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WO2025183300A1 - Composition adhésive et film adhésif la comprenant - Google Patents

Composition adhésive et film adhésif la comprenant

Info

Publication number
WO2025183300A1
WO2025183300A1 PCT/KR2024/017457 KR2024017457W WO2025183300A1 WO 2025183300 A1 WO2025183300 A1 WO 2025183300A1 KR 2024017457 W KR2024017457 W KR 2024017457W WO 2025183300 A1 WO2025183300 A1 WO 2025183300A1
Authority
WO
WIPO (PCT)
Prior art keywords
polymer resin
less
acrylate
weight
adhesive
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/KR2024/017457
Other languages
English (en)
Korean (ko)
Inventor
김태근
김장순
이지훈
최준만
이정민
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Toray Advanced Materials Korea Inc
Original Assignee
Toray Advanced Materials Korea Inc
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 Toray Advanced Materials Korea Inc filed Critical Toray Advanced Materials Korea Inc
Publication of WO2025183300A1 publication Critical patent/WO2025183300A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • 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
    • 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
    • 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
    • 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
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • 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

Definitions

  • the present invention relates to an adhesive composition and an adhesive film comprising the same, and more particularly, to an adhesive composition comprising a first polymer resin and a second polymer resin, and having an elastic modulus of 10 9 or less at -20°C and an elastic modulus of 10 6 or less at 20°C, and an adhesive film comprising the same.
  • OCA Optically Clear Adhesive
  • OCAs applied to vehicles have very different required properties compared to OCAs applied to mobile devices.
  • Automotive products have significantly longer replacement cycles than mobile products. Therefore, OCAs used in automotive products must maintain stable properties for a much longer period of time than those used in mobile products.
  • automotive products are often exposed to much higher temperatures than mobile products, are frequently exposed to external light such as ultraviolet rays, and are frequently exposed to conditions where high and low temperatures alternate with seasonal changes.
  • the technical problem to be achieved by the present invention is to provide an adhesive composition having excellent durability and minimizing the occurrence of bubbles and floating by including a first polymer resin and a second polymer resin, and an adhesive film including the same.
  • One embodiment of the present invention provides an adhesive composition comprising a first polymer resin and a second polymer resin, and having an elastic modulus value of 10 9 or less at -20°C and an elastic modulus value of 10 6 or less at 20°C.
  • the first polymer resin and the second polymer resin may be acrylate-based polymer resins.
  • the first polymer resin may be an acrylate-based prepolymer.
  • the second polymer resin may be included in an amount of more than 5 parts by weight and less than 25 parts by weight with respect to 100 parts by weight of the first polymer resin.
  • the weight average molecular weight (Mw) of the first polymer resin may be 500,000 or more and 3.5 million or less.
  • the weight average molecular weight (Mw) of the second polymer resin may be 1,000 or more and 10,000 or less.
  • the gel fraction measured after curing the adhesive composition may be 77% or more.
  • the viscosity measured after curing the adhesive composition may be 2,000 cps or more and 10,000 cps or less.
  • One embodiment of the present invention provides an adhesive film comprising a substrate layer; and an adhesive layer; wherein the adhesive layer comprises a first polymer resin and a second polymer resin.
  • the first polymer resin and the second polymer resin may be acrylate-based polymer resins.
  • the first polymer resin may be an acrylate-based prepolymer.
  • the second polymer resin may be included in an amount of 10 parts by weight or more and 20 parts by weight or less with respect to 100 parts by weight of the first polymer resin.
  • the peeling force of the adhesive film for the substrate may be 2,000 gf/inch or more.
  • the haze of the adhesive layer may be less than 1.0%.
  • the color difference (b*) of the adhesive layer may be less than 0.5.
  • An adhesive composition according to one embodiment of the present invention can have excellent plastic durability and excellent printing step absorption performance by controlling the elastic modulus value.
  • An adhesive film according to one embodiment of the present invention can minimize the occurrence of bubbles and lifting and have excellent plastic durability.
  • a and/or B means “A and B, or A or B.”
