WO2022230936A1 - 粘着テープ及び粘着剤組成物 - Google Patents

粘着テープ及び粘着剤組成物 Download PDF

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Publication number
WO2022230936A1
WO2022230936A1 PCT/JP2022/019073 JP2022019073W WO2022230936A1 WO 2022230936 A1 WO2022230936 A1 WO 2022230936A1 JP 2022019073 W JP2022019073 W JP 2022019073W WO 2022230936 A1 WO2022230936 A1 WO 2022230936A1
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Prior art keywords
pressure
sensitive adhesive
weight
adhesive tape
less
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PCT/JP2022/019073
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English (en)
French (fr)
Japanese (ja)
Inventor
雄大 緒方
渚 辻
彰 下地頭所
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Sekisui Chemical Co Ltd
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Sekisui Chemical Co Ltd
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Application filed by Sekisui Chemical Co Ltd filed Critical Sekisui Chemical Co Ltd
Priority to EP22795849.3A priority Critical patent/EP4332193A4/en
Priority to US18/288,426 priority patent/US20240209240A1/en
Priority to CN202280007505.3A priority patent/CN116529336A/zh
Priority to KR1020237013288A priority patent/KR20240004209A/ko
Priority to JP2022535229A priority patent/JPWO2022230936A1/ja
Publication of WO2022230936A1 publication Critical patent/WO2022230936A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/04—Polymers provided for in subclasses C08C or C08F
    • C08F290/042—Polymers of hydrocarbons as defined in group C08F10/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L57/00—Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C08L57/02—Copolymers of mineral oil hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L93/00—Compositions of natural resins; Compositions of derivatives 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • 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
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • 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
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J151/06—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
    • 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
    • C09J155/00—Adhesives based on homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C09J123/00 - C09J153/00
    • C09J155/005—Homopolymers or copolymers obtained by polymerisation of macromolecular compounds terminated by a carbon-to-carbon double bond
    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • 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
    • C09J2301/312—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 parameters being the characterizing feature
    • 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
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
    • 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
    • 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
    • C09J2451/00—Presence of graft polymer

Definitions

  • the present invention relates to an adhesive tape and an adhesive composition used for the adhesive tape.
  • Adhesive tapes are used for assembly in mobile electronic devices such as mobile phones and personal digital assistants (PDAs) (for example, Patent Documents 1 and 2). Adhesive tapes are also used for bonding optical members (for example, Patent Document 3).
  • Adhesive tapes used for fixing such members are required to have both resistance to peeling (adhesive strength) and resistance to lateral displacement (holding power).
  • adhesive strength resistance to peeling
  • holding power resistance to lateral displacement
  • An object of the present invention is to provide a pressure-sensitive adhesive tape having both excellent adhesive strength and holding power, and a pressure-sensitive adhesive composition used for the pressure-sensitive adhesive tape.
  • the present invention is a pressure-sensitive adhesive tape having a pressure-sensitive adhesive layer, wherein the pressure-sensitive adhesive layer has a shear storage modulus of 4.0 ⁇ 10 4 at 100° C. measured at a measurement frequency of 1 Hz using a dynamic viscoelasticity measuring device.
  • the pressure-sensitive adhesive tape has a tensile strength of 1.0 ⁇ 10 6 Pa or more and a breaking elongation of 800% or more at 25° C. measured at a tensile speed of 300 mm/min using a tensile tester.
  • the present invention will be described in detail below.
  • the adhesive tape of the present invention is an adhesive tape having an adhesive layer, and the adhesive layer has a shear storage modulus at 100 ° C. measured at a measurement frequency of 1 Hz using a dynamic viscoelasticity measuring device (hereinafter, simply (referred to as shear storage modulus) is 4.0 ⁇ 10 4 Pa or more and 1.0 ⁇ 10 6 Pa or less.
  • shear storage modulus When the shear storage elastic modulus of the pressure-sensitive adhesive layer is within the above range, it is possible to obtain a pressure-sensitive adhesive tape with excellent holding power (resistance to lateral shift) and exhibit high holding power even at high temperatures. can.
