adhesive composition and the like may be in any form as long as it does not impair the effects of the present invention.
  • the pressure-sensitive adhesive composition may be emulsion type, solvent type (solution type), heat melting type (hot melt type), or the like.
  • the solvent type is preferable because it is easy to obtain a pressure-sensitive adhesive layer with excellent productivity.
  • the adhesive layer or the like is formed by heating when the coating layer is solidified.
  • the pressure-sensitive adhesive composition or the like contains the other polymer and/or raw material monomer and the compound (a)
  • the raw material monomer is optionally removed by heating or active energy ray irradiation when solidifying the coating layer. is polymerized, the compound (a) forms a bond with the polymer of the raw material monomers and the above-mentioned other polymer to form the polymer (A), and at the same time the pressure-sensitive adhesive layer and the like are formed.
  • the pressure-sensitive adhesive layer and the like may be heated or irradiated with an active energy ray, or when the polymer (A) is a curable resin, a curing treatment may be performed.
  • the pressure-sensitive adhesive sheet with a release liner or adhesive sheet 10 shown in FIG. 1 is obtained.
  • the use of the pressure-sensitive adhesive layer, etc. of the present invention is not particularly limited, and it can be used for any purpose.
  • the pressure-sensitive adhesive layer and the like of the present invention can be used, for example, for optical applications, that is, applications for bonding to optical members.
  • the pressure-sensitive adhesive layer or the like of the present invention is used, for example, in optical members such as electric and electronic devices, when various members or parts are attached (mounted) to predetermined portions (for example, housings and the like).
  • “electrical/electronic equipment” refers to equipment corresponding to at least one of electric equipment and electronic equipment. Examples of the electric/electronic equipment include image display devices such as liquid crystal displays, electroluminescence displays, and plasma displays, and mobile electronic equipment. Examples of the image display device include an image display device in the portable electronic device, a display (roll display) inside and outside a vehicle such as a train or a bus, and the like.
  • Examples of the portable electronic devices include mobile phones, smartphones, tablet computers, notebook computers, and various wearable devices (for example, wrist wear types that are worn on the wrist like wristwatches, clips, straps, etc. that are attached to a part of the body) Modular type to be worn, eyewear type including eyeglass type (monocular type and binocular type, including head-mounted type), clothing type that can be attached to shirts, socks, hats, etc.
  • wearable devices for example, wrist wear types that are worn on the wrist like wristwatches, clips, straps, etc. that are attached to a part of the body
  • Modular type to be worn for example, wrist wear types that are worn on the wrist like wristwatches, clips, straps, etc. that are attached to a part of the body
  • eyewear type including eyeglass type (monocular type and binocular type, including head-mounted type)
  • clothing type that can be attached to shirts, socks, hats, etc.
  • the term “portable” means not only being able to be carried but also having a level of portability that allows individuals (standard adults) to relatively easily carry it. shall mean.
  • the pressure-sensitive adhesive layer, etc. of the present invention has excellent handleability before being adhered or adhered to members during manufacturing, processing, storage, transportation, etc., and is excellent in flexibility after being adhered or adhered to members. For this reason, it is possible to prevent the paste from overflowing, the paste from being cut out, and the process contamination caused by these when the punching blade cuts out, for example. In addition, the glue is less likely to ooze out due to its own weight during storage, and less likely to cause glue chipping due to vibration or contact during transportation.
  • the pressure-sensitive adhesive layer or the like of the present invention can reduce stress by external stimuli, it is possible to vary the adhesive strength and adhesive strength.
  • a pressure-sensitive adhesive sheet and/or an adhesive sheet can be obtained using the pressure-sensitive adhesive layer or the like of the present invention.
  • an adhesive sheet and/or an adhesive sheet may be called “adhesive sheet etc.”.
  • the pressure-sensitive adhesive sheet or the like may be a so-called “substrate-less type” pressure-sensitive adhesive sheet or the like that does not have a substrate (substrate layer), or may be a type pressure-sensitive adhesive sheet or the like that has a substrate.