  • One embodiment of the present invention includes an adhesive composition comprising a first polymer resin and a second polymer resin, and having an elastic modulus value of 10 9 or less at -20°C and an elastic modulus value of 10 6 or less at 20°C.
  • An adhesive composition according to one embodiment of the present invention can have excellent plastic durability and excellent printing step absorption performance by controlling the elastic modulus value.
  • the elastic modulus value at -20°C of the adhesive composition may be 9.0e +7 or more and 2.0e + 8 or less, 9.0e+ 7 or more and 1.9e +8 or less, 9.0e+7 or more and 1.8e +8 or less, 9.0e+7 or more and 1.7e+8 or less, 9.1e + 7 or more and 1.6e +8 or less, 9.2e + 7 or more and 1.5e +8 or less, 9.3e+7 or more and 1.4e+8 or less, or 9.4e +7 or more and 1.3e +8 or less.
  • the elastic modulus value at 20°C of the adhesive composition may be 1.4e +5 or more and 2.0e +5 or less, 1.4e + 5 or more and 1.9e +5 or less, 1.45e +5 or more and 1.8e +5 or less, or 1.53e +5 or more and 1.73e +5 or less.
  • the first polymer resin and the second polymer resin may be acrylate-based polymer resins.
  • the acrylate polymer resin may be a copolymer of acrylate monomer components.
  • (Meth)acrylic means acrylic and/or methacrylic.
  • the acrylate monomer is, for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, s-butyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, isopentyl (meth)acrylate, neopentyl (meth)acrylate, n-hexyl (meth)acrylate, heptyl (meth)acrylate, ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, nonyl (meth)acrylate, isononyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, undecyl (meth)acryl
  • the acrylate monomer may include, for example, (meth)acrylic acid cycloalkyl esters, (meth)acrylic acid esters having a bicyclic aliphatic hydrocarbon ring, and (meth)acrylic acid esters having three or more aliphatic hydrocarbon rings.
  • the (meth)acrylic acid cycloalkyl esters include cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, cycloheptyl (meth)acrylate, and cyclooctyl (meth)acrylate.
  • Examples of the (meth)acrylic acid esters having a bicyclic aliphatic hydrocarbon ring include isobornyl (meth)acrylate.
  • the acrylate monomer may be a hydroxyl group-containing monomer
  • the hydroxyl group-containing monomer may be, for example, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 10-hydroxydecyl (meth)acrylate, 12-hydroxylauryl (meth)acrylate, and (4-hydroxymethylcyclohexyl)methyl (meth)acrylate.
  • the first polymer resin may be an acrylate-based prepolymer. That is, the first polymer resin may be a partially polymerized acrylate-based polymer resin.
  • the acrylate-based prepolymer may be a partial polymerization of the above-mentioned acrylate-based monomers.
  • the acrylate-based monomer may be at least one selected from the group consisting of ethylhexyl acrylate (EHA), isobornyl acrylate (IBoA), 2-hydroxy ethyl acrylate (HEA), butyl acrylate (BA), cyclohexyl acrylate (CHA), 4-hydroxy butyl acrylate (HBA), and combinations thereof.
  • EHA ethylhexyl acrylate
  • IBoA isobornyl acrylate
  • HSA 2-hydroxy ethyl acrylate
  • BA butyl acrylate
  • CHA cyclohexyl acrylate
  • HBA 4-hydroxy butyl acrylate
  • the second polymer resin may be included in an amount of more than 5 parts by weight and less than 25 parts by weight with respect to 100 parts by weight of the first polymer resin. Specifically, the second polymer resin may be included in an amount of 6 parts by weight or more and 24 parts by weight or less, 7 parts by weight or more and 23 parts by weight or less, 8 parts by weight or more and 22 parts by weight or less, 9 parts by weight or more and 21 parts by weight or less, or 10 parts by weight or more and 20 parts by weight or less with respect to 100 parts by weight of the first polymer resin.
