WO2022038926A1 - 接合体の分離方法 - Google Patents

接合体の分離方法 Download PDF

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Publication number
WO2022038926A1
WO2022038926A1 PCT/JP2021/026289 JP2021026289W WO2022038926A1 WO 2022038926 A1 WO2022038926 A1 WO 2022038926A1 JP 2021026289 W JP2021026289 W JP 2021026289W WO 2022038926 A1 WO2022038926 A1 WO 2022038926A1
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WIPO (PCT)
Prior art keywords
pressure
sensitive adhesive
solvent
adhesive
peeling
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/JP2021/026289
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English (en)
French (fr)
Japanese (ja)
Inventor
尚史 小坂
陽介 清水
健太 熊倉
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Nitto Denko Corp
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Nitto Denko Corp
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Priority to CN202180055738.6A priority Critical patent/CN116018384B/zh
Priority to JP2022543319A priority patent/JP7828894B2/ja
Publication of WO2022038926A1 publication Critical patent/WO2022038926A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/62—Plastics recycling; Rubber recycling

Definitions

  • the present invention relates to a method for separating a bonded body.
  • a pressure-sensitive adhesive (also referred to as a pressure-sensitive adhesive; the same applies hereinafter) exhibits a soft solid state (viscous elastic body) in a temperature range near room temperature, and has a property of easily adhering to an adherend by pressure.
  • the pressure-sensitive adhesive is widely used in various fields in the form of a pressure-sensitive adhesive sheet with a support having a pressure-sensitive adhesive layer on the support or in the form of a support-less pressure-sensitive adhesive sheet having no support. It's being used. Further, after use, the pressure-sensitive adhesive is peeled off from the adherend by an appropriate means, if necessary.
  • Patent Document 1 is mentioned as a technical document relating to the pressure-sensitive adhesive sheet.
  • Patent Document 2 is mentioned as a technical document for peeling the adhesive from the adherend.
  • the display device built into a product having a display function such as a smartphone, a personal computer (desktop type, notebook type, tablet type, etc.), a television, etc.
  • a liquid crystal display device such as a smartphone, a personal computer (desktop type, notebook type, tablet type, etc.), a television, etc.
  • a liquid crystal display device such as a smartphone, a personal computer (desktop type, notebook type, tablet type, etc.), a television, etc.
  • organic EL electroluminescence
  • It has a multi-layer structure including multiple and different types of functional members such as PDPs (plasma display panels), and since each member contains different materials, it has a great advantage of being reused by recycling or reuse.
  • the pressure-sensitive adhesive adhered to the adherend such as a member is usually peeled off from the adherend by utilizing the re-peelability of the pressure-sensitive adhesive itself.
  • adhesives that require high bonding reliability generally have high adhesive strength to the adherend, and tend to have low removability (removability) from the adherend.
  • the adherend may include a hard brittle member such as glass or a thin member, and such an adherend may be damaged by the force applied when the adhesive is peeled off.
  • Patent Document 1 a technique for achieving both adhesive strength to an adherend and re-peelability, and easily peel off using an aqueous liquid such as water.
  • the present invention has been created in view of the above circumstances, and provides a method for separating a bonded body capable of peeling off the pressure-sensitive adhesive even when the pressure-sensitive adhesive containing a water-affinitive agent is firmly adhered to the member.
  • the purpose is to provide.
  • a method for separating a bonded body including two members bonded by an adhesive is provided.
  • the pressure-sensitive adhesive contains a water-affinitive agent.
  • the above method includes a step of immersing the bonded body in a solvent to peel off the pressure-sensitive adhesive from the member. According to the above method, even if the adhesive is firmly adhered to the member, the adhesive can be peeled off from the member and the bonded body can be separated. For example, when the water-removable adhesive containing a water-affinitive agent cannot be peeled from the member by water-removal using an aqueous liquid due to long-term bonding or the like (that is, when the water-removable adhesive is deactivated).
  • the adhesive can be peeled off. Further, in the peeling by solvent immersion (solvent immersion peeling), since it is not necessary to apply an external force to the member which is the adherend, the member is less likely to be damaged when the adhesive is peeled.
  • two members joined by a pressure-sensitive adhesive means that a pressure-sensitive adhesive is used for at least a part of the joining of two members, and only a specific pressure-sensitive adhesive containing a water-affinitive agent is used. It is not limited to joining by.
  • a pressure-sensitive adhesive is used for at least a part of the joining of two members, and only a specific pressure-sensitive adhesive containing a water-affinitive agent is used. It is not limited to joining by.
  • the two members are joined by a double-sided pressure-sensitive adhesive sheet with a base material, if at least one of the pressure-sensitive adhesives provided on each surface of the double-sided pressure-sensitive adhesive sheet is a water-affinitive-containing pressure-sensitive adhesive, the two.
  • the members shall be interpreted as "bonded by an adhesive".
  • the HSP (Hansen Solubility Parameters) distance between the pressure-sensitive adhesive and the solvent is 4.0 or less.
  • HSP distance By having the above-mentioned relationship (HSP distance) between the pressure-sensitive adhesive to be peeled off and the solvent to be used, peeling by immersion in the solvent proceeds satisfactorily.
  • the solvent preferably contains ethyl acetate. Ethyl acetate is not particularly limited, but is suitable for solvent immersion peeling of an acrylic pressure-sensitive adhesive, for example.
  • the solvent has a hydrogen bond term ( ⁇ H) of 15.0 or more in HSP (Hansen Solubility Parameters).
  • ⁇ H hydrogen bond term
  • HSP Hanes Solubility Parameters
  • the pressure-sensitive adhesive is a solvent-type pressure-sensitive adhesive or an active energy ray-curable pressure-sensitive adhesive.
  • the solvent immersion peeling disclosed herein is suitable for peeling a solvent-type pressure-sensitive adhesive containing a water-affinitive agent and an active energy ray-curable pressure-sensitive adhesive.
  • the two members are joined by a double-sided adhesive pressure-sensitive adhesive sheet containing the pressure-sensitive adhesive.
  • the width of the adhesive sheet is 20 mm or more. According to the solvent immersion peeling disclosed herein, the peeling can proceed satisfactorily with respect to the bonded body bonded with the adhesive sheet having a width of 20 mm or more, and the bonded body can be separated.
  • the method for separating the bonded body is carried out by immersing the bonded body in a solvent for 24 hours or more.
  • the solvent immersion time By setting the solvent immersion time to 24 hours or more, the adhesive is satisfactorily peeled off from the member. For example, after 24 hours have passed from the immersion of the bonded body in the solvent, the distance from which the pressure-sensitive adhesive is peeled off from one of the two members can be 20 mm or more.
  • the method according to some preferred embodiments includes a step of determining whether the pressure-sensitive adhesive can be water-stripping from at least one of the two members before immersing the bonded body in a solvent.
  • the water peeling is a peeling performed in a state where an aqueous liquid is present at a portion where the pressure-sensitive adhesive is peeled from the surface of the member.
  • the bonded body is immersed in a solvent.
  • the method disclosed here was originally capable of peeling from the adherend by water peeling, but is particularly suitable for peeling a water-peeling deactivating adhesive having impaired water-peeling property.
  • the joints separated by the techniques disclosed herein include two members joined by an adhesive.
  • the bonded body 100 according to the embodiment shown in FIG. 1 has a structure in which a first member 120 and a second member 140 are bonded by an adhesive 1.
  • the bonded body 100 is not particularly limited as long as it includes at least two members to be separated, and may be configured to include two or more members.
  • it may be a multi-layer structure in which two or more layered bodies are laminated.
  • the first member 120 and the second member 140 may be in the shape of a sheet or a plate.
  • the above two members may be continuous at a part other than the portion joined by the adhesive.
  • a metal member is used as the first member 120
  • a glass member is used as the second member 140
  • the joint 100 is not limited to this, and the first member 120 and the first member 120 are used.
  • the members 140 of 2 can be in various forms such as a transparent member (for example, at least one of them is a glass member).
  • Adhesive 1 is a pressure-sensitive adhesive containing a water-affinitive agent.
  • the pressure-sensitive adhesive 1 has a sheet-like (adhesive sheet) form, and specifically has a double-sided adhesive baseless double-sided pressure-sensitive adhesive sheet.
  • the pressure-sensitive adhesive 1 can also be said to be layered (that is, a pressure-sensitive adhesive layer).
  • first adhesive surface 1A is adhered to the first member 120
  • second adhesive surface 1B is adhered to the second member 140.
  • the pressure-sensitive adhesive sheet 1 of this embodiment has a width of 20 mm or more and a thickness of 100 ⁇ m or more.
  • the pressure-sensitive adhesive 1 contains a water-affinitive agent, and although it was originally a water-penetrating pressure-sensitive adhesive that can be peeled off from an adherend by water peeling, it is made of water because of its usage history. It is a water-removable deactivating adhesive with impaired peelability. Therefore, the pressure-sensitive adhesive 1 firmly adheres to the first member 120 and the second member 140, and the pressure-sensitive adhesive 1 is removed from the first member 120 and the second member 140 not only by normal peeling but also by water peeling. It is difficult to peel off. Further, it is firmly adhered to the first member 120 and the second member 140 until it is difficult to peel off even by using hot water immersion or ultrasonic vibration. Such an event can occur, for example, when the members are bonded together for a long period of time using the adhesive 1 and the adhesive force is excessively increased.
  • the water peeling property and the water peeling property refer to the ease of peeling and peeling (water peeling property) using an aqueous liquid such as water (water peeling property), and the water peeling property is, for example, , A state in which an aqueous liquid is present on the peeling front (where peeling (separation) starts from the bonding interface between the two) between the adhesive surface of the adhesive (which may be in the form of an adhesive layer or an adhesive sheet) and the surface of the adherend. It means peeling off the adhesive from the adherend.
  • a peeling means by an external force such as manual peeling may be used in combination, or the adhesive may be peeled off only by the solvent dipping peeling.
  • the auxiliary peeling may be performed in a state where the bonded body is immersed in a solvent, or may be performed after the bonded body is taken out of the solvent.
  • the solvent immersion time an appropriate time for the adhesive 1 to peel off from either the first member 120 or the second member 140 is adopted, and the type of the adhesive or the adherend, the adhesive state, the adhesive area, etc. are adopted. It is not limited to a specific range because it depends on the type.
  • the solvent immersion time is, for example, 12 hours or more, preferably 24 hours or more, 48 hours or more, 72 hours or more, 100 hours or more, or 150 hours or more.
  • the solvent immersion time is within one week, preferably 120 hours or less, more preferably 90 hours or less, still more preferably 60 hours or less, and particularly preferably 30 hours or less. Is.
  • the temperature of the solvent is not particularly limited and is usually in the normal temperature range (for example, about 0 ° C to 40 ° C, typically about 10 ° C to 30 ° C), but the solvent is used by heating it to an appropriate temperature. May be good.
  • solvent As the solvent to be used, an appropriate one or two or more kinds of solvents are selected based on the adhesive type, the solvent resistance of the adherend and the like, and the solvent is not limited to a specific kind.
  • the solvent means an organic compound (also referred to as an organic solvent) that is liquid at 23 ° C. and can be used as a solvent or a dispersion medium.
  • one or more solvents having an HSP (Hansen Solubility Parameters) distance of less than or equal to a predetermined value with respect to the pressure-sensitive adhesive to be peeled off by the solvent are preferably used.
