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
  • C09J201/00—Adhesives based on unspecified macromolecular compounds
• • 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
  • 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
  • C09J133/04—Homopolymers or copolymers of 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
  • 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
  • C09J7/00—Adhesives in the form of films or foils
  • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J7/00—Adhesives in the form of films or foils
  • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
  • C09J7/35—Heat-activated
• • 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
  • C09J2301/304—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 heat-activatable, i.e. not 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
  • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
• • 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
  • C09J2301/50—Additional features of adhesives in the form of films or foils characterized by process specific features
  • C09J2301/502—Additional features of adhesives in the form of films or foils characterized by process specific features process for debonding adherents
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J2433/00—Presence of (meth)acrylic polymer

Definitions

• the present invention relates to a temperature-sensitive adhesive and a temperature-sensitive adhesive tape that exhibit adhesive strength at a predetermined temperature.
• the temperature-sensitive adhesive contains a side chain crystalline polymer, and when the heat treatment is performed to a temperature equal to or higher than the melting point of the side chain crystalline polymer, the side chain crystalline polymer exhibits fluidity. Expresses adhesive strength.
• the temperature-sensitive adhesive tape which is one usage form of the temperature-sensitive adhesive, can be used for the production of flat display devices such as liquid crystal display devices and organic light-emitting display devices described in Patent Document 2, for example.
• a flexible substrate is fixed on a support via a temperature-sensitive adhesive tape provided with a pressure-sensitive adhesive layer made of a temperature-sensitive adhesive on both surfaces of a base film.
• This fixing is performed by heating the pressure-sensitive adhesive layer to a temperature equal to or higher than the melting point of the side chain crystalline polymer to develop an adhesive force.
• a predetermined thin film pattern is formed on the surface of the fixed flexible substrate.
• the pressure-sensitive adhesive layer is cooled to a temperature lower than the melting point of the side chain crystalline polymer to reduce the adhesive force, and the flexible substrate is peeled from the support.
• the conventional temperature-sensitive adhesive as described in Patent Document 1 has a problem that the adhesive strength is reduced in a high-temperature atmosphere (for example, around 150 ° C.). Therefore, in a temperature-sensitive adhesive tape using a conventional temperature-sensitive adhesive, in a process under a high-temperature atmosphere, warpage caused by a difference in thermal expansion between the flexible substrate and the support, and moisture in the adhesive layer -It cannot cope with warpage, floating stress, etc. due to volatilization of residual solvent and the like, and peeling occurs between the adhesive layer and the flexible substrate. Therefore, a temperature-sensitive adhesive and a temperature-sensitive adhesive tape excellent in heat resistance that can maintain high adhesive force even in a high-temperature atmosphere have been demanded.
• An object of the present invention is to provide a temperature-sensitive adhesive and a temperature-sensitive adhesive tape having high heat resistance.
• the present inventors have found the following knowledge. That is, in order to improve the heat resistance of the temperature-sensitive adhesive, it is considered that the crosslinking reaction is performed by adding a crosslinking agent after polymerizing the monomers constituting the side chain crystalline polymer.
• the side chain crystalline polymer and the metal chelate compound form a coordinate bond.
• the coordination bond has a high degree of freedom and is easy to flow as compared with a covalent bond. This tendency is more remarkable under a high temperature atmosphere.
• the fluidity contributes to the hardness of the side chain crystalline polymer, and the hardness contributes to the adhesive strength.
• the softer the side chain crystalline polymer the higher the adhesive force, and therefore the side chain crystalline polymer crosslinked with the metal chelate compound can exhibit sufficient adhesive force.
• high heat resistance can be obtained without lowering the molecular weight or reducing the cohesive force caused by reducing the cross-linking bond such as the covalent bond.
• the temperature-sensitive adhesive of the present invention contains a side chain crystalline polymer and exhibits adhesive strength at a temperature equal to or higher than the melting point of the side chain crystalline polymer.
• the side chain crystalline polymer is composed of a crosslinked polymer obtained by adding a metal chelate compound to the side chain crystalline polymer and performing a crosslinking reaction.
• the temperature-sensitive adhesive tape of the present invention is formed by providing an adhesive layer composed of the temperature-sensitive adhesive on one side or both sides of a base film.
• the present invention since high heat resistance can be exhibited, it is assumed that some stress (for example, external stress, stress due to thermal deformation of a fixing member / component, etc.) is received during processing of the component in a high temperature atmosphere. Are difficult to peel off, and the parts can be securely fixed. In addition, when peeling from the part, the pressure-sensitive adhesive or pressure-sensitive adhesive layer is cooled to a temperature below the melting point of the side-chain crystalline polymer, so that the adhesive strength is reduced. it can.
