WO2022004609A1 - 粘着剤処理液、および粘着剤処理方法 - Google Patents

粘着剤処理液、および粘着剤処理方法 Download PDF

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Publication number
WO2022004609A1
WO2022004609A1 PCT/JP2021/024220 JP2021024220W WO2022004609A1 WO 2022004609 A1 WO2022004609 A1 WO 2022004609A1 JP 2021024220 W JP2021024220 W JP 2021024220W WO 2022004609 A1 WO2022004609 A1 WO 2022004609A1
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Prior art keywords
pressure
sensitive adhesive
weight
treatment liquid
examples
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/JP2021/024220
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English (en)
French (fr)
Japanese (ja)
Inventor
晃好 山本
隆之 野村
剛史 西部
洋佑 山田
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Nitto Denko Corp
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Nitto Denko Corp
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Application filed by Nitto Denko Corp filed Critical Nitto Denko Corp
Priority to CN202180045876.6A priority Critical patent/CN115996976A/zh
Priority to US18/013,148 priority patent/US12612502B2/en
Priority to JP2022533965A priority patent/JP7232381B2/ja
Priority to EP21832393.9A priority patent/EP4174123A4/en
Publication of WO2022004609A1 publication Critical patent/WO2022004609A1/ja
Anticipated expiration legal-status Critical
Priority to JP2023023175A priority patent/JP7296531B2/ja
Priority to US19/577,680 priority patent/US20260217938A1/en
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/06—Recovery or working-up of waste materials of polymers without chemical reactions
    • C08J11/08—Recovery or working-up of waste materials of polymers without chemical reactions using selective solvents for polymer components
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/385—Acrylic polymers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/02—Inorganic compounds
    • C11D7/04—Water-soluble compounds
    • C11D7/06—Hydroxides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5004—Organic solvents
    • C11D7/5022—Organic solvents containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/50—Additional features of adhesives in the form of films or foils characterized by process specific features
    • C09J2301/502—Additional features of adhesives in the form of films or foils characterized by process specific features process for debonding adherents
    • 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
    • C09J2433/00—Presence of (meth)acrylic polymer
    • 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 an adhesive treatment liquid.
  • the present invention also relates to a pressure-sensitive adhesive treatment method.
  • Adhesive tape is used in large quantities for attaching labels to articles and packaging materials, packing packaging materials, using it in the manufacturing process of electronic members and optical members, and masking applications. Particularly in recent years, the use of electronic members and optical members in the manufacturing process has been increasing, and a large amount of adhesive tape waste is generated at manufacturing sites and the like.
  • Adhesive tape waste is usually burned and disposed of, or brought to a waste disposal site for disposal.
  • disposal treatment is not preferable from the viewpoint of reducing the environmental load.
  • the material of such an adhesive tape include an adhesive and a base material.
  • the composition of the pressure-sensitive adhesive constituting the pressure-sensitive adhesive layer is an alkoxyalkyl (meth) acrylate (7 to 30% by weight), a caprolactone adduct of (meth) acrylic acid (1 to 15% by weight), and the number of carbon atoms.
  • an alkaline aqueous solution is provided by including a potential swelling component (a random, block or graft copolymer containing 35-90% by weight of lower alkyl esters of acrylic acid and / or maleic acid) in the adhesive.
  • a potential swelling component a random, block or graft copolymer containing 35-90% by weight of lower alkyl esters of acrylic acid and / or maleic acid
  • the adhesive is desorbed by performing a saponification treatment with a substance to which methanol or ethanol is added.
  • Patent Document 3 A technique for self-peeling the adhesive by immersing the heat-sensitive adhesive label, which is suitably peeled off during PET bottle recycling, in an aqueous thermal solvent at 60 ° C. or higher has been reported (Patent Document 3).
  • a heat-sensitive pressure-sensitive adhesive composition containing an acrylic acid ester copolymer as a polymer material as a pressure-sensitive adhesive, a heat-expanding agent, polyvinyl alcohol having a saponification degree of 95 mol% or more, and a cross-linking agent or curing agent.
  • the adhesive is self-peeled by containing the agent.
  • the adhesive contained in the adhesive tape remains on the adherend when the adhesive tape is peeled off from the adherend to which the adhesive tape is attached. It is required that it can be peeled off from the adherend without any trouble.
  • the adhesive contained in the adhesive tape is contained when the adhesive tape is peeled off from the adherend to which the adhesive tape is attached due to various factors such as the type of the adherend, the type of the adhesive tape, and the usage environment. May leave adhesive residue on the adherend. In such a case, it is necessary to easily remove the adhesive remaining on the adhesive without damaging the adherend. For example, in the process of assembling an electronic component, when the above-mentioned adhesive residue is generated, it is necessary to easily remove the adhesive residue without damaging the adherend.
  • the pressure-sensitive adhesive may adhere to the manufacturing equipment such as the polymerization pot, the coating machine, and the coating roll.
  • a great deal of labor is required to remove the adhesive adhering to the manufacturing equipment such as the polymerization pot, the coating machine, and the coating roll, and to perform cleaning.
  • Japanese Unexamined Patent Publication No. 11-241053 Japanese Unexamined Patent Publication No. 11-323280 Japanese Unexamined Patent Publication No. 7-113067
  • An object of the present invention is to provide a pressure-sensitive adhesive treatment liquid that can easily remove various types of pressure-sensitive adhesives, and a pressure-sensitive adhesive treatment method that can easily remove various types of pressure-sensitive adhesives.
  • a pressure-sensitive adhesive treatment liquid capable of easily separating the base material and various types of pressure-sensitive adhesive when the base material and the pressure-sensitive adhesive tape containing the pressure-sensitive adhesive are treated, and the base material. It corresponds to providing a pressure-sensitive adhesive treatment method for easily separating various kinds of pressure-sensitive adhesives.
  • a pressure-sensitive adhesive treatment liquid capable of easily separating various types of pressure-sensitive adhesives from the adherend when the pressure-sensitive adhesive remaining on the adherend is treated. It corresponds to providing a pressure-sensitive adhesive treatment method which easily separates various kinds of pressure-sensitive adhesives from an adherend.
  • the above-mentioned problem is, for example, when the pressure-sensitive adhesive adhered to a manufacturing apparatus such as a polymerization kettle, a coating machine, or a coating roll is targeted for processing in a polymerization process or a coating process when producing a pressure-sensitive adhesive.
  • Adhesive treatment liquid that can easily separate the adhesive from the manufacturing equipment such as the polymerization kettle, the coating machine and the coating roll, and the adhesive from the manufacturing equipment such as the polymerization kettle, the coating machine and the coating roll. It corresponds to providing a pressure-sensitive adhesive treatment method which can be easily separated.
  • the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention is It is a treatment liquid for adhesives. Contains liquids and alkaline compounds with a Hansen solubility parameter value of 31 or less. The concentration of the alkaline compound is 0.001% by weight to 20% by weight.
  • the Hansen solubility parameter value is 28 or less.
  • the Hansen solubility parameter value is 25 or less.
  • the concentration of the alkaline compound is 0.01% by weight to 10% by weight.
  • the concentration of the alkaline compound is 0.1% by weight to 1% by weight.
  • the above-mentioned pressure-sensitive adhesive is composed of at least one selected from the group consisting of an acrylic-based pressure-sensitive adhesive, a urethane-based pressure-sensitive adhesive, a rubber-based pressure-sensitive adhesive, and a silicone-based pressure-sensitive adhesive.
  • the pressure-sensitive adhesive treatment method according to the embodiment of the present invention A method for treating a pressure-sensitive adhesive using the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention.
  • the pressure-sensitive adhesive is impregnated with the pressure-sensitive adhesive treatment liquid.
  • stirring is performed with the pressure-sensitive adhesive impregnated with the pressure-sensitive adhesive treatment liquid.
  • ultrasonic treatment is performed with the pressure-sensitive adhesive impregnated with the pressure-sensitive adhesive treatment liquid.
  • a pressure-sensitive adhesive treatment liquid capable of easily separating the base material and various types of pressure-sensitive adhesive, and a base material. It corresponds to being able to provide a pressure-sensitive adhesive treatment method for easily separating various types of pressure-sensitive adhesives.
  • the above-mentioned effect is, for example, a pressure-sensitive adhesive treatment liquid capable of easily separating various types of pressure-sensitive adhesives from the adherend when the pressure-sensitive adhesive remaining on the adherend is treated. It corresponds to being able to provide a pressure-sensitive adhesive treatment method for easily separating various kinds of pressure-sensitive adhesives from an adherend.
  • the above effect can be obtained, for example, when a pressure-sensitive adhesive adhering to a manufacturing apparatus such as a polymerization pot, a coating machine, or a coating roll is treated as a treatment target in a polymerization process or a coating process when producing a pressure-sensitive adhesive.
  • Adhesive treatment liquid that can easily separate the adhesive from the manufacturing equipment such as the polymerization kettle, the coating machine and the coating roll, and the adhesive from the manufacturing equipment such as the polymerization kettle, the coating machine and the coating roll. It corresponds to providing a pressure-sensitive adhesive treatment method which can be easily separated.
  • weight When the expression “weight” is used in this specification, it may be read as “mass” which is commonly used as an SI system unit indicating weight.
  • the expression “(meth) acrylic” means “acrylic and / or methacrolein”
  • the expression “(meth) acrylate” means “acrylate and / or methacrylate”.
  • the expression “(meth) allyl” is used, it means “allyl and / or methacrolein”
  • the expression “(meth) acrolein” is used, “acrolein and / or methacrolein” is used. It means “rain”.
  • the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention is a pressure-sensitive adhesive treatment liquid.
  • the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention can easily remove various types of pressure-sensitive adhesives.
  • the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention corresponds to, for example, the treatment liquid for the pressure-sensitive adhesive tape containing the base material and the pressure-sensitive adhesive when the pressure-sensitive adhesive tape containing the base material and the pressure-sensitive adhesive is treated.
  • the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention can easily separate the base material and various types of pressure-sensitive adhesives.
  • the adhesive tape as an example of the processing target will be described in detail later.
  • the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention can easily separate various types of pressure-sensitive adhesives from the adherend, for example, when the pressure-sensitive adhesive remaining on the adherend is treated.
