WO2024095322A1 - Composition adhésive, feuille adhésive formée de ladite composition adhésive, et article utilisant ladite feuille adhésive - Google Patents

Composition adhésive, feuille adhésive formée de ladite composition adhésive, et article utilisant ladite feuille adhésive Download PDF

Info

Publication number
WO2024095322A1
WO2024095322A1 PCT/JP2022/040745 JP2022040745W WO2024095322A1 WO 2024095322 A1 WO2024095322 A1 WO 2024095322A1 JP 2022040745 W JP2022040745 W JP 2022040745W WO 2024095322 A1 WO2024095322 A1 WO 2024095322A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
mass
acrylate
adhesive
adhesive layer
Prior art date
Application number
PCT/JP2022/040745
Other languages
English (en)
Japanese (ja)
Inventor
嶺 木本
剛 田中
靖史 土屋
Original Assignee
株式会社寺岡製作所
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 株式会社寺岡製作所 filed Critical 株式会社寺岡製作所
Priority to PCT/JP2022/040745 priority Critical patent/WO2024095322A1/fr
Publication of WO2024095322A1 publication Critical patent/WO2024095322A1/fr

Links

Images

Classifications

    • 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
    • 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
    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00

Definitions

  • the present invention relates to an adhesive composition containing hollow microparticles, an adhesive sheet formed from the adhesive composition, and an article in which the adhesive sheet is used.
  • foam adhesive tapes that use foamed resin materials as a base material
  • foam adhesive tapes have excellent stress relaxation properties, so they also have excellent adhesion to components with steps or unevenness, and can be used for a wider range of adherends than double-sided tapes that use nonwoven fabric or resin film as a base material.
  • foam adhesive tape the resin that makes up the foam softens at high temperatures, which raises concerns that the air bubbles inside the tape may collapse and the stress relaxation properties described above may be lost.
  • foam adhesive tape usually requires a separate adhesive layer to be laminated, and the adhesive strength of the adhesive layer generally decreases at high temperatures. In other words, there are limitations to its use in automotive parts that are expected to be used in high-temperature environments.
  • Patent Document 1 discloses an adhesive sheet having an adhesive layer formed from an ultraviolet-curable adhesive composition containing hollow microspheres and having excellent shear strength and adhesive strength (adhesive strength) in a high-temperature environment.
  • This document states that it is preferable to use hollow inorganic microspheres as hollow microspheres (hollow microspheres) from the viewpoint of efficiency and weight of polymerization using ultraviolet reaction, and further that it is possible to improve high-temperature adhesive strength without impairing other properties such as shear strength and holding power by using hollow glass balloons.
  • Patent Document 2 discloses an adhesive sheet including an adhesive layer containing an acrylic polymer and hollow fine particles and containing no air bubbles. It is said that this adhesive sheet can more preferably use hollow inorganic fine particles among hollow fine particles from the viewpoint of the efficiency of polymerization using ultraviolet reaction, weight, etc.
  • the pressure-sensitive adhesive sheet of Patent Document 2 is said to have both adhesiveness and reworkability, but no particular consideration is given to adhesive strength or flexibility at high temperatures. According to the findings of the present inventors, the glass balloon content (9 to 12 parts) disclosed in the examples and reference examples of Patent Document 2 is effective in improving reworkability, but the flexibility of the pressure-sensitive adhesive sheet is poor, and it is expected that the adhesive strength will decrease at high temperatures.
  • JP 2008-88408 A Patent No. 5408640
  • JP 2013-221073 A Patent No. 5950669
  • the object of the present invention is to provide an adhesive composition capable of forming an adhesive layer that has excellent flexibility and excellent adhesive strength even at high temperatures, an adhesive sheet formed from the adhesive composition, and an article using the adhesive sheet.
  • an adhesive sheet having an adhesive layer made of the above-mentioned adhesive composition, and an article using the adhesive sheet.
  • the (meth)acrylic syrup (a) used in the adhesive composition of the present invention contains a copolymer having the above-mentioned two types of functional group-containing (meth)acrylate as an essential component, and therefore is easy to form a crosslinked structure regardless of the type of crosslinking agent (e). Therefore, the adhesive layer formed from the adhesive composition of the present invention can maintain high adhesive strength even at high temperatures.
