WO2022186180A1 - 可変色粘着シートの変色抑制方法および積層シート - Google Patents
可変色粘着シートの変色抑制方法および積層シート Download PDFInfo
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- WO2022186180A1 WO2022186180A1 PCT/JP2022/008527 JP2022008527W WO2022186180A1 WO 2022186180 A1 WO2022186180 A1 WO 2022186180A1 JP 2022008527 W JP2022008527 W JP 2022008527W WO 2022186180 A1 WO2022186180 A1 WO 2022186180A1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B27/00—Layered products comprising a layer of synthetic resin
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
-
- 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
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-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J201/00—Adhesives based on unspecified macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- 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]
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- 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 method for suppressing discoloration of a color-changeable pressure-sensitive adhesive sheet and a laminated sheet.
- a transparent adhesive sheet that can color the irradiated area by irradiating light with a predetermined wavelength is known.
- a color-changeable adhesive sheet contains a post-colorant (component or components) that colors the adhesive sheet due to light irradiation.
- a display panel such as an organic EL panel has a laminated structure including a pixel panel and a cover member.
- a color-changeable pressure-sensitive adhesive sheet is used for bonding the elements included in the laminated structure.
- the color-changeable adhesive sheet is attached to the adherend (lamination process).
- the presence or absence of foreign matter and air bubbles between the adherend and the color-changeable pressure-sensitive adhesive sheet is inspected. If it does not pass the inspection, the color changeable adhesive sheet is peeled off from the first adherend, and then the lamination process is redone using another color changeable adhesive sheet.
- predetermined portions of the color-changeable pressure-sensitive adhesive sheet on the first adherend are colored by irradiation with light of a predetermined wavelength in order to impart design properties, shielding properties, antireflection properties, and the like. That is, a colored region is formed on the color-changeable pressure-sensitive adhesive sheet.
- the second adherend is joined to the first adherend via the color-changeable pressure-sensitive adhesive sheet.
- a color-changeable pressure-sensitive adhesive sheet used in this way is described, for example, in Patent Document 1 below.
- the present invention is a color-changeable pressure-sensitive adhesive sheet that can be colored by applying an external stimulus. and a laminated sheet obtained by the method.
- the present invention [1] provides a color-changeable pressure-sensitive adhesive sheet having colorability due to an external stimulus, the color-changeable pressure-sensitive adhesive sheet including a colored region and a non-colored region; and a second step of contacting the color-changeable adhesive sheet with a color-lowering medium for reducing the colorability of the color-changeable adhesive sheet.
- a color-reducing medium for reducing the colorability of the pressure-sensitive adhesive sheet is brought into contact with the color-changeable pressure-sensitive adhesive sheet including the colored region and the non-colored region.
- Such a configuration is suitable for reducing the colorability of the non-colored regions in the color-changeable pressure-sensitive adhesive sheet including the colored regions and the non-colored regions, thereby suppressing the discoloration of the non-colored regions over time.
- a color-changeable pressure-sensitive adhesive sheet including colored regions and non-colored regions is prepared in the first step, with such a second step scheduled to be performed later.
- Such a configuration is suitable for preparing the color-changeable pressure-sensitive adhesive sheet as a pressure-sensitive adhesive sheet having a high colorability due to an external stimulus and having a well-colored colored region. Even if the color-changeable pressure-sensitive adhesive sheet has high colorability so that the colored region is well colored, the colorability is reduced by contact with the color-decreasing medium in the second step. Therefore, after the second step, Discoloration of the non-pigmented areas over time is suppressed. As described above, the method of the present invention achieves good coloring of the colored regions and suppression of discoloration over time of the non-colored regions after the formation of the colored regions in the variable color pressure-sensitive adhesive sheet that can be colored by applying an external stimulus. , suitable for compatibility.
- the color-changeable pressure-sensitive adhesive sheet contains a first compound that undergoes a first reaction upon receiving an external stimulus, and a second compound that develops color through a second reaction with the product of the first reaction. and the method for suppressing discoloration of the color-changeable pressure-sensitive adhesive sheet according to [1] above.
- a color-changeable pressure-sensitive adhesive sheet appropriately colored by cooperation of the first compound and the second compound can be prepared in the first step.
- the present invention [3] is the color-changeable pressure-sensitive adhesive sheet according to [2] above, wherein the first compound is a photoacid generator, and the second compound is a color-developing compound that develops color upon reaction with an acid. Including discoloration control method.
- the color-changeable adhesive sheet colored using light irradiation as the external stimulus can be prepared in the first step.
- an acid is generated from the photoacid generator at the irradiated site, and the color-developing compound reacts with the acid to develop a color, thereby coloring the site.
- the first compound is extracted from the color-changeable pressure-sensitive adhesive sheet into the reduced coloring medium, or the reduced coloring medium reduces the coloring.
- the color-reducing adhesive according to [2] or [3] above, wherein the coloring-reducing component is introduced from the coloring-reducing medium to the color-changeable adhesive sheet in the second step. Includes sheet discoloration suppression method.
- Such a configuration is suitable for reducing the colorability of the color-changeable pressure-sensitive adhesive sheet in the second step.
- the present invention [5] is a first system in which the first compound, the second compound, and the coloring-reducing component coexist, wherein the reduction in transmittance ⁇ T1 due to the application of the external stimulus is determined by the presence of the coloring-reducing component.
- Such a configuration is suitable for reducing the colorability of the color-changeable pressure-sensitive adhesive sheet in the second step.
- the present invention [6] is the color-changeable pressure-sensitive adhesive sheet according to [5] above, wherein the coloring-lowering component contains at least one selected from the group consisting of an ultraviolet absorber, a neutralizing agent, and a radical trapping agent. including a discoloration suppression method.
- Such a configuration is suitable for reducing the colorability of the color-changeable pressure-sensitive adhesive sheet in the second step when a photoacid generator is used as the first component.
- the present invention is the above-described [1] to [6], wherein the reduced-colorability medium is a reduced-colorability sheet, and in the second step, the reduced-colorability sheet is attached to the color-changeable pressure-sensitive adhesive sheet.
- a method for suppressing discoloration of a color-changeable pressure-sensitive adhesive sheet according to any one of the above is included.
- Such a configuration is suitable for efficiently performing the second step in the manufacturing process of a device using a color-changeable adhesive sheet.
- a mask material is interposed between at least a part of the colored region of the color-changeable pressure-sensitive adhesive sheet and the reduced coloring sheet.
- Such a configuration is suitable for controlling portions of the color-changeable pressure-sensitive adhesive sheet in which the colorability is lowered in the second step.
- the present invention includes the method for suppressing discoloration of a color-changeable pressure-sensitive adhesive sheet according to [7] or [8] above, wherein the color-reducing sheet contains a polar group-containing polymer.
- Such a configuration is suitable for extracting the first compound from the color-changeable pressure-sensitive adhesive sheet to the color-reducing sheet in the second step.
- the present invention [10] includes the method for suppressing discoloration of a color-changeable pressure-sensitive adhesive sheet according to any one of [7] to [9] above, wherein the reduced-colorability sheet is a pressure-sensitive adhesive sheet.
- Such a configuration is suitable for highly adhering the color-reducing sheet to the color-changeable pressure-sensitive adhesive sheet in the second step. Moreover, this configuration is suitable for making the laminated sheet (laminated body of the color-changeable adhesive sheet and the color-reducing sheet) obtained in the second step function as a double-sided adhesive sheet.
- the present invention [11] includes the method for suppressing discoloration according to any one of [1] to [6] above, wherein the reduced-coloring medium is a reduced-coloring solvent.
- Such a configuration is preferable for efficiently performing the second step.
- the present invention [12] is a laminated sheet obtained by the method for suppressing discoloration of a color-changeable pressure-sensitive adhesive sheet according to any one of [7] to [10] above, comprising: the color-changeable pressure-sensitive adhesive sheet; A laminated sheet comprising the coloring-impaired sheet attached to an adhesive sheet.
- Such a laminated sheet is suitable for assembling a color-changeable pressure-sensitive adhesive sheet that satisfies both good coloring of colored regions and suppression of discoloration of non-colored regions as a structural member of a device such as a display panel.
- 1 shows the first step in one embodiment of the method for suppressing discoloration of a color-changeable pressure-sensitive adhesive sheet of the present invention.
- 2 shows the second step in one embodiment of the method for suppressing discoloration of a color-changeable pressure-sensitive adhesive sheet of the present invention.
- the case where the 1st member and the 2nd member were joined through the lamination sheet after the 2nd process shown in FIG. 2 is represented.
- the second step when a coloring-impaired solvent is used as the coloring-impaired medium, or when the coloring-impaired sheet is peeled off from the color-changeable pressure-sensitive adhesive sheet after the second step, after the second step, the first member and the second member are joined via the color-changeable pressure-sensitive adhesive sheet.
- the color-reducing sheet is attached to the color-changeable adhesive sheet with a mask material interposed between the colored region of the color-changeable adhesive sheet and the color-reducing sheet.
- the method for suppressing discoloration of a color-changeable pressure-sensitive adhesive sheet of the present invention includes a first step and a second step.
- a color-changeable adhesive sheet X is prepared.
- the variable color adhesive sheet X has a sheet shape with a predetermined thickness and extends in a direction (plane direction) perpendicular to the thickness direction.
- the color-changeable adhesive sheet X is formed from the first adhesive composition.
- the color-changeable adhesive sheet X is an adhesive sheet that is colored by an external stimulus. 12 (uncolored areas).
- the second region 12 preferably has transparency (visible light transmittance).
- the color-changeable pressure-sensitive adhesive sheet X comprises a base polymer, a first compound that undergoes a first reaction upon receiving an external stimulus, and a second compound that develops color through a second reaction with the product of the first reaction. contains. According to such a configuration, the color-changeable pressure-sensitive adhesive sheet X appropriately colored by cooperation of the first compound and the second compound can be prepared in the first step.
- Examples of external stimuli include light irradiation and heating, depending on the components contained in the color-changeable adhesive sheet X.
- Types of light for light irradiation include, for example, ultraviolet light, visible light, and infrared light, and ultraviolet light is preferable from the viewpoint of the diversity of equipment used.
- the first compound is a photoacid generator
- the second compound is a color-developing compound that develops color upon reaction with acid.