  • the HSP distance between the pressure-sensitive adhesive and the solvent is, for example, 20 or less, and may be 15 or less, or 10 or less.
  • solvent immersion peeling tends to proceed satisfactorily.
  • the HSP distance is preferably 8.0 or less (for example, 5.0 or less), and preferably 4.0 or less (for example, 3.0 or less).
  • the lower limit of the HSP distance is usually more than 0, and may be, for example, about 1 or more.
  • the unit of HSP distance is MPa 1/2 .
  • the HSP distance (Ra) between the pressure-sensitive adhesive and the solvent is determined by the following method. That is, the HSP values (dispersion term ( ⁇ D), polarity term ( ⁇ P), hydrogen bond term ( ⁇ H)) of the pressure-sensitive adhesive and the solvent are obtained, and the HSP values ( ⁇ D PSA , ⁇ P PSA , ⁇ H PSA ) of the pressure-sensitive adhesive and the solvent are obtained. Obtain the inter-vector distance of the HSP value ( ⁇ D SOL , ⁇ P SOL , ⁇ H SOL ). This is the HSP distance.
  • Ra [4 ⁇ ( ⁇ D PSA - ⁇ D SOL ) 2 + ( ⁇ P PSA - ⁇ P SOL ) 2 + ( ⁇ H PSA - ⁇ H SOL ) 2 ] 1/2 Is required from.
  • ⁇ D PSA , ⁇ P PSA and ⁇ H PSA represent the dispersion term ( ⁇ D), polarity term ( ⁇ P) and hydrogen bond term ( ⁇ H) of the pressure-sensitive adhesive, respectively, and ⁇ D SOL , ⁇ P SOL and ⁇ H SOL are respectively.
  • the HSP values of the pressure-sensitive adhesive and the solvent can be determined by using the software “HSPiP, Hansen Solubility Parameters in Practice ver4”. can.
  • HSPiP Hansen Solubility Parameters in Practice ver4
  • the pressure-sensitive adhesive and the solvent are composed of a plurality of components, they can be obtained from the molecular group contribution method using the above software. Specifically, each constituent unit in the target substance is input in SMILES notation, and the HSP value ( ⁇ d, ⁇ p, ⁇ h) for each unit is calculated.
  • the HSP value ( ⁇ d, ⁇ p, ⁇ h) of each component of the pressure-sensitive adhesive is calculated based on the above method, and the HSP value of the entire pressure-sensitive adhesive ( ⁇ D PSA , ⁇ P PSA ) is calculated from the mole fraction of each component. , ⁇ H PSA ).
  • ( ⁇ D PSA , ⁇ P PSA , ⁇ H PSA ) [(Mole fraction of ⁇ d a ⁇ a) + (Mole fraction of ⁇ d b ⁇ b) +..., (Mole fraction of ⁇ p a ⁇ a) + ( ⁇ p b ) ⁇ b mole fraction) +..., ( ⁇ h a ⁇ a mole fraction) + ( ⁇ h b ⁇ b mole fraction) +%) Is required from.
  • a and b represent each component of the pressure-sensitive adhesive.
  • one or more solvents having a hydrogen bond term ( ⁇ H) of a predetermined value or more in HSP are preferably used as the solvent.
  • the solvent having a large hydrogen bond term value acts well on the pressure-sensitive adhesive containing a water-affinitive agent, and peeling by immersion in the solvent proceeds well.
  • the ⁇ H of the solvent is, for example, 10.0 or more, 12.0 or more is suitable, preferably 15.0 or more, more preferably 17.0 or more, and may be 20.0 or more.
  • the solvent satisfying the above ⁇ H may have, for example, an HSP distance of more than 5 or more than 10 or even more than 15 with the pressure-sensitive adhesive.
  • the unit of ⁇ H is MPa 1/2 . The above ⁇ H can be obtained from the above-mentioned HSP value calculation method.
  • the solvent examples include alcohols such as methanol, ethanol and isopropyl alcohol (for example, monohydric alcohols having 1 to 4 carbon atoms); aliphatic or alicyclic carbonization such as hexane, heptane, cyclohexane and cycloheptane.
  • alcohols such as methanol, ethanol and isopropyl alcohol (for example, monohydric alcohols having 1 to 4 carbon atoms); aliphatic or alicyclic carbonization such as hexane, heptane, cyclohexane and cycloheptane.
  • Aromatic compounds such as toluene and xylene (specifically, aromatic hydrocarbons); Esters such as methyl acetate, ethyl acetate and butyl acetate; Ketones such as acetone and methyl ethyl ketone; Dimethyl ether, diethyl ether and the like
  • Any one solvent selected from ethers such as butyl methyl ether; alkane halides such as 1,2-dichloroethane; or a mixed solvent of two or more can be used.
  • alcohols, esters and aromatic hydrocarbons are preferable, methanol, ethanol and ethyl acetate are more preferable, and ethyl acetate is particularly preferable.
  • Suitable examples of these solvents are suitable for solvent immersion peeling of, for example, acrylic pressure-sensitive adhesives.
  • the adhesive can be peeled off from the member even if the bonded body is firmly adhered to the adhesive as described above and is usually difficult to peel off by peeling or water peeling. , It is possible to separate (disassemble) the bonded body. According to the above method, the adhesive can be peeled off from the member without damaging the adherend. In addition, the adhesive can be peeled off in one step of solvent immersion and by leaving it alone without requiring an additional operation during solvent immersion, so that it is highly practical.
  • solvent immersion peeling is applied not only to adhesives that are difficult to peel off by normal peeling or water peeling, but also to the water affinity that joins members in various states. Applicable to agent-containing adhesives. According to the solvent immersion peeling disclosed here, the adhesive can be peeled from the member without the need to confirm whether or not the peeling is possible by normal peeling or the like.
  • the above-mentioned solvent immersion peeling peels off the pressure-sensitive adhesive (in other words, the water-peeling deactivating adhesive) that has become difficult to peel off by water peeling as described above from the member. It is effective and suitable for. From this, in the method for separating a bonded body according to a preferred embodiment, before immersing the bonded body in a solvent, water is applied to the pressure-sensitive adhesive from two members (the first member and the second member) bonded by the pressure-sensitive adhesive.
  • a method of immersing the bonded body in a solvent after confirming that water peeling is not possible can be adopted, including a step of determining whether or not peeling is possible (a step of determining water peelability). Whether or not the adhesive is water-stripping from the member is usually difficult to determine from the appearance. Therefore, the determination of the possibility of water peeling may be typically a step of actually attempting to peel off the pressure-sensitive adhesive by water peeling. Since water peeling is defined as described above and will be described in detail later, detailed description thereof will be omitted here.
  • the bonded body separation method disclosed herein is preferably carried out in an embodiment including a step of determining the possibility of water exfoliation. According to the above method, it is possible to efficiently and effectively exfoliate from a member with respect to a water-removable deactivating adhesive whose water releasability is impaired due to long-term bonding or the like.
  • the pressure-sensitive adhesive (typically, a pressure-sensitive adhesive sheet) firmly adhered to the member before the solvent-immersed peeling is usually difficult to peel off from the member by peeling.
  • the adhesive has a force gauge fixed to the end of the member to which the adhesive is bonded in an environment of 23 ° C. and 50% RH, the force gauge is held by hand, and the peeling angle is 90 to 150 degrees. It may be adhered to the above member with an adhesive strength such that the normal peeling force when manually peeled at a speed of 10 to 100 mm / min is 10 N / 20 mm or more.
  • the normal peeling force may be, for example, 15 N / 20 mm or more, 20 N / 20 mm or more, and further 25 N / 20 mm or more (typically 28 N / 20 mm or more).
  • the adhesive that adheres to the member with the above adhesive strength is difficult to peel off from the member that is the adherend by a normal peeling method, or it is difficult to peel off smoothly because the adherend is easily damaged. ..
  • the methods disclosed herein are preferably applied to such pressure-sensitive adhesives.
  • the force gauge the product name "Digital Force Gauge FG-5100" manufactured by Satotec Co., Ltd. or an equivalent product thereof can be used. The same applies to the following water peeling force.
  • the adhesive (typically, an adhesive sheet) firmly adhered to the member before the solvent immersion peeling is difficult to peel off from the member by water peeling.
  • the pressure-sensitive adhesive fixes a force gauge to the end of a member to which the pressure-sensitive adhesive is bonded, holds the force gauge by hand, and adheres from the member which is an adherend.
  • Adhesive strength at which 20 ⁇ L of distilled water is supplied to the part where the agent begins to separate (peeling front), and the water peeling force is 10 N / 20 mm or more when manually peeled at a peeling angle of 90 to 150 degrees and a peeling speed of 10 to 100 mm / min. It may be adhered to the above member.
  • the water peeling force may be, for example, 15 N / 20 mm or more, 20 N / 20 mm or more, and further 25 N / 20 mm or more (typically 28 N / 20 mm or more).
  • the adhesive that adheres to the member with the above adhesive strength is difficult to peel off from the member that is the adherend due to water peeling, or it is difficult to peel off smoothly because the adherend is easily damaged.
  • the methods disclosed herein are particularly suitable for such pressure-sensitive adhesives.
  • Water peeling is defined as described above, and specifically, in the peeling front of the pressure-sensitive adhesive from the member, the water-based liquid is present at the interface between the member and the pressure-sensitive adhesive. A water peeling step of peeling the pressure-sensitive adhesive from the member while advancing the invasion of the aqueous liquid into the interface following the movement.
  • aqueous liquid water or a mixed solvent containing water as a main component and containing a small amount of additives as necessary can be used.
  • a lower alcohol for example, ethyl alcohol
  • a lower ketone for example, acetone
  • the additive a known surfactant or the like can be used.
  • an aqueous liquid that is substantially free of additives may be used. From the viewpoint of environmental hygiene, water is preferably used as the aqueous liquid.
  • the water is not particularly limited, and for example, distilled water, ion-exchanged water, tap water, or the like can be used in consideration of purity, availability, and the like required according to the intended use.
  • the temperature of the aqueous liquid is usually in the range of normal temperature (10 ° C. to 35 ° C.), but hot water having a temperature of 35 ° C. or higher and lower than 90 ° C. (for example, 40 ° C. or higher and 60 ° C. or lower) may be used.
  • the water peeling supplies an aqueous liquid near the outer edge of the pressure-sensitive adhesive (layer) attached to the member, and the water-based liquid is applied from the outer edge of the pressure-sensitive adhesive to the pressure-sensitive adhesive and the member.
  • the peeling of the pressure-sensitive adhesive can proceed without supplying new water (that is, using only the aqueous liquid supplied to the member before the start of peeling). If the water that follows the movement of the peeling front and enters the interface between the adhesive and the member is exhausted in the middle of the water peeling step, it is intermittent or continuous after the start of the water peeling step. Water may be additionally supplied to the water.
  • the amount of the aqueous liquid supplied before the start of peeling is not particularly limited as long as the amount of the aqueous liquid can be introduced into the interface between the adhesive and the member from outside the application range of the adhesive (layer).
  • the amount of the aqueous liquid may be, for example, 5 ⁇ L or more, 10 ⁇ L or more is appropriate, and 20 ⁇ L or more may be used. Further, there is no particular limitation on the upper limit of the amount of the aqueous liquid.