• some stress for example, external stress, stress due to thermal deformation of a fixing member / component, etc.
• the pressure-sensitive adhesive according to the present invention is a temperature-sensitive pressure-sensitive adhesive.
• the temperature-sensitive pressure-sensitive adhesive means a pressure-sensitive adhesive whose adhesive force changes in response to a temperature change.
• the temperature-sensitive adhesive of the present invention contains a side chain crystalline polymer.
• the side-chain crystalline polymer is crystallized at a temperature lower than the melting point, and exhibits a fluidity by phase transition at a temperature higher than the melting point. That is, the side chain crystalline polymer reversibly causes a crystalline state and a fluid state in response to a temperature change.
• the temperature-sensitive pressure-sensitive adhesive contains a side-chain crystalline polymer in such a ratio that the adhesive strength is exhibited when the side-chain crystalline polymer exhibits fluidity at a temperature equal to or higher than the melting point. That is, the thermosensitive adhesive contains the side chain crystalline polymer as a main component.
• the side-chain crystalline polymer exhibits fluidity, thereby causing adhesive strength. Is expressed.
• the temperature sensitive adhesive is cooled to a temperature lower than the melting point of the side chain crystalline polymer when peeling from the part, the side chain crystalline polymer is crystallized to reduce the adhesive force. .
• the melting point means a temperature at which a specific portion of the polymer that is initially aligned in an ordered arrangement becomes disordered by an equilibrium process.
• the melting point is 20 ° C. or higher, preferably 20 to 60 ° C.
• the crystallization temperature (peeling temperature) is preferably a melting point of ⁇ 15 ° C. or lower.
• the melting point and crystallization temperature are values obtained by measurement under a measurement condition of 10 ° C./min with a differential thermal scanning calorimeter (DSC).
• DSC differential thermal scanning calorimeter
• composition of the side chain crystalline polymer examples include (meth) acrylate having a linear alkyl group having 16 or more carbon atoms, (meth) acrylate having an alkyl group having 1 to 6 carbon atoms, and a polar monomer (crosslinking).
• a copolymer obtained by polymerizing the component) is preferred.
• the polymerization ratio for example, 20 to 80 parts by weight of (meth) acrylate having a linear alkyl group having 16 or more carbon atoms, 20 to 80 parts by weight of (meth) acrylate having an alkyl group having 1 to 6 carbon atoms,
• the polar monomer is preferably 1 to 10 parts by weight.
• Examples of the (meth) acrylate having a linear alkyl group having 16 or more carbon atoms include 16 to 16 carbon atoms such as cetyl (meth) acrylate, stearyl (meth) acrylate, eicosyl (meth) acrylate, and behenyl (meth) acrylate.
• Examples of the (meth) acrylate having 22 linear alkyl groups include (meth) acrylate having an alkyl group having 1 to 6 carbon atoms, such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) ) Acrylate, hexyl (meth) acrylate and the like.
• Examples of the polar monomer include carboxyl group-containing ethylenically unsaturated monomers such as acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid and fumaric acid; 2 -Hydroxyethyl (meth) acrylate, 2 Hydroxypropyl (meth) acrylate, 2-hydroxyhexyl (meth) ethylenically unsaturated monomer having a hydroxyl group such as acrylate and the like, which may be used alone or in combination.
• carboxyl group-containing ethylenically unsaturated monomers such as acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid and fumaric acid
• 2 -Hydroxyethyl (meth) acrylate 2 Hydroxypropyl (meth) acrylate
• a specific composition of the side chain crystalline polymer is, for example, a copolymer obtained by polymerizing 30 to 50 parts by weight of stearyl acrylate, 50 to 70 parts by weight of methyl acrylate, and 1 to 10 parts by weight of acrylic acid.
• examples thereof include a copolymer, a copolymer obtained by polymerizing 30 to 50 parts by weight of behenyl acrylate, 50 to 70 parts by weight of methyl acrylate, and 1 to 10 parts by weight of acrylic acid.
• the polymerization method is not particularly limited, and examples thereof include a solution polymerization method, a bulk polymerization method, a suspension polymerization method, and an emulsion polymerization method.
• the monomer can be polymerized by mixing the monomer exemplified above in a solvent and stirring at about 40 to 90 ° C. for about 2 to 6 hours.
• the weight average molecular weight of the side chain crystalline polymer is 200,000 to 1,000,000, preferably 400,000 to 800,000. If the weight average molecular weight is too small, when the temperature-sensitive adhesive is peeled from the part, the adhesive may remain on the part, so-called adhesive residue may increase. On the other hand, if the weight average molecular weight is too large, the side chain crystalline polymer is less likely to exhibit fluidity even when heated to a temperature equal to or higher than the melting point, so that it is difficult to develop adhesive force.