  • the adhesive layer is highly polarized by these functional groups, and therefore can obtain excellent adhesive strength, particularly to metals.
  • the tackifier resin (b) is an essential component, the initial adhesive strength to members having irregularities or steps can be increased.
  • the compressive strength and tensile strength of the adhesive layer after formation are within a specified range, making it possible to achieve a balance between the ability to conform to uneven surfaces, the ability to attach to curved surfaces, and adhesive strength at high temperatures.
  • 1 is a schematic cross-sectional view of a pressure-sensitive adhesive sheet according to one embodiment of the present invention.
  • 1 is a schematic cross-sectional view of a pressure-sensitive adhesive sheet according to one embodiment of the present invention.
  • 1 is a schematic cross-sectional view of a pressure-sensitive adhesive sheet according to one embodiment of the present invention.
  • 1 is a schematic cross-sectional view of a pressure-sensitive adhesive sheet according to one embodiment of the present invention.
  • 1 is a schematic cross-sectional view of a pressure-sensitive adhesive sheet according to one embodiment of the present invention.
  • the pressure-sensitive adhesive composition according to the present invention comprises: (a) 100 parts by mass of a syrup obtained by mixing a (meth)acrylic copolymer having as its constituent components an alkyl (meth)acrylate and a (meth)acrylate having a carboxyl group, an alkyl (meth)acrylate monomer, a (meth)acrylate monomer having a carboxyl group, and a (meth)acrylate monomer having a hydroxyl group; (b) 0.5 to 10 parts by mass of a tackifier resin; (c) 0.1 to 3.0 parts by mass of hollow fine particles; (d) 0.1 to 5 parts by mass of a photopolymerization initiator; (e) 0.01 to 5 parts by mass of a crosslinking agent; A pressure-sensitive adhesive composition comprising: the hollow fine particles (c) are resin-based hollow fine particles having a shell portion made of an organic poly
  • the syrup of component (a) is a mixture of a (meth)acrylic copolymer (a1) having as its constituent components monomer units derived from an alkyl (meth)acrylate and a (meth)acrylate having a carboxyl group, an alkyl (meth)acrylate monomer (a2), a (meth)acrylate monomer having a carboxyl group (a3), and a (meth)acrylate monomer having a hydroxyl group (a4).
  • the copolymer (a1) contains, as constituent components, monomer units derived from an alkyl (meth)acrylate and a (meth)acrylate having a carboxyl group.
  • alkyl (meth)acrylate include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, tertiary butyl (meth)acrylate, hexyl (meth)acrylate, isohexyl (meth)acrylate, octyl (meth)acrylate, isooctyl (meth)acrylate, ethylhexyl (meth)acrylate, nonyl (meth)acrylate, isononyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate,
  • a unit derived from a monomer having a relatively long alkyl chain may be used alone or in combination of two or more.
  • the proportion of the monomer units derived from alkyl (meth)acrylate relative to 100% by mass of all monomer units constituting the copolymer (a1) is preferably from 80 to 99% by mass, and more preferably from 85 to 95% by mass.
  • Examples of (meth)acrylates having a carboxyl group include (meth)acrylic acid, ⁇ -carboxyethyl (meth)acrylate, itaconic acid, crotonic acid, maleic acid, and fumaric acid.
  • (meth)acrylic acid is preferred from the viewpoint of higher strength of the acrylic resin composition.
  • the proportion of monomer units derived from a (meth)acrylate having a carboxyl group relative to 100% by mass of all monomer units constituting the copolymer (a1) is preferably from 1 to 20% by mass, and more preferably from 5 to 15% by mass.
  • the copolymer (a1) may contain (meth)acrylic monomer units other than those mentioned above, provided that the effects of the present invention are not impaired.
  • examples of such units include nitrogen-containing acrylic monomer units such as (meth)acrylamide, which will be described later, and units derived from a (meth)acrylate monomer (a4) having a hydroxyl group.
  • the copolymer (a1) is obtained by copolymerizing the above-mentioned monomer components, and the polymerization method is not particularly limited.
  • various polymerization methods such as solution polymerization, bulk polymerization, suspension polymerization, and emulsion polymerization can be performed using means such as photopolymerization or thermal polymerization.
  • polymerization by radiation such as gamma rays and electron beam polymerization can also be used.
