WO2020262309A1 - 粘着剤組成物および粘着性加工品 - Google Patents

粘着剤組成物および粘着性加工品 Download PDF

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WO2020262309A1
WO2020262309A1 PCT/JP2020/024429 JP2020024429W WO2020262309A1 WO 2020262309 A1 WO2020262309 A1 WO 2020262309A1 JP 2020024429 W JP2020024429 W JP 2020024429W WO 2020262309 A1 WO2020262309 A1 WO 2020262309A1
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French (fr)
Japanese (ja)
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庸祐 ▲高▼橋
幸治 松永
浩貴 金谷
邦昭 川辺
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三井化学株式会社
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Priority to CN202080046386.3A priority Critical patent/CN114026194B/zh
Priority to JP2021526976A priority patent/JP7235863B2/ja
Priority to KR1020217039719A priority patent/KR102565500B1/ko
Publication of WO2020262309A1 publication Critical patent/WO2020262309A1/ja

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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
    • 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
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • 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
    • C09J133/062—Copolymers with monomers not covered by C09J133/06
    • C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • C09J125/00—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 an aromatic carbocyclic ring; Adhesives based on derivatives of such polymers
    • C09J125/02—Homopolymers or copolymers of hydrocarbons
    • 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
    • C09J125/00—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 an aromatic carbocyclic ring; Adhesives based on derivatives of such polymers
    • C09J125/02—Homopolymers or copolymers of hydrocarbons
    • C09J125/16—Homopolymers or copolymers of alkyl-substituted styrenes
    • 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
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • C09J7/25—Plastics; Metallised plastics based on macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/255—Polyesters
    • 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
    • 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]
    • 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
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F3/00—Labels, tag tickets, or similar identification or indication means; Seals; Postage or like stamps
    • G09F3/08—Fastening or securing by means not forming part of the material of the label itself
    • G09F3/10—Fastening or securing by means not forming part of the material of the label itself by an 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/10—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet
    • C09J2301/12—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers
    • C09J2301/122—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers the adhesive layer being present only on one side of the carrier, e.g. single-sided adhesive tape
    • 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
    • C09J2467/00—Presence of polyester
    • C09J2467/006—Presence of polyester in the substrate

Definitions

  • the present invention relates to an adhesive composition and an adhesive processed product.
  • Adhesives also called pressure-sensitive adhesives
  • Adhesives are easy to use and have adhesiveness to various objects such as plastics, papers, metals, and glass, so tapes, labels, sheets, double-sided tapes, etc. It is used as an adhesive layer in the adhesive processed products of.
  • a composition using an acrylic resin or a styrene resin (styrene-based block copolymer or the like) as a base polymer is generally used as the composition using an acrylic resin or a styrene resin (styrene-based block copolymer or the like) as a base polymer is generally used.
  • an adhesive composition using an acrylic resin as a base polymer has excellent transparency and also has excellent adhesiveness to polar adherends such as paper, metal, and glass.
  • the pressure-sensitive adhesive composition has more sufficient stickiness and adhesiveness even when a thinner pressure-sensitive adhesive layer is formed.
  • a method has been proposed in which a tackifier resin such as a rosin resin, a terpene resin, and a petroleum resin is added to the acrylic pressure-sensitive adhesive composition to further enhance the stickiness of the pressure-sensitive adhesive composition.
  • a tackifier resin such as a rosin resin, a terpene resin, and a petroleum resin
  • Patent Document 1 by adding a tackifier resin having low compatibility with a (meth) acrylic polymer, such as a rosin resin, to an acrylic pressure-sensitive adhesive composition, both normal temperature and high temperature adhesive strength can be obtained. It is stated that it can be exerted.
  • Patent Document 1 describes that the tackifier resin is added so that the haze value when the pressure-sensitive adhesive composition is formed into a film is 15 to 95%.
  • Patent Document 1 describes that the adhesiveness of the pressure-sensitive adhesive composition can be further enhanced by adding a pressure-sensitive adhesive resin such as the rosin-based resin. However, as described in Patent Document 1, when the pressure-sensitive adhesive resin is added, the transparency of the pressure-sensitive adhesive composition is lowered.
  • a pressure-sensitive adhesive resin such as the rosin-based resin
  • the present invention has been made in view of the above circumstances, and a pressure-sensitive adhesive composition capable of obtaining a thin-film pressure-sensitive adhesive layer having sufficient adhesiveness and high transparency, and the adhesive composition.
  • the purpose is to provide a processed adhesive processed product.
  • the present invention relates to the following [1] to [6].
  • the total content is 100 parts by mass.
  • the (meth) acrylic resin (A) satisfies the following (A-1) and (A-2), and The (co) polymer (B) satisfies all of the following (B-1) to (B-5).
  • Adhesive composition (A-1) Contains a structural unit derived from a (meth) acrylate having an alkyl group having 1 or more and 12 or less carbon atoms, and a structural unit derived from a (meth) acrylate containing a hydroxyl group.
  • A-2) The glass transition temperature (Tg) measured by a differential scanning calorimeter (DSC) is in the range of ⁇ 80 ° C. or higher and 0 ° C. or lower.
  • (B-1) Contains 20 mol% or more of structural units derived from isopropenyl toluene based on the total amount of the structural units.
  • (B-2) The softening point measured according to JIS K2207 is in the range of 90 ° C. or higher and 130 ° C. or lower.