• the weight average molecular weight is a value obtained by measuring a side chain crystalline polymer by gel permeation chromatography (GPC) and converting the obtained measurement value to polystyrene.
• the side chain crystalline polymer of the present invention comprises a crosslinked polymer obtained by adding a metal chelate compound to the side chain crystalline polymer and performing a crosslinking reaction.
• metal chelate compounds include acetylacetone coordination compounds of polyvalent metals, acetoacetate coordination compounds of polyvalent metals, etc.
• examples of the polyvalent metals include aluminum, nickel, chromium, iron, titanium, Zinc, cobalt, manganese, zirconium and the like can be mentioned, and these may be used alone or in combination.
• aluminum acetylacetone coordination compound or acetoacetate coordination compound is preferred, and aluminum trisacetylacetonate is preferred.
• the amount of the metal chelate compound added is 0.1 to 30% by weight, preferably 1 to 15% by weight, based on the total amount of the side chain crystalline polymer. If the addition amount is too small, the crosslinking is not sufficient, the cohesive force is lowered, and there is a possibility that an adhesive residue is generated at the time of peeling. Moreover, when there is too much said addition amount, the reaction site
• the cross-linking reaction can be performed, for example, as follows. First, the monomer constituting the side chain crystalline polymer is polymerized to obtain a copolymer, and a solvent is added to the copolymer to obtain a copolymer solution. Then, after adding a metal chelate compound to the copolymer solution, it may be heated and dried. As conditions for the heat drying, the temperature is about 90 to 110 ° C., and the time is about 1 to 20 minutes.
• thermosensitive adhesive of the present invention is not particularly limited.
• the copolymer solution to which the metal chelate compound is added is applied to one side or both sides of the base film and dried by heating.
• the adhesive layer which consists of the said thermosensitive adhesive can be provided in the single side
• the copolymer solution may be directly applied to the adherend and dried by heating.
• the copolymer solution is applied to the surface of a base film that has been subjected to a surface release treatment with silicon, fluorine, or the like, and dried by heating to form a temperature-sensitive adhesive layer. If the temperature-sensitive adhesive layer is peeled from the substrate film at the time of use, the temperature-sensitive adhesive can be used as a substrate-less temperature-sensitive adhesive layer.
• the base film examples include synthetic resins such as polyethylene, polyethylene terephthalate, polypropylene, polyester, polyamide, polyimide, polycarbonate, ethylene vinyl acetate copolymer, ethylene ethyl acrylate copolymer, ethylene polypropylene copolymer, and polyvinyl chloride.
• a film is mentioned.
• the film may be a single layer or a multilayer of these, and the thickness is usually about 25 to 250 ⁇ m.
• the surface of the base film may be subjected to surface treatment such as corona discharge treatment, plasma treatment, blast treatment, chemical etching treatment, and primer treatment.
• surface release treatment such as silicon treatment or fluorine treatment may be performed on the surface of the base film.
• the coating can be generally performed with a knife coater, a roll coater, a calendar coater, a comma coater, or the like. Further, depending on the coating thickness and the viscosity of the copolymer solution, a gravure coater, a rod coater or the like can be used.
• the thickness of the thermosensitive pressure-sensitive adhesive layer containing no substrate is 5 to 60 ⁇ m, preferably 5 to 50 ⁇ m, more preferably 5 to 40 ⁇ m.
• a flexible substrate is fixed on a support through a temperature-sensitive adhesive tape provided with an adhesive layer made of the temperature-sensitive adhesive of the present invention on both surfaces of a base film.
• This fixing is performed by heating the ambient temperature to a temperature equal to or higher than the melting point of the side chain crystalline polymer using a heating means such as a heater.
• a heating means such as a heater.
• the flexible substrate has flexibility.
• Examples of the material constituting the flexible substrate include polycarbonate, polyethylene terephthalate, polymethyl methacrylate, polyimide, polyethylene naphthalate, polyethersulfone, thin film glass, and metal foil.
• Examples of the material constituting the support include glass.
• the pressure-sensitive adhesive layer of the temperature-sensitive pressure-sensitive adhesive tape contains a cross-linked polymer in which a side chain crystalline polymer and a metal chelate compound form a coordination bond, and thus has excellent heat resistance even in a high-temperature atmosphere. Can be shown.
• the 180 ° peel strength for stainless steel is usually 3 N / 25 mm or more, preferably 3 to 7 N / 25 mm. Therefore, according to the temperature-sensitive adhesive tape, the warp caused by the difference in thermal expansion between the flexible substrate and the support, the warp caused by volatilization of moisture, residual solvent, etc. in the adhesive layer, the floating stress, etc. And the flexible substrate can be kept fixed on the support.