  • a "substrate-less type" pressure-sensitive adhesive sheet or the like may be referred to as a "substrate-less pressure-sensitive adhesive sheet or the like”
  • a type pressure-sensitive adhesive sheet or the like having a substrate may be referred to as a "substrate-attached pressure-sensitive adhesive sheet or the like.”
  • the substrate-less pressure-sensitive adhesive sheet or the like include, for example, a double-sided pressure-sensitive adhesive sheet or the like consisting only of the pressure-sensitive adhesive layer of the present invention, or the pressure-sensitive adhesive layer of the present invention and other pressure-sensitive adhesive layers (such as the pressure-sensitive adhesive layer of the present invention).
  • a double-sided pressure-sensitive adhesive sheet made of a pressure-sensitive adhesive layer, etc., other than the above) may be mentioned.
  • the adhesive sheet with a substrate or the like is a pressure-sensitive adhesive sheet or the like containing a substrate and the adhesive layer or the like of the present invention formed on at least one surface of the substrate.
  • Examples include a double-sided pressure-sensitive adhesive sheet having a layer or the like and having another pressure-sensitive adhesive layer or the like on the other side.
  • base material refers to a support, and when using (sticking) an adhesive sheet or the like on an adherend, This is the part where A release liner that is peeled off when using (sticking) an adhesive sheet or the like is not included in the base material.
  • the substrate is not particularly limited.
  • Various optical films such as a retardation plate can be used.
  • the base material include porous materials such as paper, cloth, and nonwoven fabric, nets, foam sheets, metal foils, and the like.
  • Plastic film Materials for the plastic film include, for example, polyester resins such as polyethylene terephthalate (PET), acrylic resins such as polymethyl methacrylate (PMMA), polycarbonate, triacetyl cellulose (TAC), polysulfone, polyarylate, polyimide, Polyvinyl chloride, polyvinyl acetate, polyethylene, polypropylene, ethylene-propylene copolymer, trade name “Arton” (cyclic olefin polymer, manufactured by JSR Corporation), trade name “Zeonor” (cyclic olefin polymer, Nippon Zeon Co., Ltd.) company) and other plastic materials such as cyclic olefin polymers. These plastic materials may be used alone or in combination of two or more.
  • PET polyethylene terephthalate
  • PMMA polymethyl methacrylate
  • TAC triacetyl cellulose
  • Polysulfone polyarylate
  • Polyimide Polyvinyl chloride
  • Polyvinyl acetate
  • the thickness of the base material is not particularly limited, it is preferably 10 to 150 ⁇ m, more preferably 15 to 125 ⁇ m, still more preferably 25 to 100 ⁇ m.
  • the substrate may have either a single-layer structure or a multilayer structure.
  • the surface of the substrate may be appropriately subjected to known and commonly used surface treatments such as physical treatments such as corona discharge treatment and plasma treatment, and chemical treatments such as undercoating treatment.
  • the adhesive sheet, etc. may be provided with a release liner on the surface (adhesive surface or adhesive surface) of the adhesive layer, etc. until use.
  • a release liner on the surface (adhesive surface or adhesive surface) of the adhesive layer, etc. until use.
  • each adhesive surface or adhesive surface may be protected by two release liners, or one release liner having release surfaces on both sides. may be protected in the form of being wound into a roll (wound body).
  • a release liner is used as a protective material such as a pressure-sensitive adhesive layer, and is peeled off when applied to an adherend.
  • the pressure-sensitive adhesive sheet or the like is a substrate-less pressure-sensitive adhesive sheet or the like
  • the release liner also serves as a support for the pressure-sensitive adhesive layer and the like. Note that the release liner does not necessarily have to be provided.