  • the weight average molecular weight (Mw) of the first polymer resin may be 500,000 or more and 3.5 million or less. Specifically, the weight average molecular weight (Mw) of the first polymer resin may be 600,000 or more and 3.45 million or less, 700,000 or more and 3.4 million or less, 800,000 or more and 3.35 million or less, 900,000 or more and 3.3 million or less, 1 million or more and 3.25 million or less, or 1.2 million or more and 3.23 million or less.
  • the viscosity of the first polymer resin may be 5,000 cps or more and 500,000 cps or less. Specifically, the viscosity of the first polymer resin may be 6,000 cps or more and 450,000 cps or less, 7,000 cps or more and 400,000 cps or less, 8,000 cps or more and 350,000 cps or less, 9,000 cps or more and 330,000 cps or less, or 10,000 cps or more and 300,000 cps or less.
  • the weight average molecular weight (Mw) of the second polymer resin may be 1,000 or more and 10,000 or less. Specifically, the weight average molecular weight (Mw) of the second polymer resin may be 2,000 or more and 9,000 or less, 3,000 or more and 8,000 or less, 4,000 or more and 7,000 or less, 4,500 or more and 6,000 or less, or 4,500 or more and 5,500 or less.
  • the weight average molecular weight (Mw) of the second polymer resin may be 1,000 or more and 10,000 or less.
  • the weight average molecular weight (Mw) of the second polymer resin may be 2,000 or more and 9,000 or less, 3,000 or more and 8,000 or less, 4,000 or more and 7,000 or less, 4,500 or more and 6,000 or less, or 4,500 or more and 5,500 or less.
  • the adhesive composition may further comprise a multifunctional crosslinking agent.
  • the adhesive composition can crosslink the acrylate polymer resin, thereby controlling the gel fraction.
  • the multifunctional crosslinking agent may be a multifunctional (meth)acrylate.
  • ester compounds of polyhydric alcohols and (meth)acrylic acid such as (poly)ethylene glycol di(meth)acrylate, (poly)propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, 1,2-ethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, and tetramethylolmethane tri(meth)acrylate; allyl(meth)acrylate; vinyl(meth)acrylate; divinylbenzene
  • the multifunctional crosslinking agent may be included in an amount of 0.05 parts by weight or more and 0.5 parts by weight or less, preferably 0.1 parts by weight or more and 0.3 parts by weight or less, and more preferably 0.2 parts by weight, based on 100 parts by weight of the first polymer resin.
  • the adhesive composition may further include a photoinitiator.
  • a photoinitiator Any photoinitiator that can initiate a polymerization reaction of the adhesive composition through light irradiation or the like may be used.
  • alpha-hydroxyketone compounds e.g., IRGACURE 184, IRGACURE 500, IRGACURE 2959, DAROCUR 1173; Ciba Specialty Chemicals
  • phenylglyoxylate compounds e.g., IRGACURE 754, DAROCUR MBF; Ciba Specialty Chemicals
  • benzyldimethyl ketal compounds e.g., IRGACURE 651; Ciba Specialty Chemicals
  • a-aminoketone compounds e.g., IRGACURE 369, IRGACURE 907, IRGACURE 1300; Ciba Specialty Chemicals
  • Monoacylphosphine compounds MAPO
  • DAROCUR TPO Ciba Specialty Chemicals
  • Bisacylphosphene compounds BAPO
  • IRGACURE 819, IRGACURE 819DW Ciba Specialty Chemicals
  • Phosphine oxide compounds ex. IRGACURE 2100; Ciba Specialty Chemicals
  • Metallocene compounds ex. IRGACURE 784; Ciba Specialty Chemicals
  • Iodonium salts ex. IRGACURE 250; Ciba Specialty Chemicals
  • mixtures of one or more of the above ex.
  • DAROCUR 4265 IRGACURE 2022, IRGACURE 1300, IRGACURE 2005, IRGACURE 2010, IRGACURE 2020; Ciba Specialty Chemicals (manufactured)), etc., and one or more of the above may be used, but are not limited thereto.
  • the photoinitiator may be included in an amount of 0.1 part by weight or more and 0.5 part by weight or less based on 100 parts by weight of the first polymer resin.