  • (B-3) The glass transition temperature (Tg) measured by a differential scanning calorimeter (DSC) is in the range of 40 ° C. or higher and 80 ° C. or lower.
  • (B-4) The content of the compound having a molecular weight of 400 or less in terms of polystyrene measured by gel permeation chromatography (GPC) is 10% by mass or less.
  • the polystyrene-equivalent number average molecular weight (Mn) measured by gel permeation chromatography (GPC) is in the range of 750 or more and 1000 or less, and the z average molecular weight (Mz) is in the range of 1200 or more and 2000 or less.
  • the dispersity (Mw / Mn), which is the ratio of the weight average molecular weight (Mw) to the number average molecular weight (Mn), is 1.5 or less.
  • (B-6) Consists of styrene, ⁇ -methylstyrene, inden, vinyltoluene and unsaturated aliphatic hydrocarbon compound having 4 or 5 carbon atoms in an amount of 1 mol% or more and 80 mol% or less based on the total amount of the structural unit. Contains structural units derived from monomers selected from the group.
  • An adhesive processed product obtained by processing the adhesive composition according to [1] or [2], which is a tape, label, sheet or double-sided tape.
  • the adhesive processed product according to [3] which has an adhesive layer having a thickness of 5 ⁇ m or more and 50 ⁇ m or less.
  • an adhesive composition capable of obtaining a thin film-like adhesive layer having sufficient adhesiveness and high transparency, and an adhesive processed product obtained by processing the adhesive composition. Provided.
  • FIG. 1 is a graph showing the relationship between the total light transmittance and the adhesive force when the film thickness of the adhesive layer is 10 ⁇ m in Example 1 and Comparative Examples 1 to 3.
  • One embodiment of the present invention relates to an adhesive composition containing a (meth) acrylic resin (A), a (co) polymer (B), and a cross-linking agent (C).
  • (meth) acrylic means “acrylic or methacrylic”
  • (meth) acrylate means “acrylate or methacrylate”
  • (co) polymer means "monopolymer or copolymer”. It means "polymer”.
  • the (meth) acrylic resin (A) is a (co) polymer of an acrylic monomer or a methacrylic monomer.
  • the (meth) acrylic resin (A) satisfies the following requirements (A-1) and (A-2).
  • (A-1) Contains a structural unit derived from a (meth) acrylate having an alkyl group having 1 or more and 12 or less carbon atoms, and a structural unit derived from a (meth) acrylate containing a hydroxyl group.
  • (A-2) The glass transition temperature (Tg) measured by a differential scanning calorimeter (DSC) is in the range of ⁇ 80 ° C. or higher and 0 ° C. or lower.
  • Requirement (A-1) is a requirement for enhancing the adhesiveness of the adhesive composition according to the present embodiment.
  • the glass of the (meth) acrylic resin (A) contains a structural unit derived from (meth) acrylate having an alkyl group having 1 or more and 12 or less carbon atoms, the glass of the (meth) acrylic resin (A) The transition temperature (Tg) is increased, and the adhesiveness of the adhesive composition is further increased.
  • the (meth) acrylate having an alkyl group having 1 or more and 12 or less carbon atoms is preferably a (meth) acrylate having an alkyl group having 1 or more and 10 or less carbon atoms, and has 2 carbon atoms.
  • a (meth) acrylate having an alkyl group of 8 or more is more preferable.
  • the alkyl group may be linear or may have a branch.
  • Examples of the (meth) acrylate having an alkyl group having 1 or more and 12 or less carbon atoms include methyl (meth) acrylic acid, ethyl (meth) acrylic acid, n-propyl (meth) acrylic acid, and (meth) acrylic acid.
  • Isopropyl, n-butyl (meth) acrylate, isobutyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, (meth) acrylic Includes isooctyl acid acid, 2-ethylhexyl (meth) acrylate, and decyl (meth) acrylate, and lauryl (meth) acrylate.
  • the (meth) acrylic resin (A) contains 50 mol% or more and 99 mol of the structural unit derived from the (meth) acrylate having an alkyl group having 1 or more and 12 or less carbon atoms with respect to the total amount of the structural unit. % Or less, more preferably 55 mol% or more and 95 mol% or less, and even more preferably 60 mol% or more and 90 mol% or less.
  • the (meth) acrylic resin (A) contains a structural unit derived from the (meth) acrylate containing a hydroxyl group
  • the number of cross-linking points by the cross-linking agent (C) increases, so that the cross-linking density of the adhesive composition increases. It becomes easy to increase the molecular weight.
  • Such an adhesive composition does not easily follow the surface of the adherend even when crimped, and the adhesiveness does not easily decrease during crimping.
  • Examples of the (meth) acrylate containing a hydroxyl group include hydroxyethyl (meth) acrylate, hydroxypropul (meth) acrylate, and N-methylol (meth) acrylamide. Of these, from the above viewpoint, the (meth) acrylate containing the hydroxyl group is preferably hydroxyethyl (meth) acrylate.
  • the content of the structural unit derived from the (meth) acrylate containing the hydroxyl group of the (meth) acrylic resin (A) is 0.1 mol% or more and 5 mol% or less with respect to the total amount of the structural unit. It is more preferably 0.2 mol% or more and 3 mol% or less, and further preferably 0.3 mol% or more and 2 mol% or less.