  • the shear storage modulus of the adhesive layer is preferably 6.0 ⁇ 10 4 Pa or more, more preferably 8.0 ⁇ 10 4 Pa or more, and 8.1 ⁇ 10 4 Pa or more.
  • the shear storage modulus of the pressure-sensitive adhesive layer is adjusted according to the monomer species, polymerization ratio, molecular weight, gel fraction, presence or absence of a tackifying resin, and the type and content of the tackifying resin constituting the pressure-sensitive adhesive constituting the pressure-sensitive adhesive layer. can do.
  • the shear storage modulus of the pressure-sensitive adhesive layer can be measured by the following method. First, a measurement sample consisting of only an adhesive layer is produced. For the obtained measurement sample, using a dynamic viscoelasticity measuring device such as a viscoelasticity spectrometer (for example, DVA-200 manufactured by IT Keisoku Co., Ltd., or equivalent), 5 ° C. in a slow heating shear deformation mode. /min, the measurement frequency is 1 Hz, and the storage modulus at 100°C is measured when the dynamic viscoelasticity spectrum is measured from -50°C to 200°C. When the adhesive tape has a base material, the base material is removed, and the measurement is performed after preparing a sample of only the adhesive layer.
  • a dynamic viscoelasticity measuring device such as a viscoelasticity spectrometer (for example, DVA-200 manufactured by IT Keisoku Co., Ltd., or equivalent)
  • the measurement frequency is 1 Hz
  • the storage modulus at 100°C is measured when the dynamic viscoelasticity spectrum is measured from -50
  • the method for removing the substrate is not particularly limited as long as treatment using a solvent, treatment involving a chemical reaction, or treatment at high temperature is avoided in order to avoid denaturation of the pressure-sensitive adhesive layer.
  • a method of selecting an appropriate temperature and peeling speed, peeling off the substrate and the adhesive layer and removing the substrate, or a method of removing the substrate include a method of physically grinding the material.
  • the pressure-sensitive adhesive layer has a breaking elongation (hereinafter simply referred to as breaking elongation) of 800% or more at 25° C. measured at a tensile speed of 300 mm/min using a tensile tester.
  • breaking elongation hereinafter simply referred to as breaking elongation
  • the elongation at break of the pressure-sensitive adhesive layer is preferably 900% or more, more preferably 1000% or more.
  • the upper limit of the breaking elongation of the pressure-sensitive adhesive layer is not particularly limited, and the higher the elongation, the better.
  • the breaking elongation of the pressure-sensitive adhesive layer includes the monomer species and polymerization ratio constituting the pressure-sensitive adhesive constituting the pressure-sensitive adhesive layer, the molecular weight of the pressure-sensitive adhesive, the gel fraction, the presence or absence of the tackifying resin, and the type and content of the tackifying resin. , can be adjusted by the tape thickness.
  • the breaking elongation of the pressure-sensitive adhesive layer was measured using a tensile tester (e.g., Shimadzu's tensile Using a testing machine AG-IS, Orientec RTC-1310A, etc.), the distance between jigs was set to 10 mm, and the adhesive layer alone was pulled at 25 ° C.
  • the method for removing the substrate is not particularly limited as long as treatment using a solvent, treatment involving a chemical reaction, or treatment at high temperature is avoided in order to avoid denaturation of the pressure-sensitive adhesive layer.
  • a method of selecting an appropriate temperature and peeling speed, peeling off the substrate and the adhesive layer and removing the substrate, or a method of removing the substrate include a method of physically grinding the material.
  • the pressure-sensitive adhesive layer preferably has a loss tangent (tan ⁇ , hereinafter simply referred to as loss tangent) at 100°C measured at a measurement frequency of 1 Hz using a dynamic viscoelasticity measuring device of 0.01 or more and 0.5 or less. .
  • loss tangent loss tangent
  • the loss tangent of the pressure-sensitive adhesive layer is more preferably 0.05 or more, still more preferably 0.10 or more, more preferably 0.40 or less, and 0.30 or less. More preferred.
  • the loss tangent of the pressure-sensitive adhesive layer can be obtained by performing dynamic viscoelasticity measurement under the same conditions as for the shear storage modulus.