  • the amount of the aqueous liquid may be, for example, 10 mL or less, 5 mL or less, 1 mL or less, 0.5 mL or less, 0.1 mL or less. However, it may be 0.05 mL or less.
  • the operation of allowing the aqueous liquid to enter the interface between the adhesive (layer) and the member from the outer edge of the adhesive at the start of peeling is, for example, the tip of a jig such as a cutter knife or a needle at the interface on the outer edge of the adhesive. , Scratching the outer edge of the adhesive with a hook or claw to lift it, or attaching a strong adhesive tape or suction cup to the back surface near the outer edge of the joint to lift the end of the adhesive. It can be carried out.
  • the water peeling step can be preferably carried out in an embodiment in which the peeling front is moved at a speed of 10 mm / min or more.
  • Moving the peeling front at a speed of 10 mm / min or more corresponds to peeling the pressure-sensitive adhesive (layer) at a tensile speed of 20 mm / min or more, for example, under the condition of a peeling angle of 180 degrees.
  • the speed at which the peeling front is moved may be, for example, 50 mm / min or more, 150 mm / min or more, 300 mm / min or more, or 500 mm / min or more.
  • the upper limit of the speed at which the peeling front is moved is not particularly limited.
  • the speed at which the peel front is moved can be, for example, 1000 mm / min or less.
  • the water peeling disclosed herein is, for example, an embodiment in which the peeling area of the pressure-sensitive adhesive (layer) per 10 ⁇ L of the volume of the aqueous liquid (for example, water) used in the method is, for example, 50 cm 2 or more, preferably 100 cm 2 or more. Can be carried out at.
  • the bonded body disclosed herein is not particularly limited as long as it includes two members bonded by a pressure-sensitive adhesive (typically, a pressure-sensitive adhesive layer), and may be composed of two or more members.
  • a pressure-sensitive adhesive typically, a pressure-sensitive adhesive layer
  • it may be a multi-layer structure in which two or more layered bodies are laminated.
  • Such a bonded body (typically a multilayer structure) may include a display member, an optical member such as a transparent member, and other functional members.
  • the bonded body disclosed here may be a structure used for various uses and products.
  • the bonded body can be a structure for various purposes that may need to be recycled or repaired.
  • a structure constituting various portable devices (portable devices), automobiles, home appliances, etc. it may include two or more members joined by an adhesive. Such joints may be for molding, decoration, protection, support, etc., as well as fixing and joining.
  • the material of the bonded member to be contacted by the pressure-sensitive adhesive and the material constituting at least the surface of the member may be, for example, glass, metal, ceramic material, resin material or the like.
  • a preferred example of the member constituting the bonded body is an optical member.
  • the optical member has optical characteristics (for example, polarization property, light refraction property, light scattering property, light reflection property, light transmission property, light absorption property, photodiffraction property, rotational property, visibility, etc.).
  • optical members include polarizing plates, wavelength plates, retardation plates, optical compensation films, brightness improving films, light guide plates, reflective films, antireflection films, hard coat (HC) films, shock absorbing films, antifouling films, etc.
  • Photochromic film, dimming film, transparent conductive film (ITO film), design film, decorative film, surface protection plate, prism, lens, color filter, transparent substrate, and members in which these are laminated (collectively referred to as these). It may be referred to as a "functional film”).
  • the above-mentioned “plate” and “film” shall include a plate-like, a film-like, a sheet-like form, respectively, and for example, the "polarizing film” shall include a “polarizing plate", a “polarizing sheet” and the like.
  • the optical member may be, for example, a member (typically a display device constituent member) used in a display device (typically an image display device).
  • the optical member is not particularly limited, and examples thereof include a member made of glass, acrylic resin, polycarbonate, polyethylene terephthalate, a metal thin film, or the like (for example, a sheet-shaped, film-shaped, or plate-shaped member).
  • the "optical member” in this specification also includes a member (design film, decorative film, surface protective film, etc.) that plays a role of decoration and protection while maintaining the visibility of the display device.
  • the material constituting at least the surface of the optical member is, for example, glass such as an alkali glass plate or non-alkali glass; a metal material such as stainless steel (SUS) or aluminum; a ceramic material such as alumina or silica; an acrylic resin. It may be a resin material such as ABS resin, polycarbonate resin, polystyrene resin, transparent polyimide resin; or the like.
  • Preferable examples of the member include a member containing an inorganic material such as the above-mentioned glass, the above-mentioned ceramic material, and the above-mentioned metal material.
  • the member may be an optical member in which at least a part of the surface to which the pressure-sensitive adhesive is attached is made of such a material.
  • the members constituting the bonded body are coated surfaces with paints such as acrylic, polyester, alkyd, melamine, urethane, acid-epoxy crosslinked, or composites thereof (for example, acrylic melamine and alkyd melamine). , It may have a plated surface such as a zinc-plated steel plate.
  • the member constituting the bonded body is a glass member containing a brittle material such as glass (typically a hard brittle material).
  • a brittle material such as glass
  • the bonded body separation method disclosed herein is preferably applied to a bonded body in which at least one of two members bonded by an adhesive is made of a brittle material such as a glass material.
  • a hard and brittle material such as glass cannot withstand the force of peeling off the adhesive attached to it and may be damaged.
  • the adhesive can be peeled off from the member without causing damage to the adherend.
  • a typical example of a glass member is a glass plate having a plate shape.
  • the size of the glass member is not limited to a specific range, and the thickness of the glass member (for example, a glass plate) can be, for example, 0.1 to 5 mm (for example, 0.5 to 2 mm).
  • the length of the glass member is, for example, 5 mm to 1 m (for example, 50 mm or more, further 100 mm or more, and 500 mm or less).
  • the method disclosed herein is preferably employed when stripping the pressure-sensitive adhesive from a glass member of such size.
  • the length of the glass member means the length of the portion having the maximum length in the surface direction of the glass member.
  • the surface of the member may be hydrophilized.
  • the surface of the above-mentioned optical member may be treated with a corona treatment, a plasma treatment, a hydrophilic coating treatment for providing a hydrophilic coating layer, or the like, which contributes to the improvement of hydrophilicity.
  • a member or the like having such a hydrophilized surface has improved hydrophilicity and the water contact angle is limited to a predetermined value or less, and is therefore suitable for peeling a pressure-sensitive adhesive containing a water-affinitive agent.
  • the maximum thickness thereof may be about 5 mm or less (for example, 2 mm or less, preferably 1 mm or less).
  • a member having such a maximum thickness is usually easily deformed or damaged by an external force, and by applying the method disclosed herein, the member can be adhered to the member without being damaged.
  • the agent can be peeled off smoothly.
  • the thickness of the member having the plate shape or the sheet shape can usually be, for example, 0.1 to 5 mm (for example, 0.5 to 2 mm).
  • the joints according to some aspects are joints for display devices.
  • the display device include a liquid crystal display device, an organic EL display device, a PDP, an electronic paper, and the like, and in particular, when an expensive member such as a foldable display device and an in-vehicle display device is included, the display device is described here.
  • the disclosed techniques are preferably applied.
  • the display device includes a display device capable of input such as a touch panel. There are strong demands for recycling, reuse, etc. of the above display device, and it is particularly meaningful to apply the technology disclosed here.
  • the display member joined by the adhesive is a member that bears the display function of the display device, and is not particularly limited except for that, and includes, for example, various materials (optical materials, light emitting elements, and the like. ) Can be included.
  • the display member may be, for example, a liquid crystal display panel, an organic EL display panel, a PDP, a touch panel, or the like, or a display unit (display unit) thereof.
  • the panel may be paraphrased as a sheet or a film.
  • the shape of the display member is not particularly limited, and has, for example, a sheet-like or plate-like shape.
  • the display member may have a curved surface shape, or may have deformability or flexibility.
  • Such a display member is suitable as a display member of, for example, a foldable display device or a flexible display device.
  • one is a glass member and the other is a display member.
  • solvent immersion peeling is performed even when the member joined by the adhesive contains a hard and brittle glass member and a display member (for example, a thin member having a thickness of 2 mm or less). By doing so, the two members can be separated without damaging (typically cracking or tearing) the glass member and the display member.
  • the thickness of the display member is not limited to a specific range, and may be, for example, 0.1 to 5 mm (for example, 0.5 to 2 mm).
  • the technique disclosed here is applied to obtain strength due to its thinness. It is effective to separate the members without damaging the display members.
  • the thickness of the display member may be about 50 ⁇ m or less, or may be 30 ⁇ m or less.
  • the joined body to which the members are joined by the adhesive may be one in which a certain period or more has passed since the joining by the adhesive. For example, after the product containing the bonded material is used, until it is collected for recycling, etc., and until the product reaches the end of its product life (for example, 6 months or more, further 1 year or more, or 3 years or more). It can be 5 years or more), and the bonding state with the adhesive can be continued. With such an adhesive, the adhesive strength may be excessively increased due to the usage environment and the like, and it may be difficult to re-peel the adhesive as intended.
  • Products, devices, and structures including the above-mentioned joints are required to have high adhesive reliability due to the adhesive when joining the members, while smooth removal is required when repairing, replacing, inspecting, recycling, etc. of the constituent members.
  • It can be a component of a device (preferably a portable electronic device).
  • a device preferably a portable electronic device.
  • mobile phones, smartphones, tablet computers, laptop computers, various wearable devices for example, wristwear type that is worn on the wrist like a wristwatch, modular type that is worn on a part of the body with clips or straps, glasses type).
  • wearable devices for example, wristwear type that is worn on the wrist like a wristwatch, modular type that is worn on a part of the body with clips or straps, glasses type).
  • the display device may be a component of an electronic device such as a desktop personal computer, a display, or a television (liquid crystal, plasma, organic EL, etc.).
  • "portable” means that it is not enough to be portable, but to have a level of portability that an individual (standard adult) can carry relatively easily. It shall mean.
  • the form of the pressure-sensitive adhesive for joining the members is not particularly limited, and the above-mentioned members may be bonded by a regular or random pattern such as a dot shape or a striped shape, but typically.
  • the pressure-sensitive adhesive is configured as a supportless double-sided pressure-sensitive adhesive sheet composed of a pressure-sensitive adhesive layer, or is configured as a double-sided adhesive pressure-sensitive adhesive sheet (double-sided pressure-sensitive adhesive sheet) having an intermediate layer such as a base material layer. May be good.
  • This pressure-sensitive adhesive sheet has a structure in which a first pressure-sensitive adhesive layer and a second pressure-sensitive adhesive layer are provided on each surface (both non-peelable) of the intermediate layer.
  • the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet is not limited to a single-layer structure, and may further include one or more pressure-sensitive adhesive layers having the same or different composition.
  • the intermediate layer may be a pressure-sensitive adhesive layer, in which case the pressure-sensitive adhesive sheet is intermediate with the first and second pressure-sensitive adhesive layers constituting the surface of the pressure-sensitive adhesive sheet. It may have at least three pressure-sensitive adhesive layers, including a pressure-sensitive adhesive layer as a layer.
  • the pressure-sensitive adhesive (which may be in the form of a pressure-sensitive adhesive layer or a pressure-sensitive adhesive sheet; the same shall apply hereinafter unless otherwise specified) may be, for example, an acrylic pressure-sensitive adhesive or a rubber-based pressure-sensitive adhesive (natural).