  • the (meth) acrylic resin (A) has a functional group capable of forming a crosslink, which is different from the (meth) acrylate having an alkyl group having 1 or more and 12 or less carbon atoms or the (meth) acrylate containing a hydroxyl group. It may be a copolymer having a structural unit derived from the monomer (or oligomer) having. Examples of monomers having functional groups capable of forming the above crosslinks include (meth) acrylic acid, (meth) acrylamide and the like.
  • the (meth) acrylic resin (A) may be a copolymer having a structural unit derived from a vinyl-based monomer other than the above, if necessary.
  • vinyl-based monomers include styrene, vinyl acetate and the like.
  • the requirement (A-2) is a requirement for the adhesiveness of the adhesive composition according to the present embodiment to be suitably exhibited in a wider temperature range.
  • the (meth) acrylic resin (A) is a copolymer having a glass transition temperature (Tg) measured by a differential scanning calorimeter (DSC) in the range of ⁇ 80 ° C. or higher and 0 ° C. or lower.
  • the adhesive composition having a thin adhesive layer can exhibit adhesiveness in a wide temperature range.
  • the (meth) acrylic resin (A) preferably has a glass transition temperature (Tg) in the range of ⁇ 70 ° C. or higher and ⁇ 5 ° C. or lower, and preferably in the range of ⁇ 60 ° C. or higher and ⁇ 10 ° C. or lower. Is more preferable.
  • the glass transition temperature (Tg) of the (meth) acrylic resin (A) can be adjusted within the above range by changing the monomer to be polymerized and its ratio.
  • the (meth) acrylic resin (A) can be synthesized by a known polymerization method using a monomer (or oligomer) as a material for each of the above structural units.
  • the above-mentioned polymerization method is not particularly limited as long as it is a radical polymerization method including a bulk polymerization method, a solution polymerization method, a suspension polymerization method and the like.
  • the glass transition temperature (Tg) and other properties of the (meth) acrylic resin (A) can be easily controlled, and the (meth) acrylic resin (A) having the desired properties can be easily synthesized, and thus the solution weight. Legal is preferred.
  • a polymerization initiator may be used.
  • examples of the above polymerization initiators include dicumyl peroxide, benzoyl peroxide, t-butylperoxy-2-ethylhexanoate, 1,1-bis (t-butylperoxy) cyclohexane, ⁇ , ⁇ '-.
  • Azobisisobutyronitrile acetyl peroxide, t-butylperoxypivalate, t-butylhydroperoxide, cumenehydroperoxide, t-hexylperoxypivalate, 2,2'-azobis- (2,4) -Dimethylvaleronitrile), lauriloyl peroxide, t-butylperoxyneohexanoate, peroxide-di-t-butyl, azodicyclohexylcarbonitrile, ⁇ , ⁇ -azodiisobutyrate dimethyl, succinic acid peroxide, dikumen Peroxides, benzoyl peroxide and the like are included.
  • solvent used for the above solution polymerization examples include ethyl acetate, butyl acetate, benzene, toluene, xylene, cyclohexane, methyl ethyl ketone and the like.
  • the (co) polymer (B) is a (co) polymer different from the (meth) acrylic resin (A), and has a (co) weight that satisfies all of the following (B-1) to (B-5). It is a coalescence.
  • (B-1) Contains 20 mol% or more of structural units derived from isopropenyl toluene based on the total amount of the structural units.
  • (B-2) The softening point measured according to JIS K2207 is in the range of 90 ° C. or higher and 130 ° C. or lower.
  • (B-3) The glass transition temperature (Tg) measured by a differential scanning calorimeter (DSC) is in the range of 40 ° C. or higher and 80 ° C. or lower.
  • (B-4) The content of the compound having a molecular weight of 400 or less in terms of polystyrene measured by gel permeation chromatography (GPC) is 10% by mass or less.
  • the polystyrene-equivalent number average molecular weight (Mn) measured by gel permeation chromatography (GPC) is in the range of 750 or more and 1000 or less, and the z average molecular weight (Mz) is in the range of 1200 or more and 2000 or less.
  • Requirement (B-1) is a requirement for increasing the adhesiveness of the adhesive composition according to the present embodiment without reducing the transparency.
  • the (co) polymer (B) contains 20 mol% or more of isopropenyl toluene (o-isopropenyl toluene, m-isopropenyl toluene, p-iso) based on the total amount of its structural units.
  • isopropenyl toluene o-isopropenyl toluene, m-isopropenyl toluene, p-iso
  • the (meth) acrylic resin (A) and the (co) polymer (B) are easily compatible with each other, and the (co) polymer (B) is easily compatible. It is considered that this is because it becomes easy to be finely dispersed in the (meth) acrylic resin (A).
  • the (co) polymer (B) containing a structural unit derived from isopropenyl toluene has a solubility parameter (SP value) of 8.7 to 8.9 and an SP value (8.6 to 9) of the (meth) acrylic resin. Since the SP value difference from 1) is small, it is presumed that it is easily compatible with the (meth) acrylic resin (A).
  • the content of the structural unit derived from isopropenyl toluene of the (co) polymer (B) is preferably 50 mol% or more, more preferably 70 mol% or more, based on the total amount of the structural unit. , 85 mol% or more is more preferable.
  • the upper limit of the content of the structural unit derived from isopropenyl toluene is not particularly limited, it can be 100 mol% or less, preferably 98 mol% or less, and more preferably 96 mol% or less. , More preferably less than 95 mol%.