  • the pressure-sensitive adhesive layer preferably has a gel fraction of less than 50%.
  • the gel fraction of the pressure-sensitive adhesive layer is less than 50%, that is, the cross-linking ratio of the pressure-sensitive adhesive is low, the pressure-sensitive adhesive molecules can be easily stretched, so that the pressure-sensitive adhesive strength can be further increased, and the breakage The elongation can be easily adjusted within the above range.
  • the gel fraction of the pressure-sensitive adhesive layer is more preferably 30% or less, even more preferably 15% or less.
  • the lower limit of the gel fraction of the pressure-sensitive adhesive layer is not particularly limited, it is, for example, 0%.
  • the thickness of the pressure-sensitive adhesive layer is not particularly limited, but is preferably 5 ⁇ m or more, more preferably 10 ⁇ m or more, still more preferably 15 ⁇ m or more, preferably 200 ⁇ m or less, and 150 ⁇ m or less. is more preferable, and 100 ⁇ m or less is even more preferable. When the thickness of the pressure-sensitive adhesive layer is within this range, the pressure-sensitive adhesive tape can have excellent adhesive strength, holding power, and handleability.
  • the pressure-sensitive adhesive layer is not particularly limited as long as it satisfies the shear storage modulus and the breaking elongation. It is preferable to contain an acrylic copolymer (hereinafter referred to as an acrylic copolymer) having a structure derived from an olefin polymer having a saturated double bond.
  • the acrylic copolymer is preferably the main component in the polymer component (that is, the component contained in more than 50% by weight of the polymer component).
  • the above acrylic copolymer has a structure in which olefinic polymer sites are aggregated by interaction to form pseudo-crosslinking points.
  • the acrylic copolymer exhibits a property of being hard like a cross-linked pressure-sensitive adhesive when the strain is small and having a high holding power.
  • the pseudo cross-linking points are broken and the molecules of the acrylic copolymer are elongated, so that the pressure-sensitive adhesive exhibits a property of high flexibility. That is, by using the acrylic copolymer as the adhesive that constitutes the adhesive layer, it is possible to easily satisfy the shear storage modulus and the breaking elongation.
  • (meth)acrylic acid refers to acrylic acid or methacrylic acid.
  • the (meth)acrylic acid alkyl ester is not particularly limited, and examples thereof include an acrylate alkyl ester having a linear or branched alkyl group having 1 to 24 carbon atoms. Specifically, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, s-butyl (meth) acrylate, t-butyl (meth) acrylate, isobutyl (meth) acrylate, n-pentyl (meth) acrylate, isopentyl (meth) acrylate, n-hexyl (meth) acrylate, ishexyl (meth) acrylate, isoheptyl (meth) acrylate, n-heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth)acrylate, isooc
  • acrylic acid alkyl esters are selected in consideration of the type of olefinic polymer having a polymerizable unsaturated double bond at the end, which is the raw material of the acrylic copolymer, other monomers, and the additives to be blended. It is appropriately selected so as to satisfy the shear storage modulus and the elongation at break.
  • the glass transition temperature decreases as the number of carbon atoms increases, and when the number of carbon atoms in the alkyl group is 9 or more, the glass transition temperature increases as the number of carbon atoms increases.
  • alkyl acrylates having an alkyl group having 4 to 8 carbon atoms are preferable, and butyl acrylate is more preferable, because they easily satisfy the above shear storage modulus and breaking elongation.
  • These (meth)acrylic acid alkyl esters may be used alone, or two or more of them may be used in combination.
  • the acrylic copolymer preferably contains 50% by weight or more and 95% by weight or less of the structure derived from the (meth)acrylic acid alkyl ester.
  • the content of the structure derived from the (meth)acrylic acid alkyl ester in the acrylic copolymer is more preferably 60% by weight or more, still more preferably 70% by weight or more, and 90% by weight or less. is more preferably 85% by weight or less.
  • the olefinic polymer having a polymerizable unsaturated double bond at one end may have a polymerizable unsaturated double bond at one end, or may have a polymerizable unsaturated double bond at both ends.
  • an olefinic polymer having a polymerizable unsaturated double bond at one end is preferable because chemical cross-linking in the molecule hardly occurs.
