WO2017145545A1 - Composition d'agent adhésif et ruban adhésif - Google Patents

Composition d'agent adhésif et ruban adhésif Download PDF

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Publication number
WO2017145545A1
WO2017145545A1 PCT/JP2017/000743 JP2017000743W WO2017145545A1 WO 2017145545 A1 WO2017145545 A1 WO 2017145545A1 JP 2017000743 W JP2017000743 W JP 2017000743W WO 2017145545 A1 WO2017145545 A1 WO 2017145545A1
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WIPO (PCT)
Prior art keywords
pressure
sensitive adhesive
group
meth
adhesive tape
Prior art date
Application number
PCT/JP2017/000743
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English (en)
Japanese (ja)
Inventor
靖史 土屋
康史 松澤
Original Assignee
株式会社寺岡製作所
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Filing date
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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 KR1020187026124A priority Critical patent/KR102422205B1/ko
Priority to CN201780013112.2A priority patent/CN108699416B/zh
Priority to JP2018501028A priority patent/JP6548347B2/ja
Publication of WO2017145545A1 publication Critical patent/WO2017145545A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/385—Acrylic polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—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 a pressure-sensitive adhesive composition that does not float or peel off even at high temperatures (for example, 300 ° C.), and that does not cause adhesive residue or contamination on the adherend even after peeling, and a pressure-sensitive adhesive tape using the same About.
  • pressure-sensitive adhesive tapes having an acrylic pressure-sensitive adhesive layer are frequently used in industrial applications such as the electric / electronic field because they are less susceptible to thermal deterioration in a high temperature environment.
  • the adhesive tape may be exposed to a higher temperature environment. Accordingly, there has been a demand for further improving the heat resistance of the acrylic pressure-sensitive adhesive.
  • the adhesive tape in use has a high adhesive force to the adherend.
  • the adhesive tape after use is required to be easily peelable (removability). Therefore, various techniques have been proposed to improve these points.
  • Patent Document 1 describes a heat-peelable thermosetting pressure-sensitive adhesive film in which an acrylic pressure-sensitive adhesive layer contains a thermosetting acrylic pressure-sensitive adhesive polymer having an epoxy group and a carboxyl group in the molecule. And, since the three-dimensional cross-linking is quickly formed between the epoxy group and the carboxyl group by heating and cured, it is explained that the pressure-sensitive adhesive film can be easily peeled off from the adherend by reducing the adhesiveness. ing. Specifically, the heating temperature in the examples is 190 ° C., and it is described that it was able to be peeled easily due to the extremely low adhesive strength by heat curing.
  • Patent Document 2 discloses an adhesive composed of an acrylic pressure-sensitive adhesive (C1) having a mass average molecular weight of 750,000 or more and an acid value of 5 or more and an acrylic pressure-sensitive adhesive (C2) having a mass average molecular weight of less than 400,000 and an acid value of 40 or more.
  • An adhesive body which is a reaction product of an agent component and a crosslinking agent (D) is described.
  • the high molecular weight component (C1) is a component that maintains the peeling force at high temperature by heating due to its cohesive force, and the low molecular weight component (C2) controls the peelability after heating to increase the removability. It is described as an ingredient.
  • the heating temperature is 110 ° C. to 170 ° C.
  • Patent Document 3 states that the adhesive strength to stainless steel after 20 minutes when applied at 23 ° C. is 100 mN / inch or less, and the adhesive strength after heating at 170 ° C. for 1 hour after application is 200 mN / inch or less.
  • An acrylic solvent-type pressure-sensitive adhesive composition containing an acrylic polymer (A) containing no group is described. It is described that it is important that the acrylic polymer (A) does not have a carboxyl group in order to obtain such ultra-adhesive strength.
  • Patent Document 4 discloses an adhesive comprising an acrylic resin, a crosslinking agent for crosslinking the acrylic resin, a photocurable resin, and a photocuring agent for curing the photocurable resin.
  • a composition is described.
  • This pressure-sensitive adhesive composition has a low initial adhesive strength and can be easily re-applied, and does not float or peel off after being bonded to an adherend and is placed in a high-temperature environment. However, it is described that the adhesive force does not change, and the adhesive residue and adherend contamination can be reduced.
  • the heating temperature in the examples is 230 ° C.