  • Requirement (B-2) is a requirement for making the viscosity of the adhesive composition according to the present embodiment excellent in coatability to a substrate.
  • the adhesive composition containing a solvent in particular Since it has an appropriate viscosity the adhesive composition can be more easily applied to the substrate.
  • the (co) polymer (B) preferably has a softening point in the range of 95 ° C. or higher and 125 ° C. or lower, more preferably 100 ° C. or higher and 120 ° C. or lower, and 105 ° C. or higher. It is more preferably in the range of 115 ° C. or lower.
  • the softening point of the (co) polymer (B) can be adjusted to the above range by adjusting the monomer species to be copolymerized, the molecular weight, and the molecular weight distribution.
  • Requirement (B-3) is a requirement for adjusting both transparency and adhesiveness to a suitable range while increasing the heat resistance of the adhesive composition according to the present embodiment.
  • the (co) polymer (B) preferably has a glass transition temperature (Tg) in the range of 45 ° C. or higher and 78 ° C. or lower, and more preferably 50 ° C. or higher and 75 ° C. or lower. , 55 ° C. or higher and 70 ° C. or lower is more preferable.
  • the glass transition temperature (Tg) of the (co) polymer (B) can be adjusted to the above range by adjusting the monomer species to be copolymerized, the molecular weight, and the molecular weight distribution.
  • the glass transition temperature (Tg) of the (co) polymer (B) can be calculated from the theoretically calculated value obtained by the above-mentioned FOX formula.
  • Requirement (B-4) is a requirement for further enhancing the adhesiveness and heat resistance of the adhesive composition according to the present embodiment.
  • the content of the compound having a polystyrene-equivalent molecular weight of 400 or less measured by gel permeation chromatography (GPC) of the (co) polymer (B) is 10% by mass or less, an extremely low molecular weight component Since the content of the adhesive is low, the heat resistance can be further enhanced while maintaining the adhesiveness of the adhesive composition.
  • the content of the compound having a molecular weight of 400 or less is preferably 8% by mass or less, and more preferably 6% by mass or less in the (co) polymer (B).
  • the lower limit of the content of the compound having a molecular weight of 400 or less is not particularly limited, it can be 0% by mass (measurement limit) or more.
  • the content of the compound having a molecular weight of 400 or less is between the curve having a molecular weight of 400 or less and the baseline in the integrated molecular weight distribution curve measured by the GPC method (gel permeation chromatography) using tetrahydrofuran as a solvent in terms of polystyrene. It can be measured by calculating the area of the region by integration.
  • the content of the compound having a molecular weight of 400 or less of the (co) polymer (B) can be adjusted to the above range by distilling the (co) polymer (B) under reduced pressure at a heating temperature of 250 ° C. or less.
  • the requirement (B-5) is a requirement for increasing the adhesiveness of the adhesive composition according to the present embodiment without reducing the transparency.
  • the (co) polymer (B) has a polystyrene-equivalent number average molecular weight (Mn) in the range of 750 or more and 1000 or less as measured by gel permeation chromatography (GPC), and has a z average molecular weight.
  • Mz is in the range of 1200 or more and 2000 or less
  • the dispersity (Mw / Mn) which is the ratio of the weight average molecular weight (Mw) to the number average molecular weight (Mn) is 1.5 or less. Since the (co) polymer (B) satisfying the requirement (B-5) has a relatively small molecular weight, it enhances the wettability of the adhesive composition to the substrate and enhances the adhesiveness of the adhesive composition.
  • the (co) polymer (B) satisfying the requirement (B-5) has a small variation in molecular weight, it is easily compatible with the (meth) acrylic resin (A), and the adhesive composition has higher transparency. Is presumed to be able to be obtained.
  • the (co) polymer (B) preferably has the number average molecular weight (Mn) of 770 or more and 980 or less, more preferably 790 or more and 950 or less, and 800 or more and 900 or less. Is even more preferable.
  • the (co) polymer (B) preferably has a z average molecular weight (Mz) of 1300 or more and 1900 or less, and more preferably 1400 or more and 1800 or less.
  • the (co) polymer (B) has a dispersity (Mw / Mn) of 1.45 or less, which is a ratio of the weight average molecular weight (Mw) to the number average molecular weight (Mn). It is preferably 1.4 or less, and more preferably 1.4 or less.
  • the lower limit of Mw / Mn is not particularly limited, but may be 1 or more.
  • Dispersity (Mw / Mn), which is the ratio of the number average molecular weight (Mn), z average molecular weight (Mz), and weight average molecular weight (Mw) to the number average molecular weight (Mn) of the (co) copolymer (B). Can be adjusted to the above range by copolymerizing the monomer species and distillation under reduced pressure.
  • the (co) polymer (B) is preferably a (co) polymer that further satisfies the following (B-6).
  • (B-6) Derived from a monomer selected from the group consisting of styrene, ⁇ -methylstyrene, inden, vinyltoluene and unsaturated aliphatic hydrocarbon compounds having 4 or 5 carbon atoms in an amount of 1 mol% or more and 80 mol% or less. Contains structural units.
  • the structural units derived from these monomers are (co) heavy while maintaining the transparency of the adhesive composition by increasing the compatibility of the (co) polymer (B) with the (meth) acrylic resin (A).
  • the molecular weight distribution (Mw / Mn) of the coalescence (B) can be easily adjusted to the above range.