  • Photopolymerization can be performed, for example, by irradiating the monomer composition with UV rays in the presence of a photopolymerization initiator.
  • Thermal polymerization can be performed, for example, by heating the monomer composition to 50 to 200°C in the presence of a thermal polymerization initiator. It is also preferable to adjust the molecular weight by using a chain transfer agent such as a thiol compound in combination during polymerization. In addition, although unreacted monomers may remain, they can be used as a constituent component of the syrup (a) as is, so there is no need to isolate the copolymer. When the copolymer (a1) reaches 5 to 50% by mass, the polymerization is stopped to make a partial copolymer, which can be handled as a viscous liquid.
  • the copolymer (a1) means one having a weight average molecular weight (Mw) of 100,000 or more. The Mw of the copolymer (a1) is preferably from 100,000 to 2,000,000, and more preferably from 500,000 to 1,500,000.
  • alkyl (meth)acrylate monomer (a2) the alkyl (meth)acrylates listed as monomer components constituting the copolymer (a1) can be used.
  • the (meth)acrylate monomer (a3) having a carboxyl group the (meth)acrylates listed as monomer components constituting the copolymer (a1) can be used. These may be used alone or in combination of two or more.
  • Examples of the (meth)acrylate monomer (a4) having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxyhexyl (meth)acrylate, and monoesters of (meth)acrylic acid with polyethylene glycol or polypropylene glycol. These may be used alone or in combination of two or more.
  • nitrogen-containing acrylic monomers may be included as other monomers.
  • nitrogen-containing acrylic monomers include (meth)acrylamide, N-alkyl-substituted (meth)acrylamides such as N-isopropyl (meth)acrylamide, N,N-dialkyl-substituted (meth)acrylamides such as N,N-dimethyl (meth)acrylamide and N,N-diethyl (meth)acrylamide, acryloylmorpholine, vinylpyridine, N-vinylpyrrolidone, aminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, and dimethylaminopropyl (meth)acrylate.
  • (meth)acrylamide, N-alkyl-substituted (meth)acrylamide, N,N-dialkyl-substituted (meth)acrylamide, and acryloylmorpholine are preferred from the viewpoints of versatility and industrial commercialization. These may be used alone or in combination of two or more.
  • the amounts of the components in the syrup are preferably 5-50% by mass of copolymer (a1) and a total of 50-95% by mass of other monomer components (a2)-(a4), and more preferably 8-40% by mass of copolymer (a1) and a total of 60-92% by mass of other monomer components (a2)-(a4), taking the total as 100% by mass.
  • the ratio of the other monomer components (a2)-(a4) is preferably (a2)>(a3)>(a4).
  • Tackifying Resin As the tackifying resin, various tackifying resins such as hydrogenated petroleum resins, rosin-based resins, terpene-based resins, hydrocarbon-based resins, and phenol-based resins can be used. These can be used alone or in combination of two or more.
  • the tackifier resin (b) is blended in an amount of 0.5 to 10 parts by mass per 100 parts by mass of syrup (a), preferably 1 to 10 parts by mass per 100 parts by mass of syrup (a), and more preferably 2 to 8 parts by mass per 100 parts by mass of syrup (a).
  • the hollow fine particles constituting the pressure-sensitive adhesive composition according to the present invention are resin-based hollow fine particles having a shell made of an organic polymer material.
  • the organic polymer material constituting the shell is preferably, for example, a resin containing acrylonitrile as a constituent unit.
  • the average particle diameter of the hollow fine particles is preferably 1 to 150 ⁇ m, more preferably 10 to 130 ⁇ m.
  • the average particle diameter referred to here is the median diameter (D50) based on volume. In addition, in the case of commercially available products, the selection may be made based on the catalog value.
  • the thickness of the shell is preferably 0.1 to 20 ⁇ m, and more preferably 2 to 15 ⁇ m.
  • the hollow microparticles preferably contain hydrocarbons in their hollows and function as thermally expandable balloons.
  • the organic polymer material (thermoplastic resin) that constitutes the shell first begins to soften, the encapsulated hydrocarbons begin to gasify, the internal pressure rises, and the balloon expands. However, once the temperature exceeds a certain level, the gas permeates and escapes from the shell, and the balloon begins to shrink.
  • the content of the hollow fine particles in the acrylic resin composition is 0.1 to 3.0 parts by mass, and preferably 0.5 to 2 parts by mass, based on 100 parts by mass of the syrup (a).
  • the hollow fine particles may be appropriately subjected to a surface treatment such as a coupling treatment or a stearic acid treatment.