- the color-changeable pressure-sensitive adhesive sheet X By irradiating the color-changeable pressure-sensitive adhesive sheet X with light of a predetermined wavelength, an acid is generated from the photoacid generator at the irradiated portion, and the color-developing compound reacts with the acid to develop a color, thereby coloring the portion. More specifically, the components of the color-changeable pressure-sensitive adhesive sheet X are as described below.
- the color-changeable pressure-sensitive adhesive sheet X may be attached to a predetermined adherend.
- FIG. 1 exemplarily shows a state in which the color-changeable adhesive sheet X is attached to one surface of the first member 21 in the thickness direction T.
- the first member 21 is, for example, a display panel such as an organic EL panel.
- the first member 21 may be another electronic device or an optical device.
- an external stimulus is applied to a predetermined portion of the color-changeable pressure-sensitive adhesive sheet X to form the first region 11 .
- the presence or absence of foreign substances and air bubbles between the first member 21 and the color-changeable adhesive sheet X is inspected. .
- Discoloration media and extraction media are included as media with reduced coloration.
- the deactivating medium is a medium that contains a coloring property-reducing component for deteriorating the coloring property of the color-changeable adhesive sheet X, and is a medium for introducing the component into the color-changeable adhesive sheet X (the deactivating media is a variable It is a medium for inhibiting/deactivating coloring as a function of the colored adhesive sheet X).
- diffusion of the color-reducing component occurs so that the concentration distribution of the color-reducing component in the system becomes less biased.
- the extraction medium is a medium for extracting the first compound from the color-changeable adhesive sheet X to reduce the colorability of the color-changeable adhesive sheet X.
- FIG. In a system consisting of the color-changeable pressure-sensitive adhesive sheet X and an extraction medium in contact with the sheet, the first compound diffuses so that the concentration distribution of the first compound in the system is less biased. Thereby, the first compound can be extracted from the color-changeable adhesive sheet X to the extraction medium (extraction function).
- the disused media described above also serves as media for extraction when it has such an extraction function and the introduction function described above.
- the above deactivation media and extraction media are suitable for reducing the colorability of the color-changeable pressure-sensitive adhesive sheet X in the second step.
- the coloring-impaired media include a coloring-impairing sheet and a coloring-impairing solvent. That is, the color-reducing media includes deactivating sheets, extracting sheets, deactivating solvents, and extracting solvents.
- the color-reducing sheet is a pressure-sensitive adhesive sheet in this embodiment.
- FIG. 2 shows the case where the coloring-impaired sheet Y as the coloring-impaired medium is used in the second step.
- the color-reducing sheet Y is adhered to one side of the color-changeable pressure-sensitive adhesive sheet X in the thickness direction T.
- the coloring-reduced sheet Y has a sheet shape with a predetermined thickness and extends in a direction (surface direction) perpendicular to the thickness direction.
- the coloring-impaired sheet Y is a pressure-sensitive adhesive sheet formed from the second pressure-sensitive adhesive composition in this embodiment.
- the lamination sheet L is obtained by this process.
- the laminated sheet L includes a color-changeable pressure-sensitive adhesive sheet X and a color-lowering sheet Y attached to the color-changeable pressure-sensitive adhesive sheet X.
- the time for which the color-reducing adhesive sheet Y is brought into contact with the color-changeable pressure-sensitive adhesive sheet X is preferably 1 minute or longer, more preferably 3 minutes or longer, and even more preferably 5 minutes or longer.
- the contact time is preferably 72 hours or less, more preferably 48 hours or less, even more preferably 24 hours or less, and particularly preferably 12 hours or less. is.
- the color-changeable pressure-sensitive adhesive sheet X is brought into contact with the coloring-lowering solvent in the second step.
- the specific components of the coloring-reducing solvent are as described below.
- the contact method includes, for example, immersing the color-changeable pressure-sensitive adhesive sheet X in the color-reducing solvent and spraying the color-changeable pressure-sensitive adhesive sheet X with the color-reducing solvent.
- the time for which the color-changing pressure-sensitive adhesive sheet X is brought into contact with the color-reducing solvent is preferably 1 minute or longer, more preferably 3 minutes or longer, and even more preferably 5 minutes or longer.
- the contact time is preferably 72 hours or less, more preferably 48 hours or less, still more preferably 24 hours or less, and particularly preferably 12 hours or less.
- the second step it is preferable to heat the color-changeable pressure-sensitive adhesive sheet X and the reduced-colorability medium (the reduced-colorability sheet Y in FIG. 2).
- the heating promotes the movement of the color-reducing components in the disabling media to the color-changeable pressure-sensitive adhesive sheet X.
- FIG. When an extraction medium is used as the color-lowering medium, heating promotes the movement of the first component in the color-changeable pressure-sensitive adhesive sheet X to the extraction medium.
- the heating temperature in the second step is preferably 30° C. or higher, more preferably 50° C. or higher, and preferably 150° C. or lower, more preferably 100° C. or lower.
- the color-changeable adhesive sheet X including the first region 11 (colored region) and the second region 12 (non-colored region) is colored.
- a color reducing medium for reducing the properties is brought into contact.
- the configuration reduces the colorability of the first region 11 to suppress discoloration of the first region 11 over time, and the second compound (coloring component ), and therefore also suitable for ensuring the coloring stability of the first region 11 (specifically, for example, shown in Examples 7 and 8 and Comparative Example 3 below) as follows). That is, this method can also be implemented as a method for stabilizing coloring of the color-changeable pressure-sensitive adhesive sheet X having a colored region. Even when the colored region is formed on the entire surface of the color-changeable adhesive sheet X, the effect of stabilizing the coloring of the colored region can be obtained.
- Color stabilization of the colored regions of the color-changeable pressure-sensitive adhesive sheet X is preferable from the viewpoint of ensuring the functions (design, shielding, antireflection, etc.) of the colored regions according to the application of the color-changeable pressure-sensitive adhesive sheet X.
- the color-changeable adhesive sheet X including the first region 11 and the second region 12 is prepared in the first step, with such a second step scheduled to be performed later.
- Such a configuration is suitable for preparing the color-changeable pressure-sensitive adhesive sheet X as a pressure-sensitive adhesive sheet having a high colorability due to an external stimulus and a well-colored first region 11 (in the color-changeable pressure-sensitive adhesive sheet X, The higher the content of the first compound and/or the second compound, the higher the colorability of the color-changeable pressure-sensitive adhesive sheet X).
- the coloring property-reduced pressure-sensitive adhesive sheet X may be used in the second step. Since the colorability is lowered by the contact, the discoloration of the second region 12 over time is suppressed after such a second step.
- this method achieves both good coloring of the first region 11 and suppression of discoloration of the second region 12 over time in the color-changeable pressure-sensitive adhesive sheet X that can be colored by applying an external stimulus.
- the photoacid generator (first compound), the color-developing compound (second compound), and the coloring-reducing component are added before the coloring treatment. coexists, the color-changeable pressure-sensitive adhesive sheet has low coloring ability and is difficult to color.
- the predetermined region can sufficiently exhibit its coloring ability and can be satisfactorily obtained. While being colored (formation of the first region 11), the non-colored region (second region 12) is made difficult to discolor, thereby suppressing discoloration.
- the second member M2 is, for example, a transparent cover member.
- transparent cover members include transparent plastic films and transparent glass plates.
- the first member 21 and the second member 22 are joined via the color-changeable adhesive sheet X, as shown in FIG.
- the laminate Z2 having the first member 21, the color-changeable adhesive sheet X, and the second member 22 in order in the thickness direction T is obtained.
- the first adhesive composition forming the color-changeable adhesive sheet X is a second composition comprising a base polymer, a first compound that undergoes a first reaction upon receiving an external stimulus, and a product of the first reaction. and a second compound that develops color upon reaction.
- the base polymer is an adhesive component for developing adhesiveness in the color-changeable adhesive sheet X.
- the base polymer exhibits rubber elasticity in the room temperature range.
- Base polymers include, for example, acrylic polymers, rubber polymers, polyester polymers, urethane polymers, polyether polymers, silicone polymers, polyamide polymers, and fluoropolymers. From the viewpoint of ensuring good transparency and adhesiveness in the color-changeable pressure-sensitive adhesive sheet X, an acrylic polymer (first acrylic polymer) is preferably used as the base polymer.
- An acrylic polymer is, for example, a copolymer of a monomer component (first monomer component) containing a (meth)acrylic acid alkyl ester at a ratio of 50% by mass or more.
- (Meth)acrylic acid means acrylic acid and/or methacrylic acid.
- (Meth)acrylic acid alkyl esters include, for example, (meth)acrylic acid alkyl esters having a linear or branched alkyl group having 1 to 20 carbon atoms.
- Examples of such (meth)acrylic acid alkyl esters include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, and (meth)acrylic acid.
- the (meth)acrylic acid alkyl esters may be used alone, or two or more of them may be used in combination.
- an acrylic acid alkyl ester having an alkyl group having 1 to 12 carbon atoms is preferably used, and more preferably having methyl methacrylate and an alkyl group having 2 to 12 carbon atoms.
- a (meth)acrylic acid alkyl ester is used in combination, and more preferably, methyl methacrylate and 2-ethylhexyl acrylate are used in combination.
- the ratio of the (meth)acrylic acid alkyl ester in the monomer component is preferably 50% by mass or more, more preferably 60% by mass or more, from the viewpoint of appropriately expressing basic properties such as adhesiveness in the color-changeable pressure-sensitive adhesive sheet X. Preferably, it is 70% by mass or more. The same ratio is, for example, 99% by mass or less.
- the first monomer component may contain a copolymerizable monomer copolymerizable with the (meth)acrylic acid alkyl ester.
- copolymerizable monomers include monomers having a polar group.
- Polar group-containing monomers include, for example, hydroxyl group-containing monomers, nitrogen atom-containing ring-containing monomers, and carboxy group-containing monomers.
- the polar group-containing monomer is useful for modifying the acrylic polymer, such as introducing cross-linking points into the acrylic polymer and securing the cohesive strength of the acrylic polymer.
- the copolymerizable monomer preferably contains at least one selected from the group consisting of hydroxyl group-containing monomers, nitrogen atom-containing ring-containing monomers, and carboxy group-containing monomers. More preferably, the copolymerizable monomer includes a hydroxyl group-containing monomer and/or a monomer having a nitrogen atom-containing ring.
- hydroxyl group-containing monomers examples include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, (meth) ) 4-hydroxybutyl acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 10-hydroxydecyl (meth)acrylate, 12-hydroxylauryl (meth)acrylate, and ( 4-hydroxymethylcyclohexyl)methyl (meth)acrylate.