  • Example 1 Epoxy monomer (trade name “HBE100”, manufactured by Shin Nippon Rika Co., Ltd., equivalent to monomer component (c)) 100 parts by mass, epoxy resin (trade name “1256B40”, manufactured by Mitsubishi Chemical Corporation) 25 parts by mass, epoxy curing 20 parts by mass of 4,4'-dithiodibutyric acid (manufactured by Tokyo Chemical Industry Co., Ltd., equivalent to compound (a1)) as an agent, a radical scavenger (trade name “Omnirad TPO H", manufactured by IGM Resins BV, Equivalent to recombination inhibiting compound (B)) 25 parts by mass, curing catalyst (trade name “ZC700”, manufactured by Matsumoto Fine Chemicals Co., Ltd.) 0.1 parts by mass, and 3 parts by mass of acetylacetone (AcAc), respectively, 500 parts by mass of methyl ethyl ketone and mixed with stirring to prepare a mixed solution.
  • epoxy resin trade name “1256B40”, manufactured
  • This mixed solution was applied to a 38 ⁇ m thick release liner R1 (trade name “MRF#38”, manufactured by Mitsubishi Chemical Corporation) having a release surface on one side of a polyester film, and dried in an oven at 100° C. for 5 minutes. rice field. After drying, the coated surface was covered with a 38 ⁇ m thick release liner R2 (trade name “MRE #38”, manufactured by Mitsubishi Chemical Corporation) whose one side is a release surface of a polyester film, and was heat cured. A 50 ⁇ m-thick pressure-sensitive adhesive sheet containing a mold resin (corresponding to polymer (A1)) was prepared.
  • adheresion refers to having properties of both stickiness and adhesiveness.
  • Example 2 A pressure-sensitive adhesive sheet containing a thermosetting resin (corresponding to polymer (A1)) was produced in the same manner as in Example 1, except that the trade name "jER828" (manufactured by Mitsubishi Chemical Corporation) was used as the epoxy monomer. .
  • Example 3 Adhesive containing a thermosetting resin (corresponding to polymer (A1)) was prepared in the same manner as in Example 2 except that the product name "Omnirad 651" (manufactured by IGM Resins B.V.) was used as a radical scavenger. An attachment sheet was produced.
  • Example 4 Adhesive containing thermosetting resin (corresponding to polymer (A1)) in the same manner as in Example 1 except that 4,4'-dithiodiphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) was used as the epoxy curing agent. An attachment sheet was produced.
  • Example 5 Adhesive containing thermosetting resin (corresponding to polymer (A1)) in the same manner as in Example 2 except that 4,4'-dithiodiphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) was used as the epoxy curing agent. An attachment sheet was produced.
  • Comparative example 1 A pressure-sensitive adhesive sheet containing a thermosetting resin (corresponding to polymer (A1)) was produced in the same manner as in Example 2, except that no radical scavenger was used.
  • Comparative example 2 A pressure-sensitive adhesive sheet containing a thermosetting resin was produced in the same manner as in Example 1, except that 4,4'-ethylidenebisphenol was used as the epoxy curing agent.
  • Comparative example 3 A pressure-sensitive adhesive sheet containing a thermosetting resin was produced in the same manner as in Comparative Example 2, except that no radical scavenger was used.
  • Example 6 (Preparation of acrylic polymer) In a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser, and a nitrogen gas inlet tube, 95 parts by mass of n-butyl acrylate (BA), 5 parts by mass of acrylic acid (AA), and 2 as a polymerization initiator. , 2′-azobisisobutyronitrile (AIBN) and 122 parts by mass of ethyl acetate as a solvent were stirred under a nitrogen atmosphere at 60° C. for 7 hours. Thus, a polymer solution containing an acrylic polymer was obtained. The acrylic polymer in this polymer solution had a weight average molecular weight (Mw) of 600,000.
  • Adhesive Sheet 100 parts by mass of the acrylic polymer (dissolved in ethyl acetate), 0.1 part by mass of a cross-linking agent (trade name "Tetrad C", manufactured by Mitsubishi Gas Chemical Co., Ltd.), epoxy monomer (trade name "HBE100”, New Japan Chemical Co., Ltd.