  • Photopolymerization initiator As the photopolymerization initiator, a photoradical polymerization initiator can be used, and examples thereof include known polymerization initiators such as alkylphenones, acylphosine oxides, oxyphenyl acetates, etc. The alkylphenones are further classified into benzyl ketals, ⁇ -hydroxyalkylphenones, ⁇ -hydroxyacetophenones, ⁇ -aminoalkylphenones, etc.
  • the photopolymerization initiator (d) is blended in an amount of 0.1 to 5 parts by mass, preferably 0.2 to 2 parts by mass, and more preferably 0.3 to 1 part by mass, per 100 parts by mass of the syrup (a).
  • the pressure-sensitive adhesive composition according to the present invention preferably contains a crosslinking agent from the viewpoint of forming a crosslinked structure.
  • a crosslinking agent from the viewpoint of reactivity with the acrylic syrup (a), at least one crosslinking agent selected from the group consisting of polyfunctional (meth)acrylic monomers, polyfunctional (meth)acrylic oligomers, bifunctional or higher glycidyl group-containing compounds, and bifunctional or higher isocyanate group-containing compounds is preferable.
  • polyfunctional (meth)acrylic monomers include trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 1,2-ethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, etc.
  • polyfunctional (meth)acrylic oligomers include urethane (meth)acrylates and epoxy (meth)acrylates that are oligomerized by reacting a compound having multiple isocyanate groups or glycidyl groups with (meth)acrylic acid or a hydroxyl group-containing (meth)acrylate.
  • difunctional or higher glycidyl group-containing compounds examples include 1,3-bis(N,N-diglycidylaminomethyl)cyclohexane, N,N,N',N'-tetraglycidyl-m-xylylenediamine, N,N,N',N'-tetraglycidylaminophenylmethane, triglycidyl isocyanurate, m-N,N-diglycidylaminophenyl glycidyl ether, N,N-diglycidyl toluidine, N,N-diglycidyl aniline, pentaerythritol polyglycidyl ether, and 1,6-hexanediol diglycidyl ether.
  • bifunctional or higher isocyanate group-containing compounds include isocyanate monomers such as tolylene diisocyanate (TDI), chlorophenylene diisocyanate, hexamethylene diisocyanate, tetramethylene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, and hydrogenated diphenylmethane diisocyanate, as well as isocyanate compounds, isocyanurates, and biuret-type compounds in which these isocyanate monomers are added to trimethylolpropane, and further urethane prepolymer-type isocyanates in which these are added to polyether polyols, polyester polyols, acrylic polyols, polybutadiene polyols, and polyisoprene polyols. These crosslinking agents can be used alone or in combination of two or more.
  • TDI tolylene diisocyanate
  • chlorophenylene diisocyanate
  • the amount of crosslinking agent in the acrylic resin composition is preferably 0.01 to 10 parts by mass, more preferably 0.03 to 1 part by mass, and even more preferably 0.05 to 0.5 parts by mass, per 100 parts by mass of the polymer (total monomers before polymerization).
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition according to the present invention after crosslinking has a 25% compressive strength of 0.06 to 0.11 MPa and a tensile strength at 23° C. of 0.35 to 0.65 MPa.
  • the 25% compressive strength is a value measured by the method described in the Examples below, and if the compressive strength is less than 0.06 MPa, it becomes difficult for the sheet to maintain its shape, and if it exceeds 0.11 MPa, the ability to conform to steps and curved surfaces decreases.
  • the compressive strength is more preferably 0.06 to 0.10 MPa.
  • the tensile strength of the pressure-sensitive adhesive layer at 23°C is a value measured by the method described in the Examples below, and if the tensile strength is less than 0.35 MPa, the cohesive strength of the pressure-sensitive adhesive layer is weak, resulting in a decrease in holding power, while if it exceeds 0.65 MPa, the cohesive strength is too strong, resulting in a decrease in peel strength.
  • the tensile strength is more preferably 0.38 to 0.56 MPa.
  • the peel strength of the pressure-sensitive adhesive layer is not particularly limited as long as it has a peel strength appropriate for the purpose, but it is preferable that the peel strength of the pressure-sensitive adhesive layer after crosslinking formed from the pressure-sensitive adhesive composition of the present invention has little change between room temperature (23°C) and high temperature (90°C).
  • the adhesive composition of the present invention may contain various additives known in the field of the present invention, provided that they do not affect the above-mentioned compressive strength and tensile strength.