  • the C 4 fraction and C 5 fraction, boiling range at normal pressure is fraction usually -15 ⁇ + 45 °C.
  • the C 4 and C 5 distillates are 1-butene, isobutene, 2-butene, 1,3-butadiene, 1-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-. It contains polymerizable monomers such as butene, isoprene, 1,3-pentadiene, and cyclopentadiene.
  • the C 4 fraction and C 5 fraction, light oil fraction containing gas fraction by-produced during atmospheric distillation (topping) of crude oil in refineries, by-product in petroleum cracking or reforming process Similar light oil fractions and petroleum fractions containing gas-containing light oil fractions obtained in petroleum naphtha decomposition at petroleum chemical plants may be used as they are, or may be distilled, extracted or otherwise processed. In addition, it may be used as a desired fraction.
  • the (co) polymer (B) is derived from styrene, ⁇ -methylstyrene, inden, vinyltoluene or an unsaturated aliphatic hydrocarbon compound having 4 or 5 carbon atoms with respect to the total amount of its structural unit.
  • the content of the structural unit is preferably 2 mol% or more and 60 mol% or less, more preferably 4 mol% or more and 40 mol% or less, and further preferably 5 mol% or more and 20 mol% or less. ..
  • the (co) polymer (B) may be a copolymer having a structural unit derived from other monomers other than the above-mentioned isopropenyltoluene and the like.
  • Tg glass transition temperature
  • Examples of the above other monomers include vinyl aromatic compounds, unsaturated aliphatic hydrocarbon compounds other than 4 or 5 carbon atoms, and the like.
  • Examples of the vinyl aromatic compound include a substituted styrene having a substituent on the aromatic ring and a styrene-based monomer containing a substituted ⁇ -methylstyrene having a substituent on the aromatic ring.
  • Examples of the substituent contained in the aromatic ring include an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a halogen atom.
  • the vinyl aromatic compound may have one of the above substituents on the aromatic ring, or may have two or more of the above substituents on the aromatic ring.
  • substituted styrene examples include methyl styrene (excluding ⁇ -methyl styrene), ethyl styrene, 2,4-dimethyl styrene, pn-butyl styrene, p-tert-butyl styrene, and pn-hexyl styrene.
  • the (co) polymer (B) can be synthesized by a known polymerization method using isopropenyltoluene and other monomers copolymerized arbitrarily.
  • the above-mentioned polymerization is preferably cationic polymerization, and more preferably carried out in the presence of a Friedel-Crafts catalyst.
  • the Friedel-Crafts catalyst includes various complexes such as aluminum chloride, aluminum bromide, dichloromonoethyl aluminum, titanium tetrachloride, tin tetrachloride, boron trifluoride, and an ether complex or phenol complex of boron trifluoride. It is not particularly limited as long as it is a known Friedel-Crafts catalyst including. Of these, a phenol complex of boron trifluoride is preferable.
  • the amount of the Friedel-Crafts catalyst used can be 0.05 parts by mass or more and 5 parts by mass or less, and 0.1 parts by mass or more and 2 parts by mass or less with respect to 100 parts by mass of the total raw material monomers. Is preferable.
  • the polymerization reaction is preferably carried out using a solvent so that the concentration of the raw material monomer is about 10 to 60% by mass from the viewpoints of removing the heat of reaction generated during the polymerization reaction, suppressing the viscosity of the reaction solution, adjusting the molecular weight, and the like. ..
  • solvents include aliphatic hydrocarbons including pentane, hexane, heptane, and octane, alicyclic hydrocarbons including cyclopentane, cyclohexane, and methylcyclohexane, and toluene, xylene, ethylbenzene, and mesitylene. Includes aromatic hydrocarbons and the like.
  • One of these solvents may be used alone, or a plurality of types may be used in combination.
  • the above-mentioned polymerization can be carried out by polymerizing the raw material monomer in the above-mentioned solvent in the presence of the above-mentioned catalyst in the reactor. Although the above-mentioned polymerization can be carried out in one stage, it is preferable to carry out the polymerization in a plurality of stages.
  • the polymerization temperature at this time varies depending on the composition of the raw material, the target molecular weight region, and the like, but is preferably ⁇ 50 to + 50 ° C.
  • the reaction time at this time is preferably 10 minutes to 10 hours.
  • the catalyst is decomposed with a basic aqueous solution or a basic compound containing alcohol such as methanol, washed with water, and unreacted raw materials and solvents are stripped or distilled. Except for this, the desired (co) polymer (B) can be obtained.
  • an operation of concentrating using the difference in vapor pressure for each substance including atmospheric distillation, vacuum distillation, steam distillation, etc., and an open column and a flash column, etc. It can be carried out by a method of concentrating by utilizing the difference in affinity and molecular size for a filler such as silica gel contained.
  • vacuum distillation is preferable from the viewpoint of suppressing thermal decomposition and concentration efficiency.
  • the range of the decompression is not particularly limited.
  • the heating temperature is preferably 250 ° C. or lower, more preferably 230 ° C. or lower, and preferably 210 ° C. or lower. More preferred.
  • Cross-linking agent (C) cross-links the (meth) acrylic resin (A) to further enhance the stickiness of the sticky composition according to the present embodiment.