  • any suitable adherend may be adopted as long as the effect of the present invention is not impaired.
  • a small amount of adhesive residue such as a silicon wafer, a semiconductor circuit board, an electronic device such as a ceramic capacitor, an optical film, and an optical material such as optical glass may cause a deterioration in the function of the adherend. Some are considered for sex.
  • the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention is, for example, a pressure-sensitive adhesive adhering to a manufacturing apparatus such as a polymerization pot, a coating machine, or a coating roll in a polymerization step or a coating process when manufacturing a pressure-sensitive adhesive.
  • a manufacturing apparatus such as a polymerization pot, a coating machine, or a coating roll
  • a pressure-sensitive adhesive treatment liquid capable of easily separating the pressure-sensitive adhesive from a manufacturing apparatus such as a polymerization pot, a coating machine, or a coating roll.
  • the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention contains a liquid having a Hansen solubility parameter value of 31 or less and an alkaline compound, and the concentration of the alkaline compound is 0.001% by weight to 20% by weight.
  • the "liquid” referred to in the present invention is a liquid at normal temperature and pressure, and generally includes water, alcohol, and various other solvents.
  • the Hansen solubility parameter value in the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention may be only one type or two or more types.
  • the alkaline compound in the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention may be only one kind or two or more kinds.
  • the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention contains a liquid having a Hansen solubility parameter value of 31 or less and an alkaline compound, and the concentration of the alkaline compound is 0.001% by weight to 20% by weight.
  • the adhesive can be easily removed.
  • the "Hansen solubility parameter value" in the present invention divides the Hildebrand solubility parameter value into three components, a dispersion term ( ⁇ D ), a polarity term ( ⁇ p ), and a hydrogen bond term ( ⁇ H). , It is a parameter value considering the polarity of the substance, and may be abbreviated as the HSP value.
  • the dispersion term (van der Waals force term), polarity term (dipole moment term), and hydrogen bond term (hydrogen bond term) can be expressed in three-dimensional coordinates.
  • the Hansen solubility parameter value of a mixture of two or more liquids can be obtained as a weighted average value m of the HSP value of each solvent by the following formula (1).
  • m ⁇ 1 ⁇ 1 + ⁇ 2 ⁇ 2 ...
  • ⁇ 1 and ⁇ 2 are HSP values of each liquid component
  • ⁇ 1 and ⁇ 2 are volume fractions of each liquid component.
  • the Hansen solubility parameter value of each solvent is recorded in "HSPiP version 5", and for the solvent not recorded, the value estimated by "HSPiP version 5" is used.
  • the Hansen solubility parameter value of the liquid contained in the pressure-sensitive adhesive treatment liquid is 31 or less, preferably 28 or less, and more preferably 25 or less.
  • the lower limit of the Hansen solubility parameter value of the liquid contained in the pressure-sensitive adhesive treatment liquid is preferably 7 or more, more preferably 10 or more, still more preferably 13 or more. Is.
  • the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention if the Hansen solubility parameter value of the liquid contained in the pressure-sensitive adhesive treatment liquid is within the above range, the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention can be of various types. The adhesive can be removed more easily.
  • the permeability of the pressure-sensitive adhesive treatment liquid to the pressure-sensitive adhesive may deteriorate. , It may be difficult to remove the adhesive.
  • the Hansen solubility parameter value of the liquid contained in the pressure-sensitive adhesive treatment liquid is less than 7, it is not so much as the case where it exceeds 31, but similarly to the pressure-sensitive adhesive. The permeability of the pressure-sensitive adhesive treatment liquid may deteriorate, and it may be difficult to remove the pressure-sensitive adhesive.
  • Typical examples of the liquid having a Hansen solubility parameter value of 31 or less as a single liquid contained in the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention include the following liquids.
  • 2-propanol IPA
  • HSP value 23.6
  • Dipropylene glycol 26.4
  • any mixed liquid having m of 31 or less according to the above formula (1) can be used as the Hansen solubility parameter value as a mixed liquid in which a plurality of liquids are combined. ..
  • any suitable alkaline compound can be adopted as long as the effect of the present invention is not impaired.
  • alkaline compounds include hydroxides and carbonates of alkali metals or alkaline earth metals such as potassium hydroxide, sodium hydroxide and calcium hydroxide, and sodium methoxydo, sodium ethoxyoxide and potassium.
  • Metal alkoxides such as t-butoxide are mentioned, preferably at least one selected from the group consisting of potassium hydroxide and sodium hydroxide.
  • the concentration of the alkaline compound in the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention is 0.001% by weight to 20% by weight, preferably 0.01% by weight to 10% by weight, and more preferably 0.01% by weight. It is from% by weight to 5% by weight, more preferably 0.1% by weight to 1% by weight.
  • concentration of the alkaline compound in the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention is within the above range, the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention can more easily remove various types of pressure-sensitive adhesives. can.
  • the concentration of the alkaline compound in the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention exceeds 20% by weight, the alkaline compound becomes difficult to dissolve in the treatment solvent, and when it is in the form of a pressure-sensitive adhesive tape, not only the pressure-sensitive adhesive but also the base. There is a risk of adversely affecting the material.
  • the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention may contain other additives.
  • any suitable additive may be adopted as long as the effect of the present invention is not impaired.
  • various known additives such as an ionic surfactant, a nonionic surfactant, a chelating agent, a solubilizing agent, a slurrying agent, and an antifoaming agent can be added.
  • the pressure-sensitive adhesive treatment method according to the embodiment of the present invention is a method for treating a pressure-sensitive adhesive using the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention, and impregnates the pressure-sensitive adhesive with the pressure-sensitive adhesive treatment liquid. According to such a pressure-sensitive adhesive treatment method, various types of pressure-sensitive adhesives can be easily removed.
  • impregnating the pressure-sensitive adhesive with the pressure-sensitive adhesive treatment liquid means to impregnate the pressure-sensitive adhesive with the pressure-sensitive adhesive treatment liquid, and for example, at least a part of the pressure-sensitive adhesive is used. Immersion in the pressure-sensitive adhesive treatment liquid may be mentioned. This is because if at least a part of the pressure-sensitive adhesive is immersed in the pressure-sensitive adhesive treatment liquid, the pressure-sensitive adhesive treatment liquid will soak into the pressure-sensitive adhesive.
  • one preferred embodiment is stirring with the pressure-sensitive adhesive impregnated with the pressure-sensitive adhesive treatment liquid.
  • stirring the pressure-sensitive adhesive with the pressure-sensitive adhesive treatment liquid impregnated various types of pressure-sensitive adhesive can be removed more easily.
  • the "state in which the pressure-sensitive adhesive is impregnated with the pressure-sensitive adhesive treatment liquid" is a state in which the pressure-sensitive adhesive is impregnated with the pressure-sensitive adhesive treatment liquid.
  • the state of being immersed in the agent treatment liquid can be mentioned. This is because if at least a part of the pressure-sensitive adhesive is immersed in the pressure-sensitive adhesive treatment liquid, the pressure-sensitive adhesive treatment liquid will soak into the pressure-sensitive adhesive.
  • any appropriate stirring method can be appropriately adopted depending on the scale and the type of the adhesive.
  • one preferred embodiment is to perform ultrasonic treatment with the pressure-sensitive adhesive impregnated with the pressure-sensitive adhesive treatment liquid.
  • ultrasonic treatment By performing ultrasonic treatment with the pressure-sensitive adhesive impregnated with the pressure-sensitive adhesive treatment liquid, various types of pressure-sensitive adhesive can be removed more easily.
  • any appropriate ultrasonic treatment method can be appropriately adopted depending on the scale and the type of the adhesive.
  • the temperature of the pressure-sensitive adhesive impregnated with the pressure-sensitive adhesive treatment liquid is preferably 20 ° C. or higher, more preferably 25 ° C. or higher. It is more preferably 30 ° C. or higher, further preferably 35 ° C. or higher, further preferably 40 ° C. or higher, still more preferably 45 ° C. or higher, still more preferably 50 ° C. or higher, still more preferably 50 ° C. or higher. It is 55 ° C. or higher, particularly preferably 60 ° C. or higher, and most preferably 65 ° C. or higher.
  • various types of pressure-sensitive adhesive can be removed more easily.
  • another preferred embodiment is to impregnate the pressure-sensitive adhesive with the pressure-sensitive adhesive treatment liquid when the pressure-sensitive adhesive tape containing the base material and the pressure-sensitive adhesive is treated.
  • the temperature of the state is 20 ° C. or higher, which is lower than the temperature at which the melting point of the base material and the decomposition temperature of the pressure-sensitive adhesive are lower.
  • the temperature of the pressure-sensitive adhesive impregnated in the pressure-sensitive adhesive treatment liquid is preferably 25 ° C. or higher, which is lower than the melting point of the base material and the temperature at which the decomposition temperature of the pressure-sensitive adhesive is lower, more preferably 25 ° C. or higher.
  • the temperature is lower than the melting point of the base material and the decomposition temperature of the pressure-sensitive adhesive, more preferably 30 ° C. or higher, and lower than the melting point of the base material and the decomposition temperature of the pressure-sensitive adhesive. It is preferably 35 ° C. or higher, which is lower than the melting point of the base material and the decomposition temperature of the pressure-sensitive adhesive, and more preferably 40 ° C. or higher, whichever has the lower melting point of the base material and the decomposition temperature of the pressure-sensitive adhesive. It is below the temperature, more preferably 45 ° C. or higher, at least the temperature at which the melting point of the substrate and the decomposition temperature of the pressure-sensitive adhesive are lower, still more preferably 50 ° C.
  • the temperature is lower than the lower decomposition temperature, more preferably 55 ° C. or higher, the melting point of the base material and the temperature lower than the decomposition temperature of the pressure-sensitive adhesive, particularly preferably 60 ° C. or higher, of the base material.
  • the temperature is lower than the melting point and the temperature at which the decomposition temperature of the pressure-sensitive adhesive is lower, most preferably 65 ° C. or higher, and lower than the temperature at which the melting point of the substrate and the decomposition temperature of the pressure-sensitive adhesive are lower.