  • Various known adhesives such as rubber-based, synthetic rubber-based, mixed systems, etc.), silicone-based adhesives, polyester-based adhesives, urethane-based adhesives, polyether-based adhesives, polyamide-based adhesives, fluorine-based adhesives, etc.
  • It may be a pressure-sensitive adhesive composed of one type or two or more types of pressure-sensitive adhesives selected from the agents.
  • the acrylic pressure-sensitive adhesive refers to a pressure-sensitive adhesive containing an acrylic polymer as a main component (base polymer). The same meaning applies to rubber-based pressure-sensitive adhesives and other pressure-sensitive adhesives.
  • the “base polymer” of the pressure-sensitive adhesive refers to the main component of the rubber-like polymer contained in the pressure-sensitive adhesive, and is not interpreted in a limited manner other than this.
  • the rubber-like polymer refers to a polymer that exhibits rubber elasticity in a temperature range near room temperature.
  • the "main component” means a component contained in the largest proportion among the contained components on a weight basis. Therefore, for example, when the pressure-sensitive adhesive is composed of three or more components, the content of the main component in the pressure-sensitive adhesive may be 34% by weight or more.
  • the "acrylic polymer” refers to a polymer derived from a monomer component containing an acrylic monomer in an amount of more than 50% by weight, and is also referred to as an acrylic polymer.
  • the acrylic monomer refers to a monomer derived from a monomer having at least one (meth) acryloyl group in one molecule.
  • (meth) acryloyl means a comprehensively referring to acryloyl and methacryloyl.
  • (meth) acrylate” means acrylate and methacrylate
  • “(meth) acrylic” means acrylic and methacrylic, respectively.
  • an acrylic pressure-sensitive adhesive may be preferably used as the constituent material of the pressure-sensitive adhesive.
  • the pressure-sensitive adhesive disclosed herein may be an acrylic pressure-sensitive adhesive containing an acrylic polymer.
  • Acrylic adhesives tend to have excellent transparency, weather resistance, and design freedom. Acrylic adhesives having high transparency are preferably used for optical applications and, by extension, bonding applications for display devices.
  • the pressure-sensitive adhesive disclosed herein contains, for example, a (meth) acrylic acid alkyl ester having a linear or branched alkyl group having 1 to 20 carbon atoms at the ester terminal in a proportion of 33% by weight or more.
  • a (meth) acrylic acid alkyl ester having an alkyl group having an number of carbon atoms of X or more and Y or less at the ester terminal may be referred to as “(meth) acrylic acid CXY alkyl ester”.
  • the proportion of the (meth) acrylic acid C 1-20 alkyl ester in the total monomer components of the acrylic polymer is, for example, 35% by weight or more, and 50% by weight. % Or more is appropriate, and may be 55% by weight or more.
  • the proportion of the (meth) acrylic acid C 1-20 alkyl ester in the above-mentioned monomer components may be, for example, 99.9% by weight or less, 99% by weight or less, or 95% by weight or less.
  • the ratio of the C 1-20 (meth) acrylic acid alkyl ester to the total monomer component of the acrylic polymer may be, for example, 85% by weight or less from the viewpoint of the cohesiveness of the pressure-sensitive adhesive. , 75% by weight or less, or 65% by weight or less.
  • the (meth) acrylic acid C 1-20 alkyl ester can be used alone or in combination of two or more.
  • At least (meth) acrylic acid C 4-20 alkyl ester it is preferable to use at least (meth) acrylic acid C 4-18 alkyl ester.
  • the (meth) acrylic acid C 4-18 alkyl ester can be used alone or in combination of two or more.
  • the monomer component constituting the acrylic polymer contains a (meth) acrylic acid alkyl ester and, if necessary, another monomer (copolymerizable monomer) copolymerizable with the (meth) acrylic acid alkyl ester.
  • a monomer having a polar group for example, a carboxy group, a hydroxyl group, a ring containing a nitrogen atom, etc.
  • a monomer having a relatively high glass transition temperature of a homopolymer for example, 10 ° C. or higher
  • Monomers having polar groups can be useful for introducing cross-linking points in acrylic polymers and enhancing the cohesive force of adhesives.
  • the copolymerizable monomer may be used alone or in combination of two or more.
  • Non-limiting examples of copolymerizable monomers include carboxy group-containing monomers, acid anhydride group-containing monomers, hydroxyl group-containing monomers, sulfonic acid groups or phosphate group-containing monomers, epoxy group-containing monomers, and cyano group-containing monomers.
  • Isocyanate group-containing monomer Isocyanate group-containing monomer, amide group-containing monomer, amino group-containing monomer, nitrogen atom-containing ring-containing monomer, succinimide skeleton-containing monomer, maleimides, (meth) acrylic acid aminoalkyls, alkoxy group-containing monomer, alkoxysilyl group Containing monomers, vinyl esters, vinyl ethers, aromatic vinyl compounds, olefins, (meth) acrylic acid esters having alicyclic hydrocarbon groups, (meth) acrylic acid esters having aromatic hydrocarbon groups, etc.
  • Heterocyclic ring-containing (meth) acrylate such as tetrahydrofurfuryl acrylate, halogen atom-containing (meth) acrylate such as vinyl chloride and fluorine atom-containing (meth) acrylate, and silicon atom-containing (meth) such as silicone (meth) acrylate.
  • examples thereof include (meth) acrylic acid esters obtained from acrylates and terpene compound derivative alcohols. Of these, a carboxy group-containing monomer, a hydroxyl group-containing monomer, a monomer having a nitrogen atom-containing ring, and a (meth) acrylic acid ester having an alicyclic hydrocarbon group are preferable.
  • the copolymerizable monomer examples include acrylic acid, methacrylic acid, carboxyethyl acrylate, carboxypentyl acrylate, itaconic acid, maleic acid, fumaric acid, crotonic acid, isocrotonic acid and the like.
  • the hydroxyl group-containing monomer examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, and (meth).
  • Examples of the monomer having a nitrogen atom-containing ring include N-vinyl-2-pyrrolidone, N-methylvinylpyrrolidone, N-vinylpyridine, N-vinylpiperidone, N-vinylpyrimidine, N-vinylpiperazine, and N-vinylpyrazine.
  • N-vinyl-2-caprolactam N-vinyl-1,3-oxadin-2-one, N-vinyl-3,5-morpholindione
  • N-vinylpyrazole N-vinylisoxazole
  • N -Vinylthiazole N-vinylisothyazole
  • N-vinylpyridazine and the like lactams such as N-vinyl-2-caprolactam
  • Examples of the (meth) acrylic acid ester having an alicyclic hydrocarbon group include cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, and adamantyl (meth).
  • Examples thereof include alicyclic hydrocarbon group-containing (meth) acrylates such as acrylates.
  • the amount used is not particularly limited, and for example, it is appropriate to use 0.01% by weight or more of the total monomer component. From the viewpoint of better exerting the effect of using the copolymerizable monomer, the amount of the copolymerizable monomer used may be 0.1% by weight or more of the entire monomer component, or 0.5% by weight or more. Further, from the viewpoint of facilitating the balance of adhesive properties, it is appropriate that the amount of the copolymerizable monomer used is 60% by weight or less of the entire monomer component, and may be 50% by weight or less, or 40% by weight. It may be less than%.
  • the monomer component constituting the acrylic polymer may contain a hydroxyl group-containing monomer.
  • the hydroxyl group-containing monomer By using the hydroxyl group-containing monomer, the cohesive force of the pressure-sensitive adhesive and the degree of cross-linking (for example, cross-linking with an isocyanate cross-linking agent) can be suitably adjusted.
  • the hydroxyl group-containing monomer those exemplified above can be used, and for example, 2-hydroxyethyl acrylate (HEA) or 4-hydroxybutyl acrylate (4HBA) can be preferably adopted.
  • the hydroxyl group-containing monomer may be used alone or in combination of two or more.
  • the amount used when the hydroxyl group-containing monomer is used is not particularly limited, and in some preferred embodiments, the amount of the hydroxyl group-containing monomer used is 15% by weight or more of the total monomer component, and 20% by weight or more is appropriate. It is preferably 25% by weight or more. Further, from the viewpoint of suppressing the water absorption of the pressure-sensitive adhesive, it is appropriate that the amount of the hydroxyl group-containing monomer used is, for example, 50% by weight or less (for example, 45% by weight or less) of the entire monomer component in some embodiments. , 40% by weight or less, 30% by weight or less, or 20% by weight or less.
  • the monomer component constituting the acrylic polymer may contain an alicyclic hydrocarbon group-containing (meth) acrylate.
  • an alicyclic hydrocarbon group-containing (meth) acrylate these exemplified above can be used, and for example, cyclohexyl acrylate (CHA) or isobornyl acrylate can be preferably adopted.
  • the alicyclic hydrocarbon group-containing (meth) acrylate may be used alone or in combination of two or more.
  • the amount used is not particularly limited, and may be, for example, 1% by weight or more, 5% by weight or more, or even 10% by weight or more of the entire monomer component. good.
  • the upper limit of the amount of the alicyclic hydrocarbon group-containing (meth) acrylate used is appropriately about 40% by weight or less, and may be 25% by weight or less (for example, 15% by weight or less).
  • the monomer component constituting the acrylic polymer may contain a monomer having a nitrogen atom.
  • a monomer having a nitrogen atom those exemplified above can be used.
  • the monomer having a nitrogen atom include a monomer having a nitrogen atom-containing ring.
  • N-vinyl cyclic amide can be mentioned, and among them, N-vinyl-2-pyrrolidone can be preferably adopted.
  • the monomer having a nitrogen atom can be used alone or in combination of two or more.
  • the amount of the monomer having a nitrogen atom is not particularly limited, and may be, for example, 1% by weight or more or 5% by weight or more of the entire monomer component. Further, it can be 10% by weight or more. Further, it is appropriate that the amount of the monomer having a nitrogen atom used is, for example, 40% by weight or less of the total monomer component, 30% by weight or less, or 15% by weight or less.
  • the proportion of the carboxy group-containing monomer in the monomer component of the acrylic polymer may be, for example, less than 10% by weight, less than 3% by weight, or less than 1% by weight (eg, 0.1% by weight). %) May be used. It is not necessary to substantially use a carboxy group-containing monomer as a monomer component of the acrylic polymer.
  • the fact that the carboxy group-containing monomer is not substantially used means that the carboxy group-containing monomer is not used at least intentionally.
  • Acrylic polymers having such a composition can have metal corrosion inhibitory properties for adherends containing metals.
  • the composition of the monomer component constituting the acrylic polymer can be set so that the glass transition temperature Tg obtained by the Fox formula based on the composition of the monomer component is ⁇ 75 ° C. or higher and 10 ° C. or lower.
  • the Tg is preferably 0 ° C. or lower, preferably ⁇ 10 ° C. or lower, and preferably ⁇ 20 ° C. or lower or ⁇ 30 ° C. or lower, from the viewpoint of adhesive strength and the like. May be good.
  • the Tg may be, for example, ⁇ 60 ° C. or higher, ⁇ 50 ° C. or higher, ⁇ 45 ° C. or higher, or ⁇ 40 ° C. or higher.
  • Tg is the glass transition temperature (unit: K) of the copolymer
  • Wi is the weight fraction of the monomer i in the copolymer (copolymerization ratio based on the weight)
  • Tgi is the monomer i.