  • the amount may be 0.2 part by weight or more and 0.4 part by weight or less, and more preferably, the amount may be 0.3 part by weight.
  • the adhesive composition may further include a coupling agent.
  • the coupling agent can improve the adhesiveness and adhesive stability of the adhesive, thereby improving heat resistance and moisture resistance, and also enhancing adhesive reliability even when left for a long period of time under harsh conditions.
  • the coupling agent may be, for example, gamma-glycidoxypropyl triethoxy silane, gamma-glycidoxypropyl trimethoxy silane, gamma-glycidoxypropyl methyldiethoxy silane, gamma-glycidoxypropyl triethoxy silane, 3-mercaptopropyl trimethoxy silane, vinyltrimethoxysilane, vinyltriethoxy silane, gamma-methacryloxypropyl trimethoxy silane, gamma-methacryloxy propyl triethoxy silane, gamma-aminopropyl trimethoxy silane, gamma-aminopropyl triethoxy silane, 3-isocyanatopropyl triethoxy silane, gamma-acetoacetatepropyl trimethoxysilane, gamma-acetoacetatepropyl triethoxy silane, beta-cyanoacety
  • silane coupling agent having an acetoacetate group or a beta-cyanoacetyl group, but the present invention is not limited thereto.
  • the coupling agent may be included in an amount of 0.05 parts by weight or more and 0.5 parts by weight or less, preferably 0.1 parts by weight or more and 0.3 parts by weight or less, and more preferably 0.2 parts by weight, based on 100 parts by weight of the first polymer resin.
  • the adhesive composition may further include a rust inhibitor.
  • the rust inhibitor is not particularly limited, but examples thereof include amine compounds, benzotriazole-based compounds, and nitrites.
  • examples thereof include ammonium benzoate, ammonium phthalate, ammonium stearate, ammonium palmitate, ammonium oleate, ammonium carbonate, dicyclohexylamine benzoate, urea, urotropin, thiourea, phenyl carbamate, and cyclohexylammonium-N-cyclohexylcarbamate (CHC).
  • the rust inhibitor may be used singly or in combination of two or more.
  • the rust inhibitor be a benzotriazole-based compound, since it can obtain a good balance of adhesive reliability, transparency, and corrosion prevention properties at a high level.
  • the rust inhibitor may be included in an amount of 0.1 part by weight or more and 0.5 part by weight or less, based on 100 parts by weight of the first polymer resin.
  • the amount may be 0.2 part by weight or more and 0.4 part by weight or less, and more preferably, the amount may be 0.3 part by weight.
  • the gel fraction measured after curing the adhesive composition may be 77% or more.
  • the gel fraction measured after curing the adhesive composition may be 77% or more and 95% or less, 77% or more and 94% or less, 77% or more and 92% or less, 77% or more and 90% or less, 77% or more and 88% or less, 77% or more and 86% or less, 77% or more and 84% or less, or 77% or more and 82% or less.
  • the viscosity measured after curing the adhesive composition may be 2,000 cps or more and 10,000 cps or less.
  • the viscosity measured after curing the adhesive composition may be 3,000 cps or more and 9,500 cps or less, 4,000 cps or more and 9,000 cps or less, 5,000 cps or more and 8,500 cps or less, 6,000 cps or more and 8,500 cps or less, 7,000 cps or more and 8,500 cps or less, 7,500 cps or more and 8,400 cps or less, 7,600 cps or more and 8,300 cps or less, 7,700 cps or more and 8,200 cps or less, or 7,900 cps or more and 8,100 cps or less.
  • One embodiment of the present invention includes a substrate layer; and an adhesive layer; wherein the adhesive layer includes an adhesive film including a first polymer resin and a second polymer resin.
  • An adhesive film according to one embodiment of the present invention can minimize the occurrence of bubbles and lifting and have excellent plastic durability.
  • the substrate layer may be a resin film.
  • a plastic material such as a polyester series such as polyethylene terephthalate (PET), a polycarbonate series, a polyolefin series, a polyimide series, etc.