- 2-hydroxyethyl (meth)acrylate is preferably used, and 2-hydroxyethyl acrylate is more preferably used.
- the ratio of the hydroxyl group-containing monomer in the first monomer component is preferably 1% by mass or more, more preferably 3% by mass, from the viewpoints of introducing a crosslinked structure into the acrylic polymer and ensuring cohesive strength in the color-changeable pressure-sensitive adhesive sheet X. % or more, more preferably 5 mass % or more. From the viewpoint of adjusting the polarity of the acrylic polymer, the same ratio is preferably 30% by mass or less, more preferably 20% by mass or less.
- the polarity of the acrylic polymer is related to the compatibility between various additive components in the color-changeable pressure-sensitive adhesive sheet X and the acrylic polymer.
- Examples of monomers having a nitrogen atom-containing ring include N-vinyl-2-pyrrolidone, N-methylvinylpyrrolidone, N-vinylpyridine, N-vinylpiperidone, N-vinylpyrimidine, N-vinylpiperazine, N-vinylpyrazine, N-vinylpyrrole, N-vinylimidazole, N-vinyloxazole, N-(meth)acryloyl-2-pyrrolidone, N-(meth)acryloylpiperidine, N-(meth)acryloylpyrrolidine, N-vinylmorpholine, N-vinyl -3-morpholinone, N-vinyl-2-caprolactam, N-vinyl-1,3-oxazin-2-one, N-vinyl-3,5-morpholinedione, N-vinylpyrazole, N-vinylisoxazole, N -vinylthiazole,
- the ratio of the monomer having a nitrogen atom-containing ring in the first monomer component is preferable from the viewpoint of ensuring the cohesive force of the color-changeable pressure-sensitive adhesive sheet X and the adhesion to the adherend of the color-changeable pressure-sensitive adhesive sheet X. is 1% by mass or more, more preferably 3% by mass or more, and still more preferably 5% by mass or more. The same proportion is preferably 30% by mass or less, more preferably 20% by mass or less, from the viewpoint of adjusting the glass transition temperature of the acrylic polymer and adjusting the polarity of the acrylic polymer.
- Carboxy group-containing monomers include, for example, acrylic acid, methacrylic acid, carboxyethyl acrylate, carboxypentyl acrylate, itaconic acid, maleic acid, fumaric acid, crotonic acid, and isocrotonic acid.
- the ratio of the carboxyl group-containing monomer in the first monomer component is used to introduce a crosslinked structure into the acrylic polymer, ensure the cohesive force of the color-changeable pressure-sensitive adhesive sheet X, and ensure the adhesion to the adherend of the color-changeable pressure-sensitive adhesive sheet X. From the viewpoint, it is preferably 1% by mass or more, more preferably 3% by mass or more, and still more preferably 5% by mass or more. The ratio is preferably 30% by mass or less, more preferably 20% by mass or less, from the viewpoints of adjusting the glass transition temperature of the acrylic polymer and avoiding the risk of acid corrosion of the adherend.
- the first monomer component may contain other copolymerizable monomers (the same applies to the second monomer component described later).
- Other copolymerizable monomers include, for example, acid anhydride monomers, sulfonic acid group-containing monomers, phosphoric acid group-containing monomers, epoxy group-containing monomers, cyano group-containing monomers, alkoxy group-containing monomers, and aromatic vinyl compounds. be done.
- the acrylic polymer can be formed by polymerizing the first monomer component described above.
- the polymerization method includes, for example, solution polymerization, bulk polymerization, and emulsion polymerization, preferably solution polymerization.
- the polymerization initiator for example, a thermal polymerization initiator is used.
- the amount of the polymerization initiator used is, for example, 0.05 parts by mass or more and, for example, 1 part by mass or less with respect to 100 parts by mass of the first monomer component.
- Thermal polymerization initiators include, for example, azo polymerization initiators and peroxide polymerization initiators.
- azo polymerization initiators include 2,2'-azobisisobutyronitrile, 2,2'-azobis-2-methylbutyronitrile, 2,2'-azobis(2-methylpropionate)dimethyl, 4,4'-azobis-4-cyanovaleric acid, azobisisovaleronitrile, 2,2'-azobis(2-amidinopropane) dihydrochloride, 2,2'-azobis[2-(5-methyl-2- imidazolin-2-yl)propane]dihydrochloride, 2,2'-azobis(2-methylpropionamidine) disulfate, and 2,2'-azobis(N,N'-dimethyleneisobutyramidine) dihydrochloride mentioned.
- Peroxide polymerization initiators include, for example, dibenzoyl peroxide, t-butyl permaleate, and lauroyl peroxid
- the weight-average molecular weight of the acrylic polymer is preferably 100,000 or more, more preferably 300,000 or more, and even more preferably 500,000 or more, from the viewpoint of ensuring the cohesive force of the color-changeable pressure-sensitive adhesive sheet X.
- the weight-average molecular weight is preferably 5 million or less, more preferably 3 million or less, still more preferably 2 million or less.
- the weight average molecular weight of the acrylic polymer is calculated by measuring by gel permeation chromatography (GPC) and converting to polystyrene.
- the glass transition temperature (Tg) of the acrylic polymer is preferably 0°C or lower, more preferably -10°C or lower, and even more preferably -20°C or lower.
- the glass transition temperature is, for example, ⁇ 80° C. or higher.
- the glass transition temperature (Tg) of the polymer the glass transition temperature (theoretical value) obtained based on the following Fox formula can be used.
- the Fox equation is a relational expression between the glass transition temperature Tg of a polymer and the glass transition temperature Tgi of a homopolymer of monomers constituting the polymer.
- Tg represents the glass transition temperature (° C.) of the polymer
- Wi represents the weight fraction of the monomer i constituting the polymer
- Tgi represents the glass transition of the homopolymer formed from the monomer i.
- Literature values can be used for the glass transition temperature of homopolymers.
- the glass transition temperature of a homopolymer of a monomer can also be determined by the method specifically described in JP-A-2007-51271.
- the first adhesive composition may contain a cross-linking agent from the viewpoint of introducing a cross-linked structure into the base polymer.
- Crosslinkers include, for example, isocyanate crosslinkers, epoxy crosslinkers, oxazoline crosslinkers, aziridine crosslinkers, carbodiimide crosslinkers, and metal chelate crosslinkers.
- the cross-linking agents may be used alone, or two or more of them may be used in combination.
- isocyanate cross-linking agents examples include tolylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, hydrogenated xylylene diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, tetramethylxylylene diisocyanate, naphthalene diisocyanate, triphenylmethane triisocyanate, isocyanates, and polymethylene polyphenyl isocyanates.
- the isocyanate cross-linking agent also includes derivatives of these isocyanates.
- isocyanate derivative examples include isocyanurate-modified products and polyol-modified products.
- Commercially available isocyanate cross-linking agents include, for example, Coronate L (trimethylolpropane adduct of tolylene diisocyanate, manufactured by Tosoh Corporation), Coronate HL (trimethylolpropane adduct of hexamethylene diisocyanate, manufactured by Tosoh Corporation), and Coronate HX. (isocyanurate of hexamethylene diisocyanate, manufactured by Tosoh Corporation) and Takenate D110N (trimethylolpropane adduct of xylylene diisocyanate, manufactured by Mitsui Chemicals, Inc.).
- epoxy cross-linking agents include bisphenol A, epichlorohydrin type epoxy resin, ethylene glycidyl ether, polyethylene glycol diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether, 1,6-hexanediol glycidyl ether, trimethylolpropane triglycidyl ether. , diglycidylaniline, diamine glycidylamine, N,N,N',N'-tetraglycidyl-m-xylylenediamine, and 1,3-bis(N,N-diglycidylaminomethyl)cyclohexane.
- the amount of the cross-linking agent is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, with respect to 100 parts by mass of the base polymer. More preferably, it is 0.07 parts by mass or more.
- the amount of the cross-linking agent blended with respect to 100 parts by mass of the base polymer is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably It is 3 parts by mass or less.
- a cross-linking catalyst When a cross-linked structure is introduced into the base polymer, a cross-linking catalyst may be used to effectively promote the cross-linking reaction.
- Cross-linking catalysts include, for example, dibutyltin dilaurate, tetra-n-butyl titanate, tetraisopropyl titanate, Nasem ferric iron, and butyltin oxide, preferably dibutyltin dilaurate.
- the amount of the cross-linking catalyst used is, for example, 0.0001 parts by mass or more and, for example, 1 part by mass or less with respect to 100 parts by mass of the base polymer.
- a cross-linking inhibitor that can be subsequently removed from the first adhesive composition may be blended into the first adhesive composition.
- dibutyltin dilaurate is used as the cross-linking catalyst
- acetylacetone is preferably used as the cross-linking inhibitor.
- acetylacetone is coordinated to dibutyltin dilaurate, and progress of the cross-linking reaction of the cross-linking agent with respect to the base polymer is suppressed.
- the acetylacetone is volatilized by heating at a desired timing to form a coating film. can be removed from This allows the cross-linking reaction of the cross-linking agent to proceed.
- the amount of the cross-linking inhibitor is preferably 100 parts by mass or more, more preferably 1000 parts by mass or more, relative to 100 parts by mass of the cross-linking catalyst. Moreover, the compounding amount is, for example, 5000 parts by mass or less.
- Examples of the first compound include acid generators.
- Acid generators include, for example, photoacid generators and thermal acid generators.
- the photoacid generator is excited by irradiation with light of a predetermined wavelength or wavelength range to cause an acid generation reaction and generate acid.
- the acid generation reaction is, for example, a decomposition reaction of the photoacid generator.
- the wavelength of light that efficiently causes the acid generating reaction varies depending on the type of photoacid generator.
- photoacid generators include onium compounds that generate acid when irradiated with ultraviolet rays.
- Onium compounds are provided, for example, in the form of onium salts of onium cations and anions.
- Onium cations include, for example, sulfonium and iodonium.
- Examples of anions include Cl ⁇ , Br ⁇ , I ⁇ , ZnCl 3 ⁇ , HSO 3 ⁇ , BF 4 ⁇ , PF 6 ⁇ , AsF 6 ⁇ , SbF 6 ⁇ , CH 3 SO 3 ⁇ , CF 3 SO 3 ⁇ , C 4 F 9 HSO 3 ⁇ , (C 6 F 5 ) 4 B ⁇ , and (C 4 H 9 ) 4 B ⁇ .