  • Patent Document 5 discloses an acrylic ester and / or a methacrylic ester, a primary hydroxyl group-containing monomer having a primary hydroxyl group in the molecule, a secondary hydroxyl group-containing monomer having a secondary hydroxyl group in the molecule, and / or A pressure-sensitive adhesive composition is described which contains a copolymer polymer which is at least copolymerized with a tertiary hydroxyl group-containing monomer having a tertiary hydroxyl group and is crosslinked with a crosslinking agent.
  • the degree of crosslinking of the pressure-sensitive adhesive composition can be increased, heat resistance and heat-and-moisture resistance can be improved, and 2 in the molecule. It has been described that reworkability can be ensured by adding a secondary hydroxyl group-containing monomer having a secondary hydroxyl group and / or a tertiary hydroxyl group-containing monomer having a tertiary hydroxyl group.
  • the heating temperature in the examples is 80 ° C.
  • Patent Document 6 has 3 or more carbon atoms.
  • a pressure-sensitive adhesive comprising a hydroxyalkyl (meth) acrylate (a-2-1) in which a hydroxyl group is bonded to an alkyl group and a hydroxyl group-containing (meth) acrylate having a hydroxyl group bonded to an alkyl group shorter than (a-2-1) A composition is described.
  • the temperature of the heating process has been increasing more and more, for example, the number of processes for performing heat treatment at a high temperature of 300 ° C. for a short time has begun to increase.
  • the pressure-sensitive adhesive composition or pressure-sensitive adhesive tape described in Patent Documents 1 to 5 has a heat resistance verification temperature of 230 ° C. at most, and both heat resistance and re-peelability even at higher temperatures (eg, 300 ° C.).
  • the recent demand for excellence cannot be fully met.
  • the pressure-sensitive adhesive composition described in Patent Document 6 is not intended to improve heat resistance and uses only a small amount of an isocyanate curing agent, it is considered that the heat resistance is not sufficient.
  • JP 2003-238910 A JP 2003-292931 A JP 2004-217740 A International Publication No. 2015/119042 JP 2009-29948 A JP 2014-108968 A
  • the object of the present invention is to have a sufficient initial adhesive force, and does not float or peel even at high temperatures (for example, 300 ° C.). Even if it is peeled off after heating, adhesive residue or contamination is generated on the adherend. It is providing the adhesive composition which does not, and an adhesive tape using the same.
  • the present invention relates to a monomer unit derived from two or more kinds of hydroxyl group-containing (meth) acrylate monomers represented by the following formulas (A1) and (A2), and 5.1 to 20% by mass of a carboxyl group-containing monomer.
  • R 1 and R 2 are hydrocarbon groups or oxygen atom-containing hydrocarbon groups, R 2 has more carbon atoms than R 1 , and R 3 is a hydrogen atom or methyl. And x is 1 to 3), and an epoxy-based crosslinking agent (B) Is a pressure-sensitive adhesive composition containing
  • this invention is an adhesive tape which has an adhesive layer formed from the said adhesive composition.
  • the present invention since it contains a (meth) acrylic polymer (A) having a specific copolymer composition and an epoxy-based crosslinking agent (B), it has a sufficient initial adhesive force and, for example, a general acrylic of 300 ° C.
  • a pressure-sensitive adhesive composition that does not float or peel even at high temperatures far exceeding the decomposition temperature of the polymer, and does not cause adhesive residue or contamination on the adherend even if peeled after heating, and a pressure-sensitive adhesive tape using the same Can provide.
  • the pressure-sensitive adhesive composition of the present invention is a composition containing a (meth) acrylic polymer (A) and an epoxy-based crosslinking agent (B).
  • the (meth) acrylic polymer (A) used in the pressure-sensitive adhesive composition is a monomer unit derived from two or more hydroxyl group-containing (meth) acrylate monomers represented by the following formulas (A1) and (A2): And at least a monomer unit derived from the carboxyl group-containing monomer (A3).
  • the hydroxyl group-containing (meth) acrylate monomer represented by the formula (A1) is referred to as “hydroxyl group-containing short chain monomer (A1)”
  • the hydroxyl group-containing (meth) acrylate monomer represented by the formula (A2) This is referred to as “hydroxyl-containing long-chain monomer (A2)”.
  • R 1 and R 2 are hydrocarbon groups or oxygen atom-containing hydrocarbon groups, R 2 has more carbon atoms than R 1 , and R 3 is a hydrogen atom or methyl. And x is 1 to 3.
  • the heat resistance excellent in the adhesive composition is provided by using together a hydroxyl-containing short chain monomer (A1) and a hydroxyl-containing long chain monomer (A2). The reason is not necessarily clear.