  • the pressure-sensitive adhesive is swollen by the pressure-sensitive adhesive treatment liquid and is hydrolyzed (ester) by a liquid and an alkaline compound having a Hansen solubility parameter value of 31 or less contained in the pressure-sensitive adhesive treatment liquid. It is presumed that (including the hydrolysis reaction in which salts and alcohols are produced by the reaction between the base and the base) proceeds.
  • the adhesive is separated from the base material.
  • the base material can be recovered as it is in a recyclable state, and (2) the adhesive can be easily peeled off from the base material, or according to the embodiment of the present invention. It can be recovered as a solution or dispersion by dissolving or dispersing in a pressure-sensitive adhesive treatment solution and, if necessary, further treating with an organic solvent, and preferably as a polymer solution or dispersion. It can be recovered.
  • the polymer is a water-insoluble polymer, it can be recovered as a solution dissolved in an organic solvent, and when the polymer is a water-soluble polymer, it can be recovered as a solution dissolved in an aqueous solvent.
  • the aqueous solvent include water, alcohol, a mixed solvent thereof, and a mixed solvent of these and an organic solvent.
  • a solution or dispersion of a water-soluble polymer derived from the pressure-sensitive adhesive is preferably obtained.
  • the "water-soluble polymer derived from the pressure-sensitive adhesive” means a water-soluble polymer having a structure derived from the main polymer (also referred to as a base polymer) used in the composition of the pressure-sensitive adhesive, and specifically.
  • the pressure-sensitive adhesive treatment liquid For example, at least a part of functional groups (for example, carboxyl group or ester group) present at the side chain end of the main polymer (sometimes referred to as a base polymer) constituting the pressure-sensitive adhesive is contained in the pressure-sensitive adhesive treatment liquid. It means a water-soluble polymer having a structure that has been hydrolyzed (including a saponification reaction in which a salt and an alcohol are produced by a reaction between an ester and a base) by a liquid and an alkaline compound having a Hansen solubility parameter value of 31 or less.
  • a carboxyl group-containing monomer is preferably added in an amount of 5 by weight in all the monomers used to obtain the main polymer (sometimes referred to as a base polymer) constituting the pressure-sensitive adhesive.
  • %-95% by weight more preferably 10% by weight to 95% by weight, still more preferably 15% by weight to 95% by weight, still more preferably 20% by weight to 95% by weight, still more preferably 25% by weight to 25% by weight. It contains 95% by weight, more preferably 30% by weight to 95% by weight, particularly preferably 35% by weight to 90% by weight, and most preferably 40% by weight to 90% by weight.
  • carboxyl group-containing monomer examples include (meth) acrylic acid, itaconic acid, maleic acid, fumaric acid, crotonic acid, isocrotonic acid, and acid anhydrides thereof (for example, maleic anhydride, itaconic anhydride and the like).
  • (Material-containing monomer) preferably (meth) acrylic acid, more preferably acrylic acid, an acrylate having an alkaline cation as a counter cation.
  • the liquid contained in the pressure-sensitive adhesive treatment liquid having a Hansen solubility parameter value of 31 or less is preferably a lower alcohol and an organic solvent other than the lower alcohol and the lower alcohol. At least one selected from the mixed solvent with.
  • the lower alcohol may be only one kind or two or more kinds.
  • the organic solvent may be only one kind or two or more kinds.
  • the content ratio of the lower alcohol in the mixed solvent of the lower alcohol and the organic solvent other than the lower alcohol is preferably 1% by weight to 90% by weight. , More preferably 5% by weight to 80% by weight, still more preferably 10% by weight to 70% by weight, and particularly preferably 10% by weight to 60% by weight.
  • the lower alcohol preferably contains a lower alcohol having 1 to 5 carbon atoms (at least one selected from methanol, ethanol, butanol, 1-propanol, 2-propanol, and 1-pentanol), and more preferably.
  • a lower alcohol having 1 to 4 carbon atoms at least one selected from methanol, ethanol, butanol, 1-propanol, and 2-propanol
  • a lower alcohol having 1 to 3 carbon atoms methanol, It contains at least one selected from ethanol and butanol
  • the lower alcohols include not only primary alcohols but also secondary alcohols such as isopropyl alcohol, propylene glycol monopropyl ether and propylene glycol monoethyl ether, and tertiary alcohols such as t-butyl alcohol. Can be included.
  • organic solvent other than the above lower alcohol examples include hydrocarbons such as benzene, toluene, styrene, hexane, cyclohexane and methylcyclohexane; ketones such as acetone; esters such as ethyl acetate; tetrahydrofuran, cyclopentylmethyl ether and the like.
  • the liquid contained in the pressure-sensitive adhesive treatment liquid having a Hansen solubility parameter value of 31 or less may contain a metal alkoxide as an alkaline compound.
  • a metal alkoxide may be only one kind or two or more kinds.
  • any suitable metal alkoxide can be adopted as long as the effect of the present invention is not impaired.
  • metal alkoxides include sodium methoxide, sodium ethoxide, and potassium t-butoxide.
  • a water-soluble polymer can be easily obtained from the pressure-sensitive adhesive under mild conditions.
  • hydrolysis of the pressure-sensitive adhesive including a saponification reaction in which a salt and an alcohol are produced by a reaction between an ester and a base
  • a water-soluble polymer is obtained.
  • the pressure-sensitive adhesive in order to hydrolyze a pressure-sensitive adhesive (including a saponification reaction in which a salt and an alcohol are generated by a reaction between an ester and a base), the pressure-sensitive adhesive is subjected to the above reaction under high temperature and high pressure conditions, or the pressure-sensitive adhesive is used. It is necessary to design the composition of the above to a limited composition.
  • the pressure-sensitive adhesive treatment method according to the embodiment of the present invention the pressure-sensitive adhesive can be easily prepared under mild conditions without conditions under high temperature and high pressure and without designing the composition of the pressure-sensitive adhesive to a limited composition. Good hydrolysis of the pressure-sensitive adhesive (including a saponification reaction in which a salt and an alcohol are produced by a reaction between an ester and a base) can be carried out.
  • the adhesive tape as an example of the treatment target using the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention contains a base material and a pressure-sensitive adhesive, and more specifically, includes a base material layer and a pressure-sensitive adhesive layer as a layer structure.
  • the adhesive tape as an example of the object to be treated may have any suitable other layer as long as it is an adhesive tape containing a base material layer and an adhesive layer, as long as the effect of the present invention is not impaired. Such other layers may be one layer or two or more layers.
  • the adhesive tape 100 includes a base material layer 10 and an adhesive layer 20.
  • the adhesive tape 100 includes a base material layer 10, an adhesive layer 20, and a release film 30.
  • the release film is also referred to as a separator.
  • any appropriate thickness can be adopted as long as the effect of the present invention is not impaired.
  • Such a thickness is preferably 5 ⁇ m to 2000 ⁇ m.
  • Base material a base material formed from any suitable material can be adopted as long as the effects of the present invention are not impaired.
  • suitable materials include plastic films, non-woven fabrics, papers, metal foils, woven fabrics, rubber sheets, foam sheets, and laminates thereof (particularly, laminates including plastic films).
  • plastic film examples include a plastic film composed of a polyester resin such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polybutylene terephthalate (PBT); polyethylene (PE), polypropylene (PP), and polymethyl.
  • PMP penten
  • EVA ethylene-vinyl acetate copolymer
  • PVC polyvinyl chloride
  • Plastic film Plastic film; Plastic film composed of vinyl acetate resin; Plastic film composed of polycarbonate (PC); Plastic film composed of polyphenylene sulfide (PPS); Polyamide (nylon), Total aromatic polyamide (aramid) ) Etc.; plastic film composed of amide-based resin; plastic film composed of polyimide-based resin; plastic film composed of polyether ether ketone (PEEK); olefin-based such as polyethylene (PE) and polypropylene (PP) Plastic film composed of resin; polytetrafluoroethylene, polychlorotrifluoroethylene, polyvinyl fluoride, polyvinylidene fluoride, tetrafluoroethylene-hexafluoropropylene copolymer, chlorofluoroethylene-vinylidene fluoride copolymer, etc. Examples thereof include a plastic film made of a fluororesin or the like.
  • non-woven fabric examples include non-woven fabrics made of natural fibers having heat resistance such as non-woven fabrics containing Manila hemp; synthetic resin non-woven fabrics such as polypropylene resin non-woven fabrics, polyethylene resin non-woven fabrics and ester resin non-woven fabrics.
  • the base material may be only one layer or two or more layers as the base material layer.
  • the thickness of the base material is preferably 5 ⁇ m to 250 ⁇ m in that the effect of the present invention can be more exhibited as the base material layer.
  • the base material may be surface-treated.
  • the surface treatment include corona treatment, plasma treatment, chromic acid treatment, ozone exposure, flame exposure, high-voltage impact exposure, ionizing radiation treatment, coating treatment with an undercoat agent, and the like.
  • the base material may contain any suitable other additives as long as the effects of the present invention are not impaired.
  • any suitable pressure-sensitive adhesive may be adopted as long as the effects of the present invention are not impaired.
  • the pressure-sensitive adhesive may have only one layer or two or more layers as the pressure-sensitive adhesive layer.
  • the pressure-sensitive adhesive is in the form of a pressure-sensitive adhesive layer contained in the pressure-sensitive adhesive tape, in the form of a pressure-sensitive adhesive remaining on an adherend, or adheres to manufacturing equipment such as a polymerization pot, a coating machine, or a coating roll. Since it may be a polymerized adhesive, its size and shape vary.
  • the form of the pressure-sensitive adhesive layer contained in the pressure-sensitive adhesive tape is preferably 1 ⁇ m to 2000 ⁇ m in that the effect of the present invention can be more exhibited.
  • the pressure-sensitive adhesive is preferably composed of at least one selected from the group consisting of acrylic pressure-sensitive adhesives, urethane-based pressure-sensitive adhesives, rubber-based pressure-sensitive adhesives, and silicone-based pressure-sensitive adhesives.
  • the adhesive can be formed by any suitable method.
  • a method for example, at least one selected from the group consisting of a pressure-sensitive adhesive composition (acrylic pressure-sensitive adhesive composition, urethane-based pressure-sensitive adhesive composition, rubber-based pressure-sensitive adhesive composition, silicone-based pressure-sensitive adhesive composition).