  • This mixed solution was applied to a 38 ⁇ m thick release liner R1 (trade name “MRF#38”, manufactured by Mitsubishi Chemical Corporation) having a release surface on one side of a polyester film, and dried in an oven at 100° C. for 5 minutes. rice field. After drying, the coated surface was covered with a 38 ⁇ m thick release liner R2 (trade name “MRE #38”, manufactured by Mitsubishi Chemical Corporation) whose one side is a release surface of a polyester film, and was heat cured. A 50 ⁇ m-thick pressure-sensitive adhesive sheet containing a curable resin (corresponding to polymer (A1)) was prepared.
  • Example 7 A pressure-sensitive adhesive sheet containing a thermosetting resin (corresponding to polymer (A1)) was prepared in the same manner as in Example 6, except that the product name "jER828" (manufactured by Mitsubishi Chemical Corporation) was used as the epoxy monomer. bottom.
  • Comparative example 4 To 100 parts by mass of the acrylic polymer prepared in Example 6 (dissolved in ethyl acetate), 0.1 part by mass of a cross-linking agent (trade name "Tetrad C", manufactured by Mitsubishi Gas Chemical Company, Inc.) was added, and the mixture was stirred and mixed. A solution was prepared. A pressure-sensitive adhesive sheet was produced in the same manner as in Example 6, except that this mixed solution was used.
  • a cross-linking agent trade name "Tetrad C", manufactured by Mitsubishi Gas Chemical Company, Inc.
  • Comparative example 5 A pressure-sensitive adhesive sheet containing a thermosetting resin (corresponding to polymer (A1)) was produced in the same manner as in Example 6, except that no radical scavenger was used.
  • Comparative example 6 A pressure-sensitive adhesive sheet containing a thermosetting resin (corresponding to polymer (A1)) was produced in the same manner as in Example 7, except that no radical scavenger was used.
  • Preparation example 3 Synthesis of acrylic polymer P1
  • a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser, and a nitrogen gas inlet tube 95 parts by mass of n-butyl acrylate (BA), 5 parts by mass of acrylic acid (AA), and 0.2 of AIBN as a polymerization initiator.
  • a mixture containing parts by mass and 122 parts by mass of ethyl acetate as a solvent was stirred at 60° C. for 7 hours under a nitrogen atmosphere to carry out a polymerization reaction.
  • a polymer solution containing the acrylic polymer P1 was obtained.
  • the weight average molecular weight (Mw) of the acrylic polymer P1 in this polymer solution was 600,000.
  • Example 8 Synthesis of acrylic polymer P2 In a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser, and a nitrogen gas inlet tube, 95 parts by mass of butyl acrylate (BA) and the nitrobenzyl ester monomer prepared in Preparation Example 2 (corresponding to compound (a2)) 5 parts by mass, trade name "C12TCSS" (manufactured by Nippon Terpene Chemical Co., Ltd.) as a chain transfer agent 2.83 parts by mass, 2,2'-azobisisobutyronitrile (AIBN) as a polymerization initiator 0.28 A mixture containing parts by mass and 301 parts by mass of ethyl acetate as a solvent was stirred at 60° C. for 6 hours under a nitrogen atmosphere to carry out a polymerization reaction. As a result, a polymer solution containing acrylic polymer P2 (corresponding to polymer (A2)), which is a prepolymer having acryloyl groups, was
  • the pressure-sensitive adhesive composition was applied to the release-treated surface of a polyethylene terephthalate film (trade name: "MRF38", manufactured by Mitsubishi Chemical Corporation) with a silicone-based release agent, and the thickness of the pressure-sensitive adhesive layer after drying was was applied so as to have a thickness of 25 ⁇ m, allowed to stand at room temperature for 5 minutes, and then dried at 130° C. for 3 minutes.