- the photoacid generators may be used alone, or two or more of them may be used in combination.
- An onium salt of sulfonium and C 4 F 9 HSO 3 — and/or an onium salt of iodonium salt and C 4 F 9 HSO 3 — is preferably used as the photoacid generator.
- the amount of the photoacid generator to be blended with respect to 100 parts by mass of the base polymer is preferably 1 part by mass or more, more preferably 2 parts by mass or more, still more preferably 5 parts by mass or more, and particularly preferably 7 parts by mass or more.
- the blending amount is preferably 20 parts by mass or less, more preferably 15 parts by mass or less, and even more preferably 12 parts by mass or less.
- the amount of the photoacid generator to be added to 100 parts by mass of the color forming compound described later is preferably 100 parts by mass or more, more preferably 200 parts by mass or more, still more preferably 300 parts by mass or more, and particularly preferably 330 parts by mass or more. is.
- the blending amount is preferably 1000 parts by mass or less, more preferably 700 parts by mass or less, and even more preferably 500 parts by mass or less.
- Examples of the second compound include color-developing compounds that develop color upon reaction with an acid.
- Examples of such color-forming compounds include leuco dyes, triarylmethane dyes, diphenylmethane dyes, fluorane dyes, spiropyran dyes, and rhodamine dyes.
- the color-developing compounds may be used alone, or two or more of them may be used in combination.
- Leuco dyes include, for example, 2'-anilino-6'-(N-ethyl-N-isopentylamino)-3'-methylspiro[phthalide-3,9'-[9H]xanthene], 3-dibutylamino- 6-methyl-7-anilinofluorane, 3-dipropylamino-6-methyl-7-anilinofluorane, 3-diethylamino-6-methyl-7-anilinofluorane, 3-dimethylamino-6- Methyl-7-anilinofluorane, 3-diethylamino-6-methyl-7-xyridinofluorane, and 3-(4-diethylamino-2-ethoxyphenyl)-3-(1-ethyl-2-methylindole) -3-yl)-4-azaphthalide.
- triarylmethane dyes examples include p,p′,p′′-tris-dimethylaminotriphenylmethane.
- diphenylmethane dyes examples include 4,4-bis-dimethylaminophenylbenzhydrylbenzyl ether.
- fluorane dyes examples include 3-diethylamino-6-methyl-7-chlorofluorane
- examples of spiropyran dyes include 3-methylspirodinaphthopyran
- examples of rhodamine dyes examples include: Examples include rhodamine-B-anilinolactam.
- the color-developing compound is preferably a leuco dye, more preferably 2'-anilino-6'-(N-ethyl-N-isopentylamino). -3'-methylspiro[phthalido-3,9'-[9H]xanthene] is used.
- the amount of the color-developing compound compounded with respect to 100 parts by mass of the base polymer is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more.
- the blending amount is preferably 10 parts by mass or less, more preferably 7 parts by mass or less.
- the first adhesive composition may contain other components as necessary.
- Other ingredients include, for example, silane coupling agents, tackifiers, plasticizers, softeners, antioxidants, surfactants, sensitizers, and antistatic agents.
- the color-changeable pressure-sensitive adhesive sheet X can be produced, for example, by applying the varnish of the first pressure-sensitive adhesive composition described above to the base film to form a coating film, and then drying the coating film.
- base films include flexible plastic films.
- the plastic film include polyethylene terephthalate film, polyethylene film, polypropylene film, and polyester film.
- the thickness of the base film is, for example, 3 ⁇ m or more and, for example, 200 ⁇ m or less.
- the surface of the base film is preferably release-treated.
- the cross-linking reaction proceeds simultaneously with the above-described drying or by subsequent aging.
- Aging conditions are appropriately set according to the type of cross-linking agent.
- the aging temperature is, for example, 20°C to 160°C.
- Aging time is, for example, from 1 minute to 7 days.
- a release film may be further laminated on the color-changeable pressure-sensitive adhesive sheet X on the base film before or after aging.
- the release film is a flexible plastic film to which surface release treatment has been applied. Release films include, for example, the plastic films described above with respect to the base film.
- the color-changeable adhesive sheet X whose adhesive surface is covered and protected by the release film can be manufactured.
- Each release film is peeled off from the color-changeable pressure-sensitive adhesive sheet X when the color-changeable pressure-sensitive adhesive sheet X is used.
- the thickness of the color-changeable pressure-sensitive adhesive sheet X is preferably 10 ⁇ m or more, more preferably 15 ⁇ m or more, from the viewpoint of ensuring sufficient adhesion to the adherend. From the viewpoint of handleability of the color-changeable pressure-sensitive adhesive sheet X, the thickness of the color-changeable pressure-sensitive adhesive sheet X is preferably 300 ⁇ m or less, more preferably 200 ⁇ m or less, still more preferably 100 ⁇ m or less, and particularly preferably 50 ⁇ m or less.
- the average transmittance of the color-changeable pressure-sensitive adhesive sheet X at a wavelength of 400 to 700 nm is preferably 80% or more, more preferably 85% or more, still more preferably 90% or more, and particularly preferably 95% or more.
- Such a configuration is suitable for inspecting the presence or absence of foreign matter and air bubbles between the color-changeable adhesive sheet X and the adherend after bonding the color-changeable adhesive sheet X to the adherend.
- the average transmittance at wavelengths from 400 to 700 nm can be measured by the method described below with respect to the examples below.
- the second adhesive composition forming the color-reducing sheet Y contains a base polymer.
- the base polymer includes the base polymer described above with respect to the first adhesive composition, preferably an acrylic polymer (second acrylic polymer).
- the monomer component (second monomer component) forming the second acrylic polymer contains a (meth)acrylic acid alkyl ester.
- the (meth)acrylic acid alkyl ester include the (meth)acrylic acid alkyl esters described above with respect to the first acrylic polymer, and preferably, an acrylic acid alkyl ester having an alkyl group having 6 to 18 carbon atoms is used. 2-ethylhexyl acrylate and/or isostearyl acrylate are more preferably used.
- the ratio of the (meth)acrylic acid alkyl ester in the second monomer component is preferably 50% by mass or more, more preferably 60% by mass or more, from the viewpoint of appropriately expressing basic properties such as adhesiveness in the color-reducing sheet Y. , more preferably 70% by mass or more.
- the same ratio is, for example, 99% by mass or less.
- the second monomer component may contain a copolymerizable monomer copolymerizable with the (meth)acrylic acid alkyl ester.
- the copolymerizable monomer include the copolymerizable monomers described above for the first acrylic polymer, preferably a polar group-containing monomer, more preferably a hydroxyl group-containing monomer, a monomer having a nitrogen atom-containing ring, and , a carboxy group-containing monomer is used.
- a polar group-containing monomer more preferably a hydroxyl group-containing monomer, a monomer having a nitrogen atom-containing ring, and , a carboxy group-containing monomer is used.
- 2-hydroxyethyl acrylate and/or 4-hydroxybutyl acrylate are preferably used as the hydroxyl group-containing monomer in the second monomer component.
- N-vinyl-2-pyrrolidone is preferably used as the monomer having a nitrogen atom-containing ring in the second monomer component.
- Acrylic acid is preferably used as the carboxy group-containing monomer in the second monomer component.
- the acrylic polymer as the copolymer of the second monomer component containing the polar group-containing monomer is a polar group-containing polymer. Such an acrylic polymer is preferable for extracting the first compound such as the above photoacid generator from the color-changeable pressure-sensitive adhesive sheet X to the color-reducing sheet Y.
- the ratio of the polar group-containing monomer in the second monomer component is preferably 1% by mass or more, more preferably 3% by mass or more, from the viewpoint of ensuring cohesive strength of the acrylic polymer and adjusting the polarity of the acrylic polymer. It is more preferably 5% by mass or more, preferably 40% by mass or less, and more preferably 30% by mass or less.
- the coloring-impaired sheet Y is a sheet for extraction, from the viewpoint of ensuring ease of migration (extractability) of the photoacid generator from the color-changeable pressure-sensitive adhesive sheet X to the coloring-impaired sheet Y, the second monomer component
- the ratio of the polar group-containing monomer in is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 15% by mass or more, and is preferably 50% by mass or less, more preferably 35% by mass or less. is.
- the second acrylic polymer can be formed by polymerizing the second monomer component described above.
- the polymerization method includes, for example, solution polymerization, bulk polymerization, and emulsion polymerization, preferably solution polymerization.
- the polymerization initiator for example, the thermal polymerization initiator described above is used.
- the amount of the polymerization initiator used is, for example, 0.05 parts by mass or more and, for example, 1 part by mass or less with respect to 100 parts by mass of the second monomer component.
- the weight-average molecular weight of the second acrylic polymer is preferably 100,000 or more, more preferably 300,000 or more, and still more preferably 500,000 or more, from the viewpoint of ensuring the cohesive strength of the reduced-colorability sheet Y.
- the weight-average molecular weight is preferably 5 million or less, more preferably 3 million or less, still more preferably 2 million or less.
- the glass transition temperature (Tg) of the second acrylic polymer is preferably 0°C or lower, more preferably -10°C or lower, and even more preferably -20°C or lower.
- the glass transition temperature is, for example, ⁇ 80° C. or higher.
- the second adhesive composition may contain a cross-linking agent from the viewpoint of introducing a cross-linked structure into the base polymer.
- Cross-linking agents include, for example, the isocyanate cross-linking agents described above, the epoxy cross-linking agents described above, the oxazoline cross-linking agents, the aziridine cross-linking agents, the carbodiimide cross-linking agents, and the metal chelate cross-linking agents.
- the cross-linking agents may be used alone, or two or more of them may be used in combination.
- the amount of the cross-linking agent is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, with respect to 100 parts by mass of the base polymer. More preferably, it is 0.07 parts by mass or more.
- the amount of the cross-linking agent blended with respect to 100 parts by mass of the base polymer is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably It is 3 parts by mass or less.
- a cross-linking catalyst When a cross-linked structure is introduced into the base polymer, a cross-linking catalyst may be used to effectively promote the cross-linking reaction.
- the cross-linking catalyst include the cross-linking agents described above with respect to the first adhesive composition.
- the amount of the cross-linking catalyst used is, for example, 0.0001 parts by mass or more and, for example, 1 part by mass or less with respect to 100 parts by mass of the base polymer.
- a cross-linking inhibitor that can be subsequently removed from the second adhesive composition may be incorporated into the second adhesive composition.