  • the glass transition temperature of the homopolymer used for calculating Tg As the glass transition temperature of the homopolymer used for calculating Tg, the numerical values described in publicly known materials, specifically, "Polymer Handbook” (3rd edition, John Wiley & Sons, Inc., 1989) shall be used. .. When multiple types of values are described in this document, the highest value is adopted.
  • thermal polymerization initiator In the polymerization, a known or commonly used thermal polymerization initiator or photopolymerization initiator may be used depending on the polymerization method, polymerization mode and the like.
  • the thermal polymerization initiator is not particularly limited, but is, for example, an azo-based polymerization initiator, a peroxide-based initiator, a redox-based initiator by a combination of a peroxide and a reducing agent, and a substituted ethane-based initiator. Etc. can be used.
  • the photopolymerization initiator is not particularly limited, but is, for example, a ketal-based photopolymerization initiator, an acetophenone-based photopolymerization initiator, a benzoin ether-based photopolymerization initiator, an acylphosphine oxide-based photopolymerization initiator, ⁇ -.
  • Ketol-based photopolymerization initiator aromatic sulfonyl chloride-based photopolymerization initiator, photoactive oxime-based photopolymerization initiator, benzoin-based photopolymerization initiator, benzyl-based photopolymerization initiator, benzophenone-based photopolymerization initiator, thioxanthone-based light
  • a polymerization initiator or the like can be used.
  • the polymerization initiator one type may be used alone or two or more types may be used in combination as appropriate.
  • the amount of such a thermal polymerization initiator or photopolymerization initiator used can be a normal amount depending on the polymerization method, polymerization mode, etc., and is not particularly limited.
  • polymerization initiator typically about 0.01 to 2 parts by weight, for example, about 0.01 to 1 part by weight
  • the polymerization initiator typically about 0.01 to 2 parts by weight, for example, about 0.01 to 1 part by weight
  • chain transfer agents which can also be grasped as a molecular weight adjusting agent or a degree of polymerization adjusting agent
  • chain transfer agent mercaptans such as n-dodecyl mercaptan, t-dodecyl mercaptan, thioglycolic acid, and ⁇ -thioglycerol
  • a chain transfer agent containing no sulfur atom non-sulfur chain transfer agent
  • the chain transfer agent may be used alone or in combination of two or more. When a chain transfer agent is used, the amount used may be, for example, about 0.01 to 1 part by weight with respect to 100 parts by weight of the monomer component.
  • the techniques disclosed herein may also be preferably practiced in embodiments that do not use chain transfer agents.
  • the molecular weight of the acrylic polymer obtained by appropriately adopting the above-mentioned various polymerization methods is not particularly limited, and can be set in an appropriate range according to the required performance.
  • the weight average molecular weight (Mw) of the acrylic polymer is, for example, about 10 ⁇ 104 or more, and it is appropriate to make it over 30 ⁇ 10 4 from the viewpoint of achieving both cohesive force and adhesive force in a well-balanced manner.
  • the acrylic polymer according to some embodiments preferably has a Mw of approximately 50 ⁇ 104 or more.
  • the upper limit of Mw of the acrylic polymer may be approximately 500 ⁇ 10 4 or less (for example, approximately 150 ⁇ 104 or less).
  • the above Mw may be approximately 75 ⁇ 104 or less.
  • Mw means a value in terms of standard polystyrene obtained by gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • the model name “HLC-8320GPC” column: TSKgelGMH-H (S), manufactured by Tosoh Corporation
  • S gel permeation chromatography
  • the pressure-sensitive adhesive disclosed herein is a pressure-sensitive adhesive containing a monomer component having the above-mentioned composition in the form of a polymer, an unpolymerized product (that is, a form in which a polymerizable functional group is unreacted), or a mixture thereof. It can be formed using the composition.
  • the pressure-sensitive adhesive composition includes a water-dispersed pressure-sensitive adhesive composition in which a pressure-sensitive adhesive (adhesive component) is dispersed in water, a solvent-type pressure-sensitive adhesive composition in which the pressure-sensitive adhesive is contained in an organic solvent, ultraviolet rays, radiation, and the like.
  • An active energy ray-curable pressure-sensitive adhesive composition prepared to be cured by active energy rays to form a pressure-sensitive adhesive, a hot-melt type pressure-sensitive adhesive that is applied in a heat-melted state and forms a pressure-sensitive adhesive when cooled to near room temperature. It can be in various forms such as a composition.
  • the pressure-sensitive adhesive composition according to some embodiments is a solvent-type pressure-sensitive adhesive composition or a solvent-free type pressure-sensitive adhesive composition.
  • the solvent-free pressure-sensitive adhesive composition includes an active energy ray-curable pressure-sensitive adhesive composition and a hot-melt type pressure-sensitive adhesive composition.
  • the peeling by solvent immersion disclosed herein is an active energy ray formed from a solvent type pressure-sensitive adhesive formed from a solvent-type pressure-sensitive adhesive composition and an active energy ray (typically ultraviolet hard) curable pressure-sensitive adhesive composition. It is effective against curable adhesives (typically UV curable adhesives).
  • the pressure-sensitive adhesive composition may be an active energy ray-curable pressure-sensitive adhesive composition.
  • active energy ray refers to an energy ray having energy that can cause a chemical reaction such as a polymerization reaction, a cross-linking reaction, or decomposition of an initiator.
  • active energy rays include light such as ultraviolet rays, visible rays and infrared rays, and radiation such as ⁇ rays, ⁇ rays, ⁇ rays, electron beams, neutron rays and X-rays.
  • a photocurable pressure-sensitive adhesive composition is mentioned as a preferable example of the active energy ray-curable pressure-sensitive adhesive composition.
  • the photocurable pressure-sensitive adhesive composition has an advantage that even a thick pressure-sensitive adhesive layer can be easily formed. Of these, an ultraviolet curable pressure-sensitive adhesive composition is preferable.
  • the photocurable pressure-sensitive adhesive composition typically contains at least a portion of the monomer component of the composition (which may be part of the type of monomer or part of the amount). Included in the form of a polymer.
  • the polymerization method for forming the above-mentioned polymer is not particularly limited, and various conventionally known polymerization methods can be appropriately adopted. For example, thermal polymerization such as solution polymerization, emulsion polymerization, bulk polymerization (typically performed in the presence of a thermal polymerization initiator); photopolymerization performed by irradiating light such as ultraviolet rays (typically).
  • Radiation polymerization carried out by irradiating radiation such as ⁇ -rays and ⁇ -rays; which is carried out in the presence of a photopolymerization initiator; and the like can be appropriately adopted. Of these, photopolymerization is preferable.
  • the photocurable pressure-sensitive adhesive composition contains a partial polymer of a monomer component (for example, an acrylic partial polymer).
  • a partial polymer is typically a mixture of a polymer derived from a monomer component and an unreacted monomer, and preferably exhibits a syrup-like (viscous liquid) form.
  • the partial polymer having such properties may be referred to as "monomer syrup” or simply "syrup".
  • the polymerization method for partially polymerizing the monomer component is not particularly limited, and various polymerization methods as described above can be appropriately selected and used. From the viewpoint of efficiency and convenience, the photopolymerization method can be preferably adopted. According to photopolymerization, the polymerization conversion rate (monomer conversion) of the monomer component can be easily controlled by the polymerization conditions such as the irradiation amount of light (light amount).
  • the polymerization conversion rate of the monomer mixture in the above partial polymer is not particularly limited.
  • the polymerization conversion rate can be, for example, about 70% by weight or less, and from the viewpoint of ease of preparation, coatability, etc. of the pressure-sensitive adhesive composition containing the partial polymer, about 50% by weight or less is appropriate. , Approximately 40% by weight or less is preferable.
  • the lower limit of the polymerization conversion rate is not particularly limited, but is typically about 1% by weight or more, and it is appropriate to make it about 5% by weight or more.
  • the pressure-sensitive adhesive composition containing the above partial polymer other components (for example, a photopolymerization initiator, a water affinity agent as described later, a cross-linking agent, a polyfunctional monomer, an acrylic oligomer) used as necessary may be used.
  • Adhesive-imparting resin, silane coupling agent, etc. can be blended.
  • the method of blending such other components is not particularly limited, and may be contained in the monomer mixture in advance or added to the partial polymer, for example.
  • the pressure-sensitive adhesive is a pressure-sensitive adhesive formed from a water-dispersible pressure-sensitive adhesive composition.
  • a typical example of the water-dispersed pressure-sensitive adhesive composition is an emulsion-type pressure-sensitive adhesive composition.
  • Emulsion-type pressure-sensitive adhesive compositions typically contain a polymer of monomeric components and, optionally, additives. Emulsion polymerization of the monomer components is usually carried out in the presence of an emulsifier. According to emulsion polymerization, a polymerization reaction solution in the form of an emulsion in which a polymer of a monomer component is dispersed in water can be obtained.
  • the water-dispersed pressure-sensitive adhesive composition used for forming the pressure-sensitive adhesive can be preferably produced by using the above-mentioned polymerization reaction solution.
  • the emulsifier for emulsion polymerization is not particularly limited, and known anionic emulsifiers, nonionic emulsifiers and the like can be used.
  • the emulsifier may be used alone or in combination of two or more.
  • anionic emulsifiers include sodium lauryl sulfate, ammonium lauryl sulfate, sodium dodecylbenzene sulfonate, sodium polyoxyethylene lauryl sulfate, sodium polyoxyethylene alkyl ether sulfate, ammonium polyoxyethylene alkyl phenyl ether sulfate, and polyoxy.
  • Non-limiting examples of nonionic emulsifiers include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyoxyethylene fatty acid esters, polyoxyethylene polyoxypropylene block polymers and the like.
  • An emulsifier having a reactive functional group may be used.
  • the reactive emulsifier examples include a radically polymerizable emulsifier having a structure in which a radically polymerizable functional group such as a propenyl group or an allyl ether group is introduced into the above-mentioned anionic emulsifier or nonionic emulsifier.
  • the amount of the emulsifier used in the emulsion polymerization may be, for example, 0.2 parts by weight or more, 0.5 parts by weight or more, or 1.0 part by weight or more with respect to 100 parts by weight of the monomer component. It may be 5 parts by weight or more. Further, from the viewpoint of improving the water adhesion resistance or the transparency of the pressure-sensitive adhesive, it is appropriate that the amount of the emulsifier used is 10 parts by weight or less with respect to 100 parts by weight of the monomer component in some embodiments. It is preferably 5 parts by weight or less, and may be 3 parts by weight or less.
  • the emulsifier used here for emulsion polymerization can also function as a water affinity agent described later.
  • the pressure-sensitive adhesive composition may be a solvent-type pressure-sensitive adhesive composition.
  • the solvent-based pressure-sensitive adhesive composition typically contains a solution polymer of the monomer components and an additive (eg, a water-affinitive) used as needed.
  • the solvent (polymerization solvent) used for solution polymerization can be appropriately selected from conventionally known organic solvents (for example, toluene, ethyl acetate, etc.).
  • a polymerization reaction solution in which the polymer of the monomer component is dissolved in the polymerization solvent can be obtained.
  • the solvent-based pressure-sensitive adhesive composition disclosed herein can be preferably produced using the above-mentioned polymerization reaction solution.