  • a pressure-sensitive adhesive composition (acrylic pressure-sensitive adhesive composition, urethane-based pressure-sensitive adhesive composition, rubber-based pressure-sensitive adhesive composition, silicone-based pressure-sensitive adhesive composition).
  • a pressure-sensitive adhesive composition (acrylic pressure-sensitive adhesive composition, urethane-based pressure-sensitive adhesive composition, rubber-based pressure-sensitive adhesive composition, silicone-based pressure-sensitive adhesive composition). ) Is applied on any suitable substrate, heated and dried as necessary, and cured as needed to form an adhesive (specifically, an adhesive layer) on the substrate. There is a way to do it.
  • Examples of such an application method include a gravure roll coater, a reverse roll coater, a kiss roll coater, a dip roll coater, a bar coater, a knife coater, an air knife coater, a spray coater, a comma coater, a direct coater, and a roll brush coater. Method can be mentioned.
  • the acrylic pressure-sensitive adhesive is formed from an acrylic pressure-sensitive adhesive composition.
  • the acrylic pressure-sensitive adhesive composition preferably contains an acrylic polymer and a cross-linking agent in that the effects of the present invention can be more exhibited.
  • Acrylic polymers can be referred to as so-called base polymers in the field of acrylic pressure-sensitive adhesives.
  • the acrylic polymer may be only one kind or two or more kinds.
  • the content ratio of the acrylic polymer in the acrylic pressure-sensitive adhesive composition is preferably 50% by weight to 100% by weight, more preferably 60% by weight to 100% by weight, still more preferably 70 in terms of solid content. It is from% by weight to 100% by weight, particularly preferably 80% by weight to 100% by weight, and most preferably 90% by weight to 100% by weight.
  • acrylic polymer any suitable acrylic polymer can be adopted as long as the effect of the present invention is not impaired.
  • the weight average molecular weight of the acrylic polymer is preferably 100,000 to 3,000,000, more preferably 150,000 to 2,000,000, in that the effects of the present invention can be more exhibited. It is more preferably 200,000 to 1,500,000, and particularly preferably 250,000 to 1,000,000.
  • a (meth) acrylic acid alkyl ester having 4 to 12 carbon atoms in the alkyl group of the (component a) alkyl ester moiety is preferable in that the effect of the present invention can be more exhibited.
  • the (a component) and (b component) may be independently one kind or two or more kinds, respectively.
  • Examples of the (meth) acrylic acid alkyl ester (component a) in which the alkyl group of the alkyl ester moiety has 4 to 12 carbon atoms include n-butyl (meth) acrylic acid, isobutyl (meth) acrylic acid, and (meth).
  • n-butyl (meth) acrylate and 2-ethylhexyl (meth) acrylate are preferable, and n-butyl acrylate and acrylic are more preferable in that the effects of the present invention can be further exhibited.
  • 2-Ethylhexyl acid 2-Ethylhexyl acid.
  • At least one (b component) selected from the group consisting of (meth) acrylic acid ester having an OH group and (meth) acrylic acid for example, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, and the like.
  • examples thereof include (meth) acrylic acid ester having an OH group such as hydroxybutyl (meth) acrylic acid, and (meth) acrylic acid.
  • hydroxyethyl (meth) acrylate and (meth) acrylic acid are preferable, and hydroxyethyl acrylate and acrylic acid are more preferable, in that the effects of the present invention can be more exhibited.
  • the composition (A) may contain a copolymerizable monomer other than the component (a) and the component (b).
  • the copolymerizable monomer may be only one kind or two or more kinds. Examples of such a copolymerizable monomer include itaconic acid, maleic acid, fumaric acid, crotonic acid, isocrotonic acid, and acid anhydrides thereof (for example, an acid anhydride group-containing monomer such as maleic anhydride and itaconic anhydride).
  • carboxyl group-containing monomers excluding (meth) acrylic acid); (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N-methylol (meth) acrylamide, N-methoxymethyl (meth) acrylamide.
  • Group-containing monomer Phosphoric acid group-containing monomer such as 2-hydroxyethylacryloyl phosphate; Iimide group-containing monomer such as cyclohexylmaleimide and isopropylmaleimide; isocyanate group-containing monomer such as 2-methacryloyloxyethyl isocyanate; Cyclopentyl (meth) acrylate, (Meta) acrylic acid ester having an alicyclic hydrocarbon group such as cyclohexyl (meth) acrylate and isobornyl (meth) acrylate; aromatics such as phenyl (meth) acrylate, phenoxyethyl (meth) acrylate and benzyl (meth) acrylate.
  • Phosphoric acid group-containing monomer such as 2-hydroxyethylacryloyl phosphate
  • Iimide group-containing monomer such as cyclohexylmaleimide and isopropylmaleimide
  • (Meta) acrylic acid ester having a hydrocarbon group vinyl ester such as vinyl acetate and vinyl propionate; aromatic vinyl compound such as styrene and vinyl toluene; olefins and dienes such as ethylene, butadiene, isoprene and isobutylene; vinyl Vinyl ethers such as alkyl ethers; vinyl chloride; and the like can be mentioned.
  • a polyfunctional monomer can also be adopted.
  • the polyfunctional monomer means a monomer having two or more ethylenically unsaturated groups in one molecule.
  • any suitable ethylenically unsaturated group can be adopted as long as the effect of the present invention is not impaired.
  • examples of such an ethylenically unsaturated group include radically polymerizable functional groups such as a vinyl group, a propenyl group, an isopropenyl group, a vinyl ether group (vinyloxy group) and an allyl ether group (allyloxy group).
  • polyfunctional monomer examples include hexanediol di (meth) acrylate, butanediol di (meth) acrylate, (poly) ethylene glycol di (meth) acrylate, (poly) propylene glycol di (meth) acrylate, and neopentyl glycol.
  • Examples thereof include (meth) acrylate, vinyl (meth) acrylate, divinylbenzene, epoxy acrylate, polyester acrylate, and urethane acrylate.
  • a polyfunctional monomer may be only one kind, or may be two or more kinds.
  • (meth) acrylic acid alkoxyalkyl ester can also be adopted.
  • the (meth) acrylate alkoxyalkyl ester include (meth) acrylate 2-methoxyethyl, (meth) acrylate 2-ethoxyethyl, (meth) acrylate methoxytriethylene glycol, and (meth) acrylate 3-. Examples thereof include methoxypropyl, 3-ethoxypropyl (meth) acrylate, 4-methoxybutyl (meth) acrylate, and 4-ethoxybutyl (meth) acrylate.
  • the (meth) acrylic acid alkoxyalkyl ester may be only one kind or two or more kinds.
  • the content of the (meth) acrylic acid alkyl ester (component a) in which the alkyl group of the alkyl ester moiety has 4 to 12 carbon atoms is a monomer constituting the acrylic polymer in that the effect of the present invention can be further exhibited. It is preferably 50% by weight or more, more preferably 60% by weight to 100% by weight, still more preferably 70% by weight to 100% by weight, and particularly preferably 80% by weight, based on the total amount of the components (100% by weight). It is 100% by weight by weight.
  • the content of at least one (b component) selected from the group consisting of (meth) acrylic acid ester having an OH group and (meth) acrylic acid makes the acrylic polymer more effective in terms of exhibiting the effects of the present invention. It is preferably 0.1% by weight or more, more preferably 1.0% by weight to 50% by weight, still more preferably 1.5% by weight to 40% by weight, based on the total amount of the constituent monomer components (100% by weight). It is% by weight, and particularly preferably 2.0% by weight to 30% by weight.
  • composition (A) may contain any suitable other components as long as the effects of the present invention are not impaired.
  • suitable other components include polymerization initiators, chain transfer agents, solvents and the like.
  • any appropriate content may be adopted as long as the effect of the present invention is not impaired.
  • the polymerization initiator a thermal polymerization initiator, a photopolymerization initiator (photoinitiator), or the like can be adopted depending on the type of the polymerization reaction.
  • the polymerization initiator may be only one kind or two or more kinds.
  • the thermal polymerization initiator can be preferably used when an acrylic polymer is obtained by solution polymerization.
  • a thermal polymerization initiator examples include an azo-based polymerization initiator, a peroxide-based polymerization initiator (for example, dibenzoyl peroxide, tert-butyl permalate, etc.), a redox-based polymerization initiator, and the like. ..
  • the azo-based initiator disclosed in JP-A-2002-69411 is particularly preferable.
  • Such an azo-based polymerization initiator is preferable in that the decomposition product of the polymerization initiator does not easily remain in the acrylic polymer as a portion that causes the generation of heat-generating gas (out gas).
  • the azo-based polymerization initiator include 2,2'-azobisisobutyronitrile (hereinafter, may be referred to as AIBN) and 2,2'-azobis-2-methylbutyronitrile (hereinafter, referred to as AMBN). , 2,2'-azobis (2-methylpropionic acid) dimethyl, 4,4'-azobis-4-cyanovalerian acid and the like.
  • the amount of the azo-based polymerization initiator used is preferably 0.01 parts by weight to 5.0 parts by weight, more preferably 0.05 parts by weight, based on the total amount of the monomer components (100 parts by weight) constituting the acrylic polymer. It is from parts by weight to 4.0 parts by weight, more preferably 0.1 parts by weight to 3.0 parts by weight, particularly preferably 0.15 parts by weight to 3.0 parts by weight, and most preferably 0. It is 20 parts by weight to 2.0 parts by weight.
  • the photopolymerization initiator can be preferably used when an acrylic polymer is obtained by active energy ray polymerization.
  • the photopolymerization initiator include a benzoin ether-based photopolymerization initiator, an acetophenone-based photopolymerization initiator, an ⁇ -ketol-based photopolymerization initiator, an aromatic sulfonyl chloride-based photopolymerization initiator, and a photoactive oxime-based photopolymerization initiator.
  • Examples thereof include agents, benzoin-based photopolymerization initiators, benzyl-based photopolymerization initiators, benzophenone-based photopolymerization initiators, ketal-based photopolymerization initiators, thioxanthone-based photopolymerization initiators, and the like.