  • a pressure-sensitive adhesive sheet was obtained by sufficiently volatilizing and removing ethyl acetate contained as a solvent.
  • Comparative example 7 Synthesis of acrylic polymer P3 95 parts by mass of butyl acrylate (BA), 5 parts by mass of 1,6-hexanediol diacrylate, and a commercial product as a chain transfer agent were placed in a reaction vessel equipped with a stirrer, thermometer, reflux condenser, and nitrogen gas inlet tube.
  • Name "C12TCSS” manufactured by Nippon Terpene Chemical Co., Ltd.
  • AIBN 2,2'-azobisisobutyronitrile
  • ethyl acetate 301 as a solvent
  • a mixture containing parts by mass was stirred at 60° C. for 6 hours under a nitrogen atmosphere to carry out a polymerization reaction.
  • a polymer solution containing acrylic polymer P3, which is a prepolymer having acryloyl groups was obtained.
  • a pressure-sensitive adhesive sheet was prepared in the same manner as in Example 8, except that the pressure-sensitive adhesive composition prepared above was used.
  • Comparative example 8 Synthesis of acrylic polymer P4
  • BA butyl acrylate
  • C12TCSS trade name "manufactured by Nippon Terpene Chemical Co., Ltd.”
  • a mixture containing 2.83 parts by mass, 0.28 parts by mass of 2,2'-azobisisobutyronitrile (AIBN) as a polymerization initiator, and 301 parts by mass of ethyl acetate as a solvent was heated at 60°C for 6 hours. , and stirred under a nitrogen atmosphere to carry out a polymerization reaction.
  • AIBN 2,2'-azobisisobutyronitrile
  • a pressure-sensitive adhesive sheet was prepared in the same manner as in Example 8, except that the pressure-sensitive adhesive composition prepared above was used.
  • Example 9 (Preparation of acrylic polymer) 63 parts by weight of 2-ethylhexyl acrylate (2EHA), 15 parts by weight of N-vinylpyrrolidone (NVP), and methyl methacrylate (MMA) were placed in a reaction vessel equipped with a stirrer, thermometer, reflux condenser, and nitrogen gas inlet tube. ) 9 parts by mass, 13 parts by mass of hydroxyethyl acrylate (HEA), 0.2 parts by mass of 2,2′-azobisisobutyronitrile (AIBN) as a polymerization initiator, and 122 parts by mass of ethyl acetate as a solvent The mixture containing parts was stirred at 60° C. for 7 hours under a nitrogen atmosphere. Thus, a polymer solution containing an acrylic polymer was obtained. The acrylic polymer in this polymer solution had a weight average molecular weight (Mw) of 600,000.
  • Adhesive Sheet 100 parts by mass of the acrylic polymer (dissolved in ethyl acetate), 4 parts by mass of a cross-linking agent (trade name "Takenate D110N", manufactured by Mitsui Chemicals, Inc.), a curing agent (4,4'-dithiodianiline, compound (a1) equivalent) 1 part by mass, 0.1 part by mass of a cross-linking catalyst (trade name “ZC700”, manufactured by Matsumoto Fine Chemical Co., Ltd.), 2 parts by mass of acetylacetone (AcAc), and a radical scavenger (trade name “Omnirad TPO H”, IGM Resins B.V.) was added to each of them, and mixed and stirred to prepare a mixed solution.
  • a cross-linking agent trade name "Takenate D110N", manufactured by Mitsui Chemicals, Inc.
  • a curing agent 4,4'-dithiodianiline, compound (a1) equivalent
  • ZC700 manufactured by
  • This mixed solution was applied to a 38 ⁇ m thick release liner R1 (trade name “MRF#38”, manufactured by Mitsubishi Chemical Corporation) having a release surface on one side of a polyester film, and dried in an oven at 100° C. for 5 minutes. rice field. After drying, the coated surface was covered with a 38 ⁇ m thick release liner R2 (trade name “MRE #38”, manufactured by Mitsubishi Chemical Corporation) whose one side is a release surface of a polyester film, and was heat cured. A 50 ⁇ m-thick pressure-sensitive adhesive sheet containing a curable resin (corresponding to polymer (A1)) was prepared.