  • the polymerizable unsaturated double bond include a (meth)acryloyl group, a vinyl ether group, and a styryl group.
  • a (meth)acryloyl group is preferred because of its excellent copolymerizability with (meth)acrylic acid alkyl esters.
  • the olefin polymer examples include ethylene-butylene copolymers, ethylene-propylene copolymers, ethylene polymers, propylene polymers, and butylene polymers.
  • Specific examples of the olefinic polymer having a polymerizable unsaturated double bond at one end include an ethylene macromonomer having a (meth)acryloyl group at one end and a propylene macromonomer having a (meth)acryloyl group at one end.
  • Examples include monomers, ethylene-butylene macromonomers having a (meth)acryloyl group at one end, and ethylene-propylene macromonomers having a (meth)acryloyl group at one end.
  • an ethylene-butylene macromonomer having a (meth)acryloyl group at one end and an ethylene-propylene macromonomer having a (meth)acryloyl group at one end are preferable because they easily satisfy the glass transition temperature described later.
  • These olefinic polymers having polymerizable unsaturated double bonds at their terminals may be used alone, or two or more of them may be used in combination.
  • the macromonomer here refers to a monomer having a polymerizable functional group with a weight average molecular weight of about 1,000 to 100,000.
  • the acrylic copolymer preferably contains 5% by weight or more and 30% by weight or less of a structure derived from an olefinic polymer having a polymerizable unsaturated double bond at the terminal.
  • a structure derived from an olefinic polymer having a polymerizable unsaturated double bond at the terminal in the acrylic copolymer is 5% by weight or more, a moderate number of pseudo-crosslinking points are formed. It is possible to make it easier to satisfy the range of the shear storage modulus. Further, when the content of the structure derived from the olefinic polymer having a polymerizable unsaturated double bond at the terminal is 30% by weight or less, cohesive failure can be further suppressed.
  • the content of the structure derived from the olefin polymer having a polymerizable unsaturated double bond at the terminal in the acrylic copolymer is more preferably 8% by weight or more, and more preferably 10% by weight or more. is more preferably 27% by weight or less, and even more preferably 25% by weight or less.
  • the content of structures derived from monomers containing two or more polymerizable unsaturated double bonds is preferably 0.1% by weight or less.
  • the olefinic polymer site of the acrylic copolymer forms a pseudo-crosslinking point, so that when the strain is small, it exhibits properties like a pressure-sensitive adhesive having a crosslinked structure. increases, the pseudo cross-linking points are cut off and the adhesive exhibits a property like that of a pressure-sensitive adhesive without a cross-linked structure.
  • the acrylic copolymer molecule can be converted when the strain increases. It can be made easier to stretch, and the adhesive strength can be further improved. More preferably, the content of the structure derived from the monomer containing two or more polymerizable unsaturated double bonds is 0%.
  • the acrylic copolymer preferably has a structure derived from a polar group-containing monomer.
  • the polar groups interact with each other, so that the adhesion and holding power can be increased.
  • the polar group-containing monomer include unsaturated monomonomers such as (meth)acrylic acid, (meth)acryloylacetic acid, (meth)acryloylpropionic acid, (meth)acryloylbutyric acid, (meth)acryloylpentanoic acid, and crotonic acid.
  • Carboxylic acid maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, N-vinyl-2-pyrrolidone, (meth)acryloylmorpholine, (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N- Isopropyl (meth)acrylamide, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate and the like can be mentioned.
  • the polar group-containing monomer preferably has a carboxyl group because it can further increase adhesive strength and holding power. These polar group-containing monomers may be used alone, or two or more of them may be used in combination.
  • the acrylic copolymer preferably contains 0.1% by weight or more and 10% by weight or less of the structure derived from the polar group-containing monomer.
  • the content of the structure derived from the polar group-containing monomer in the acrylic copolymer is 0.1% by weight or more, the interaction between the polar groups can be further enhanced. With this, the acrylic copolymer does not become too hard and the adhesion can be further increased.