  • benzoin ether-based photopolymerization initiator examples include benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 2,2-dimethoxy-1,2-diphenylethan-1-one, and anisole.
  • examples include methyl ether.
  • examples of the acetophenone-based photopolymerization initiator include 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1-hydroxycyclohexylphenylketone, 4-phenoxydichloroacetophenone, and 4- (t-butyl). Examples include dichloroacetophenone.
  • Examples of the ⁇ -ketol-based photopolymerization initiator include 2-methyl-2-hydroxypropiophenone, 1- [4- (2-hydroxyethyl) phenyl] -2-methylpropane-1-one, and the like. ..
  • Examples of the aromatic sulfonyl chloride-based photopolymerization initiator include 2-naphthalene sulfonyl chloride and the like.
  • Examples of the photoactive oxime-based photopolymerization initiator include 1-phenyl-1,1-propanedione-2- (o-ethoxycarbonyl) -oxime.
  • Examples of the benzoin-based photopolymerization initiator include benzoin and the like.
  • Examples of the benzyl-based photopolymerization initiator include benzyl and the like.
  • Examples of the benzophenone-based photopolymerization initiator include benzophenone, benzoylbenzoic acid, 3,3'-dimethyl-4-methoxybenzophenone, polyvinylbenzophenone, ⁇ -hydroxycyclohexylphenylketone and the like.
  • Examples of the ketal-based photopolymerization initiator include benzyldimethyl ketal and the like.
  • thioxanthone-based photopolymerization initiator examples include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, and dodecylthioxanthone.
  • the amount of the photopolymerization initiator used is preferably 0.01 parts by weight to 3.0 parts by weight, more preferably 0.015 parts by weight, based on the total amount of the monomer components (100 parts by weight) constituting the acrylic polymer. It is from parts by weight to 2.0 parts by weight, more preferably 0.02 parts by weight to 1.5 parts by weight, particularly preferably 0.025 parts by weight to 1.0 part by weight, and most preferably 0.03 parts by weight. It is from parts by weight to 0.50 parts by weight.
  • the acrylic pressure-sensitive adhesive composition may contain a cross-linking agent.
  • a cross-linking agent By using a cross-linking agent, the cohesive force of the acrylic pressure-sensitive adhesive can be improved, and the effect of the present invention can be further exhibited.
  • the cross-linking agent may be only one kind or two or more kinds.
  • the cross-linking agent examples include a polyfunctional isocyanate-based cross-linking agent, an epoxy-based cross-linking agent, a melamine-based cross-linking agent, a peroxide-based cross-linking agent, a urea-based cross-linking agent, a metal alkoxide-based cross-linking agent, a metal chelate-based cross-linking agent, and a metal salt.
  • examples thereof include a system-based cross-linking agent, a carbodiimide-based cross-linking agent, an oxazoline-based cross-linking agent, an aziridine-based cross-linking agent, and an amine-based cross-linking agent.
  • at least one (c component) selected from the group consisting of a polyfunctional isocyanate-based cross-linking agent and an epoxy-based cross-linking agent is preferable in that the effects of the present invention can be further exhibited.
  • polyfunctional isocyanate-based cross-linking agent examples include lower aliphatic polyisocyanates such as 1,2-ethylene diisocyanate, 1,4-butylene diisocyanate, and 1,6-hexamethylene diisocyanate; cyclopentylene diisocyanate, cyclohexylene diisocyanate, and the like.
  • Alicyclic polyisocyanates such as isophorone diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated xylene diisocyanate; 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, xylylene diisocyanate, etc.
  • Aromatic polyisocyanates and the like examples include trimethylolpropane / tolylene diisocyanate adduct (manufactured by Nippon Polyurethane Industry Co., Ltd., trade name “Coronate L”) and trimethylolpropane / hexamethylene diisocyanate adduct (Nippon Polyurethane Industry Co., Ltd.).
  • epoxy-based cross-linking agent examples include N, N, N', N'-tetraglycidyl-m-xylene diamine, diglycidyl aniline, and 1,3-bis (N, N-diglycidylamino).
  • any appropriate content can be adopted as long as the effect of the present invention is not impaired.
  • a content is preferably 0.1 part by weight to 5.0 parts by weight with respect to the solid content (100 parts by weight) of the acrylic polymer, for example, in that the effect of the present invention can be more exhibited. It is more preferably 0.2 parts by weight to 4.5 parts by weight, further preferably 0.3 parts by weight to 4.0 parts by weight, and particularly preferably 0.4 parts by weight to 3.5 parts by weight. It is a department.
  • the acrylic pressure-sensitive adhesive composition may contain any suitable other components as long as the effects of the present invention are not impaired.
  • suitable other components include polymer components other than acrylic polymers, cross-linking accelerators, cross-linking catalysts, silane coupling agents, tackifier resins (rosin derivatives, polyterpene resins, petroleum resins, oil-soluble phenols, etc.), and the like.
  • Anti-aging agents inorganic fillers, organic fillers, metal powders, colorants (pigments, dyes, etc.), foils, UV absorbers, antioxidants, light stabilizers, chain transfer agents, plasticizers, softeners, Examples thereof include surfactants, antistatic agents, conductive agents, stabilizers, surface lubricants, leveling agents, corrosion inhibitors, heat stabilizers, polymerization inhibitors, lubricants, solvents, catalysts and the like.
  • the urethane-based pressure-sensitive adhesive is formed from a urethane-based pressure-sensitive adhesive composition.
  • the urethane-based pressure-sensitive adhesive composition preferably contains at least one selected from the group consisting of urethane prepolymers and polyols and a cross-linking agent in that the effects of the present invention can be further exhibited.
  • At least one selected from the group consisting of urethane prepolymers and polyols can be called a so-called base polymer in the field of urethane-based pressure-sensitive adhesives.
  • the urethane prepolymer may be only one kind or two or more kinds.
  • the polyol may be only one kind or two or more kinds.
  • the urethane prepolymer is preferably a polyurethane polyol, and more preferably a polyester polyol (a1) or a polyether polyol (a2), respectively, alone or in a mixture of (a1) and (a2), in the presence of a catalyst. It is formed by reacting with the organic polyisocyanate compound (a3) under or without a catalyst.
  • polyester polyol (a1) any suitable polyester polyol can be used.
  • a polyester polyol (a1) include a polyester polyol obtained by reacting an acid component with a glycol component.
  • the acid component include terephthalic acid, adipic acid, azelaic acid, sebatic acid, phthalic anhydride, isophthalic acid, trimellitic acid and the like.
  • the glycol component include ethylene glycol, propylene glycol, diethylene glycol, butylene glycol, 1,6-hexane glycol, 3-methyl-1,5-pentanediol, 3,3'-dimethylol heptane, and polyoxyethylene glycol.
  • polyester polyol (a1) examples include polyester polyols obtained by ring-opening polymerization of lactones such as polycaprolactone, poly ( ⁇ -methyl- ⁇ -valerolactone) and polyvalerolactone.
  • the molecular weight of the polyester polyol (a1) can be from low molecular weight to high molecular weight.
  • the number average molecular weight is preferably 100 to 100,000 in that the effects of the present invention can be more exhibited. If the number average molecular weight is less than 100, the reactivity becomes high and gelation may occur easily. If the number average molecular weight exceeds 100,000, the reactivity may be lowered, and the cohesive force of the polyurethane polyol itself may be reduced.
  • the amount of the polyester polyol (a1) used is preferably 0 mol% to 90 mol% among the polyols constituting the polyurethane polyol in that the effects of the present invention can be more exhibited.
  • any suitable polyether polyol can be used.
  • examples of such a polyether polyol (a2) include ethylene oxide, propylene oxide, butylene oxide, and tetrahydrofuran using a low molecular weight polyol such as water, propylene glycol, ethylene glycol, glycerin, and trimethylolpropane as an initiator.
  • examples thereof include polyether polyols obtained by polymerizing an oxylan compound.
  • Specific examples of such a polyether polyol (a2) include polyether polyols having 2 or more functional groups, such as polypropylene glycol, polyethylene glycol, and polytetramethylene glycol.
  • the molecular weight of the polyether polyol (a2) can be from low molecular weight to high molecular weight.
  • the number average molecular weight is preferably 100 to 100,000 in that the effects of the present invention can be more exhibited. If the number average molecular weight is less than 100, the reactivity becomes high and gelation may occur easily. If the number average molecular weight exceeds 100,000, the reactivity may be lowered, and the cohesive force of the polyurethane polyol itself may be reduced.
  • the amount of the polyether polyol (a2) used is preferably 0 mol% to 90 mol% in the polyol constituting the polyurethane polyol in that the effect of the present invention can be more exhibited.
  • the polyether polyol (a2) may be partially composed of glycols such as ethylene glycol, 1,4-butanediol, neopentyl glycol, butylethylpentanediol, glycerin, trimethylolpropane, and pentaerythritol. It can be used in combination with polyvalent amines such as ethylenediamine, N-aminoethylethanolamine, isophoronediamine, and xylylenediamine.
  • glycols such as ethylene glycol, 1,4-butanediol, neopentyl glycol, butylethylpentanediol, glycerin, trimethylolpropane, and pentaerythritol. It can be used in combination with polyvalent amines such as ethylenediamine, N-aminoethylethanolamine, isophoronediamine, and xylylenedi
  • the polyether polyol (a2) only a bifunctional polyether polyol may be used, or a polyether having a number average molecular weight of 100 to 100,000 and having at least 3 or more hydroxyl groups in one molecule. Part or all of the polyol may be used. When a part or all of the polyether polyol (a2) having a number average molecular weight of 100 to 100,000 and having at least 3 or more hydroxyl groups in one molecule is used, the effect of the present invention is further exhibited. At the same time, the balance between the adhesive force and the peelability can be improved. In such a polyether polyol, if the number average molecular weight is less than 100, the reactivity becomes high and gelation may easily occur.
  • the number average molecular weight of such a polyether polyol is more preferably 100 to 10000 in that the effect of the present invention can be more exhibited.
  • organic polyisocyanate compound (a3) any suitable organic polyisocyanate compound can be used.
  • organic polyisocyanate compound (a3) include aromatic polyisocyanates, aliphatic polyisocyanates, aromatic aliphatic polyisocyanates, and alicyclic polyisocyanates.