  • Comparative example 9 A pressure-sensitive adhesive sheet containing a thermosetting resin (corresponding to polymer (A1)) was produced in the same manner as in Example 9, except that no radical scavenger was used.
  • Example 10 (Formation of Adhesive Sheet) 100 parts by mass of the acrylic polymer prepared in Example 6 (dissolved in ethyl acetate), 1,3-bis(4,5-dihydro-2-oxazolyl)benzene (manufactured by Tokyo Chemical Industry Co., Ltd.) as a cross-linking agent 4 parts by mass , a curing agent (4,4'-dithiodiphenol, corresponding to compound (a1)) 4 parts by mass, and a radical scavenger (trade name "Omnirad TPO H", manufactured by IGM Resins B.V.) 5 parts by mass. Each was added and mixed and stirred to prepare a mixed solution.
  • This mixed solution was applied to a 38 ⁇ m thick release liner R1 (trade name “MRF#38”, manufactured by Mitsubishi Chemical Corporation) having a release surface on one side of a polyester film, and dried in an oven at 100° C. for 5 minutes. rice field. After drying, the coated surface was covered with a 38 ⁇ m thick release liner R2 (trade name “MRE #38”, manufactured by Mitsubishi Chemical Corporation) whose one side is a release surface of a polyester film, and was heat cured. A 50 ⁇ m-thick pressure-sensitive adhesive sheet containing a curable resin (corresponding to polymer (A1)) was prepared.
  • Example 11 A pressure-sensitive adhesive sheet was prepared in the same manner as in Example 10, except that 4,4'-dithiodibutyric acid (corresponding to compound (a1)) was used as the curing agent.
  • Comparative example 10 A pressure-sensitive adhesive sheet containing a thermosetting resin (corresponding to polymer (A1)) was produced in the same manner as in Example 10, except that no radical scavenger was used.
  • Comparative example 11 A pressure-sensitive adhesive sheet containing a thermosetting resin (corresponding to polymer (A1)) was produced in the same manner as in Example 11, except that no radical scavenger was used.
  • Comparative example 12 A pressure-sensitive adhesive sheet containing a thermosetting resin (corresponding to polymer (A1)) was prepared in the same manner as in Example 10, except that no curing agent was used.
  • UV irradiation For the adhesive sheets obtained in Examples and Comparative Examples, a release liner was further attached to the exposed adhesive surface, and a UV-LED irradiation device manufactured by Quark Technology Co., Ltd. (model number "QEL-350-RU6W-CW -MY”), a UV-LED lamp with a wavelength of 365 nm was used as a light source, and ultraviolet irradiation was performed with an integrated irradiation light amount of 8000 mJ/cm 2 in the wavelength range of 320 to 390 nm.
  • Shear storage modulus Adhesive sheets were laminated to prepare a sample for measurement with a thickness of about 1.0 mm, and subjected to the following conditions using "Advanced Rheometric Expansion System (ARES)" manufactured by Rheometric Scientific. A dynamic viscoelasticity measurement was performed by Then, the shear storage elastic moduli at 25°C, 50°C and 80°C were calculated.
  • Deformation mode Torsion Measurement frequency: 1Hz Heating rate: 5°C/min Measurement temperature: -50 to 150°C Shape: Parallel plate 8.0mm ⁇
  • the pressure-sensitive adhesive sheets of Examples decreased in hardness such as Young's modulus due to ultraviolet irradiation. For this reason, it was judged to be excellent in flexibility before UV irradiation because the handleability was superior to that after UV irradiation, and on the other hand, hardness decreased after UV irradiation.
  • [Appendix 1] A pressure-sensitive adhesive layer and/or an adhesive layer whose hardness is reduced by an external stimulus.