  • the monomer unit derived from the hydroxyl group-containing short chain monomer (A1) is difficult to thermally decompose
  • the monomer unit derived from the hydroxyl group-containing long chain monomer (A2) is initially Contributes to the improvement of adhesive strength and also contributes to the improvement of heat resistance by entanglement of the long chain R 2 , and the cross-linking reaction occurs in a stepwise manner, and both the above-mentioned actions synergistically provide an appropriate adhesive strength even after high-temperature heating. This is presumed to be due to the fact that
  • R 1 and R 2 of the hydroxyl group-containing short chain monomer (A1) and the hydroxyl group-containing long chain monomer (A2) may be any hydrocarbon group or oxygen atom-containing hydrocarbon group, and the kind thereof is not particularly limited. Either saturated or unsaturated may be used, but a saturated hydrocarbon group and an oxygen atom-containing saturated hydrocarbon group are preferred. Moreover, although aliphatic and aromatic may be sufficient, an aliphatic hydrocarbon group and an oxygen atom containing aliphatic saturated hydrocarbon group are preferable. Further, in the case of an aliphatic group, it may be any of linear, branched, and alicyclic.
  • a linear or branched aliphatic hydrocarbon group and an oxygen atom-containing linear or branched aliphatic hydrocarbon group are preferred, and a linear aliphatic hydrocarbon group and an oxygen atom-containing linear aliphatic hydrocarbon group Is more preferable.
  • R 1 and R 2 of the hydroxyl group-containing short chain monomer (A1) and the hydroxyl group-containing long chain monomer (A2) are hydrocarbon groups, —R 1 — (OH) x and —R 2 — (OH) x (ie, Specific examples of the hydrocarbon group having a hydroxyl group include a hydroxyethyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 2-hydroxy-1-methylethyl group, a 2-hydroxybutyl group, and a 3-hydroxybutyl group.
  • 4-hydroxybutyl group 2-hydroxy-1,1-dimethylethyl group, 3-hydroxy-2-methylpropyl group, 2-hydroxy-2-methylpropyl group, 1- (hydroxymethyl) propyl group, 2- Hydroxy-1-methylpropyl group, 3-hydroxy-1-methylpropyl group, 2-hydroxypentyl group, 5-hydroxypentyl group, 2,2 Dimethyl-3-hydroxypropyl group, 3-methyl-3-hydroxybutyl group, 2-hydroxyhexyl group, 6-hydroxyhexyl group, 2-hydroxyheptyl group, 7-hydroxyhexyl group, 2-hydroxyoctyl group, 8- Examples thereof include unsaturated aliphatic hydrocarbon groups having a hydroxyl group such as a hydroxyoctyl group and a 10-hydroxydecyl group.
  • R 1 and R 2 of the hydroxyl group-containing short chain monomer (A1) and the hydroxyl group-containing long chain monomer (A2) are oxygen atom-containing hydrocarbon groups
  • Specific examples of x include groups represented by — (OR) n—OH (for example, polyalkylene glycol such as polyethylene glycol group, polypropylene glycol group, polybutylene glycol group).
  • the number of carbon atoms of R 2 of the hydroxyl group-containing long chain monomer (A2) is larger than the number of carbon atoms of R 1 of the hydroxyl group-containing short chain monomer (A1).
  • the difference between the number of carbon atoms of R 2 and the number of carbon atoms of R 1 is 1 or more, preferably 2 or more, more preferably 2 or more and 8 or less.
  • this difference is 2 or more, a more remarkable effect can be obtained in terms of heat resistance (for example, improvement of adhesive strength after heating, prevention of occurrence of lifting). This is presumed to be because the molecular chain becomes more entangled.
  • the number of carbon atoms in R2 of the hydroxyl group-containing long chain monomer (A2) is appropriately large.
  • the ratio of the amount of hydroxyl group to the amount of R 2 is relatively undesirably lowered.
  • the number of carbon atoms in R 2 of the hydroxyl group-containing long chain monomer (A2) is 2 or more, preferably 3 or more, more preferably 4 or more and 12 or less.
  • the number of carbon atoms of R 1 in the hydroxyl group-containing short chain monomer (A1) is 1 or more, preferably 1 or more and 4 or less, more preferably 2 or more and 3 or less.
  • Each R 3 in the hydroxyl group-containing short chain monomer (A1) and the hydroxyl group-containing long chain monomer (A2) is a hydrogen atom or a methyl group.
  • R 3 and R 3 of the hydroxyl group-containing long-chain monomer (A2) of the hydroxyl group-containing short chain monomer (A1) may be mutually the same or may be different.