  • the first polymer resin and the second polymer resin may be acrylate-based polymer resins.
  • the first polymer resin may be an acrylate-based prepolymer.
  • the second polymer resin may be included in an amount of 10 parts by weight or more and 20 parts by weight or less with respect to 100 parts by weight of the first polymer resin.
  • the contents of the first polymer resin and the second polymer resin are as described above.
  • the peeling force of the adhesive film with respect to the substrate may be 2,000 gf/inch or more.
  • the peeling force of the adhesive film with respect to the substrate may be 2,000 gf/inch or more and 4,500 gf/inch or less, 2,500 gf/inch or more and 4,400 gf/inch or less, 2,600 gf/inch or more and 4,300 gf/inch or less, or 2,900 gf/inch or more and 4,300 gf/inch or less.
  • the haze of the adhesive layer may be less than 1.0%. Specifically, the haze of the adhesive layer may be 0.3% or more and 0.9% or less, 0.4% or more and 0.8% or less, 0.42% or more and 0.7% or less, 0.44% or more and 0.65% or less, 0.46% or more and 0.6% or less, or 0.47% or more and 0.59% or less.
  • the optical properties can be improved.
  • the color difference (b*) of the adhesive layer may be less than 0.5.
  • the color difference (b*) of the adhesive layer may be 0.15 or more and 0.45 or less, 0.16 or more and 0.43 or less, 0.17 or more and 0.41 or less, 0.18 or more and 0.39 or less, 0.19 or more and 0.37 or less, or 0.20 or more and 0.36 or less.
  • EHA ethylhexyl acrylate
  • IBoA isobornyl acrylate
  • HSA 2-hydroxyethyl acrylate
  • the weight average molecular weight of the partially polymerized acrylate-based polymer resin (A) was 3.23 million.
  • EHA ethylhexyl acrylate
  • NDP N-pyrrolidone
  • HSA 2-hydroxyethyl acrylate
  • B The weight average molecular weight of the partially polymerized acrylate-based polymer resin (B) was 1.2 million.
  • EAc ethyl acetate
  • DCPMA dicyclopentanyl methacrylate
  • MMA methyl methacrylate
  • dodecyl mercaptan dodecyl mercaptan as a molecular weight regulator
  • the manufactured coating solution was coated on a polyethylene terephthalate film (XD500P, Toray Advanced Materials, thickness: 75 ⁇ m) that had been subjected to release treatment using a bar coater so that the film had a thickness of 125 ⁇ m after UV curing. Thereafter, the film was cured by irradiating it with ultraviolet rays using a UV lamp for 5 minutes, thereby manufacturing an adhesive film including an adhesive layer.
  • XD500P polyethylene terephthalate film
  • An adhesive film was manufactured in the same manner as in Example 1, except that the composition of the adhesive composition was changed as shown in Table 1 below.
  • Example 1 A 10 0.2 0.3 0.2 0.3 Example 2 A 20 0.2 0.3 0.2 0.3 Example 3 B 20 0.2 0.3 0.2 0.3 Example 4 C 20 0.2 0.3 0.2 0.3 Comparative Example 1 A 0 0.2 0.3 0.2 0.3 Comparative Example 2 A 5 0.2 0.3 0.2 0.3 Comparative Example 3 A 25 0.2 0.3 0.2 0.3
  • Multifunctional crosslinking agent hexanediol diacrylate (HDDA)
  • Photoinitiator Irgacure 651, Ciba Specialty Chemicals
  • Rust inhibitor benzotriazole, Daemyung Chemical
  • the adhesive films manufactured in the above examples and comparative examples were cut to a size of 3 cm ⁇ 3 cm, attached to a plastic sheet on one side, placed on glass (0.2 T) on the other side, and then laminated by autoclaving (4 bar, 40°C, 20 min). Afterwards, bubbles and lifting were checked after 100 hours under constant temperature and humidity conditions (85°C/85%).
  • Plastic durability performance was evaluated as ⁇ if no bubbles or bulging occurred, and X if bubbles or bulging occurred.