  • aromatic polyisocyanate examples include 1,3-phenylenediocyanate, 4,4'-diphenyldiisocyanate, 1,4-phenylenediocyanate, 4,4'-diphenylmethane diisocyanate, 2,4-tolylene diisocyanate, and 2,6.
  • aliphatic polyisocyanate examples include trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, 1,2-propylene diisocyanate, 2,3-butylenediocyanate, 1,3-butylenediocyanate, and dodecamethylene diisocyanate. Examples thereof include 2,4,4-trimethylhexamethylene diisocyanate.
  • aromatic aliphatic polyisocyanate examples include ⁇ , ⁇ '-diisocyanate-1,3-dimethylbenzene, ⁇ , ⁇ '-diisocyanate-1,4-dimethylbenzene, ⁇ , ⁇ '-diisocyanate-1,4-diethylbenzene. , 1,4-Tetramethylxylylene diisocyanate, 1,3-tetramethylxylylene diisocyanate and the like.
  • Examples of the alicyclic polyisocyanate include 3-isocyanate methyl-3,5,5-trimethylcyclohexylisocyanate, 1,3-cyclopentanediisocyanate, 1,3-cyclohexanediisocyanate, 1,4-cyclohexanediisocyanate, and methyl-2. , 4-Cyclohexanediisocyanate, methyl-2,6-cyclohexanediisocyanate, 4,4'-methylenebis (cyclohexylisocyanate), 1,4-bis (isocyanatemethyl) cyclohexane, 1,4-bis (isocyanatemethyl) cyclohexane, etc. Be done.
  • organic polyisocyanate compound (a3) a trimethylolpropane adduct compound, a biuret compound reacted with water, a trimer having an isocyanurate ring, or the like can be used in combination.
  • Any suitable catalyst can be used as the catalyst that can be used to obtain the polyurethane polyol.
  • a catalyst include tertiary amine compounds and organometallic compounds.
  • tertiary amine compound examples include triethylamine, triethylenediamine, 1,8-diazabicyclo (5,4,0) -undecene-7 (DBU) and the like.
  • organometallic compound examples include tin-based compounds and non-tin-based compounds.
  • tin-based compound examples include dibutyltin dichloride, dibutyltin oxide, dibutyltin dibromide, dibutyltin dimalate, dibutyltin dilaurate (DBTDL), dibutyltin diacetate, dibutyltin sulfide, tributyltin sulfide, tributyltin oxide, and tributyl.
  • Examples thereof include tin acetate, triethyl tin ethoxide, tributyl tin ethoxide, dioctyl tin oxide, tributyl tin chloride, tributyl tin trichloroacetate, tin 2-ethylhexanoate and the like.
  • non-tin compound examples include titanium compounds such as dibutyl titanium dichloride, tetrabutyl titanate, and butoxytitanium trichloride; lead compounds such as lead oleate, lead 2-ethylhexanoate, lead benzoate, and lead naphthenate.
  • titanium compounds such as dibutyl titanium dichloride, tetrabutyl titanate, and butoxytitanium trichloride
  • lead compounds such as lead oleate, lead 2-ethylhexanoate, lead benzoate, and lead naphthenate.
  • Iron compounds such as iron 2-ethylhexanoate and iron acetylacetonate
  • Cobalt compounds such as cobalt benzoate and cobalt 2-ethylhexanate
  • Zinc compounds such as zinc naphthenate and zinc 2-ethylhexanate
  • Zylon-based compounds such as zirconium naphthenate; and the like.
  • Examples of the combination of such two types of catalysts include tertiary amine / organic metal-based, tin-based / non-tin-based, and tin-based / tin-based, preferably tin-based / tin-based, and more preferably.
  • the tin 2-ethylhexanoate / dibutyltin dilaurate is preferably less than 1 and more preferably 0.2 to 0.6 by weight. When the compounding ratio is 1 or more, gelation may easily occur due to the balance of catalytic activity.
  • the amount of the catalyst used is preferably 0.01 with respect to the total amount of the polyester polyol (a1), the polyether polyol (a2) and the organic polyisosianate compound (a3). It is from% by weight to 1.0% by weight.
  • the reaction temperature is preferably less than 100 ° C, more preferably 85 ° C to 95 ° C. If the temperature is 100 ° C. or higher, it may be difficult to control the reaction rate and the crosslinked structure, and it may be difficult to obtain a polyurethane polyol having a predetermined molecular weight.
  • the reaction temperature is preferably 100 ° C. or higher, more preferably 110 ° C. or higher. Further, when the polyurethane polyol is obtained without a catalyst, it is preferable to react for 3 hours or more.
  • a method for obtaining a polyurethane polyol for example, 1) a method of charging a polyester polyol, a polyether polyol, a catalyst, and an organic polyisocyanate into a flask in full quantity, and 2) a method of charging a polyester polyol, a polyether polyol, and a catalyst into a flask and charging an organic polyisocianate.
  • the method 2) is preferable in controlling the reaction.
  • Any suitable solvent can be used to obtain the polyurethane polyol.
  • a solvent include methyl ethyl ketone, ethyl acetate, toluene, xylene, acetone and the like.
  • toluene is preferable.
  • polyol examples include polyester polyol, polyether polyol, polycaprolactone polyol, polycarbonate polyol, and castor oil-based polyol.
  • the polyol is more preferably a polyether polyol.
  • the polyester polyol can be obtained, for example, by an esterification reaction between a polyol component and an acid component.
  • polyol component examples include ethylene glycol, diethylene glycol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, and 2-butyl-2-ethyl-1.
  • the acid component examples include succinic acid, methylsuccinic acid, adipic acid, piceric acid, azelaic acid, sebacic acid, 1,12-dodecanedioic acid, 1,14-tetradecanedioic acid, dimer acid, 2-methyl-1, 4-Cyclohexanedicarboxylic acid, 2-ethyl-1,4-cyclohexanedicarboxylic acid, terephthalic acid, isophthalic acid, phthalic acid, 1,4-naphthalenedicarboxylic acid, 4,4'-biphenyldicarboxylic acid, acid anhydrides thereof And so on.
  • polyether polyol examples include water, low molecular weight polyols (propylene glycol, ethylene glycol, glycerin, trimethylolpropane, pentaerythritol, etc.), bisphenols (bisphenol A, etc.), dihydroxybenzene (catechol, resorcin, hydroquinone, etc.), etc.
  • examples thereof include a polyether polyol obtained by addition-polymerizing an alkylene oxide such as ethylene oxide, propylene oxide, and butylene oxide.
  • Specific examples thereof include polyethylene glycol, polypropylene glycol and polytetramethylene glycol.
  • polycaprolactone polyol examples include a caprolactone-based polyester diol obtained by ring-opening polymerization of a cyclic ester monomer such as ⁇ -caprolactone and ⁇ -valerolactone.
  • polycarbonate polyol examples include a polycarbonate polyol obtained by subjecting the above-mentioned polyol component and phosgen to a polycondensation reaction; the above-mentioned polyol component and dimethyl carbonate, diethyl carbonate, diprovyl carbonate, diisopropyl carbonate, dibutyl carbonate, ethylbutyl carbonate, ethylene carbonate, Polycarbonate polyol obtained by ester exchange condensation with carbonic acid diesters such as propylene carbonate, diphenyl carbonate, dibenzyl carbonate; copolymerized polycarbonate polyol obtained by using two or more of the above-mentioned polyol components in combination; the above-mentioned various polycarbonate polyols and carboxyl groups.
  • Polycarbonate polyol obtained by esterifying the contained compound Polycarbonate polyol obtained by etherifying the various polycarbonate polyols and the hydroxyl group-containing compound; Obtained by performing an ester exchange reaction between the various polycarbonate polyols and the ester compound.
  • Polycarbonate-based polycarbonate polyol obtained by a polycondensation reaction between the various polycarbonate polyols and a dicarboxylic acid compound Examples thereof include a copolymerized polyether polycarbonate polyol obtained by copolymerizing a polyol and an alkylene oxide.
  • castor oil-based polyol examples include castor oil-based polyol obtained by reacting a castor oil fatty acid with the above-mentioned polyol component. Specific examples thereof include castor oil-based polyols obtained by reacting castor oil fatty acid with polypropylene glycol.
  • the number average molecular weight Mn of the polyol is preferably 300 to 100,000, more preferably 400 to 75,000, still more preferably 450 to 50,000, and particularly preferably 500, in that the effects of the present invention can be more exhibited. It is ⁇ 30,000.
  • the polyol preferably contains a polyol (A1) having three OH groups and having a number average molecular weight Mn of 300 to 100,000 in that the effects of the present invention can be further exhibited.
  • the polyol (A1) may be only one kind or two or more kinds.
  • the content ratio of the polyol (A1) in the polyol is preferably 5% by weight or more, more preferably 25% by weight to 100% by weight, still more preferably 50%, in that the effect of the present invention can be more exhibited. It is 100% by weight by weight.
  • the number average molecular weight Mn of the polyol (A1) is preferably 1000 to 100,000, more preferably more than 1000 and 80,000 or less, still more preferably 1100 to 70,000 in that the effect of the present invention can be more exhibited. It is more preferably 1200 to 60000, still more preferably 1300 to 50000, still more preferably 1400 to 40,000, still more preferably 1500 to 35000, particularly preferably 1700 to 32000, and most preferably. It is 2000 to 30000.
  • the polyol may contain a polyol (A2) having 3 or more OH groups and having a number average molecular weight Mn of 20000 or less.
  • the polyol (A2) may be only one kind or two or more kinds.
  • the number average molecular weight Mn of the polyol (A2) is preferably 100 to 20000, more preferably 150 to 10000, still more preferably 200 to 7500, and particularly, in that the effect of the present invention can be more exhibited. It is preferably 300 to 6000, and most preferably 300 to 5000.
  • the polyol (A2) is preferably a polyol having 3 OH groups (triol), a polyol having 4 OH groups (tetraol), and 5 OH groups in that the effects of the present invention can be more exhibited. Examples thereof include a polyol having (pentaol) and a polyol having 6 OH groups (hexaol).
  • the total amount of the polyol (A2) as a polyol having 4 OH groups (tetraol), a polyol having 5 OH groups (pentaol), and a polyol having 6 OH groups (hexaol) is the total amount of the present invention.