  • additives include flame retardants, pigments, antioxidants, lubricants, etc., and may contain one or a combination of two or more of these.
  • the adhesive composition according to the present invention can be used as an adhesive layer formed by forming the adhesive composition into a sheet and crosslinking it.
  • the adhesive layer may be formed into a sheet on its own, or may be used as a tape-like material in which an adhesive layer is formed on a substrate. In particular, it is preferably used as a double-sided adhesive sheet for bonding articles together, as described below.
  • Such sheet-like and tape-like materials are collectively referred to as adhesive sheets in this specification.
  • FIGS. 1 to 5 are schematic cross-sectional views illustrating the layer structure of the adhesive sheet of the present invention.
  • FIG. 1 shows a sheet composed solely of an adhesive layer using the adhesive composition of the present invention, with hollow fine particles 2 dispersed in the crosslinked adhesive layer 1.
  • the top and bottom surfaces of the sheet are adhesive surfaces, constituting a double-sided adhesive sheet.
  • a release film is provided on the adhesive surface, and when adhering an article, the release film is peeled off and the adhesive surface is attached to the surface to which the article is to be adhered.
  • Fig. 2 shows an adhesive sheet in which an adhesive layer 1 is disposed on one side of a substrate 3, and a design can be applied by printing or the like to the non-adhesive side of the substrate 3. Therefore, a receiving layer (not shown) suitable for printing or the like can be provided on the non-adhesive side of the substrate 3.
  • Fig. 3 shows an adhesive sheet in which an adhesive layer 1 is disposed on both sides of the substrate 3.
  • the substrate may be any substrate used in the field and has excellent adhesive strength with the pressure-sensitive adhesive layer of the present invention. For example, known films, nonwoven fabrics, foams, cloths, papers, and combinations thereof may be used.
  • the thickness of the substrate is not particularly limited, but can be selected, for example, from the range of 1 ⁇ m or more and 200 ⁇ m or less.
  • the surface of the substrate on which the pressure-sensitive adhesive layer is to be formed may be subjected to an easy-adhesion treatment, if necessary.
  • easy-adhesion treatments include primer treatment, corona treatment, etching treatment, plasma treatment, sandblasting treatment, etc. One or a combination of two or more of these may be selected.
  • the substrate may be subjected to a surface treatment such as antistatic treatment as required.
  • the antistatic treatment include treatment with an antistatic agent such as a cationic surfactant, an anionic surfactant, or a nonionic surfactant.
  • the substrate may be subjected to a coloring treatment by printing, kneading, or the like as required.
  • Figure 4 shows an adhesive sheet having one adhesive surface which is an adhesive layer 1 containing hollow microparticles 2 according to the present invention, and the other surface which is a laminate of an adhesive layer 4 which does not contain hollow microparticles 2.
  • Figure 5 shows an adhesive sheet which is a laminate in which a substrate 3 is inserted between adhesive layer 1 and adhesive layer 4.
  • An adhesive layer 4 which does not contain hollow microparticles 2 may have inferior step conformability compared to an adhesive layer 1 containing hollow microparticles 2, but as long as the surface to be bonded by adhesive layer 4 is flat, there is no problem even if the step conformability is inferior.
  • adhesive layer 4 a conventionally known adhesive layer or an adhesive layer obtained by removing hollow microparticles from adhesive layer 1 can be used.
  • the method for producing the adhesive layer is not particularly limited, and any conventionally known method can be used.
  • Articles using the adhesive sheet of the present invention include those used in fields such as automobile parts and machine parts, and can be used to bond and adhere articles that are exposed to temperatures of, for example, 50°C or higher during the manufacturing and use processes.
  • parts means “parts by mass.”
  • HEA hydroxyethyl acrylate, manufactured by Osaka Organic Chemical Industry Co., Ltd.
  • AM-90G methoxypolyethylene glycol acrylate (product name: NK Ester AM-90G), manufactured by Shin-Nakamura Chemical Co., Ltd.
  • IBOA isobornyl acrylate, manufactured by Osaka Organic Chemical Industry Co., Ltd.
  • ACMO acryloylmorpholine, manufactured by KJ Chemicals Co., Ltd.
  • P-125 Hydrogenated petroleum resin (softening point 125 ⁇ 5°C, product name: Alcon P-125), manufactured by Arakawa Chemical Industries Co., Ltd.