  • cross-linking agent (C) examples include sorbitol polyglycidyl ether, polyglycerol polyglycidyl ether, pentaerythritol polyglycidyl ether, diglycerol polyglycidyl ether, glycerol polyglycidyl ether, neopentyl glycol diglycidyl ether, and resorcin diglycidyl.
  • melamine compounds including hexamethoxymethylol melamine and the like are included.
  • the cross-linking agent (C) has the number of functional groups that can be bonded to the (meth) acrylic resin (A) in the cross-linking agent (C) (when the cross-linking agent (C) contains a blocked isocyanate, the number of functional groups generated by dissociation of the blocking agent). Is preferably added to such an extent that the number of functional groups does not exceed the number of functional groups of the (meth) acrylic resin (A), but when a new functional group is generated by the cross-linking reaction or the progress of the cross-linking reaction is slow. In some cases, a larger amount may be blended.
  • the adhesive composition according to the present embodiment has 47 parts by mass or more when the total content of the (meth) acrylic resin (A), the (co) polymer (B) and the cross-linking agent (C) is 100 parts by mass. 99 parts by mass or less of (meth) acrylic resin (A), 0.5 parts by mass or more and 50 parts by mass or less of (co) polymer (B), and 0.5 parts by mass or more and 3 parts by mass or less of a cross-linking agent ( C) is contained.
  • the content of the (meth) acrylic resin (A) is 47 parts by mass or more, a larger amount of the (meth) acrylic resin (A) is contained in the adhesive composition, and the adhesive composition Since the crosslink density becomes higher and the molecular weight becomes higher, the adhesive composition is less likely to decrease in adhesiveness due to following the surface of the adherend during pressure bonding.
  • the content of the (meth) acrylic resin (A) is 99 parts by mass or less, a larger amount of the (co) polymer (B) and the cross-linking agent (C) will be contained in the adhesive composition. Therefore, the adhesiveness of the adhesive composition can be further increased.
  • the content of the (meth) acrylic resin (A) is preferably 57.2 parts by mass or more and 94 parts by mass or less, and 62.5 parts by mass or more and 88.5 parts by mass or less. More preferred.
  • the adhesiveness of the adhesive composition can be further enhanced.
  • the transparency of the adhesive composition can be further enhanced.
  • the content of the (co) polymer (B) is preferably 5 parts by mass or more and 40 parts by mass or less, and more preferably 10 parts by mass or more and 35 parts by mass or less.
  • the content of the cross-linking agent (C) When the content of the cross-linking agent (C) is 0.5 parts by mass or more, the adhesive composition tends to aggregate, and the adhesive composition remains on the surface of the adherend after pressure bonding, so-called adhesive residue occurs. Hateful.
  • the content of the cross-linking agent (C) is 3 parts by mass or less, a larger amount of the (meth) acrylic resin (A) is contained in the adhesive composition, and the cross-linking density of the adhesive composition becomes high. Since the height is higher and the molecular weight is higher, the adhesive composition is less likely to decrease in adhesiveness due to following the surface of the adherend during pressure bonding.
  • the content of the cross-linking agent (C) is preferably 1 part by mass or more and 2.8 parts by mass or less, and more preferably 1.5 parts by mass or more and 2.5 parts by mass or less.
  • the adhesive composition according to the present embodiment substantially does not contain a rosin resin or a terpene resin.
  • the rosin resin or terpene resin causes the adhesive composition to be colored or discolored.
  • a hydrogenated resin prepared by hydrogenating a rosin resin or a terpene resin may be used in the adhesive composition in order to suppress the above-mentioned coloring and the like, but these tend to reduce the adhesive holding power.
  • the rosin resin or the terpene resin has an acid value, if an adhesive composition containing these is attached to a metal, the metal may be corroded.
  • substantially free means that the content of the rosin resin or terpene resin with respect to the total mass of the adhesive composition is 0.1% by mass or less.
  • the above-mentioned (meth) acrylic resin (A), (co) polymer (B) and cross-linking agent (C) are optionally blended in an amount according to the above-mentioned content. It can be prepared by mixing with the solvent used.
  • Examples of the above solvent include ethyl acetate, butyl acetate, benzene, toluene, xylene, cyclohexane, methyl ethyl ketone and the like.
  • the adhesive composition according to the present embodiment can be used as an adhesive processed product such as a tape, a label, a sheet and a double-sided tape for various applications requiring adhesiveness.
  • the adhesive processed product has a base material layer and an adhesive layer, and the adhesive layer comprises an adhesive composition according to the present embodiment.
  • the thickness of the adhesive layer is not particularly limited, it is 5 ⁇ m or more and 50 ⁇ m or less from the viewpoint of imparting desired adhesiveness to the adhesive processed product and reducing the influence on the productivity of the adhesive processed product. It is preferably 5 ⁇ m or more and 40 ⁇ m or less, and further preferably 10 ⁇ m or more and 30 ⁇ m or less.
  • the base material is not particularly limited, but when the adhesive processed product is used for applications requiring transparency, a transparent resin film is preferable.
  • the adhesive processed product has an adhesive layer made of the adhesive composition, it can have high transparency.
  • the adhesive processed product can be an adhesive processed product having a total light transmittance of 87% or more measured in accordance with JIS K7361.
  • the adhesive processed product has an adhesive layer made of the adhesive composition, it can have high adhesiveness.
  • the adhesive processed product can be an adhesive processed product having an adhesive strength of 9 N / 25 mm or more measured by a 180 ° peel test using SUS on the J adherend.