• an acrylic pressure-sensitive adhesive tape is produced by adding a metal chelate compound to a general acrylic pressure-sensitive adhesive instead of the side chain crystalline polymer, there are the following problems. That is, when the acrylic pressure-sensitive adhesive tape is attached to an adherend and exposed to a high temperature atmosphere, the pressure-sensitive adhesive layer becomes flexible. As a result, the wettability of the pressure-sensitive adhesive layer with respect to the adherend surface is improved, and the pressure-sensitive adhesive layer follows the uneven shape existing on the surface of the adherend well, so that a so-called anchor effect is exhibited. Therefore, when the ambient temperature is lowered, the acrylic pressure-sensitive adhesive tape has a higher adhesive strength than the initial adhesive strength, and often causes poor peeling.
• the temperature-sensitive adhesive tape of the present invention contains a side-chain crystalline polymer, even if the adhesive strength becomes higher than the initial adhesive strength when exposed to a high-temperature atmosphere, the ambient temperature is changed to the side-chain crystal. When the temperature is lowered to a temperature lower than the melting point of the adhesive polymer, the side chain crystalline polymer is crystallized to reduce the adhesive force.
• the ambient temperature is cooled to a temperature lower than the melting point of the side chain crystalline polymer by using a cooling means such as a fan, the adhesive force of the adhesive layer is reduced.
• the conductive substrate can be easily peeled from the support.
• the flat panel display can be manufactured using the temperature-sensitive adhesive instead of the temperature-sensitive adhesive tape.
• the temperature-sensitive adhesive and the temperature-sensitive adhesive tape of the present invention are used for manufacturing a flat panel display device.
• the present invention is not limited to this, for example, a semiconductor It can be suitably used in fields where heat resistance is required, such as multilayer ceramic inductors, resistors, ferrites, sensor elements, thermistors, varistors, and ceramic electronic components.
• the copolymers of Synthesis Examples 1 and 2 are shown in Table 1.
• the said weight average molecular weight is a value which measured the copolymer by GPC and converted the obtained measured value into polystyrene.
• fusing point and crystallization temperature were measured on 10 degree-C / min measurement conditions by DSC.
• this copolymer solution was applied to one side of a 100 ⁇ m thick polyethylene terephthalate film and heated at 100 ° C. for 10 minutes to cause a crosslinking reaction, thereby forming a pressure sensitive adhesive layer having a thickness of 20 ⁇ m.
• a tape was prepared.
• the obtained temperature-sensitive adhesive tape was attached to a stainless steel plate at an ambient temperature of 40 ° C., and the ambient temperature was adjusted in the order of 40 ° C., 150 ° C. and 5 ° C., and held at each ambient temperature for 180 minutes.
• the peel strength was measured according to JIS Z0237.
• the 180 ° peeling was performed at a speed of 300 mm / min using a load cell. The results are shown in Table 2.
• a pressure-sensitive adhesive layer having a thickness of 20 ⁇ m was used in the same manner as in Example 1 except that the copolymer solution obtained in Synthesis Example 2 was used instead of the copolymer solution obtained in Synthesis Example 1.
• a temperature sensitive pressure-sensitive adhesive tape was formed. About the obtained temperature-sensitive adhesive tape, each atmosphere was measured in the same manner as in Example 1 except that the measurement atmosphere temperature was changed to 80 ° C., 150 ° C. and 23 ° C. instead of 40 ° C., 150 ° C. and 5 ° C. The 180 ° peel strength at temperature was measured. The results are shown in Table 3. The measurement at an ambient temperature of 23 ° C. was a sensory evaluation based on the same criteria as the measurement at the ambient temperature of 5 ° C.
• the temperature-sensitive adhesive tapes of Examples 1 and 2 have a 180 ° peel strength of 3 N / 25 mm or more with respect to stainless steel at an ambient temperature of 150 ° C. It can be seen that it maintains a high adhesive strength and is excellent in heat resistance. From the measurement results of 180 ° peel strength at ambient temperatures of 5 ° C. and 23 ° C., it can be seen that the adhesive strength is sufficiently lowered when cooled to a temperature below the melting point of the side chain crystalline polymer.
• Comparative Example 1 using an aziridine compound as a cross-linking agent and Comparative Example 2 using a metal chelate compound as an acrylic pressure-sensitive adhesive both have a 180 ° peel strength of less than 3 N / 25 mm at an ambient temperature of 150 ° C. The results were inferior in heat resistance. Moreover, since the 180 degree peeling strength in 5 degreeC atmospheric temperature is (5) in the comparative example 2, it turns out that the peeling defect has arisen.

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