  • X in the hydroxyl group-containing short chain monomer (A1) and the hydroxyl group-containing long chain monomer (A2) represents the number of hydroxyl groups (OH) bonded to R 1 and R 2 .
  • x is 1 to 3, preferably 1 to 2, and most preferably 1.
  • X of the hydroxyl group-containing short chain monomer (A1) and x of the hydroxyl group-containing long chain monomer (A2) may be the same or different.
  • the bonding position of — (OH) to R 1 and R 2 of the hydroxyl group-containing short chain monomer (A1) and the hydroxyl group-containing long chain monomer (A2) is not particularly limited. However, regarding the bonding position of — (OH) to R 2 of the hydroxyl group-containing long-chain monomer (A2), the molecular end side of R 2 (end far from the (meth) acryloyl group) is preferable.
  • hydroxyl group-containing short chain monomer (A1) and the hydroxyl group-containing long chain monomer (A2) include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 3-hydroxypropyl (meta).
  • the monomer unit derived from the hydroxyl group-containing short chain monomer (A1) and the single unit derived from the hydroxyl group-containing long chain monomer (A2) The total content of body units is preferably 5 to 20% by mass, more preferably 10 to 15% by mass. Further, the content of the monomer unit resulting from the hydroxyl group-containing long chain monomer (A2) is preferably larger than the content of the monomer unit resulting from the hydroxyl group-containing short chain monomer (A1). Thereby, a more remarkable effect is obtained in terms of heat resistance (for example, improvement of adhesive strength after heating, prevention of occurrence of floating).
  • the blending ratio (A1 / A2) of both monomer units is preferably 49/51 to 30/70, more preferably 45/55 to 35/65.
  • the carboxyl group-containing monomer (A3) is a component that improves the physical properties such as cohesive force through a crosslinking reaction with the epoxy-based crosslinking agent (B), and can thereby suppress adhesive residue during re-peeling.
  • the carboxyl group-containing monomer (A3) is not particularly limited as long as it is a compound having a carboxyl group (acidic group) and an unsaturated double bond.
  • monoacrylate for example, Toagosei Co., Ltd., trade name M-5300
  • phthalic acid monohydroxyethyl acrylate for example, Toagosei Co., Ltd., trade name M-5400
  • An acrylic acid dimer
  • carboxyl group-containing monomers (A3) Two or more kinds may be used in combination.
  • (meth) acrylic monomers that is, monomers having a (meth) acryloyl group
  • acrylic acid and methacrylic acid are particularly preferable.
  • the content of the monomer unit resulting from the carboxyl group-containing monomer (A3) is 5.1 to 20% by mass or less, The amount is preferably 7 to 18% by mass, more preferably 9 to 16% by mass.
  • (Meth) acrylic polymer (A) may contain monomer units derived from other monomers than the above-described monomers.
  • a (meth) acrylate monomer containing no hydroxyl group or carboxyl group is preferable, an alkyl (meth) acrylate monomer is more preferable, and an alkyl (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms is particularly preferable. preferable.
  • Monomer derived from (meth) acrylate monomer (more preferably alkyl (meth) acrylate monomer) containing no hydroxyl group or carboxyl group in 100% by mass of monomer units constituting (meth) acrylic polymer (A).
  • the unit content is preferably 60 to 90% by mass, more preferably 70 to 85% by mass.
  • (Meth) acrylic polymer (A) can be obtained by copolymerizing the components described above.
  • the polymerization method is not particularly limited, and various known methods can be used, but radical solution polymerization is particularly preferable.
  • the radical solution polymerization is generally performed in a nitrogen atmosphere using a polymerization initiator based on an azo compound or a peroxide.
  • the polymerization temperature is usually about 60 to 80 ° C., and the polymerization time is usually about 5 to 10 hours.
  • the epoxy-based crosslinking agent (B) used in the pressure-sensitive adhesive composition is a component that improves the cohesive strength of the pressure-sensitive adhesive composition by crosslinking reaction with the carboxyl group and / or hydroxyl group of the (meth) acrylic polymer (A). .
  • the epoxy-based crosslinking agent (B) greatly contributes to the improvement of heat resistance. The reason is not necessarily clear. For example, even if the (meth) acrylic polymer (A) contains many functional groups such as a carboxyl group and a hydroxyl group, the site in the molecule that is easily thermally decomposed is an epoxy crosslinking agent. It is speculated that this is due to being capped with (B) and difficult to thermally decompose.