  • the adhesive processed product can be produced by applying the adhesive composition to the surface of a base material, drying the applied adhesive composition, and cross-linking each component.
  • the above coating method is not particularly limited, and may be applied by a known method such as a roll coater method, a reverse roll coater method, a gravure roll method, a bar coat method, a comma coater method, and a die coater method.
  • the above drying conditions are also not particularly limited, and it is preferable to dry at 80 to 200 ° C. for 10 seconds to 10 minutes, and more preferably at 80 to 170 ° C. for 15 seconds to 5 minutes.
  • Tg Glass transition temperature
  • the glass transition temperature (Tg) of the (meth) acrylic resin (A) and the (co) polymer (B1) to (co) polymer (B3) is determined by enclosing these resins in a simple airtight pan and subjecting them to a nitrogen stream.
  • the DSC curve when the temperature was raised from ⁇ 100 ° C. to 200 ° C. at a rate of 10 ° C./min was analyzed and obtained in accordance with JIS K7121.
  • Number average molecular weight (Mn), weight average molecular weight (Mw), z average molecular weight (Mz) and molecular weight distribution of (meth) acrylic resin (A) and (co) polymer (B1) to (co) polymer (B3) (Mw / Mn) was determined from GPC measurement. The measurement was performed under the following conditions.
  • the number average molecular weight (Mn), the weight average molecular weight (Mw), and the z average molecular weight (Mz) were obtained from the calibration curve using commercially available monodisperse standard polystyrene, and Mw / Mn was calculated.
  • the content of the compound having a molecular weight of 400 or less was calculated by integrating the obtained molecular weight distribution.
  • EHA Ethylhexyl Acrylic Acid
  • EA Vinyl acetate
  • VA Acrylic acid
  • AA Hydroxyethyl acrylate
  • the glass transition temperature (Tg) of the (meth) acrylic resin (A1) obtained by volatilizing the solvent from the obtained solution was measured and found to be -60 ° C.
  • Mass ratio of isopropenyl toluene and C 5 fraction (5 fraction isopropenyltoluene / C) is 90/10 and then, the supply amount of the mixture of monomers and toluene was 1.0 l / hr, the supply amount of diluted catalyst was 105 ml / hour.
  • the reaction mixture was transferred to a second-stage autoclave, and the polymerization reaction was continued at 5 ° C. Then, when the total residence time in the first and second stages of the autoclave reaches 2 hours, the reaction mixture is continuously discharged from the autoclave, and when the residence time becomes 3 times, 1 liter. The reaction mixture was collected to terminate the polymerization reaction. After completion of the polymerization, 1N aqueous NaOH solution was added to the collected reaction mixture to decalcify the catalyst residue.
  • the (co) polymer (B4) has a structural unit content derived from isopropenyl toluene of 93 mol%, a softening point of 100 ° C., a glass transition temperature (Tg) of 50 ° C., and a number average molecular weight (Mn) of 700.
  • Z average molecular weight (Mz) is 1500
  • dispersity (Mw / Mn) which is the ratio of weight average molecular weight (Mw) to number average molecular weight (Mn) is 1.43
  • content of compounds having a molecular weight of 400 or less. was 13%.
  • the (co) polymer (B4) was placed in a glass container attached to the upper part of a thin film distillation apparatus (DN60 type, manufactured by Asahi Seisakusho Co., Ltd.) and then heated to 200 ° C. Then passed through the column at 2 ml / min, rpm 180 rpm, and concentrated in vacuum 0.02 Pa, a copolymer of isopropenyl toluene ⁇ C 5 fraction in a glass eggplant flask equipped with a bottom, (co ) The polymer (B1) was recovered.
  • DN60 type manufactured by Asahi Seisakusho Co., Ltd.
  • the (co) polymer (B1) has a structural unit content derived from isopropenyl toluene of 93 mol%, a softening point of 110 ° C., a glass transition temperature (Tg) of 65 ° C., and a number average molecular weight (Mn) of 850.
  • Z average molecular weight (Mz) is 1600
  • dispersity (Mw / Mn) which is the ratio of weight average molecular weight (Mw) to number average molecular weight (Mn) is 1.35
  • the content of compounds having a molecular weight of 400 or less. was 3%.
  • the condenser fitted as a step after the thin film distillation apparatus by aggregating a low boiling point component, an isopropenyl toluene ⁇ C 5 fraction of the copolymer was recovered (co) polymer (B6).
  • the (co) polymer (B6) has a structural unit content derived from isopropenyl toluene of 93 mol%, a softening point is not measured, a glass transition temperature (Tg) of -5 ° C., and a number average molecular weight (Mn).
  • the z average molecular weight (Mz) is 400
  • the dispersity (Mw / Mn) which is the ratio of the weight average molecular weight (Mw) to the number average molecular weight (Mn) is 1.03
  • (Synthesis of (co) polymer (B2)) Isopropenyltoluene in the same method as the synthesis of the (co) polymer (B4) except that the polymerization temperature in the first and second stages of the autoclave was 20 ° C. and the supply amount of the diluted catalyst was 50 ml / hour. a copolymer of C 5 fraction, was obtained (co) polymer (B2).
  • the (co) polymer (B2) has a structural unit content derived from isopropenyl toluene of 97 mol%, a softening point of 102 ° C., a glass transition temperature (Tg) of 65 ° C., and a number average molecular weight (Mn) of 850.