  • the pressure-sensitive adhesive contains a water-affinitive agent.
  • a water-affinitive agent in the pressure-sensitive adhesive, it is usually possible to effectively reduce the peeling force by utilizing an aqueous liquid such as water, and the water-peeling property is improved.
  • the reason is not particularly limited, but in general, the water-affinitive agent tends to be unevenly distributed on the surface of the pressure-sensitive adhesive due to having a hydrophilic region, thereby efficiently enhancing the water affinity of the surface of the pressure-sensitive adhesive. Is exhibited, and it is considered that the peeling force is effectively reduced when the pressure-sensitive adhesive comes into contact with water, and the water peeling property is improved.
  • the pressure-sensitive adhesive that joins the members in the above-mentioned bonded body does not exhibit the water peelability originally possessed by the pressure-sensitive adhesive due to circumstances such as being used for a long period of time, and water that is difficult to peel off by water peeling. It may be a peelable deactivating adhesive. Even with such a water-affinitive-containing pressure-sensitive adhesive having deactivated water-removability, the pressure-sensitive adhesive can be peeled off from the member to which the pressure-sensitive adhesive is bonded by applying the technique disclosed herein.
  • the hydrophilic agent is typically contained in the pressure-sensitive adhesive composition (and thus the pressure-sensitive adhesive) in free form.
  • water-affinitive agent one that is liquid at room temperature (about 25 ° C.) can be preferably used from the viewpoint of ease of preparation of the pressure-sensitive adhesive composition and the like.
  • the hydrophilic agent may be used alone or in combination of two or more.
  • the HLB of the water-affinitive agent is not particularly limited, for example, 3.0 or more, about 5.0 or more is suitable, preferably 8.0 or more, and more preferably 10 or more. , More preferably 13 or more (for example, 15 or more).
  • a water-affinitive having an HLB in the above range in a pressure-sensitive adhesive for example, a pressure-sensitive adhesive containing an acrylic polymer
  • the upper limit of the HLB is 20 or less, for example, 18 or less, or 16 or less (for example, 15 or less).
  • the HLB in the present specification is Hydrophilic-Lipophile Balance by Griffin, which is a value indicating the degree of affinity of the surfactant with water or oil, and the ratio of hydrophilicity to lipophilicity is between 0 and 20. It is expressed by the numerical value of.
  • the definition of HLB is W. C. Griffin: J. Soc. Cosmetic Chemists, 1,311 (1949), Koshimin Takahashi, Yoshiro Namba, Motoo Koike, Masao Kobayashi, "Surfactant Handbook", 3rd edition, published by Engineering Books, November 25, 1972, p179- As described in 182 and the like.
  • the hydrophilic agent having the HLB can be selected based on the common general knowledge of those skilled in the art by referring to the above references as necessary.
  • the hydrophilic agent at least one compound selected from a surfactant and a compound having a polyoxyalkylene skeleton can be used.
  • a surfactant and a compound having a polyoxyalkylene skeleton one or more of known surfactants and compounds having a polyoxyalkylene skeleton can be used without particular limitation. Needless to say, among the above-mentioned surfactants, there are compounds having a polyoxyalkylene skeleton, and vice versa.
  • nonionic surfactants As the surfactant that can be used as a water-affinitive agent, known nonionic surfactants, anionic surfactants, cationic surfactants and the like can be used. Of these, nonionic surfactants are preferable.
  • the surfactant may be used alone or in combination of two or more.
  • nonionic surfactants are polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether; polyoxyethylene octylphenyl ether, poly.
  • Polyoxyethylene alkyl phenyl ethers such as oxyethylene nonylphenyl ether; sorbitan fatty acid esters such as sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate; polyoxyethylene sorbitan monolaurate, polyoxyethylene Polyoxyethylene sorbitan such as sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan tristearate, polyoxyethylene sorbitan triisostearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan trioleate Examples thereof include fatty acid esters; polyoxyethylene glyceryl ether fatty acid esters; polyoxyelene-polyoxypropylene block copolymers; and the like. These nonionic surfactants can be used alone or in combination of two or more.
  • anionic surfactants include alkyl sulfates such as lauryl sulfate and octadecyl sulfate; fatty acid salts; alkylbenzene sulfonates such as nonylbenzene sulfonate and dodecylbenzene sulfonate; dodecylnaphthalene sulfonate and the like.
  • the salt may be, for example, a metal salt such as a sodium salt, a potassium salt, a calcium salt or a magnesium salt (preferably a monovalent metal salt), an ammonium salt, an amine salt or the like. Can be.
  • a metal salt such as a sodium salt, a potassium salt, a calcium salt or a magnesium salt (preferably a monovalent metal salt), an ammonium salt, an amine salt or the like.
  • a metal salt such as a sodium salt, a potassium salt, a calcium salt or a magnesium salt (preferably a monovalent metal salt), an ammonium salt, an amine salt or the like.
  • a metal salt such as a sodium salt, a potassium salt, a calcium salt or a magnesium salt (preferably a monovalent metal salt), an ammonium salt, an amine salt or the like.
  • a metal salt such as a sodium salt, a potassium salt, a calcium salt or a magnesium salt (preferably a monovalent metal salt), an ammonium salt, an amine
  • Examples of the compound having a polyoxyalkylene skeleton that can be used as a water affinity include polyalkylene glycols such as polyethylene glycol (PEG) and polypropylene glycol (PPG); polyethers containing polyoxyethylene units, and polyoxypropylene units.
  • Polyethylene containing, a compound containing oxyethylene units and oxypropylene units (the sequence of these units may be random or block-like); derivatives thereof; etc. can be used.
  • compounds having a polyoxyalkylene skeleton can also be used. These can be used alone or in combination of two or more. Among them, it is preferable to use a compound containing a polyoxyethylene skeleton (also referred to as a polyoxyethylene segment), and PEG is more preferable.
  • the molecular weight (chemical formula amount) of the compound having a polyoxyalkylene skeleton is not particularly limited, and it is appropriate that the compound has a polyoxyalkylene skeleton, for example, less than 1000, and is about 600 or less (for example, from the viewpoint of preparation of the pressure-sensitive adhesive composition). 500 or less) is preferable.
  • the lower limit of the molecular weight of the compound having a polyoxyalkylene skeleton is not particularly limited, and a compound having a molecular weight of about 100 or more (for example, about 200 or more, further about 300 or more) is preferably used.
  • the content of the water-affinitive agent in the pressure-sensitive adhesive is not particularly limited, and can be set so that the effect of using the water-affinitive agent is appropriately exhibited.
  • the content of the water affinity can be, for example, 0.001 part by weight or more per 100 parts by weight of the polymer (for example, acrylic polymer) contained in the pressure-sensitive adhesive, and is 0.01 weight by weight.
  • the amount is preferably 0.05 parts by weight or more, more preferably 0.1 parts by weight or more, and more preferably 0.1 parts by weight or more.
  • the content of the hydrophilic agent may be, for example, 1.0 part by weight or more, or 1.5 parts by weight or more, based on 100 parts by weight of the polymer contained in the pressure-sensitive adhesive.
  • the amount of the water-affinitive agent used can be approximately 3 parts by weight or less with respect to 100 parts by weight of the polymer, and it is appropriate that the amount is approximately 2 parts by weight or less. It is preferably less than 1 part by weight, more preferably less than 0.5 part by weight.
  • the pressure-sensitive adhesive containing the limited amount of the water-affinitive agent can preferably achieve both adhesive strength and solvent immersion peelability. In optical applications, it can further have optical characteristics.
  • a polyfunctional monomer can be used in the pressure-sensitive adhesive composition (and thus the pressure-sensitive adhesive), if necessary. Polyfunctional monomers can serve purposes such as adjusting cohesive force.
  • the polyfunctional monomer forms a crosslinked structure having appropriate flexibility by reacting the ethylenically unsaturated group with light (for example, ultraviolet rays) irradiation at the time of forming the pressure-sensitive adhesive layer or after being attached to the adherend. Can be. Therefore, in the present specification, the "polyfunctional monomer” can be paraphrased as a cross-linking agent.
  • a polyfunctional monomer may be preferably used.
  • As the polyfunctional monomer a compound having two or more ethylenically unsaturated groups can be used.
  • the polyfunctional monomer may be used alone or in combination of two or more.
  • Examples of the ethylenically unsaturated group contained in the polyfunctional monomer include, but are not limited to, an acryloyl group, a methacryloyl group, a vinyl group and an allylic group.
  • Preferred ethylenically unsaturated groups from the viewpoint of photoreactivity include acryloyl group and methacryloyl group. Of these, the acryloyl group is preferable.
  • polyfunctional monomers examples include ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, and neopentyl glycol di (meth).
  • the amount of the polyfunctional monomer used varies depending on its molecular weight, the number of functional groups, etc., but for example, a monomer component (typically, an acrylic polymer or a monomer component of the polymer) that forms a polymer contained in a pressure-sensitive adhesive. ) It is appropriate that the range is about 0.01 parts by weight to 3.0 parts by weight with respect to 100 parts by weight.
  • the pressure-sensitive adhesive composition disclosed herein may contain a cross-linking agent, if necessary, mainly for the purpose of cross-linking within the pressure-sensitive adhesive (layer) or cross-linking the pressure-sensitive adhesive and its adjacent surface.
  • the type of the cross-linking agent is not particularly limited, and the cross-linking agent is selected from the conventionally known cross-linking agents so as to exhibit an appropriate cross-linking function in the pressure-sensitive adhesive, for example, depending on the composition of the pressure-sensitive adhesive composition. Can be done.
  • cross-linking agent examples include an isocyanate-based cross-linking agent, an epoxy-based cross-linking agent, an oxazoline-based cross-linking agent, an aziridine-based cross-linking agent, a carbodiimide-based cross-linking agent, a melamine-based cross-linking agent, a urea-based cross-linking agent, a metal alkoxide-based cross-linking agent, and a metal.
  • examples thereof include a chelate-based cross-linking agent, a metal salt-based cross-linking agent, a hydrazine-based cross-linking agent, and an amine-based cross-linking agent. These can be used alone or in combination of two or more.
  • the content of the cross-linking agent (when two or more kinds of cross-linking agents are contained, the total amount thereof) is not particularly limited.
  • the content of the cross-linking agent is a monomer component (for example, an acrylic polymer or the said) that forms a polymer contained in the pressure-sensitive adhesive. It is appropriate that the amount is about 5 parts by weight or less with respect to 100 parts by weight of the monomer component of the polymer, preferably about 0.001 to 5 parts by weight, and about 0.001 to 4 parts by weight. It is more preferable, and it is more preferable that the amount is about 0.001 to 3 parts by weight.
  • the pressure-sensitive adhesive composition may be a pressure-sensitive adhesive composition containing no cross-linking agent as described above.
  • the pressure-sensitive adhesive composition may be substantially free of a cross-linking agent such as an isocyanate-based cross-linking agent.
  • a cross-linking agent such as an isocyanate-based cross-linking agent
  • the fact that the pressure-sensitive adhesive composition does not substantially contain a cross-linking agent means that the amount of the cross-linking agent with respect to 100 parts by weight of the above-mentioned monomer component is less than 0.05 parts by weight (for example, 0. It means that it is less than 01 parts by weight).
  • a cross-linking catalyst may be used to allow the cross-linking reaction to proceed more effectively.