  • the pressure-sensitive adhesive composition tends to gel before coating. Application to the substrate becomes difficult.
  • epoxy-based crosslinking agent (B) examples include ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether, 1,6-hexanediol diglycidyl ether, trimethylolpropane triglycidyl.
  • examples include ether, diglycidylaniline, N, N, N ′, N′-tetraglycidyl-m-xylylenediamine, 1,3-bis (N, N′-diglycidylaminomethyl) cyclohexane.
  • Two or more types of epoxy crosslinking agents (B) may be used in combination.
  • the content of the epoxy-based crosslinking agent (B) is preferably 5 to 25 parts by mass, more preferably 7 to 18 parts by mass, particularly preferably 8 to 15 parts per 100 parts by mass of the (meth) acrylic polymer (A). Part by mass.
  • the pressure-sensitive adhesive composition may contain any resin component other than the (meth) acrylic polymer (A) within a range not impairing the effects of the present invention.
  • the other additive component may be included as needed.
  • Specific examples of the additive component include a solvent, an antioxidant, an ultraviolet absorber, a light stabilizer, an antistatic agent, a filler, and a pigment.
  • the pressure-sensitive adhesive tape of the present invention has a pressure-sensitive adhesive layer formed by the pressure-sensitive adhesive composition of the present invention described above.
  • an adhesive tape has a base material and an adhesive layer on at least one surface of the base material.
  • the pressure-sensitive adhesive tape of the present invention is not limited thereto, and may be, for example, a baseless type pressure-sensitive adhesive tape having no base material.
  • the thickness of the pressure-sensitive adhesive layer in the pressure-sensitive adhesive tape having a substrate is preferably 2 to 100 ⁇ m, more preferably 3 to 80 ⁇ m, and particularly preferably 4 to 70 ⁇ m. The same applies to the thickness of the adhesive layer in the baseless type adhesive tape.
  • the pressure-sensitive adhesive layer in the pressure-sensitive adhesive tape can be formed by crosslinking reaction of the pressure-sensitive adhesive composition of the present invention.
  • the pressure-sensitive adhesive composition can be applied on a substrate and subjected to a crosslinking reaction by heating to form a pressure-sensitive adhesive layer on the substrate.
  • an adhesive composition is apply
  • a coating device such as a roll coater, a die coater, or a lip coater can be used.
  • the solvent in the pressure-sensitive adhesive composition can be removed together with the crosslinking reaction by heating.
  • the type of base material used for the adhesive tape is not particularly limited, and may be appropriately selected according to the performance (heat resistance, etc.) required during use.
  • a known resin substrate such as polyethylene terephthalate (PET) may be used.
  • PET polyethylene terephthalate
  • a resin base material excellent in heat resistance is preferable, specifically, a resin selected from the group consisting of polyphenylene sulfide, polyether imide, polyether ether ketone and polyimide.
  • a constructed substrate is preferred.
  • the base material comprised with a polyimide is especially preferable.
  • the thickness of the substrate is preferably 12.5 to 125 ⁇ m, more preferably 17.5 to 50 ⁇ m.
  • the pressure-sensitive adhesive layer may be formed only on one side of the substrate, or may be formed on both sides to form a double-sided pressure-sensitive adhesive tape.
  • the pressure-sensitive adhesive tape of the present invention preferably has an appropriate pressure-sensitive adhesive force at the time of re-peeling after heating.
  • This can be specified by, for example, the adhesive strength of the adhesive tape after heating at 300 ° C. for 2 hours.
  • the adhesive strength of the adhesive tape in accordance with JIS Z 0237 (2000) is It is preferably 0.03 to 1.5 N / 10 mm, more preferably 0.05 to 1.0 N / 10 mm, and particularly preferably 0.1 to 0.4 N / 10 mm. Details of the measurement conditions are described in the column of Examples.
  • part means “part by mass”.
  • Adhesive strength after heating at 300 ° C The adhesive tape was cut into a width of 10 mm to obtain a test piece. This test piece was bonded to a SUS plate, left in an oven at 300 ° C. for 2 hours, and then allowed to stand at room temperature (23 ° C.) for 2 hours. Then, according to JIS Z 0237 (2000) (adhesive tape / adhesive sheet test method), the adhesive strength was measured under the conditions of a peeling angle of 180 degrees and a peeling speed of 300 mm / min.