  • the content of the structure derived from the polar group-containing monomer in the acrylic copolymer is more preferably 1% by weight or more, still more preferably 3% by weight or more, and 8% by weight or less. is more preferable, and 6% by weight or less is even more preferable.
  • the above acrylic copolymer preferably has a glass transition temperature in the range of -100 to 200°C when measured by differential scanning calorimetry, and all the glass transition temperatures are -20°C or lower.
  • the acrylic copolymer has a glass transition temperature in the above temperature range, and all the glass transition temperatures are ⁇ 20° C. or lower, that is, the acrylic copolymer has a high glass transition temperature. By not containing, the molecules of the acrylic copolymer can be easily stretched, so that the adhesive strength can be further increased.
  • the glass transition temperature is preferably ⁇ 30° C. or lower, more preferably ⁇ 35° C. or lower.
  • the above glass transition temperature can be adjusted by the kind of the monomer that is the material of the acrylic copolymer.
  • the glass transition temperature is measured in accordance with JIS K6240:2011 using a differential scanning calorimeter (e.g., 220C manufactured by Seiko Instruments Inc.) under a nitrogen atmosphere (nitrogen flow, flow rate 50 mL/min). It can be obtained by measuring at a temperature of -100 to 200°C and a heating rate of 10°C/min.
  • a differential scanning calorimeter e.g., 220C manufactured by Seiko Instruments Inc.
  • the acrylic copolymer preferably has a weight average molecular weight of 200,000 or more and 2,000,000 or less.
  • the weight average molecular weight of the acrylic copolymer is more preferably 500,000 or more, and more preferably 1,500,000 or less.
  • the weight-average molecular weight can be determined, for example, by the GPC method using a polystyrene standard.
  • the acrylic copolymer preferably has a molecular weight distribution (Mw/Mn) of 1.0 or more and 6.0 or less. When the molecular weight distribution of the acrylic copolymer is within the above range, the shear storage modulus and the breaking elongation can be easily satisfied.
  • the molecular weight distribution of the acrylic copolymer is more preferably 1.5 or more, and more preferably 4.5 or less.
  • the pressure-sensitive adhesive layer preferably contains a high hydroxyl value tackifying resin having a hydroxyl value of 15 mgKOH/g or more. Since the tackifying resin having a hydroxyl value within the above range has a high polarity, it is difficult to be compatible with the olefinic polymer moiety having a low polarity. As a result, the adhesive force can be further improved without inhibiting the formation of pseudo-crosslinking points due to the interaction of the olefinic polymer sites with low polarity.
  • the hydroxyl value of the high hydroxyl value tackifying resin is more preferably 30 mgKOH/g or more, preferably 200 mgKOH/g or less, and more preferably 150 mgKOH/g or less. Examples of the high hydroxyl value tackifier resin include terpene phenol resins and polymerized rosin ester resins.
  • the pressure-sensitive adhesive layer preferably contains 1 part by weight or more and 40 parts by weight or less of the high hydroxyl value tackifying resin with respect to 100 parts by weight of the acrylic copolymer.
  • the content of the high hydroxyl value tackifying resin is more preferably 20 parts by weight or more, and more preferably 35 parts by weight or less.
  • the content of the low hydroxyl value tackifying resin having a hydroxyl value of less than 15 mgKOH/g is preferably 5 parts by weight or less per 100 parts by weight of the acrylic copolymer. Since the tackifying resin having a hydroxyl value of less than 15 mgKOH/g has low polarity, it is easily compatible with the constituent units derived from the olefin polymer. With the above content, it is possible to suppress the inhibition of the formation of pseudo cross-linking points due to interactions between the olefinic polymer moieties. As a result, it is possible to obtain an adhesive tape having excellent holding power. More preferably, the content of the low hydroxyl value tackifying resin having a hydroxyl value of less than 15 mgKOH/g is 0 parts by weight with respect to 100 parts by weight of the acrylic copolymer.