  • P-140 Hydrogenated petroleum resin (softening point 140 ⁇ 5°C, product name: Alcon P-140), manufactured by Arakawa Chemical Industries Co., Ltd.
  • P-90 Hydrogenated petroleum resin (softening point 90 ⁇ 5°C, product name: Alcon P-90), manufactured by Arakawa Chemical Industries Co., Ltd.
  • G125 Terpene phenol resin (softening point 125 ⁇ 5°C, product name: YS Polystar G125), manufactured by Yasuhara Chemical Co., Ltd.
  • KE-100 Hydrogenated rosin ester (softening point 100 ⁇ 5°C, product name: Pine Crystal KE-100), manufactured by Arakawa Chemical Industries Co., Ltd.
  • F-80DE acrylonitrile copolymer hollow microparticles (average particle size 90 to 130 ⁇ m), manufactured by Matsumoto Yushi Seiyaku Co., Ltd.
  • F-80SDE acrylonitrile copolymer hollow microparticles (average particle size 20 to 40 ⁇ m), manufactured by Matsumoto Yushi Seiyaku Co., Ltd.
  • 30P70T inorganic hollow microparticles, manufactured by Potters Ballotini Co., Ltd.
  • HAP photopolymerization initiator (d))
  • HAP ⁇ -hydroxyacetophenone (product name: Omnirad 1173), manufactured by IGM Resins
  • the pressure-sensitive adhesive sheets prepared above were subjected to the following evaluations. The results are shown in Tables 3-1 to 3-4.
  • (Tensile test of adhesive sheet) In accordance with JIS Z 0237, a pressure-sensitive adhesive sheet having a thickness of 800 ⁇ m, a width of 25 mm, and a length of 100 mm was pulled and the maximum tensile strength was measured using a tensile tester (Strograph V-1C, manufactured by Toyo Seiki Co., Ltd.) under conditions of 23° C., 50% RH, a gripping distance of 30 mm, and a test speed of 300 mm/min. The maximum tensile strength was also measured under the same conditions, with the temperature changed to 90° C.
  • the adherends were prepared as follows: a SUS 304 steel plate with a thickness of 1.5 mm, 50 mm and length of 125 mm and a BA surface (cold rolled and then bright heat treated) washed with acetone, and a polypropylene (PP) plate with a thickness of 2.0 mm, 50 mm and length of 125 mm washed with isopropyl alcohol.
  • the prepared adhesive sheet was cut to 10 mm x 130 mm, one side of the release film on both sides of the adhesive sheet was peeled off, and a polyester film 50 ⁇ m thick, 15 mm wide, and 300 mm long was attached to it.
  • the release film on the other side was peeled off, and the sheet was lightly attached to the adherend, and then a 5 kg roller was used to reciprocate and press the sheet against the test piece at a speed of about 300 mm per minute.
  • the sheet was left at room temperature for 24 hours, and then the end of the pressure-sensitive adhesive sheet was folded back at 180 degrees and continuously peeled off at a speed of 50 ⁇ 5 mm per minute in an atmosphere of 23°C and 50% RH, and the average test force (unit: N/10 mm) was read.
  • the results were displayed as SUS (23°C) and PP (23°C).
  • test pieces that had been laminated and pressed together were left at room temperature for 24 hours, and then the ends of the pressure-sensitive adhesive sheet were folded back at 180 degrees and left in a hot air circulating thermostatic chamber at 90 ⁇ 3°C for 1 hour, after which the sheets were continuously peeled off at a speed of 50 ⁇ 5 mm per minute in an atmosphere of 90°C, and the average test force was read.
  • the results were displayed as SUS (90°C) and PP (90°C).
  • the rate of change in peel strength was calculated by dividing the difference in peel strength between 23° C. and 90° C. by the peel strength at 23° C., and the results are shown in Tables 3-1 to 3-4.
  • the adherend was a polished SUS plate that had been polished back and forth 30 times with #280 abrasive paper and then washed with acetone.
  • the release liner was peeled off from one side of an adhesive sheet cut to a size of 25 mm x 25 mm and attached to the end of the polished SUS plate.
  • the sheet was then pressed back and forth from above the test piece using a 5 kg roller at a speed of approximately 300 mm per minute, after which the release liner on the opposite side was peeled off and aluminum foil of a thickness of 130 ⁇ 20 ⁇ m was similarly attached.
  • the sample was left for 24 hours, and then a weight of 1 ⁇ 0.01 kg was hung on the aluminum foil side.
  • the sample was left for 1 hour in a hot air circulating thermostatic chamber at 90 ⁇ 3° C., and the presence or absence of falling was confirmed (A: no, B: yes).
  • the adhesive composition of the present invention is capable of forming an adhesive layer that has excellent flexibility and excellent adhesive strength even at high temperatures, and is capable of maintaining the desired adhesive strength even in the manufacture of articles that have irregularities and are subjected to high-temperature processing.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesive Tapes (AREA)