- the cross-linking inhibitor include the cross-linking inhibitors described above with respect to the first adhesive composition.
- the amount of the cross-linking inhibitor to be blended is preferably 100 parts by mass or more, more preferably 1000 parts by mass or more with respect to 100 parts by mass of the cross-linking catalyst. Moreover, the compounding amount is, for example, 5000 parts by mass or less.
- the second adhesive composition further contains a coloring-reducing component.
- the coloring-lowering component include an ultraviolet absorber, a neutralizer, and a radical trapping agent.
- the coloring-lowering component preferably contains at least one selected from the group consisting of ultraviolet absorbers, neutralizers, and radical trapping agents.
- the ultraviolet absorber After being introduced from the color-reducing sheet Y into the color-changeable pressure-sensitive adhesive sheet X in the second step described above, the ultraviolet absorber absorbs part or all of the ultraviolet light received by the color-changeable pressure-sensitive adhesive sheet X.
- This UV absorption suppresses the acid generation reaction that occurs when the photoacid generator is exposed to UV irradiation, and thus suppresses the coloring of the color-developing compound. As a result, the colorability of the color-changeable pressure-sensitive adhesive sheet X after the second step is lowered.
- ultraviolet absorbers examples include benzotriazole ultraviolet absorbers, benzophenone ultraviolet absorbers, oxybenzophenone ultraviolet absorbers, hydroxyphenyltriazine ultraviolet absorbers, salicylic acid ester ultraviolet absorbers, and cyanoacrylate ultraviolet absorbers.
- the neutralizing agent neutralizes part or all of the acid generated by the photoacid generator after being introduced from the color-reducing sheet Y into the color-changeable pressure-sensitive adhesive sheet X in the second step described above.
- This neutralizing action suppresses the reaction between the acid and the color-developing compound that occurs when the photoacid generator is irradiated with ultraviolet rays. As a result, the colorability of the color-changeable pressure-sensitive adhesive sheet X after the second step is lowered.
- neutralizing agents include primary amines, secondary amines, and tertiary amines that exhibit alkalinity.
- Primary amines include, for example, monoethylamine and monoethanolamine.
- Secondary amines include, for example, diethylamine and diethanolamine.
- Tertiary amines include, for example, triethylamine, triethanolamine, N,N,N'-trimethylethylenediamine, N-methyldiethanolamine, and N,N-diethylhydroxylamine.
- the radical trapping agent traps radicals when radicals are generated at the start of the acid generation reaction of the photoacid generator after being introduced from the colorability-reducing sheet Y into the color-changeable pressure-sensitive adhesive sheet X in the second step described above. , to suppress the progress of the acid generation reaction. As a result, the color development of the color-developing compound is suppressed, and the colorability of the color-changeable pressure-sensitive adhesive sheet X after the second step is lowered.
- radical trapping agents include hindered amine compounds, hindered phenol compounds, N-oxyl compounds, naphthalene derivatives, thioether compounds, and hydrazil compounds, preferably hindered amine compounds.
- the ratio of the coloring-lowering component in the second adhesive composition is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and still more preferably 2 parts by mass or more, relative to 100 parts by mass of the base polymer. .
- the same ratio is preferably 20 parts by mass or less, more preferably 15 parts by mass or less, and even more preferably 10 parts by mass or less with respect to 100 parts by mass of the base polymer.
- the formation of the first regions 11 by applying an external stimulus to the color-changeable pressure-sensitive adhesive sheet X is inhibited.
- the color-reducing component when a deactivating medium is used as the color-reducing medium, the color-reducing component can be introduced into the color-changeable pressure-sensitive adhesive sheet X after the first region 11 is formed. can be avoided.
- the decrease in transmittance ⁇ T1 due to the application of an external stimulus in the first system in which the first compound, the second compound, and the coloring-reducing component coexist is preferably It is smaller than the decrease ⁇ T2 in transmittance due to the application of the same external stimulus to the second system that is the same as the first system.
- the difference between ⁇ T2 and ⁇ T1 ( ⁇ T2 ⁇ T1) is preferably 5% or more, more preferably 15% or more, even more preferably 30% or more, and particularly preferably 50% or more.
- the transmittance is, for example, the average transmittance at wavelengths from 400 to 700 nm, and can be measured by the method described below with respect to the examples below. Such a configuration is suitable for reducing the colorability of the color-changeable pressure-sensitive adhesive sheet X in the second step.
- the second adhesive composition may contain other ingredients as necessary.
- Other ingredients include, for example, silane coupling agents, tackifiers, plasticizers, softeners, antioxidants, surfactants, and antistatic agents.
- the second adhesive composition that forms the color-reducing sheet Y does not contain the first compound such as the photoacid generator described above and the second compound such as the color-developing compound described above.
- the second adhesive composition that forms the coloring-reducing sheet Y as an extraction sheet does not contain coloring-reducing components such as UV absorbers, neutralizers, and radical trapping agents.
- the coloring-reduced sheet Y can be produced, for example, by applying the varnish of the above-described second adhesive composition onto the base film to form a coating film, and then drying the coating film. Specifically, it is the same as the method for manufacturing the color-changeable pressure-sensitive adhesive sheet X described above.
- the thickness of the colorability-reducing sheet Y is preferably 10 ⁇ m or more, more preferably 20 ⁇ m or more, from the viewpoint of good expression of the colorability-reducing function. From the viewpoint of handleability of the coloring-impaired sheet Y, the thickness of the coloring-impaired sheet Y is preferably 300 ⁇ m or less, more preferably 200 ⁇ m or less.
- the average transmittance of the color-reducing sheet Y at a wavelength of 400 to 700 nm is higher than the average transmittance of the first region 11 of the color-changeable pressure-sensitive adhesive sheet X at a wavelength of 400 to 700 nm, for example, 40% or more. 99% or less.
- the average transmittance of the color-impaired sheet Y at a wavelength of 400 to 700 nm is preferably 45% or higher, more preferably 50% or higher, and even more preferably 60% or higher.
- the average transmittance is, for example, 100% or less.
- the wavelength of the reduced coloring sheet Y is preferably 90% or less, more preferably 80% or less, still more preferably 70% or less.
- the average transmittance is, for example, 50% or more.
- a masking material M is interposed between the first region 11 of the color-changeable pressure-sensitive adhesive sheet X and the color-reducing sheet X, and the color-reducing sheet Y is subjected to a color-changeable process. It may be attached to the adhesive sheet X.
- the mask material M may be placed on the color-changeable adhesive sheet X before the first regions 11 are formed, or may be placed on the color-changeable adhesive sheet X after the first regions 11 are formed. good too.
- the mask material M is, for example, a transparent plastic film.
- Materials for plastic films include, for example, polyolefins, polyesters, polyamides, polyimides, polyvinyl chloride, polyvinylidene chloride, cellulose, polystyrene, and polycarbonates.
- Polyolefins include, for example, polyethylene and polypropylene.
- Polyesters include, for example, polyethylene terephthalate, polyethylene naphthalate, and polybutylene terephthalate.
- Polyamides include, for example, polyamide 6, polyamide 6,6, and partially aromatic polyamides.
- the masking material M In the region where the masking material M is arranged, component movement between the color-changeable pressure-sensitive adhesive sheet X and the color-reducing sheet Y is prevented.
- the use of such a masking material M can be achieved in the second step by introducing a colorability-reducing component from the color-reducing sheet Y into the color-reducing adhesive sheet X, or removing the color-reducing component from the color-reducing adhesive sheet X with the color-reducing sheet Y in the second step. It is suitable for selectively and efficiently extracting one compound from the second region 12 .
- the coloring-lowering solvent as the coloring-lowering medium may contain a polar solvent or a low-polar solvent (non-polar solvent) as the main agent.
- Polar solvents include, for example, water, alcohols, and carboxylic acids.
- Polar solvents also include moderately polar solvents such as ethyl acetate, acetone, and acetonitrile.
- Alcohols include, for example, methanol, ethanol, isopropyl alcohol, and butanol.
- Carboxylic acids include formic acid and acetic acid.
- Low polarity solvents include, for example, benzene, toluene, and methyl isobutyl ketone.
- a liquid monomer exhibiting sufficient component solubility as a deactivating solvent or an extracting solvent can also be appropriately selected and used.
- Such liquid monomers include, for example, various acrylate monomers.
- the coloration-reducing solvent when the coloration-reducing solvent is a deactivating coloration-reducing solvent, the coloration-reducing solvent further contains a coloration-reducing component.
- the coloring-lowering component preferably contains at least one selected from the group consisting of ultraviolet absorbers, neutralizers, and radical trapping agents. Examples of the ultraviolet absorber, neutralizing agent and radical trapping agent include the ultraviolet absorbing agent, neutralizing agent and radical trapping agent described above with respect to the color-reducing sheet Y, preferably the radical trapping agent.
- the proportion of the coloring-lowering component in the coloring-lowering solvent is preferably 1% by mass or more, more preferably 5% by mass or more, and is preferably 60% by mass or less, preferably 50% by mass or less.
- ⁇ Preparation of acrylic polymer P1 > 63 parts by mass of 2-ethylhexyl acrylate (2EHA), 9 parts by mass of methyl methacrylate (MMA), and 2- Hydroxyethyl (HEA) 13 parts by mass, N-vinyl-2-pyrrolidone (NVP) 15 parts by mass, and 2,2'-azobisisobutyronitrile (AIBN) 0.2 parts by mass as a polymerization initiator , and 233 parts by mass of ethyl acetate as a solvent were stirred at 60° C. for 7 hours under a nitrogen atmosphere (polymerization reaction). This gave a first polymer solution containing the acrylic polymer P1.
- the weight average molecular weight (Mw) of acrylic polymer P1 in the first polymer solution was 1.2 million.
- Adhesive composition C2 was prepared in the same manner as adhesive composition C1, except that 4 parts by mass of a radical trapping agent (trade name “Tinuvin 249”, manufactured by BASF) was further added as a coloring-reducing component. did.
- a radical trapping agent trade name “Tinuvin 249”, manufactured by BASF
- Adhesive composition C3 was prepared in the same manner as adhesive composition C1 , except that 8 parts by mass of a radical trapping agent (trade name "Tinuvin 249", manufactured by BASF) was further added as a coloring - reducing component. did.
- ⁇ Preparation of adhesive composition C4 In the second polymer solution containing the acrylic polymer P2, an isocyanate cross-linking agent (trade name “Coronate HX”, isocyanurate of hexamethylene diisocyanate, manufactured by Tosoh Corporation) is added as a cross-linking agent per 100 parts by mass of the acrylic polymer P2.