  • Appendix 2 The pressure-sensitive adhesive layer and/or adhesive layer according to Appendix 1, wherein the hardness does not increase after the reduction.
  • Appendix 3 The pressure-sensitive adhesive layer according to Appendix 1 or 2, wherein the ratio [E2/E1] of Young's modulus (E1) before application of an external stimulus to Young's modulus (E2) after application of an external stimulus is less than 0.95. and/or an adhesive layer.
  • [Appendix 4] The pressure-sensitive adhesive layer and/or adhesive layer according to any one of Appendices 1 to 3, which has a Young's modulus (E2) of less than 50 MPa after application of an external stimulus.
  • Appendix 5 The ratio of the breaking elongation (B1) before applying an external stimulus to the breaking elongation (B2) after applying an external stimulus [breaking elongation (B2)/breaking elongation (B1)] is more than 1.1.
  • [Appendix 6] The pressure-sensitive adhesive layer and/or adhesive layer according to any one of Appendices 1 to 5, which is used for optical applications.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Materials For Medical Uses (AREA)
  • Adhesive Tapes (AREA)

Abstract

L'invention fournit une couche d'agent collant et/ou une couche d'adhésif qui est excellente en termes de propriétés de manipulation avant collage ou mise en adhésion sur un élément, et également en termes de souplesse après collage ou mise en adhésion sur un élément.　Plus précisément, l'invention fournit une couche d'agent collant et/ou une couche d'adhésif dont la dureté est réduite par stimulation externe. De préférence, après sa réduction ladite dureté n'est pas augmentée. En outre, de préférence, le rapport ［Ｅ２／Ｅ１］ entre le module de Young (E1) avant application de la stimulation externe et le module de Young (E2) après application de la stimulation externe, est inférieur à ０,９５. Enfin, de préférence le module de Young (E2) après application de la stimulation externe est inférieur à ５０ＭＰａ.
PCT/JP2022/043960 2021-11-30 2022-11-29 Couche d'agent collant et/ou couche d'adhésif WO2023100863A1 (fr)

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WO2017191827A1 (fr) * 2016-05-02 2017-11-09 国立大学法人 東京医科歯科大学 Polyrotaxane dégradable intérieurement et son procédé de synthèse
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US20200332161A1 (en) * 2019-04-17 2020-10-22 The Florida State University Research Foundation, Inc. Zwitterionic crosslinked polymer-based adhesives
WO2022075366A1 (fr) * 2020-10-07 2022-04-14 昭和電工マテリアルズ株式会社 Ensemble adhésif, film, corps lié, et procédé de séparation d'un adhérent

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JP2007131710A (ja) * 2005-11-09 2007-05-31 Lintec Corp 光分解性高分子化合物の製造方法
WO2017191827A1 (fr) * 2016-05-02 2017-11-09 国立大学法人 東京医科歯科大学 Polyrotaxane dégradable intérieurement et son procédé de synthèse
CN109735280A (zh) * 2019-01-04 2019-05-10 中国科学技术大学 紫外光响应性聚合物粘合剂及其制备方法和用途
US20200332161A1 (en) * 2019-04-17 2020-10-22 The Florida State University Research Foundation, Inc. Zwitterionic crosslinked polymer-based adhesives
WO2022075366A1 (fr) * 2020-10-07 2022-04-14 昭和電工マテリアルズ株式会社 Ensemble adhésif, film, corps lié, et procédé de séparation d'un adhérent

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MIYAMOTO, YUKI; AMANO, YOSHIHIRO; SAITO, SHOICHI: "Development of Photo-Melt Resin", JOURNAL OF NETWORKPOLYMER, JP, vol. 42, no. 5, 10 September 2021 (2021-09-10), JP, pages 176 - 183, XP009546699, ISSN: 2433-3786, DOI: 10.11364/networkedpolymer.42.5_176 *

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