  • the adhesive films manufactured in the above examples and comparative examples were cut to a size of 25 mm ⁇ 20 cm (width ⁇ height), the release film was peeled off, and then attached to stainless steel (SUS 304) by reciprocating a 2 kg roller 5 times. After 20 minutes, the peeling force (gf/inch) was measured using a tensile tester under the conditions of a peeling speed of 300 mm/min and a peeling angle of 180°.
  • the cured product (adhesive) of the adhesive composition manufactured in the above examples and comparative examples was cut into a size of 5 cm ⁇ 5 cm, placed in a polyethylene bottle, and the weight (a) was measured. Then, ethyl acetate was added to the polyethylene bottle so that the adhesive was sufficiently immersed, and left at room temperature for 24 hours. Next, the adhesive and ethyl acetate in the polyethylene bottle were poured onto a wire mesh (weight: b) cut into a size of 14 cm ⁇ 14 cm and filtered. Thereafter, the wire mesh from which the adhesive was filtered was dried in an oven at 110°C for 2 hours, and the weight (c) was measured. Then, the measured weights a, b, and c were substituted into the following general formula 1 to measure the gel fraction (unit: %).
  • the adhesive films of the above examples and comparative examples were attached to a glass substrate having a thickness of 1.1 T using a 2 kg roller, and a glass substrate having a thickness of 0.55 T was laminated thereon. Then, after leaving the specimen in an autoclave at 40°C and 4 bar for 20 minutes, the specimen was placed in an oven at 85°C and 85 RH% relative humidity, and after 3 days (100 hours), the occurrence of white turbidity was visually confirmed.
  • the performance of preventing white turbidity was evaluated as ⁇ if no white turbidity was observed, and X if white turbidity was observed.
  • an adhesive layer having a thickness of about 1 mm was manufactured.
  • the adhesive layer manufactured in the above examples and comparative examples was attached to a 1.1 T glass surface in the form of glass/adhesive layer/glass, and then the transmittance/haze was measured using NDH 5000 (Nippon Denshoku).
  • the color difference (b*) was measured using CM-3600A (Konica minolta).
  • the adhesive layers manufactured in the above examples and comparative examples were laminated on the printed step (black, 70 um) and processed in an autoclave (4 bar, 40°C, 20 min) to perform lamination. Afterwards, bubbles and lifting were confirmed after 100 hours under constant temperature and humidity conditions (85°C/85%).
  • the printing step performance was evaluated as ⁇ if no bubbles or bulging occurred, and X if bubbles or bulging occurred.
  • the adhesive films manufactured in Examples 1 to 4 according to the present invention have a gel fraction of 77% or more, exhibit good plastic durability and printing step performance without bubbles or lifting, and exhibit anti-whitening properties as no whitening occurs in the whitening evaluation.
  • the films exhibit excellent haze and optical properties, confirming their suitability for use as optical adhesive films.
  • the adhesive composition according to one embodiment of the present invention and the adhesive film including the same include the first polymer resin and the second polymer resin, thereby minimizing the occurrence of bubbles and lifting and providing excellent plastic durability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne une composition adhésive et un film adhésif la comprenant, et plus spécifiquement, concerne une composition adhésive et un film adhésif la comprenant, la composition comprenant une première résine polymère et une seconde résine polymère et ayant un module d'élasticité de 109 ou moins à -20 °C et 106 ou moins à 20 °C.
PCT/KR2024/017457 2024-02-28 2024-11-07 Composition adhésive et film adhésif la comprenant Pending WO2025183300A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020240028705A KR20250132036A (ko) 2024-02-28 2024-02-28 점착제 조성물 및 이를 포함하는 점착필름
KR10-2024-0028705 2024-02-28

Publications (1)

Publication Number Publication Date
WO2025183300A1 true WO2025183300A1 (fr) 2025-09-04

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KR20220153961A (ko) * 2021-05-12 2022-11-21 도레이첨단소재 주식회사 점착필름 및 이를 포함하는 플렉시블 디스플레이 소자
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