Abstract

L'invention concerne une composition adhésive comprenant 100 parties en masse de (a) sirop obtenu par mélange d'un copolymère (méth)acrylique contenant un (méth)acrylate d'alkyle et un (méth)acrylate contenant un groupe carboxyle en tant que composants constitutifs, d'un monomère de (méth)acrylate d'alkyle, d'un monomère de (méth)acrylate contenant un groupe carboxyle et d'un monomère de (méth)acrylate contenant un groupe hydroxyle, de 0,5 à 10 parties en masse de (b) une résine collante, de 0,1 à 3,0 parties en masse de (c) de fines particules creuses, de 0,1 à 5 parties en masse de (d) un initiateur de photopolymérisation, et de 0,01 à 5 parties en masse de (e) un agent de réticulation : les fines particules creuses (c) sont de fines particules creuses à base de résine ayant une partie écorce composée d'un matériau polymère organique ; la résistance à la compression à 25 % d'une couche adhésive réticulée formée de la composition adhésive est de 0,06 à 0,11 MPa ; et la résistance à la traction de la couche adhésive à 23 °C est de 0,35 à 0,65 MPa. La composition adhésive peut former une couche adhésive ayant une excellente flexibilité et ayant une excellente force adhésive même à une température élevée.
PCT/JP2022/040745 2022-10-31 2022-10-31 Composition adhésive, feuille adhésive formée de ladite composition adhésive, et article utilisant ladite feuille adhésive WO2024095322A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/JP2022/040745 WO2024095322A1 (fr) 2022-10-31 2022-10-31 Composition adhésive, feuille adhésive formée de ladite composition adhésive, et article utilisant ladite feuille adhésive

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP2022/040745 WO2024095322A1 (fr) 2022-10-31 2022-10-31 Composition adhésive, feuille adhésive formée de ladite composition adhésive, et article utilisant ladite feuille adhésive

Publications (1)

Publication Number Publication Date
WO2024095322A1 true WO2024095322A1 (fr) 2024-05-10