- an isocyanate cross-linking agent (trade name “Coronate HX”, isocyanurate of hexamethylene diisocyanate, manufactured by Tosoh Corporation) is added as a cross-linking agent per 100 parts by mass of the acrylic polymer P2.
- Adhesive composition C5 was prepared in the same manner as adhesive composition C4 except that the amount of the radical trapping agent (trade name “Tinuvin 249”, manufactured by BASF) was changed to 8 parts by mass instead of 4 parts by mass. was prepared.
- the radical trapping agent trade name “Tinuvin 249”, manufactured by BASF
- ⁇ Preparation of adhesive composition C6 > In the second polymer solution containing the acrylic polymer P2, 0.25 parts by mass of an isocyanate cross-linking agent (trade name "Coronate HX", manufactured by Tosoh Corporation) per 100 parts by mass of the acrylic polymer P2 (in terms of solid content) is added as a cross-linking agent. amount), 0.01 parts by mass (in terms of solid content) of dibutyltin dilaurate (trade name “OL-1”, manufactured by Tokyo Fine Chemical Co., Ltd.) as a cross-linking catalyst, and 3 parts by mass of acetylacetone as a cross-linking inhibitor. and mixed together to prepare adhesive composition C6 .
- an isocyanate cross-linking agent trade name "Coronate HX", manufactured by Tosoh Corporation
- dibutyltin dilaurate trade name “OL-1”, manufactured by Tokyo Fine Chemical Co., Ltd.
- Adhesive Composition C7 was prepared in the same manner as Adhesive Composition C6, except that a third polymer solution was used in place of the second polymer solution.
- Adhesive composition C8 was prepared in the same manner as adhesive composition C1, except that 4 parts by mass of an ultraviolet absorber (trade name "Tinuvin 571", manufactured by BASF) was further added as a coloring-reducing component. did.
- Adhesive composition C9 was prepared in the same manner as adhesive composition C1, except that 8 parts by mass of an ultraviolet absorber (trade name "Tinuvin 571", manufactured by BASF) was further added as a coloring-reducing component. did.
- an ultraviolet absorber trade name "Tinuvin 571", manufactured by BASF
- composition C11 ⁇ Preparation of adhesive composition C11 > Radical trap agent (Tinuvin 249) In place of 4 parts by mass, an ultraviolet absorber (trade name "Tinuvin 571", manufactured by BASF) 8 parts by mass was used. Composition C11 was prepared.
- Adhesive composition C1 was applied onto the release - treated surface of a 38 ⁇ m-thick base film (trade name “MRF#38”, polyester film, manufactured by Mitsubishi Plastics Co., Ltd.) one side of which was release-treated. A coating was formed. The coating was then dried by heating at 132°C for 3 minutes. Thus, a pressure-sensitive adhesive layer having a thickness of 25 ⁇ m was formed on the base film. Next, the release-treated surface of a 38 ⁇ m-thick release film (trade name “MRE #38”, polyester film, manufactured by Mitsubishi Plastics Co., Ltd.) whose one side is release-treated is applied to the adhesive layer on the base film. pasted together.
- MRF#38 polyester film, manufactured by Mitsubishi Plastics Co., Ltd.
- a color-changeable pressure-sensitive adhesive sheet R1 with a protective film was prepared in the same manner as the color-changeable pressure - sensitive adhesive sheet X1, except that the pressure-sensitive adhesive composition C2 was used instead of the pressure - sensitive adhesive composition C1.
- a color-changeable pressure-sensitive adhesive sheet R2 with a protective film was prepared in the same manner as the color-changeable pressure - sensitive adhesive sheet X1, except that the pressure - sensitive adhesive composition C3 was used instead of the pressure - sensitive adhesive composition C1.
- a color-changeable pressure - sensitive adhesive sheet R3 with a protective film was prepared in the same manner as the color-changeable pressure - sensitive adhesive sheet X1, except that the pressure-sensitive adhesive composition C8 was used instead of the pressure - sensitive adhesive composition C1.
- a color-changeable pressure-sensitive adhesive sheet R4 with a protective film was prepared in the same manner as the color-changeable pressure - sensitive adhesive sheet X1, except that the pressure-sensitive adhesive composition C9 was used instead of the pressure - sensitive adhesive composition C1.
- Adhesive composition C4 was applied onto the release-treated surface of a 38 ⁇ m-thick base film (trade name “MRF#38”, polyester film, manufactured by Mitsubishi Plastics Co., Ltd.) one side of which was release-treated. A coating was formed. Next, the coating film was allowed to stand at room temperature for 10 minutes, then dried by heating at 80° C. for 5 minutes and then heating at 130° C. for 1 minute. Thus, a pressure-sensitive adhesive layer having a thickness of 25 ⁇ m was formed on the base film.
- the release-treated surface of a 38 ⁇ m-thick release film (trade name “MRE #38”, polyester film, manufactured by Mitsubishi Plastics Co., Ltd.) whose one side is release-treated is applied to the adhesive layer on the base film. pasted together. After that, aging treatment was performed at 60° C. for 24 hours to advance the cross-linking reaction in the pressure-sensitive adhesive layer. As described above, a deactivating pressure-sensitive adhesive sheet D 1 (thickness: 25 ⁇ m) with a protective film was produced.
- Deactivated adhesive sheet D2 with a protective film was prepared in the same manner as deactivated adhesive sheet D1, except that adhesive composition C5 was used instead of adhesive composition C4 .
- Deactivated adhesive sheet D3 with a protective film was prepared in the same manner as deactivated adhesive sheet D1 , except that adhesive composition C10 was used instead of adhesive composition C4 .
- Deactivated adhesive sheet D4 with a protective film was prepared in the same manner as deactivated adhesive sheet D1, except that adhesive composition C11 was used instead of adhesive composition C4 .
- Example 1 A laminate L 1 was obtained from the color-changeable adhesive sheet X 1 and the deactivating adhesive sheet D 1 in the following manner.
- the color-changeable pressure-sensitive adhesive sheet X1 was prepared (first step). Specifically, after peeling off the release film from the color-changeable pressure - sensitive adhesive sheet X1, the same sheet was attached to Eagle Glass (thickness: 0.55 mm, manufactured by Matsunami Glass Co., Ltd.). Next, after peeling off the base film from the color - changeable adhesive sheet X1 on eagle glass and peeling off the release film from the deactivating adhesive sheet D1, the deactivating adhesive sheet D1 is applied to the color - changeable adhesive sheet X1. were pasted together (second step).
- the laminate L1 of Example 1 was obtained.
- the laminate L 1 includes, in order, eagle glass, a color-changeable adhesive sheet X 1 (25 ⁇ m thick), a disabling adhesive sheet D 1 (25 ⁇ m thick), and a base film.
- Laminate L1 includes a laminated sheet of color - changeable adhesive sheet X1 and deactivating adhesive sheet D1.
- Example 2 A laminate L2 of Example 2 was obtained by carrying out the same steps as in Example 1 , except that the deactivated adhesive sheet D2 was used instead of the deactivated adhesive sheet D1 in the second step.
- Laminate L2 comprises , in order, eagle glass, color - changeable adhesive sheet X1, disabling adhesive sheet D2, and a base film.
- Laminate L2 includes a laminated sheet of color - changeable adhesive sheet X1 and deactivating adhesive sheet D2.
- Laminate L3 of Example 3 was obtained by performing the same steps as in Example 1 , except that in the second step, the deactivated adhesive sheet D3 was used instead of the deactivated adhesive sheet D1. .
- Laminate L3 comprises , in order, eagle glass, color - changeable adhesive sheet X1, disabling adhesive sheet D3 , and a base film.
- Laminate L3 includes a laminated sheet of color - changeable adhesive sheet X1 and deactivating adhesive sheet D3 .
- Laminate L4 of Example 4 was obtained by carrying out the same steps as in Example 1 , except that in the second step, deactivated adhesive sheet D4 was used instead of deactivated adhesive sheet D1. .
- Laminate L4 comprises, in order, eagle glass, color - changeable adhesive sheet X1, disabling adhesive sheet D3 , and a base film.
- Laminate L 4 includes a laminate of color-changeable adhesive sheet X 1 and deactivating adhesive sheet D 4 .
- Laminate L 5 comprises, in order, eagle glass, color-changeable adhesive sheet X 1 and substrate film (without disabling adhesive sheet).
- Example 5 A laminate L6 was obtained from the color - changeable adhesive sheet X1 and the deactivating adhesive sheet D1 in the following manner. First, the laminate L 1 (Eagle glass/color-changeable pressure-sensitive adhesive sheet X 1 /disabling pressure-sensitive adhesive sheet D 1 /base film) of Example 1 was prepared. Next, the base film was peeled off from the deactivated pressure-sensitive adhesive sheet D- 1 in this laminate L- 1 .
- a triacetyl cellulose (TAC) film (trade name “KC2UA”, thickness 28 ⁇ m, manufactured by Konica Minolta) and an adhesive tape having an ultraviolet absorption function (trade name “CS9934U”) , manufactured by Nitto Denko) and a polyethylene terephthalate (PET) film (trade name “G981 E75”, thickness 75 ⁇ m, manufactured by Mitsubishi Chemical Corporation) were laminated in this order.
- TAC triacetyl cellulose
- CS9934U an adhesive tape having an ultraviolet absorption function
- PET polyethylene terephthalate
- Laminate L 6 includes eagle glass, color-changeable adhesive sheet X 1 (thickness 25 ⁇ m), deactivating adhesive sheet D 1 (thickness 25 ⁇ m), TAC film, UV-absorbing adhesive tape, and PET film. (Base film) are provided in order. Laminate L 6 includes a laminated sheet of color-changeable adhesive sheet X 1 and deactivating adhesive sheet D 1 .
- Laminate L 7 is composed of Eagle glass, color-changeable adhesive sheet X 1 (thickness 25 ⁇ m), deactivating adhesive sheet D 2 (thickness 25 ⁇ m), TAC film, UV-absorbing adhesive tape, and PET film. (Base film) are provided in order.
- Laminate L7 includes a laminate of color - changeable adhesive sheet X1 and deactivating adhesive sheet D2.
- Laminate L 8 includes eagle glass, color-changeable adhesive sheet X 1 (thickness 25 ⁇ m), TAC film, UV-absorbing adhesive tape, and PET film (base film) in this order (disabling adhesive without a seat).