  • Z average molecular weight (Mz) is 1650
  • dispersity (Mw / Mn) which is the ratio of weight average molecular weight (Mw) to number average molecular weight (Mn) is 1.41
  • content of compounds having a molecular weight of 400 or less. was 6%.
  • the (co) polymer (B3) has a structural unit content derived from isopropenyl toluene of 100 mol%, a softening point of 102 ° C., a glass transition temperature (Tg) of 60 ° C., and a number average molecular weight (Mn) of 770.
  • Z average molecular weight (Mz) is 1400
  • dispersity (Mw / Mn) which is the ratio of weight average molecular weight (Mw) to number average molecular weight (Mn) is 1.31
  • the content of compounds having a molecular weight of 400 or less. was 7%.
  • (Synthesis of (co) polymer (B5)) The supply amount of diluted catalyst except that 90 ml / time is combined with the same method, isopropenyltoluene ⁇ C 5 fraction of a copolymer of (co) polymers (B4), (co) polymer (B5) was obtained.
  • the (co) polymer (B5) has a structural unit content derived from isopropenyl toluene of 93 mol%, a softening point of 110 ° C., a glass transition temperature (Tg) of 70 ° C., and a number average molecular weight (Mn) of 900.
  • Z average molecular weight (Mz) is 2400
  • dispersity (Mw / Mn) which is the ratio of weight average molecular weight (Mw) to number average molecular weight (Mn) is 1.67
  • content of compounds having a molecular weight of 400 or less. was 8%.
  • the (co) polymer (B7) has a structural unit content derived from ⁇ -methylstyrene of 55 mol%, a softening point of 97 ° C., a glass transition temperature (Tg) of 55 ° C., and a number average molecular weight (Mn) of 55 ° C. 840, z average molecular weight (Mz) is 3000, dispersity (Mw / Mn), which is the ratio of weight average molecular weight (Mw) to number average molecular weight (Mn), is 1.98, and contains compounds with a molecular weight of 400 or less. The rate was 14%.
  • composition softening point, glass transition temperature (Tg), number average molecular weight (Mn), z average molecular weight (Mz), weight average molecular weight (Mw) of (co) polymer (B1) to (co) polymer (B7).
  • Tg glass transition temperature
  • Mn number average molecular weight
  • Mz z average molecular weight
  • Mw weight average molecular weight
  • IPT isopropenyltoluene.
  • Cross-linking agent (C) As the cross-linking agent (C1), Takenate D-101E manufactured by Mitsui Chemicals, Inc. (isocyanate compound, "Takenate” is a registered trademark of the same company) was used.
  • An ethyl acetate / toluene solution containing the (meth) acrylic resin (A1), any of the (co) polymers (B1) to (co) polymers (B7), and a cross-linking agent (C) are contained in the solution.
  • the ratio of the (meth) acrylic resin (A1) contained in, any of the (co) polymer (B1) to (co) polymer (B3), and the cross-linking agent (C) is the mass ratio shown in Table 2.
  • the mixture was mixed at room temperature so as to obtain an ethyl acetate / toluene solution of the adhesive composition.
  • the obtained ethyl acetate / toluene solution of the adhesive composition is applied to a release paper so that the film thickness after drying is 10 to 50 ⁇ m, dried at 100 ° C. for 10 minutes, and then a PET film of 25 ⁇ m is applied to the coated surface. It was crimped to prepare an adhesive sheet.
  • the adhesive composition was sufficiently crosslinked by leaving it at 50 ° C. for 3 days.
  • the release paper of the pressure-sensitive adhesive sheet having a film thickness of 50 ⁇ m was peeled off to expose the pressure-sensitive adhesive layer, and a PET film having a thickness of 25 ⁇ m was pressure-bonded to the exposed pressure-sensitive adhesive layer to obtain a test piece.
  • the pressure-sensitive adhesive sheet having a film thickness of 15 ⁇ m or 30 ⁇ m was cut into a test piece having a width of 25 mm and a length of 150 mm.
  • the release paper of the test piece is peeled off to expose the adhesive layer, the exposed adhesive layer is brought into contact with a stainless plate (SUS) in an atmosphere of 23 ° C., and a rubber roll having a mass of 2 kg is reciprocated twice to perform the test.
  • the piece was crimped. After leaving for 20 minutes, the 180 ° peel strength was measured at a speed of 300 mm / min according to JIS Z0237.
  • Tables 2 and 3 show the composition of the adhesive composition constituting the produced adhesive processed product, and the total light transmittance and adhesive strength of the adhesive processed product.
  • FIG. 1 shows the relationship between the total light transmittance and the adhesive force when the film thickness of the adhesive layer is 15 ⁇ m in Examples 1 to 5 and Comparative Examples 1 to 9.
  • the adhesiveness containing the (co) polymer is higher than that of the adhesive composition containing no (co) polymer containing structural units derived from isopropenyl toluene.
  • the composition had higher adhesive strength.
  • the adhesive composition containing the (co) polymer that satisfies all of the requirements (B-1) to (B-5) does not satisfy any of the requirements (B-1) to (B-5) ( Both the adhesive strength and the transparency were higher than those of the adhesive composition containing the polymer.
  • an adhesive composition having high transparency and adhesiveness is provided.
  • the present invention can be suitably carried out in various applications in which the transparency of the adhesive composition is particularly required.

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