Family

ID=90929992

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2022/040745 WO2024095322A1 (fr) 2022-10-31 2022-10-31 Composition adhésive, feuille adhésive formée de ladite composition adhésive, et article utilisant ladite feuille adhésive

Country Status (1)

Country Link
WO (1) WO2024095322A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014051644A (ja) * 2012-08-07 2014-03-20 Nitto Denko Corp 両面粘着シート及び携帯電子機器
JP2015117292A (ja) * 2013-12-18 2015-06-25 日東電工株式会社 粘着剤組成物および粘着テープ
JP2015117293A (ja) * 2013-12-18 2015-06-25 日東電工株式会社 熱拡散材および電子部品
WO2016152787A1 (fr) * 2015-03-24 2016-09-29 デクセリアルズ株式会社 Bande adhésive double face et son procédé de fabrication
KR20200065286A (ko) * 2018-11-30 2020-06-09 주식회사 영우 저밀도 아크릴 폼 점착테이프 및 이의 제조방법
JP7109698B1 (ja) * 2021-09-02 2022-07-29 株式会社寺岡製作所 熱剥離型粘着テープ
CN115216229A (zh) * 2021-04-19 2022-10-21 三星Sdi株式会社 (甲基)丙烯酸类粘合膜、含其的光学构件及光学显示设备

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014051644A (ja) * 2012-08-07 2014-03-20 Nitto Denko Corp 両面粘着シート及び携帯電子機器
JP2015117292A (ja) * 2013-12-18 2015-06-25 日東電工株式会社 粘着剤組成物および粘着テープ
JP2015117293A (ja) * 2013-12-18 2015-06-25 日東電工株式会社 熱拡散材および電子部品
WO2016152787A1 (fr) * 2015-03-24 2016-09-29 デクセリアルズ株式会社 Bande adhésive double face et son procédé de fabrication
KR20200065286A (ko) * 2018-11-30 2020-06-09 주식회사 영우 저밀도 아크릴 폼 점착테이프 및 이의 제조방법
CN115216229A (zh) * 2021-04-19 2022-10-21 三星Sdi株式会社 (甲基)丙烯酸类粘合膜、含其的光学构件及光学显示设备
JP7109698B1 (ja) * 2021-09-02 2022-07-29 株式会社寺岡製作所 熱剥離型粘着テープ

Similar Documents

Publication Publication Date Title
TWI835721B (zh) 黏著片
JP6140491B2 (ja) 両面粘着シート及び携帯電子機器
KR20070012235A (ko) 접착제 조성물, 양면 코팅 접착 시트, 접착 방법 및 휴대용전자 장치
WO2018150859A1 (fr) Feuille stratifiée
US11186750B2 (en) Pressure-sensitive adhesive tape
JP2020105309A (ja) 粘着シート
JP2017149980A (ja) 両面粘着シート及び携帯電子機器
EP2522706A1 (fr) Composition d'adhésif autocollant et feuille adhésive autocollante
JP6003570B2 (ja) 透明粘着剤組成物及び透明粘着テープ
WO2024095322A1 (fr) Composition adhésive, feuille adhésive formée de ladite composition adhésive, et article utilisant ladite feuille adhésive
JP7125259B2 (ja) 粘着シート
WO2022163638A1 (fr) Feuille adhésive optique pour dispositif pliable
CN113597458A (zh) 热剥离型粘着胶带
WO2023276654A1 (fr) Film optique avec film de recouvrement
JP7312299B2 (ja) 粘着テープ
WO2021106350A1 (fr) Ruban adhésif
WO2022163637A1 (fr) Feuille adhésive optique pour dispositif pliable
WO2021215354A1 (fr) Ruban adhésif double face
JP2023095804A (ja) 光学粘着シート
JP2023095055A (ja) カバーフィルム付き光学フィルム
KR20230061258A (ko) 박리 라이너 부착 광학 점착 시트
JP2023095069A (ja) 光学粘着シート
JP2023069650A (ja) はく離ライナー付き光学粘着シート
JP2024067533A (ja) 粘着シート、積層体及び光学デバイス
JP2023137398A (ja) 光学粘着シート

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 22964345

Country of ref document: EP

Kind code of ref document: A1