  • the low hydroxyl value tackifying resin As described above, from the viewpoint of increasing the holding power, it is preferable to use the low hydroxyl value tackifying resin as little as possible. However, from the viewpoint of further improving the initial adhesive strength, the content of the low hydroxyl value tackifying resin having a hydroxyl value of less than 15 mgKOH/g in the pressure-sensitive adhesive layer per 100 parts by weight of the acrylic copolymer It is preferably 5 parts by weight or more and 70 parts by weight or less, and more preferably used in combination with the high hydroxyl value tackifying resin. Although the reason why the initial adhesive strength is improved by using the low hydroxyl value tackifying resin is not completely clear, it is thought to be due to the following mechanism.
  • the tackifier resin having a hydroxyl value of less than 15 mgKOH/g has low polarity, it is easily compatible with the structural unit derived from the olefin polymer. Therefore, it is thought that the low hydroxyl value tackifying resin is compatible with the pseudo cross-linking points, thereby moderately softening the pseudo cross-linking points and improving the adhesive strength.
  • the decrease in holding power can be reduced by using the high hydroxyl value tackifying resin in combination, and the initial adhesive strength can be improved while holding. Power can also be secured.
  • the content of the low hydroxyl value tackifying resin is more preferably more than 5 parts by weight, more preferably 60 parts by weight or less, still more preferably 10 parts by weight or more, and 50 parts by weight or less. is more preferably 20 parts by weight or more, even more preferably 30 parts by weight or more, and even more preferably 40 parts by weight or more.
  • Examples of the low hydroxyl value tackifying resin include terpene resins and petroleum resins.
  • the pressure-sensitive adhesive layer may contain conventionally known fine particles and additives such as inorganic fine particles, conductive fine particles, antioxidants, foaming agents, organic fillers and inorganic fillers, if necessary.
  • the acrylic copolymer By using the acrylic copolymer, the tackifying resin, and the additive described above, it is possible to easily form a pressure-sensitive adhesive layer that satisfies the shear storage modulus at 100°C and the breaking elongation at 25°C.
  • Such an acrylic copolymer having a structure derived from a (meth)acrylic acid alkyl ester and a structure derived from an olefinic polymer having a polymerizable unsaturated double bond at the terminal, and the acrylic The system copolymer has a glass transition temperature in the range of -100 to 200 ° C. when differential scanning calorimetry is performed, and all the glass transition temperatures are -20 ° C. or lower. It is one of the present invention.
  • the same acrylic copolymer, tackifying resin and additives as those used in the above-described pressure-sensitive adhesive layer can be used.
  • the pressure-sensitive adhesive tape of the present invention and the pressure-sensitive adhesive tape having a pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition of the present invention are measured using a dynamic viscoelasticity measuring device by shearing the pressure-sensitive adhesive layer at a measurement frequency of 1 Hz.
  • loss tangent preferably has a peak at 40 degrees or less.
  • the pressure-sensitive adhesive layer more preferably has a loss tangent peak at 35° C. or lower, and more preferably at 25° C. or lower.
  • the temperature of the peak of the loss tangent can be adjusted by the kind and copolymerization ratio of the monomers constituting the acrylic copolymer, additives, and the like.
  • the loss tangent is -100 under the conditions of 5° C./min and 1 Hz in the low-speed heating shear deformation mode using a viscoelastic spectrometer (manufactured by IT Keisoku Co., Ltd., DVA-200, or equivalent). It can be obtained by measuring dynamic viscoelasticity spectrum from °C to 200 °C.
  • the pressure-sensitive adhesive tape of the present invention may be a non-support type having no base material, or a support type pressure-sensitive adhesive layer formed on a base material.
  • the pressure-sensitive adhesive tape of the present invention preferably has a base material, and has a pressure-sensitive adhesive layer on at least one surface of the base material, since it has excellent reworkability. It is more preferable to have
  • the base material is not particularly limited. Examples include an opened sheet.
  • the thickness of the substrate is not particularly limited, it is preferably 5 ⁇ m or more and 200 ⁇ m or less. When the thickness of the base material is within this range, the pressure-sensitive adhesive tape can have appropriate stiffness and be excellent in handleability. More preferably, the thickness of the substrate is 10 ⁇ m or more and 150 ⁇ m or less.
  • the method for producing the pressure-sensitive adhesive tape of the present invention is not particularly limited, and conventionally known methods can be used.