  • HSA 2-hydroxyethyl acrylate
  • 4-HBA 4-hydroxybutyl acrylate
  • AE-200 polyethylene glycol monoacrylate (Blenmer (registered trademark) AE-200 manufactured by NOF CORPORATION)
  • AA acrylic acid
  • 2-EHA 2-ethylhexyl acrylate
  • MA methyl acrylate
  • the adhesive tapes of Examples 1 to 3 are the same adhesive tape except that the thickness of the adhesive layer is different. Since the pressure-sensitive adhesive tape of Example 2 had a thick pressure-sensitive adhesive layer, the initial adhesive force was considerably higher than those of the other examples (Examples 1 and 3). However, the adhesive strength after heating at 300 ° C. was the same level as in the other examples. The pressure-sensitive adhesive tape of Example 3 had a slightly thin pressure-sensitive adhesive layer, but the adhesive strength after heating at 300 ° C. was at the same level as other examples. From these results, it can be understood that the thickness of the pressure-sensitive adhesive layer hardly affects the adhesive strength after heating at 300 ° C.
  • the adhesive tapes of Examples 4 to 6 are adhesive tapes in which the amount of each monomer other than 2-EHA is increased.
  • the adhesive tapes of Examples 4 to 6 had a lower initial adhesive force than that of Example 1 because the amount of monomer having a relatively high Tg was large.
  • the adhesive strength after heating at 300 ° C. was at a level with no problem. From these results, it can be understood that the increase in the monomer having a relatively high Tg does not significantly affect the adhesive strength after heating at 300 ° C.
  • the pressure-sensitive adhesive tape of Comparative Example 1 is a pressure-sensitive adhesive tape that uses only one type of long-chain monomer (4-HBA) as a hydroxyl group-containing (meth) acrylate monomer.
  • the pressure-sensitive adhesive strength is too low after heating at 300 ° C. Occurred. This is presumably due to the fact that when only one type of long-chain monomer (4-HBA) is used, the entanglement of the molecular chains is insufficient and thermal decomposition is easy.
  • the pressure-sensitive adhesive tape of Comparative Example 2 was a pressure-sensitive adhesive tape with too little content of the carboxyl group-containing monomer (A3), and adhesive residue was generated at the time of peeling after heating. This is presumed to be due to the fact that the strength of the crosslinked structure was lowered because the crosslinking density was low.
  • the pressure-sensitive adhesive composition of the present invention and the pressure-sensitive adhesive tape using the same are excellent in initial adhesive strength and have heat resistance and removability that can be used even at a high temperature of 300 ° C., so these characteristics are required.
  • Useful for any application For example, it can be suitably used in a manufacturing process that requires a heat treatment process at a high temperature, such as a component-embedded substrate, a glass substrate, a sensor, or a semiconductor.

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

Abstract

La présente invention concerne : une composition d'agent adhésif contenant un polymère méthacrylique (A) comprenant un motif monomère qui représente au moins deux types de monomères de méthacrylate contenant un groupe hydroxy représentés par les formules (A1) et (A2), et 5,1 à 20 % en masse d'un motif monomère qui est un monomère contenant un groupe carboxyle (A3), et un agent de réticulation époxy (B) ; et un ruban adhésif utilisant la composition d'agent adhésif (R1 et R2, chacun représentant un groupe hydrocarbure ou un groupe hydrocarbure contenant des atomes d'oxygène, le nombre d'atomes de carbone dans R2 étant supérieur au nombre d'atomes de carbone dans R1, R3 représentant un atome d'hydrogène ou un groupe méthyle, et x représentant 1-3).
PCT/JP2017/000743 2016-02-25 2017-01-12 Composition d'agent adhésif et ruban adhésif WO2017145545A1 (fr)

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CN201780013112.2A CN108699416B (zh) 2016-02-25 2017-01-12 粘着剂组合物及粘胶带
JP2018501028A JP6548347B2 (ja) 2016-02-25 2017-01-12 粘着剤組成物及び粘着テープ

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TW (1) TWI712668B (fr)
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JP2020045444A (ja) * 2018-09-20 2020-03-26 東洋インキＳｃホールディングス株式会社 粘着剤および粘着シート
JP2021088646A (ja) * 2019-12-03 2021-06-10 信越ポリマー株式会社 制電粘着テープ

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CN108699416A (zh) 2018-10-23
TWI712668B (zh) 2020-12-11
CN108699416B (zh) 2023-10-20
JP6548347B2 (ja) 2019-07-24
KR102422205B1 (ko) 2022-07-18
TW201800523A (zh) 2018-01-01
KR20180107252A (ko) 2018-10-01

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