- Example 7 A laminate L9 was obtained from the color - changeable adhesive sheet X1 and the deactivating adhesive sheet D3 in the following manner.
- the color-changeable pressure-sensitive adhesive sheet X1 was prepared (first step). Specifically, after peeling off the release film from the color-changeable pressure - sensitive adhesive sheet X1, the same sheet was attached to Eagle Glass (thickness: 0.55 mm, manufactured by Matsunami Glass Co., Ltd.).
- the color-changeable pressure - sensitive adhesive sheet X1 on the eagle glass was irradiated with ultraviolet rays (UV) (second step). Specifically, under an environment of 23° C. and a relative humidity of 50%, the color-changeable pressure - sensitive adhesive sheet X1 on eagle glass was irradiated with UV from the base film side (the side opposite to the eagle glass). As a result, in the color-changeable pressure-sensitive adhesive sheet X1, an acid was generated from the photoacid generator, and the leuco dye was colored by the acid.
- UV ultraviolet rays
- a UV-LED lamp with a wavelength of 365 nm in a Quark Technology UV-LED irradiation device (model number “QEL-350-RU6W-CW-MY”) is used as a light source, and the wavelength is in the range of 320 to 390 nm.
- the integrated irradiation light amount was set to 8000 mJ/cm 2 .
- the disabling adhesive sheet D3 is applied to the color - changeable adhesive sheet X1. were pasted together (third step).
- a TAC film (trade name “KC2UA”, thickness 28 ⁇ m, manufactured by Konica Minolta Co., Ltd.) and an ultraviolet An adhesive tape (trade name: “CS9934U”, manufactured by Nitto Denko Corporation) having an absorption function and a PET film (trade name: "G981 E75", thickness: 75 ⁇ m, manufactured by Mitsubishi Chemical Corporation) were laminated in this order.
- Laminate L 9 includes eagle glass, colored variable color adhesive sheet X 1 (25 ⁇ m thick), deactivated adhesive sheet D 3 (25 ⁇ m thick), TAC film, and UV-absorbing adhesive tape.
- a PET film (base film) is provided in order.
- Laminate L 9 comprises a laminated sheet of colored variable color adhesive sheet X 1 and deactivating adhesive sheet D 3 .
- Laminate L10 of Example 8 was obtained by carrying out the same steps as in Example 7, except that the deactivated adhesive sheet D4 was used instead of the deactivated adhesive sheet D3 in the third step.
- Laminate L 10 includes eagle glass, colored variable color adhesive sheet X 1 (thickness 25 ⁇ m), deactivation adhesive sheet D 4 (thickness 25 ⁇ m), TAC film, UV-absorbing adhesive tape, A PET film (base film) is provided in order.
- Laminate L 10 comprises a laminated sheet of colored variable color adhesive sheet X 1 and deactivating adhesive sheet D 4 .
- Comparative Example 3 A laminate L- 11 of Comparative Example 3 was obtained by carrying out the same steps as in Example 7, except that the third step (bonding of the deactivating pressure-sensitive adhesive sheet D3) was not carried out.
- the laminate L 11 includes eagle glass, a colored variable-color adhesive sheet X 1 (thickness 25 ⁇ m), a TAC film, an ultraviolet-absorbing adhesive tape, and a PET film (base film) in this order. not equipped with a utilization adhesive sheet).
- a laminate L 12 was obtained from the color-changeable adhesive sheet X 1 , the deactivating adhesive sheet D 1 , and the mask film in the following manner.
- a color-changeable pressure-sensitive adhesive sheet X 1 (50 mm ⁇ 100 mm) was prepared (first step). Specifically, after peeling off the release film from the color-changeable pressure - sensitive adhesive sheet X1, the same sheet was attached to Eagle Glass (thickness: 0.55 mm, manufactured by Matsunami Glass Co., Ltd.).
- Laminate L12 comprises, in order, eagle glass, color - changeable adhesive sheet X1, mask film for partially masking color - changeable adhesive sheet X1, disabling adhesive sheet D1, and base film.
- Laminate L12 includes a laminate of color - changeable adhesive sheet X1, mask film, and deactivating adhesive sheet D1.
- Example 10 The same steps as in Example 9 were carried out except that the deactivated adhesive sheet D 2 (50 mm ⁇ 100 mm) was used instead of the deactivated adhesive sheet D 1 in the second step, and the laminate of Example 10 was obtained.
- L13 was obtained.
- Laminate L13 comprises , in order, eagle glass, color - changeable adhesive sheet X1, mask film for partially masking color - changeable adhesive sheet X1, disabling adhesive sheet D2, and base film.
- Laminate L13 includes a laminate of color - changeable adhesive sheet X1, mask film, and deactivating adhesive sheet D2.
- Laminate L14 of Comparative Example 4 was obtained by performing the same steps as in Example 9.
- Laminate L 14 comprises eagle glass, color-changeable adhesive sheet X 1 , mask film for partially masking color-changeable adhesive sheet X 1 , and base film in order (without deactivating adhesive sheet). .
- Laminate L15 of Example 11 was obtained by performing the same steps as in Example 1 except that the extraction adhesive sheet E1 was used instead of the deactivating adhesive sheet D1 in the second step.
- the laminate L 15 includes, in order, an eagle glass, a color-changeable adhesive sheet X 1 , an extraction adhesive sheet E 1 , and a base film.
- the laminate L 15 includes a laminated sheet of the color-changeable adhesive sheet X 1 and the extraction adhesive sheet E 1 .
- Example 12 A laminate L16 of Example 12 was obtained by performing the same steps as in Example 1 except that the extraction adhesive sheet E2 was used instead of the deactivating adhesive sheet D1 in the second step. .
- the laminate L 16 includes, in order, an eagle glass, a color-changeable adhesive sheet X 1 , an extraction adhesive sheet E 2 , and a base film.
- the laminate L 16 includes a laminated sheet of the color-changeable adhesive sheet X 1 and the extraction adhesive sheet E 2 .
- Example 13 A laminate L17 of Example 13 was obtained as follows. First , a variable color pressure-sensitive adhesive sheet X1 was prepared. Specifically, after peeling off the release film from the color-changeable pressure - sensitive adhesive sheet X1, the same sheet was attached to Eagle Glass (thickness: 0.55 mm, manufactured by Matsunami Glass Co., Ltd.). Next, after peeling off the base film from the color-changeable pressure - sensitive adhesive sheet X1 on the eagle glass, the color-changeable pressure - sensitive adhesive sheet X1 was immersed in ethanol together with the eagle glass (immersion treatment as a treatment for reducing coloring property). The immersion time was 2 minutes.
- the color-changeable pressure - sensitive adhesive sheet X1 with eagle glass was removed from ethanol and dried by heating at 132° C. for 3 minutes.
- a 38 ⁇ m-thick base film (trade name “MRF#38”, polyester film, manufactured by Mitsubishi Plastics Co., Ltd.) was attached to the color-changeable pressure - sensitive adhesive sheet X1 on the eagle glass.
- a laminate L17 of Example 13 was obtained.
- the laminate L 17 comprises, in order, eagle glass, a color-changeable adhesive sheet X 1 that has undergone ethanol immersion, and a base film.
- Example 14 A laminate L18 of Example 14 was obtained in the same manner as in Example 13, except that ethyl acetate was used in place of ethanol in the color reduction treatment.
- Laminate L 18 comprises, in order, eagle glass, a color-changing adhesive sheet X 1 that has undergone immersion in ethyl acetate, and a base film.
- Example 15 A laminate L19 of Example 15 was obtained as follows. First, a variable color adhesive sheet X 1 (50 mm ⁇ 100 mm) was prepared. Specifically, after peeling off the release film from the color-changeable pressure - sensitive adhesive sheet X1, the same sheet was attached to Eagle Glass (thickness: 0.55 mm, manufactured by Matsunami Glass Co., Ltd.). Next, after peeling off the base film from the color - changeable adhesive sheet X1 on the eagle glass, a 25 ⁇ m-thick mask film (trade name “Lumirror S10”, 50 mm ⁇ 50 mm, transparent polyester film, Toray) was placed on the same sheet. company) was laminated.
- Eagle Glass thickness: 0.55 mm, manufactured by Matsunami Glass Co., Ltd.
- the color-changeable pressure - sensitive adhesive sheet X1 whose surface (the surface opposite to the eagle glass side surface) was partially masked by the mask film was immersed in ethanol together with the eagle glass (as a coloration reduction treatment, immersion treatment). The immersion time was 2 minutes.
- the color-changeable pressure-sensitive adhesive sheet X 1 with eagle glass (the surface was partially masked with a mask film) was taken out of the ethanol and dried by heating at 132° C. for 3 minutes.
- a base film with a thickness of 38 ⁇ m (trade name “MRF # 38”, polyester film, Mitsubishi Resin Co., Ltd.) was pasted together. As described above, the laminate L19 of Example 15 was obtained.
- Laminate L 19 comprises, in order, Eagle glass, a color-changeable adhesive sheet X 1 that has undergone ethanol immersion, and a mask film and a base film on the same sheet.
- Laminate L 19 includes a laminated sheet of color-changeable adhesive sheet X 1 that has undergone ethanol immersion and a mask film.
- Reference Example 1 A laminate L21 of Reference Example 1 was obtained by performing the same step as the first step of Example 1 except that the color-changeable adhesive sheet R1 was used instead of the color - changeable adhesive sheet X1.
- Laminate L21 includes Eagle glass, color-changeable pressure-sensitive adhesive sheet R1 , and base film in this order.
- Laminate L22 of Reference Example 2 was obtained by performing the same step as the first step of Example 1 except that the color-changeable adhesive sheet R2 was used instead of the color - changeable adhesive sheet X1.
- Laminate L22 comprises, in order, Eagle glass, color-changeable adhesive sheet R2 , and base film.
- Reference Example 3 A laminate L23 of Reference Example 3 was obtained by performing the same step as the first step of Example 1, except that the color-changeable adhesive sheet R3 was used instead of the color - changeable adhesive sheet X1.
- Laminate L 23 includes Eagle glass, color-changeable adhesive sheet R 3 and base film in this order.
- Reference Example 4 A laminate L24 of Reference Example 4 was obtained by performing the same step as the first step of Example 1 except that the color-changeable adhesive sheet R4 was used instead of the color - changeable adhesive sheet X1.