  • the pressure-sensitive adhesive composition used for forming the pressure-sensitive adhesive may contain a cross-linking retarder (for example, a compound that causes keto-enol tautomerism), if desired.
  • the amount of the cross-linking catalyst and the cross-linking retarder used is not limited to a specific range, and an appropriate amount is used depending on the purpose and the like.
  • the pressure-sensitive adhesive may contain a tack-imparting resin.
  • the tackifier resin include a rosin-based tackifier resin, a rosin derivative tackifier resin, a petroleum-based tackifier resin, a terpene-based tackifier resin, a phenol-based tackifier resin, and a ketone-based tackifier resin. These can be used alone or in combination of two or more. Among them, one or more selected from a rosin-based tackifier resin, a rosin derivative tackifier resin, and a terpene phenol resin can be preferably used.
  • a tackifier resin having a softening point of 80 ° C. or higher (for example, 120 ° C. or higher and 180 ° C. or lower) (preferably a rosin derivative tackifier resin) can be preferably used.
  • the amount of the tackifier resin used is preferably 1 part by weight or more with respect to 100 parts by weight of the monomer component constituting the polymer contained in the pressure-sensitive adhesive from the viewpoint of appropriately exerting the effect of use. It may be 10 parts by weight or more, 15 parts by weight or more, 20 parts by weight or more, or 25 parts by weight or more. Further, from the viewpoint of achieving both adhesion to the adherend and cohesiveness in a well-balanced manner, the amount of the tackifier resin used for 100 parts by weight of the monomer component may be, for example, 50 parts by weight or less, or 30 parts by weight or less. Alternatively, the content of the tackifier resin in the pressure-sensitive adhesive may be, for example, less than 1 part by weight with respect to 100 parts by weight of the monomer component, and the pressure-sensitive adhesive does not substantially contain the tackifier resin. You may.
  • the pressure-sensitive adhesive disclosed herein may contain an acrylic oligomer from the viewpoint of improving cohesive force and adhesiveness.
  • an acrylic oligomer it is preferable to use a polymer having a Tg higher than that of the acrylic polymer Tg.
  • the acrylic oligomer is suitable in that it does not easily inhibit polymerization.
  • the acrylic oligomer include dicyclopentanyl methacrylate (DCPMA), cyclohexyl methacrylate (CHMA), isobornyl methacrylate (IBXMA), isobornyl acrylate (IBXA), and dicyclopentanyl acrylate (DCPA). , 1-adamantyl methacrylate (ADAM), 1-adamantyl acrylate (ADA) homopolymers, DCPMA and methyl methacrylate (MMA) copolymers, DCPMA and IBXMA copolymers, ADA and MMA co-polymers.
  • DCPMA dicyclopentanyl methacrylate
  • CHMA cyclohexyl methacrylate
  • IBXMA isobornyl methacrylate
  • IBXA isobornyl acrylate
  • DCPA dicyclopentanyl acrylate
  • ADAM 1-adamantyl methacrylate
  • ADA 1-adamantyl acryl
  • Polymer polymer of CHMA and isobutyl methacrylate (IBMA), polymer of CHMA and IBXMA, polymer of CHMA and acryloylmorpholin (ACMO), polymer of CHMA and diethylacrylamide (DEAA) , A polymer of CHMA and AA, and the like.
  • the acrylic oligomer may be used alone or in combination of two or more.
  • the Mw of the acrylic oligomer is typically about 1000 or more and less than about 30,000, preferably about 1500 or more and less than about 10,000, and more preferably about 2000 or more and less than about 5000. When Mw is within the above range, the effect of improving the cohesiveness and the adhesiveness with the adjacent surface is likely to be suitably exhibited.
  • the Mw of the acrylic oligomer can be measured by gel permeation chromatography (GPC) and determined as a standard polystyrene-equivalent value. Specifically, the measurement is carried out using TSKgelGMH-H (20) ⁇ 2 as a column on HPLC8020 manufactured by Tosoh Co., Ltd. under the condition of a flow rate of about 0.5 mL / min in a tetrahydrofuran solvent.
  • the content thereof can be, for example, 0.01 part by weight or more with respect to 100 parts by weight of the base polymer (typically, an acrylic polymer). From the viewpoint of obtaining a high effect, it may be 0.05 parts by weight or more, or 0.1 parts by weight or more. Further, from the viewpoint of compatibility with the base polymer and the like, the content of the acrylic oligomer is preferably less than 30 parts by weight, for example, 10 parts by weight or less, or 1 part by weight or less.
  • the pressure-sensitive adhesive disclosed herein may include a silane coupling agent.
  • the silane coupling agent it is preferable that the silane coupling agent is contained in the pressure-sensitive adhesive composition (and thus the pressure-sensitive adhesive) in a free form.
  • the adhesive force of the adhesive to the adherend tends to increase, but in order to improve the adhesive force, the adhesive is peeled off from the adherend at the time of peeling. The sex tends to decrease.
  • silane coupling agent examples include silicon compounds having an epoxy structure such as 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, and 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane; Amino group-containing silicon compounds such as 3-aminopropyltrimethoxysilane, N- (2-aminoethyl) 3-aminopropyltrimethoxysilane, N- (2-aminoethyl) 3-aminopropylmethyldimethoxysilane; 3-chloro (Meth) acrylic group-containing silane coupling agents such as propyltrimethoxysilane; acetacetyl group-containing trimethoxysilane; 3-acryloxypropyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane; 3-isocyanoxide propyltriethoxysilane Examples thereof
  • the amount of the silane coupling agent used can be set so as to obtain the desired effect of use, and is not particularly limited.
  • the amount of the silane coupling agent used may be, for example, 0.001 part by weight or more with respect to 100 parts by weight of the monomer component constituting the polymer contained in the pressure-sensitive adhesive, which has a higher effect. From the viewpoint of obtaining, it may be 0.005 parts by weight or more, 0.01 parts by weight or more, or 0.015 parts by weight or more. Further, in some embodiments, the amount of the silane coupling agent used may be, for example, 3 parts by weight or less, or 1 part by weight or less, based on 100 parts by weight of the monomer component constituting the pressure-sensitive adhesive.
  • the technique disclosed herein can be carried out in an embodiment using a pressure-sensitive adhesive which is substantially free of a silane coupling agent. By limiting the amount of the silane coupling agent used or by not using the silane coupling agent, the releasability from the adherend tends to be improved.
  • the pressure-sensitive adhesives disclosed herein are, if necessary, viscosity regulators (eg, thickeners), pH regulators, leveling agents, plasticizers, fillers, colorants such as pigments and dyes, stabilizers, preservatives.
  • viscosity regulators eg, thickeners
  • leveling agents e.g., leveling agents
  • plasticizers e.g., leveling agents
  • fillers e.g., g., g., g., g., g., g, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorbitol, sorb
  • the amount of components other than the base polymer (preferably acrylic polymer) in the pressure-sensitive adhesive may be limited.
  • the amount of the component other than the base polymer in the pressure-sensitive adhesive is, for example, about 30% by weight or less, preferably about 15% by weight or less, and preferably about 12% by weight or less ( For example, about 10% by weight or less).
  • a pressure-sensitive adhesive having such a composition easily satisfies a predetermined optical property (for example, transparency) and can be preferably used for optical applications.
  • the amount of the non-base polymer component in the pressure-sensitive adhesive may be approximately 5% by weight or less, may be approximately 3% by weight or less, and may be approximately 1.5% by weight or less (eg, approximately 1.5% by weight). 1% by weight or less) may be used.
  • Such a composition in which the amount of components other than the base polymer (for example, an acrylic polymer) is limited can be preferably adopted for the photocurable pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive layer can be a cured layer of the pressure-sensitive adhesive composition. That is, the pressure-sensitive adhesive layer can be formed by applying (for example, applying) the pressure-sensitive adhesive composition to an appropriate surface and then appropriately applying a curing treatment. When performing two or more types of curing treatments (drying, crosslinking, polymerization, etc.), these can be performed simultaneously or in multiple steps. In a pressure-sensitive adhesive composition using a partial polymer (acrylic polymer syrup) of a monomer component, a final copolymerization reaction is typically performed as the above-mentioned curing treatment.
  • a partial polymer acrylic polymer syrup
  • the partial polymer is subjected to a further copolymerization reaction to form a complete polymer.
  • a further copolymerization reaction for example, in the case of a photocurable pressure-sensitive adhesive composition, light irradiation is performed. If necessary, hardening treatment such as crosslinking and drying may be carried out.
  • a photocurable pressure-sensitive adhesive composition for example, in the case of a photo-curable pressure-sensitive adhesive composition in which a partial polymer of a monomer component is dissolved in an organic solvent
  • the composition is dried. It is advisable to perform photo-curing after this.
  • the pressure-sensitive adhesive layer having a multi-layer structure of two or more layers can be produced by laminating the pressure-sensitive adhesive layers formed in advance.
  • the pressure-sensitive adhesive composition may be applied on the first pressure-sensitive adhesive layer formed in advance, and the pressure-sensitive adhesive composition may be cured to form the second pressure-sensitive adhesive layer.
  • the pressure-sensitive adhesive composition can be applied using a conventional coater such as a gravure roll coater, a reverse roll coater, a kiss roll coater, a dip roll coater, a bar coater, a knife coater, or a spray coater.
  • a conventional coater such as a gravure roll coater, a reverse roll coater, a kiss roll coater, a dip roll coater, a bar coater, a knife coater, or a spray coater.
  • the thickness of the pressure-sensitive adhesive layer is not particularly limited and may be, for example, about 3 ⁇ m to 2000 ⁇ m. From the viewpoint of adhesion to the adherend such as step followability, in some embodiments, the thickness of the pressure-sensitive adhesive layer is preferably, for example, 10 ⁇ m or more, preferably 50 ⁇ m or more, 70 ⁇ m or more, and 100 ⁇ m. It may be more than 150 ⁇ m or more.
  • a thick adhesive has a high adhesive strength, and the adhesive strength with time tends to increase, so that it tends to be difficult to peel off.
  • the thickness of the pressure-sensitive adhesive layer may be, for example, 1000 ⁇ m or less, 500 ⁇ m or less, or 300 ⁇ m or less in some embodiments. Further, it may be 200 ⁇ m or less.
  • the pressure-sensitive adhesive is preferably an optical pressure-sensitive adhesive.
  • the optical pressure-sensitive adhesive may be one that does not impair the optical properties.
  • the haze value of the pressure-sensitive adhesive (layer) and, by extension, the pressure-sensitive adhesive sheet is not particularly limited, but in some embodiments, it is appropriate that the haze value is about 10% or less, and is about 5% or less (for example, about 3% or less). Can be.
  • the haze value is preferably 1.0% or less.
  • Such a highly transparent pressure-sensitive adhesive is suitable for optical applications that require high light transmission.
  • the haze value may be less than 1.0%, less than 0.7%, or 0.5% or less (for example, 0 to 0.5%).
  • the haze value can be adjusted by selecting, for example, the composition and thickness of the pressure-sensitive adhesive.
  • the "haze value” refers to the ratio of diffuse transmitted light to total transmitted light when the measurement target is irradiated with visible light. Also called cloudy price.