  • the alkyl (meth)acrylate, the olefinic polymer having a polymerizable unsaturated double bond at the terminal, and optionally other monomers are copolymerized in a conventional manner to obtain an acrylic copolymer.
  • the obtained acrylic copolymer, and if necessary, a tackifying resin and a pressure-sensitive adhesive solution containing other additives are applied on a film that has been subjected to a mold release treatment, and can be produced by drying.
  • the pressure-sensitive adhesive tape produced by the above method can be used as a pressure-sensitive adhesive layer, and a support-type pressure-sensitive adhesive tape can be obtained by laminating the pressure-sensitive adhesive layer to a base material.
  • the adhesive composition used for the adhesive tape and this adhesive tape which are compatible with the outstanding adhesive force and holding power can be provided.
  • the resulting acrylic copolymer 1 was measured using a differential scanning calorimeter (220C, manufactured by Seiko Instruments Inc.) under a nitrogen atmosphere (nitrogen flow, flow rate 50 mL/min) by a method in accordance with JIS K6240:2011.
  • the glass transition temperature was measured under conditions of a temperature of -100 to 200°C and a heating rate of 10°C/min.
  • the weight average molecular weight and molecular weight distribution were measured using 2690 Separations Module (manufactured by Waters) as a measuring instrument, GPC KF-806L (manufactured by Showa Denko) as a column, ethyl acetate as a solvent, a sample flow rate of 1 mL/min, and column temperature. Measurement was performed at 40°C.
  • Ethylene-butylene macromonomer olefin polymer having a methacryloyl group at one end, manufactured by Kraton Polymer Japan, HPVM-L1253, weight average molecular weight 7000, glass transition temperature -68°C Methyl methacrylate macromonomer: acrylic polymer having a methacryloyl group at one end, manufactured by Toagosei Co., Ltd., AA-6, weight average molecular weight 11600, glass transition temperature 100°C
  • Ethylene glycol macromonomer Oxyalkylene polymer having a methacryloyl group at one end, manufactured by NOF Corporation, PME-4000, weight average molecular weight 4000, glass transition temperature -65°C
  • Example 1 An adhesive solution was obtained by adding 30 parts by weight of YS Polyster G150 as a tackifying resin to 100 parts by weight of the solid content of the ethyl acetate solution of acrylic copolymer 1 and mixing. The resulting pressure-sensitive adhesive solution was applied with a doctor knife to a dry film thickness of 40 ⁇ m on the release-treated surface of a 50 ⁇ m polyethylene terephthalate (PET) film that had been subjected to a release treatment on one side. The pressure-sensitive adhesive tape was obtained by drying the coating solution by heating at °C for 5 minutes.
  • the details of the tackifying resin are as follows.
  • YS Polyster G150 terpene phenolic resin, manufactured by Yasuhara Chemical Co., Ltd., hydroxyl value 140 mgKOH/g
  • Examples 2 to 28, Comparative Examples 1 to 4 An adhesive tape was obtained in the same manner as in Example 1, except that the formulation of the adhesive solution was as shown in Tables 3 and 4.
  • the details of the tackifying resin and the cross-linking agent are as follows.
  • YS Polyster U115 Terpene phenolic resin, manufactured by Yasuhara Chemical Co., Ltd., hydroxyl value 20 mgKOH/g YS Polystar K125: terpene phenolic resin, manufactured by Yasuhara Chemical Co., Ltd., hydroxyl value 200 mgKOH/g Alcon P140: Hydrogenated petroleum resin, manufactured by Arakawa Chemical Co., Ltd., hydroxyl value 0 mgKOH/g YS resin PX800: terpene resin, manufactured by Yasuhara Chemical Co., hydroxyl value 0 mgKOH/g Coronate L-45: isocyanate cross-linking agent, manufactured by Tosoh Corporation
  • test piece was prepared by cutting the adhesive tape into a width of 25 mm. Next, the obtained test piece was attached to a SUS plate and pressure-bonded by reciprocating once with a 1 kg rubber roller to prepare a measurement sample. After that, it was cured at 23° C. for 24 hours, and the obtained measurement sample was subjected to a 180° peel test at a tensile speed of 300 mm/min according to JIS Z 0237:2009, and the adhesive strength (N/25 mm) at 23° C. was measured. , the adhesive strength was evaluated according to the following criteria.