- Laminate L 24 comprises, in order, eagle glass, color-changeable adhesive sheet R 4 and base film.
- the laminate was irradiated with ultraviolet rays (UV) (first UV irradiation).
- UV ultraviolet rays
- the color-changeable pressure-sensitive adhesive sheet in the laminate was irradiated with UV from the base film side.
- an acid was generated from the photoacid generator, and the leuco dye was colored by the acid.
- a UV-LED lamp with a wavelength of 365 nm in a Quark Technology UV-LED irradiation device (model number “QEL-350-RU6W-CW-MY”) is used as a light source, and the wavelength is in the range of 320 to 390 nm.
- the integrated irradiation light amount was set to 8000 mJ/cm 2 .
- the laminate was measured for average transmittance at a wavelength of 400 to 700 nm (second transmittance measurement).
- the apparatus and conditions used in this measurement are the same as the apparatus and conditions used in the first transmittance measurement.
- Table 1 shows the measured average transmittance as transmittance T 1 (%).
- the laminates L 1 to L 4 of Examples 1 to 4 had significantly smaller ⁇ T than the laminate L 5 of Comparative Example 1, and exhibited good discoloration suppression properties.
- the laminate L 5 of Comparative Example 1 (the color-reducing component is not blended in the color-changeable pressure-sensitive adhesive sheet) and the laminates L 21 to L 24 of Reference Examples 1-4 (the color-changeable pressure-sensitive adhesive sheet contains
- the difference in transmittance T1 from the sample containing the color-lowering component indicates the color-lowering performance of the color-lowering component.
- variable color adhesive sheets R 1 to R 4 since the coloring-reducing component exerts coloring-reducing performance, the transmittance decrease ⁇ T due to ultraviolet irradiation (external stimulus application) in the first system is UV irradiation (applying external stimulus) to the color-changeable adhesive sheets R 1 and R 2 (first system) of the laminates L 21 to L 24 and the color-changeable adhesive sheet X 1 (second system) of the same laminate L 5 is less than the decrease in transmittance ⁇ T' due to .
- the color-changeable pressure-sensitive adhesive sheet when the photoacid generator (first compound) and the color-developing compound (second compound) coexist with the color-reducing component before the coloring treatment, the color-changeable pressure-sensitive adhesive sheet is It can be seen that the coloring ability is low and coloring is difficult (Reference Examples 1 to 4).
- the predetermined region by impregnating the color-changing pressure-sensitive adhesive sheet after the predetermined region has been colored with the color-reducing component, the predetermined region can be sufficiently colored by exhibiting its coloring ability.
- the non-colored area transparent area
- can be prevented from being discolored present invention.
- the laminate was placed in the chamber of a weather resistance test device (trade name "Super Xenon Weather Meter SX75", manufactured by Suga Test Instruments Co., Ltd.). Specifically, the laminate was placed in the chamber such that the base film of the laminate was positioned on the light source (super xenon lamp) side. Next, in an environment of 55° C. and 55% relative humidity, the color-changeable pressure-sensitive adhesive sheet in the laminate was irradiated with light from a super xenon lamp (wavelength 300-400 nm) for 24 hours.
- a super xenon lamp wavelength 300-400 nm
- the laminates L 6 and L 7 of Examples 5 and 6 had a significantly smaller ⁇ T than the laminate L 8 of Comparative Example 2 and exhibited good discoloration suppressing properties.
- the laminates L 9 and L 10 of Examples 7 and 8 had a significantly smaller absolute value of ⁇ T than the laminate L 11 of Comparative Example 3, and exhibited good discoloration suppression properties. .
- the laminate was irradiated with ultraviolet rays (UV).
- UV irradiation method and conditions are the same as described above for the first UV irradiation.
- the average transmittance at a wavelength of 400 to 700 nm for each of the regions where the mask film is arranged (mask region) and the region where the mask film is not arranged (non-mask region) in the laminate is It was measured.
- the apparatus and conditions used in this measurement are the same as those used in the first and second transmittance measurements.
- Table 4 shows the measured average transmittance as transmittance T 1 (%).
- Table 4 also shows the difference in transmittance T1 between masked and unmasked areas (inter - regional transmittance difference).
- the laminate immediately after production was irradiated with ultraviolet rays (second UV irradiation), and then the average transmittance of the laminate was measured at a wavelength of 400 to 700 nm (fourth transmittance measurement).
- Another laminate after 48 hours from the production at 25 ° C. was irradiated with ultraviolet rays (third UV irradiation), and then the average transmittance of the laminate at a wavelength of 400 to 700 nm was measured (fifth transmittance measurement).
- Another laminate after 48 hours at 85 ° C. from the bonding in the second step is irradiated with ultraviolet rays (fourth UV irradiation), and then the laminate has an average transmittance at a wavelength of 400 to 700 nm.
- the equipment and conditions used for the second to fourth UV irradiations are the same as those used for the first UV irradiation.
- the equipment and conditions used in the fourth to sixth transmittance measurements are the same as those used in the first transmittance measurement. Let the average transmittance measured in the fourth transmittance measurement be the transmittance T 3 (%), let the average transmittance measured in the fifth transmittance measurement be the transmittance T 4 (%), and let the sixth transmittance Table 5 shows the average transmittance measured by transmittance measurement as transmittance T 5 (%).
- both the transmittance difference T 4 ⁇ T 3 and the transmittance difference T 5 ⁇ T 3 are significantly larger than the laminate L 5 of Comparative Example 1.
- a decrease in colorability (discoloration suppression property) was exhibited.
- the laminate L 16 of Example 11 had a high degree of deterioration in the colorability of the color-changeable pressure-sensitive adhesive sheet at higher temperatures (that is, the transmittance difference T 5 -T 3 was large), and exhibited excellent discoloration suppression properties. .
- the average transmittance at a wavelength of 400 to 700 nm was measured for the intermediate laminate obtained by laminating the color-changeable adhesive sheet X 1 (with a base film on one side) to Eagle Glass. (7th transmittance measurement).
- the laminate prepared through the coloring property reduction treatment is irradiated with ultraviolet rays (fifth UV irradiation), and then the average transmittance of the laminate at a wavelength of 400 to 700 nm is measured. (eighth transmittance measurement).
- an eighth transmittance measurement was performed for each of the region where the mask film was arranged (mask region) and the region where the mask film was not arranged (non-mask region).
- the equipment and conditions used in the fifth UV irradiation are the same as those used in the first UV irradiation.
- the apparatus and conditions used in the seventh and eighth transmittance measurements are the same as the apparatus and conditions used in the first transmittance measurement.
- Let the average transmittance measured in the seventh transmittance measurement be the transmittance T 6 (%), and let the average transmittance measured in the eighth transmittance measurement be the transmittance T 7 (%), Tables 6 and 7 shown in Table 6 also shows the difference ⁇ T ( T 7 -T 6 ) between the transmittances T 6 and T 7 .
- Table 6 also shows the transmittance measurement results (T 0 , T 1 , T 0 ⁇ T 1 ) shown in Table 1 for the laminate L 5 of Comparative Example 1 for comparison.
- Table 6 the laminates L 17 and L 18 of Examples 13 and 14 had significantly smaller ⁇ T than the laminate L 5 of Comparative Example 1, and exhibited good discoloration suppressing properties.
- Table 7 also shows the difference in transmittance T7 between the masked area and the non-masked area (transmittance difference between areas).
- Table 7 also shows the transmittance measurement results (T 0 , T 1 , transmittance difference between the masked area and the non-masked area) shown in Table 4 for the laminate L14 of Comparative Example 4 for comparison.
- T 0 , T 1 transmittance difference between the masked area and the non-masked area
- the method for suppressing discoloration of the color-changeable pressure-sensitive adhesive sheet and the laminated sheet of the present invention can be used, for example, in the manufacturing process of display panels.
- Color-changeable adhesive sheet Y Color-lowering sheet 11 First region (colored region) 12 Second area (non-colored area) 21 First member 22 Second member L Laminated sheet
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
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| Application Number | Priority Date | Filing Date | Title |
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| KR1020237029354A KR20230154822A (ko) | 2021-03-05 | 2022-03-01 | 가변색 점착 시트의 변색 억제 방법 및 적층 시트 |
| CN202280018456.3A CN116964168A (zh) | 2021-03-05 | 2022-03-01 | 可变色粘合片的变色抑制方法和层叠片 |
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| JP2021035205 | 2021-03-05 | ||
| JP2021-035205 | 2021-03-05 | ||
| JP2022027086A JP2022135979A (ja) | 2021-03-05 | 2022-02-24 | 可変色粘着シートの変色抑制方法および積層シート |
| JP2022-027086 | 2022-02-24 |
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| KR (1) | KR20230154822A (ko) |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62153377A (ja) * | 1985-12-27 | 1987-07-08 | F S K Kk | ウェハダイシング用粘着シート |
| JPH05323492A (ja) * | 1992-05-26 | 1993-12-07 | Fuji Photo Film Co Ltd | 画像形成材料 |
| WO2020189390A1 (ja) * | 2019-03-15 | 2020-09-24 | 日東電工株式会社 | 粘着剤組成物、粘着剤層及び粘着シート |
| WO2020188985A1 (ja) * | 2019-03-15 | 2020-09-24 | 日東電工株式会社 | 粘着シート、粘着シートの製造方法、中間積層体の製造方法および中間積層体 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11202110096QA (en) | 2019-03-15 | 2021-10-28 | Nitto Denko Corp | Pressure-sensitive adhesive composition, pressure-sensitive adhesive layer and pressure-sensitive adhesive sheet |
-
2022
- 2022-03-01 KR KR1020237029354A patent/KR20230154822A/ko unknown
- 2022-03-01 WO PCT/JP2022/008527 patent/WO2022186180A1/ja active Application Filing
- 2022-03-04 TW TW111107968A patent/TW202246444A/zh unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62153377A (ja) * | 1985-12-27 | 1987-07-08 | F S K Kk | ウェハダイシング用粘着シート |
| JPH05323492A (ja) * | 1992-05-26 | 1993-12-07 | Fuji Photo Film Co Ltd | 画像形成材料 |
| WO2020189390A1 (ja) * | 2019-03-15 | 2020-09-24 | 日東電工株式会社 | 粘着剤組成物、粘着剤層及び粘着シート |
| WO2020188985A1 (ja) * | 2019-03-15 | 2020-09-24 | 日東電工株式会社 | 粘着シート、粘着シートの製造方法、中間積層体の製造方法および中間積層体 |
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