  • the content ratio in the polyol is preferably 70% by weight or less, more preferably 60% by weight or less, still more preferably 40% by weight or less, and particularly preferably 30% by weight in that the effect can be more exhibited. % Or less.
  • the content ratio of the polyol (A2) in the polyol is preferably 95% by weight or less, and more preferably 0% by weight to 75% by weight, in that the effect of the present invention can be more exhibited.
  • the content ratio of the polyol (A2) having 4 or more OH groups and having a number average molecular weight Mn of 20000 or less is preferably 70 weight by weight with respect to the entire polyol in that the effect of the present invention can be more exhibited. %, More preferably 60% by weight or less, still more preferably 50% by weight or less, particularly preferably 40% by weight or less, and most preferably 30% by weight or less.
  • the urethane-based pressure-sensitive adhesive composition preferably contains a cross-linking agent in that the effects of the present invention can be more exhibited.
  • the urethane prepolymer and the polyol as the base polymer can each be a component of the urethane-based pressure-sensitive adhesive composition in combination with a cross-linking agent.
  • the cross-linking agent to be combined with the urethane prepolymer as the base polymer and the polyol is preferably a polyfunctional isocyanate-based cross-linking agent in that the effects of the present invention can be further exhibited.
  • any suitable polyfunctional isocyanate-based cross-linking agent that can be used for the urethanization reaction can be adopted.
  • examples of such a polyfunctional isocyanate-based cross-linking agent include lower aliphatic polyisocyanates such as 1,2-ethylene diisocyanate, 1,4-butylene diisocyanate, and 1,6-hexamethylene diisocyanate; cyclopentylene diisocyanate and cyclohexyl.
  • Alicyclic polyisocyanates such as sirylene diisocyanate, isophorone diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated xylene diisocyanate; 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, xyli
  • aromatic polyisocyanates such as range isocyanate.
  • polyfunctional isocyanate-based cross-linking agent examples include trimethylolpropane / tolylene diisocyanate adduct (manufactured by Nippon Polyurethane Industry Co., Ltd., trade name “Coronate L”) and trimethylolpropane / hexamethylene diisocyanate adduct (Nippon Polyurethane Industry Co., Ltd.).
  • the urethane-based pressure-sensitive adhesive composition may contain any suitable other components as long as the effects of the present invention are not impaired.
  • suitable other components include polymer components other than urethane prepolymers and polyols, cross-linking accelerators, cross-linking catalysts, silane coupling agents, tackifier resins (rosin derivatives, polyterpene resins, petroleum resins, oil-soluble phenols, etc.).
  • Anti-aging agents Inorganic fillers, Organic fillers, Metal powders, Colorants (pigments, dyes, etc.), Foil-like materials, Anti-deterioration agents, Chain transfer agents, Plastics, Softeners, Surface active agents, Antistatic Examples thereof include agents, conductive agents, stabilizers, surface lubricants, leveling agents, corrosion inhibitors, heat-resistant stabilizers, polymerization inhibitors, lubricants, solvents, catalysts and the like.
  • the urethane-based pressure-sensitive adhesive composition preferably contains a deterioration inhibitor in that the effects of the present invention can be more exhibited.
  • the deterioration inhibitor may be only one kind or two or more kinds.
  • Preferred examples of the deterioration inhibitor include an antioxidant, an ultraviolet absorber, and a light stabilizer in that the effects of the present invention can be more exhibited.
  • antioxidant examples include a radical chain inhibitor, a peroxide decomposing agent, and the like.
  • radical chain inhibitor examples include phenol-based antioxidants and amine-based antioxidants.
  • phenol-based antioxidant examples include monophenol-based antioxidants, bisphenol-based antioxidants, and polymer-type phenol-based antioxidants.
  • monophenolic antioxidant examples include 2,6-di-t-butyl-p-cresol, butylated hydroxyanisole, 2,6-di-t-butyl-4-ethylphenol, and stear- ⁇ - ( 3,5-Di-t-butyl-4-hydroxyphenyl) propionate and the like can be mentioned.
  • bisphenol-based antioxidant examples include 2,2'-methylenebis (4-methyl-6-t-butylphenol), 2,2'-methylenebis (4-ethyl-6-t-butylphenol), and 4,4'.
  • -Thiobis (3-methyl-6-t-butylphenol), 4,4'-butylidenebis (3-methyl-6-t-butylphenol), 3,9-bis [1,1-dimethyl-2- [ ⁇ - ( ⁇ - ( 3-t-Butyl-4-hydroxy-5-methylphenyl) propionyloxy] ethyl] 2,4,8,10-tetraoxaspiro [5,5] undecane and the like can be mentioned.
  • the high molecular weight phenolic antioxidant include 1,1,3-tris (2-methyl-4-hydroxy-5-t-butylphenyl) butane, 1,3,5-trimethyl-2,4.
  • Examples of the peroxide decomposing agent include sulfur-based antioxidants and phosphorus-based antioxidants.
  • Examples of the sulfur-based antioxidant include dilauryl 3,3'-thiodipropionate, dimyristyl 3,3'-thiodipropionate, and distearyl 3,3'-thiodipropionate.
  • Examples of the phosphorus-based antioxidant include triphenylphosphine, diphenylisodecylphosphite, phenyldiisodecylphosphite and the like.
  • ultraviolet absorber examples include benzophenone-based ultraviolet absorbers, benzotriazole-based ultraviolet absorbers, salicylic acid-based ultraviolet absorbers, oxalic acid anilides-based ultraviolet absorbers, cyanoacrylate-based ultraviolet absorbers, and triazine-based ultraviolet absorbers. Be done.
  • benzophenone-based ultraviolet absorber examples include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, and 2,2'.
  • Examples include methane.
  • benzotriazole-based ultraviolet absorber examples include 2- (2'-hydroxy-5'-methylphenyl) benzotriazole, 2- (2'-hydroxy-5'-tert-butylphenyl) benzotriazole, 2-( 2'-Hydroxy-3', 5'-di-tert-butylphenyl) benzotriazole, 2- (2'-hydroxy-3'-tert-butyl-5'-methylphenyl) -5-chlorobenzotriazole, 2 -(2'-Hydroxy-3', 5'-di-tert-butylphenyl) 5-chlorobenzotriazole, 2- (2'-hydroxy-3', 5'-di-tert-amylphenyl) benzotriazole, 2- (2'-Hydroxy-4'-octoxyphenyl) benzotriazole, 2- [2'-hydroxy-3'-(3'', 4', 5'', 6'', -tetrahydr
  • salicylic acid-based ultraviolet absorber examples include phenylsalicylate, p-tert-butylphenylsalicylate, and p-octylphenylsalicylate.
  • Examples of the cyanoacrylate-based ultraviolet absorber include 2-ethylhexyl-2-cyano-3,3'-diphenyl acrylate and ethyl-2-cyano-3,3'-diphenyl acrylate.
  • Examples of the light stabilizer include hindered amine-based light stabilizers and ultraviolet stabilizers.
  • Examples of the hindered amine-based light stabilizer include bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, and methyl. -1,2,2,6,6-pentamethyl-4-piperidyl sebacate and the like can be mentioned.
  • Examples of the ultraviolet stabilizer include nickel bis (octylphenyl) sulfide, [2,2'-thiobis (4-tert-octylphenolate)] -n-butylamine nickel, and nickel complex-3,5-di-tert-. Examples thereof include butyl-4-hydroxybenzyl-phosphate monoethylate, benzoate type quencher, nickel-dibutyldithiocarbamate and the like.
  • the urethane prepolymer may be only one kind or two or more kinds.
  • the polyfunctional isocyanate-based cross-linking agent may be only one kind or two or more kinds.
  • a method for forming a urethane-based polymer from a urethane-based pressure-sensitive adhesive composition containing a urethane prepolymer and a polyfunctional isocyanate-based cross-linking agent there is a method for producing a urethane-based polymer using a so-called "urethane prepolymer" as a raw material.
  • any suitable manufacturing method can be adopted.
  • the number average molecular weight Mn of the urethane prepolymer is preferably 3000 to 1000000 in that the effect of the present invention can be more exhibited.
  • the equivalent ratio of NCO group to OH group in the urethane prepolymer and the polyfunctional isocyanate-based cross-linking agent is preferably 5.0 or less as the NCO group / OH group in that the effect of the present invention can be further exhibited. It is more preferably 0.01 to 4.75, still more preferably 0.02 to 4.5, particularly preferably 0.03 to 4.25, and most preferably 0.05 to 4.0. be.
  • the content ratio of the polyfunctional isocyanate-based cross-linking agent is preferably 0.01 parts by weight to 30 parts by weight with respect to 100 parts by weight of the urethane prepolymer in that the effect of the present invention can be more exhibited.
  • weight it is more preferably 0.05 parts by weight to 25 parts by weight, further preferably 0.1 parts by weight to 20 parts by weight, and particularly preferably 0.5 parts by weight to 17.5 parts by weight. Most preferably, it is 1 part by weight to 15 parts by weight.
  • the polyol may be only one kind or two or more kinds.
  • the polyfunctional isocyanate-based cross-linking agent may be only one kind or two or more kinds.
  • the equivalent ratio of NCO group to OH group in the polyol and the polyfunctional isocyanate-based cross-linking agent is preferably 5.0 or less as the NCO group / OH group in that the effect of the present invention can be further exhibited, which is more preferable.
  • the content ratio of the polyfunctional isocyanate-based cross-linking agent is preferably 1.0 part by weight to 30 parts by weight with respect to 100 parts by weight of the polyol, in that the effect of the present invention can be further exhibited. It is more preferably 1.5 parts by weight to 27 parts by weight, further preferably 2.0 parts by weight to 25 parts by weight, and particularly preferably 2.3 parts by weight to 23 parts by weight, most preferably. Is 2.5 parts by weight to 20 parts by weight.
  • the urethane-based polymer formed from the urethane-based pressure-sensitive adhesive composition containing a polyol and a polyfunctional isocyanate-based cross-linking agent is specifically preferably a urethane-based pressure-sensitive adhesive composition containing a polyol and a polyfunctional isocyanate-based cross-linking agent. It is formed by curing an object.