  • the holding force of the obtained pressure-sensitive adhesive tape was measured by the following method using the shear creep measuring device (manufactured by Asahi Seiko Co., Ltd., NST1) shown in FIG. First, the release film on one side of the obtained adhesive tape was peeled off, and a corona-treated polyethylene terephthalate (PET) film was attached to the exposed adhesive layer, and then cut into a piece of 1 cm wide by 12 cm long. A test piece 5 was obtained.
  • the temperature controller 4 of the apparatus was set to 60° C. and left until the set temperature was stabilized. In addition, the temperature controller 4 was used in combination with the following.
  • Temperature controller SA100 model: SA100FK08-MN-4 NN-NN, copper water-cooled Peltier unit manufactured by Takagi Seisakusho Co., Ltd., model: PU-50W, EYELA cooling water circulation device manufactured by Takagi Seisakusho Co., Ltd. Cool Ace, model: CCA1111 type, Tokyo Rika Kikai manufactured by the company
  • the other release film of the test piece 5 is peeled off from the end by about 3 cm and removed, and the exposed adhesive layer is applied to the adherend 3 (JIS Z 0237 stainless steel) so that the adhesion area is 1 cm ⁇ 1 cm. pasted.
  • adherend 3 JIS Z 0237 stainless steel
  • a quartz block 2 quartz glass coated with chromium
  • a test piece 5 was attached to a wire connecting a weight 6 of 50 g. It was left in this state and kept at constant temperature for 5 minutes.
  • the PC connected to the apparatus was operated to start applying a load, and a shear load was applied to the test piece 5 in the waterside direction for 3 minutes.
  • the amount of displacement due to the deformation of the adhesive is detected as the amount of movement of the mirror-finished quartz block 2 on the test piece using a laser interferometer 1 (SI-F10, manufactured by Keyence Corporation), and the holding force is evaluated according to the following criteria. did. ⁇ : 10 ⁇ m or less ⁇ : greater than 10 ⁇ m and 50 ⁇ m or less ⁇ : greater than 50 ⁇ m and 100 ⁇ m or less ⁇ : greater than 100 ⁇ m
  • the adhesive composition used for the adhesive tape and this adhesive tape which are compatible with the outstanding adhesive force and holding power can be provided.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)
PCT/JP2022/019073 2021-04-30 2022-04-27 粘着テープ及び粘着剤組成物 Ceased WO2022230936A1 (ja)

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EP22795849.3A EP4332193A4 (en) 2021-04-30 2022-04-27 Adhesive tape and adhesive composition
US18/288,426 US20240209240A1 (en) 2021-04-30 2022-04-27 Adhesive tape and adhesive composition
CN202280007505.3A CN116529336A (zh) 2021-04-30 2022-04-27 粘合带及粘合剂组合物
KR1020237013288A KR20240004209A (ko) 2021-04-30 2022-04-27 점착 테이프 및 점착제 조성물
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WO2023145567A1 (ja) * 2022-01-26 2023-08-03 積水化学工業株式会社 粘着テープ
WO2025028645A1 (ja) * 2023-08-02 2025-02-06 積水化学工業株式会社 粘着剤、粘着テープ、ポリオレフィン樹脂成型体、複合構成体、自動車部材、及び、ポリオレフィン樹脂成型体の製造方法
WO2025173519A1 (ja) * 2024-02-14 2025-08-21 株式会社巴川コーポレーション 粘着シート及びそれを用いた積層体

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KR20220103046A (ko) * 2021-01-14 2022-07-21 신꼬오덴기 고교 가부시키가이샤 기판 고정 장치

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WO2025028645A1 (ja) * 2023-08-02 2025-02-06 積水化学工業株式会社 粘着剤、粘着テープ、ポリオレフィン樹脂成型体、複合構成体、自動車部材、及び、ポリオレフィン樹脂成型体の製造方法
WO2025173519A1 (ja) * 2024-02-14 2025-08-21 株式会社巴川コーポレーション 粘着シート及びそれを用いた積層体

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