  • the haze value is determined by attaching the adhesive surface of the pressure-sensitive adhesive layer or the pressure-sensitive adhesive sheet to one side of an alkaline glass having a haze value of 0.1% to form a laminate of the pressure-sensitive adhesive layer or the pressure-sensitive adhesive sheet and the alkaline glass, and then a haze meter (for example, Murakami). It can be measured using the product name "MR-100") manufactured by Color Technology Research Institute.
  • MR-100 haze meter manufactured by Color Technology Research Institute.
  • the alkaline glass to which the pressure-sensitive adhesive layer or the pressure-sensitive adhesive sheet is attached is arranged so that the pressure-sensitive adhesive layer or the pressure-sensitive adhesive sheet is on the light source side. Since the haze value of the alkaline glass is 0.1%, the value obtained by subtracting 0.1% from the measured value is defined as the haze value [%] of the pressure-sensitive adhesive layer or the pressure-sensitive adhesive sheet.
  • the pressure-sensitive adhesive sheet used to join the members in the bonded body comprises a substrate layer.
  • the base material layer is a support (support layer) that supports the pressure-sensitive adhesive layer.
  • the substrate layer can be an intermediate layer disposed between the first and second pressure-sensitive adhesive layers constituting the surface of the pressure-sensitive adhesive sheet.
  • Examples of the base material layer disclosed herein include various resin films such as polyolefin films, polyester films, and polyvinyl chloride films; foam sheets made of foams such as polyurethane foams, polyethylene foams, and polychloroprene foams; and various types.
  • Woven fabrics and non-woven fabrics made of fibrous substances naturally fibers such as linen and cotton, synthetic fibers such as polyester and vinylon, semi-synthetic fibers such as acetate, etc.
  • Japanese paper, fine paper, craft Papers such as paper and crepe paper
  • metal foils such as aluminum foil, copper foil, and stainless steel (SUS); and the like can be mentioned. It may be a layered body having a structure in which these are combined.
  • Examples of such a base material layer having a composite structure include a laminated base material (multilayer structure base material) having a structure in which a metal foil and the above resin film are laminated, a resin sheet reinforced with an inorganic fiber such as glass cloth, and the like. Can be mentioned.
  • a material containing a resin film that can independently maintain its shape as a base film
  • a resin film means a resin film (of voidless) having a non-porous structure and typically containing substantially no bubbles. Therefore, the resin film is a concept that is distinguished from foam films and non-woven fabrics.
  • the resin film may have a single-layer structure or a multi-layer structure having two or more layers (for example, a three-layer structure).
  • the resin film can be a transparent film. The transparent resin film is suitable for optical applications.
  • the resin material constituting the resin film include polyester resin, polyphenylene sulfide (PPS) resin, polyolefin resin, and polyimide resin.
  • Specific examples of the resin film that can be preferably used as the base material layer include polyethylene terephthalate (PET) film, polyethylene naphthalate (PEN) film, PPS film, polyetheretherketone (PEEK) film, transparent polyimide (CPI) film, and polypropylene.
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • PPS film polyetheretherketone
  • CPI transparent polyimide
  • PPI polypropylene.
  • Preferred examples from the viewpoint of strength include PET film, PEN film, PPS film, PEEK film, and CPI film.
  • Preferred examples include PET film, CPI film, and TAC film from the viewpoint of availability, dimensional stability, optical characteristics, and the like.
  • additives such as light stabilizers, antioxidants, antistatic agents, colorants (dye, pigment, etc.), fillers, slip agents, antiblocking agents, etc. shall be added to the resin film, if necessary. Can be done.
  • the blending amount of the additive is not particularly limited and can be appropriately set according to the intended use and the like.
  • the method for manufacturing the resin film is not particularly limited.
  • conventionally known general resin film molding methods such as extrusion molding, inflation molding, T-die casting molding, and calender roll molding can be appropriately adopted.
  • the base material layer may be substantially composed of such a resin film.
  • the base material layer may include an auxiliary layer in addition to the resin film.
  • the auxiliary layer include a surface treatment layer such as an undercoat layer and a release layer.
  • corona treatment, plasma treatment, ultraviolet irradiation treatment, acid treatment, alkali treatment, undercoating agent (primer) application, antistatic treatment, and peeling are performed, if necessary.
  • Conventionally known surface treatment such as treatment may be applied.
  • the thickness of the base material layer is not particularly limited, and may be, for example, about 1000 ⁇ m or less, may be about 500 ⁇ m or less, and from the viewpoint of weight reduction and thinning, about 100 ⁇ m or less is appropriate, and may be 70 ⁇ m or less. Further, from the viewpoint of handleability, processability and the like, the thickness of the base material layer may be, for example, 1 ⁇ m or more, preferably about 20 ⁇ m or more, and preferably about 30 ⁇ m or more.
  • the length and width of the pressure-sensitive adhesive sheet are not particularly limited. Since the entire surface of the pressure-sensitive adhesive sheet is usually adhered to the adherend of the pressure-sensitive adhesive sheet, when the adherend is solvent-impermeable, the solvent contacts the pressure-sensitive adhesive only from the end face of the pressure-sensitive adhesive sheet during solvent immersion. Therefore, the larger the size (length and width) of the pressure-sensitive adhesive sheet, the longer it tends to take for solvent immersion peeling.
  • the desired effect can also be achieved on relatively large adhesive sheets, such as adhesive sheets having at least one of a length and a width of 20 mm or more (and even 40 mm or more, for example 60 mm or more). It can be realized. Further, the width of the widest portion of the pressure-sensitive adhesive sheet (specifically, the adhesive region of the pressure-sensitive adhesive sheet) to be peeled off by the technique disclosed herein is, for example, 200 mm or less, and 100 mm or less, from the viewpoint of solvent immersion peeling efficiency. May be.
  • this monomer syrup 0.1 part of dipentaerythritol hexaacrylate as a polyfunctional monomer, and a nonionic surfactant as a water-affinitive agent (polyoxyethylene sorbitan monolaurate, HLB16.7, trade name " Leodor TW-L120 ", manufactured by Kao Co., Ltd.) 0.3 parts, and the trade name” KBE403 (manufactured by Shinetsu Silicone Co., Ltd.) 0.4 parts as a silane coupling agent are added and mixed uniformly to form an ultraviolet curable pressure-sensitive adhesive. The thing was prepared.
  • the pressure-sensitive adhesive composition obtained above is applied to a release film R1 (manufactured by Mitsubishi Resin Co., Ltd., product name "MRF # 38”) having a thickness of 38 ⁇ m in which one side of the polyester film is a release surface, and one side of the polyester film is applied.
  • a release film R2 manufactured by Mitsubishi Resin Co., Ltd., product name "MRE # 38" with a thickness of 38 ⁇ m is covered with a release surface to block air, and the film is cured by irradiating it with ultraviolet rays to obtain a thickness of 200 ⁇ m.
  • a pressure-sensitive adhesive layer was formed.
  • Ultraviolet rays are irradiated for 180 seconds using a black light lamp with an illuminance of 4 mW / cm 2 (measured by an industrial UV checker (manufactured by Topcon, trade name "UVR-T1") with a peak sensitivity wavelength of about 350 nm). I went there. In this way, an adhesive sheet A (an adhesive sheet composed of only an adhesive layer) was obtained. The surface of the adhesive sheet A to be attached to the adherend is protected by the release films R1 and R2.
  • the adhesive sheets A and B were evaluated for solvent immersion peelability by the following method. Peel off the peeling liner that covers one surface of the adhesive layer (supportless double-sided adhesive sheet) from the adhesive sheet, and make 11 ⁇ m thick aluminum foil on the exposed adhesive surface (manufactured by Toyo Aluminum Echo Products Co., Ltd., product name “Sunfoil”). was laminated and cut into a size of 80 mm ⁇ 200 mm.
  • the peeling liner covering the other surface of the adhesive layer was peeled off, and the exposed adhesive surface was made of an alkaline glass plate (manufactured by Matsunami Glass Industry Co., Ltd., manufactured by the float method, thickness 1.35 mm, blue plate edge polished product, adhesive.
  • the sheets were bonded to the entire surface (65 mm ⁇ 165 mm size) of the surface to which the sheets were bonded (contact angle with distilled water: 8 degrees).
  • This laminate of aluminum foil / adhesive / alkaline glass plate was crimped by reciprocating a 2 kg rubber roller twice. The aluminum foil and the adhesive that protruded from the alkaline glass plate were cut and removed to prepare a laminate of aluminum foil / adhesive / alkaline glass plate to be evaluated.
  • a plurality of the above laminates are prepared, each of which is immersed in each solvent shown in Table 1, and the adhesive sheet (65 mm width) is peeled off from the end (one end) in the width direction 5 hours and 24 hours after the start of immersion.
  • the distance [mm] was measured.
  • Solvent immersion was carried out under the condition of 23 ° C.
  • the results are shown in Table 1.
  • “peeling” in the table indicates that the entire adhesive sheet has peeled off from the adherend (specifically, a state in which the adhesive has floated and peeled off from the adherend due to swelling of the adhesive), and peeling from one end thereof. It can be said that the distance is 32.5 mm.
  • "-" in the table indicates that the measurement was not performed.
  • the contact angle of the alkaline glass plate is measured by the following method. That is, in a measurement atmosphere of 23 ° C. and 50% RH, a contact angle meter (manufactured by Kyowa Interface Science Co., Ltd., trade name “DMo-501 type”, control box “DMC-2", control / analysis software "FAMAS (version)” 5.0.30) ”) is used to measure by the sessile drop method. The amount of distilled water dropped is 2 ⁇ L, and the contact angle is calculated by the ⁇ / 2 method from the image 5 seconds after dropping (implemented at N5).
  • HSP value and HSP distance HSP values (dispersion term ( ⁇ D), polarity term ( ⁇ P), hydrogen bond term ( ⁇ H)) are calculated for the pressure-sensitive adhesive and each solvent of the pressure-sensitive adhesive sheet A, and the HSP distance between the pressure-sensitive adhesive and each solvent is calculated. I asked. The results are shown in Table 3.
  • the adhesive swelled due to solvent immersion, and spontaneous peeling proceeded.
  • the solvent immersion using ethyl acetate was able to peel off the pressure-sensitive adhesive in the shortest immersion time.
  • the pressure-sensitive adhesive sheet A containing the water-affinitive agent originally having water-removability lost the water-removability.
  • the solvent immersion peelability tends to improve as the hydrogen bond term ( ⁇ H) increases from the above experimental results and the HSP value. Admitted. Since the pressure-sensitive adhesive sheet A contains a water-affinitive agent, it is considered that the hydrogen bond term contributed to the improvement of the peelability. Alcohols such as methanol and ethanol having a ⁇ H of 15.0 or more showed good solvent immersion peelability.
  • the pressure-sensitive adhesive can be peeled off from the member by performing solvent immersion peeling on the bonded body containing the two members joined by the pressure-sensitive adhesive containing a water-affinitive agent, and the above-mentioned two members are separated. It turns out that it can be done.
  • One surface (first adhesive surface) 1B The other surface (second adhesive surface) 100 Joiner 120 First member 140 Second member 200 Solvent 250 Container

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
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KR20250043487A (ko) 2022-07-29 2025-03-28 닛토덴코 가부시키가이샤 점착 시트의 박리 방법
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WO2025121131A1 (ja) * 2023-12-04 2025-06-12 日東電工株式会社 解体方法および粘着シート

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