  • a method for forming a urethane-based polymer by curing a urethane-based pressure-sensitive adhesive composition containing a polyol and a polyfunctional isocyanate-based cross-linking agent an effect of the present invention such as a urethanization reaction method using bulk polymerization or solution polymerization is effective. Any suitable method can be adopted as long as it does not impair.
  • a catalyst is preferably used to cure the urethane-based pressure-sensitive adhesive composition containing the polyol and the polyfunctional isocyanate-based cross-linking agent.
  • a catalyst include organometallic compounds and tertiary amine compounds.
  • organic metal compound examples include iron compounds, tin compounds, titanium compounds, zirconium compounds, lead compounds, cobalt compounds, zinc compounds and the like.
  • iron-based compounds and tin-based compounds are preferable in terms of reaction rate and pot life of the pressure-sensitive adhesive layer.
  • iron-based compounds include iron acetylacetonate, iron 2-ethylhexanoate, and ferric nasem.
  • tin-based compound examples include dibutyltin dichloride, dibutyltin oxide, dibutyltin dibromide, dibutyltin maleate, dibutyltin dilaurate, dibutyltin diacetate, dibutyltin sulfide, tributyltin methoxyde, tributyltin acetate, and triethyltinethoxydo.
  • Examples thereof include tributyl tin ethoxydo, dioctyl tin oxide, dioctyl tin dilaurate, tributyl tin chloride, tributyl tin trichloroacetate, tin 2-ethylhexanoate and the like.
  • titanium compound examples include dibutyl titanium dichloride, tetrabutyl titanate, butoxytitanium trichloride and the like.
  • zirconium-based compound examples include zirconium naphthenate and zirconium acetylacetonate.
  • Examples of the lead-based compound include lead oleate, lead 2-ethylhexanoate, lead benzoate, and lead naphthenate.
  • cobalt-based compound examples include cobalt 2-ethylhexanoate and cobalt benzoate.
  • Examples of the zinc-based compound include zinc naphthenate and zinc 2-ethylhexanoate.
  • tertiary amine compound examples include triethylamine, triethylenediamine, 1,8-diazabisik mouth- (5,4,0) -undecene-7 and the like.
  • the catalyst may be only one type or two or more types. Further, the catalyst and the cross-linking retarder may be used in combination.
  • the amount of the catalyst is preferably 0.005 part by weight to 1.00 part by weight, more preferably 0.01 part by weight or more, based on 100 parts by weight of the polyol, in that the effect of the present invention can be more exhibited. It is 0.75 parts by weight, more preferably 0.01 parts by weight to 0.50 parts by weight, and particularly preferably 0.01 parts by weight to 0.20 parts by weight.
  • any suitable rubber-based pressure-sensitive adhesive such as the known rubber-based pressure-sensitive adhesive described in JP-A-2015-074771 can be adopted as long as the effects of the present invention are not impaired. .. These may be only one kind or two or more kinds.
  • the rubber-based pressure-sensitive adhesive may contain any suitable component as long as the effect of the present invention is not impaired.
  • any suitable silicone-based pressure-sensitive adhesive such as the known silicone-based pressure-sensitive adhesive described in JP-A-2014-047280 can be adopted as long as the effects of the present invention are not impaired. .. These may be only one kind or two or more kinds.
  • the silicone-based pressure-sensitive adhesive may contain any suitable component as long as the effect of the present invention is not impaired.
  • the thickness of the release film is preferably 5 ⁇ m to 250 ⁇ m in that the effects of the present invention can be more exhibited.
  • the release film includes a resin base film.
  • the resin base film examples include plastic films composed of polyester resins such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polybutylene terephthalate (PBT); polyethylene (PE), polypropylene (PP), and the like.
  • a plastic film composed of an olefin resin containing ⁇ -olefin as a monomer component such as polymethylpentene (PMP), ethylene-propylene copolymer, ethylene-vinyl acetate copolymer (EVA); polyvinyl chloride (PVC).
  • Plastic film composed of olefin resin; polytetrafluoroethylene, polychlorotrifluoroethylene, polyvinylfluorovinyl, polyvinylidene fluoride, tetrafluoroethylene-hexafluoropropylene copolymer, chlorofluoroethylene-vinylidene fluoride copolymer
  • the resin base film may have only one layer or two or more layers.
  • the resin base film may be a stretched one.
  • the resin base film may be surface-treated.
  • the surface treatment include corona treatment, plasma treatment, chromic acid treatment, ozone exposure, flame exposure, high-voltage impact exposure, ionizing radiation treatment, coating treatment with an undercoat agent, and the like.
  • the resin base film may contain any suitable additive as long as the effect of the present invention is not impaired.
  • the release film may have a release layer in order to enhance the releasability from the pressure-sensitive adhesive layer.
  • the release film has a release layer, the side of the release layer is directly laminated on the pressure-sensitive adhesive layer.
  • any suitable forming material can be adopted as long as the effect of the present invention is not impaired.
  • forming materials include silicone-based mold release agents, fluorine-based mold release agents, long-chain alkyl-based mold release agents, fatty acid amide-based mold release agents, and the like. Among these, a silicone-based mold release agent is preferable.
  • the release layer can be formed as a coating layer.
  • any appropriate thickness can be adopted according to the purpose as long as the effect of the present invention is not impaired.
  • Such a thickness is preferably 10 nm to 2000 nm.
  • the release layer may be only one layer or two or more layers.
  • silicone-based release layer examples include an addition reaction type silicone resin.
  • the addition reaction type silicone resin include KS-774, KS-775, KS-778, KS-779H, KS-847H, and KS-847T manufactured by Shin-Etsu Chemical Co., Ltd .; TPR-manufactured by Toshiba Silicone. 6700, TPR-6710, TPR-6721; SD7220, SD7226 manufactured by Toray Dow Corning; and the like.
  • the coating amount (after drying) of the silicone-based release layer is preferably 0.01 g / m 2 to 2 g / m 2 , more preferably 0.01 g / m 2 to 1 g / m 2, and even more preferably 0.01 g / m 2 to 1 g / m 2. It is 0.01 g / m 2 to 0.5 g / m 2 .
  • the release layer is formed, for example, by applying the above-mentioned forming material on any suitable layer by a conventionally known coating method such as reverse gravure coat, bar coat, die coat, etc., and then usually about 120 to 200 ° C. It can be carried out by curing by applying a heat treatment in. Further, if necessary, heat treatment and activation energy ray irradiation such as ultraviolet irradiation may be used in combination.
  • Adhesive tapes shown in Table 1 below were prepared.
  • a pressure-sensitive adhesive treatment liquid (13) was obtained. It is summarized in Table 2.
  • the pressure-sensitive adhesive treatment liquid according to the embodiment of the present invention or the pressure-sensitive adhesive treatment method according to the embodiment of the present invention can be effectively used to easily remove various types of pressure-sensitive adhesives, and thus a large amount can be used at a manufacturing site or the like. It can be suitably used for recycling the waste of the adhesive tape generated in the above, and when the adhesive tape is used as a process material, when the adhesive tape is peeled off from the adherend to which the adhesive tape is attached. The adhesive contained in the adhesive tape remaining on the adherend can be suitably used for easily removing the adhesive without damaging the adherend.
  • a manufacturing apparatus such as a polymerization pot, a coating machine, or a coating roll in a polymerization process or a coating process when producing a pressure-sensitive adhesive.

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PCT/JP2021/024220 2020-06-30 2021-06-25 粘着剤処理液、および粘着剤処理方法 Ceased WO2022004609A1 (ja)

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US18/013,148 US12612502B2 (en) 2020-06-30 2021-06-25 Adhesive treatment liquid, and method for treating adhesive
JP2022533965A JP7232381B2 (ja) 2020-06-30 2021-06-25 粘着剤処理液、および粘着剤処理方法
EP21832393.9A EP4174123A4 (en) 2020-06-30 2021-06-25 ADHESIVE TREATMENT LIQUID AND METHOD FOR TREATING ADHESIVE
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WO2024128141A1 (ja) * 2022-12-13 2024-06-20 日東電工株式会社 親水性ポリマーの製造方法およびアルコールの製造方法
WO2025052929A1 (ja) * 2023-09-05 2025-03-13 日東電工株式会社 粘着剤と基材の分別方法
WO2025052930A1 (ja) * 2023-09-05 2025-03-13 日東電工株式会社 粘着剤と基材の分別装置
KR20250153773A (ko) 2023-02-24 2025-10-27 다이이치 고교 세이야쿠 가부시키가이샤 박리제 및 박리 방법
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JP7860959B2 (ja) 2021-03-30 2026-05-18 日東電工株式会社 積層シート処理方法および積層シート処理装置
JPWO2022210215A1 (cg-RX-API-DMAC7.html) * 2021-03-30 2022-10-06
WO2022210215A1 (ja) * 2021-03-30 2022-10-06 日東電工株式会社 積層シート処理方法および積層シート処理装置
WO2023277018A1 (ja) * 2021-06-30 2023-01-05 日東電工株式会社 水溶性ポリマーの製造方法、吸水性ポリマーの製造方法、水溶性ポリマー、および、吸水性ポリマー
KR20230143688A (ko) * 2022-04-06 2023-10-13 주식회사모아글로벌 아크릴계 점착제 제거용 접착필름
KR102645165B1 (ko) 2022-04-06 2024-04-02 주식회사모아글로벌 아크릴계 점착제 제거용 접착필름
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WO2024128141A1 (ja) * 2022-12-13 2024-06-20 日東電工株式会社 親水性ポリマーの製造方法およびアルコールの製造方法
JP2025538288A (ja) * 2023-02-06 2025-11-27 カデル リサイクリング ラブ、 エセ． エレ． プラスチックフィルムからシリコーンコーティングを分離する方法
KR20250153773A (ko) 2023-02-24 2025-10-27 다이이치 고교 세이야쿠 가부시키가이샤 박리제 및 박리 방법
WO2025052929A1 (ja) * 2023-09-05 2025-03-13 日東電工株式会社 粘着剤と基材の分別方法
WO2025052930A1 (ja) * 2023-09-05 2025-03-13 日東電工株式会社 粘着剤と基材の分別装置

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